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

26 Nov 2023 · 1 h 40 min

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Lenny's Podcast

Product | Growth | Career

Episode

Billion Dollar Failures, and Billion Dollar Success | Guest: Tom Conrad

Episode Overview In this episode, Lenny interviews Tom Conrad, the CEO of Zero and a board member at Sonos. Tom shares insights from his extensive career, which includes significant roles at both successful and famously failed tech companies. The discussion delves into lessons from these experiences, advice on career choices, understanding business models, and avoiding burnout.

Key Topics Discussed

Tom Conrad's Career Highlights

  • Apple: Developed key features, including the drag-and-drop folder functionality still present in iOS.
  • Pandora: Served as CTO, contributing to its growth from zero to 80 million users.
  • Snapchat: VP of Product, working closely with Evan Spiegel.
  • Sonos: Current board member.
  • Pets.com and Quibi: Notable failures offering valuable lessons.

Lessons from Failures

  • Pets.com: The rapid rise and fall highlighted the risks of overfunding and poor timing.
  • Quibi: Despite its failure, it reignited Tom's passion for building and taught him about the importance of the foundational equation of a business.

Lessons from Successes

  • Apple: Emphasized the importance of combining engineering excellence with thoughtful product design.
  • Pandora: Demonstrated the power of meeting user needs authentically and the impact of organic growth.
  • Snapchat: Highlighted the value of taking risks and the benefits of having a strong, visionary leader.

Advice for Aspiring Professionals

  • Choosing Where to Work: Focus on both the product and the people. Trust your instincts when assessing potential teams.
  • Not Everyone Needs to Be a Founder: Success can be found by contributing to an existing team, rather than starting a new venture.

Business Insights

  • Understanding Business Math: Recognize that companies are equations that describe how investments turn into returns.
  • Focus on Unit Economics: Particularly important for consumer subscription apps to balance customer acquisition costs and lifetime value.

Avoiding Burnout

  • Find Your Ikigai: The intersection of what you love, what you're good at, what the world needs, and what you can be paid for.
  • Work-Life Balance: Encourage a culture that values the quality of work over performative office presence.

Notable Quotes

  • "The details are not the details. They make the design." - Charles Eames, highlighting the importance of design nuances.
  • "You can achieve success in collaboration with others; you don't have to be the founder."

Additional Resources

  • Books:
  • "High Growth Handbook" by Elad Gil
  • "Hyperion" by Dan Simmons
  • Shows:
  • "Mrs. Davis" on Peacock
  • "Watchmen" on HBO

Get in Touch

  • Tom Conrad:
  • [Twitter](https://twitter.com/tconrad)
  • [LinkedIn](https://www.linkedin.com/in/tomconrad/)
  • Zero: [Try the app](https://www.zerofasting.com)

Conclusion This episode provides a candid look into the highs and lows of Tom Conrad's career, offering valuable lessons on leadership, product development, and personal growth. Whether you're a budding entrepreneur or a seasoned professional, Tom's insights provide actionable advice for navigating the complex landscape of tech and innovation.

---

For more episodes and to subscribe, visit [Lenny's Newsletter](https://www.lennysnewsletter.com). ```

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Transcript

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0:00There's this place 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, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never gonna go anywhere. That would be so much better off finding a team that needs their skill set 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 the claim of your peers, you want financial reward, you want outside impact on culture, whatever the thing is against you out of bed every morning, you can achieve that in collaboration with others.

0:46You don't have to be the person that raises the seed ground. 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's 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 at a business in 19 months.

1:26Today, 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. 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. This episode is brought to you by Coda.

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4:40Tom, thank you so much for being here. Welcome to the podcast. Thank you. It's so fun to get to the part of this. 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 or talk, and the fact that it's still around, you just share that story and maybe a lesson from that experience that you've taken away. Sure. Let's see, I was 15 years old when the Macintosh came out. I remember really clearly my entire teenage years, all I wanted to do was to move from Columbus, Ohio to Cupertino and work for Apple.

5:23And my heroes were that team of people that had written their signatures on the inside of the Macintosh. If you 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 my only ambition, truly. And this was a period where 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. Anyway, I went to 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.

5:57I'm gonna say 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 a hiring 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. It's been a summer interning. And 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.

6:39I had worked on, I probably became like shipped, it was called the Quick Draw GX's earlier kind of second generation rendering system for the Mac. I've been that to use 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. So I went and found Ron Lick -D, who is the manager of the finder team and said, I graduate in 10 months, 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? You're literally going back to Michigan tomorrow.

7:11So I go back to Michigan in May, the phone rings. And Ron says, the college recruiting department just told me that I have a college hiring rep. 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'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 usable. And I remember sitting in Ron's office and saying, you know, at the grocery store, when you're carrying bags of groceries out, like the door is automatically open for you, I think the finder should do the same thing when you're dragging an icon around and you want to put it in a folder or you should be able to kind of look, hover maybe over the folder icons and drill down into the file system to get to where you're going.

8:20And then when you drop the file, like all of 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 coding that up. And I got to the point, the late one night, two in the morning, I'm at Apple, no one else was 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 up all the night. So I just wrote some code that blanked the folder, like selected, unselected, unselected, five times.

9:02And I thought, I'll get one of the really talented visual designers to do something much more interesting. Long story short, Apple finally shipped that feature like four years later, sat in the source code repository forever while we did other things. And when it shipped four years later, it blanked five times. Roll the clock forward six or seven years. MacOS 10 comes out, entirely new finder written 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 blanks five times when you have our over it. Roll the clock forward another decade, IOS comes along and they added folders and when you drag an icon around, it blanks a few times.

