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

1. 0:00 – 4:40

   Tom’s background

   1. TCTom Conrad0:00

      There's this belief that everybody needs to be a founder. I think, in some ways, our industry would be much better off if there were fewer founders. There's an entire category of smart, creative, hardworking, talented, you know, borderline visionary people who can raise that two million dollar seed and go off and build some stupid company that's never gonna go anywhere. That would be so much better off finding a, a team that needs their skillset and that, and working on a problem that has a mathematical formula that's going to win on any metric, whatever me- metric you care about. You want, like, the acclaim of your peers, you want financial reward, you want outsized impact on culture, like, whatever, whatever the thing is that gets you out of bed every morning, you can, you can achieve that in collaboration with others. You don't have to be the person that raises the seed round.

   2. LRLenny Rachitsky0:49

      (instrumental music) Today, my guest is Tom Conrad. Tom was an engineer at Apple, CTO of Pandora, which he helped take from zero to 80 million users. He's also VP of product at Snap, where he was the right-hand man to Evan Spiegel for two years. He's been on the board of Sonos for over seven years. He's also part of two infamous product failures, Quibi, where he was chief product officer, which raised over two billion dollars and died less than a year after launch. He was also a senior engineering leader at pets.com, which famously went from nothing to a public company to completely out of business in 19 months. Today, Tom is the CEO of Zero Longevity Science, which is on a mission to extend the lifespan and the healthspan 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. You've heard me talk about how Coda is the doc that brings it all together, and how it can help your team run smoother and be more efficient. I know this firsthand, because Coda does that for me. I use Coda every day to wrangle my newsletter content calendar, my interview notes for podcasts, and to coordinate my sponsors. More recently, I actually wrote a whole post on how Coda's product team operates, and within that post, they shared a dozen templates that they use internally to run their product team, including managing the roadmap, their OKR process, getting internal feedback, and essentially, their whole product development process is done within Coda. If your team's work is spread out across different documents and spreadsheets and a stack of workflow tools, that's why you need Coda. Coda puts data in one centralized location, regardless of format, eliminating roadblocks that can slow your team down. Coda allows your team to operate on the same information and collaborate in one place. Take advantage of this special limited time offer just for startups. Sign up today at coda.io/lenny and get $1,000 startup credit on your first statement. That's C-O-D-A dot I-O slash Lenny to sign up, and get a startup credit of $1,000. Coda.io/lenny. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers, and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and roadmapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds, and it's all built on Jira, where your engineering teams are already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback, and insights in Jira Product Discovery for free, no catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny.

2. 4:40 – 7:41

   Landing a gig at Apple

   1. LRLenny Rachitsky4:40

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

   2. TCTom Conrad4:44

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

   3. LRLenny Rachitsky4:46

      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 I saw you Tweet about or talk about at a talk, and the fact that it's still around. Can you share that story, and maybe a lesson from that experience that you've taken away?

   4. TCTom Conrad5:05

      Sure. So let's see, I was 15 years old when the Macintosh came out. I remember really clearly my entire, you know, teenage years, like all I wanted to do was to move from Columbus, Ohio, to Cupertino and work for Apple, and my, you know, my, my heroes were that team of people that were, had like, you know, written their signatures on the inside of the Macintosh. If you cracked open the ear- the first Macintosh case, you would find the signatures of the 20 people or so who worked on the Mac, and that was like, that was my only ambition, truly. And I mean, this was a period where, like, no one wanted to work for Apple. I mean, that wasn't a thing, and uh, it seems like maybe a little obvious today, but it wasn't an obvious ambition at all back then. So anyway, I went to college, that was all I wanted to do, studied computer engineering at University of Michigan, and as we talk about my career, it's just over and over and over I'm gonna say, you know, an incredibly lucky thing happened. And well, 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 app, manager at Apple and I wrote an actual letter and put it in an actual envelope and put it in the mail. And got an internship and drove out in my dad's Pontiac from the Midwest to California. Spent a summer interning. And my, my last day of the internship, I was thinking about really what I wanted to do when I came back, hopefully came back to Apple after I graduated. I had worked on a product that became, like shipped, it was called the QuickDraw GX, it was an early kind of second generation rendering system for the Mac, and I'd been that team's intern for the summer. But what I really wanted to do was I wanted to work on the Finder. Like, th- this is the only thing in the whole world I really wanted to do. And so I went and found Ron Lichti, who was the manager of the Finder team, and said, "I, you know, I graduate in 10 months. I'd, I'd love to be a part of your team." And I think he was kind of like, "Well, why are you coming and talking to me now? You're literally going back to Michigan tomorrow." So I go back to Michigan. In May, the phone rings, and Ron says, "The college recruiting department just told me that I have a, like a college hiring rep. And if I don't use it by tomorrow, I lose it." So he's like, "I can't even interview you, you can't meet the team, but, you know, you're basically a freebie for me, so do you want this job?" So just insanely lucky moment, got this job.

