The Big Picture

10 Thursday AM Reads

My morning train WFH reads:

SpaceX Bonds Are Trading Like Junk Bonds. What Does That Mean for Investors? BB-rated bonds are viewed as carrying a substantial credit risk for their holders. While investment-grade bonds have a historical default rate in the range of 0% to 1.02%, the default rate for BB-rated bonds has been about 4.22%, 4X higher than the riskiest investment-grade bonds. SpaceX carries a substantial debt load, about $29 billion in long-term bonds. A useful reminder that even the shiniest private darlings answer to the credit market. (The Globe and Mail)

5 Myths About AI’s Economic Impact, and What the Data Actually Shows: The AI economy is full of myths. Here are 5 worth challenging. Morningstar takes a data scalpel to five myths about AI’s economic impact. Sober counterprogramming to the hype cycle. (Morningstar)

Private-Equity Firms Are Sitting on a Nine-Year Backlog: Investors’ artificial-intelligence worries weigh on efforts to exit software holdings. A nine-year backlog of unsold companies is clogging private equity’s plumbing. The exits everyone assumed would come are simply not coming. (Wall Street Journal)

Pump.Fun’s Bounties Platform Is a Black Hole of Circular Grifting: The crypto platform claims you can “pay anyone to do anything,” from quitting a job on camera to getting a memecoin-themed tattoo. But it seems like people trying to scam each other. Wired on Pump.Fun’s bounties platform — a black hole of circular grifting, where the crypto grift funds the grift about the grift. (Wired)

Wikipedia Is Battling for the Soul of the Internet: The internet’s largest stockpile of free knowledge is under threat from MAGA, A.I. and foreign autocrats. A bibliophile ex-ambassador is here to help. Wikipedia — the last great noncommercial site — is battling for the soul of the internet, squeezed by AI scrapers and Elon Musk alike. (New York Times) see also ‘Let’s Go Kill the Internet’ Zuhair Lakhani ​is creating an army of AI influencers and flooding feeds with “propaganda campaigns.” What could go wrong?  Doublespeed is just one of a growing number of start-ups devoted to fabricating genuine virality online, some of which pay Discord users to create clips of podcasts, make fan edits of movie stars, and post glowing praise of whatever pop star has hired them. Lakhani’s pitch is one step beyond this: He wants not only to manufacture the trends but also to replace the real people involved with an army of AI influencers free of the human need for nuisances like payment or sleep. Each account is connected to its own physical phone in order to circumvent TikTok’s bot-detection systems. (New York Magazine)

Nobody Wants To Earn Their S***: A blunt cultural critique: nobody wants to earn their stripes anymore. Grumpy, yes — but not entirely wrong. (Panoptica)

There’s a New Way of War, but Is It Evolution or Revolution? Militaries worldwide are grappling with breakneck technological change and the lessons from Ukraine and the Persian Gulf. The WSJ asks whether drone-era warfare is evolution or revolution. Either way, the old playbook is toast. (Wall Street Journal)

US Air Force Engineer Charged With Sawing Down Flock Surveillance Cameras Receives Thousands of Dollars from Supporters Across the Country: “There’s also no shortage of citizens who prefer a more direct-action approach. Armed with garbage bags, spray paint, and even chainsaws, a not insignificant number of privacy vigilantes have taken the fight to Flock, using any means to free their neighborhoods of the ominous surveillance poles.” An Air Force engineer charged with sawing down Flock surveillance cameras is collecting thousands from supporters. Folk hero or felon — America can’t decide. (Futurism)

Extreme Heat Isn’t the Only Climate Impact Shocking Scientists: Much of the US just sweltered through the July 4 holiday weekend as an intense heat dome bore down, straining power grids and prompting the cancellation of many events. Wash, DC, saw a high of 102F (39C) on Saturday, a new local record for the date. In Europe, punishing temperatures are set to return days after a deadly heat wave pushed thermometers as high as 43.8C (111F) in France. A troubling pattern has emerged in this summer’s heat: Broken records, it’s done so often by margins far above the previous all-time highs. (Bloomberg free)

The World Cup gives America a unified look. The rest is complicated: These are images of America, at 250 years old, hosting the world’s grandest sporting event and partying like it’s 1776. But the jersey has never been just a jersey. It is a visual manifesto of a complicated country, and in the upkeep of long-recited ideals, it becomes a battleground. The politics of exclusion have infiltrated these colors, this flag, narrowing perspectives about who counts as a real American and who does not. In response, the politics of inclusion have turned to elitist derision, partly as a shield, but that only makes it easier to exile the faction from national pride. The Athletic on the World Cup’s tidy image of a unified America — and everything messier lurking just beneath the flag-waving. (The Athletic)

Video of the day: The Larry Sanders Show: The Show that Revolutionized TV Comedy – But Devastated Its Star

Be sure to check out our bonus episode of Master’s in Business with David Risher, CEO of Lyft, one of North America’s largest ride-sharing networks. He joined Lyft’s board in 2021 when the firm was burning cash and losing ground to Uber. Lyft has returned to profitability, with its stock rising more than 75% since Risher took the reins as CEO in 2023. In Q1 2026, the firm had 28.3 million active riders and did $4.9B in gross bookings, with $1.7B revs, and $132.8m in EBITDA. Previously, he held senior roles at Microsoft and Amazon.

 

America at 50, 100, 150, 200 & 250

Source: Bruce Melhman

 

Sign up for our reads-only mailing list here.

 

The post 10 Thursday AM Reads appeared first on The Big Picture.

MiB: Lyft CEO David Risher

 

 

This week, I speak with David Risher, CEO of Lyft, about his career path from Microsoft and Amazon to leading the ride-sharing platform. We discuss Lyft’s financial turnaround, cost-cutting measures, and strategies for expanding market share. Plus customer-centric features, the mechanics of ride data, and the decade-long transition toward autonomous vehicle networks.

A transcript of our conversation is below; His current reading is “Apple in China: The Capture of the World’s Greatest Company” by Patrick McGee, and “Good People: A Novel” by Patmeena Sabit.”

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube (video), YouTube (audio), and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

Be sure to check out our Master’s in Business this weekend with McKeel Hagerty, CEO/Chairman of Hagerty Specialty Insurance. He transformed a family specialty-insurance agency into an enthusiast-driven platform focused on collectible cars, events, valuation data, and auctions. HGTY is now a public company that insures everything from classic cars to boats, trucks, tractors, and military vehicles for over 2.8M collectors.

 

Spotify

 

 

MASTERS IN BUSINESS An Interview with David Risher, CEO of Lyft
Hosted by Barry Ritholtz  ·  Bloomberg Radio

 

ANNOUNCER (00:00:02):  Bloomberg Audio Studios: podcasts, radio, news. This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

BARRY RITHOLTZ (00:00:16):  This week on the podcast — man, was this a fascinating conversation. David Risher has been CEO of Lyft for the past three years; he’s been on the board for the past five years. What a fascinating discussion about a company that is probably an app on your phone, and you may not be aware of all the different things they do — from bike share, to autonomous vehicles, to fleet management, and everything in between. I thought this was absolutely fascinating, and I think you will also. With no further ado, my conversation with Lyft’s CEO, David Risher.

DAVID RISHER (00:00:55):  Thank you, Barry. I am happy to be here.

BARRY RITHOLTZ (00:00:56):  I’m thrilled to have you. Before we start talking about your technology background, I gotta roll a little further back: a bachelor’s in comparative literature from Princeton. That doesn’t sound like the sort of career plan for someone who’s gonna work his way through technology companies. What was the original idea?

DAVID RISHER (00:01:16):  So this goes way back, and the funny thing is, it even goes to high school. My mother bought an Apple II computer a million years ago to help her run a small business, and I sort of got into technology that way. I will admit, part of it, I think, is I had terrible handwriting. And so when I used the computer to print out stuff for my high school English teacher, she could finally read what I was writing. It probably gave me a better grade as a result. So I sort of got into computers a little bit as a kid, ended up at Princeton, writing my thesis on a computer — again, this is a million years ago, when that wasn’t normal. And so I found myself just interested in technology, and after going to a consulting firm for a couple years to learn about the business world and going to business school, I found myself as an intern at Microsoft — again, back in 1990 — and the rest is sort of history.

BARRY RITHOLTZ (00:02:09):  So, Harvard Business School — we know what that typically leads to. I’m curious how the humanities background helped shape the way you think about business, about leadership, about working with people. What was the upside of humanities for you?

DAVID RISHER (00:02:26):  You know what, I really appreciate the question, and I actually think it’s more relevant now than ever. Look, the humanities is all about curiosity and understanding, and maybe even empathy, right? If you read a book, you have to understand — you’re exposed to different people’s perspectives. It’s almost like you’re crawling inside someone else’s brain, particularly if you’re reading fiction. And so, to a certain extent, I think nothing could prepare you better. Now, you have to have an analytical brain. You might also have to be good with numbers in business. But the humanities world — I sort of think of it as this kind of magic vaccination against irrelevance, because that curiosity is always gonna matter. And it certainly helped me through my whole career.

BARRY RITHOLTZ (00:03:05):  I love that answer. So you intern at Microsoft. You end up beginning your career there, where you helped to launch their first database product, Access. Tell us about that.

DAVID RISHER (00:03:17):  Sure. So Microsoft was famously ahead — or at least getting ahead, let’s say — with the launch of Windows, in word processing, in spreadsheets, of course. And again, this is sort of ancient business history, but it’s a fascinating tale of a technology shift, completely reshuffling the deck away from old companies like WordPerfect and Lotus 1-2-3. We don’t even know who those companies are anymore, because Microsoft took over that space. And it’s really because Windows shifted the platform — we might come back to that idea when we talk about autonomous cars. But they didn’t have a database, and that was sort of the third big product that a lot of companies wanted. I helped develop it; I was the first product manager on it. And really, all that meant is my job was to go around and watch other people use competing products at the time — Paradox, dBase, again, products that don’t even exist anymore — and try to pay attention to what they were doing with these products. How were they using them? Where were they stumbling? That was my first role. And in a sense, it has been one of the most important jobs I ever had, ’cause it’s what sort of taught me about understanding what customers want.

BARRY RITHOLTZ (00:04:17):  Huh, interesting. And then you founded Microsoft Investor and launched that product. That is so far afield from databases. What led to that transition?

DAVID RISHER (00:04:29):  Okay, so you’re making me realize that there’s a theme of my life I hadn’t really thought of before, which is platform shifts. So when I joined Microsoft, Windows was the product, right? This was the thing that was gonna run software, and of course it became incredibly successful. But then 1995, 1996, 1997 comes around — the internet is here. And Microsoft, like any tech company at the time, had to figure out its internet strategy. And it decided that there were a couple of key products that needed to be available on the World Wide Web. Actually, I think “the information superhighway” literally was the way people talked about it. It’s crazy. So —

BARRY RITHOLTZ (00:05:04):  Cliché. It’s amazing.

DAVID RISHER (00:05:05):  So cliché. But there it was — no one even knew how to talk about the thing. So anyway, I had been a little bit interested in personal finance, and a couple of threads came together. Microsoft tried to buy a company called Intuit — still very successful — and was unsuccessful, blocked because of the Justice Department. And so we decided we needed personal finance. And I said, you know what, why don’t we develop this product — a personal finance product — for the internet, not as packaged software.

BARRY RITHOLTZ (00:05:29):  Huh. Really, really interesting. And then, staying with the theme of platform shifts: employee number 37 at Amazon. That is just an absolutely bonkers number. Senior VP of US retail — when you joined the firm, revenue was $15 million. You helped ramp that up to $4 billion. Obvious question: when you joined Amazon, did you have any idea what the behemoth it would become? Or was it still, hey, we’re hanging on by our fingernails and maybe this’ll work out — or anywhere in between?

DAVID RISHER (00:06:07):  It was sort of both at the same time, and it was almost always gonna be one or the other, right? So I remember — I’ll tell you a little of the story of how I got there. My phone rings one day at Microsoft, and it’s this guy Jeff, and he’s doing a reference check of a woman who used to work, actually, at Microsoft in the personal finance group. So it all kind of connects. And so we get to talking, and one thing leads to another, and he is very precise about the way he’s asking questions. Remember, the company had maybe 10 people at this point. It was very, very small. But he had a big vision. You know, he was gonna be Earth’s biggest bookstore.

BARRY RITHOLTZ (00:06:42):  At the time — wait, hold on, let me just stop you. When you say “this guy, Jeff” — this isn’t just some guy in HR. Jeff Bezos is calling you to do a background check on a potential hire.

DAVID RISHER (00:06:55):  Exactly.

BARRY RITHOLTZ (00:06:56):  So go on — Jeff calls.

DAVID RISHER (00:06:58):  So Jeff calls me, and literally, at the time, he was just this guy, Jeff.

BARRY RITHOLTZ (00:07:02):  “Hey David, some guy named Jeff on the phone. Pretty much a background check for an employee.” So what was that conversation like?

DAVID RISHER (00:07:09):  Well, he had — to take you back then, but in a sense it’s still the Jeff of today — he had a plan, and it was a 25-question plan for the phone call, right? And to this day, the question I remember the most clearly was: “It’s very clear you are a fan of this person — give me an example of a job that she wouldn’t be a good fit for.” And it was such a clever question, because inevitably in background checks, you’re trying to say nice things about the person, right? But this is an invitation to say, well, you know, maybe a very detail-oriented job might not be the best fit. Or maybe something that manages a lot of people. It’s something like this that would give him some sense of where an area to probe more is. Anyway, at the end of that conversation — literally 45 minutes into it — he says, you know, you sound like a good guy. I said, oh, you sound like a good guy as well. And so a couple days later, he and MacKenzie, his wife at the time, and Jen, my wife currently still, and I went out to dinner, got to know each other, and over the course of the next year, got to know each other a little bit better. And then I ended up applying for this job to help Amazon grow beyond just books. That was really the job.

BARRY RITHOLTZ (00:08:16):  And how’d that work out?

DAVID RISHER (00:08:18):  It worked out pretty well. But you know what, it wasn’t obvious at the time. During the interview, I remember he said — look, if we play our cards right — and as you say, it was a $15.6 million store at the time, so tiny, tiny little thing — he said, if we play our cards right, maybe by the year 2000 — this is in 1996 — we might be a billion-dollar company. Maybe, maybe. But a lot has to go right in order for that to happen. Obviously we got there, and then we got, you know, far beyond. But there were all kinds of people who frankly were sort of rooting for our failure — competitors, Barnes & Noble at the time, a bunch of Wall Street analysts who thought this was just some sort of crazy Ponzi scheme, whatever.

BARRY RITHOLTZ (00:08:56):  It was, “No one’s gonna buy anything on the internet. What are you guys doing? This is a dumb idea.”

DAVID RISHER (00:09:00):  Totally, totally. Well, and not only that, but also: the costs are gonna be huge. You’re gonna have to build out these distribution centers and warehouses. The internet is unproven technology. All sorts of things that just —

BARRY RITHOLTZ (00:09:12):  No one’s giving you a credit card over the internet, correct?

DAVID RISHER (00:09:14):  Correct. Who’s gonna trust you?

BARRY RITHOLTZ (00:09:15):  I remember getting an Amazon gift certificate from my college roommate — this was decades ago, right after Amazon formed. And the first time you go through the experience of buying something, it’s like, oh, this makes perfect sense. I don’t have to go to the store, I don’t have to waste time. This is great. I mean, there are certain stores that are fun to browse, but for the mundane sort of stuff, he was just decades ahead of everybody else.

DAVID RISHER (00:09:46):  In that way — and in realizing that it’s really the customer experience and customer obsession that’s gonna drive your continued growth. Because all those things are true. And as he would say, famously, you’re always one click away from competition. So that’s the downside, right? How do you continue to compete in a world where theoretically someone else could start, and someone else could start, and someone else could start — and you don’t have any geographic advantage over them?

BARRY RITHOLTZ (00:10:09):  And they kind of owned that space for the longest time. Really, it was only the pandemic, when people were outta things, that forced everybody: all right, now I have a Target account, now I have a Walmart account, now anybody else who could deliver. And what’s been surprising is how they’ve just powered right through. Hasn’t really slowed him down very much.

DAVID RISHER (00:10:27):  That’s right. That’s right.

BARRY RITHOLTZ (00:10:31):  So you go from Amazon — you kind of tap out a couple of years later. You teach at the University of Washington’s business school; you were elected Professor of the Year in 2004. And then you spend 13 years running Worldreader, a nonprofit dedicated to helping children learn to read in underserved communities. This is yet another pivot — platform shift, right? What was it? Just like, all right, I have my Microsoft stock came in, Amazon recovered from the dot-com implosion, that’s doing fine — I could just do something for fun? What was the thinking behind the shift?

DAVID RISHER (00:11:11):  No, it wasn’t that, actually — it was sort of a different thing. So you asked me a couple questions ago what my career idea was as a kid. Honestly, if I had had to guess, I might have said, you know, maybe I’ll be an English professor someday, or something like that. I’d wanted to teach, and I loved reading. And so this was a way for me to bring together a couple of different things in my life — obviously books and literacy, ’cause that was sort of the passion and focus, but also technology. The thesis of the company was: kids are gonna read using tech. And that’s how it’s gotten to be — millions and millions of kids later are all reading on the platform. It started out with Kindle, a product I know something about because of my Amazon days, and brought sort of technology and reading together. So that was really the focus.

BARRY RITHOLTZ (00:11:53):  And then what ultimately ended up bringing you back into the corporate sector, after a long time in academia and nonprofits?

DAVID RISHER (00:12:01):  Yeah. So here it was — one day my phone rings, and a guy named Sean Aggarwal is on the other end of the line. Sean and I had worked together many years before, back at Amazon. He was my kind of finance partner. He had subsequently become an investor and then the board chair of Lyft. And he and John and Logan, the co-founders of Lyft, really were looking to do something quite unusual at the board level, which was: bring someone in who is a real customer advocate. So boards — for those of you who haven’t gotten a chance to be exposed to a board — typically are made up of kind of finance people, business strategists, maybe people who’ve built companies before. But often, by the time you get to sort of the board level of a company, you’re pretty far away from the customer. And John and Logan, again to their credit, said, you know what? We need some more customer advocacy right from the top. We need some more support, frankly, for that kind of vibe, as well as someone who’d helped scale a company like Amazon. You know, I also learned a lot about competing at Microsoft, and even at Worldreader — nonprofits, people sort of look at them and think they’re not very much, but it’s very, very difficult to actually scale a nonprofit, because the funding is always tight and so forth. So I think they were looking for someone with a combination of scaling experience but also real customer advocacy. And so I joined the board as a result.

BARRY RITHOLTZ (00:13:18):  And then eventually, a couple of years later, you get offered the role of CEO. What was that like? How did that come about? Infrequently do board members become CEOs.

DAVID RISHER (00:13:36):  So, funnily enough — and this one I’ll sort of slow the story down again, because it actually was Sean Aggarwal again, same board chair — he calls me up. It happened to be on Valentine’s Day, of all days, so I remember the day, in 2023. And the backstory here is John and Logan, again, the co-founders of Lyft — this is what they had been doing for 15 years nonstop. It was literally their first job outta college: founding this whole new company, withstanding the onslaught of an incredibly competitive environment, an incredibly operationally complex environment, 24 hours a day, seven days a week, for year after year. So at the end of the prior year, they said to the board, you know what, it’s time for us to move on. We’ve sort of done what we need to do. And frankly, the company was going through a bit of a tough time financially and operationally, and I think they realized that they were sort of getting to the end of where they could really help. So the board did what it does — boards do this — they form a special committee, they start to recruit, look around. I wasn’t on the committee; I was sort of watching from the side. But, as they say, then my phone rings one day, and it’s Sean on the phone with John and Logan, and they basically say: you know what we’ve been thinking? As we’ve been looking at external people, frankly, we think we might have the right person to at least apply for the job — let’s be clear, apply for the job — sitting right here, you know, on the board. And I said, what are you talking about? They said, we’re talking about you, David. I said, absolutely not.

BARRY RITHOLTZ (00:14:56):  Really — your first reaction was, hey, thanks, but no thanks?