9:51I'm not sure 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 we'll go back later and clean up. And sometimes, I mean, it's literally been 30 years. So 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. 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 blanks three times and then just opens up for you.

10:25Here you go. Full engineers got royalties on features they built that continue to live on in a product. 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 name was, our names would scroll by, you know, the finder copyright 1992, you know, yada yada yada, one name after another, totally different era. It feels like you got kind of what you wanted with the name scribbled on the motherboard.

10:59For sure, I've gotten, I've got a lot of the things I wanted as a kid. 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? When I was a kid, my ambition to work at Apple was like 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.

11:39Pretty quickly you learn that it off a lot of your development and day -to -day satisfaction, like really comes from like 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 to give you latitude in the right ways? Like 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 and the rest will kind of take care of itself. And interestingly, like I haven't lucky enough to have some things that were successful, you know, on the metrics get talked about the most big audiences, big financial return, et cetera, et cetera.

12:22And I've also worked on some things that were like, you know, really notable disasters. My sort of, I look back on my career and like think about the things that I've done. My professional satisfaction is not well correlated with those sort of external metrics and very, very coordinated with, you know, I love the thing we were building and do I love the device we're going with. Following the threat 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 your product, you have a lot of time that you spend with the team.

12:54Most people don't. They have like 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 the people or the kind of people they want to work with? 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, you know, working with people who had a different set of, you know, values or working styles than that I had, I knew. And you know, you tell yourself that, at least in my case, I tell myself the story about why the thing is to suspect, you know, might be the case, you know, isn't the case.

13:30But, 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 with 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. And then sometimes you're like, I think I made like a, like a permanent lifelong connection with this total stranger who just happened to sit next to me. Like, you know, it's like a very simple piece of advice that I think people don't fully appreciate it is just like trust your instinct, trust your gut. Yeah. Just pay attention to what comes up when you're around people at a certain company.

14:05Okay, so you brought up this phrase of notable disasters. And I wanna 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 wanna 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 twice you share with people. Probably the biggest lesson is not really about like the specifics of the business.

14:41The biggest lesson really is these things make you better. They, in some instances, actually I think in both instances, they became kind of dominoes that opened doors for me in my own ambition and my own sort of professional life that maybe just wouldn't have opened it 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 it, I could have worked it, one of a thousand e -commerce websites in 1999. And when it went on to some subsequent job interview or something and talked about my experience, who will have like, I would never heard of the thing that you worked on.

15:21But everybody certainly heard about pets .com. It's a pretty funny example too of how some struggles are like timeless, you know, that was 20, 23, 24 years ago now. And 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, you know, national broadcast television advertising, we all did.

16:17And it became this kind of unwindable arms race. So there was like a, there was like a, 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, the, you know, Chewie is an online pet store for $9 billion today. They were a private company and bought by Ketsmart. And it's fun back out, but when they were bought by Petsmart, they were required for $3 billion, you know, biggest e -commerce acquisition of all time.

16:58And well, I think it's probably unfair to compare Chewie who executed exceptionally 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 let all the Pets .com, or at least at the time was like, this is just a stupid business. They're shipping dogs through around. You could never make that work. And like, that, that's just wrong. Like, you absolutely can make it work. Probably can't make it work when 80 % of the country on the internet is still on dial up.

17:30It was really, really early. 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. Yeah, yeah, the thing that's about right. You know, the other thing that's forgotten in the tale is that we, 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 gonna be able to get our capital into the company.

18:08And it was a company that required additional investment to get to profitability. And so it's 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, it was sort of a fruitless attempt to salvage it. 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 they took away from that experience that you bring with you? The kind of miraculous thing about Quibi for me was it re -lit my enthusiasm for the industry for doing this work.

18:51I 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. I done it for 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'd be fun to have like another chapter of my life that was just completely different. And I had a whole 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.

19:29Maybe I want to be a landscape photographer. Maybe I want to learn to make bad music to put up on SoundCloud or something. And the only thing they had in common were all things that I knew nothing about. People would be like, oh, you think you might be a pastry chef, do you like to bake? And I'd be like, no, I don't know anything about baking. You know, oh, you might have landscaped a tower of me. 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 Techbridge interviewed me about my departure from Snapchat, I was like, you know, I'm out, I'm going to do something else entirely.

19:58That story is very much out there. But a few months after my last day at Snap, I got a call from Meg Whitman and Jeffrey Katsonberg who were starting up, it was called New TV 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 why I know if I was interested in one or both. And I took the meeting, even though I wasn't only taking these kinds of calls from anybody, I just seemed like who's going to pass up the octane and have one trip with the two of them.

20:49So 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 go to lunch, they give me an update on the progress they were making and I would decline, you know, the invitation to get an awesome out. And then late in that year, I went to lunch for more time and Meg explained that they brought on someone to lead technology and they brought another person to lead product and both of them, for really truly per reasons that are completely disconnected from Klooby itself, both of them had left after about six weeks.

21:36And 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 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 to come, it's been 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 great if you could help me get this off the ground. And my wife is a freelance writer, marketing strategist and loves her life as a freelance contributor and she's like, you should do this, like why not?

22:12It's two days a week, it's just a few months. What's the worst thing that could happen? Like maybe you'll like it and I'm like, 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 and 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 if she's wrong about this.