3. 7:41 – 11:04

   Pioneering the blinking folder design on iOS

   1. TCTom Conrad7:41

      So yeah, I get to Apple in the summer of 1992, and I have a laundry list of things that I (laughs) would like to do to make the Finder more, you know, usable. And I remember sitting in Ron's office and saying, "You know, you know at the grocery store when like you're carrying bags of groceries out, like the doors, like, automatically open for you? I think, like, the Finder should do the same thing when you're dragging an icon around and you wanna, like, put it in a folder, you should be able to kind of look, you know, hover maybe over the folder icons and drill down into, uh, the, the file system to get to where you're going. And then when you drop the, the file, like all of the, the folders that opened up between you and your source and your destination would close for you." Ron thought that was a fine idea, and so th- that was the way Apple worked in those days. I just went off and started, you know, coding that up. And, uh, I got to the point late one night, 2:00 in the morning, I'm at Apple, no one else is there, where I needed some kind of animation to indicate that the folder was about to open. And I'm certainly not an animator and I certainly wasn't going to do anything thoughtful in the middle of the night, so I just wrote some code that blinked the folder, like selected, unselected, selected, unselected five times. And, um, thought, "Oh, I'll get, you know, 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. Um, it sat in the source code repository forever while we did other things. And when it shipped four years later, it blinked five times. Roll the clock forward six or seven years, Mac OS X comes out, entirely new Finder written from, rewritten from scratch. No spring-loaded folders anywhere to be seen. People complained about it. It got reimplemented. So all of the code, brand new, folder blinks five times when you hover over it. Roll the clock forward another decade, iOS comes along, and you, they added folders, and when you drag an icon around, it blinks a few times. I'm not sure what the point of this story is, other than maybe it's something about, I think we all do this as, 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, 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.

   2. LRLenny Rachitsky10:16

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

   3. TCTom Conrad10:25

      There you go.

   4. LRLenny Rachitsky10:26

      If only engineers got royalties on features they build that continue to live on in a product.

   5. TCTom Conrad10:30

      Okay. I'll tell you, like, just one other little thing to, like-

   6. LRLenny Rachitsky10:32

      Yeah.

   7. TCTom Conrad10:32

      ... 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-

   8. LRLenny Rachitsky10:46

      Wow.

   9. TCTom Conrad10:46

      ... like, our name would, our names would scroll by, you know, the Finder, copyright 1992, you know, yada, yada, yada. One name after another. Totally different era.

   10. LRLenny Rachitsky10:55

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

   11. TCTom Conrad10:59

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

4. 11:04 – 12:43

   Advice on choosing where to work

   1. TCTom Conrad11:04

   2. LRLenny Rachitsky11:05

      So kind of along those same lines, I wanna 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 gonna talk about. What advice would you give people for helping them pick where to go work based on your experience?

   3. TCTom Conrad11:25

      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." Pretty quickly you learn that an awful 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? Do they 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 have been lucky enough to have some things that were, were successful, you know, on the metrics that get talked about the most, big audiences, big financial return, et cetera, et cetera. And I've also worked on some things that were, like, you know, really notable disasters. My sort of, when 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, th- did I love the thing we were building and did I love the people I was working with.

5. 12:43 – 14:05

   The importance of trusting your gut when it comes to people

   1. LRLenny Rachitsky12:43

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

   2. TCTom Conrad13:03

      I think people are really, really good at this.

   3. LRLenny Rachitsky13:06

      Mm-hmm.

