Billion dollar failures, and billion dollar success | Tom Conrad (Quibi, Pandora, Pets.com, Zero)

Tom Conrad is the CEO of Zero and on the board of Sonos. He began his career in engineering at Apple, where he helped build key features that remain in iOS today. Tom was previously the VP of Product at Snap and the chief technology officer of Pandora. He also held leadership positions at notable tech flops Pets.com and Quibi, giving him a unique perspective not only on what it takes to build a successful company but also on lessons from failure. In today’s conversation, we discuss: • Lessons learned from the infamous failures of Pets.com and Quibi • Lessons learned from the successes of Apple, Pandora, and Snap • Advice on choosing where to work • Understanding the math formula of a business • How to avoid burnout • Why Tom says not everyone needs to be a founder • What he’s building now — Brought to you by Coda—Meet the evolution of docs: https://coda.io/lenny | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc | HelpBar by Chameleon—the free in-app universal search solution built for SaaS: https://helpbar.ai/lenny/?utm_source=lennys-podcast&utm_medium=sponsorship&utm_campaign=helpbar-launch-lennys-podcast Find the transcript at: https://www.lennysnewsletter.com/p/billion-dollar-failures-and-billion Where to find Tom Conrad: • X: https://twitter.com/tconrad • LinkedIn: https://www.linkedin.com/in/tomconrad/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Tom’s background (04:40) Landing a gig at Apple (07:41) Pioneering the blinking folder design on iOS (11:04) Advice on choosing where to work (12:43) The importance of trusting your gut when it comes to people (14:05) Lessons from failed ventures (17:32) Why and how Pets.com shut down (18:30) How Tom’s experience at Quibi renewed his passion for building (28:48) Takeaways from Quibi and why it ultimately failed (31:42) Failing is okay (35:04) Tom’s career at Apple (39:11) Lessons from You Don’t Know Jack (40:24) Lessons from building Pandora (48:24) Looking back at Pandora and what could have been done differently (55:17) How Tom became VP of Product at Snapchat (1:01:31) Tom’s philosophy on being involved as CEO (1:05:51) Tom’s current role as CEO of Zero, and what he’s learned along the way (1:10:37) How Zero builds product (1:18:33) Advice on work-life balance (1:27:22) Contrarian corner: why not everyone needs to be a founder (1:30:08) Lightning round Referenced: • Ron Lichty on LinkedIn: https://www.linkedin.com/in/ronlichty/ • 11 reasons why Quibi crashed and burned in less than a year: https://www.theverge.com/2020/10/22/21528404/quibi-shut-down-cost-subscribers-content-tv-movies-katzenberg-whitman-tiktok-netflix • Meg Whitman: https://en.wikipedia.org/wiki/Meg_Whitman • Jeffrey Katzenberg on LinkedIn: https://www.linkedin.com/in/jeffrey-katzenberg-4b3b47123/ • John Sculley on LinkedIn: https://www.linkedin.com/in/johnsculley/ • Flickr: https://www.flickr.com/ • How Pandora Soothed the Savage Beast: https://www.fastcompany.com/3001052/how-pandora-soothed-savage-beast • Joe Kennedy on LinkedIn: https://www.linkedin.com/in/joe-kennedy-329417/ • Why Did Yahoo Pay $160 Million for Musicmatch?: https://www.wired.com/2007/07/why-did-yahoo-p/ • TikTok Is the New TV: https://www.wired.com/story/tiktok-new-show-tv-takeover/ • Evan Spiegel on X: https://twitter.com/evanspiegel • Flashtags: https://lane.substack.com/p/flashtags • Patrick Spence on LinkedIn: https://www.linkedin.com/in/patrickspence/ • The Philosophy of Ikigai: 3 Examples About Finding Purpose: https://positivepsychology.com/ikigai • The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life: https://www.amazon.com/Subtle-Art-Not-Giving-Counterintuitive/dp/0062457713 • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Hyperion: https://www.amazon.com/Hyperion-Cantos-Dan-Simmons/dp/0553283685 • A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285/ • Mrs. Davis on Peacock: https://www.peacocktv.com/stream-tv/mrs-davis • Watchmen on HBO: https://www.hbo.com/watchmen • Lost on Hulu: https://www.hulu.com/series/lost-466b3994-b574-44f1-88bc-63707507a6cb • Eartune replacement tips: https://eartune.com/products/eartune-fidelity-ufa • Charles Eames’s quote: https://www.brainyquote.com/quotes/charles_eames_169188 • Compuserve: https://www.compuserve.com/ • Steve Wilhite: https://en.wikipedia.org/wiki/Steve_Wilhite Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  There's this belief that everybody needs to be a founder. I think in some ways, our industry would be much better off if there were fewer founders. I use an entire category of smart, creative, hardworking, talented, you know, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never going to go anywhere. That would be so much better off finding a team that needs their skillset and working on a problem that has a mathematical formula that's going to win on any metric, whatever metric you care about. You want like the acclaim of your peers, you want financial reward, you want outsized impact on culture, whatever, whatever the thing is that gets you out of bed every morning.

• 0:43Speaker 00

  You can, you can achieve that in collaboration with others. You don't have to be the person that raises the seed round.

• 0:52Lenny Rachitsky?

  Today, my guest is Tom Conrad. Tom was an engineer at Apple, CTO of Pandora, which he helped take from zero to 80 million users. He's also VP of Product at Snap, where he was the right-hand man to Evan Spiegel for two years. He's been on the board of Sonos for over seven years. He's also part of two infamous product failures. Quibi, where he was chief product officer, which raised over $2 billion and died less than a year after launch. He was also a senior engineering leader at Pets.com, which famously went from nothing to a public company to completely out of business in 19 months. Today, Tom is the CEO of Zero Longevity Science, which is on a mission to extend the lifespan and the health span of the human race.

• 1:34Lenny Rachitsky?

  In our conversation, we dig into what Tom's learned from these famous product failures, also what he's learned from the many product successes. Tom also shares what he's learned about how to pick where to go work and what to avoid, how important understanding the math formula of the business model is, also lessons on burnout and health and leadership and contrarian corner. With that, I bring you Tom Conrad after a short word from our sponsors.

• 2:01Lenny Rachitsky?

  This episode is brought to you by Coda. You've heard me talk about how Coda is the doc that brings it all together, and how it can help your team run smoother and be more efficient. I know this firsthand, because Coda does that for me. I use Coda every day to wrangle my newsletter content calendar, my interview notes for podcasts, and to coordinate my sponsors. More recently, I actually wrote a whole post on how Coda's product team operates, and within that post, they shared a dozen templates that they use internally to run their product team, including managing the roadmap, their OKR process, getting internal feedback, and essentially, their whole product development process is done within Coda. If your team's work is spread out, across different documents and spreadsheets, and a stack of workflow tools, that's why you need Coda.

• 2:46Lenny Rachitsky?

  Coda puts data in one centralized location, regardless of format, eliminating roadblocks that can slow your team down. Coda allows your team to operate on the same information and collaborate in one place. Take advantage of this special limited time offer just for startups. Sign up today at coda.io/lenny and get $1,000 startup credit on your first statement. That's c-o-d-a dot i-o slash lenny to sign up and get a startup credit of $1,000. coda.io slash lenny. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers, and crafting a strategy, you're drowning in spreadsheets and roadmap updates,

• 3:31Lenny Rachitsky?

  and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and roadmapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds, and it's all built on Jira, where your engineering team's already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from Finance. Anyone that you want can contribute ideas, feedback and insights in Jira

• 4:15Lenny Rachitsky?

  Product Discovery for free. No catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny.

• 4:40Lenny Rachitsky?

  Tom, thank you so much for being here. Welcome to the podcast.

• 4:44Speaker 00

  Thank you. It's so fun to get to be a part of this.

• 4:46Lenny Rachitsky?

  I thought it'd be fun to start with a story about your time at Apple and you building this now very ubiquitous feature of dragging and dropping something into a folder, which is how you tweet about or talk about it. And the fact that it's still around, could you just share that story and maybe a lesson from that experience that you've taken away?

• 5:05Speaker 00

  Sure. So, let's see, I was 15 years old when the Macintosh came out. I remember really clearly, my entire, you know, teenage years, like all I wanted to do was to move from Columbus, Ohio to Cupertino and work for Apple. And my, you know, my, my heroes were that team of people that were had like, you know, written their signatures on the inside of the Macintosh. We cracked open the first Macintosh case, you would find the signatures of the 20 people or so who worked on the Mac. And that was like, that was my only ambition, truly. And then this was a period where like, no one wanted to work for Apple. I mean, that wasn't a thing. And it seems like maybe a little obvious today, but it wasn't an obvious ambition at all back then. So anyway, I went to

• 5:48Speaker 00

  college. So I wanted to do, study computer engineering at University of Michigan. And as we talk about my career, it's just over and over and over, I'm going to say, you know, an incredibly lucky thing happened. And the first incredibly lucky thing that happened for me in my career probably was that University of Michigan like happened to be a place that Apple recruited from. I didn't know that when I chose the school, but it made it reasonably easy to connect to hiring a manager at Apple. And I wrote an actual letter and put it in an actual envelope and put it in the mail and got an internship and drove out in my dad's Pontiac from the Midwest to California. Spent a summer interning.

• 6:29Speaker 00

  And my, my last day of the internship, I was thinking about really what I wanted to do when I came back, hopefully came back to Apple after I graduated. I had worked on a product that became shipped, it was called Quick Draw GX, it was early kind of second generation rendering system for the Mac. I'd been that team's intern for the summer, but what I really wanted to do is I wanted to work on the Finder. Like, this is the only thing in the whole world I really wanted to do. And so I went and found Ron Lichty, who is the manager of the Finder team and said, I, you know, I graduate in 10 months. I'd, I'd love to be a part of your team. And I think he was kind of like, well, why are you coming and talking to me now?

• 7:09Speaker 00

  You're literally going back to Michigan tomorrow. So I go back to Michigan in May, the phone rings and Ron says, "The college recruiting department just told me that I have like a college hiring rec. And if I don't use it by tomorrow, I'll lose it." So he's like, "I can't even interview you. You can't meet the team, but you know, you're basically a freebie for me. So do you want this job?" So just insanely lucky moment, got this job. So yeah, I get to Apple in the summer of 1992. And I have a laundry list of things that I would like to do to make the Finder more, you know, usable.