DAVID RISHER (00:14:58):  Zero percent chance. I literally said, you should hang up the phone right now, because you’ve got better things to do. There’s just no way. But you know what? As the day wore on, I found myself saying, you know what, this is a really interesting opportunity. How many people get this opportunity? To run a — and I’d never run a public company before. I mean, my God. But at the same time, I had learned some things at Microsoft. I’d learned some things at Amazon. I learned some things at Worldreader. I learned some things in various different ways in my life. And I had a lot of passion for the company, having been on the board — and also a real understanding that as a board member, you really only have so much power and influence. It’s fairly limited. But as a CEO, it’s a different thing. So anyway, one thing led to another. I applied, and went through kind of a harrowing experience, but ended up getting the job.

BARRY RITHOLTZ (00:15:40):  Huh — really, really fascinating. So, we mentioned earlier: you joined the board in 2021, you’re named CEO in 2023. When you joined the company, they were still reeling from the pandemic and all the factors that drove the company — losing not only money, but also losing market share to their big competitor, Uber. What did you find when you looked under the hood? What surprises were awaiting you as CEO?

DAVID RISHER (00:16:11):  So the first, maybe, meta-observation — and you’re teeing it up — is: gosh, you’re on the board of a company for a couple years, you kind of think you know the company. You don’t really know the company. I mean, if any board members are out there, you think you do, and you probably have a pretty good sense of certain things, but you get in there and everything is 10 times bigger, worse, better — all the things. Then you realize: okay, what did I see? I saw a company that had some real innovative spirit at its core. Remember, Lyft was actually the one that really revolutionized rideshare. So the other guys, they came up with a sort of black-car concept — you know, black car on an app — but it was really Lyft that said, you know what, it can be anyone with a Prius. You know what I mean? Anyone can pick up. So this company had innovated from the early days, but honestly, its innovative spirit had maybe gotten a little the best of it. Tried a few too many things, spread a little too thin, losing share. And its core business, as you say — not priced well, not paying competitively. So a number of different, just basic issues. So what do we do the first, frankly, couple of weeks? Well, first thing is lower prices. We were just priced too high.

BARRY RITHOLTZ (00:17:15):  Did you do big announcements around that? Because I don’t — 2023 is still kind of a blur to me.

DAVID RISHER (00:17:20):  So we didn’t, and here’s why. In order to withstand a price drop — because it’s a very competitive business and you’re doing a lot of volume — if you drop your price, you gotta make sure you can pay for it. We had to do some other things as well. So, for example, we had to reduce our costs significantly. So we laid off — it was about a third of the company. And yeah, 26%, actually, of the company, now I think about it.

BARRY RITHOLTZ (00:17:41):  Wow.

DAVID RISHER (00:17:45):  $330 million of savings. That was a very, very significant shock to the company, by the way. We also had to raise driver pay. So we had a lot to pay for.

BARRY RITHOLTZ (00:17:53):  So wait — you’re simultaneously lowering prices for Lyft riders and yet bumping up pay for drivers. That sounds like that’s gonna cause a big problem for profits.

DAVID RISHER (00:18:03):  So that’s exactly right. So in order to pay for it, you have to figure out how to pay for it. And frankly, our cost structure was just sort of outta control. We were doing too many things. We had too many people — and by the way, those people were all working remotely, which makes it quite difficult to really kind of change the culture to a customer-obsessed culture, which was my other big thing. And by the way, we were also overpaying in stock-based compensation, which was bugging investors. So in the first couple of months, it wasn’t really the time to be bragging. It was the time, frankly, to be saying, okay, we’ve got some things to fix, and let’s really focus on that. So first — call it thirty, sixty, ninety days — it’s fixing some basics, but also reorienting the company back towards its customer-obsessed roots. And I’m still very — I guess I’d say proud of this: the first meeting I had of the day was literally getting my computer and my laptop, and the second meeting, 10 o’clock in the morning, Monday morning, I said, let’s start talking about a product that’s now called Women+ Connect — trying to get women drivers and women riders —

BARRY RITHOLTZ (00:19:02):  Such a great idea, especially given the mayhem across the street from you.

DAVID RISHER (00:19:06):  I appreciate you saying that. And it really matters. And this is something the company —

BARRY RITHOLTZ (00:19:11):  And I’m sorry to interrupt, please — it’s very visible on the app, that choice, which shows some thoughtfulness. And, oh, there’s this problem — how about we send a woman driver for you, and you don’t have to worry about what you’re hearing about elsewhere. Exactly. It just makes so much sense.

DAVID RISHER (00:19:28):  I really appreciate you saying that. It was an easy decision in that sense. All you have to do is talk to 10 women and say, well, what are you thinking? And they say, well, gosh, particularly late at night, maybe in a new city, maybe I’ve had a long day — it’s just not my jam to be talking to a dude. Right? It’s all right, dudes, you know — like that. But sometimes the easiest ideas are also the most complicated. There are all sorts of potential legal issues, all sorts of operational issues. There are even, to a certain extent, cultural issues of, like, is this gonna be okay? But I was like, you know what? I think it’s gonna be okay. I think it’s gonna be okay. So that was an early decision we made. It came out — that was in April of 2023 — we launched that later that year. And it was really exciting for the company to say, you know what, we can do big things again, and we can start to innovate again on behalf of customers.

BARRY RITHOLTZ (00:20:09):  Huh — kind of fascinating. Coming up: we continue our conversation with David Risher, CEO of Lyft, discussing the future of rideshare technology. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

BARRY RITHOLTZ (00:20:21):  I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio. My special guest this week is David Risher. He is the CEO of Lyft, one of North America’s largest and fastest-growing ride-sharing networks. So over the next year or so, you return Lyft to profitability. In the most recent reported quarter — first quarter 2026 — over 28 million active riders, nearly $5 billion in gross bookings, $1.7 billion in revenues, just about $133 million in EBITDA profits. So the combination of restructuring the company, attracting — paying more — drivers, and discounting prices for riders puts you on the right foot. How do you build on that? What’s the next step to maintain that momentum?

DAVID RISHER (00:21:25):  Well, so in some sense, nothing changes, and in some sense, everything changes, okay? So what doesn’t change: customer obsession is still driving profitable growth. That’s just gonna be a theme I go with forever. You know, maybe I’ve drunk a lot of the Jeff Bezos Kool-Aid, but it seems to be working out pretty well. So one other financial metric that has been interesting to watch: when I joined, we were losing about $300 million — consuming about $300 million in cash — over 12 months. We’re now generating about $1.1 billion in cash over 12 months.

BARRY RITHOLTZ (00:21:53):  Okay. So what that allows you to do is invest in the future. What does that look like?

DAVID RISHER (00:21:58):  Certainly it looks like international expansion. So that’s been one thing we’ve been at for about the last year. Lyft was sort of — I almost say caught a little bit in a US-centric view of the world. And it just doesn’t make sense: once you have a product that scales really well, and is sort of a fixed-cost-based type of thing, you really want it to be around as much of the world as possible, so you can run as much volume through that platform as possible. So we bought a company called FREENOW last year. It’s a European taxi aggregator —

BARRY RITHOLTZ (00:22:28):  FREENOW?

DAVID RISHER (00:22:29):  FREENOW. Yeah. It is Europe’s biggest taxi aggregator, which means that if you want a taxi and you’re in a place like Barcelona or London — pick your favorite city; they operate in nine countries — the FREENOW app is gonna be your best way to get it. That gives us a great platform for expansion, even when it comes to autonomous vehicles — we’ll come back to that, I’m sure, in a couple seconds. So that’s one direction of expansion. You think of that as out — overseas. Another dimension is up — upmarket. You just kind of referred to this. So Lyft, again — it sort of started, its tradition was, as kind of a relatively inexpensive, very available rideshare option, but it wasn’t as strong in kind of the black, you know, kind of luxury segment. We bought a company called TBR last year. TBR is a high-end chauffeur company. We also have a very, very good Lyft Black product. In fact, if you’re listening to this, I promise: if you haven’t tried it, give it a try. I think you’ll like it. It’s actually our highest-rated product. You know, a nice black car comes and picks you up. So that’s another area of expansion for us, because that gives us, frankly, more margin to play with, but it also allows us to talk to a segment that we haven’t talked to very much. And then, of course, autonomous vehicles. So these are all nice uses of cash. Once you’re generating cash, you can start to either acquire companies, or you can invest in things that then grow — build sort of the next chapter of growth.

BARRY RITHOLTZ (00:23:44):  So I appreciate you mentioning the various tiers. There’s this tendency to think of the consumer — especially the American consumer — as one thing, but we both know that’s not true. You get to crunch a whole lot of data. What are you seeing in terms of income, geography, various times of day? Like, what do the metrics tell you about the different flavors of consumers using Lyft?

DAVID RISHER (00:24:11):  Yeah, this is such an interesting issue, and it’s not something I really appreciated. You know, we are gonna do about a billion rides this year, and so, to your point, with a billion rides, you kind of get a sense of how people are spending their time during the day. So I’ll tell you two things that are growing quite quickly. One is party time. And it might be funny to start there, but party time — I should say what that means. What that means is a Thursday night, really Friday night and Saturday night, call it nine and midnight. And it is really interesting — I think this is not just post-COVID, but I think, frankly, a little bit of app fatigue is driving people to say, you know what? Let’s actually get out and spend our lives out in the real world, instead of spending all of our lives on apps. So I think that’s — actually, I’m quite comforted by that. And it’s actually a big part of our sort of overall purpose, which is to serve and connect people. I’m a lot passionate about that. At the same time, commute as well. And I do think this is a certain post-COVID thing, where people were sort of thinking, maybe we’ll just be in our houses the rest of our life, working remotely. It turns out a lot of companies and a lot of people are saying, I wanna get back to work. And I think these things are somewhat connected — and sorry for sounding a little bit like a social psychologist a little bit, but I mean, gosh, I met my wife at Microsoft. A lot of people have really significant life events that happen at work that are not just work, right? And so I think there’s a little bit of that. So anyway, when I look at things like commute hours — and then travel continues to be really strong as well. And this is — look, I’m a million years old now. When I was a kid, the idea of getting on a plane and going overseas — I mean, you might as well say go to the moon. Now, 20- and 30-year-olds are like, yeah, I’ll sort of take a trip overseas, or I’ll go to, you know, whatever — Nashville for the weekend, or something. So anyway, I think these are pretty big, real societal shifts, as people want to kind of be out in the real world.

BARRY RITHOLTZ (00:25:51):  I’m kind of fascinated by the idea of party time, ’cause pre ride apps, there was always the question: all right, I’ve had two, I guess I’m driving tonight, so I gotta stop here. But if you’re out on party night and you know you’re taking a car home, you are not afraid about having a second or third drink. You can kind of relax a little bit. Getting pulled over is not a problem if you’re in somebody else’s Lyft.

DAVID RISHER (00:26:19):  It’s exactly right. So again, if you zoom out — you know, Wall Street looks at companies like ours quarter by quarter, and it sort of drives you crazy. But if you zoom way, way out, let’s look at that from a different dimension. Now, average car right now: 50,000 bucks. Okay? Average monthly payment: 800 bucks. Insurance will cost you another couple hundred bucks. Gas might cost you another hundred bucks or so, at least now. And then service will cost a little bit more than that. Okay? So that’s plan A. And by the way, if you take on all that responsibility, there’s no texting and there’s no drinking. You know what I mean? Now, plan B: pay 20 bucks getting a Lyft. Someone else does the driving. Text to your heart’s content, drink as much as you want — if that’s your jam. And it’s 20 bucks, not 800 bucks times, you know, plus, plus, plus. So just looking out — again, you’re sort of asking about kind of segments, and sort of, maybe, a little bit, the role of technology in society. I still think we’re actually at the beginning stages of a lot of these changes. And sometimes, again, people who have been around for a while don’t even realize how much the world has changed in that way.

BARRY RITHOLTZ (00:27:21):  Yeah. Fascinating data point I saw — it was actually a couple of years ago — the number of kids under 19 that haven’t gotten a driver’s license. When I was growing up, you couldn’t wait to get your driver’s license, ’cause that meant freedom. There wasn’t an internet. There were three channels, plus some people started getting cable. Like, it was a very different world back then. That’s right. And now it’s like, yeah, maybe I’ll get a license, maybe I won’t. How do you think about marketing to that demographic?

DAVID RISHER (00:27:51):  Well, so one of the things I learned from Jeff — again, who’s, as you can imagine, quite an influential boss for me — is: build your businesses on things that don’t tend to change. Not things that are sort of ephemeral. So what are some things that aren’t gonna change? Okay — again, people are gonna want to get out, either to the doctor or to go to a bar. So that’s a good bet. People are also gonna want to save money. And so a lot of our focus right now — and you’re gonna start to see a lot of marketing around this — is: save money, check Lyft. Now, I wanna be super clear here. It’s not — if I look at the competitor — that we always have a better price. Of course we try to, but we don’t always; sometimes, you know, all sorts of things happen. But over time, if you check both apps, you’re gonna save some money. And certainly, compared to buying a car of your own and dealing with all the maintenance, you’re gonna save some money. So it’s not the only thing I wanna say, but I actually think it’s an important thing to say — particularly in a world of sort of some economic instability — this is a good way for you to save some money. And frankly, I’m proud of our cost position, and I’m proud of our ability to offer a great price every single day, you know, a billion times a year.

BARRY RITHOLTZ (00:28:54):  So let’s talk about you versus your competitor. Lyft has always been framed as sort of the underdog to Uber. Is this kind of a Coke and Pepsi story? What are the advantages of being number two? Remember the old — was it Avis? We’re number two, we have to try harder.

DAVID RISHER (00:29:13):  Absolutely. So I like being number two, and it’s maybe a funny thing to say, but I do think it means you try harder. You wake up every single morning and you say, I got one job, which is to, frankly, do a great job for my riders and my drivers, such that maybe over time I can overtake the other guys. I guess the way to think about that is: I think the right number of rideshare companies in most markets is probably two. It’s a capital-intensive business — not because you own the cars, but because you own a lot of server capacity, and it’s quite complicated to figure out pickup and drop-off locations, and customer service — people leave their phones in the car about 8,000 times a week. It’s just all sorts of —

BARRY RITHOLTZ (00:29:56):  Especially Friday party night.

DAVID RISHER (00:29:58):  Right — and there you go. It all kind of comes together. There is something to that. And by the way, we have really cool innovation coming out there — we’ll bring your phone back to you automatically. But that’s a separate story. But anyway, so in a funny way, it’s not a bad thing to be in sort of a two-player position, ’cause you really only have one competitor. And frankly, if you spend too much of your time thinking about that one competitor, you’re probably losing the script. Because guess what? There are a lot of rides that people aren’t even taking on rideshare at all. Okay? So, you know, back to this question — we’re a customer-obsessed company, and this is gonna be the thing. This is why we’re growing, you know, mid double digits — 15 to 20% year on year. It’s why we’ve become profitable. It’s why we’re spinning off cash. And I think that is a good place to be. Particularly when I look at the other guys, who I tend to think of, frankly, as more — I’ll call them sort of financially and maybe technologically driven. Maybe — I don’t know exactly how they describe themselves — but I don’t get the customer-obsessed vibe.

BARRY RITHOLTZ (00:30:52):  Huh — so that’s kind of interesting. Let’s talk about an example where there’s no customer-obsessed vibe. So I use Lyft, I use Uber. It feels like on Uber, the way it measures time is sort of an alternative reality. Hey, we’ll find a driver in three minutes — it takes nine minutes. Hey, the car will be here in 11 minutes — it’s there in 23 minutes. Like, the app is very full of BS. It consistently lies. I’m curious: is it just a logistical issue that everybody has to deal with? Or — and we know a lot about the history and culture of your biggest competitor — is this a culture problem? You know, their history has a lot of bad behavior, a lot of, let’s just call it questionable legality. I wouldn’t go so far as to say fraud, but they did a lot of bad things. Does that show up in how the app behaves? Or is this just, no, Google Maps is tough to work with, this is a logistical challenge?

DAVID RISHER (00:32:00):  No, it is a logistical challenge. But — look, I’m not gonna characterize you; you did a marvelous job characterizing them. Skirting —

BARRY RITHOLTZ (00:32:09):  I got nothing — no liability for slander there.

DAVID RISHER (00:32:12):  There we go. Fantastic. Exactly. So Barry’s got a whole second — hold on, well, you were a lawyer, right?

BARRY RITHOLTZ (00:32:16):  Yes, that’s correct.

DAVID RISHER (00:32:17):  Oh, there we go.

BARRY RITHOLTZ (00:32:18):  Okay, but I’m recovered, so —

DAVID RISHER (00:32:20):  It’s not the same. I understand — recovered lawyer — but you did just hear a lawyer very carefully parse his words. Okay, listen, I won’t comment on that. What I will say is: we are very focused — for example, you’re talking about reliability. Oh my goodness. You talk to my team, and they will — they roll their eyes, maybe, would be one way to say it. But the number of times I talk about reliability internally is high, because I am obsessed by saying: if we’re gonna make a promise, we’re gonna meet the promise. And starting in a couple weeks, we’re actually starting to do some more work to actually surface that promise, even a little bit more visibly. We do it today for airport pickups. If we’re more than 10 minutes late for an airport pickup, we pay you up to a hundred bucks, no questions asked.

BARRY RITHOLTZ (00:32:54):  Really?

DAVID RISHER (00:32:55):  Yep. And we rarely have to do that. Our reliability rate is above 99% for scheduled airport pickups.

BARRY RITHOLTZ (00:32:58):  Wow.

DAVID RISHER (00:33:00):  So we’re very, very focused on that. You know, I will say — look, at business school, there’s a very famous class which has a weird technical name, but it’s basically about incentives and behavior —

BARRY RITHOLTZ (00:33:13):  What’s the name of the class?

DAVID RISHER (00:33:15):  So I was in school a long time ago — I think it’s called CCMO, and I don’t even remember what it stands for anymore. It’s probably called something different today. But it really is about how incentives drive behavior — financial incentives and other incentives, and incentive alignment, and so forth and so on. There is an incentive in the sort of on-demand app world not always to be truthful. Because if you overpromise something, and then you kind of hook a person in — what are they gonna do? If they cancel or whatever, it’s just gonna take them more time. And that is an evil and pernicious problem that is kind of baked into the model. And we just reject it wholeheartedly. Doesn’t mean we never make a mistake. But if your car shows up later than we estimated, it’s because we made a mistake, and we are trying over and over and over and over again to eliminate those — they’re defects — and then start to guarantee it over time.

BARRY RITHOLTZ (00:34:13):  So you are crunching a lot of numbers; you’re seeing a lot of data in real time. I’m kind of fascinated by the concept of what, at Lyft HQ, the dashboard looks like. What sort of data are you watching constantly? What’s the most surprising set of numbers or charts that come across that?

DAVID RISHER (00:34:34):  Yeah, this is a great question. I mean, so the answer, first — just to validate the premise — is: absolutely, an enormous amount of real-time data. You know, two to three million rides every single day, and now worldwide. So we’re very active, and in fact, we have whole cool maps that show simulations of behavior, particularly around storms and all sorts of crazy times. Anyway, back to your question. Look, there are a couple of metrics that I think might surprise you that we pay as much attention to as we do. And I’ll give you a very specific one, ’cause it kind of helps tell the story. When I joined, about 15% of the time, drivers would cancel on you. Now, this is infuriating.

BARRY RITHOLTZ (00:35:08):  Really? That high? I mean, every now and then on your competitor I’ll see a cancellation, but typically it’s rush hour. Someone’s stuck on the other side of the city; they’re not gonna make it. So rather than get that ding, they just cancel and find someone by them.

DAVID RISHER (00:35:24):  So in today’s world, it is less than 4.5% on our app. So we’ve brought it down by a factor of —

BARRY RITHOLTZ (00:35:31):  Three.