   4. TCTom Conrad13:06

      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 s- working styles than, than, than I had, I knew. You know? And y- you know, you, you tell yourself that y- at least in my case, I tell myself the story about why the thing I suspect, you know, might be the case, you know, isn't the case, but, you know. I mean, you do this in your personal life all the time, right? You meet people out at dinner, so you get s- you know, seated next to them at some industry event or something, and sometimes you come home and say to your partner, "Oh my gosh, the person next to me was just the worst." And then sometimes you're like, "I, 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?

   5. LRLenny Rachitsky13:55

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

   6. TCTom Conrad14:01

      Yeah.

   7. LRLenny Rachitsky14:01

      Just pay attention to what comes up when you're around people at a certain company.

6. 14:05 – 17:32

   Lessons from failed ventures

   1. LRLenny Rachitsky14:05

      Okay, 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 m- maybe the way to set it up is just what's a lesson you took away from each of these two experiences that you've taken with you to future work, and maybe advice you share with people?

   2. TCTom Conrad14:37

      Well, probably the biggest lesson, it's not really about, like, the, the, the specifics of the business. The biggest lesson really is these things make you better. They, in some instances, actually I think in both instances, they became kind of dominoes that, that opened doors f- for me in my own ambition and my own sort of, you know, professional life that maybe just wouldn't have opened at all if it, if I hadn't gone to those companies and learned those things and had those experiences. And, and frankly even in the case of Pets.com, like, even the high profile nature of it. I could have worked at, I could have worked at, uh, you know, one of a thousand e-commerce websites in 1999, and when I went on to some subsequent job interview or something and talked about my experience, people were like, "Oh, never heard of the thing that you worked on." But everybody certainly heard about Pets.com. It's a pretty funny example too of how some struggles are, like, timeless, you know, it's, it's, uh, you know, that was 2023, 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 over-funded pet e-commerce sites, and we all raised in excess of $50 million, um, which was, 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, and it became this kind of unwinnable arms race. So there was, like, a, there is, like, a, I think a fundamental lesson about the, like, the, you know, having an excess of, of investment can be its own albatross or, or, or, uh, lead you to take, make decisions that maybe would be o- unwise. And then of course it's just, like, you know, timing is really important. You know, the, you know, Chewy is a online pet store, it's worth $9 billion today. They were a private company and bought by PetSmart and then spun back out. But when they were bought by PetSmart, they were acquired for $3 billion, you know, uh, biggest e-commerce acquisition of all time. And while I think it's probably unfair to compare Chewy, who, 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, uh, you know, in a very, very different moment in time and, and, and tried to go to market in a really different way. The critique that is often leveled at Pets.com, or at least at the time, was like, "This is just a stupid business. They're shipping dog food around. You could never make that work." And, like, that, that's just wrong. Like, you absolutely can make it work. Probably can't make it work when 80% of the country on the internet is still on dial-up. You know, it's really, really early.

7. 17:32 – 18:30

   Why and how Pets.com shut down

   1. TCTom Conrad17:32

      (laughs)

   2. LRLenny Rachitsky17:32

      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. (laughs)

   3. TCTom Conrad17:40

      Yeah. Yeah, I think that's about right. You know, the, the, 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, the remaining balance to the investors, which no public company had ever done before. And the leadership team just, like, reached the conclusion that, that given the way market conditions had evolved, there was just no way we were gonna be able to get more capital into the company, and, and it was a company that required, you know, additional investment to get to profitability. And, and so it was better, uh-... to sort of wind down early, take the money that we, you know, we had in the bank and get it back to investors than to just spend every last penny on like a, you know, what was sort of a fruitless attempt to, to salvage it.

   4. LRLenny Rachitsky18:28

      Hm, did not know that.

8. 18:30 – 28:48

   How Tom’s experience at Quibi renewed his passion for building

   1. LRLenny Rachitsky18:30

      Let's talk about Quibi. What went wrong there? Do you think there was a path to Quibi having worked out? Any big lessons that you took away from that experience that you bring with you?