22:45I fell deeply into it right away 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 embarrassed about some 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 build something and to try to put it out there even if you stumble pretty mightily along the way.

23:35Is there something that you took away from that experience that taught you what to try to avoid, what to try to pull towards? I think I'd sort of misunderstood or misjudged companies sometimes by thinking about them like really focused on the product execution. You know, kind of if you find an interesting problem that people, you know, people care about and you solve that problem in a really beautiful, elegant, delightful way that's 10 times better than anything else that they can get in that same space. They'll tell their friends and like all the rest of us will sort of take care of itself. And so that was always my ambition.

24:16Find a thing that I get about building, do a great job building it really delightful way, go really deep on listening to people and their feedback and iterate your way to success and for 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.

25:05But if the equation is fundamentally broken or a big swing in and of itself, no amount 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. And there'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 made in a single year. So this is a pretty major accomplishment.

26:00And we made a bet that we would augment those sort of episodic and serialized for 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. 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.

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26:43And it was really expensive. Like I said, it was like a third of the investment we're gonna make in content, maybe half, almost half the investment we're gonna make in content. And we launched two weeks in the 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 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.

27:23And maybe we were never gonna do better than that. But I think it was really fundamentally burglar with Clippy was that the actual foundational equation of can you make enough premium content that's totally bespoke and made for the service and tastes advantage of the nature of the phone. It is that enough content to get people to sign up and retain and can you do that for a couple billion dollars. 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're really, our roadmap really wanted to innovate on the content format.

28:06And so I think part of what happened is pretty quickly it became clear that the math was just wrong. It wasn't gonna take two billion, it was gonna take six or eight or 10 billion. And the risk -ruored profile of betting 10 billion on the format was just more than anyone can sign up. 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, could be because I think it was meant to be on the go. Yeah, like sitting at home where you could watch anything you want.

28:42Yeah. But also the fact that the content couldn't be made as well as you were hoping to make. Yeah, for sure. Yeah. 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 gonna work out almost a matter of what you did. One of the bets was that we weren't gonna just use the apparatus of Hollywood to like make the content.

29:21In part, we are gonna 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 a watcher or was going to make something. And like part of what they are 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 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.

30:07On 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 out 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 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 front out of their pocket and download this thing and start a free trial.

30:54Now, those of us who 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. No, just how hard that is. So maybe if I critique my own contribution to the math equation, maybe I should have beat the drum a little harder about just how unlikely it was that we were gonna land the kind of distribution in month one that the model sort of required. I had to go back and do it again. I think I would spend maybe more time investing in illuminating that aspect of the digital universe. What is such a good takeaway of just showing the leaders, here's the data, here's the assumptions they were all betting on.

31:49And do you believe this can happen? And they probably would have said, yes, this will happen, I'm so confident. 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, then you could probably make the case, it's impossible. But since you only started having 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 and when the likely thing happened that we got millions of people to download the app, which we did.

32:36And then that would be when we inevitably struggled to retain those users at high percentages and we were retained. It's sort of what I think of as like a good industry, starting point, but we weren't setting any records on retention. I just imagine that what happened 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 figure the formula out to get people in and get them to stay and get them to retain. And what I didn't appreciate was just how quickly you go back to the foundational math and then the math really says, you just can't.

33:22You can't spend two years iterating your way on optimizing the funnels like you would in a startup that had a different cost structure like in a world where you have to spend $1 billion a year making content. You just can't afford to not be a hit. I think it's also important to just remind us it's okay for these things to happen. People take a bet as you said, we're gonna try this thing. Here's our experiment. We're betting on this sort of format and this business. We're gonna raise money from investors that know they might lose all their money and it sometimes doesn't work out. It's part of the game.

33:56It's certainly painful to take money for investors. You'd say no, what they're doing and to not get them returned. I feel a real responsibility to investors to do better than we did. Equibi, but yeah, I mean, there is a risk -for -war thing that goes along with these investments and part of the reason I get all the riches on the upside is that they're gonna bet on some equibi's long way too. 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.

34:36Raising a billion dollars working with top talent are you interested in exploring this opportunity? Lenny, Lenny, Lenny, your story could have been so much different. You could, this could have been Thomas Podcasts. Lenny, don't worry about what happened at Kirby. I would take that tree. 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 gonna read through this and see what they pitched back in the day. Okay, let's move on to things that worked out really well. What's called notable successes. Other products you worked on that worked out great.

35:12So I'll list a few of them. And maybe what might be helpful is just, let's just go through each one and share what you took away from that experience, less than 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. I think if you're 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.

35:44So that's cool. I didn't know that you worked on that. And then there's also Sonia, so what you're on the board. So whatever order you think may be most interesting, just going through those and what did you learn from that experience? I worked at Apple in the interval where Steve was gone. John's Felly, that kind of period. So System Seven, System Eight, Power Macintosh, like that whole era. And we were doing a lot, we shipped a bunch of great hardware, we transitioned the company from Motorola 68000 CPUs to the PowerPC architecture, but particularly in that transition, we really struggled to ship consumer software features.

36:25I mentioned, I wrote three -learn folders and some other consumer features, like in my first six months at Apple and they shipped four years later, actually after I left the company, I was a little surprised they were still in the software repository even, can't really. But I'll tell you 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 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.