DAVID RISHER (00:35:31):  Yeah, exactly — slightly less than that, actually, but around that. So how have we done that? Well, it’s not just that they’re on the other side of town. It’s maybe we didn’t give them enough information right up front — so, for example, how much they’re gonna make, or what neighborhood they’re gonna drop you off in, maybe. And by “not enough information” — maybe we gave it to ’em, but the font was a little bit too small for them to see it. Right? Or maybe it wasn’t on the screen quite long enough. Or maybe we gave you a ride that we didn’t know was very, very unlikely for you to want, because of your past history or whatever. So now we spend a lot of energy — and we’ve just been grinding away this year, after year, after year, because it’s so infuriating to riders. That’s an example of a sort of specific metric that we’re looking at, you know, by the day.

BARRY RITHOLTZ (00:36:23):  Huh — really, really interesting. Two kind of related questions to the growth of Lyft. Your last quarter’s earnings call, you said — or maybe it was a previous one — 27% of North American rides are linked to a corporate partnership. Chase, DoorDash, United, Hilton, et cetera. What is that strategy? Is that about customer acquisition? Margin? Like, what goes into those sort of big partnerships?

DAVID RISHER (00:36:51):  Sure. So, you know, as you say, we have tens of millions of people who use our service every quarter — it’s about 50 million a year. And again, this is back to sort of the Amazon philosophy: you gotta compete for those customers, right? You gotta compete because, you know, they have alternatives. And in fact, there’s another company out there that some people know. Okay? So one of the ways you compete is you say, gosh, it’s not just about the ride — it’s about the relationship. And maybe it’s a relationship you already have with another company. So you mentioned United Airlines. United Airlines has now been a partner of ours for about the last six months. It’s been a wonderful partnership already, because the United Airlines MileagePlus program is incredibly well built out. People are very, very loyal to it. What can you do on Lyft? You can now earn miles so that you can take a vacation —

BARRY RITHOLTZ (00:37:38):  Same with Hilton Honors.

DAVID RISHER (00:37:39):  And same with Hilton Honors — exactly right there. We’ve been a partner for many, many years. The big innovation on the MileagePlus side is you can actually spend your miles on Lyft as well, which almost feels like free rides, right? That’s right — it’s just like, you get, you know, 200 miles or 500 miles, whatever, for taking an airline trip, and you spend a small segment of those on a Lyft ride. So these partnerships — you sort of asked what the method behind it is — it’s about customer acquisition, for sure, but it’s also about customer retention, you know? ‘Cause if you’re in the United ecosystem, or on the DoorDash side, or Hilton, or Alaska Airlines, or Chase — built primarily here in New York City and other cities where they’re active — and you want to either earn or burn miles or points, we’re a great place to do that.

BARRY RITHOLTZ (00:38:22):  Really, really kind of interesting. I read an article from Reuters: smaller US markets and college towns have been meaningful growth drivers. Curious why those markets were underpenetrated. What did you guys figure out there?

DAVID RISHER (00:38:37):  So part of it — there has been just a little bit of, you might say, neglect from the rideshare business for a while. And we realized about 18 months ago that a large part of the TAM — just to frame this again, total —

BARRY RITHOLTZ (00:38:51):  Addressable market.

DAVID RISHER (00:38:52):  Exactly — is more market. About 160 billion rides a year that people take in their private cars across the United States. 160 billion. And remember, we do a billion; the other guys might do three or four billion — maybe two or three billion. So four billion outta 160 billion. Okay? So there’s a lot of addressable market left for us to go to. And we’ve been in places like New York and San Francisco and Chicago for over a decade right now. But some of these smaller towns — the Indianapolises of the world, the St. Louises of the world — as well as college towns, where basically nobody has a car compared to the population, they just look like good opportunities for us. They’re complicated from a marketplace-management perspective, because anytime you go to a newer geography, you’ve got to first make sure you’ve got enough drivers, ’cause otherwise it takes too long to get picked up. And you’ve gotta make sure you’ve got enough riders, because if not, then drivers won’t make enough money. So it’s quite complex to —

BARRY RITHOLTZ (00:39:41):  Invest. There’s a chicken-and-egg problem there.

DAVID RISHER (00:39:43):  It is a chicken-and-egg problem, over and over again. Which, again, is why — back to the earlier part of the conversation — it’s really quite hard at this point to come into the market fresh. You know, you’re not gonna find a lot of folks who want to come into a well-served market. But anyway, so we just started to focus on it, and our data scientists and our marketers really kind of went to town, and it’s been a big source of growth.

BARRY RITHOLTZ (00:40:03):  Huh. Really, really interesting. Coming up: we continue our conversation with David Risher, CEO of Lyft, discussing the future of transportation technology. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

BARRY RITHOLTZ (00:40:31):  You are listening to Masters in Business on Bloomberg Radio. My extra special, fascinating guest is David Risher. He is the CEO of Lyft, and we have been discussing the future of transportation technology. We have to talk about AI; we have to talk about autonomous vehicles. But before we do, I have to ask you two really interesting questions. One is: how do you solve the problem of even sober people leaving their phones in the car when they get out? And suddenly it’s a big pain in the ass — somebody has to come either drop off the phone or whatever. How do you, as a customer-obsessed company, how do you solve that problem?

DAVID RISHER (00:41:16):  I so love this question, because it is an experience every single one of us has had, and it is both infuriating and incredibly stressful. Because all of a sudden you realize, oh my God, my entire life is driving in the wrong direction, and I don’t even know how to contact the company at this point.

BARRY RITHOLTZ (00:41:30):  Because the number is on your phone —

DAVID RISHER (00:41:33):  And the phone is in the car, and you’re like, I wanna hold my phone to call the phone — but I can’t do that. It’s very, very stressful. So here’s what we’ve done. We’re doing a huge amount of work on this, just to be really customer obsessed. The first thing is automatic detection. So if the phone starts to travel away with a driver after you’ve been dropped off, that immediately, automatically alerts the driver: there’s probably a phone in your backseat. It requires a little bit of work on the rider’s side — we’re still trying to figure out how to get riders to opt into this, because they have to share a little bit more information. But we’re still working on that. But regardless of whether it happens automatically or manually, the second thing is: we’ve got a whole web portal, so you don’t actually have to use your phone. You can — and you don’t have to log in. But really, the big innovation is this — we wanted to have it sort of out of band — so the whole “return the phone” thing becomes almost a separate process. And frankly, in the past, it’s almost felt like a bit of a negotiation with the driver, and nobody liked it. The drivers didn’t like it, ’cause it felt like it was sort of an annoyance. The riders didn’t like it, because they’re like, oh my God, I sort of feel like I’m being held hostage here. A terrible thing. Now it’s a whole automated process. And basically, what we realized is: we should just treat it like any other ride. So it’s basically — the phone is getting a ride back. So what you get to say as a rider is: yes, please bring my phone back. I know exactly how much it’s gonna cost — it’s gonna cost just the exact same amount as if I’d taken a ride to that exact place where the phone is. And the driver gets it in their queue just like they would get any other ride request. And it gets returned to you. Typically — I was just looking at this data, and it changes every single week — but we’re now getting to the point where a large percentage of riders’ phones are being delivered back within an hour, which is the absolute gold standard.

BARRY RITHOLTZ (00:43:09):  So let’s use technology and cut that: on the app, opt in to avoid leaving your phone in the car, via Bluetooth. Not on each ride — just once, on the app. And then when the ride is over — you’ve arrived and the person gets out — if the phone doesn’t leave the car, right there and then, the driver should lower the window and say, hey, you left your phone in the backseat. And that doesn’t seem like you’re changing or creating new technology. That’s right — you’re just applying existing technology. Why take an hour? Why not take 30 seconds?

DAVID RISHER (00:43:48):  A hundred percent. And this is now where you realize that all technology problems are ultimately human problems. Because in order for that to happen, a person has to have opted in — they’ve gotta click a button. Most people are either skeptical of that, or they’re not paying attention. So now our trick is to try to figure out a way to really encourage people to do that. As you say, you only have to do it once. But that’s gonna be the next big focus.

BARRY RITHOLTZ (00:44:09):  So let’s stay with that theme before we really move too far away from people and towards technology. You drive for Lyft every six weeks or so, which seems kind of bonkers. What have you learned sitting in that seat that you can’t learn from the executive suite or the boardroom?

DAVID RISHER (00:44:28):  So much. So much. And, you know, I know we’re all busy people — here I am, busy senior executive, CEO of a company. My God, you know what? I got time, right? I got time — I can jump in the car. And here’s why: I learned stuff about being a driver, and I learned something about being a rider, every single time. So I’ll give you an example of each. Very quickly, on the driver’s side, I learned how important a feature is that we’ve developed over years and refined, called Stay Within Area. And there are actually two features next to each other — one’s Stay Within Area, one’s Arrive On Time. Lemme actually focus on Arrive On Time. What that means is: I’ve got a kid to pick up at the end of the day, or I’ve got a date with my wife tonight, or I’ve got a doctor’s appointment at three o’clock in the afternoon. And so I need to figure out a way to organize my life such that my last ride is gonna put me, you know, right where I need to be by a certain time. If I look at the gig economy, one of the real gifts of the gig economy is it allows you to integrate your work into your life in new ways. Again, I don’t have to call my boss and tell ’em I’m gonna be late today. I don’t have to do anything like that. But sometimes I do have other things in my life. Maybe it’s another job; maybe it’s an obligation with my parents — or whatever it might be. So anyway, that’s a feature. It worked pretty well when I started. It works very well now — and in part, it’s because I give a lot of feedback to the team on how to make that better and how important it is to get that exactly right. And then on the rider’s side — I mean, every time I take a rider in the car, of course I ask them why they chose us versus the other guys. Sometimes it’s because they say, oh, Chase Sapphire Reserve — I’m a Chase Sapphire Reserve cardholder, and you guys have a relationship with them. That’s great. That gives me a little bit of data of how important that is.

BARRY RITHOLTZ (00:46:03):  That’s a points relationship.

DAVID RISHER (00:46:05):  It’s a points relationship — and you get all sorts of — you get $10 every single month to use as Lyft credit. And look, I can look at the data just like anyone else and realize the number of people who are using that. But there’s just no substitute for hearing somebody, you know, go off about how much they love that card, and how important that partnership is to them. That’s a generic example. And then a specific example involved a woman that I gave a ride to — this is now about almost two years ago, but it’s still really, you know, kind of resonates with me — where she would wake up every single morning, and depending on what the price was of getting from her home to her job — because the prices would bounce around a lot — she would either take a Lyft, or maybe take the other guys, or drive herself, or stay home. And it was a source of stress and concern to her every single day. She would literally wake up an hour, you know, before she had to leave, just to sort of check prices. And it just made me realize how much surge pricing is customer hostile.

BARRY RITHOLTZ (00:46:59):  Nobody likes it. Nobody likes it. It starts to drizzle a little bit, and suddenly it’s a $30 surcharge. And I know people are infuriated by it.

DAVID RISHER (00:47:07):  And they should be. And here’s the problem. This is the difference between — you know, if you’re an economist, you love this, right? It’s, oh, supply-demand balancing in real time — it’s just unbelievable. Like a perfect science experiment. And if you’re a real person, it just bugs the crap outta you. So it really drove home to me how frustrating this was. And it was literally a Friday morning where this woman had donuts, and she was bringing them in to see a coworker for his birthday. And she’s like, I can’t work from home today — I’m so glad that Lyft was reasonably priced. So that’s what’s led us to take about $50 million a year out of surge pricing. We’ve really tried to get rid of it as much as we can — can’t completely eliminate it — and also introduce a product called Price Lock that allows you to lock in a price on a route.

BARRY RITHOLTZ (00:47:47):  So tell us a little bit about Price Lock. What does that do? I’m not familiar with that aspect of the app.

DAVID RISHER (00:47:54):  Yep. So it’s really meant for people who commute the same route every day, and they don’t want the route to go from 20 to 30 to 40 bucks ’cause, you know, say it rained. And by the way, to be very clear, there are good reasons for surge pricing, right? It’s a very good way for us to encourage drivers to drive when there’s more demand than their supply. But because it’s very frustrating for riders, we wanna give people a way to kind of opt out of it. So for a given route — you know, from point A to point B — if you wanna lock in a price, we basically say, here’s the average price over the course of a month. If you wanna lock in, I think it costs $4.99 a month per route. That’s all it takes. And it’s been super popular for people who just want to get that outta their lives.

BARRY RITHOLTZ (00:48:28):  Huh. Really, really kind of interesting. So let’s talk a little bit about autonomous driving. I was in San Francisco last month — Waymos everywhere. Tell us a little bit about what Lyft wants to do with autonomous vehicles. Are these just shiny objects, or are these the future?

DAVID RISHER (00:48:48):  They’re the future. They’re the future. It will take a long time for this future to come; it will be very unevenly distributed. But they are the future. And the basic reason why is: they are a reliable product, and they’re a safe product —

BARRY RITHOLTZ (00:49:01):  Safer than human drivers.

DAVID RISHER (00:49:04):  They are, substantially. And it’s because they not only know the policies, but they follow the policies. You know, they tend to follow the rules, and they don’t get distracted. So, not to say some crazy thing won’t happen one time out of a million, but 99.999% of the time, they’ll do the thing that you expect a car to do — which is keep its rider safe. So, okay — so that is coming. So now, as a business person, you have a choice to make, right? You can either embrace this, or you can sort of not. And the thing is, in a sense it’s a choice, but in another sense it’s not, because you’ve seen Kodak and, whatever, Polaroid —

BARRY RITHOLTZ (00:49:40):  Who, by the way — Kodak invented the digital camera, but didn’t want to cannibalize their own film business. And how did that work out?

DAVID RISHER (00:49:46):  Not exactly — not so well. And then, on the other hand, you look at maybe a company like Netflix, that invented the DVD-by-mail business to sort of set Blockbuster aside, but did such a good job surfing from that to streaming, and now to original content, right? They’re a great company in so many ways, but they were relentless, fearless about cannibalizing their own business to get to the next thing. So that’s the shift that we’re right in the early, early, early days of. It will be another platform shift. But we’re in a very fortunate position, and here’s why. You know, we have millions of riders. We have millions of — billions, billions of data points about pickup and drop-off location and pricing and so forth and so on. And we have a whole subsidiary called Flexdrive that does fleet management, which I can come back to in a couple of seconds. But these are gonna be some of the building blocks of the self-driving — or, I really should say, hybrid — network of the future. ‘Cause that’s the last thing I’ll say, just as sort of intro: self-driving cars are gonna come little by little by little. Human drivers are gonna be around for a long, long, long time. There are not enough self-driving cars in any given market to satisfy peak demand on, you know, Friday afternoon at five o’clock rush hour, or what have you.

BARRY RITHOLTZ (00:51:01):  So this is not a three-, four-, five-year transition. This is a 10-to-20-year transition. Is that about right?

DAVID RISHER (00:51:07):  Think about it as a decade transition. Yeah. And even, again, the word “transition,” I think, is maybe not quite right, because the economics of an expensive car don’t really lend themselves to having a whole bunch of them sitting around at two in the morning, empty. You really, I think, want a hybrid network for a long, long time — for human reasons, too, right? You might want someone to help you with your luggage, or maybe even someone to ask you how your day was. But the economics of it make it such that it’s much more likely this will be a hybrid network for at least a decade or, you know, more.

BARRY RITHOLTZ (00:51:37):  So that kind of raises an interesting question: what exactly is Lyft? We know it’s a ride-hailing company; it’s also a transportation market-clearing mechanism. It’s a consumer brand, and it’s also a logistics platform. Like, where is the future growth coming from?

DAVID RISHER (00:51:56):  I mean, you know, a little — all of the above, right? So, as you say, the thing people know Lyft the most for are, you know, human-driven cars picking you up and dropping you off. And as we were just saying, that will become a mix of human-driven and, you know, frankly, robot-driven cars. What you may not know is Lyft also runs the bike share system here in New York City.

BARRY RITHOLTZ (00:52:15):  Citi Bikes are run by Lyft? I did not know that.

DAVID RISHER (00:52:18):  That’s exactly right. So we run Citi Bike, we run the program in San Francisco, we run the program in Chicago, we run the program in Boston, we’re in Portland, Oregon. And then we also supply the technology and the bikes in London, in Barcelona, in Madrid — you know, many, many countries around the world. This may seem like sort of a small thing, but if you’ve been to a city like New York or London, you’ll know that cities are very, very aware that they want sort of multimodal transportation. So that’s gonna be, you know, a big part of our future as well. And then, look — someday, who knows, maybe boats, maybe vertical-takeoff aircraft. Who knows? But I will tell you that our real focus right now — and we will always be — this is our sort of purpose: serving and connecting. I want people to be out and about, and connect with each other in any possible way we can. That’s really what I want.

BARRY RITHOLTZ (00:53:05):  So you mentioned London. What are the plans for Baidu robotaxis in London? Is this gonna be a pilot program that could potentially scale up dramatically, like the Waymos in San Francisco?

DAVID RISHER (00:53:21):  That’s right. So again, let’s think about the self-driving car world for a couple of minutes. The technology is being developed worldwide. It’s being developed in the United States — Waymo, of course, is the leader, really the worldwide leader. Zoox, which is owned by Amazon, is much, much smaller, but, you know, trying very hard to come up behind Waymo. And then there’ll be, you know, many others, including maybe Nvidia, and companies that aren’t even really in the space now but will wanna sell their technology to different OEMs — to different, you know, car manufacturers. There’s also technology coming out of China. Baidu is sort of the Google — you think of it as kind of the Alphabet — of China. And there are many, many others. There’s a company called WeRide, there’s a company called Pony, there’s a company called Momenta, there’s a company called Geely. I was just in China a couple of weeks ago, looking at the incredible just growth of technology there — both, again, kind of hardware and software type technology. Okay? So that’s all background. It’s gonna be deployed worldwide. And in the United States, Chinese technology is not super welcome, for obvious reasons. But Europe is taking maybe a little bit of a more sort of economical approach, where they’re kind of looking at different technology providers and saying, let’s experiment. So in London, we’re partners with Baidu. Baidu has a very, very highly regarded self-driving platform, and we’re just in the early days of rolling it out there. It’s called an RT6 car. This is sort of behind-the-scenes stuff — it literally is just rolling off boats right now, and it’ll be commercialized next year.

BARRY RITHOLTZ (00:54:48):  So I’m looking at the current crop of autonomous vehicles, which are essentially converted traditional cars. But do you really need that front driver’s seat? Can you change up the internal layout? Like, what are autonomous vehicles gonna look like — not in 2060, but in a couple of years?

DAVID RISHER (00:55:11):  So again, it’s such an interesting time to be in this industry, and it’s exactly as you’re saying — like, do you really need a steering wheel? Do you really need, you know, an accelerator and brakes? Zoox, as I say — they’re an Amazon subsidiary — they would say you absolutely don’t. And they have a purpose-built vehicle that doesn’t have either one of those things. Now, for regulatory reasons, for human-acceptance reasons and so forth, for manufacturing reasons, that’s gonna be slower to roll out, because you can’t rely on, you know, the big OEMs to produce a car like that. That’s — it’s its own vehicle. So I think what you’re gonna see over the next three to five years is an enormous amount of new innovation in the car space. It won’t just be, you know, there won’t be a driver. It’ll be — you’ll have seats that face each other. You know, you’ll have seats that completely recline, ’cause you’ve got more space in there. You’ll have different luggage configurations. You’ll have — you know, some of them will feel more like, you know, party buses. Some of them may be, you know, corporate shuttles that just don’t have drivers. A lot of new stuff is gonna come in the next couple of years, step by step, because, again, you know, hardware is hard. It takes a long time to build it out. But, you know, you look five years out, and I think you’re gonna see a lot of cars that look pretty different from what you see today.

BARRY RITHOLTZ (00:56:16):  I’m unfamiliar with Zoox and Amazon’s relationship with them. But if I recall correctly, Amazon was an early investor — took a big chunk of Rivian. That’s right. And all of the electric Amazon delivery vehicles you see are essentially the Rivian platform repurposed for commercial use. Is Zoox plus Rivian the direction Amazon is going? And do you guys — does Lyft, whose CEO has a relationship with Jeff, have a relationship with Amazon?