   2. TCTom Conrad18:40

      The kind of miraculous thing about Quibi for me was it relit my enthusiasm for the industry for doing this work. I had left in, I think it was December of 2018, and I thought that maybe I was just done making software. I had done it for a really long time, I'd 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. And it also seemed like maybe it would be fun to have like another chapter of my life that was just completely different. And I had a whole list of things that I thought I might want to do. I mean, they were really, they were kind of ridiculous. Like maybe I want to be a pastry chef, maybe I want to be a landscape photographer, maybe I want to, you know, learn to make bad music to put up on SoundCloud or something. And the only, the only thing they had in common were they were all things that I knew nothing about. People would be like, "Oh, you think you might want to be a pastry chef. Do you like to bake?" And I'd be like, "No, I don't know anything about baking." You know, "Oh, you think you might... Landscape photography, do you take photos?" "No, I don't make photos." But I was kind of committed to the bit, actually to the point where when, when TechCrunch interviewed me about my departure from Snapchat, I was like, "You know, I'm out. I'm gonna do something else entirely." So that story is very much out there. But a few months, uh, after my last day at Snap, I got a call from Meg Whitman and Jeffrey Katzenberg who were starting up, it was called NewTE at the time, and you know, the pitch was we're gonna try to take the best of, uh, 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 bespoken, purpose-made for consumption on the phone. They were looking for both technology leadership and product leadership and wanted to know if I was interested in one or both. And I took the meeting even though I wasn't really taking these kinds of calls from anybody, it just seemed like who's gonna pass up the opportunity to have lunch with the two of them. So I listened to the pitch and, and politely declined and told them that I was gonna be like a pastry chef or something. And we kept doing that every couple of months for like seven months. We'd go to lunch, they would give me an update on the progress they were making, and I would decline, you know, the invitation to get involved somehow. And then late in that year, I, uh, went to lunch one 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 for reasons that are completely disconnected from, from Quibi itself, both of them had left after about six weeks. And Meg's like, "We've raised all this money and we've told the world that we're shipping this product in about a year. We got an awful lot to do and I really could use some help, and I would like consider it a personal favor if you were to come and spend just a couple days a week helping." You know, she's like, "I'll continue to look for someone who actually wants the job, but it would really be, it'd be, you know, great if you could help me get this off the ground." And, um, 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? It's two days a week, it's just a few months. What's the worst thing that could happen? Like maybe, maybe you'll like it." And, and I'm like, "No, no, the wor- here's the thing that will happen. Like, I won't do it two days a week. It will like immediately be three days, then four days, then five days, then six days. Like, I just know myself." And she's like, "No." She's like, "You know, just on Wednesday night at6:00 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, but she's wrong about this. I fell, you know, 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, I'm, you know, I'm, I'm embarrassed about, about some of, of what happened with Quibi for sure, but I'm super grateful for the experience because I just really fell in love with the industry again and was reminded of just how rewarding it can be to, to build something and, and to try to put it out there even if, even if you, you stumble pretty mightily along the way.

   3. LRLenny Rachitsky23:35

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

   4. TCTom Conrad23:43

      I think I sort of m- m- misunderstood or misjudged companies sometimes by thinking about them like really focused on the, on the, the product execution. You know, kind of if you find an interesting problem that people, you know, people care about and you, you solve that problem in a really beautiful, elegant, delightful way that's 10 times better than, than anything else that they can get in that same space, they'll tell their friends and like all the rest will sort of take care of itself. And so that was always my ambition. Find a thing that I cared about building, do a great job building it in a 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, 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, the product that you build and all of the little details and decisions that you make about making that product great. But if the equation is fundamentally broken or a big swing in and of itself, no amount of like iteration and execution can like kind of g- get you out of the, the failed outputs of the broken equation. And I think, you know, Quibi made a bet that you could build an entirely bespoke content library that was sufficiently scaled to get people to subscribe and retain for a couple billion dollars. I mean, it was 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 it was a pretty major accomplishment. And we made a bet that we would augment those sort of episodic and serialized or Hollywood style shows with a bunch of daily content that we produce at the level of like network television, nightly news and so forth, that would be an alternative to some of the sort of daily content that you might otherwise get on YouTube. And that was gonna be about a third of the content spend. One like super interesting thing that no one talks about is that all of that content was designed to be made like day of or day before it aired. So there was no back catalog of it, and it was all designed to be shot in these professional studios that we built out. And it was really expensive. Like I said, it was like a third of the, of the investment we were gonna make in content, maybe half, almost half the investment we were gonna make in content. And we launched two weeks into COVID and we couldn't make any of that content except literally in the garages of the hosts' 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, of the support infrastructure of Hollywood. Now, you can argue, I mean, I think the content on YouTube is really, really exceptional in this category, and maybe we were never gonna do better than that. But I think what was really fundamentally broken with Quibi was that the actual foundational equation of can you make enough premium content that's totally bespoke and made for the service and takes advantage of the unique nature of the phone, and 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, 'cause we were really, our roadmap really wanted to innovate on the content format. And so I think part of what happened is pretty quickly it became clear that the math was just wrong. It wasn't gonna take 2 billion, it was gonna take 6 or 8 or 10 billion. And the risk/reward profile of betting 10 billion on the format was just more than, than anyone could stomach.