• 7:53Speaker 00

  And I remember sitting in Ron's office and saying, you know, you know, at the grocery store when like you're carrying bags of groceries out, like the door is like automatically open for you. I think like the Finder should do the same thing when you're dragging an icon around and you want to like, put it in a folder, you should be able to kind of look, you know, hover maybe over the folder icons and drill down into the file system to get to where you're going. And then when you drop the, the file, like all of the, the folders that opened up between you and your source and your destination would close for you. Ron thought that was a fine idea. And so that was the way Apple worked in those days. I just went off and started, you know, coding that up. And

• 8:38Speaker 00

  I got to the point late one night, 2:00 in the morning, I'm at Apple, no one else is there, where I needed some kind of animation to indicate that the folder was about to open. And I'm certainly not an animator, and I certainly wasn't going to do anything awful in the middle of the night. So I just wrote some code that blinked the folder, like selected, unselected, selected, unselected, five times, and thought, oh, I'll get, you know, one of the really talented visual designers to do something much more interesting.

• 9:10Speaker 00

  Long story short, Apple finally shipped that feature like four years later. It sat in the source code repository forever while we did other things. And when it shipped four years later, it blinked five times. Roll the clock forward six or seven years, macOS X comes out, entirely new Finder, rewritten from scratch, no spring-loaded folders anywhere to be seen. People complained about it. It got re-implemented. So all of the code, brand new, folder blinks five times when you hover over it. Roll the clock forward another decade, iOS comes along, and they added folders. And when you drag an icon around, it blinks a few times.

• 9:51Speaker 00

  I'm not sure what the point of this story is, other than maybe it's something about, I think we all do this as designers and product people, we take these shortcuts that we think that will go back later and clean up. And sometimes, I mean, it's literally been 30 years, you know, that little design detail like lingers, you know, three implementations later, and now it's just a part of the way that these Apple products work. Pretty bizarre.

• 10:16Lenny Rachitsky?

  As you were talking, I'm on a Mac right now, recording this, and I just did it just to make sure it's still there. And it is indeed still there. I think it blinks three times and then just opens up for you.

• 10:25Speaker 00

  There you go.

• 10:26Lenny Rachitsky?

  Full engineers got royalties on features they build that continue to live on in our product.

• 10:30Speaker 00

  Okay, I'll tell you like just one other little thing to like center you in time about what the Finder was like in 1992. We didn't get royalties, but our names were in the About box. Like you would go to About the Finder, and like the seven of us, there were seven engineers at Apple that worked on the Finder. Like our names would scroll by, you know, the Finder, copyright 1992, you know, yada, yada, yada, one name after another, totally different era.

• 10:55Lenny Rachitsky?

  It feels like you got kind of what you wanted with the names scribbled on the motherboard.

• 10:58Speaker 00

  For sure. I've gotten, I've gotten a lot of the things I wanted as a kid.

• 11:04Lenny Rachitsky?

  So kind of along the same lines, I want to talk a bit about picking where to go work. Clearly, you had a sense you wanted to go work at Apple. Over your career, you've landed at a lot of really successful places. You've also landed at a lot of very famous failures that we're going to talk about. What advice would you give people for helping them pick where to go work based on your experience?

• 11:25Speaker 00

  When I was a kid, my ambition to work at Apple was entirely about the product. And so probably that version of me would say, "Find a product that you're passionate about and like go spend your time and energy on that thing." Pretty quickly, you learn that an awful lot of your development and day-to-day satisfaction really comes from the people that you get to collaborate with. Can you learn from them? Do you like them? Do they challenge you in the right ways? Do they give you latitude in the right ways? It's so much about not just what, but who. And so for a very long time, my advice would have been entirely in the category of like, "Find something that you love with people that you think are amazing,

• 12:09Speaker 00

  and the rest will kind of take care of itself." And interestingly, I have been lucky enough to have some things that were successful on the metrics that get talked about the most, big audiences, big financial return, et cetera, et cetera. And I've also worked on some things that were really notable disasters. When I look back on my career and think about the things that I've done, my professional satisfaction is not well correlated with those external metrics and very, very coordinated with, "Did I love the thing we were building? And did I love the people I was working with?"

• 12:43Lenny Rachitsky?

  Following the thread of the people, I think one of the hardest things is really knowing what the people are like until you join. I think as a chief product officer, joining or VP of product, you have a lot of time that you spend with the team. Most people don't. They have an interview and then they're like, "All right, I gotta make a decision." Do you have any advice for how to help people get a sense of if the people are the kind of people they want to work with?

• 13:03Speaker 00

  I think people are really, really good at this. I mean, every single time I've taken a job where it turned out that I was working with people who had a different set of values or working styles than I had, I knew. And you tell yourself that... At least in my case, I tell myself a story about why the thing I suspect, you know, might be the case, you know, isn't the case, but you know, I mean, you do this in your personal life all the time, right? You meet people out at dinner, so you get seated next to them at some industry event or something, and sometimes you come home and say to your partner, "Oh, my gosh, the person next to me was just the worst."

• 13:46Speaker 00

  And then sometimes you're like, "I think I made like a permanent lifelong connection with this total stranger who just happened to sit next to me." Like, you know.

• 13:55Lenny Rachitsky?

  It's like a very simple piece of advice that I think people don't fully appreciate is just like, trust your instinct, trust your gut.

• 14:01Speaker 00

  Yeah.

• 14:01Lenny Rachitsky?

  Just pay attention to what comes up when you're around people at a certain company. Okay, so you brought up this phrase of notable disasters, and I want to talk about that. You worked at two of the most famous notable disasters of product companies, Pets.com and Quibi. I think it's really rare someone sees the inside of so much hype and then such a fall at a company. And so I just want to spend some time in these two areas. And maybe the way to set it up is just what's a lesson you took away from each of these two experiences that you've taken with you to future work? And maybe advice you share with people?

• 14:37Speaker 00

  Probably the biggest lesson, it's not really about like the specifics of the business. The biggest lesson really is these things make you better. They, in some instances, actually, I think in both instances, they became kind of dominos that opened doors for me in my own ambition and my own sort of, you know, professional life that maybe just wouldn't have opened at all if I hadn't gone to those companies and learned those things and had those experiences. And frankly, even in the case of Pets.com, like even the high-profile nature of it, I could have worked at, you know, one of a thousand ecommerce websites in 1999. And when I went on to some subsequent job interview or something and talked about my experience, people were like, "I would have never heard of the thing that you worked on."

• 15:21Speaker 00

  But everybody certainly heard about Pets.com. It's a pretty funny example, too, of how some struggles are like timeless. You know, that was 2023, 24 years ago now. And

• 15:36Speaker 00

  While as a leadership team, we made, I'm sure, all kinds of mistakes. One of the things that happened was that there were three kind of overfunded pet e-commerce sites. And we all raised in excess of $50 million, which is a tremendous amount of money now, was a tremendous amount of money then. And we all thought it was a zero-sum game and that we, as one player, started to spend on promotion or to spend irrationally on national broadcast television advertising, we all did. And it became this kind of unwinnable arms race.

• 16:20Speaker 00

  So there was like, I think, a fundamental lesson about the, like, the, you know, having an excess of investment can be its own albatross or lead you to take, make decisions that maybe would be unwise. And then, of course, it's just like, you know, timing is really important. You know, Chewy is an online pet store worth $9 billion today. They were a private company and bought by PetSmart and then spun back out. But when they were bought by PetSmart, they were acquired for $3 billion. You know, biggest e-commerce acquisition of all time. And while I think it's probably unfair to compare Chewy, who executed exceptionally

• 17:02Speaker 00

  well over a decade, grew their business brick by brick and turned it into something really remarkable, to Pets.com, which was, you know, in a very, very different moment in time and tried to go to market in a really different way. The critique that is often leveled at Pets.com, or at least at the time, was like, this is just a stupid business. They're shipping dog food around. You could never make that work. And like, that, that's just wrong. Like, you absolutely can't make it work. Probably can't make it work when 80% of the country on the internet is still on dial-up. It was really, really early.

• 17:32Lenny Rachitsky?

  I saw a stat, I think you shared somewhere, that you took Pets.com from nothing to a public company to completely out of business in 19 months.

• 17:40Speaker 00

  Yeah, yeah, that's about right. You know, the, the other thing that's forgotten in the tale is that we...

• 17:49Speaker 00

  We actually didn't go bankrupt. We shut the company down and returned the remaining balance to the investors, which no public company had ever done before. And the leadership team just like reached the conclusion that, given the way market conditions had evolved, there was just no way we were going to be able to get more capital into the company. And it was a company that required additional investment to get to profitability. And so it was better to sort of wind down early, take the money that we had in the bank and get it back to investors than to just spend every last penny on like a, you know, what was sort of a fruitless attempt to salvage it.

• 18:28Lenny Rachitsky?

  Did not know that. Let's talk about Quibi. What went wrong there? Do you think there was a path to Quibi? Having worked out, any big lessons that you took away from that experience that you bring with you?

• 18:39Speaker 00

  The kind of miraculous thing about Quibi for me was it relit my enthusiasm for the industry for doing this work. I had left in, I think it was December of 2018, and I thought that maybe I was just done making software. I had done it for a really long time, and that's like 25 years or something. And I had changed a lot. The industry had changed a lot. And I thought maybe I just didn't have the same passion for it that I had, you know, a decade before. It also seemed like maybe it would be fun to have like another chapter of my life that was just completely different. And I had a whole

• 19:23Speaker 00

  list of things that I thought I might want to do. I mean, they were really, they're kind of ridiculous. It's like, maybe I want to be a pastry chef. Maybe I want to be a landscape photographer. Maybe I want to, you know, learn to make bad music to put up on SoundCloud or something. And really, the only thing they had in common were they were all things that I knew nothing about. People would be like, oh, you think you might want to be a pastry chef? Do you like to bake? And I'd be like, no, I didn't know anything about baking. You know, oh, you might have landscape photography. Do you take photos? No, I don't make photos. But I was kind of committed to the bit, actually to the point where when TechCrunch interviewed me about my departure from Snapchat, I was like, you know, I'm out. I'm going to do something else entirely. That story is very much out there.

• 20:02Speaker 00

  But a few months after my last day at Snap, I got a call from Meg Whitman and Jeffrey Katzenberg, who were starting up, it was called NewTE at the time, and you know, the pitch was, we're going to try to take the best of mobile and Silicon Valley and consumer tech and sort of weld it to the best of sort of Hollywood-style content production to build something like completely bespoke and purpose-made for consumption on the phone. They were looking for both technology leadership and product leadership and wanted to know if I was interested in one or both. And I took the meeting, even though I wasn't really taking these kinds of calls from anybody, it just seemed

• 20:46Speaker 00

  like who's going to pass up the opportunity to have lunch with the two of them. So I listened to the pitch and politely declined and told them that I was going to be like a pastry chef or something. And we kept doing that every couple of months for like seven months. We'd go to lunch, they would give me an update on the progress they were making, and I would decline, the invitation to get involved somehow. And then, late in that year, I went to lunch one more time, and Meg explained that they brought on someone to lead technology, and they brought on another person to lead product, and both of them, for really, truly, for reasons that are

• 21:28Speaker 00

  completely disconnected from Quibi itself, both of them had left after about six weeks.