DAVID RISHER (00:56:49):  We do have a relationship with Amazon. Of course, we’re huge consumers of AWS, which is Andy’s — the current CEO’s — kind of pride and joy. And for sure we’ll end up using — look, everyone is gonna end up partnering with everyone. That’s the interesting space we’re in right now: if you’re in the business of developing a self-driving car, it’s billions of dollars of R&D — billions of dollars. And so you want as many customers as possible. And then, if you’re in our business — in the business of moving people around and connecting people — you wanna have multiple suppliers of that technology, so you’re not beholden to anyone. Some of that is just being, you know, a smart business person. But some of it also is: technology goes through its own, you know, fits and starts. Look at what happens with the airline business when, all of a sudden, you know, Boeing has a problem with one of its units. You know, they stop manufacturing those for a time, or they’re grounded. So I don’t wanna overdramatize, but, you know, anytime new technology comes out, you’re gonna find some of that happens as well. So all of us are kind of in multiple — you know, let’s say maybe polyamorous relationships might be one way to —

BARRY RITHOLTZ (00:57:53):  Well, don’t you have to be? You can’t lock into platform dependency too early — otherwise you end up owning Betamax, and what good is that? And I know half our audience has no idea what the hell that —

DAVID RISHER (00:58:05):  Is. There we go. An old —

BARRY RITHOLTZ (00:58:06):  School reference, yeah, right. But I mean, when you commit one way — so let’s talk a little more about the autonomous ride hailing. What are the big concerns? Is it safety? Is it regulation? Is it winning the consumer’s trust? What are the economics of managing a fleet like that?

DAVID RISHER (00:58:25):  Again, so many interesting questions here. Let’s start with the customer side of things, right? So the first order of business has to be building customer trust and adoption for this new technology. Because, you know, it’s a car that drives itself, which is magical, but also can be a bit intimidating or, you know, even scary for people who haven’t seen the technology. Lyft obviously has a lot of value to add right there, because it’s a brand that people already trust; they understand you’ll be able to opt in or opt out of getting it. I was just in Atlanta a couple of weeks ago, where we have an experiment — a small deployment — with a company called May Mobility, which is also in the self-driving car space. They’re Toyota Siennas. They pull up to you, and all of a sudden you get in — it’s kind of a whole different type of experience from what you’ve probably experienced in the past. But because it’s got Lyft behind it, right on the door already, people sort of say, okay, great — I kind of understand this company and know something about it. Okay, that’s great. So then you kind of have to work yourself down the stack. There are all sorts of technology problems that you have to solve as you integrate, you know, their platform and us. And then someone’s gotta manage these cars. And this is worth talking about for a couple seconds. In traditional rideshare, the driver is responsible for their own car, right? They put gas in it, or they charge it up if it’s electric; they keep it clean; hopefully they keep it maintained, and so forth. But in the self-driving space, at least for the next three to five years, most of the car owners are gonna be professional fleet owners. You know, they’re gonna buy 20, 50, a hundred, 500, and are gonna kind of manage these as a fleet. And that means that they’ve gotta be, again, charged and maintained and cleaned — but they have to be done kind of at a professional level. That’s the sort of stage we’re in. We’ve had a subsidiary for many years called Flexdrive. We actually own about 10,000 cars on the Lyft platform for drivers who don’t wanna drive their own car. And we are responsible for maintenance and keeping them cleaned and so forth and so on. So we actually bring a lot to that as well. And I think that’s one of the reasons why we like the economic profile of self-driving cars. They don’t have insurance as high, for example, as personally driven cars. But also, we like the economics of our fleet-management subsidiary, and think we can service these at an industry-leading rate, and therefore, hopefully, make more money on the asset than anybody else.

BARRY RITHOLTZ (01:00:32):  Is there still gonna be a future for people who — today, you would think of owner-drivers — who just wanna own autonomous vehicles and lease ’em out, or send them out into the Lyft network? Like, I’m crunching the numbers in my head as we’re speaking, and I’m like, oh, that could be a 10, 12% return on investment. Not bad when bond yields are 4%, three and a half percent.

DAVID RISHER (01:00:56):  A hundred percent. I mean, there will be a time where, you know, if you fast-forward, you know, five years or whatever, maybe more, many people — individual owners — have cars that can drive themselves. And then there’s a question, to your point, of, you know, can  you put that on the network? The answer is: absolutely, you’ll be able to put it on the Lyft network, and it’ll come back again cleaned and charged, because of the fleet-management side of things.

BARRY RITHOLTZ (01:01:14):  Huh — that sounds really, really interesting. You know, it’s funny, ’cause when the ride apps first came out, there was a little bit of a lag before people got comfortable. What do you mean, I’m getting into a stranger’s car? I imagine we’re gonna go through the same thing — what do you mean, I’m getting into a car with no driver? It feels like the transitions are happening faster and faster. Same sort of question: this isn’t a 10-, 20-year thing; this is a couple of years before people — forget people under 30, who adapt so rapidly — the middle part of that age bell curve, the 30-to-60s, they’re gonna adapt to this pretty quickly over the next couple of years. How do you think about the different segments of consumer when it comes to autonomous driving?

DAVID RISHER (01:02:04):  Yeah. You know, I think, as you’re suggesting, younger people do tend to take up new technology, you know, pretty quickly. But in this case, I do believe that many people, after they’ve had a couple of rides and realize that it feels very safe and reliable, I think they’ll flip from skeptic to kind of fans, you know, pretty quickly. Now, I will say policymakers, you know, they have their own, you know, issues — and some of that can be very local. So you may find some cities that just say, we just don’t want ’em on our streets for a period of time. You may find, conversely, other cities that say, bring them, ’cause we wanna feel like a city of the future. So I think there are gonna be some policy issues. There are also some infrastructure issues. Remember that, you know, AVs also tend to be EVs. EVs require charging; charging requires infrastructure. And not every city’s gonna have the amount of, you know, electrical power. I mean, this is kind of a side issue, but if you listen to, you know, Jensen, for example, at Nvidia, talk about what could end up holding the United States back from its next big leap — a lot of it comes down to power infrastructure in this country, right? So anyway, there are many different kind of bits and pieces, all the way from consumer adoption to physical infrastructure to policy and so forth. But I think, again, over the next three to five years, I think you’re gonna see a real shift — mostly because consumers are gonna try them and like them, and then they’re gonna be saying, hey, you know, faster, please.

BARRY RITHOLTZ (01:03:17):  So here’s the crazy thing about AVs that I’m still kind of shocked about: it relies on visual, on lidar, on radar, and all these other technologies, but there isn’t a whole lot of infrastructure built into the roadway grid. Wouldn’t be that difficult to create a series of RF devices that are specifically geared for autonomous vehicles — that, like, every now and then, if you’re letting the car drive yourself and there’s an exit or a merge — like, it’s not great with those sort of things today, because there’s no real infrastructure. It’s relying on a technology not built for autonomous driving. Is there any sort of motion towards, hey, let’s everybody that’s doing autonomous come up with a set of standards and have the government implement this into the highway system?

DAVID RISHER (01:04:16):  I mean, the short answer is no today — and long-term, for sure. And the reason no today, frankly, is, again, you know, anytime you see these platform shifts, you always have competition for sort of who gets to own the platform, right? And individual companies all have a huge incentive to say, you know, I wanna do it my way. ‘Cause if my way becomes the standard, then everyone else kind of follows along me, and I get to sort of set the standard. Over time, though, you tend to see that those things — that doesn’t become a long-term competitive advantage, typically — particularly for this sort of infrastructure. And so I would fully expect, over time, just in the same way that you can start to see charging networks kind of harmonize, that you’ll see some sort of, you know, kind of federal level. But we’re years before that.

BARRY RITHOLTZ (01:04:59):  Right. We did see that sort of standardization take place in a lot of other technologies. And suddenly you’re not competing on a standard; you’re competing on highest quality, lowest price, et cetera.

DAVID RISHER (01:05:08):  That’s exactly right.

BARRY RITHOLTZ (01:05:10):  But you would think that if the cars literally knew exactly where the road was, it would be even that much safer.

DAVID RISHER (01:05:19):  You would think. But I would say, right now, the technology is evolving so quickly at the car level, and really, the safety is very, very, very impressive. And of course, look — I know, you know, tomorrow morning you’re gonna open up, you know, a newspaper or an app, and you’re gonna read about some strange thing that happened, you know, in some strange part of the world, with a self-driving car. And I’m gonna tell you that that is gonna happen — and that’s, you know, one in a million, as opposed to, you know, one in hundreds, which happen every single day with human drivers.

BARRY RITHOLTZ (01:05:49):  Yeah — those are the clickbait headlines, not the statistically significant practice. All right, so last question before I get to my favorite questions I ask all my guests. When it comes to transportation technology, what are we not discussing as a society, as a government, as consumers, that we really should be? What is kind of getting overlooked in this rush to new technology? It could even be something that you guys are focused on, but a lot of people don’t realize — oh no, this is really significant, and the public hasn’t quite grokked this yet.

DAVID RISHER (01:06:24):  You know, I’m gonna come back to the basic role that technology plays in people’s lives, to help them live their absolute best lives. I’ll tell you something that I’m a lot passionate about personally. And that is: as people live longer lives, one of the things that is very predictive of their quality of life is how much time they’re spending with other people, out and about, socializing.

BARRY RITHOLTZ (01:06:44):  Socializing.

DAVID RISHER (01:06:45):  Exactly. Very, very highly predictive of a healthy, long life. And as we as a country are getting older — which we are, demographically — that is gonna be an enormous shift, where you have so many more people in their sixties, seventies, even eighties, who wanna live healthy, vibrant lives. And so one of the things I’m really quite proud of with Lyft is, you know, Lyft Silver — a particular product line that we’ve developed over the last year that’s really focused on, you know, helping older folks get out. The apps are easier to use, the cars are easier to get into, the driver’s a little bit more experienced. I think that sort of intersection between societal trend and the type of work we do in transportation is really quite deep. And, you know, maybe just as important, ultimately, is, you know, all of our conversation around medicine and so forth and so on is: keeping people out and about. And I know — here in Oura Ring world, where I am as well — or maybe you’re not, I don’t know.

BARRY RITHOLTZ (01:07:37):  I am — my wife wanted to get one, so we got a pair. And she got bored being told she’s stressed all the time and stopped wearing it. So now I’m wearing it. So we both — we each have one, and I’m the only one who still wears it. How funny.

DAVID RISHER (01:07:48):  Okay — actually, my wife and I did the same. She said, I get a little tired of seeing, you know, that it’s telling me exactly I’m stressed or I’m not sleeping well. But at least for me, it’s a sort of nice nudge to get good sleep, and, frankly, to kind of keep an active life. And so I see this space — the transportation piece — as somewhat similar. Like, I want technology that kind of helps me live my best life. And I think transportation plays a big role there.

BARRY RITHOLTZ (01:08:07):  All right, so let’s jump to our speed round — our favorite questions. Starting with: tell us about your mentors who helped shape your career.

DAVID RISHER (01:08:16):  Oh gosh, I love this question, ’cause I think it’s so important for us to remember that we all stand on other people’s shoulders. I’ll list a few. Of course, I worked for Jeff Bezos a lot — I’ve mentioned him. But I wanna mention other people. First big boss: a guy named Todd Nielsen. Todd really taught me the power of a great story, and also the importance of really listening to and watching customers closely. So he taught me two big things there. And then a guy named Peter Spiro — he was the board chair at Worldreader for many years. He and I sort of knew each other back in the Microsoft days, but he was the board chair for the nonprofit I ran. So focused on the team, so focused on the team — you’re only as good as your team. Really learned a ton about management and leadership from Peter.

BARRY RITHOLTZ (01:08:57):  Huh — really interesting. Let’s talk about books. What are some of your favorites, and what are you reading currently?

DAVID RISHER (01:09:02):  Oh man. I just finished a book called Good People. So I tend to read some fiction and some nonfiction. I’m currently reading a book called Apple in China — all about Apple’s entrance into China, and ultimately the importance that China has, and, frankly, the power that China now has, over Apple. And then Good People is a fictional book about an Afghan family from Afghanistan that moves to the United States, and is either a model family or terrible people. And it’s very, very hard to know which — the book sort of flips back and forth. Remember when I said that books kind of teach empathy and sort of different perspectives? This one does a good job of that.

BARRY RITHOLTZ (01:09:42):  Huh, really interesting. What about streaming? You listen to any podcasts, or Netflix, Amazon, whatever? What keeps you entertained?

DAVID RISHER (01:09:50):  I do. I am a podcast guy. I have to say, though, I’m kind of traditional when it comes to podcasts. I listen to The Daily from The New York Times pretty regularly. And I think most of it is because I have so many things in my life that are sort of — there’s so much content that comes at you that’s sort of superficial. And at least with The Daily, I feel like I get to go a little deeper on a subject. You know, it tends to be a kind of half-an-hour deep dive on a particular thing. And I do feel — particularly, I also read The New York Times; I know it’s sort of traditional in that way. So if I’ve read an article, and then I kind of hear a podcast on the same topic, I do feel like I’ve actually gotten maybe a little bit smarter about something, you know, beyond the surface.

BARRY RITHOLTZ (01:10:28):  Let me just push back ever so slightly, please, on how The Daily has evolved. Because when it first came out — and I was a regular listener — I don’t want anybody telling me about the story that’s in the paper that I can read. They used to kind of do the background: hey, how did you start investigating this? What led to this? Tell us some interesting stuff that didn’t make it into the article. It was really inside baseball, and that stuff is kind of fascinating. Now, whenever I check it out, it’s the person — I don’t wanna say reading the story, but it feels like they’ve left a lot of that, you know, behind-the-scenes stuff back three years ago. It’s still — it’s become one of the biggest podcasts in the world. It’s giant.

DAVID RISHER (01:11:13):  Yeah. Yeah. That’s interesting.

BARRY RITHOLTZ (01:11:15):  Anything else? Anything else you listen to or watch?

DAVID RISHER (01:11:19):  I mean, you know — mindless TV I love, but I’m not gonna embarrass myself and tell you all that sort of stuff. Yeah, we’ll stick with The Daily on this one.

BARRY RITHOLTZ (01:11:27):  We are in the golden age of mindless TV, for sure. And it’s not — you know, if you are watching The Crown, or Landman, or 3 Body Problem — there’s so many fascinating shows out there. It’s not like garbage time like it was when I was a kid.

DAVID RISHER (01:11:43):  You are right about that. And I will say that my wife and I became obsessed with The Pitt, as many people are. It is funny — and it almost makes you feel like, you know, I’m, like, halfway to being an ER doc myself. By the way, you are not — so don’t think that that’s true. But what is hilarious is my wife’s tolerance for some of the gory stuff is a little lower than mine. So she watches The Pitt with her hand kind of half in front of her face the whole time.

BARRY RITHOLTZ (01:12:04):  My wife — we watched the first couple episodes. She’s like, this is just too much. It’s like — you wanna relax? And it’s very serious. I just kind of tense out.

DAVID RISHER (01:12:11):  Yeah. But it’s a great cast, and it’s a great set of stories, for sure.

BARRY RITHOLTZ (01:12:16):  Final two questions. What sort of advice would you give to a recent college grad interested in a career in either technology or business?

DAVID RISHER (01:12:25):  So my advice here tends to be — it’s always sort of the same. And here’s how it goes. There’s so much temptation when you’re picking your job early on to pick something that sort of seems like it’s gonna be good on your resume, or maybe it’s gonna make you a lot of money — whatever it is. This is sort of the temptation, ’cause it’s so sort of in the air, maybe now more than ever, because of social media. And, oh man — the people that I see succeed are really the ones that say: yes, I have an economic reality; I have to sort of do better than that. But once the economic reality has been met, it is all about: pick something you think you’re really gonna love and are gonna be good at. And I say that like — you have to be a bit introspective of this. You know, maybe you love, you know, selling. Okay, great — so take a sales job. Maybe you love listening to customers — great, take maybe a marketing job. Maybe — but I’m trying to make this sound maybe a little bit more interesting than “follow your passions,” ’cause that’s so trite. But there is something to it: really kind of being introspective about what you think you’re gonna just jump outta bed every morning and love doing tends to be a much more powerful predictor of long-term success than people who try to optimize for that short-term, sort of get-rich-quick type of thing — and then find themselves later realizing, shoot, this isn’t really my thing. It’s somebody else’s thing.

BARRY RITHOLTZ (01:13:39):  Really, really good answer. And our final question: what do you know about the world of consumer-facing technology and apps today that would’ve been useful to know 25, 30 years ago, when you were first getting started?

DAVID RISHER (01:13:53):  Wow. Okay. That’s also a really interesting question. You know, I think I’ve probably gone through a similar arc to other people, where in the nineties — maybe even early two-thousands — I was sort of a universal techno-optimist. I probably was in the camp that said technology is such a powerful force for the good. And you see me try to, you know, harness it with Worldreader, specifically — of course, trying to take technology and get people reading. In that case, it did work. We’ve gotten, you know, over 22 million people reading. So that’s awesome. But, oh man, it is hard not to see some of the just terrible costs we’ve paid as a society. And so I think — maybe more of a mindset than a particular thing — of just: be really aware that technology is so powerful, and, man, with great power comes great responsibility. And I’m just a big believer that our best leaders now — and I’m not necessarily putting myself in the category — are being really thoughtful about, you know, the good of technology, but also really trying to avoid some of the problems.

BARRY RITHOLTZ (01:14:53):  Good, good answer. David, thank you for being so generous with your time. This has been absolutely fascinating. We have been speaking with David Risher. He is the CEO of Lyft, one of North America’s largest ride-sharing networks. If you enjoy this conversation, well, be sure and check out any of the 639 we’ve done over the past 12 years. You can find those at iTunes, Spotify, YouTube, Bloomberg — wherever you find your favorite podcasts. I would be remiss if I did not thank the crack team that helps me put these conversations together each week: Alexis Noriega is my video and podcast producer, Sean Russo is my researcher, Anna Luke is my producer. I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.