37:19And so when I left Apple after four years, I looked back on my time, I didn't ship as much software as I had hoped, and I felt like a little bit like a professional gadfly. I was like six miles wide and like a centimeter deep. And I went to the work for this company called Berkley Systems. They envisioned to do a ton of jack, they made the flying toaster screen saver, if you remember. I remember the 90s. I 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 know, I'm Jack Franchise, managed a team of engineers, and it was a completely different culture than when I was used to it, Apple.

38:11It was certainly the case that I was welcome to weigh in on the game design or the marketing or some other aspect of the deliverables, 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, what's gonna pass it 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 tops as an engineering manager, but I also wrote a ton of software.

39:01And that's really honestly when I became a software engineer. Like my college education was insufficient to get me there, 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 experienced, like feeling like I could really sold 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 so I feel really lucky that I stumbled into the United Jack one I did.

39:36And 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 versions of you down to Jack that's art in all of the stores, in the PlayStation store, in Xbox store, in the iOS store. You can play new versions of you down to Jack to the stage, crazy. Did not know that I see the website now. And it's a little different than basically the same. So I'd say my lesson for, you know, when you go to Jack was definitely like, it really does pay to get good at something and not just be a generalist.

40:24And then, I mean, you know, Pandora, it was, it was with the next thing that happened after you got to Jack with 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 gonna build a destination for music discovery on the web. And I've been doing Enterprise Software. The consumer internet was like non -existent for those years, early odds. And but around 2004, things started to thaw a little bit. And you started to hear the first signs of the companies that would come to call with Chewdoddo, like Flickr, would have been one of the early examples.

41:08And 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. Until 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 at Kidding College, who would corner you and be like, oh, if you like this band, I gotta play this for you and you know, stay with 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, introduced them to music that they would love, but otherwise would miss out on.

41:53And 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 biting my time to exit the Enterprise Software Company. I was VP of engineering. A whole team, parted to me. I got a lot of responsibility to, to, 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 and the Spring of 2004 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.

42:45And the thing that we had in common in high school was we loved music. And so I tell them the story of, like, I'm gonna start this company to do personalized usual 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, hot savage beast that like are also doing something in music recommendation. Do you want to talk to them? And I should sure why not. So I got introduced to Tim Westergrin. It was the founder of Savage Beast. Savage Beast was like a seven or eight full -time employees at that point. They made a music recommendation engine that they licensed to other companies to put in consumer products.

43:25So Savage Beast's customers were best by who put it in kiosks and AOL who used it in the AOL music website. And they were looking for a BP of engineering. And I got the offer, thought about it a little bit, I declined because it was kind of this B2B2C thing. And I really wanted to do something and get to where I'm at idea about the app. And like a month later they called it again and said, you know, he'd talk to people, you really think that you're the person. And interestingly, one of the reasons they thought that it was the person is they were really impressed by the fact that they had run engineering at PETS .com.

44:02So I mean, it's just one of those things where these things do pay dividends even when they're a disaster. And honestly, 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.

44:43And Joe is a product marketer and just the best CEO and whole, we're always spending 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 build the team and the culture in collaboration with him and Tim, the founder over the course of the next 10 years. And yeah, it's just every good thing. So I mean, it's just a million, billion lessons from Pandora. I mean, everything I am as a product leader and then engineering leader comes from things that happen at Pandora. But maybe the thing that I think of first is I think we met our early audience in like an incredibly genuine way.

45:35For example, when we launched the support at pandora .com was an alias for all at pandora .com. So if you send 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 request first should respond to it. And so 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, you'd get the CEO, and there were no macros to like responsive to commonly ask question. There was no, read the FAQ there.

46:17And there were no rules about what you could and couldn't say if the person's like, I think this feature is like stupid in broke. And 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. I would use, you know, I'm in a 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 real human beings, not like as a shiny brand that was trying to, you know, you know, be something that we could just never be.

46:51Like this is, this period is where the iPod and iTunes are like 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 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 of the product and they told their friends about it. And that's how I grew. I saw a stat that you grew Pandora from zero to 80 million users from 10 employees to 3000 employees from zero, basically it's a multi billion dollar company.

47:31So we did those things about did. We also, I mean, I think my product stewardship, like in some ways set the scene for Spotify to walk through the digital streaming door and like show us the exit. So Pandora is, you know, I mean, I again, such a privilege to be able to work on something that touched and continues to touch tens 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. My mom is still a huge fan of Pandora. It uses it every day for whatever term. I mean, it's still going.

48:11And there's like the numbers are still tens of millions of people in the US listen every month. So 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 have come along since. 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 in the math formula set up in such a way that it was nearly possible? 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.

48:46You know, it was lawsuits. It was there's no money to be made. There were relationships with the labels that were completely impossible to nurture. And there have been no big outcomes like the, I think the biggest exit in digital music when we got going was a Yahoo had bought music match for like $400 million. And so that was seen as like kind of the ceiling on the opportunity. Then you know, along the way we found investors who believed in our vision and invested, you know, ultimately hundreds and millions of dollars in the company over its pre -public years. But there was never like a investor enthusiasm for the company in the category that was anything like the investor enthusiast and that company like Spotify enjoyed just six, seven years later.

49:30Snap enjoyed for, you know, it's, 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 for, you know, 400 million. They were Pandora at eight 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, and, you know, Spotify really played that to their advantage in a way that we couldn't because we hit on public and the public market investors were still trying to, you know, figure, figure us out.