• 21:36Speaker 00

  And Meg's like, "We've raised all this money, and we've told the world that we're shipping this product in about a year. We've got an awful lot to do, and I really could use some help, and I would like consider it a personal favor if you would come and spend just a couple days a week helping." You know, she's like, "I'll continue to look for someone who actually wants the job, but it would really be, it'd be, you know, great if you could help me get this off the ground." And my wife is a freelance writer, marketing strategist, and...

• 22:06Speaker 00

  Loves her life as a freelance contributor and she's like, you should do this. Like, why not? It's two days a week. It's just a few months. What's the worst thing that could happen? Like, maybe, maybe you'll like it. And, and I'm like, no, the worst, here's the thing that will happen. Like, I won't do it two days a week. It will like immediately be three days, then four days, then five days, then six days. Like, I just know myself. And she's like, no. She's like, you know, just on Wednesday night at six o'clock, close your Quibi laptop and be like, all they're paying me for is for Tuesday and Wednesday, and then open it back up on Tuesday morning. Like, that's all you've got to do. Well, you know, she's right about most things, and she's wrong about this. I fell deeply into it right away.

• 22:49Speaker 00

  And it was just so fun to get to build a team from scratch and to design and build a product from scratch and to take advantage of all of the sort of modern software architecture stuff that had come into being over the course of the 15 years since we had started Pandora. And, you know, I'm, I'm, I'm embarrassed about, about some of, of what happened with Quibi for sure. But I'm super grateful for the experience because I just really fell in love with the industry again and was reminded of just how rewarding it can be to, to build something and, and to try to put it out there, even if, even if you stumble pretty mightily along

• 23:34Speaker 00

  the way.

• 23:35Lenny Rachitsky?

  Is there something that you took away from that experience that taught you what to try to avoid, what to try to pull towards?

• 23:43Speaker 00

  I think I sort of misunderstood or misjudged companies sometimes by thinking about them, like, really focused on the, on the, the product execution. You know, kind of, if you find an interesting problem that people, you know, people care about, and you, you solve that problem in a really beautiful, elegant, delightful way, that's 10 times better than, than anything else that they can get in that same space. They'll tell their friends and like, all the rest will sort of take care of itself. And so that was always my ambition. Find a thing that I cared about building. Do a great job building it a really delightful way. Go really deep on listening to people and their feedback and iterate your way to success

• 24:26Speaker 00

  and sort of breaking through that membrane that we all strive to get across the, you know, kind of really great word of mouth. But I think the thing I've come to better appreciate is that companies are also kind of like a, they're kind of a math problem that describes how you take, you know, investment and pour them into the equation and out the other side comes returns on some time horizon. And yes, there are variables in that equation that are influenced by the product that you build and all of the little details and decisions that you make about making that product great. But if the equation is fundamentally broken or a big swing in and of itself, no amount

• 25:11Speaker 00

  of like iteration and execution can like kind of get you out of the failed outputs of the broken equation. And I think, you know, Quibi made a bet that you could build an entirely bespoke content library that was sufficiently scaled to get people to subscribe and retain for a couple billion dollars. I mean, it's a huge amount of money, but you know, we made, we made 70 shows in 18 months, which is like more content than all of the major broadcast networks combined

• 25:56Speaker 00

  made in a single year. So it's a pretty major accomplishment. And we made a bet that we would augment those sort of episodic and serialized or Hollywood style shows with a bunch of daily content that we produce at the level of like network television, nightly news and so forth, that would be an alternative to some of the sort of daily content that you might otherwise get on YouTube.

• 26:22Speaker 00

  And that was going to be about a third of the content spend. One like super interesting thing that no one talks about is that all of that content was designed to be made like day of or day before it aired. So there was no back catalog of it. And it was all designed to be shot in these professional studios that we built out. And it was really expensive. Like I said, it was like a third of the of the investment we were going to make in content. Maybe half, almost half the investment we were making content. And we launched two weeks into COVID and we couldn't make any of that content, except literally in the garages of the host's homes. And so we had this thing that was supposed to seem like really set apart from YouTube

• 27:05Speaker 00

  that literally now was being made exactly like YouTube content, which is sort of like self-produced at home with, you know, very little sort of the support infrastructure of Hollywood. Now, you can argue, I mean, I think the content on YouTube is really, really exceptional in this category. And maybe we were never going to do better than that. But I think what was really fundamentally broken with Twitty was that the actual foundational equation of can you make enough premium content that's totally bespoke and made for the service and takes advantage of the unique nature of the phone? Is that enough content to get people to sign up and retain? And can you do that for a couple billion dollars?

• 27:48Speaker 00

  And I think the answer is no. The library has to be much, much bigger. And you have to have, like any company, you have to have sufficient time and energy to iterate on the content format itself because we were really, our roadmap really wanted to innovate on the content format. And so I think part of what happened is pretty quickly it became clear that the math was just wrong. It wasn't going to take 2 billion. It was going to take 6 or 8 or 10 billion. And the risk reward profile of betting 10 billion on the format was just more than than anyone can stomach.

• 28:27Lenny Rachitsky?

  Wow, I really like this metaphor and this mental model of the math formula of the entire business and thinking of it that way. I knew COVID changed the way people consumed content and that hurt Quibi because I think it was meant to be on the go, not like sitting at home where you could watch anything you want, but also the fact that the content couldn't be made as well as you were hoping to make.

• 28:46Speaker 00

  Yeah, for sure. Yeah.

• 28:48Lenny Rachitsky?

  As a CPO, one of the biggest challenges is pushing back, trying to convince the founders of their mistakes, of convincing, of doing what they want and just powering through it and dealing with it sometimes. I guess, is there anything you think you could have done, looking back, or is the math formula set up for failure from the beginning and it's probably just not going to work out, almost no matter what you did?

• 29:10Speaker 00

  One of the bets was that we weren't going to just use the apparatus of Hollywood to like, make the content. In part, we were going to use the apparatus of Hollywood to market the content. So, you know, Jeffrey had recruited this incredible rolodex of the world's, literally the world's most famous celebrities to make shows for Quibi. We kind of had like, everyone either made something for launch or was going to make something. And like, part of what they were going to do is like, turn up in culture and talk about their shows. I mean, we've heard a lot in the last six months about how hard it is to market movies because the stars can't

• 29:51Speaker 00

  go out and talk about the movies during the strike. There was this theory that you could apply the marketing sort of technique of Hollywood to get 20, 30 million people into the theater on like, opening weekend for Quibi. And that was always like, a very, very audacious take, I thought. Like, you know, Uber has all the money in the world to experiment with paid user acquisition and they're not consistently a top 10 most downloaded app in the App Store. But the theory of Quibi, like the math of Quibi, like, did require us to like, from day one, land in the top 10 and stay there forever. Like, the model would have worked

• 30:36Speaker 00

  if we could do that. And to the Hollywood marketing apparatus, the numbers that it takes to get there felt kind of small. You know, if you can get 20 million people in to see Shrek on opening night, new IP, like, surely you can get them to take their money out of their pocket and download this thing and start a free trial. Now, those of us who've spent our life in Silicon Valley making software and, you know, really, really tried to get people to show up and, you know, download new IP in large numbers know just how hard that is. So maybe if I critique my own contribution to the math equation,

• 31:15Speaker 00

  maybe I should have beat the drum a little harder about just how unlikely it was that we were going to land the kind of distribution in month one that the model sort of required. I, I, I've had it, if I had to go back and do it again, I think I would spend maybe more time investing and, and illuminating that aspect of the digital universe.

• 31:41Lenny Rachitsky?

  That is such a good takeaway of just showing the leaders, here's the data, here's the assumptions that we're all betting on. And do you believe this can happen? And they probably would have said, yes, this will happen. I'm so confident.

• 31:55Speaker 00

  What made it hard was it wasn't structurally impossible. Like if you had to be bigger than any app that had ever been made,

• 32:07Speaker 00

  then you could probably make the case it's impossible. But since you only sort of had to land in the top 10, like you couldn't quite say it was impossible. You could just say it was highly improbable. And maybe one of my mistakes was, I guess, I imagined that we would launch.

• 32:27Speaker 00

  And when the likely thing happened that we, you know, got

• 32:33Speaker 00

  millions of people to download the app, which we did. And then that was we, when we inevitably struggled to, you know, retain those users in, at, you know, at, at high percentages. I mean, retained it's sort of what I think of as like a good industry starting point, but, but we weren't setting any records on retention. I just imagined that what would happen next is like the thing that happens in all young companies. You would iterate, you would like grind on the funnel until a year later, two years later, six months later, whatever it is, you, you figure the formula out to get people in and get them to stay and get them to retain. And

• 33:15Speaker 00

  But I didn't appreciate was like just how quickly you go back to the foundational math. And then the math really says like, you just can't, you can't spend two years iterating your way on, you know, optimizing the funnels like you would in a startup that had a different cost structure. Like in a world where you have to spend, you know, a billion dollars a year making content. You just can't afford to not be a hit.

• 33:40Lenny Rachitsky?

  I think it's also important to just remind us, it's okay for these things to happen. Like people take a bet, as you said, we're going to try this thing. Here's our bet, here's our experiment, we're betting on this sort of format and this business. We're going to raise money from investors that know they might lose all their money. And it sometimes doesn't work out, you know, it's like, it's part of the game.

• 33:56Speaker 00

  It's certainly, certainly painful to take money from investors even if they know what they're doing and to not get them a return. I feel a real responsibility to investors to do better than we did at Quibi. But yeah, I mean, there is a risk reward thing that goes along with these investments. And part of the reason I get, you know, all the riches on the upside is that they're going to, they're going to bet on some quibbies along the way too.

• 34:18Lenny Rachitsky?

  So as you were talking, you said that it was called New TV and that sparked a memory. And I searched my email and I actually got an email from a recruiter in 2018. We just kicked off a very special executive opportunity, the CPO at New TV, New Venture in Los Angeles with Jeffrey Katzenberg and Meg Whitman, raising a billion dollars, working with top talent. Are you interested in exploring this opportunity?

• 34:41Speaker 00

  Lenny, Lenny, Lenny, your story could have been so much different.

• 34:46Lenny Rachitsky?

  You could, this could have been Tom's podcast. Lenny, tell me about what happened at Quibi.

• 34:50Speaker 00

  I would take, I would take that trade.

• 34:53Lenny Rachitsky?