 

 

~~~

 

 

 

The post MiB: Lyft CEO David Risher appeared first on The Big Picture.

10 Wednesday AM Reads

My mid-week morning reads:

The 20 highest-paying jobs in America? Doctors, doctors, more doctors. Doctors earn more than any other broad category of worker, according to federal data: More than engineers. More than computer scientists. More, even, than lawyers. To find a better-paid group than doctors, economists say, you have to drill down to elite subcategories, such as corporate CEOs and law partners. The average partner at a large firm earns more than $1.4 million a year. The typical S&P 500 CEO pulled down $17 million in 2024. Med school remains the trade of kings. (USA Today)

• This Will Have Been a Golden Age for Investors: Kyla Scanlon makes the case that we’re living through an extraordinary period for capital markets—and most people are too anxious to notice. (Kyla Scanlon) see also Active vs. Passive Fund Performance: When Do Active Managers Win? While passive funds dominated in 2025, strong active investing opportunities still exist. (Morningstar)

Chevy built an all-American EV truck — why is nobody buying it? The Silverado EV drives, well, almost like a car. Yet the bed is massive, its frunk, cavernous. The back seat has enough room for me to cross my cursedly long legs, and the cabin is quiet. It’ll power your house in case of a hurricane, and it’ll haul, tow, and navigate down the freeway without a finger on the steering wheel. Plus it travels over 400 miles on a charge. That should be a dream combination for an American pickup lover. What happens when product, price, and politics collide. (TechCrunch)

• About Those High Egg Prices (The Washington Monthly Was Right):  Much of the press believed The 2022-25 spike in egg prices was mere supply and demand. Now that the industry has settled with DOJ and state AGs, our suspicions proved warranted.  that dominant egg corporations may be manipulating a price index tied to most commercial egg contracts. On Monday, the Department of Justice and a group of bipartisan state attorneys general agreed. They concluded a months-long investigation into companies like Cal-Maine, alleging that these corporations colluded to exploit the bird flu crisis and drive up egg prices, cheating consumers. Cal-Maine, Hickman’s Egg Ranch, and Versova will donate 53 million eggs to food banks and pay up to $3.3 million to state attorneys general. (Washington Monthly)

Always-On AI Is Coming: Quiet, My Exoself : Someday real soon, most of us — starting with young adults — will carry an always-on AI. This agent will help us navigate our journeys, answer our questions, tutor and teach us new skills, remember people we have met before, remind us of what we once knew before, offer advice and recommendations, do simple errands, and remember everything we say and do. Before long, it will know us better than we know ourselves. It will be our exoself. Kevin Kelly on quieting the exoself — the digital shadow that follows us everywhere and won’t shut up. (Kevin Kelly)

This little blue dot on your phone is revolutionary: U.S. policy used to jam up GPS. Now, those signals beam into your pocket. WaPo on the little blue dot: GPS on your phone is quietly one of the most revolutionary technologies ever shipped. (Washington Post)

What’s inside the one bill Trump most desperately wants to become law: A sweeping set of national requirements for voters. An empowered DHS. What would happen if the SAVE America Act passed? (Vox) see also Supreme Court’s dramatic moves will reshape elections — and give the GOP a midterm boost: The timing and speed of the justices’ moves are all but unprecedented in recent years, legal experts said. Republicans are expected to reap the most rewards. WaPo on the Supreme Court’s election-law rulings and how they tilt the midterm map toward one party. Structural advantages compound. (Washington Post)

As the Pentagon stays quiet, AP reconstructs a US strike that killed over 100 Iranian children: The Feb. 28 attack on a primary school in southeastern Iran was the deadliest reported strike in the U.S.-Israeli war against Iran (Washington Post)

Six Years After the First COVID-19 mRNA Vaccines, Billions of Doses Clarify Their Protection and Rare Risks: Learn how mRNA vaccines work, why serious risks remain rare, and how the technology could be used beyond COVID-19. (Discover) see also CDC Won’t Publish Report Showing COVID Shots Cut Likelihood of Hospital Visits: A CDC report on vaccine effectiveness, previously delayed by agency leadership, is now being blocked from publication entirely. (Washington Post)

The United States’ dream didn’t die. It was overturned: The red card wasn’t overturned; that would have required admitting an error. The suspension was put on suspension, through the magic of a clause buried in the organization’s disciplinary code. Initially, FIFA announced the decision in such a skeletal manner that the world knew it was hiding a body. On match day, Trump stood before reporters at the White House, and after trying to deflect his role, he talked until it was clear that he applied pressure. The Athletic on the U.S. World Cup exit to Belgium — the dream didn’t die, it was overturned. (The Athletic)

Video of the day: Mystery Billionaire Builds $425 Million Estate in Hamptons.

 

Be sure to check out our bonus episode of Master’s in Business with David Risher, CEO of Lyft, one of North America’s largest ride-sharing networks. He joined Lyft’s board in 2021 when the firm was burning cash and losing ground to Uber. Lyft has returned to profitability, with its stock rising more than 75% since Risher took the reins as CEO in 2023. In Q1 2026, the firm had 28.3 million active riders and did $4.9B in gross bookings, with $1.7B revs, and $132.8m in EBITDA. Previously, he held senior roles at Microsoft and Amazon.

 

America at 50, 100, 150, 200 & 250

Source: Bruce Melhman

 

Sign up for our reads-only mailing list here.

 

The post 10 Wednesday AM Reads appeared first on The Big Picture.

10 Tuesday AM Reads

My Two-for-Tuesday reads:

•  Are Humanoid Robots Ready to Be Deployed?: The New Yorker asks whether humanoid robots are actually ready for real work. The demos are dazzling; the deployment numbers, less so. (The New Yorker)

Why Small-Cap Stocks Are Beating the S&P 500: The long-suffering small caps finally have a moment, and Barron’s names the vehicles. A rotation worth watching after years of mega-cap dominance. (Barron’s)

• A Viral NYT Story Says Remote Work Makes Us Depressed. It’s Wrong.: The Times ran a splashy piece linking remote work to depression. The methodology doesn’t hold up. A careful debunking of a story that confirmed what bosses wanted to hear. (Two Percent)

Michael Saylor’s Strategy Is Trapped by Its Own Broken Bitcoin Math: The bitcoin hoarder created a bespoke valuation metric that ignores market realities. The WSJ digs into the circular logic of Strategy’s (née MicroStrategy’s) Bitcoin treasury model. The math only works if the price keeps going up. Guess what? (Wall Street Journal)

Nearly a Million Investors Lost a Total of $3.8 Billion on Trump Crypto Coin: A report from a cryptocurrency analytics firm details how those who bought the Trump memecoin have fared, with most retail investors having lost money while sophisticated traders did better. The memecoin math: the house wins, the fans don’t. It’s the same lopsided ledger. (New York Times) see also Trump Made $1 Billion on Crypto Deals While His Fans Lost a Fortune: Roughly two-thirds of investors in the president’s memecoin are currently in the red. The WSJ tallies the billion-dollar haul against the supporters left holding the bag. Same story, more zeros. (Wall Street Journal)

The covert U.S.-China battle to make chatbots leak their secrets: American tech firms say rivals are forcing their chatbots to act as tutors to make Chinese AI smarter. (Washington Post)

When The Machines Deserve Our Consideration: We will never know for sure if AI can be conscious. A neuroscientist argues that we shouldn’t wait for proof to decide how to treat it. (Noema)

Why It All Makes Sense: The Psychology and Sociology Behind What We’re Watching. This isn’t the article that tells you something is wrong. You already know that. This is the one that tells you why it isn’t crazy…why the leader’s behavior…the follower’s certainty…the lie that won’t die…no matter how many times you correct it, all of it is documented…studied…and predictable. Not a glitch. A pattern. And patterns…can be recognized before they finish playing out. That’s not a small thing to gatekeep behind a subscription.  (Jack Hopkins Now)

•  Good News! Turns Out the Earth Will Never Be Swallowed by the Sun: Wired with some long-horizon good news: the Earth will never be swallowed by the Sun. Everything else this week, less reassuring. (Wired)

At 82, Keith Richards Isn’t Done Yet: ‘If It’s a Matter of Energy, We’ve Got It’ The rock legend isn’t ruling out a tour next year. (Wall Street Journal)

Video of the day: Why nobody uses Snapchat anymore

Be sure to check out our Master’s in Business with Mamoon Hamid, partner at Kleiner Perkins. He is a leading investor in enterprise-software and AI. He was an early investor in Slack, Figma, Rippling, Glean, Netskope, and Box. Hamid co-founded Social Capital with Chamath Palihapitiyal. In 2017, joined Kleiner Perkins

 

America at 50, 100, 150, 200 & 250

Source: Bruce Melhman

 

Sign up for our reads-only mailing list here.

 

The post 10 Tuesday AM Reads appeared first on The Big Picture.

Transcript: Mamoon Hamid, Kleiner Perkins

 

 

 

The transcript from this week’s, MiB: Mamoon Hamid, Kleiner Perkins on AI Investing, is below.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube (video), YouTube (audio), and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

 

~~~

 

Masters in Business: Mamoon Hamid, Kleiner Perkins

Host: Barry Ritholtz  ·  Guest: Mamoon Hamid, Partner, Kleiner Perkins  ·  Bloomberg Radio

Announcer (00:00:02): Bloomberg Audio Studios. Podcasts, radio, news.

Barry Ritholtz (00:00:08): This week on the podcast, another banger. Mamoon Hamid is partner at Kleiner Perkins, where he’s been focusing on early-stage AI investments for nine years. He’s got a fascinating background — early investor in Slack, Figma, Glean, Box, et cetera. Previously, he co-founded Social Capital with Chamath and worked for a number of other venture firms, including US Venture Partners. I thought this conversation was fascinating and I think you will also. With no further ado, my conversation with Kleiner Perkins’ Mamoon Hamid. Mamoon Hamid, welcome to Bloomberg.

Mamoon Hamid (00:00:57): Thank you so much for having me, Barry.

Barry Ritholtz (00:01:00): So I’m fascinated by your background. You grow up in Frankfurt, Germany. You come to the US to go to college at Purdue — bachelor’s in electrical and computer engineering — a master’s at Stanford, an MBA from Harvard. What was the original career plan?

Mamoon Hamid (00:01:18): So let’s go back to, I think, 1986. Do you remember the Challenger explosion?

Barry Ritholtz (00:01:18): Sure. Every kid growing up remembers that.

Mamoon Hamid (00:01:28): And one of my teachers was actually supposed to go on the space shuttle, because there was a teacher—

Barry Ritholtz (00:01:36): Christa McAuliffe. That’s right.

Mamoon Hamid (00:01:36): Yeah. And every kid got fascinated, especially if you had a teacher going to space. So I followed the whole journey of the Challenger space shuttle and the teachers and all that. But with that also came this desire to learn more about space, and I instantly wanted to become an astronaut. Naturally — I think I was seven or eight years old. As I thought about high school, liking science and math, and thinking about where to go to college — and as you mentioned, I was growing up in Frankfurt, Germany — one of my uncles had given me this list of colleges, the top 10 engineering schools. I just applied to all 10. And one of them happened to be Purdue, where to this day the most astronauts have graduated from.

Barry Ritholtz (00:02:30): Really? That’s fascinating.

Mamoon Hamid (00:02:31): Yeah. So my path was aeronautical engineering and trying to figure out a way to get into space. I’ve yet to do that, but that is what led me down the path of applying to Purdue in the first place and the association with space and NASA — and then actually going from something so massive and big, space, to something so small, chips and semiconductors and transistors.

Barry Ritholtz (00:02:55): Which are enabling space, so there’s definitely a connection. Is it true that when you went to business school, you were already thinking about being a venture capitalist?

Mamoon Hamid (00:03:06): When I applied to business school — so I’d worked for a good six years after undergrad. I studied electrical and computer engineering, and that naturally made me think about a career in Silicon Valley designing chips, which is what I did for the first six years of my career, working in the semiconductor industry. But what became really interesting for me was the notion of startups and founding companies, and how these so-called venture capitalists were behind some of the most iconic companies I was coming across. So I actually wanted to get into venture capital, and that’s why I applied to business school — and specifically only applied to one business school, Harvard, because I naively thought that if you wanted to get into venture capital, you had to go to Harvard or Stanford. And I’d already gone to Stanford for grad school. So it’d be nice to get a change of scenery—

Barry Ritholtz (00:03:56): Just round it out a little bit.

Mamoon Hamid (00:03:57): And move to Boston.

Barry Ritholtz (00:03:58): Yeah — give up the nice weather. So in between college and grad school, you spent how many years at Xilinx?

Mamoon Hamid (00:04:09): I was there six years. So the story actually goes: I was 19 when I graduated from college, from Purdue, and I thought, okay, the best thing for a young kid is to continue on to grad school. So I applied and ended up getting in at Stanford. But I also got a number of job offers. This is 1997, the dot-com boom — and I’m thinking it’s a bit like this time. Should you opt out of the job market and get extremely valuable experience, or continue on with grad school? So I did the best of both worlds: I went to Stanford, took a few classes every quarter, and worked full time at Xilinx. And this is back in 1997, the middle of the dot-com boom.

Barry Ritholtz (00:04:57): Really interesting. You are known today as someone who thinks about software generally, and enterprise software in particular. That seems like an unusual transition from semiconductors. What led to that shift? What changed your thinking?

Mamoon Hamid (00:05:16): Great question, Barry. So in 2005, when I got into venture capital, my full intent was to learn how to invest in great semiconductor companies, or in founders who build the semiconductor companies of the future. It turns out that after the dot-com bust, there was not a lot of investment in infrastructure — data centers and networking and switching and semiconductors broadly. So I realized pretty early on that if I wanted to build a career in investing, you have to go where the puck is going — skate to where the puck is going. And I skated toward Web 2.0 and software. In my own firm, US Venture Partners, where I started my venture capital career as an associate, I was hired to help the partners evaluate semiconductor opportunities. That’s actually why I went there — there were some legendary semiconductor investors there, and some of my mentors even today were the folks running the firm. But I realized that all my friends in 2005 were moving to Web 2.0 and the internet. This is the beginning of Facebook, which happened to be started at Harvard when I was there. You were seeing all these people in my cohort’s age group moving into software and web, and I felt like I had to move along with that. My day job was evaluating semiconductor businesses, but in the evenings I was in San Francisco, going to the Web 2.0 parties and meeting all the founders starting software businesses. So I slowly started, as a side project — and the side project became the main project — to move from semis to software and the internet. But in the back of my mind, I always remained a semiconductor guy. And semis are back now, as you know.

Barry Ritholtz (00:07:17): And AI seems to be the application of both semis and software, so you’re well prepared. We’ll talk about AI in a bit — I want to stay in the two thousands. When you were at USVP, you had early exposure to companies like Box and Yammer — I don’t really remember Yammer, I remember Box — big enterprise software deals. What did you learn from that experience? What have you brought forward with you from that era?

Mamoon Hamid (00:07:47): So Box happened to be my first investment at USVP, where I joined the board. It was an early-stage company — a few hundred K of revenue, two very young founders, Dylan and Aaron, 20 and 21 years old, dropped out of college. Sort of the prototypical founder, right? The archetype of a young founder. And they were going after storing your files in the cloud and sharing them inside your company.

Barry Ritholtz (00:08:16): Let me stop you for a second, because I think anybody under 40 is perplexed by what you just said. I recall in the late nineties and early two thousands, whether I was at home or at work or on a laptop or at the beach house, whatever I needed was always somewhere else. And the beauty of early blogging software was that I could upload files, charts, images — that was the closest thing to the cloud. It just didn’t exist then. If you wanted something you could access anywhere you had an internet connection, it literally did not exist.

Mamoon Hamid (00:08:56): Yeah. So maybe I’ll go back to exactly the point I made in my head, which was: if there is one application that moves into the cloud first, it’s going to be file sharing. I remember this from when I was on my Windows computer in the eighties and nineties — what’s one of the applications we all used a lot? Do you remember the Windows File Explorer? We were constantly clicking in and trying to find the file—

Barry Ritholtz (00:09:23): Finding something — or searching for it.

Mamoon Hamid (00:09:24): Searching for it, or placing it in a folder very nicely.

Barry Ritholtz (00:09:28): The name you used to put on a file was important, because if you couldn’t remember the name, you couldn’t find it. It wasn’t like, here’s a phrase that’s somewhere in this document, go find it. If you didn’t remember exactly where that was nested or what name you put on it — good luck.

Mamoon Hamid (00:09:43): Good luck, right? And so the world moved from the desktop to the browser — by 2006, 2007 we’re all using Firefox, Mozilla; Chrome’s not even existent—

Barry Ritholtz (00:09:56): It was Internet Explorer until Chrome came along.

Mamoon Hamid (00:09:59): Exactly right. And so my thesis was: one of the business applications that will move into the browser — software as a service — will be file sharing and collaboration. Because, precisely to your point, the file that you always needed was somewhere else. This made so much sense to me. At the time, in 2007, when I invested in Box, there were many of these companies doing file sharing, but it was mostly for consumers.

Barry Ritholtz (00:10:32): Dropbox.

Mamoon Hamid (00:10:33): Dropbox was in that same era, but there was Xdrive and Elephant Drive. As an associate, when you’re suggesting an investment, you’re going to do a lot of diligence — I remember the laundry list of companies I looked at. There were probably 40 companies doing something similar, but most of them were dedicated toward consumer use cases — photos, music, stuff like that.

Barry Ritholtz (00:10:56): The Napster era was right around then.

Mamoon Hamid (00:10:58): Exactly. And so the hypothesis was: this stuff will be relevant to large companies, who will want file sharing and collaboration for their companies. And Box actually pivoted from being a consumer company to being an enterprise company. That’s when I got pretty excited, because it lined up with this view I had that large companies would move from file servers in their data centers, or wherever in their buildings, to files that reside in the cloud.

Barry Ritholtz (00:11:28): And they’re willing to pay for it.

Mamoon Hamid (00:11:30): They’re willing to pay for it.

Barry Ritholtz (00:11:31): Unlike back then, when consumers were so reluctant to pay for anything. So it’s interesting, because you’ve had a lot of early investment success with a variety of companies. Is it easy or difficult to learn from past winners? Is every startup different, or do you develop a little pattern recognition that gives you some clues — hey, these guys are onto something?

Mamoon Hamid (00:11:58): Yeah, I think there’s definitely some compounding of learning from early wins and losses. You brought up Box — my first investment. I got to spend a lot of time with the founders, got to learn the business with the founders, actually, because they were young and I was young — I was in my twenties when I joined the board. From that experience, I learned a lot about what it meant to sell software bottoms-up into large companies, which led me to the investment in Yammer — which many folks may not remember, but it was an enterprise social network circa 2010, kind of like Twitter meets Facebook, but for your company. Microsoft ended up acquiring it in 2012, and it’s part of the Microsoft suite now, part of Teams and all that. But the experience of that bottoms-up adoption — you looked at Yammer, and a lot of large companies wanted an enterprise social network, kind of like a town hall, a messaging platform. You share a file, people comment on it, like people do on Twitter or Facebook. That was taking some of the learnings from the web era and the social era and applying them to the business world. So at Yammer I learned a lot. It was a quick journey, but there was a level of engagement and monetization that was good. And a year or so later, I came across another company: Slack.

Barry Ritholtz (00:13:36): Slack, yeah.

Mamoon Hamid (00:13:37): And it was sort of similar — now it was true messaging. Actually, on my way over here, I was walking through and saw a bunch of colleagues on Slack, which makes me really happy. Slack is used broadly across the globe to this day in 2026. The lessons learned in that 2010-11 era led to the investment in Slack in 2014, for me, when it was a 10-person company. So back to the point about compounding of learning: Box led to Yammer, Yammer led to Slack, and since Slack there have been others. But there certainly is some pattern recognition around products that are working.

Barry Ritholtz (00:14:17): And then in 2011, you co-founded Social Capital with Chamath — a very famous model, which was: how can we address many of the social ills that are hurting the country through the intelligent use of startups, technology, et cetera. Was this a reinvention of venture capital, or just a new set of tools within a partnership? It was kind of novel for its era.

Mamoon Hamid (00:14:50): It was novel for its era, because we decided we would go after education, healthcare and finance — three of the largest parts of society — and address inequities in those areas with our investments, believing that technology has the ability to democratize access to healthcare, education and financial services. And that’s largely played out over the last 15 years. We just thought there would be a ton of opportunity — as venture capitalists, we’re seeking out opportunity, and we thought that by going after large pockets of GDP, you’d identify really exciting opportunities. It turns out my interests remained in enterprise software, and I spent a lot of my time in enterprise software even when we started Social Capital.

Barry Ritholtz (00:15:46): So in 2017, you leave Social Capital for Kleiner Perkins, a firm that has long been iconic. The laundry list of companies Kleiner has backed: Google, Cisco — were they early in Apple also?

Mamoon Hamid (00:16:00): I think they were. Google, Amazon, Sun Microsystems, Genentech, Intuit — unbelievable. Tandem, if you remember. The list of greats is amazing.

Barry Ritholtz (00:16:12): So they’re an iconic company, but they’re not the dominant force they once were. When you joined, what made that opportunity so attractive?

Mamoon Hamid (00:16:22): So look, I had long admired Kleiner Perkins — an extreme reverence, I would call it — going back to my days moving to Silicon Valley. I mentioned I moved to Silicon Valley in 1997 and worked for this company, Xilinx. Think about my first few weeks on the job: I’m in my cubicle, and I’ve got a Sun Microsystems workstation, which was actually a dream, because in college we had to share 20 of them among 2,000 of us. Now I have my own Sun SPARC — I think it was a SPARC 20. And guess what? There’s a Netscape browser, and I’m buying books for grad school on Amazon. And by the way, there are a couple of guys down the hallway at Stanford who are starting this company called Google, and I’m starting to use that search engine. The one commonality among Xilinx, Sun, Netscape, Google and Amazon is that Kleiner Perkins had led the Series A — was the first institutional investor — for all five of those companies. So as a young guy, I developed this extreme reverence for Kleiner Perkins because of the investments they had made in these history-making companies. Which is also what led me to think about venture capital as a career as a young engineer — I wanted to be like those guys; they were investing in all the coolest companies I was using as a 19-year-old. And one of the people behind many of those investments — Sun, Netscape, Google and Amazon — was my partner, John Doerr. So for me, there’s this extreme reverence for John Doerr and his career, and trying to emulate that. He was an electrical engineer from Rice, went to Harvard Business School, worked at Intel Corporation, then came to Kleiner Perkins out of business school. It had a deep meaning to me. And truth be told, in my business school essay — which I still have — I wrote that I wanted to go work at Kleiner Perkins. That was 2002, when I wrote the essay. Then, when I tried to apply for a job in 2005 coming out of business school, I didn’t get very far. But I did end up there in 2017.