   5. LRLenny Rachitsky28:27

      Wow. I really like this metaphor and this mental model of the math formula of the entire business and thinking of it that way. I knew COVID changed the way people consumed content and that hurt Quibi 'cause I think it was meant to be on the go.

   6. TCTom Conrad28:39

      Yeah. (laughs)

   7. LRLenny Rachitsky28:40

      Not like sitting at home where you could watch anything you want.

   8. TCTom Conrad28:42

      Yeah.

   9. LRLenny Rachitsky28:42

      But also the fact that the content couldn't be made as well as you were hoping to make.

   10. TCTom Conrad28:46

       Yeah, for sure.

9. 28:48 – 31:42

   Takeaways from Quibi and why it ultimately failed

   1. TCTom Conrad28:48

      Yeah.

   2. LRLenny Rachitsky28:48

      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, or is the math formula set up for failure from the beginning and it's probably just not gonna work out almost no matter what you did?

   3. TCTom Conrad29:10

      One of the bets was that we weren't gonna just use the apparatus of Hollywood to like make the content. In part, we were 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 launch or was going to make something. And like part of what they were going to do is like turn up in culture and talk about their shows. I mean, we've talked, you'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 on like opening weekend for Quibi. And that was always like a very, very audacious take, I thought. Like, you know, Uber has all the money in the world to experiment with paid user acquisition and they're not consistently a top 10 most downloaded app in the App Store.But the theory of Quibi, like the math of Quibi, like did require us to, like, from day one, land in the top 10 and stay there forever. Like the, the model would have worked if we could do that.

   4. LRLenny Rachitsky30:37

      Hmm.

   5. TCTom Conrad30:38

      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 phone out of their pocket and download this thing and start a free trial. Now, those of us who have spent our life in Silicon Valley making software and, you know, really, really tried to get people to show up and, you know, download new IP in large numbers know just how hard that is. So maybe if I critique my own contribution to the math equation, 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, I, I... I've had it... If I had to go back and do it again, I think I would spend maybe more time investing in, in, in illuminating that aspect of the, the digital universe.

10. 31:42 – 35:04

    Failing is okay

    1. LRLenny Rachitsky31:42

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

    2. TCTom Conrad31:55

       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 sort of had to land in the top 10, like you couldn't quite say it was impossible. You could just say it was highly improbable. And maybe one of my mistakes was I guess I imagined that we would launch and when the likely thing happened that we, you know, got millions of people to download the app, which we did, and then th- when we, when we inevitably struggled to, you know, retain those users in... At, you know, at that high percentages... I mean, we retained at sort of what I think of as, like, a good industry starting point, but, but we weren't setting any records on retention. I just imagined that what would happen next is like the thing that happens in all young companies: You would iterate. You would, like, grind on the funnel until a year later, two years later, six months later, whatever it is, you, you figure the formula out to get people in and get them to stay and get them to retain. And what I didn't appreciate was, like, just how quickly you go back to the foundational math and then the math really says, like, "You just can't." You can't spend two years iterating your way on, you know, optimizing the funnels like you would in, in a startup that had a different cost structure. Like in a world where you have to spend, you know, a billion dollars a year making content, you just can't afford to not be a hit.

    3. LRLenny Rachitsky33:40

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

    4. TCTom Conrad33:56

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

    5. LRLenny Rachitsky34:18

       So as you were talking, you said that it was called NewTV 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, uh, executive opportunity, the CPO at NewTV, new venture in Los Angeles, with Jeffrey Katzenberg and Meg Whitman. Raising a billion dollars working with top talent. Are you interested in exploring this opportunity?"

    6. TCTom Conrad34:41

       Lenny, Lenny, Lenny. Your st- your story could have been so much different.