  I don't know, there's pros and cons. They even sent this whole PDF, a TV in your pocket, New TV. Amazing. All right, I'm going to read through this and see, see what they pitched back in the day. Okay, let's move on to things that worked out really well. Well, it's called notable successes, other products you worked on that worked out great. So I'll list a few of them. And maybe what might be helpful is just, we'll just go through each one and share what you took away from that experience, lesson you learned from working on those products. And the ones that come to mind for me are Snap, Pandora. Apple, if we want to go there. Also, you built, I don't know exactly what you did there, but you worked on, you didn't know Jack, this game that I loved. It's, I think if you're

• 35:36Lenny Rachitsky?

  an elder millennial, you're just gonna like, oh my God, I love that game. I just, I don't even remember it exactly, but I just remember the visceral feeling of playing that game and it was so much fun. So that's cool. I didn't know that you worked on that. And then there's also Sonos, which you're on the board. So whatever order you think might be most interesting, just going through those. And what did you learn from that experience?

• 35:56Speaker 00

  I worked at Apple in the interval where Steve was gone. John Sculley, that kind of period. So System 7, System 8, Power Macintosh, like that, that whole era. And we were doing a lot, we, you know, we shipped a bunch of great hardware. We transitioned the company from Motorola 68,000 CPUs to the Power PC architecture. But particularly in that transition, we really struggled to ship consumer software features. I mentioned that, you know, I wrote three little folders and some other consumer features, like in my first six months at Apple, and they shipped four years later, actually after I'd left the company. I was a little surprised they were still in the software repository even candidly. But I'll tell you

• 36:41Speaker 00

  that one of the things like culturally about Apple in that moment was at least I felt like a person was really rewarded if they could make a kind of broad contribution across functions. So if you were, you know, a talented software engineer, but also a thoughtful product designer, and maybe also had interesting input on product marketing, that you could build a really great reputation inside the company by playing all of those positions a little bit day to day. And so when I left Apple after four years, I look back on my time, I didn't ship as much

• 37:26Speaker 00

  software as I had hoped. And I felt like a little bit like a professional gadfly. I was like, you know, six miles wide and like a centimeter deep. And

• 37:38Speaker 00

  I went to the work for this company called Berkeley Systems. They, in addition to you don't know Jack, they made the Flying Toaster screensaver, if you remember. Oh, my God. You remember the 90s. How could you forget that? And when I met them, they were kicking off this game development for this trivia game. And we're looking for someone to lead the technical team. And so I joined as technical director for the You Don't Know Jack franchise, managed a team of engineers. And it was a completely different culture than what I was used to at Apple. It was certainly the case that I was welcome to weigh in on the game design or the, you know, the, the marketing or some other aspect of the deliverables.

• 38:23Speaker 00

  But my job was to build the software on time, you know, with high quality, period. And like, if I did those things, I'd be rewarded. And if I didn't, like, I would not be successful. And no amount of insightful feedback on the gameplay or the packaging or whatever else I might want to do was going to benefit me and my career at all. And it was such a blessing to be forced to go deep on something because I, you know, I spent a lot of time developing chops as an engineering manager, but I also wrote a ton of software. And that's really honestly when I became a software engineer. Like my college education was insufficient to get me there.

• 39:07Speaker 00

  And the amount of software I wrote at Apple was insufficient to get me there. But I came out of my Berkeley Systems, You Don't Know Jack experience, like feeling like I could really hold my own technically in a way that just wouldn't have happened. And so I do think that there's something to be said for a culture where there are swim lanes and people are encouraged to be like really, really exceptional in their lane. And

• 39:32Speaker 00

  So I feel really lucky that I stumbled into You Don't Know Jack when I did. And it was also, I mean, it was the first thing that I worked on that had just like, like huge cultural, you know, awareness for a couple of years. I mean, it's crazy. They're still making sequels. It has been nearly 30 years. And there are, there are versions of You Don't Know Jack that's are in, you know, all of the stores and the PlayStation Store and Xbox Store, in the iOS Store. You know, you can play new versions of You Don't Know Jack to this day. It's crazy.

• 40:06Lenny Rachitsky?

  Did not know that. I see the website now and it's a little different, but basically the same.

• 40:13Speaker 00

  So I'd say my lesson for, you know, my, my, my lesson from, from You Don't Know Jack was definitely like, it really does pay to get good at something and not just be a generalist. And then, I mean, you know, Pandora, it was, was quite the next thing that happened after You Don't Know Jack was Pets.com. And then after Pets.com, there was Nuclear Winter in the industry. And I worked in enterprise software for a while. And after Nuclear Winter, I had this idea that I was going to build a destination for music discovery on the web. And I'd been doing enterprise software. The consumer internet was like nonexistent for those years, early aughts.

• 40:54Speaker 00

  And, but around 2004, things started to thaw a little bit and you started to hear the first signs of the companies that would came to call web. 2.0, like Flickr would have been one of the, the early examples. And one of the enterprise software things I did was a personalization recommendation engine that used a vector space. It's like a lot of the things that we're talking about now in AI, you know, albeit 20 years ago. And so I knew something about recommendation systems in the enterprise space. And I was super passionate about music. I'm not a musician, but I was that kid in college who would corner you and be like, oh, if you like this band, I gotta play this for you.

• 41:35Speaker 00

  And, you know, stereo until you would like beg to leave. And so I had this idea that like, maybe I can use the internet to do that at scale. Not with just one person, but with, you know, hundreds of thousands of people or millions of people, maybe introduce them to music that they would love, but otherwise would miss out on.

• 41:53Speaker 00

  And I promised that I was gonna tell stories about luck in my career. There's been a gazillion of them, but one really dramatic instance of that is I I was sort of biding my time to exit this enterprise software company. I was VP of Engineering, a whole team that reported to me. I felt a lot of responsibility to exit in a responsible way. But I was really excited about this, this digital music company that I was gonna start. But I wasn't telling anyone at all because I didn't want to get back to the team. So I, I flew down to Los Angeles to go out to Coachella in 2000, in the spring of 2004,

• 42:34Speaker 00

  and completely randomly, like physically bumped into a guy that I had gone to high school with on the polo field. And hadn't seen him in a decade. And the thing that we had in common at high school was we loved music. And so I tell them the story of like, I'm gonna start this company to do personalized digital music on the internet. And he said, there's this woman I work with who just left our company to move to Oakland to work for this little company called Savage Beast that like are also doing something in music recommendation. Do you wanna talk to them? And I said, sure, why not? So I got introduced to Tim Westergren, who was the founder of Savage Beast. Savage Beast was like a seven or eight full-time employees at that point.

• 43:19Speaker 00

  They made a music recommendation engine that they licensed to other companies to put in consumer products. So Savage Beast's customers were Best Buy, who put it in kiosks, and AOL, who used it in the AOL Music website. And they were looking for a VP of Engineering. And I got the offer, thought about it a little bit. I declined because it was kind of this B to B to C thing. And I really wanted to do something in consumer, I had an idea about the app. And like a month later, they called again and said, you know, I keep talking to people who really think that you're the person. And interestingly, one of the main reasons they thought that I was the person is they were really impressed by the fact that I had run engineering at Pets.com.

• 44:02Speaker 00

  So, I mean, it's just one of those things where like these things do pay dividends even when they're a disaster. And honestly, in like, in like, what I would really say was like, almost like a lapse in judgment. I said yes, even though it wasn't, it wasn't the product that I wanted to build. And I won't bore you with all of the details, but like 90 days later, after some like, you know, typical early-stage founder drama stuff, the founding head of technology and product had resigned, completely unrelated to my arrival. And the company had a new CEO, Joe Kennedy, and Joe had this idea for what he called a one-click personal radio. And Joe is a product marketer

• 44:46Speaker 00

  and just the best CEO in the whole world. We spent 10 years together building Pandora. And he sort of gave me the keys and just said, like, as long as it fits the brief one-click personal radio, like, it's all yours. And I got to, you know, I had to build the team and the culture, you know, in collaboration with him and Tim, the founder, over the course of the next 10 years. And, you know, it's just every, every, every good thing. So, I mean, there's just a million, billion lessons from Pandora. I mean, everything I am as a product leader and an engineering leader comes from, from things that happened at Pandora. But maybe

• 45:24Speaker 00

  the thing that I think of first is, I think we met our early audience in like, an incredibly genuine way. For example, when we launched, the [email protected] was an alias for all at pandora.com. So if you sent a customer service request to Pandora, every single person in the company received it. And because we had no, we made a decision to have no customer support team in the first year, the expectation was that whoever sees the, the request first should respond to it. And so, you know, you would write to us and you would get the founder, or you'd get me, or you'd get the engineer who wrote the feature, or you'd get the CEO.

• 46:06Speaker 00

  And there were no, there were no macros to like, respond to, to, to a commonly asked question. There was, there was no read the FAQ. There were, and there were no rules about what you could and couldn't say. If the person's like, I think this feature is like stupid and broken, we would encourage people to say like, you know what, I think you're right. And I'd like, really struggling to get our stupid head of product to agree with me. Would you, you know, I'm going to CC Tom and maybe we can convince him that, you know, this was a bad decision. And we did all of that because we thought one of our like, superpowers as a young company was that we could just like, Engage with our audience like as real human beings, not like as a shiny brand that was trying to,

• 46:47Speaker 00

  you know, you know, be something that we could just never be like this is this this period is where the iPod and iTunes are at the peak of their powers. And so, you know, there was no way we could sort of out Apple, Apple on the brand front. And so we were just ourselves. And I think it really, really was a catalyst for the the word of mouth that developed around Pandora and like, we never spent any money on paid user acquisition, like literally no dollars the entire time I was there because people love the product and they told their friends about it. And that's how it grew.

• 47:21Lenny Rachitsky?

  I saw a stat that you grew Pandora from zero to 80 million users from 10 employees to 3,000 employees from zero, basically to a multi-billion dollar company. So

• 47:31Speaker 00

  We did those things.

• 47:32Lenny Rachitsky?

  Not bad.

• 47:32Speaker 00

  Did. We also, I mean, I think my product stewardship, like in some ways, set the scene for Spotify to walk through the the digital streaming door and like show us the exit. So Pandora is, you know, it's, I mean, I, again, such a privilege to be able to have worked on something that that touched and continues to touch 10s of millions of people's lives every month. But it's bittersweet from the standpoint that that I think we had an opportunity that we, you know, in some ways we misplayed.

• 48:06Lenny Rachitsky?

  My mom is still a huge fan of Pandora, uses it every day for whatever it's worth.

• 48:10Speaker 00

  I mean, it's still going and then there's like the numbers are still 10s of millions of people in the US listen every month. So it's a it's a thing. But yeah, it's, I mean, it's, it's a little sad that it didn't, it didn't have the quite the staying power that some of these other things that have come along since have.