Barry Ritholtz (00:18:45): So eventually, if you keep plugging away, you get to where you want to go. That’s great. Coming up, we continue our conversation with Mamoon Hamid, Kleiner Perkins managing member, talking about the reboot of the firm. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

Barry Ritholtz (00:19:07): I’m Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Mamoon Hamid. He is managing member and general partner at Kleiner Perkins, where he is pivoting the firm toward early investments in software, artificial intelligence and automation. So, you co-led the refounding of Kleiner Perkins in 2017-2018. The firm was refocused on early-stage, Series A investing. Tell us what was behind the thought process. What made you say: we don’t want to be bigger, we want to be smaller and more focused?

Mamoon Hamid (00:19:49): If I look back at the decades of Kleiner being probably the most successful venture capital firm throughout the seventies, eighties, nineties, and even the early two thousands, the one thing that defined Kleiner Perkins was that it was a small partnership of seven-ish or so partners who sat around a table in Menlo Park, meeting companies and having healthy discourse and debate about which companies to invest in and what the future of technology would bring to the world. It was defined by a small group of partners who were in many cases technical. They were operators. They had a passion for technology and its impact on humanity. That was what I kept coming back to — that was what defined Kleiner’s decades of success. And we went back to the future, in 2017 and ’18, to that model. Today our partnership is six partners, and we have three more investment professionals. We’re a very small, nimble team. We have two funds, and this team invests from both pools of capital.

Barry Ritholtz (00:21:11): So early stage — is that the seed round, or is it a little more developed?

Mamoon Hamid (00:21:17): The early-stage fund is seed and Series A mostly, and maybe some Bs. And the growth fund is Bs and Cs all the way to — we invested in the last Anthropic round at a $900 billion valuation, which is rare, for special companies. But it has the ability to invest across stages, even to the pre-IPO round.

Barry Ritholtz (00:21:41): And is it a coincidence that the growth fund is two and a half times the size of the seed fund? At that point these companies are bigger and require a bigger check — or is that just happenstance?

Mamoon Hamid (00:21:54): I think our funds are sized based on the opportunity set in front of us. Our early-stage funds have been almost exactly 35 companies for the last 15 years. So 35 companies per fund, which we think of as the right number of shots on goal for an early-stage fund to return multiples.

Barry Ritholtz (00:22:17): Like 25 to 30 million per?

Mamoon Hamid (00:22:20): Exactly. So it starts out with maybe, in some cases, a $5 million check, and the subsequent checks are another 15 or 20. Or the first check could be 30, and then with pro rata you’re investing, let’s say, up to $40 million per company. And then your growth fund is doubling down, investing a lot more in those companies.

Barry Ritholtz (00:22:39): Really kind of interesting. So the focus is artificial intelligence startups across the software, healthcare, transportation and autonomy industries. Let’s unpack that, because I’m hearing a little overlap with each of your prior venture experiences. Tell us why those four areas are so attractive.

Mamoon Hamid (00:23:04): This is a truly once-in-a-lifetime revolution that we’re going through with AI, and the number of exciting companies and people that we’re seeing right now is at an all-time high. The whole world, in some ways, is being refactored with AI — and this is just the very beginning. So I would say all parts of the economy, even beyond those four areas. Like I mentioned earlier: healthcare, financial services, all sorts of knowledge work. It’s going to be all sorts of physical automation in terms of robotics. Even space, even defense, drug discovery, materials discovery. I think it is all fair game at this point in terms of where the exciting pockets of innovation are, because there has never been a tailwind like this — one that allows all parts of the world to be refactored based on the biggest technological revolution ever.

Barry Ritholtz (00:24:30): I’m glad you described it that way, because I keep hearing people compare AI to the internet, and that seems too contained, too timid. I wonder if you agree with the thought that the only thing remotely comparable to this is the industrial revolution — which, centuries later, we are still dealing with the impact of.

Mamoon Hamid (00:24:54): I absolutely agree with you, Barry. It is like the industrial revolution. It’s like the railroads. It’s like the printing press. It is that. It’s not the internet.

Barry Ritholtz (00:25:04): That’s really interesting, because when I think internet, the first thing you think of is: oh, this is a bubble and this is going to collapse. But you mentioned you’re an investor in Anthropic — these are, forget not-profitable companies, these are companies with giant revenue streams already, and they’re barely a few years old. How big can this sector get? Is this going to take over every corner of the economy?

Mamoon Hamid (00:25:31): Let’s talk about that. I think that’s the real conversation — the very exciting conversation one can have about this topic. I’ll start at a very high level. The GDP of the world today is about $120 trillion, and about half of that is labor — the labor component. So roughly $60 trillion. And of that $60 trillion, roughly 60 percent or so is white collar — maybe 50 to 60 percent, somewhere in there. So that’s anywhere from $30 to 35 trillion. And if you look at tokens, and what the frontier model companies provide, it is units of labor. We’re already seeing how those units of labor are being utilized in computer science — software development — in law, in medicine, in drug discovery. These are little agents and buddies that we as humans now have to help us do more with our intellect. The way I see it, we’re talking about trillions of dollars opening up for these companies. Exhibit A is a company like Anthropic, which, as it has publicly stated, has gone from zero to a $45 billion revenue run rate — that’s unbelievable — in a matter of less than three years. And that is likely going to double. The company started this year, I believe, at 20, and has already more than doubled in the short year we’ve been in so far. These numbers are astounding, not only because these companies are selling software or technology — they’re selling units of labor. And the labor markets, as we all know, are the biggest component of the world’s GDP. We’re talking about trillions of dollars of opportunity. That’s what excites us so much about this time: it’s not just about selling tools and software that we’ve been accustomed to selling to IT departments. It’s selling actual labor — to companies, to corporations, even to consumers who are using AI in their personal lives.

Barry Ritholtz (00:28:01): So let’s talk a little bit about that. The fear I keep hearing is that everybody’s going to lose their job. It’s a very Malthusian argument — that this technology is going to replace labor the way the steam engine did. I’m getting a sense from the data, and from analysts like Torsten Slok, that this isn’t a replacement for white-collar labor, it’s an enhancement — or at least that’s the argument. Give us your perspective on that.

Mamoon Hamid (00:28:33): I actually fully agree with the point of view that you have. It’s like getting email. When we got the computer, the people who were using the typewriter started using the computer and started doing other types of jobs. Even in the steam era, the industrial revolution, we found ways to repurpose jobs and people and their skills. I don’t think humans are going out of style. I don’t think the world is going to be largely unemployed and on UBI because we’ve displaced all this work and all these people with AI. That’s the extreme where the mind goes, but it’s just not the reality. And that bears itself out in the numbers we see — record low unemployment rates. Actually, we need more labor, more people, than we ever have.

Barry Ritholtz (00:29:30): More skilled labor. We are seeing a decrease in job availability for kids right out of college, for unskilled labor. If anything, is this likely to force more people to get more technical, to up their skill set?

Mamoon Hamid (00:29:49): I actually do believe that. It is not: oh, you don’t need to be a software developer and study CS anymore because these software jobs are going away. It’s that now the job of a software engineer is to manage a whole host of agents, make them do work for them, and be the brains behind the operation. Think of it as having all these little agents — little employees — working on your behalf. That is the higher-level thinking. When we go to school, we learn how to problem-solve. If we’re solving a math problem and it’s hard, we think about many different ways to solve it. The same applies here: how am I going to use AI to help me solve problems? We have four kids, believe it or not, and I’m telling them: go into math, science, and actually art — have spectral diversity in your learning — because the skills that mattered in the past, solving math problems with pen and paper, will really matter in the future.

Barry Ritholtz (00:30:55): So let’s bring this back to how you think about the opportunity set that’s out there at Kleiner Perkins. You do structured reviews of every interesting deal that was passed on. I’m kind of fascinated by that. I know a lot of VCs hold their misses as a badge of honor — some firms post them on their website. What’s driving the thought process around revisiting missed deals or mistakes? What does the process teach you?

Mamoon Hamid (00:31:35): One of the things I did when I got to Kleiner Perkins in 2017 was that we would look every week at that week’s Series As that got done by our peer firms — about 30 or 40 firms — and whether we had seen the company that was invested in or not. A simple heuristic: are we seeing the things that matter — and they seem to matter because our peer firms invested in those companies. We’ve been doing this now for the last nine years. Initially our goal was that we should see 60 percent — and seeing means you met the company. For us, that now hovers around 70 percent or so. You don’t want it to be a hundred percent, because then that’s just the game you’re playing — we just see everything. And you don’t want to be at 20 percent, because you’re not seeing enough. We think 70 percent is a good number. And then we look at it: if we saw 70 percent of the good stuff, was the better stuff in the 30 percent we didn’t see? Or, of the 70 percent we saw, did we pass on the good stuff and do the bad stuff? We go through that exercise quite frequently. We just had an offsite a few weeks ago, and we went through it again — we pour salt on the wounds. Okay, we saw these companies and we passed. Why did we pass at that early-stage round? Just to remind ourselves why we need to adjust the way we do things. I’ll give you an example: Anthropic, which is an incredible company. The Series A was not a traditional one — SBF from FTX led the Series A, famously. We know how that worked out.

Barry Ritholtz (00:33:24): We do know how that worked out.

Mamoon Hamid (00:33:24): It was an amazing investment and very prescient on his behalf. I forget how much it would be worth today, but it would be worth a lot. But the Series B was a sort of non-consensus, non-obvious round. We actually met with the founders — but we met them over Zoom, and we played with the product. You don’t get the same visceral feeling about a company and the founders and their ambitions and aspirations and what they’re trying to do with their company. So — what a miss, right? I think that round got done at a $4 billion valuation or something, which is not a small valuation, but still—

Barry Ritholtz (00:34:08): Compared to today.

Mamoon Hamid (00:34:09): Compared to today. And we looked at a lot of our passes that were good companies, and many times we just didn’t meet them in person. The pandemic era bred some really bad habits — you did a first meeting over Zoom. I looked at my own investments, and for the last 20 investments I’ve done, the first meeting was always in person. So I’ve driven my whole calendar to: I just don’t want to do any meetings on Zoom anymore. I want to meet people in person, and if it’s worth a 30-minute Zoom, it should be worth a 30-minute in-person meeting. And I’m glad we get to do this in person — big difference. It wouldn’t be the same thing if I were on a Zoom screen doing this with you.

Barry Ritholtz (00:34:59): That’s exactly right. What about the reverse of that? If you’re analyzing your misses, do you ever review your hits, your wins, and ask: why did we get this right? What can we take forward from this?

Mamoon Hamid (00:35:14): That’s a great question. What we do look at is: is the portfolio that we built better than the portfolio that we missed? And it’s actually a toss-up.

Barry Ritholtz (00:35:32): Huh — that’s really interesting.

Mamoon Hamid (00:35:34): In the sense that it would be bad if we didn’t see companies and that basket of companies was way better than the companies we saw. We try to be very intellectually honest about whether we’re seeing the right stuff or the wrong stuff — and it turns out it’s a toss-up.

Barry Ritholtz (00:35:56): The reason I ask that question is that in the public markets, you learn more from your misses than your wins, because it’s very hard to tell the difference between skill and luck in the public markets. I’m curious if the same sort of thing applies to venture.

Mamoon Hamid (00:36:15): I think it does. You really beat yourself up on the misses, and on the ones you did do, you’re just like: okay, check, it happened — and maybe you don’t think about them as much as the ones you missed.

Barry Ritholtz (00:36:29): Really, really interesting. Coming up, we continue our conversation with Mamoon Hamid, partner at Kleiner Perkins, discussing the state of venture investing today. I’m Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio.

Barry Ritholtz (00:36:46): I’m Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. Mamoon Hamid is my extra special guest. He is a partner at Kleiner Perkins, where he’s driving the firm’s focus on early-stage investments in artificial intelligence and related technology. So let’s talk a little bit about the state of venture investing today. When you meet a founder for the first time — preferably in person — what are you looking for? What are you trying to spot that isn’t in the pitch deck they sent earlier? How do you separate intensity from delusion? What are you trying to identify in that first meeting?

Mamoon Hamid (00:37:32): It is the most interesting time in my venture career, for obvious reasons — this AI revolution. The tailwinds that AI brings to companies being started today are unlike anything we’ve seen before. So the quality of ideas is at an all-time high, and I would say the quality of the people is also at an all-time high. Those two forces combined mean there are a lot of really high-quality ideas and founders that we’re seeing — and the volume, because of that, is at an all-time high. To your question of what we’re looking for: obviously everything today is AI-enabled, with AI tailwinds — and venture capital isn’t venture capital unless there’s a strong tailwind of something. That makes this such an exciting time, because the winds are so strong — in some ways because the frontier model companies are providing better and better models, which allow companies that build on those models to provide a strong value proposition. Take, for example, a company like Harvey, which is AI for legal. It’s in most of the Am Law 100, sells to large enterprises and Fortune 100-type companies, and is becoming the de facto way that law firms and legal departments are using AI. And yes, they have a lot of secret sauce on top of what the model companies provide, but at the same time, they get better and better as these models get better and better. This is a category that just got created in the last few years, and there are numerous examples like it in every sector of society. Just take a step back — I don’t know what your reaction was to ChatGPT when you first saw it, but for me, it was the same reaction I had when I first got to use an internet browser. That Netscape moment was equivalent to the ChatGPT moment. And we started to think about the second-order effects — what are the things that come from here, from ChatGPT, from LLMs? We thought about the labor pyramid — think about knowledge work. We went straight to: what are the most highly skilled, highly paid jobs in the country? If you look at the top 20 list of jobs by dollars earned, it’s some form of engineer, doctor or lawyer. So what we did at Kleiner Perkins was invest in companies that do AI for legal, AI for software development, AI for medicine. We invested in companies like Harvey; Windsurf, which got acquired by Google; and companies called Ambience and OpenEvidence — to go after the top of that labor pyramid. And back to your point, it’s an enhancement for those people. It was supposed to be like a copilot — which it is—

Barry Ritholtz (00:41:04): Registered trademark, Microsoft Corporation.

Mamoon Hamid (00:41:07): Yeah, exactly — Copilot. And in some cases it’s become an autonomous agent for those people. Software developers run agents to do work for them now. And so we worked our way down the labor pyramid a bit — what’s the next level? If doctors, lawyers and engineers are in the $200K-plus-a-year pay range, what’s one level below that? You’ve got financial analysts, salespeople, nurses. So we’ve invested in that next class of companies: Rogo, which is AI for finance; Hippocratic, which is an agentic nursing platform; Nooks and Revo, which are helping salespeople — copilots for their work. So we’ve worked our way down the labor pyramid. And if you think about the pyramid, guess what’s at the bottom? Physical labor — the lowest paid, lowest skilled in some cases. Eventually robotics will get there, and hopefully do a lot of the backbreaking work that nobody should be doing. That goes along with the timeline of how we’re thinking about these things: you start with the highly skilled, highly paid, and over the next decade you get down to the lowest-skilled, lowest-paid work.

Barry Ritholtz (00:42:31): So you mentioned the tailwind behind AI. What does that do to valuations? How do you underwrite startups in a market where even the half-decent companies look kind of expensive?

Mamoon Hamid (00:42:46): Great question. When you have companies that have gone from zero to a trillion dollars in value in the last three to four years — when you’re a founder, what do you do? You point to that. That’s what I can be; I can get to a trillion dollars, because I’m going after really large problems. And we love that ambition. What do people do then? They say: well, if the probability of a $1 trillion outcome is 1 percent, and you add up the probabilities for all the other outcomes, you’ve got yourself an expected value of $10 billion or more — at least that’s the minimum. You do the 1 percent of $1 trillion, that’s $10 billion, and you add up all the other probabilities, and it’s probably like 30, 40, 50 billion. So if you’re looking at a Series A company where the ambition is tremendous, the valuation may just be — you’re raising a hundred million at a billion-dollar valuation for two guys out of the gate. And those are real examples. I think we’ve got a bit of this pointing at the large outcome — and if it’s paired with smart people and an ambitious idea, it has that kind of potential. But the reality is there are usually only one or two of those real outliers that are Mag Seven scale. Gravity in itself doesn’t allow for the world to have a hundred trillion-dollar companies.

Barry Ritholtz (00:44:28): Plus, if it’s a trillion-dollar total addressable market, it’s going to attract a lot of competition, a lot of other startups — perhaps more than if you’re focusing on a smaller niche. Although even in cloud storage, you mentioned 40 companies in the early days. There have got to be tens of thousands of companies going after each of these segments in AI.

Mamoon Hamid (00:44:53): Yeah, there are. And the hard part of the work we have is identifying what we think will be the leading company, because in technology, generally speaking, the leading company gets most of the market cap — which, if you look at the Mag Seven—

Barry Ritholtz (00:45:10): Winner take all.

Mamoon Hamid (00:45:11): Winner take most, right? They take 90 percent of the market. Nvidia — 95 percent of all GPU spend. Take Google, Alphabet — multiple businesses. Or take a Tesla; take a Meta — owns social. So winner takes most in technology.

Barry Ritholtz (00:45:30): Really interesting. You’ve described the AI moment as one of the most important company-building opportunities in our lifetime. What’s the risk of venture funding too many of these startups? Or is this just a fat head of winners and a long tail of well-we-gave-it-a-shot? Is this simply the nature of this business, where a couple of winners drive all the returns for your funds?

Mamoon Hamid (00:45:59): Venture is a power-law business — there’s no question about it. There’s this article I read the other day where 90 percent of the AI revenue is in the hands of two companies.

Barry Ritholtz (00:46:13): That’s crazy.

Mamoon Hamid (00:46:14): OpenAI and Anthropic. The remaining 10 percent is in a bunch of companies that are excellent companies, but the scale of those two companies is so massive that it dwarfs all the other great work happening in tons of other companies that we’ve backed. And by the way, those will be great outcomes and great companies — there’s no question about it. It’s just that the power law really shows itself when you look at the numbers. Yes, our job is to be in the companies that make history and follow the power law. What we find is that you would think there are dozens of companies — there are actually tens, maybe fewer than 10, and there are two to three that are converging to become the winners in a category. Everyone’s trying to identify those two to three companies and be in them. One of the challenges we face is that we try to invest early in what we think is the winner in the category. Sometimes you don’t know early that this is the winner, and if you invest too early, you conflict yourself out of the eventual winner.

Barry Ritholtz (00:47:28): You only invest in one company per silo, so to speak? Just to avoid those sorts of conflicts.

Mamoon Hamid (00:47:35): Yes. Typically we’re joining the boards of these companies, and if you have confidential board-level information and you then invest in a competitor, all of a sudden there’s a chance of a conflict of interest. So we definitely try to avoid that.

Barry Ritholtz (00:47:51): So I’m kind of fascinated by this: as venture investors, you obviously see the promise of AI across all these different economic sectors. I’m curious how you are using AI internally at Kleiner Perkins. Are you using it to source deals, or do due diligence, or predict specific outcomes? How does AI fit into your operations?