50:10So we didn't have access to capitals, very hard for us to, to, to take the same kind of risks that, that, that Spotify took. But then I think we just completely misjudge 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 like 10 times more music minutes a month on the on radio in the arts and early tens, then on own music. And the advertising supported sort of radio market was $30 billion category and recorded music with $8 billion.

50:56And 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 is Spotify before Spotify, they were all going to chase this smaller record, owned recorded music opportunity. And that, you know, we could be left and relatively alone over here, going after the less sexy, but actually bigger market. And I think we just got it wrong. 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, they were going to set the terms on what the structure was and the structure that they preferred was the Spotify structure.

52:01And 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, a little bit of exceptionally risky for us to come out from under the statutory license and do direct deals with the labels, but it was a requirement to play in the world that they imagined as the future. And we should have imagined as the future to eventually the company got around to it and and that it was just it was too late. It's interesting that so much of this was rooted in that original vision that you shared a Pandora of the radio, smart radio in your pocket.

52:35Yeah, one thing. So yeah, 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 worked at pets .com and and Pandora that is 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. You know what's really, really funny about that just today. There's a headline about a Hollywood produce show that's launching on Instagram Reels and TikTok, which shot vertical.

53:13And the headline is literally something like is TikTok of the new TV. And it's pretty funny that literally that's what Jeffery and Meg called it when they were incubating the idea. I mean, I think it's pretty clear that 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 stared at our phones consuming video of all kinds, you know, all day every day.

53:50So there's definitely something there. 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 a bit all my money on this new quibi clone because the timing is timing my pure hit. This episode is brought to you by help. Park by Camillean, 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 help are solves this. It delivers answers directly inside your app and eliminates context switching.

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55:17Let's talk about snap briefly. I want to have a couple more questions at the end or I I was a hit of products. I'm head of engineering and our CEO was brilliant, but he was a product marketer kind of. I mean, he was Joe with 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 do 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.

55:59So rewarding, so gratifying best professional experience that one could have.

56:06So I leap into our after a decade. I take like a year. And trying 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. I a mutual friend sent this introduction over at an immediately respond 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.

56:48And then they toss me into a conference room with like a dozen product designers. All their mid to late 20s, many of which are that 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 right at a conference table. And it wasn't like clear that they knew why they were talking to me. But we had kind of a, you know, hour long free -ranging conversation. And 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.

57:24I was like, well, with these interviews, like, I'll see you very ad hoc. Is there a job opening? I guess it was a little odd. And I went to lunch at an Abbott Kinney and got a text from Evan's admin saying, can you come back to the office if you got on your plane? Yeah, I was like, I was just like ordering lunch. 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 not at the clock in the morning. I sit down in the conference room. Evan comes in with a Manila envelope and says, we love you. We like free PRDPer product and like handed me a written offer.

58:04Like all the terms, like the stock conversation, the whole thing. I'm like, I'm gobsmacked. Like I'm flattered. Like this is like really playing to my ego. I like, I can't believe that this company that feels like maybe the most interesting thing that's happening in consumer tech. You know, they're notoriously brilliant and mercurial founder has like taken a shun 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 when some of that buzz wears off, I start to wonder if there's like some red flag and flagged her maybe.

58:42So I tell Evan, and I like to come back and like meet more of the leadership teams. I'm more time with you. Go a little deeper on what this means. And so we send our courtship by another week or so. And I, you know, super impressed by the rest of the leadership team and the product thinkers and. Duffer desires and things that I was going to get to work with daily basis. And so I take the job full knowing that it's like going to be wildly different than Pandora. We're at all of this latitude to like kind of do whatever I might want to do. And in the, you know, the context of Snapchat, best I was going to be Evan's kind of right hand, you know, person that principally executed his vision.

59:29And that's certainly what it was. I mean, Evan and I ended up having like a really great collaboration. But it was certainly most days I was executing on his vision, both at a high level and very much in the details. And Evan's, 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 his 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 croissants or something.

1:00:13But one, one really, really big important lesson that I learned at Snap is about risk -taking. And like when you have the financial support and the foundational relationship with your investors that Evan has, it really allowed him to take these really big swings. A choir technology that he thought was game -changing, build features speculatively that maybe would be pruned in any other product -representing process because the odds of them having an outsizing or modest. And it just allowed him time after time to like make bets to pay it off. And like we forget about the ones that don't work when there are so many home runs, you know, in those years.

1:01:01And we didn't have environmentally, you weren't set up for that at Pandora, but I think in some ways like I was at 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 things have went from, from Evan and Snap. That is an awesome story. It resonates a lot with what Brian shared about how he thinks about product now and just kind of telling people kind of what to build versus very bottom -up. And then you tell us ideas you have. That impact the way you run, we're going to talk a bit about you as CEO now, but I guess you have a place you try to be of CEO as here's what we're building.

1:01:40As a product oriented CEO, like how much you should lean into 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, 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, was so, so inspiring. But one of the side effects of that is we get in a room and we would turn over some problem or opportunity.

1:02:24And 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, that's right, that's right. And even though there's been the huge consensus of what the radio answer was, we've got to talk ourselves out of making decisions. That one wasn't Steve Jobs necessarily could be somebody else. Who wasn't there?

1:02:56So I think what broke Apple out of that mood 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 had 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 and the teams report that there's just like churn and no progress. And there's fight, domes and politics and all the rest and that as the CEO is a brilliant product or an CEO, they are uniquely situated to come in and cut through all of that garbage and, you know, get the trains running on time again.

1:03:49Having 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 in a 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 and 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. 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.