• 48:25Lenny Rachitsky?

  Just on that topic, do you think there's something that you could have done, someone could have done? Do you think there was an opportunity to become Spotify? Or is it the business model, the math formula was set up in such a way that it was nearly impossible?

• 48:37Speaker 00

  One of the things that was tough for Pandora was that when we started it, digital music was like a category that no investor wanted to touch. You know, it's lawsuits, it was, there was no money to be made. There were relationships with the labels that were completely impossible to nurture. And there had been no big outcomes, like the biggest exit in digital music when we got going was Yahoo had bought Music Match for like $400 million. And so that was seen as like kind of the ceiling on the opportunity. And you know, along the way, we found investors who believed in our vision and invested, you know, ultimately hundreds of millions of dollars in the company over its pre-public years.

• 49:18Speaker 00

  But there was never like a investor enthusiasm for the company and the category that was anything like the investor enthusiasm that a company like Spotify enjoyed just six, seven years later. Snap enjoyed for, you know, its, you know, pre-public tenure. And, you know, I think part of it was different in for Spotify is that the comps were not Music Match at 400 million, they were Pandora at 8 billion, but even above that, they were, you know, Netflix at 100 billion. And so investors just had this new sort of optimism about what you could do in subscription and in streaming and, and, and, and, you know, Spotify really played that to their advantage

• 50:02Speaker 00

  in a way that we couldn't because we had gone public and the public market investors were still trying to, you know, figure, figure us out. So we didn't have access to capital. It was very hard for us to, to, to take the same kind of risks that, that Spotify took. But then I think we just completely misjudged one really important thing, which is that we were really inspired by disrupting terrestrial radio. Terrestrial radio is like the predominant form of music consumption in the country. You know, people spend, I can't remember the exact stats, but it's like, you know, by minutes consumed, it's something like 10 times more music minutes a month on the, on radio in the aughts and early 10s than on owned music.

• 50:45Speaker 00

  And the advertising-supported sort of radio market was

• 50:51Speaker 00

  A $30 billion category and recorded music was $8 billion. And so we had this idea that we're going to reinvent radio and Spotify and Audio and Apple Music and like the 14 other, Rhapsody, which was Spotify before Spotify, they were all going to chase this smaller owned recorded music opportunity and that, you know, we could be left relatively alone over here going after the less sexy but actually bigger market. And I think we just got it wrong.

• 51:35Speaker 00

  It should have, it should have been obvious that inevitably all of your music in any format was going to be delivered, you know, as a stream from the cloud and that the record labels in particular were going to, they were going to set the terms on what the structure was and the structure that they preferred was the Spotify structure. And we operated under a different licensing regime that they hated that was a statutory license that we got from the government. And it was exceptional, it would have been exceptionally risky for us to come out from under the statutory license and do direct deals with the labels.

• 52:16Speaker 00

  But it was a requirement to play in the world that they imagined as the future and we should have imagined as the future too. And eventually the company got around to it and, and, and that it was just, it was too late.

• 52:28Lenny Rachitsky?

  It's interesting that so much of this was rooted in that original vision that you shared of Pandora, the radio, smart radio in your pocket.

• 52:35Speaker 00

  Yeah.

• 52:36Lenny Rachitsky?

  One click for a car radio. Yeah. Personal radio that like you just stayed on that track even though there was this other track. But I think it's important to point out, you said it was like seven years later. And I feel like there's this interesting trend with the companies you've worked at, Pets.com and, and Pandora, they just too early, you just come too early at these ideas. And I feel like that tells me Quibi might still happen. There's a Quibi coming seven years from now.

• 52:59Speaker 00

  You know what's really, really funny about that? Just today, there's a headline.

• 53:05Speaker 00

  About a Hollywood produced show that's launching on Instagram reels and TikTok that was shot vertical and the headline is literally something like, is TikTok the new TV? And it's pretty funny that literally that's what Jeffrey and Meg called it when they were incubating the idea. I mean, I think it's pretty clear that that purpose-built video for mobile looks a lot like TikTok and I don't want to take anything away from from all of the innovation in that space that that they and the other players are driving that that Quibi didn't capture in its initial product definition. But I mean, you know, obviously, we stare at our phones consuming video of all kinds, you

• 53:49Speaker 00

  know, all day, every day. So there's, there's definitely something there.

• 53:53Lenny Rachitsky?

  The PDF that I mentioned that I got from the recruiter, the first page again says, you have a TV in your pocket. So it's exactly what they're pitching. That's amazing. All right. I think what I've learned, I need to bet all my money on this new Quibi clone because the timing is, timing might be right. This episode is brought to you by Helpbar by Chameleon, the free in-app universal search solution built for SaaS. Your help content lives outside your app and is scattered in many places, forcing users to waste time hunting for answers. Helpbar solves this. It delivers answers directly inside your app and eliminates context switching. Users can search or ask questions to get AI-generated answers and lists of the most relevant documentation from all of your help sources, including your knowledge base, docs, blog, and video

• 54:37Lenny Rachitsky?

  libraries. You can also use Helpbar to navigate your app and launch actions, such as scheduling a meeting or viewing an interactive demo. The best products today use Command K for in-app search and navigation. Helpbar makes that readily available within your app without engineering or new code. Give users a faster and more delightful self-serve experience that reduces friction and increases in-app engagement. Upgrade your user experience with this modern component and supercharge your product-led motion. Sign up for Helpbar today. It's free and easy to set up in minutes. Check it out at helpbar.ai/leni. That's helpbar.ai/leni.

• 55:17Lenny Rachitsky?

  Let's talk about Snap briefly and then I want to have a couple more questions.

• 55:21Speaker 00

  At Pandora, I was the head of product and head of engineering and our CEO was brilliant, but he was a product marketer, kind of, I mean, he was, Joe was like all things. He was an engineer by education and a great marketer and a great finance person and like just such a, such a utility player at a very, very high level across every discipline. But he was also really, really good at letting his team do their jobs. He really let me run product and engineering. And so, you know, not only did I have tremendous latitude to make good and bad decisions about product, I also got really got a seat at the table to like, help lead the company. So rewarding, so gratifying, best professional experience that one could have.

• 56:05Speaker 00

  So I leave Pandora after a decade, I take like a year and try to figure out what I'm going to do next. But after about a year, I got introduced to Evan and it's kind of a funny story. A mutual friend sent this introduction over and then immediately responded and said, why don't you come down to Los Angeles and like have a coffee with me? So I fly down, it's not clear if it's a job interview or like what it is really. I mean, I was just like lightly exploring things that were out there and was a big fan of what he was doing with Snapchat. So I spent like 45 minutes with him and then I spent 45 minutes with the head of engineering and another 45 minutes like the head of legal.

• 56:48Speaker 00

  And then they tossed me into a conference room with like a dozen product designers, all in their mid to late twenties, many of which had gone to school at Stanford with Evan. I would come to learn like all really, really, really impressive, super, super talented people, but like, you know, it was just like 10 of us sitting around a conference table. And it wasn't really clear that they knew why they were talking to me, but we had kind of a, you know, hour long, free ranging conversation and.

• 57:18Speaker 00

  So I left and I thought it was like, it was like a totally fascinating morning, but I wasn't sure what had happened really with these interviews. Like it all seemed very ad hoc. Is there a job opening? I guess it was a little odd and I, I went to lunch at Out of Kenny and got a text from Evan's admin saying, can you come back to the office? Have you gotten on your plane yet? I was like, I was just like ordering lunch. I'll, I'll, I'll just come back right away. So I go back. Now it's like one o'clock in the afternoon. This entire thing started nine o'clock in the morning. I sit down in the conference room. Evan comes in with a manila envelope and says, we loved you.

• 58:00Speaker 00

  We'd like for you to be our VP of product and like handed me a written offer. Like all the terms, like the stock compensation, the whole thing. I'm like, I'm gobsmacked. Like I'm, I'm, I'm, I'm flattered. Like this is like really playing to my ego. I like, I kind of can't believe that this company that feels like maybe the most interesting thing that's happening in consumer tech that, you know, they're, you know, notoriously brilliant and mercurial founder has like taken enough of a shine to me that he wants to like give at least some of the keys to the product kingdom over after such a short courtship. So I leave and, and when some of that buzz wears off, I start to wonder if there's like some red flag flags or maybe. So I tell Evan, listen, I'd like to come back and like meet more of the leadership team,

• 58:45Speaker 00

  spend more time with you, go a little deeper on what this means. And so we extend our courtship by another week or so. And I, you know, super impressed by the rest of the leadership team and the, the product thinkers and, and Delft designers and things that I was going to get to work with on a daily basis. And so I take the job full knowing that it's like going to be wildly different than Pandora. We had all of this latitude to like, kind of do whatever I might want to do. And in the, you know, the context of Snapchat, at best I was going to be Evan's kind of right hand, you know, a person that principally executed his vision. And, and that's certainly what it was.

• 59:30Speaker 00

  I mean, Evan and I ended up having like a really great collaboration. But it was certainly most days I was, I was executing on his vision, both at a high level and very much in the details. And Evan's truly brilliant. I mean, and he's also actually a really nice guy. I think in some ways he gets a bad rap for, he has very high standards, but he's, he's a very kind person in my experiences with him. But it was a super exhausting job and not as soul satisfying as I wanted it to be. And after a couple of years, I, like I said, I thought maybe I just wanted to like make

• 1:00:12Speaker 00

  croissants or something. But one, one really, really big, important lesson that I learned at Snap is about risk-taking. And like, when you have the, the financial support and the foundational relationship with your investors that Evan has, it really allowed him to take these really big swings. You know, acquire technology that he thought was game-changing, build features speculatively that maybe would be pruned in any other product or map planning process because the odds of them having an outsized impact were modest. And it just allowed him time after time to like make bets that paid off. And like, we forget about

• 1:00:56Speaker 00

  the ones that don't work, when there are so many home runs, you know, in those years. And we didn't have, environmentally, we weren't set up for that at Pandora. But I think in some ways, like I wasn't temperamentally inclined to those kinds of big swings. And I think I'm, I think I'm a, I take bigger risks and encourage bigger swings now because of things I learned from, from Evan and Snap.

• 1:01:18Lenny Rachitsky?

  That is an awesome story. It resonates a lot with what Brian shared about how he thinks about product now, which is kind of telling people kind of what to build versus very bottom-up, tell us ideas you have. Does that impact the way you run? We're going to talk a bit about you as CEO now, but I guess, do you have a place that you try to be of CEO as, here's what we're building?

• 1:01:40Speaker 00

  As a product-oriented CEO, like how much you should kind of lean in to the details versus set direction and create an environment where great people can do great work? I suspect there's not one answer that applies to every company stage, you know?