Mamoon Hamid (00:48:17): We have definitely been maxing out on AI internally — not only because we invest in these companies. Glean is a company we incubated inside of Kleiner Perkins, actually — it’s in year seven now, a pre-AI company started by an incredible engineer, Arvind Jain. That’s our knowledge management. Every single piece of knowledge inside Kleiner Perkins resides in Glean, and you can go to it, query it, chat with it. If I want to find your phone number and email — say I’ve never met you before, but I know someone at Kleiner probably knows you — I’ll go to Glean. If I want to ask about an HR policy, I’ll go to Glean and quickly ask, because it just knows everything about Kleiner Perkins. It knows investment memos, it knows cap tables — it knows the really confidential stuff. It’s permissioned in a way where the people who are supposed to know can know. That’s part of the magic: it’s very safe and secure, and you trust it to know the things it’s supposed to know and not know the things it’s not supposed to know. So that’s one example. But we also get so much information — board decks, long board memos, financials. I’m going to a board meeting after this, and I got the board memo. The first thing I do is send it to an email alias that runs it through AI, and it produces a summary of the board meeting and questions I should be thinking about — an instant step I take once I get the board materials, so that I start thinking about it before I actually go read the board memo. I sort of have a preview of it in my mind. We do a portfolio review every four months or so, and we have a couple hundred companies. It used to be a very manual process — we had a dedicated person working on it. Now our technology team has built a system where we take these summaries and they get piped into this portfolio book that we create, with all the financials and all the metrics. We’re heavily leveraging AI there — in this case it’s Glean and Claude, the underlying models, obviously. And we’ve done a bunch of other things. I actually love to rate my meetings, just so I remember the tens and the nines that I should have paid attention to but forgot. I want to have an exhaust of all the things I’m encountering in my real life, and AI is an amazing capture of that exhaust — providing intelligence and signals to our team, piping it into our CRM. There are all these cool things we’ve done. We have an internal tech team — an amazing team of four folks who build a lot of these tools — and we are definitely maxing out on using everything that’s out there.

Barry Ritholtz (00:51:20): Really quite fascinating. So, final question before we get to our favorites that we ask all of our guests: what are investors not thinking about when it comes to AI — or anything else — that perhaps they should be? What sort of topics — policy, data, geography — what’s getting overlooked but shouldn’t be?

Mamoon Hamid (00:51:42): I think right now we’re going through a time where software is considered to be dead — they call it the SaaS apocalypse, right?

Barry Ritholtz (00:51:53): Although they’re just coming off their lows.

Mamoon Hamid (00:51:55): Yeah. And there’s always an overreaction: oh my God, it’s going to be an AI capex world, and only chips will matter — only fiber and data centers and power will matter. The reality is that the way we as humans interact with technology is through software — through the things we have known as software and tools. And by the way, CIOs in large companies buy from companies that sell to them; they don’t just buy a smart agent. So I think the pendulum has swung a little too far, and we underappreciate what software still does and will continue to do forever — for our enterprises, for governments, et cetera.

Barry Ritholtz (00:52:41): Software: not going away. Really interesting. All right, let’s jump to our favorite questions, starting with: who are your mentors who helped shape your career?

Mamoon Hamid (00:52:51): One of my mentors is Irwin Federman, whom I dearly love. He’s 90 years old now. He’s a New Yorker — he sold peanuts, I believe, at Dodger Stadium when the Dodgers were still there in the fifties. He was my mentor at USVP, and he’s a legendary semiconductor investor, believe it or not. He was one of the co-founders of SanDisk Corporation, and before that he was CEO of Monolithic Memories.

Barry Ritholtz (00:53:22): I hope he still has a few shares of those.

Mamoon Hamid (00:53:24): He probably does. And SanDisk is in this memory hype cycle we’re going through — hype or not, there’s a real need for memory. I believe it’s now maybe a half-a-trillion-dollar market cap company. Something crazy — don’t quote me on that, but memory is having its day right now. In any case, he was a mentor because not only did I work for him, but I saw through his lens how to be a great board member, how to make investments, how to back people, how to build relationships with people. He also gave me feedback that no one else in life would, because I think he loved me — I really felt the love — because the kind of feedback he gave me was feedback that I don’t think people would generally have the courage to give you. It’s pretty direct — tough love. And I love that about him. It reminds me that I need to go pay him a visit.

Barry Ritholtz (00:54:25): Well, you’re in New York — you might as well.

Mamoon Hamid (00:54:27): Oh — no, he actually lives in the Bay Area now. He’s a New Yorker who relocated to the Bay Area, I think, 50 years ago.

Barry Ritholtz (00:54:34): So let’s talk about books. What are some of your favorites, and what are you reading currently?

Mamoon Hamid (00:54:38): I’m just starting on this book called Believe — why you should believe, especially in this era of AI. I’m on the board of a company called Thrive Global, whose CEO and founder is Arianna Huffington. Arianna gave me the book. She and I have very aligned views on faith and spirituality — Arianna, I believe, is Greek Orthodox, and I’m Muslim — and we talk about how faith guides our lives, and about this age of AI. That’s actually the conversation she and I have. She said: I have the perfect book for you. It’s about how we should believe even more in this age of AI, because it helps us understand the world — we’re trying to make sense of it all the time. Religion can give us a bit more of a constrained view of what the world actually is, because otherwise it’s just a black box; you won’t be able to comprehend the vastness of what we’re trying to comprehend as human beings. And especially with AI, we’re pushing the boundaries of what’s possible. I think there’s actually more in the scriptures than you’d think — that’s the view she and I share, and this book hits home with it. It’s by the New York Times columnist Ross Douthat. Believe — check it out.

Barry Ritholtz (00:56:16): On my list now. What about streaming? I know you host a podcast. What do you either watch or listen to these days?

Mamoon Hamid (00:56:25): My wife and I love to watch Dateline, 48 Hours — these crime shows.

Barry Ritholtz (00:56:31): All the crime shows.

Mamoon Hamid (00:56:31): All the crime shows. In some ways it just takes things down a notch, but it’s also so instructive about human psychology — what motivates people to do not-so-great things. And there’s generally a theme to it at this point; it’s a very repetitive theme.

Barry Ritholtz (00:56:52): It’s Dunning-Kruger. They have no idea about the trail of DNA evidence they leave everywhere. Anytime I’ve watched that show, it’s like — what are you doing?

Mamoon Hamid (00:57:01): And it should be that it’s harder and harder to commit crimes.

Barry Ritholtz (00:57:07): And yet—

Mamoon Hamid (00:57:08): There are still crimes.

Barry Ritholtz (00:57:10): Still — and just as many as ever. Only people are getting caught more easily.

Mamoon Hamid (00:57:13): Yeah. And the cell phones — they’re pinging those towers.

Barry Ritholtz (00:57:18): What do you mean you weren’t in the house? We can tell you were within a hundred feet of this person at that time.

Mamoon Hamid (00:57:23): Exactly. So it’s probably not a very full answer — you’re probably looking for some cool show that I watched.

Barry Ritholtz (00:57:30): No, not at all — I’m fascinated by that. It’s funny, because there used to be this giant gap between the CSIs and what was actually going on. But if you watch the two of them, it’s really closed. Maybe there’s a little selection bias here, because all those shows are about the people who got caught — so you’re seeing where the technology worked, where the forensic science got that guy. It’s really very funny. All right, our final two questions. What sort of advice would you give to a recent college grad interested in a career in either venture investing or technology?

Mamoon Hamid (00:58:12): It’s probably the same advice I would have given 20 years ago, or given myself coming out of college: go work at a fast-growing company, where you can learn from the growth it’s encountering, but also from the people — and build the network that you’ll have for the rest of your life. It’s probably the best time in your life, coming out of college, to learn from others around you and to experience high growth, because from high growth, lots of lessons are learned. If you can find a way to get into a high-growth technology startup — an AI startup — it is the best way to develop the skills, but also the empathy of what it means to have carried a bag and sold something, and built something, and shipped something. I always tell folks there shouldn’t be a direct path into venture capital. It’s a second thing — it’s not the first thing you do coming out of college or grad school. You have to have built and shipped and sold, and developed that empathy for high growth and the lessons learned, before you get into our career.

Barry Ritholtz (00:59:26): Really, really interesting answer. And our final question: what do you know about the world of venture investing or technology today that might have been useful 25 or 30 years ago, when you were first ramping up?

Mamoon Hamid (00:59:40): It’s all about the people. It sounds so trite, but it is. I say: ordinary-looking people doing extraordinary things. And how do you assess those ordinary people who are doing extraordinary things? By really understanding the people — their intentionality, their desires, their ambition, what drives them, their motivation. Which goes back to why you meet them in person: you’re trying to figure out why they are doing this. Building a startup, a company, is hard work. It’s a sacrifice on life. So there had better be a good reason why you’re doing it.

Barry Ritholtz (01:00:18): Really interesting answer. Thank you, Mamoon, for being so generous with your time. We have been speaking with Mamoon Hamid. He is partner at Kleiner Perkins. If you enjoyed this conversation, well, check out any of the 647 we’ve done over the past 12 years. You can find those at Apple, Spotify, YouTube, Bloomberg — wherever you get your favorite podcasts. I would be remiss if I did not thank the crack staff that helps put these conversations together each week: Alexis Noriega is my video producer, Sean Russo is my researcher, Anna Luke is my podcast producer. I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.

 

~~~

 

 

 

The post Transcript: Mamoon Hamid, Kleiner Perkins appeared first on The Big Picture.

10 Monday AM Reads

My extended long weekend reads:

The World Cup Shows What’s Great About America: Even if the so-called “Pro-America” crowd hates it. Kinzinger finds a burst of unforced patriotism in the tournament crowds. An earnest note for the holiday weekend. (Adam Kinzinger)

This Simple White Line Is America’s Greatest Unsung Innovation: The painted road line as overlooked genius, part of the WSJ’s America-at-250 series. A perfect Fourth-of-July ode to the unglamorous stuff that works. You know about the lightbulb and the iPhone. This is the unknown story of another ingenious creation that changed a nation (Wall Street Journal)

The Case for Buying Individual Muni Bonds. There are advantages for those with muni holdings of $250,000 or more to opting for an individualized, actively managed portfolio. There are unique aspects of the muni market supporting this preference. (Barron’s)

Meet the Bodyguards Signing Up to Protect America’s Frightened Billionaires: After a season of high-profile assassinations, political violence, and kidnappings, wealthy Americans are racing to hire personal security services. GQ on the private-security boom catering to anxious tech and finance moguls. Genuine threat or vanity expense — the budget moves either way. (GQ)

Seven observations from playing with AI: I thought it was important to try this technology for myself and see how good it is. Here are seven hype-free observations I have taken from the experiment: Hands-on field notes from actually using the tools, not theorizing about them. (Gavin Jackson) see also Claude: What Are You Good At? I had a little chat about how to best use AI with Claude, see what AI itself had to say on the topic of using AI. Practical, from the user’s chair. My own notes on where these AI assistants actually earn their keep — and where they don’t. (The Big Picture)

The Internet I Grew Up With Doesn’t Exist Anymore: A thorough retrospective of my time on the internet. A wistful elegy for the open, weird, pre-platform web. Familiar territory, but this one’s heartfelt. (Christian Cleberg)

$22,000 Per Hour: Assistants Use a Legislative Loophole to Outearn Surgeons: The Upshot finds a billing loophole turning surgical assistants into improbable high earners. American health-care economics, distilled. A law meant to end surprise medical billing has led to large paydays for some surgical assistants, who can earn far more than the doctors they help. (New York Times)

‘All I Have Is the Power to Talk and Be Heard’  The Interview: Tucker Carlson on pitying Donald Trump, never listening to podcasts, and planning a new political party—while selling you nicotine pouches. (Columbia Journalism Review)

Inside the Food Truck Mafia Wreaking Havoc Around the National Mall: Turf wars. Food and fire hazards. $15 ice-cream cones. How an organized network of unlicensed food trucks took over America’s Front Lawn (Washingtonian) see also The Capital Is a Mess: Chain-link fences, construction cranes, armed guards, and portable toilets everywhere. Construction chaos remakes the National Mall. Washington as perpetual job site — and a fitting backdrop to the food-truck turf wars above. Chain-link fences, construction cranes, armed guards, and portable toilets everywhere (The Atlantic)

The Tick That Hunts Down Its Hosts—Including Us: The unsettling biology of a tick that actively pursues its prey. Excellent, mildly horrifying nature writing. Lone-star ticks don’t just pursue and bite people. The affliction they’re spreading, an allergy to red meat known as alpha-gal syndrome, attacks a way of life. (New Yorker)

Phil Mickelson’s Long History of Misconduct: A detailed accounting of behavior the golf world has long whispered about. The reporting Lefty’s carefully managed image was built to outrun. Interviews with 19 sources reveal two incidents of lewd language and unwanted advances, and the behavior that led to his departure from two additional golf clubs. (Skratch)

Video of the day: Google Maps is unreasonably fast. Let me explain

Be sure to check out our Master’s in Business with Mamoon Hamid, partner at Kleiner Perkins. He is a leading investor in enterprise-software and AI. He was an early investor in Slack, Figma, Rippling, Glean, Netskope, and Box. Hamid co-founded Social Capital with Chamath Palihapitiyal. In 2017, joined Kleiner Perkins

 

America at 50, 100, 150, 200 & 250

Source: Bruce Melhman

Sign up for our reads-only mailing list here.

 

The post 10 Monday AM Reads appeared first on The Big Picture.

10 Sunday Reads

Avert your eyes! My Sunday morning look at incompetency, corruption and policy failures:

Surveillance Tech Company Is Pitching An Unholy ALPR/Stingray Hybrid To Law Enforcement: Here’s something no one but cops and the tech firms that love cops wanted: an Automated License Plate Recognition (ALPR) that can scoop up pretty much any information being broadcasted by cars and the devices carried by the people inside them. As if ALPRs weren’t already controversial enough, here comes a tech company offering that makes most ALPRs (including those sold by Flock!) look absolutely innocuous. License-plate readers meet fake cell towers in one tidy package. The surveillance-creep beat keeps finding new lows. (TechDirt)

How Some Private-Equity Managers Collect Big Fees on Paper Gains: Fee structures are among the pitfalls of investing in semiliquid funds (Wall Street Journal) see also Private Credit Is Making Bets on Consumer Debt at a Precarious Time: Billions are flowing from firms like Blue Owl and KKR into Buy Now, Pay Later companies. It’s an untested model and skeptics are worried about what happens in a downturn. The private-credit boom wades into buy-now-pay-later just as households strain. A flashing-yellow-light story worth your attention. (Bloomberg)

How a Master of Deception Conned Investors Out of $50 Million—in His Own Words: Paul Regan recorded himself ripping off clients to teach others how to do it, too. A fraudster narrates his own scheme. First-person grift is uncomfortably compelling — and instructive. Those tapes reveal the inner workings of a fraud. (Wall Street Journal)

What Big Food Did to Ice Cream: The slow degradation of the supermarket pint, explained with real food science. Enshittification comes for dessert. The “encrapification” of the American pint — a chemist’s plain-language dissection. (Medium)

Forget Baseball: Gambling Is America’s Real National Pastime. “It is one of the defects of our national character… that no sooner do we get hold of a good thing of this sort, than we proceed to make it hurtful by excess.” A book-bite argument that betting, not baseball, is the true American sport now. Fits the week’s wildfire-and-insider-betting theme uncomfortably well. (Next Big Idea Club)

A Terrible Thing Happened to My Family: Buttigieg writes personally about a family ordeal: Many times over the years, I have been denounced, yelled at, protested, threatened, and heckled. I’ve been through political attacks in office, death threats in public life, and rocket attacks in war. But this is the ugliest thing that has happened to me since my career in service began. Even in today’s climate, there should be one fundamental principle everyone respects: whatever you think about someone in politics, you leave their kids alone.  (Pete Buttigieg)

How BP Execs Influenced a Climate Study That Shaped a Generation of Global Policy: ProPublica traces how an oil major’s hand quietly steered the influential ‘wedges’ framework. A story about who gets to write the science. (ProPublica)

Trump Cut a Billion-Dollar Mining Deal. His Sons Stand to Profit.: A Kazakhstan minerals deal with a familiar conflict-of-interest aroma. The family-business presidency, chapter umpteen. An agreement between the U.S. and Kazakhstan has given a group of American investors with ties to the president and the commerce secretary access to one of the world’s largest untapped reserves of tungsten. (New York Times) see also A Trumpworld Events Company Is Raking In Millions in Federal Contracts: The Trump administration has awarded Event Strategies several contracts—including one that could be worth up to $100 million—with little competition, according to federal filings. The team behind the January 6 rally now cashes government checks. Wired follows the money from the Ellipse to the federal ledger. (Wired)

Alarming New Trend Dominating Youth Sports: Repeating 8th Grade. Families Pay Thousands for It.: Parents paying to hold kids back for an athletic edge. A depressing arms race dressed up as opportunity. A surge of for-profit ‘reclass’ academies are raising equity and oversight concerns across N.J. scholastic sports. (NJ.com)

• EU Politicians Investigated Pegasus Spyware. Then It Ended Up on One of Their Phones: “It is a direct attack on the rule of law,” says one European Parliament member of the new findings from Citizen Lab. The watchdogs become the targets. A chilling reminder that commercial spyware doesn’t respect who’s supposed to be holding it accountable. (Wired)

Video of the day: Are Humans Badly Designed For Modern Life?

Be sure to check out our Master’s in Business next week with Mamoon Hamid, partner at Kleiner Perkins. He is a leading investor in enterprise-software and AI. He was an early investor in Slack, Figma, Rippling, Glean, Netskope, and Box. Hamid co-founded Social Capital with Chamath Palihapitiyal. In 2017, joined Kleiner Perkins


Do Competitive Seats Matter?


Source: Bruce Mehlman’s Age of Disruption

 

Sign up for our reads-only mailing list here.

~~~

To learn how these reads are assembled each day, please see this.

 

The post 10 Sunday Reads appeared first on The Big Picture.

MiB: Mamoon Hamid, Kleiner Perkins on AI Investing

 

 

This week, I speak with Kleiner Perkins partner Mamoon Hamid. We discuss Mamoon’s thoughts on the AI revolution and his approach to early AI investing.  Mamoon also breaks down how he became an early investor in giants like Slack and Figma, and how the firm assesses the investments they missed.

He explains how Kleiner Perkins pivoted towards earlier-stage seed investments.

A transcript of our conversation is available here Tuesday.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube (video), YouTube (audio), and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

Be sure to check out our bonus Masters in Business this coming next week with McKeel Hagerty, CEO/Chairman of Hagerty Specialty Insurance. He transformed a family specialty-insurance agency into an enthusiast-driven platform focused on collectible cars, events, valuation data, and auctions. HGTY is now a public company that insures everything from classic cars to boats, trucks, tractors, and military vehicles for over 2.8M collectors.

 

 

 

 

 

The post MiB: Mamoon Hamid, Kleiner Perkins on AI Investing appeared first on The Big Picture.