1:04:39The one way you always have a 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. I thought it's important right now, but like, what do you think? 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. There's a really good episode I had with Lane Shackleton from Coda and you share this framework called flash tags that they use at Coda and I think it comes from HubSpot.

1:05:15You tell people here's the how 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. I try to do a lot of that. I wish I could say that in my experience that that pays off. I'm going to have a lot of time, even if I say very clearly, just one person's opinion, focus on what I, you know, don't change your priorities to go work on this. Like it has morbid outsized impact on people's behavior that I know. You're said than done. Coming back to your journey, we've talked through the story up until getting to Quibi.

1:05:56But 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 a Geo leader company to being the CEO for the first time? Why do you do zero as that role? And what have you learned as CEO that you wish you knew as a product leader and a Geo leader at a company that listeners might find useful? 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 well do sort of, you know, soul searching about what I learned and what I might want to do next.

1:06:30And you know, they thought about it and I realized that I really wanted to move on to something where I can 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 it, you know, a mark on the culture that's unique to the founder. And then as we just, you know, discussed like I'm always really interested in and building things that are, you know, are near and dear to me.

1:07:12And 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 off a 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 a little bit more weight to it that I could spend my time on. And so, you know, I, my first thought was I would start something. So I work, 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 well.

1:07:47I was 50 or 60 pounds overweight. My cholesterol is in the red zone. I mean, I was like out of breath climbing stares, 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 looking into 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 a really deep on metabolic health, like just like thousands of hours of podcasts and videos and, you know, glucose monitoring patches and aura rings and digital fitness gear. And just to try to understand, you know, the things that impact health and longevity and.

1:08:32And, you know, as much as I would like to report that when I learned is that there's some like magic pill that you can take, maybe some like, also label, rapamize and or something. The truth is, is that, that to live longer in healthier life, you really have to attack what I would call metabolic disease, which will manifest in overweight, you know, obesity and prediabetes and diabetes and high cholesterol. And, you know, all of these things that impact your your larger health. And so I found zero in this path and was using it to help my own sort of health journey. And Mike Maeser founded the company four and a half years ago.

1:09:12And he and I were talking in this interval about my own experience to product. I was just kind of giving him products back 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 roll 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 I 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.

1:09:49And so we know we've got a great little company in 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. And you had double digit growth even coming out of the pandemic when lots of helping fitness companies kind of saw retreats. And most importantly, it like it actually works. So you know, 75 % of the people who use the platform lose weight. I mean, people lose on average five 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.

1:10:26We 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 we derive and deliver, you know, for every person who downloads and, you know, installs the app. How do we 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.

1:11:00And, you know, I'm looking at my whole career. I'm definitely a person who started all stinking software development. It was like mostly in work form. You know, you find, you know, really, a 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 get the idea of what they're doing. And they sort of optimize them through a really sort of quantitative sort of taking. So I'm definitely a person that sees both sides of that sort of left brain, right brain, you know, equation.

1:11:41That's important in software. But 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 in 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 with finance and then a business major that maybe that's the way that I would have conceived of companies to begin with. So maybe it's a little embarrassing.

1:12:16I had to be 53 years old before I, like the scale fell for my eyes. And I was like, oh, like companies are equations. And so, you know, when we first started talking about lifetime value and cost requisition cost and getting those two things balanced and just to start thinking about the 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 install to registered and for registered trial and these like very sort of way down at the bottom of all the funnel. And to like ask the product team, like, let's try to optimize these.

1:12:53And in the process though of trying to understand where we could take the business as we optimize those various dimensions and trying to understand to which of the dimensions had the most leverage. I started building these ever more sophisticated models that describe the whole business. I mean, I've, I mean, it started to get to where a lot of hats and definitely a hat that I'm wearing that I didn't anticipate at all. And so I am, I am the full time FPNA guy for zero. And so I, you know, I built this, this sort of spreadsheet that aggregates data from all of our business intelligence tools and raw data from our subscription transactions and looks at all of our historical results and all of our expenses and spend.

1:13:43And 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 like this guy. It's an idiot like that. This is a fundamental way to contemplate, you know, that product work. But if there's anybody out there like me who sort of think thought of it as arc 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 like what are the high leverage points to focus on.

1:14:22So 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 sign up for things that you can learn. And, and that's the big one for me in the last year. 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.

1:14:56Here's a way to. It's so funny too because it's a thing. I suddenly understand something that mystified me through my entire career, which was I 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 that 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 with just a product. You know, oriented thinker was just completely baffling to me and I like I now realize that they were they were they were killing the soil that I'm talking about they were telling me what it it is really matter what the screens are what the features are and like, you know, that means really matters but like if there's another higher order way to look at a company, which is really about the optimization of this equation.

1:15:51And 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 like thinking about them abstracted up the layer. So, you know, I will never stop dating you about software development is being in our form and I will never stop enjoying the days when I get to sort of lean in on the details, but. But it's been it's been pretty eye opening 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.

1:16:27There's a dualingo there's zero which I didn't know how much scale you guys reached my math here real quick so you have a million users 100 ,000 paying users you charge like 10 bucks a month and 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 they just did and that's crazy so congrats that's a rare successful consumer subscription app like never happens. And like I said every every time every startup is hard and I never stop being surprised at the the new hard things that pop up every day, but we're on a really great run.