• 1:02:01Speaker 00

  When I was at Apple, one of the reasons that we struggled to ship things is that Apple did a great job of assembling incredibly, incredibly smart and talented people, just like everyone around me at that early stage in my career was so, so inspiring. But one of the side effects of that is we would get in a room and we would turn over some problem or opportunity and we would talk ourselves out of every good solution because it wasn't perfect. I used to joke that like Apple was like the only place in the world where like a vote of a thousand to one was a tie because that one person would be so thoughtful in their critique that the other thousand people would be like, hmm, that's right, that's right.

• 1:02:43Speaker 00

  And even though there's been this huge consensus of what the right answer was, we've got to talk ourselves out of making decisions.

• 1:02:49Lenny Rachitsky?

  That one wasn't Steve Jobs necessarily, it could be somebody else.

• 1:02:52Speaker 00

  He wasn't there.

• 1:02:53Lenny Rachitsky?

  Hmm, wow.

• 1:02:55Speaker 00

  So I think, I think what broke Apple out of that mode was Steve came back and like they didn't vote anymore. Right. You know, Steve was just making the call. And so I have some sympathy for Brian and Evan who have these big, you know, thousands of people working for them and as they delegate, they, they grow frustrated that there's not progress at the pace that they're looking for and that there's indecision and the people on the teams report that there's just like churn and no progress and there's fikdoms and politics and all the rest and that as the CEO, as a brilliant product oriented CEO,

• 1:03:39Speaker 00

  they are uniquely situated to come in and cut through all of that garbage and, you know, get the trains running on time again. Having said all of that, I also think that it can be a mistake to be that kind of leader in a smaller org because part of the opportunity of the small org is to, is to assemble a group of people that are incredibly talented, that believe in your mission and who you can easily influence with a much lighter touch and set them up to build a culture in an organization that can execute. And so I see. I see my job as CEO is to try to surf that edge of like, I'm really in the detail.

• 1:04:23Speaker 00

  So I deeply understand the business and the product decisions that we're making and the processes that we're using to run the business, but not overplay my hand with respect to dictating outcomes. The one we always have as CEO is no matter how much you tell the team that when I swing by their virtual desk and say, you know, I've been thinking about this little detail. It's not important right now, but like, what do you think? The, you know, it's like nine out of 10 times that person is going to go and start working on that thing. And so you do have to be just really careful about the way you engage in some of those details, I think.

• 1:05:06Lenny Rachitsky?

  There's a really good episode I had with Lain Shackleton from Coda, and he shared this framework called flash tags that they use at Coda, and I think it comes from HubSpot. You tell people, here's the, what this opinion is, is it an FYI? Is it a suggestion? Is it a do this? There's like four of them and one's like, I will die on this hill. You need to do this.

• 1:05:27Speaker 00

  I try to do a lot of that. I, I, I wish I could say that in my experience that that, that pays off. I, I, a lot of the time, even if I say very clearly, just one person's opinion, focus group of one, you know, don't change your priorities to go work on this. Like it has more of an outsized impact on people's behavior than I intended.

• 1:05:49Lenny Rachitsky?

  Easier said than done. Coming back to your journey, we've talked through the story up until getting to Quibi. But two years ago, you went in a whole new direction and you are now the CEO of a company called Zero. What is it like to move from just being a product leader and energy leader at a company to being the CEO for the first time? Why did you use Zero as that role? And what have you learned as CEO that you wish you knew as a product leader or energy leader at a company that listeners might find useful?

• 1:06:19Speaker 00

  It's been a really, really incredible couple of years. You know, in the aftermath of Quibi, I spent a lot of time, sort of as I'll do, sort of, soul searching about what I learned and what I might want to do next. And, you know, as I thought about it, I realized that I really wanted to move on to something where I could have like a direct impact on the culture and values of the company that I was involved in. I really, you know, got that opportunity at Pandora in a big way. And, you know, I had spent the five years of like Snapchat and Quibi, working for Evan and Meg and Jeffrey, who are all incredible business leaders, but have their own very specific sort of style and approach. And that leaves, you know, a mark on the culture that's unique to the founder.

• 1:07:04Speaker 00

  And then, as we discussed, like, I'm always really interested in, in building things that, you know, are near and dear to me. And I was particularly thinking about like, what can I do that could have like a really positive impact on the world in my next chapter? I've been with an awful lot of media stuff through the years, video games and streaming services and so forth. And it seemed like maybe there was something that was, had a little bit more weight to it that I could, I could spend my time on. And so, you know, my first thought was I would start something. So I had a company idea, I was kind of quietly workshopping for some months. And completely independent from all of that, it's, you know, eight months into the pandemic and my own personal health was at an all time low.

• 1:07:47Speaker 00

  I was 50 or 60 pounds overweight, my cholesterol is in the red zone. I mean, I was like out of breath climbing stairs, which is something that I had never encountered in my life before. I'm a bit of a yo-yo dieter and I'm always like kind of critical of my, like looking in the mirror, but I was never ever really worried about my health, my longevity. And suddenly I was. And so my solution to that was to like go really deep on metabolic health, like just like thousands of hours of podcasts and videos and, you know, glucose monitoring patches and Oura rings and digital fitness gear and just to try to understand, you know, the things that impact health and longevity. And, and.

• 1:08:33Speaker 00

  You know, as much as I would like to report that what I learned is that there's some like magic pill that you can take, maybe some like osilable rapamycin or something. The truth is, is that, that to live a longer and healthier life, you really have to attack what I would call metabolic disease, which you know, manifests in overweight, obesity, and prediabetes, and diabetes, and high cholesterol, and you know, all of these things that, that, that impact your, your long-term health. And so I found zero in this path, and was using it to, to help in my own sort of health journey. And Mike Mazer founded the company four and a half years ago, and he and I were talking in this interval about my own experience, the product, I was just kind of giving him

• 1:09:17Speaker 00

  product feedback and so forth, and he was telling me a little bit about his own entrepreneurial journey. And somewhere in the conversation, Mike said, you know, my intention is to step up into the executive chair role and to find a CEO for the company. So again, like in my story, just over and over and over, this incredibly fortuitous thing happened. You know, I just sort of knew immediately that it sort of ticked all the boxes, you know, here's a chance to, you know, lead something that already had some momentum, to impact the culture and values in a really direct way, and was like really, really close to my own personal journey. And so, we know, we've got a great little company, and 27 people, we've got more than a million users on the platform every month, over 100,000 of them pay us, tens of millions of dollars of revenue through the years.

• 1:10:02Speaker 00

  And you had double-digit growth, even coming out of the pandemic, when lots of health and fitness companies kind of saw retreats. And most importantly, it like, it actually works, you know, 75% of the people who, who use the platform, lose weight, and people lose on average 5 to 10% of their body weight in the first 60 days. And it, because of the success that people have, we grow just completely organically. We have no paid user acquisition at all. It's really a word of mouth business. But that's not to say that, you know, it's not challenging, all startups are challenging. And, you know, what we've really focused on for the last couple of years, is we've been really focused on unit economics, like really trying to understand, how much value can

• 1:10:47Speaker 00

  we derive and deliver, you know, for every person who downloads and, you know, installs the app? How do we, you know, convert them through all of the funnels efficiently, and get them engaged with the product, and get them to retain and sort of drive that up in a really systematic way?

• 1:11:02Speaker 00

  You know, I'm, you look at my whole career, I'm definitely a person who started off thinking software development was mostly in part form. You know, you find brilliant visionaries who have a deep understanding of human behavior, and they craft solutions for problems that other people don't see, and they make them delightful, and they get all the little details right. And, you know, when you found product market fit for the art, then you sort of optimize them through a really sort of quantitative sort of take. And so I'm definitely a person that sees both sides of that sort of left brain and right brain, you know, equation that's important in software.

• 1:11:44Speaker 00

  But here's the, here's the thing that's really, my eyes have really opened to in the last two years. While companies are definitely the software that they make and the products that they deliver, and that there is an art and science to that, as I described, there is also, if you step back, there is an equation that describes the business. It talks about like how you turn investment into returns. And I suppose I had come up through finance and been a business major, that maybe that's the way that I would have conceived of companies to begin with. Maybe it's a little embarrassing that I had to be 53 years old before I, like, the scales fell through my eyes, and I was like, oh, like, companies are equations.

• 1:12:24Speaker 00

  And so, you know, when we first started talking about lifetime value and customer acquisition cost and getting those two things balanced, and just the sort of thinking about the unit economics of the business, my natural instinct was to go immediately to sort of the leaf nodes of the equation, like, oh, what percentage of people do we convert from installed to registered, and from registered to trial, and these like very sort of way down at the bottom of all the funnels, and to like ask the product team, like, let's try to optimize these.

• 1:12:54Speaker 00

  And in the process, though, of trying to understand where we could take the business as we optimize those various dimensions and trying to understand, too, which of the dimensions had the most leverage, I started building these ever more sophisticated models that described the whole business. I mean, I've, I mean, in startups, you get to wear a lot of hats and definitely a hat that I'm wearing that I didn't anticipate at all as I am, I am the full-time FPNA guy for Xero. And so, you know, I built this, this sort of spreadsheet that aggregates data from all of our business intelligence tools

• 1:13:35Speaker 00

  and raw data from our subscription transactions and looked at all of our historical results and all of our expenses and spend and then could use that to predict future scenarios by sort of manipulating all of these variables. And I, it's just, it's just not at all the way I ever thought about products before. And, and I know that you've got lots of listeners who are like, this guy's an idiot like that. Yeah, this is a fundamental way to contemplate, you know, product work. But if there's anybody out there like me who sort of think, thought of it as art first and then sort of optimization in the details, it is really, really powerful to spend the time to create the model that describes the whole thing. So you can identify

• 1:14:19Speaker 00

  like, what are the high leverage points to focus on? So we've been doing a lot of that at the company in the last two years and it's really starting to deliver incredible results. You know, like everything in life, you just, I mean, you sign up for things where you can learn and, and that's the big one for me in the last year.

• 1:14:36Lenny Rachitsky?

  I really love that takeaway of as a CEO, coming back to share, here's what you should be thinking about that the CEO is probably thinking about as a product leader, you may not be, of trying to actually spend the time to think about the business model and understand it deeply because your founders are thinking about all the time. And so if you're not, you're missing out on like, here's a way to influence them. Here's a way to.