10 July 4 Reads

The weekend is here! Pour yourself a mug of Danish Blend coffee, grab a seat outside, and get ready for our longer-form weekend reads:

Why You Grieve the End of Summer Before It’s Even Over: If you’re already stressed about the end of the season, you’re not alone. On anticipatory nostalgia and the human knack for mourning things mid-enjoyment. A lovely small essay for late June. (Vox)

US at 250 – Why Has the US Been So Successful, and Can It Continue? First, we consider how the US went from being a comparatively small country to the world’s pre-eminent global power. These reasons range from the US’ natural advantages, like favourable geography, to factors like its institutional stability and risk-tolerant capital markets. We then consider the challenges that threaten US outperformance. A big-picture bank note on American exceptionalism and its durability, timed to the semiquincentennial. Sweeping, and a useful counterweight to the doomers. (Deutsche Bank Research Institute) see also How a Nation of Immigrants Traces Its Roots: A data-rich map of where Americans say they come from. The census as a mirror of a changing self-image. Melting pot, tapestry, mosaic, kaleidoscope, salad bowl. Every cliché is true. (New York Times)

Abraham Lincoln’s War on King Cotton: How economic warfare over cotton shaped the Union strategy. A sharp piece of history for the long-read pile. Secessionists in America’s South were convinced that Britain’s mills could not survive without their cotton. They had not reckoned with how adaptable an economy under strain can be. (Engelsberg Ideas)

Combat Experience as a Strategic Resource: Lessons of the Red Army Purges: How Stalin’s purges gutted military expertise, and what that teaches about institutional knowledge — History with uncomfortably current echoes:  “Instead, at its core, a central question is their impact on the combat effectiveness, indeed the lethality, of our armed forces. I take up this question through the lens of a case study drawn from one of the most consequential instances of rapid military leadership depletion in modern history, the Red Army purges of 1937-1938 and their effects on its performance during the conflicts that followed. My central proposition is straightforward: Operational experience, especially in combat, is a strategic resource, a form of military capital that takes decades to develop and that can be squandered in months.” (Just Security)

David Foster Wallace and Democracy. Despite the relative obscurity of even successful writers, especially those most regarded for literary fiction, Wallace continues to generate conversation sixteen years after his death. In the immediate aftermath of his suicide, the literary press, his most enthusiastic and loyal readers, and many journalists beatified him. His college commencement speech, a brilliant call for empathy later published as a booklet, This is Water, served as evidence of blessed intercession. Thus, those mourning from afar nominated the late author of the contemporary masterpiece, Infinite Jest, for sainthood. Hollywood cooperated, releasing an interesting, even moving, but also cartoonish film. (Liberties)

Hamptons Billionaires Call These Doctors for ‘Boat-tox’: For everything from aesthetic touch-ups to 9-1-1 emergencies, the wealthy are calling on providers who charge membership fees ranging from a few thousand dollars to six figures a year (Wall Street Journal)

A Terrible Thing Happened to My Family: Buttigieg writes personally about a family ordeal. Whatever you make of the politics, it’s a reminder these figures are people first. Even in today’s climate, there should be one fundamental principle everyone respects: whatever you think about someone in politics, you leave their kids alone. (Pete Buttigieg’s Substack)

This Cell Feeds, Grows and Reproduces. And It’s Manmade. Scientists build a synthetic cell that does the things living cells do. A genuine landmark — and a fresh set of questions about where the line sits. We have long dreamed of discovering the alchemy by which chemicals can be turned into life. On Wednesday, a team at the University of Minnesota announced that it had taken a major step toward that vision.  (New York Times)

On the origin of continents: Continental drift is as fundamental to geology as natural selection is to biology. Why did it take us hundreds of years to discover it? Why Earth has continents at all, and what that has to do with life. Deep-time science writing at its most satisfying. (Works in Progress)

Where the Light Falls: Who was Johannes Vermeer? Clare Bucknell on Vermeer and the mystery of his light. Art criticism that makes you want to stand in front of the paintings again. (Harper’s Magazine)

Video of the day: How this helicopter survived 1004 days on Mars, then disappeared

Be sure to check out our Master’s in Business this weekend with McKeel Hagerty, CEO/Chairman of Hagerty Specialty Insurance. He transformed a family specialty-insurance agency into an enthusiast-driven platform focused on collectible cars, events, valuation data, and auctions. HGTY is now a public company that insures everything from classic cars to boats, trucks, tractors, and military vehicles for over 2.8M collectors.

 

Summer gets more expensive

Source: Bloomberg

 

Sign up for our reads-only mailing list here.

~~~

To learn how these reads are assembled each day, please see this.

 

The post 10 July 4 Reads appeared first on The Big Picture.

10 Friday AM Reads

Three-day (or longer) weekend! Kick it off with our morning reads:

5 things mosquito experts do every summer to avoid getting bitten: Looking for pest prevention strategies that work? Researchers share how they prevent mosquito bites and keep the bugs at bay on their properties. Practical seasonal advice from the people who study the bugs for a living. File for May through September. (Washington Post)

The US is better off than it was in 1976. So why does it feel worse?America’s 250th birthday feels bleak. The numbers tell a different story. A bicentennial-to-now ledger that complicates the declinist mood. More fuel for the great why-are-we-so-grumpy debate. (Vox) see also Is America celebrating the wrong anniversary? John Adams thought so. The Founding Father anticipated “Pomp and Parade” to mark America’s birthday. But Adams didn’t think it would happen July 4. he was sure July 2 was the date that mattered. A fun bit of founding-era pedantry, perfectly timed. (Washington Post)

The world added nearly a million new millionaires in 2025 — but most people got poorer: Global personal wealth rose 10.8% last year, the fastest pace in years, yet median wealth fell in most markets. (Quartz)

What are the rules on insider betting, really? It’s more interesting than you might think. As betting markets expand, the line between edge and cheating gets blurry. (Financial Times) see also Will Betting on Wildfires Lead to Arson?: Prediction markets meet moral hazard in the American West. A genuinely unsettling question about what happens when you can profit from catastrophe. (High Country News)

World Cup visitors are losing their minds over these American foods From ranch dressing that converts Swedish fans on the spot to Carolina BBQ ribs that a Scotsman says ruined all other meat forever. Foreign fans discover the strange delights of the U.S. concession stand. A fun sidebar to the tournament’s culture-clash coverage. (Quartz)

You don’t have to swallow frogs: Klein and Coates show that if you don’t know what your core beliefs are, you’re going to get played. A contrarian riff on the productivity-guru gospel of doing the worst task first. Sometimes the frog can wait. (Degenerate Art)

Influencers: Turns Out, They’re Not So Influential at the Ballot Box: The failed campaigns of Jack Schlossberg and Spencer Pratt suggest it takes more than social media—and name recognition—to win an election. (Vanity Fair) see also We Need a Way to Prove Personhood Online: As bots flood everything, the case for verifiable humanity gets more urgent — and more fraught. A thoughtful take on a genuinely hard problem. The growing number of AI agents roaming the internet will eventually force us to verify what the old web mostly presumed: that there is a morally and legally accountable person somewhere in the chain. (NOEMA)

The Wheels Are Coming Off Putin’s War: The case that Russia’s war machine is finally sputtering, Crimea included. Read it against the Telegraph’s Kyiv piece for the optimistic read on the front. (The Bulwark)

Trump’s focus on his construction projects has increased, Post analysis finds: The president mentioned his planned White House ballroom, golf course changes and other projects on more than 75 percent of the days in June. The Post counts the days he brought up his building projects. A small, telling measure of presidential attention. (Washington Post)

A giant telescope goes on a decade-long search for dark matter: The Vera C. Rubin Observatory hopes to illuminate with a decade-long survey of the universe that began Monday night. By taking a comprehensive time-lapse of the sky over the Southern Hemisphere, the telescope will create an open dataset of unprecedented scale and detail for astronomers — and for the public — to zoom in on for further investigation. Inside the instrument built to chase the universe’s missing mass. A patient, well-illustrated look at long-horizon science. (Washington Post)

Video of the day: Your Brain is Making Reality Up | NOVA

Be sure to check out our Master’s in Business this weekend with McKeel Hagerty, CEO/Chairman of Hagerty Specialty Insurance. He transformed a family specialty-insurance agency into an enthusiast-driven platform focused on collectible cars, events, valuation data, and auctions. HGTY is now a public company that insures everything from classic cars to boats, trucks, tractors, and military vehicles for over 2.8M collectors.

See which 7 cities could soon see record-hot days and nights

Source: Washington Post

 

Sign up for our reads-only mailing list here.

 

The post 10 Friday AM Reads appeared first on The Big Picture.

At The Money: Building a Bond Ladder with ETFs



 

 

At The Money: Building a Bond Ladder with ETFs (July 2, 2026)

How can fixed-income investors create diversified, inexpensive bond ladders using Exchange Traded Funds?

Full transcript below.

~~~

About this week’s guest:

Steve Laipply is Global Co-Head of iShares Fixed Income ETFs. Previously, he was Head of U.S. iShares Fixed Income Strategy. He helps to oversee more than a trillion dollars in bond ETFs. Each week,

For more info, see:

Masters in Business

LinkedIn

~~~

 

Find all of the previous At the Money episodes here, and in the MiB feed on Apple PodcastsYouTubeSpotify, and Bloomberg. And find the entire musical playlist of all the songs I have used on At the Money on Spotify

 

 

 

TRANSCRIPT:

At the Money: Building a Bond Ladder with ETFs
Steve Laipply, Managing Director, BlackRock; Global Co-Head of iShares Fixed Income ETFs 

BARRY RITHOLTZ: Investors who are looking for yield, especially in an uncertain rate environment, used to need millions of dollars to build out a bond ladder in a separately managed account. It wasn’t easy. There were issues of credit quality, duration, and risk. It made it kind of complex to do. But today, you can create a simple ladder using inexpensive ETFs.

I’m Barry Ritholtz, and on today’s edition of At the Money, we are going to explain how and when to build your own bond ladder.

To help us unpack all of this and what it means for your portfolio, let’s bring in Steve Laipply. He’s Managing Director at BlackRock and Global Co-Head of iShares Fixed Income ETFs. Previously, he was Head of U.S. iShares Fixed Income Strategy. He helps to oversee more than a trillion dollars in bond ETFs.

Let’s start with the basics: What’s the problem that a bond ladder is supposed to solve for investors?

Steve Laipply: This gets to a very popular, longstanding practice that advisors and investors have used for years, which is this idea of: I’m not going to be able to really predict the evolution in interest rates, and so what I’m really interested in is cash flows. I’m interested in trying to line up some certainty with income, and I don’t really want to take a lot of interest rate risk.

A comfortable thing is to create a ladder, which means you buy some amount of bond exposure in every year going out to, say, five years. And if you’re worried that interest rates are rising, you could always just not reinvest and let that ladder roll down, get your par value back at maturity, and then you could take that cash and go elsewhere.

And so that’s always been a comfortable thing — this idea that I’m in control; if rates rise, I don’t have to worry about a perpetual loss from having an open-ended exposure. I can just let the bonds roll down to maturity and I’m done. That’s sort of the idea.

Now, in practice, many, many advisors and investors simply roll over and over again and just keep putting bonds into that last rung. However, it’s this idea that they have control, and I think that is a very attractive thing.

If you contrast that, for example, with a mutual fund or an SMA or an ETF, that may be more of a perpetual, open-ended exposure, and then there’s a sense that, well, maybe I’m less in control of managing that. So the attractiveness of ladders: cash flow, and you have some certainty and control over how it evolves and plays out. And that’s why they’re so popular.

BARRY RITHOLTZ: So let’s delve into that a little bit for people who are not familiar with the ladder. Let’s say we’re building a seven-year ladder: We’re going to have different duration holdings for each of those seven years, because we have no idea what rates will be in year three, in year six, and however far out you want to go. And so if you’re doing a 10-year bond ladder, well, you’re only taking a risk with one-tenth of that portfolio each year. And when it comes up, you get to decide: Do you want to just roll it over to more of the same? Do you want to adjust your credit risk, your duration, even where you’re investing? So you’re always locking something in. If rates go up, you get to reinvest higher. If rates go down, well, the rest of your portfolio is now worth a little more, but you’re going to get a lower yield.

Tell us about the products that exist so that you could either do this in, let’s call it, seven separate holdings, or just one holding with the ladder built in.

Steve Laipply: Yeah, and this is what’s fascinating. There are a couple of things to unpack here. So investors can ladder by going out and buying individual bonds, and that’s what they’ve done for many, many years. The downside of that is that depending on the amount you have to work with, you might end up being fairly concentrated if you start out with a smaller amount of proceeds, because, as you know, bond face value is a thousand dollars, and so you may not be able to build out as many holdings per year as you’d like to be diversified. But the advantage of that is: Okay, I know each individual bond and I can watch it mature, et cetera.

Another approach would be something that we pioneered back in 2010, which is what we call an iBond, which is meant to be sort of like an individual bond exposure that matures in a given year, but it can hold hundreds of bonds within that year.

BARRY RITHOLTZ: So fully diversified, in other words.

Steve Laipply: So you’re diversified tremendously relative to just trying to pick individual bonds for a certain year.

Let’s say you buy a five-year corporate iBond: All those bonds will mature in year five, but you may have upwards of 300 bonds, and so that gives you comfort in terms of the credit risk.

Now, the trade-off with that is that it doesn’t quite look like an individual bond, because you have many bonds, and so your cash flows won’t quite be as fixed or certain as they would be by holding an individual bond. But it’s roughly the same idea. It’s more akin to holding a portfolio of bonds maturing the same year.

BARRY RITHOLTZ: What are some of the other advantages of building a ladder with ETFs? Clearly, diversification is one. What about pricing, execution, and complexity? What are the other advantages?

Steve Laipply: And these are the trade-offs.

 

You have sort of the standard ETF features and benefits: You have exchange transparency, you know the price, you can sell out of it at any time.

Just to put this into context, imagine if you were holding a five-year ladder of individual bonds, and let’s just say you had the proceeds to build a pretty diversified portfolio for each year. Imagine trying to sell all those bonds if you decided you needed to raise cash. That would be a non-trivial exercise, and it might be quite costly.

With something like an iBond — let’s just say you decided to liquidate the entire ladder — you get the benefit of the ETF liquidity, just as you would in a traditional investment-grade ETF like LQD or what have you. There are varying degrees of liquidity, of course; some things may not trade as liquid as others. But the point is that that’s an ETF feature.

The other part of it is just really understanding what you own, and the ability to trade cheaply relative to individual bonds. ETFs trade for bid-ask spreads of pennies on exchange; individual bonds can be multiples of that. So that’s sort of the final thing — it’s about cost. Of course, ETFs have expense ratios, so you have to do that trade-off, but generally, the math is going to work out in your favor.

BARRY RITHOLTZ: The expense ratio, especially for iShares, is really quite reasonable. But let’s talk about maturity selection. You could build out a ladder almost as far as you want. How should people be thinking about why five years or seven years or 10 years? What goes into that selection process?

Steve Laipply: A couple of things. If you look at the tools — for example, we have tools on iShares.com that allow you to build a ladder — it shows you how to build out to get a certain yield, or if you want a certain duration profile, et cetera. So it really gets down to a couple of things: What sort of overall yield and income profile are you looking for? The other part is, what kind of cash flow profile are you looking for? Is there a particular reason that you want to go out to five years or greater? Do you want to be inside of three years because you may want that cash sooner?

Let’s take a simple example. Let’s just say you have a life event coming up in three years. You want the last cash flows to be coming due in those three years for sure. You can have cash flows coming due past that, but it’s far more comfortable to know that you’re getting that cash back in year three, because at that point you’re going to take a big trip, you may have college tuition due, etc. And so it makes it really easy to think of it in that way: When do I need that cash? Let’s just work backwards from there and build it from there.

BARRY RITHOLTZ: Let’s talk a little bit about the tool you have on your website, the iShares ladder builder with iBonds ETFs. It’s really kind of fascinating. You put in a dollar amount, what type of bonds you want — corporates, Treasuries, TIPS, munis, high yield — and you could go out as far as 2056. That’s amazing — that’s a 30-year bond ladder — and it gives you a whole bunch of different data on this. Are people using this sort of tool to construct their own ETF bond ladders?

Steve Laipply: They are. It’s proven to be a very popular tool. And that’s one of the, I think, interesting and neat things about having these products at your disposal. Again, when you’re building these ladders — let’s just say you build a pretty robust multi-year ladder — you’re effectively buying thousands of bonds, depending on the sector, let’s say corporates. And so that would be very, very hard to do just doing it in individual bond space, and it would be more expensive. And so the tool is something that allows you to visualize that and play with it. You can mix different exposures, et cetera. And so I think that’s something that investors have found to be really, really interesting.

BARRY RITHOLTZ: Let’s talk a little bit about credit quality. I’m old enough to remember when we used to refer to high-yield bonds as junk bonds. If you’re putting together a bond ladder, how do you think about juicing the returns a little bit with some high-yield paper?

Steve Laipply: This gets to, investor preference?

High yield by definition is what it sounds like. However, it comes at a cost, which is you may not get all of that money back, because some of it may default. And so that’s the rub, right?

I think investors are going to do sort of a calculated risk assessment on what they’re willing to tolerate risk-wise. If you put all of your money into a high-yield ladder, the yield will most certainly be higher than investment grade. However, the overall performance may not match that initial yield, because over time, some of those companies may default, and you may not realize exactly the initial yield you did — it’ll be something less. And so that’s just with any high-yield bond, right? I think what makes it attractive in the ETF space is that at least you’re diversified. And so that’s an important point, because if you’re trying to do this in individual bond space, you have a lot more risk to those individual companies than if you did it in ETF space.

BARRY RITHOLTZ: Right. You get to hold so many more individual bonds within the ETF than even a million-dollar portfolio is going to be able to do. One of the things that’s always interesting is when bonds begin to approach maturity, sometimes the trading is a little counterintuitive. What should investors expect in the final year of any particular bond ETF in their ladder? How should they expect this to trade? What happens on maturity?

Steve Laipply: Yeah, and this is, I think, something that investors are very, very interested in, because with an individual bond, it’s pretty easy just to watch, right? You know, okay, it’s one year left, it’s three months left, and then on the final day I’m going to see the thousand dollars hit my account. With a bond ETF, what’s going to happen is not all those bonds mature on the same day or in the same month. So let’s take a full calendar year. You may have some of those bonds start maturing in January. What happens to those? Well, they eventually get reinvested into cash accounts. In some cases they may get reinvested in very, very short corporate paper, as an example. But ultimately, as bonds keep maturing throughout that year, they’re all going to be reinvested in cash. And so by the end, you have cash in the bond ETF portfolio. What’ll then happen is the bond ETF delists, it gets liquidated, and that cash then hits your brokerage account. And that’s basically it.

BARRY RITHOLTZ: So, final bond ladder question: What do you think are the biggest mistakes investors tend to make when they build bond ladders? I see all the time people chase yields, they take a little too much credit risk, they don’t really think about duration — although I guess you don’t have to if it’s a fixed-year ETF — and then the other risk is the money hits as cash and then it just sits in the account too long. What do you see as the biggest problems?

Steve Laipply: I think some of it might be the reaching for yield. Because, again, why are you laddering? What are you trying to accomplish? And so I think the best thing to do is always really sit down, figure out what your goals are, and then work backwards. So as an example, that life event that we were using as an example earlier: Let’s just say you have to have that cash — you’re probably not going to want to do a high-yield ladder, right? You may want to do a Treasury ladder or a TIPS ladder, an inflation-protected ladder. You’re probably not going to want to swing for the fences on that one. The other one would be really just trying to understand the reinvestment part of that. What do you do when you get one of the rungs maturing? Do you go out and put it into a longer rung? Are you going to take that cash and reinvest it in a money market account? That’s investor preference, but it matters for your total return. So that’s going to be up to you. But I really do think working backwards from your financial goals is the best way to build a ladder. And then you can do that across the different asset classes. If you can earn more income, by all means, you might want to tilt more towards more credit-intensive assets. Safety is Treasuries and TIPS. And so I think that’s kind of it.

BARRY RITHOLTZ: So Steve, some people just like to go out and buy the entire Agg, the entire index. What are the differences you see between buying the whole index versus doing a ladder?

Steve Laipply: Well, you know, Barry, this is really interesting, actually, and it’s kind of a math question. But if you look at the behavior of index funds compared to just, say, a very simple ladder — where the investor takes the maturing proceeds and goes back out to the longest rung and reinvests, and they just do that over time, over and over and over again — that does not actually look too different than an index fund. It really doesn’t. And there has been academic research on this, and we can make it complicated, but the bottom line is perpetual laddering is kind of like indexing. And I think that’s sort of fascinating. And so if somebody knows they want to do that, they could also look at an index fund as well. But I always thought that was a really interesting thing if you line them up side by side.

BARRY RITHOLTZ: Huh, that’s really kind of surprising. I would imagine the ladder gives you a little more certainty into what your yield is going to be, whereas with the index, you’re just taking a wild guess.

Steve Laipply: I think both give you some level of certainty. The ladder is about control, right? Because you can decide at any time whether to stop reinvesting, and I think that’s why they’re really popular.

BARRY RITHOLTZ: Hmm, really interesting stuff. So to wrap up: In an uncertain rate environment, investors who have either future financial needs or liabilities that they know can manage around that by using a bond ETF ladder and reinvesting continuously over the cycle of that ladder. I’m Barry Ritholtz. You are listening to Bloomberg’s At the Money.

~~~

~~~

Find our entire music playlist for At the Money on Spotify.

 

The post At The Money: Building a Bond Ladder with ETFs appeared first on The Big Picture.