1:17:02We've had a tremendous year and I'm just so so proud of the team lead assemble there they're incredible to the last part of the reason you're so successful is exactly which is said where there's a huge focus on l t v cack. 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 one thing that's really fortunate for for zero is Mike. Major who founded the company and I have both been sort of around the block long enough and enough times that 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 or the intentions of sort of throwing it to pay user acquisition and we made a conscious decision to optimize the value of the organic traffic that we were getting into drive our growth through l t v expansion right now.

1:17:56Rather than top of final expansion which was can't at least not in fashion in you know 2021 2022 turns out it's much more in fashion these days as as this companies are are called upon to be much much more capital efficiency than they were during the pandemic era and so. You know it's I guess I feel somewhat fortunate that my you know my natural inclination as an entrepreneur is more in sync with the expectations of the market and then it was for for a while. Okay so you probably have 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.

1:18:43Essentially 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 had a nod burn out do you know this this this Japanese concept called it you guy mm -hmm yeah but I'm sure it sure for folks that may not be for me so. So the idea is it's a bend 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 they could guy it's like the intersection of what you're good at what you love with the world needs and what you can be paid for if you find that it's a good idea.

1:19:29And interestingly your listeners should go and find this because they're they're interesting ways to label the other intersections the intersections that where they all four don't come together and 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 find those it's really interesting but it's not quite as if it's a good idea. It's easy to choose a job or to choose a path where you have three but not four which is a really great recipe feeling like there's something just out of your reach that's really important.

1:20:08Anyway 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 if you guys for me like when I'm good at when I love what the world needs that I can pay for like they're just they I've always overlapped 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 like I like I don't think I have any hobbies and I think about like what kinds of things do I do on the weekend for fun and it's like you know I'm like teaching myself after a fact 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 you know 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 it and so it's why I come back to it like it's easy to say I'm going to come a pastry chef but like I left 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 one thing is I I'm really not like a hashtag hustling kind of of leader I I there was a woman that I work 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 flanking the folder animation was like a 2 a .m.

1:22:00kind 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 and the apple arcade and went to a couple of meetings and had lunch and stood at the white board and pontificated about some nonsense 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 who I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm going to do the work and I'm getting it from the team in the middle of it and whatever and so it kind of looked like I spent 14 hours a day 6 or 7 days a week at Apple and it was I was really I was really I was celebrated for this was lots of nights where I like.

1:22:40We're clear through the night and my you been also coming in the next morning you look I was still here. I look at the tips and I got a lot 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 contribute more than I ever did. 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 in culture at end, or 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.

1:23:25And 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. 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? But I do try to create environments where people have like a reasonable balance between the regular life and their technology life or room for that if they choose it.

1:24:07And I do think that that helped through the years, it helped me keep at it. But I still work a lot of nights and weekends because I love it. It's my, you know, it's what I do. Here's the other thing. I get 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, 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.

1:24:49But I think if you 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 can do in a world, 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. I didn't really care about things. I went on a fancy watch or whatever a car, but I wanted to see the world. And so I thought like, I'm going to just go and I'm going to live in London for three months. Then if I'm going to stand, let's just go for a month and go live in Mexico City for three months.

1:25:21And like, I'm going to just have this like life where I'm like, hmm, soaking up experiences. And after doing that for six months, the thing that they came to realize is that that when 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, you know, seeking out some new experience, like it's really hard to form and maintain intimate, satisfying relationships. So I went back to San Francisco. I'm like, I can't be all over the world if I'm going to like be engaged with friends and like -minded people. And you know what?

1:25:57People do on Monday morning. They go to work. And so like, if you, like, if you want to be engaged with humanity, like where they are on Monday morning is, like, 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 if you've already described like, you know, I had a point at that. Well, I care about like this, this collaboration, but maybe I don't know, maybe it doesn't need to be software that I'm that I'm creating in the world and could be like gave me a chance to sort of fall back and live with that, that process again.

1:26:45And here we are, more software. Plus being on a board of a hardware company. What you, what you just shared reminds me of Mark Manson's book, The Settle Art of Not Giving a Fuck Where His, and I've read this book. I've not. Okay, it's like a sold like a Brazilian copies. And it 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. Yeah, totally. I think that's exactly right. Yeah, it sounds like that's like experience you went on.

1:27:21And 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? There's a segment in our industry that believes this like 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, is 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.

1:28:10That would be so much better off finding a team that needs their skill set and working on a problem that has, you know, that doesn't like that as they describe the mathematical formula that's going to win that has the market opportunity that's like the rate size that like, you know, has the 10x thinking that can really and, you know, a little buy a sticker because I'm, well, I am, let's see, you over the first time now, I've never been a founder. I've been lucky enough to find a bunch of young teams that could benefit from my skills and, and enthusiasm and sometimes to some success and sometimes to some embarrassment, but always really, really interesting.

1:28:52Yeah, 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, an outside impact on culture, like whatever, whatever the thing is, against you out of bed every morning, you can, you can achieve that, you know, in collaboration with, with, with others, you don't have to be the person that, that raises the seed ground. I 100 % agree with that. I'm always telling people, don't start a company.

1:29:26It'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. Yeah, it is quite hard too. Yeah, I mean, and like, just to be perfectly clear, like, there's something really special about founders. I 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, you know, I appreciate your desire to say complimentary things, but like, you're like a founder, is not one that I'll take.