• 1:14:56Speaker 00

  It's so funny, too, because it's a thing, I suddenly understand something that mystified me through my entire career, which was I'd go to board meetings and, you know, the investors would ask these probing questions. But they were really never about the product and what the product did and what the product roadmap was and like what the features were and what this, you know, it was all, it all seemed to operate at this level that sort of was almost completely independent of the details of like the what is the solution you put into the world, which is a product oriented thinker was just completely baffling to me. And I like, I now realize that they were, they were tilling the soil that I'm talking about. They were tilling like what it, it doesn't really matter what the screens are, what

• 1:15:41Speaker 00

  the features are and like, you know, it, that certainly matters, but like if there's another higher order way to look at a company, which is really about the optimization of this equation. And I think particularly if you sit on 25 boards, it's probably a much more efficient way to evaluate how your companies are doing, where to spend your time and how to help by, by thinking about them abstracted up at that layer. So, you know, I will never stop thinking about software development as being an art form and I will never stop enjoying, you know, the days when I get to sort of lean in on the details, but, uh, but it's been, it's been pretty eye opening.

• 1:16:18Lenny Rachitsky?

  The other thing that stands out here, one is I think this is especially true for consumer subscription apps, which I've done some research on and basically they never work. There's Duolingo, there's Xero, which I didn't know how much scale you guys reached. My math here real quick. So you have a million users, a hundred thousand paying users. You charge like 10 bucks a month. I know there's a discount for an annual plan, but basically you're making somewhere a million dollars a month, which you don't have to confirm or deny it, but that's the math I just did. And that's crazy. So congrats. That's a rare successful consumer subscription app. It like never happens.

• 1:16:53Speaker 00

  And like I said, every, every time, every startup is hard and I never stopped being surprised at the, the new hard things that pop up every day, but, but we're, we're on a really great run. We've had a tremendous year and I'm just so, so proud of the team we've assembled. They're, they're incredible to the last.

• 1:17:08Lenny Rachitsky?

  Part of the reason you're so successful is exactly what you said, where there's a huge focus on LTV, CAC, the math formula, because for these sorts of businesses, that's the crux of it is can you acquire people? For less money than you need to spend.

• 1:17:21Speaker 00

  One thing that's really fortunate for for Zero is Mike Mazur, who founded the company, and I have both been sort of around the block long enough and enough times that, you know, we remember 2008, we remember 2000. And so in these moments, like kind of in the pandemic, you know, there were companies in our category that were raising hundreds of billions of dollars with the intention of sort of throwing it at pay user acquisition. And we made a conscious decision to to optimize the the value of the organic traffic that we were getting and to drive our growth through LTV expansion rather than top of funnel expansion, which was candidly not in fashion in, you know, 2021, 2022.

• 1:18:03Speaker 00

  Turns out it's much more in fashion these days as and as companies are are called upon to be much, much more capital efficient than they were during the pandemic era. And so, um, you know, it's, I guess I feel somewhat fortunate that my, you know, my, my natural inclination as an entrepreneur is more in sync with the expectations of the market than than it was for for a while.

• 1:18:27Lenny Rachitsky?

  Okay, so you've probably had the longest career arc of anyone I've had on this podcast. You've worked at all of these different companies in a lot of different phases. You're still at it, and I'm curious what you've learned about how to maintain your mental health and avoid burnout essentially through this journey. You mentioned you take some time off. Is there anything else you found, or is that is that a trick of just how to not burn out?

• 1:18:51Speaker 00

  Do you know this, this, this Japanese concept called ikigai?

• 1:18:55Lenny Rachitsky?

  Mm hmm. Yeah, but share it, share for folks that may not be familiar.

• 1:18:58Speaker 00

  So, uh, the idea is it's a Venn diagram, and there are four spheres. There's one, a sphere that's labeled what you love. There's a sphere labeled what you're good at. There's a sphere labeled what the world needs. And there's a sphere called what you can be paid for. And where they all intersect is this Japanese idea ikigai. It's like the intersection of what you're good at, what you love, what the world needs, and what you can be paid for. If you find that, it's a good guy. And interestingly, your, your listeners should go and find this because there are, there are interesting ways to label the other intersections, the intersections that where they all four don't come together. And

• 1:19:43Speaker 00

  And what's really interesting is that the ones that are three but not four, I think because they are, they're the ones that are like, close but not quite to this really satisfying thing. And so it's like, when you, you find those, it's really easy to choose a job or to choose a, a path where you have three but not four, which is a really great recipe for feeling like there's something just out of your reach that's really important. Anyway, it's a great framework to think about your life and your career. So to start, I'm incredibly lucky that like, it's all Igggy guy for me. Like what I'm good at, what I love, what the world gives, what I can pay for, like, they're just, they've always overlapped.

• 1:20:27Speaker 00

  And a big part of it is just like, what I love is this world. Like I, I love software. I love building software. I love writing software. I love using software. Like people are like, you know, what are your hobbies? And I'm like, I, I like, I don't think I have any hobbies. And I think about like, well, what kinds of things do I do on the weekend for fun? And it's like, you know, I'm like teaching myself After Effects or something, which I will immediately forget. But like, I, you know, I just, like, it's just sort of fun to go really deep on some piece of, of interesting software. So I'm very lucky. And so that, I think that has been super sustaining for me.

• 1:21:07Speaker 00

  You know, like one of the reasons I've been able to do it as long as I have without really burning out is that just like, it's what I do. And in some ways, it's why I come back to it. Like, it's easy to say I'm going to become a pastry chef, but like, left to my own devices. Like, I, I use software. I make software. It's my hobby. It's my, you know, passion. It's my, it's all the things. But a couple of thoughts about how one engages with their work.

• 1:21:36Speaker 00

  One thing is, I'm really not like a hashtag hustling kind of leader. I, I, there was a woman that I worked with on the Finder just out of college that left a really big mark on me. My own style of work then, I think I mentioned that my memory of like flashing, like blinking the folder animation was like a 2:00 AM kind of thing. I mean, I was 23 years old. I woke up at 11 o'clock in the morning. I, you know, went to the office. I screwed around and played, you know, video games in the Apple Arcade and went to a couple of meetings and had lunch and stood at the whiteboard and pontificated about some nonsense.

• 1:22:19Speaker 00

  And then about four o'clock every day, I would start writing software and I would write software until two or three in the morning. And then I would go out to dinner with the people from the team in the middle of it and whatever. And so it, it kind of looked like I spent 14 hours a day, six or seven days a week at Apple. And it was, I was really, I was celebrated for this. There were lots of nights where I would like work clear through the night and my, you know, boss would come in the next morning and be like, are you still here? And I'm like, I'm still here. Look at the school thing I did. And I got a lot of attention for that. And then there was this woman on the team who showed up every single morning at 8:30, sat at her desk, wrote a ton of great software and every night packed her stuff up and left. And she contributed more than I ever did.

• 1:23:04Speaker 00

  And I don't think she got the same kind of recognition that I got because of the way she did the work. And when we were building the team and culture at Pandora, I thought about her a lot and really made a point of saying that I just wasn't interested in like performative contribution, that it's the work that matters and what I want to celebrate is if you can show up and do it and go home and have other things in your life. Because I think that's a recipe for being able to do it on a sustained basis rather than kind of burning yourself out. I think there's some nuance in this. I think 22-year-old me was always going to want to work through the night. And so I think creating space that that's okay too is important.

• 1:23:49Speaker 00

  And I think maybe in some ways at Pandora, like it was almost like that wasn't okay. It was like, you should be taking more breaks. Why are you doing, going this hard?

• 1:23:58Speaker 00

  But I do try to create environments where people have like a reasonable balance between their regular life and their technology life, or room for that if they choose it. And I do think that that has, through the years, has helped me keep at it. But I still work a lot of nights and weekends because I love it. It's my, it's what I do. Here's the other thing. I got very, very lucky with the Pandora experience. I got this sort of, you know, outsized, probably inappropriate financial reward for being a part of it, and gave me options that I never imagined that I would have. And so I, after 10 years, I left and I didn't know what I would do, but I thought maybe,

• 1:24:39Speaker 00

  I mean, I really need, I did really need a break. It was a really hard job. And that was definitely a moment where I needed some time to recover. But I think if you had asked me on that first day, I would say like, I don't know why these people like find success and then like start another company right away. Like, why? Like, you know, so many things you could do in a while, why would you start another company? It's so hard. And I was particularly in love with the idea that I would like, I had access to experience. Like, I didn't really care about things. I wanted a fancy watch or whatever, a car, but I wanted to see the world, kind of. And so I thought, like, I'm gonna just go, and I'm gonna live in London for three months, then I come back to San Francisco for a month, and go live in Mexico City for three months. And like, I'm gonna just have this like

• 1:25:22Speaker 00

  life where I'm like soaking up experiences. And after doing that for six months, the thing that I came to realize is that, that what I care about way more than experiences is relationships. And like, if you're the, if you're the person who is constantly on a plane going, seeking out some new experience, like, it's really hard to form and maintain intimate, satisfying relationships. So I went back to San Francisco. Like, I can't be all over the world if I'm gonna like be engaged with, with friends and like-minded people. And you know what people do on Monday morning? They go to work.

• 1:26:00Speaker 00

  And so like, if you like, if you want to be engaged with humanity, like where they are on Monday morning is like at work. And so more than I had the itch to build things, which I do very much have, I had the itch to collaborate, to like be in the game with other people. So that was what took me to Snapchat, took me out of like chasing experiences and took me back to building again. And then, as we've already described, like, you know, I, I, I had a point, I thought, well, I care about like this, this collaboration, but maybe I don't, maybe it doesn't need to be software that I'm, that I'm creating in the world. And Quibi like gave me a chance to sort of fall back in love with that, that process again.

• 1:26:45Speaker 00

  And here we are, more software.

• 1:26:48Lenny Rachitsky?

  Plus being on a board of a hardware company. What you, what you just shared reminds me of Mark Manson's book, The Still Art of Not Giving a Fuck, where his, have you read this book?

• 1:26:58Speaker 00

  I have not.

• 1:26:59Lenny Rachitsky?

  Okay, it's like, uh, sold like a bazillion copies. And it's like, the core of it is that we get joy out of solving problems. And we think we'll be happy when we have freedom to do nothing. But it turns out, freedom is only helpful to help us discover the problems we just want to keep solving.

• 1:27:16Speaker 00

  Yeah, totally. I think that's exactly right.

• 1:27:19Lenny Rachitsky?

  Yeah, it sounds like that's the experience you went on. Last question, I'm trying to, this new segment, I'm going to call it contrarian corner. And the question is, is there something that you have a contrarian opinion about? Something that you believe that most other people don't?

• 1:27:35Speaker 00

  There's a segment in our industry that believes this, like, uh, very intensely, which is like, there's this belief that everybody needs to be a founder. And I think in some ways, our industry would be much better off if there were fewer founders. I think in some ways, the

• 1:27:50Speaker 00

  There's an entire category of smart, creative, hardworking, talented, you know, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never going to go anywhere. That would be so much better off finding a team that needs their skillset and working on a problem that has, you know, that doesn't like, as I described, the mathematical formula that's going to win, that has the market opportunity, that's like the right size, that like, you know, has the 10x thinking that can really,

• 1:28:32Speaker 00

  and, you know, I'm a little biased here because I'm, while I am CEO for the first time now, I've never been a founder and I've been lucky enough to find a bunch of young teams that could benefit from my, you know, skills and enthusiasms and sometimes to some success and sometimes to some embarrassment, but always really, really interesting. Yeah, if you're out there and you think that like, the only possible way you can be successful in this industry, on any metric, whatever metric you care about, you want like the acclaim of your peers, you want financial reward, you want, you know, like any of the things that people aspire to, you know, outside impact on culture, like whatever, whatever the thing is that gets you out of bed every morning, you can, you can achieve that,

• 1:29:15Speaker 00

  you know, in collaboration with, with, with others. You don't have to be the person that raises the seed round.

• 1:29:23Lenny Rachitsky?

  I 100% agree with that. I'm always telling people, don't start a company. It's super painful, very rarely works out. It's like so hard. I don't know what's harder, being a product manager or being a founder. Probably being a founder. They're both very hard.

• 1:29:37Speaker 00

  Yeah, it is quite hard too. Yeah, yeah. I mean, and like, just to be perfectly clear, like, there's something really special about founders, like at both Pandora and now at Zero, the actual founders have from time to time say, well, you're like a founder. And I'm like, I'm nothing like a founder. You took all the risk, you know, and like, when I showed up, like, there was a team and there was like, you know, momentum and there was money in the bank. Like, I'm, I'm, you know, I appreciate your desire to say complimentary things, but like, you're like a founder is not one that I'll, I'll, I'll take.

• 1:30:08Lenny Rachitsky?

  With that, we've reached our very exciting lightning round. Are you ready?

• 1:30:11Speaker 00

  I am ready.

• 1:30:13Lenny Rachitsky?

  What are two or three books that you've recommended most to other people?

• 1:30:17Speaker 00

  I really love Alad Gill's High Growth Handbook. It's organized into chapters about foundational company building, building a leadership team, building a board. And in addition to the thoughtful synthesis on that topic from Alad, there's also, he has an interview of someone that he does relevant to that section on each of the chapters. Really, really great read and super actionable if you're a leader in a young company. I mean, the completely different end of the spectrum. I love big, complicated science fiction. And I mean, there's like a lot of garbage science fiction out there to be sure. But when you find something special, it's like, it's the best.

• 1:30:59Speaker 00

  So probably through the years in that category, there's a book called Hyperion by Dan Simmons. That's, it's just like a total classic. Everybody should read it.

• 1:31:08Lenny Rachitsky?

  I read that. I read, I think I read the first couple and the first one.

• 1:31:11Speaker 00

  Yeah, there is a sequel that's exceptional as well. And it's probably worth warning your readers that Hyperion is quite long and has an absolute cliffhanger.

• 1:31:20Lenny Rachitsky?

  I think they're making a show out of it, which is going to be wild. I don't know how they do a show around that book. I thought you were going to say this other book, A Fire Upon the Deep. Have you heard of this book?

• 1:31:29Speaker 00

  Oh, that's so good, too.

• 1:31:31Lenny Rachitsky?

  That's also very complicated, but incredible.

• 1:31:34Speaker 00

  Yeah, I had completely forgotten about that. That's, that's a very special book. There's a couple in that series, too.

• 1:31:40Lenny Rachitsky?

  Yeah, I think I only read the first one. Also, Three Body Problems is the other one that I always think about. It's come up a couple of times on this podcast. Let's move on to the next question. Do you have a favorite recent movie or TV show?

• 1:31:52Speaker 00

  I consume a lot of video content, both like, you know, stuff that I'm very proud to talk about and stuff that I'm less proud to talk about. But I really liked the new Damon Lindelof show that's on Peacock called Mrs. Davis. So Lindelof, of course, from Lost and the new Watchmen on HBO. Mrs. Davis is about an AI that you wear in your ear, like the her AI, and a nun that is hell-bent on the AI's destruction. And it's, it reads like an early Coen Brothers movie.

• 1:32:33Speaker 00

  It's super darkly funny and really, really thoughtful and unlocks too much streaming. I think it's seven episodes and it is a perfectly encapsulated story that has a beginning, a middle and an end and doesn't need to ever have another episode. It's amazing. It's worth, it's worth the, you know, get yourself a Peacock subscription for at least a month to, to, to watch Mrs. Davis.

• 1:32:55Lenny Rachitsky?

  Favorite interview question you like to ask candidates that you're interviewing?

• 1:32:59Speaker 00

  There are two things about interviews. The first is I always encourage people when they're thinking about their interview questions to take any question that, that they're tempted to pull from their own current experience and with the goal of trying to like, how would this person solve this thing that I'm working through right now? Cause it just calls in the other person to like speculate and oftentimes like about your own business, I think you know really well that they don't actually know anything about. It's just, it creates this imbalance between the interviewer and the interviewee that feels like out of sync with how I think about the collaborative nature of a great interview. So I tell people like that almost every interview question should start with, tell me about

• 1:33:44Speaker 00

  a time in your career when, to just, to give them permission to like, or to set their expectation that I'm asking them to tell me about something they've actually done that is relevant to the topic that I'm, I'm probing. So that's a, that's a, just a structural thing that I try to do. And then I'm usually towards the end of the interview, I ask almost everybody, imagine that you had like a really great day at work. Tell me about what, like what was it that you did on that day? Cause I'm trying to figure out this kind of like left to their own devices, what do they go to naturally because it rewards them?

• 1:34:25Speaker 00

  Because I think it's really important to find the highest best use of everyone you hire. And sometimes you can get a little bit to the bottom of like, what's the highest best use? If you understand the things where there's a natural reward mechanism, because it's like, well, I had this great day, I'm gonna do more of that tomorrow. What was the thing? And it's just pretty illuminating.

• 1:34:45Lenny Rachitsky?

  Is there a favorite product you've recently discovered that you really love?

• 1:34:49Speaker 00

  I have bought every pair of headphones on the planet. In part because Apple's headphones do not stay in my ears. They just like, I've sneezed one across the room. I've lost one down a drain pipe. I, they just, they don't stay, they never, none of them. The wired ones, the not wired ones, the in-ear ones that they're just, and, and it's left me feeling, honestly, like I am some kind of anatomical freak. Like I will look at other people wearing them, I'm like, what is going on with their ear? That it's just staying there, perfect. It seems inconceivable to me. Nonetheless, I, you know, I have a pair of AirPods Pros that I want to love. And like, kind of put up with the fact that I'm gonna drop them, lose them, sneeze them across the room.

• 1:35:32Speaker 00

  But recently, I came across this product from a company called EarTune, that are these kind of, they're replacement tips. And they just have like, the littlest bit of like, compression foam on them. So they still, they don't make the AirPods so big that they won't fit in the recharging case or anything, and they work miraculously. They stay in my ear. And Apple has this feature called like, size fit or something? Go in Settings, find your, your, your AirPods, scroll all the way down in the Settings, and you can run this test where they play some audio and they tell you how good the seal is.

• 1:36:16Speaker 00

  And that revealed that my right ear is weirder than my left ear. So I actually have to use different tips in either sizes. Suddenly, this sounds like a vaguely disgusting conversation to be having. Anyway, I'm just really thrilled about my ability to wear Apple's AirPods after all these years.

• 1:36:32Lenny Rachitsky?

  I think what we're learning is you are mutant. Your ears are.

• 1:36:35Speaker 00

  Yeah.

• 1:36:36Lenny Rachitsky?

  Are different.

• 1:36:37Speaker 00

  Yeah.

• 1:36:38Lenny Rachitsky?

  Cool. We'll link to that product in the show notes.

• 1:36:40Speaker 00

  Okay.

• 1:36:41Lenny Rachitsky?

  Do you have a favorite life motto that you often come back to or share with friends, either in work or in life, that you find useful?

• 1:36:47Speaker 00

  I mean, you can't be like a product person without having an eye-rolling Charles Eames quote that's at the center of your existence. And for me, the Charles Eames quote is, "The details are not the details, they make the design." And I just, I just really absolutely believe that, that like, the devil is in the details when you're a product designer, and be uninterested in nuance at your peril.

• 1:37:13Lenny Rachitsky?

  Final question. You worked with the creator of the GIF format. How does he pronounce GIF or JIF?

• 1:37:22Speaker 00

  Yeah, so before all of this, I worked at a company called CompuServe when I was in high school.

• 1:37:29Lenny Rachitsky?

  CompuServe? I used CompuServe. I didn't know that. That's amazing.

• 1:37:33Speaker 00

  There was a guy on the team named Steve Wilhite, who invented graphics interchange format, G I F. And he was a straight-out-of-central casting, 1960s, neck-beard programmer type, and the first I had ever encountered, and very prickly. And it's crazy, but at the time, Steve would take all comers in the fight that it was pronounced JIF. Now, he's obviously wrong. It's obviously pronounced JIF. It's crazy to me now, 35 years later,

• 1:38:17Speaker 00

  this is still a topic that pops up on the internet every once in a while. It's somehow, like, zelig. I like, I cross paths with the, you know, the guy who created graphics interchange format, and I know his opinion on the topic, even though it's an unpopular one.

• 1:38:34Lenny Rachitsky?

  Got it. So he likes JIF, but you agree it's GIF?

• 1:38:37Speaker 00

  It's definitely GIF. It's obviously GIF.

• 1:38:39Lenny Rachitsky?

  Okay, great. We're on the same page. We've decided. Let it be known.

• 1:38:44Speaker 00

  Let it be known.

• 1:38:45Lenny Rachitsky?

  Tom, we've talked about successes, we've talked about failures, mental health, general health, all kinds of awesome stories. Two final questions. Where can folks find you online if they want to reach out and maybe ask some other questions that I didn't ask? And how can listeners be useful to you?

• 1:39:00Speaker 00

  I'm at T Conrad on all the socials from Twitter to threads to Instagram. My DMs are open everywhere. And I really, I would absolutely be delighted to hear from any of your listeners on any topic that they choose. And, you know, what can you do for me? Well, I would love for folks to download Zero and give it a try and send me some feedback about what we're doing right and what we're doing wrong. And we'd love to have our little product be part of your life.

• 1:39:32Lenny Rachitsky?

  Awesome. Tom, thank you so much for being here.

• 1:39:35Speaker 00

  Thank you.

• 1:39:36Lenny Rachitsky?

  Bye, everyone.

• 1:39:39Lenny Rachitsky?

  Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.