1:30:08With that, we reached our very exciting lightning round. Are you ready? I am ready. What are two or three books that you've recommended most to other people? I really love Elad Gill's high growth handbook. It's organized into chapters about sort of foundational company building, building leadership team, building a board. And in addition to the thoughtful synthesis on that topic from Elad, there's also, he has a, like, an interview of someone that he does relevant to that, that section on each of the chapters. Really, really great read and super actionable if you're a leader in an, you know, a young company.

1:30:45I mean, completely different end of the spectrum. I, I would 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 some things that follow, it's like, it's the best. 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. I read that. I read, I think I read the first couple in the first one. Yeah. 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.

1:31:20I 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? Oh, that's so good too. That's also very complicated, but it's, yeah, I had completely forgotten about that. That's, that's a very special book. There's a couple of nice series too. Yeah. I think I only read the first one. Also, three -body problem 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 a TV show?

1:31:52I 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, the, her AI and a none that is hell bent on the AI's destruction. And it's, it reads like an early Cohen Brothers movie. It's super darkly funny and really, really thoughtful and, unlike too much streaming, I think it's seven episodes and it is a perfectly encapsulated story that has a beginning in the middle and an end and doesn't need to ever have another episode.

1:32:48It's amazing. It's worth, it's worth the, you know, get yourself a peacock subscription for at least a month to watch Mrs. Davis. Favorite interview question you like to ask candidates that you're interviewing? There are two things about interviews. The first is I always encourage people with a 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? Because it's just causing the other person to like speculate, oftentimes like about your own business.

1:33:23I 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 interviewer that feels like out of sync with how I think about the kind of collaborative nature of a great interview. So I tell people like that almost every interview question should start with, tell me about a time in your career when just to give them permission to set their expectation on asking them to tell me about something that's actually done that is relevant to the topic that I'm probing. So that's 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 have like a really great day at work.

1:34:11Tell me about what like what was it that you did on that day? Because when trying to figure out this kind of like left to their own devices, what do they go to naturally because it rewards them? Because the thing is really important to find the highest best use of everyone you hire. And sometimes you can get a little bit to the bottom of what's the highest best use if you understand the things where there's a natural reward mechanism because like, well, I had this great day. I'm going to do more of that tomorrow. What was the thing? It's just a pretty illuminating. Is there a favorite product you recently discovered that you really love?

1:34:49I have bought every pair of headphones on the planet in part because apples 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. They just, they don't stay. They're not none of them. The wired ones, they're not wired ones. The in -ear ones that they're just, 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 have a pair of AirPods Pros that I want to love and kind of put up with the fact that I'm going to drop them, lose them, sneeze them across the room.

1:35:32But recently, I came across this product from a company called Eertune that are these kind of their replacement tips and they just have like a littlest bit of like compression 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 the recharging case. And Apple has this feature called like size fit or something, going settings, find your, your, your AirPods, scroll the way down the settings and you can run this test where they play some audio and they tell you how good the seal is and that revealed that my right ear is weirder than my left ear.

1:36:20So I actually have to use different tips and either size. It suddenly, it sounds like a vaguely disgusting conversation to be having. Anyway, I'm just really thrilled about my ability to wear Apple's AirPods over all these years. I think over learning is your mutants. Your ears are. Yeah. Yeah. Hard to be different. Yeah. Cool. We'll link to that product in the show notes. Okay. Do you have a favorite life motto that you often come back to or share with friends either in work or in life, be fun useful? I mean, you can't be like a product person without having an Iroly Charles Eames quote that's at the center of your existence.

1:36:54And 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, the, the devil is in the details when you're a product designer and be uninterested in nuance at your peril. Final question. You worked with the creator of the GIF format. How does he pronounce GIF or GIF? Uh, yeah. So before all of this, I worked at a company called Compuserve when I was in high school. Compuserve. I used Compuserve. I didn't know that. Um, it was amazing. There was a guy on the team named Steve Wilhoid who invented graphics interchange format GIF.

1:37:42And he was a straight out of central casting 1960s neckbeard 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 GIF. Um, now he's obviously wrong. It's obviously pronounced GIF. It's crazy to me now 35 years later this is still a topic that pops up on the internet every once in a while. It's somehow like Zellig. I like I cross paths with the, you know, the guy who created graphics interchange format. And I know his opinion on topic, even though it's an unpopular one. Got it. So he likes GIF, but you agree it's GIF.

1:38:37It's definitely GIF. It's obviously. Okay, great.

1:38:45We're on the same successes. We've talked about failures, mental health, general health, all kinds of awesome stories. Two final questions working folks fighting 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? 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 an Adria listeners. Um, on, on any topic could they choose? Um, 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.

1:39:27And we'd love to have our little product be part of your life. Awesome. Tom, thank you so much for being here. Thank you. Bye everyone. 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 a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenyspodcast .com. See you in the next episode.

From the publisher

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

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Brought to you by Coda—Meet the evolution of docs | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | HelpBar by Chameleon—the free in-app universal search solution built for SaaS

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Find the transcript at: https://www.lennysnewsletter.com/p/billion-dollar-failures-and-billion

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Where to find Tom Conrad:

• X: https://twitter.com/tconrad

• LinkedIn: https://www.linkedin.com/in/tomconrad/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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Referenced:

• Ron Lichty on LinkedIn: https://www.linkedin.com/in/ronlichty/

• What happened to Pets.com?: https://fourweekmba.com/pets-com-failure/

• 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

• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/

• What sets great teams apart | Lane Shackleton (CPO of Coda): https://www.lennyspodcast.com/what-sets-great-teams-apart-lane-shackleton-cpo-of-coda/

• 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

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.



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