    7. LRLenny Rachitsky34:46

       You could. This could have been Tom's podcast.

    8. TCTom Conrad34:47

       (laughs)

    9. LRLenny Rachitsky34:47

       "Lenny, tell me about what happened at Quibi."

    10. TCTom Conrad34:50

        I would take, I would take that trade.

    11. LRLenny Rachitsky34:52

        (laughs) I don't know. There's pros and cons. I... They even sent this whole PDF. "A TV in your pocket." NewTV.

    12. TCTom Conrad34:59

        Yeah.

    13. LRLenny Rachitsky35:00

        Amazing. All right. I'm gonna read through this and see, see what they pitched back in the

11. 35:04 – 39:11

    Tom’s career at Apple

    1. LRLenny Rachitsky35:04

       day. Okay, let's move on to things that worked out really well, what's called notable successes, other products you worked on that, uh, that worked out great. So I'll list a few of them, and maybe what might be helpful is just we'll just go through each one and share what you took away from that experience, lesson you learned from working on those products. And the ones that come to mind for me are Snap, Pandora, Apple, if we want to go there. Also, you built... I don't know exactly what you did there, but you worked on You Don't Know Jack, this game that I loved. It's... 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. So that's cool. I didn't know that you worked on that. And then there's also Sonos, which you're on the board. So whatever order you think might be most interesting, just going through those and what did you learn from that experience?

    2. TCTom Conrad35:56

       I worked at Apple in the interval where Steve was gone. John Sculley, that kind of period. So System 7, System 8, Power Macintosh, like that, that whole era. And we were doing a lot. We, you know, we shipped a bunch of great hardware. We transitioned the company from Motorola 68000 CPUs to the PowerPC architecture. But particularly in that transition, we really struggled to ship consumer software features. I mentioned that, you know, I wrote...... 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, candidly. But, um, 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, you know, a talented software engineer but also a thoughtful product designer and maybe also had interesting input on product marketing, that you could build a really great reputation inside the company by playing all of those positions a little bit day-to-day. And so when I left Apple after four years, I looked back on my time, I didn't ship a lot, as much software as I had hoped, and I felt like a little bit like a professional gadfly. I was like, you know, six miles wide and like a centimeter deep. And, um, I went to work for this company called Berkeley Systems. They, in addition to You Don't Know Jack, they made the flying toaster screensaver, if you remember-

    3. LRLenny Rachitsky37:46

       Oh my god.

    4. TCTom Conrad37:47

       ... if you remember the '90s. Um-

    5. LRLenny Rachitsky37:48

       How could you forget that?

    6. TCTom Conrad37:50

       And when I met them, they were kicking off this game development for this, um, this trivia game and were looking for someone to lead the technical team. And so I joined as technical director for the You Don't Know Jack franchise, managed a team of engineers, and it was a completely different culture than what I was used to at Apple. It was certainly the case that I was welcome to weigh in on the game design or the, you know, the, the marketing or some other aspect of the, 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 was gonna benefit me in my career at all. And it was such a blessing to be forced to go deep on something, because I, you know, I spent a lot of time developing chops as an engineering manager, but I also wrote a ton of software. And that's really honestly when I became a software engineer. Like my college education was insufficient to get me there, and the amount of software I wrote at Apple was insufficient to get me there,

12. 39:11 – 40:24

    Lessons from You Don’t Know Jack

    1. TCTom Conrad39:11

       but I came out of my Berkeley Systems You Don't Know Jack experience like feeling like I could really hold my own technically in a way that just wouldn't have happened. And so I do think that there's something to be said for a culture where there are swim lanes and people are encouraged to be like really, really exceptional in their lane, and, uh, so I, I feel really lucky that I stumbled into You Don't Know Jack when I did. And it was also, I mean, it was the first thing that I worked on that had just like, like huge cultural, you know, awareness for a couple of years. I mean, it's crazy. They're still making sequels. It has been nearly 30 years and there are, there are versions of You Don't Know Jack that's, are in, you know, all of the stores. In the PlayStation store, in the, uh, Xbox store, in the iOS store. You know, you can play new versions of You Don't Know Jack to this day. It's crazy.

    2. LRLenny Rachitsky40:06

       Did not know that. I see the website now and, uh-

    3. TCTom Conrad40:09

       Yeah.

    4. LRLenny Rachitsky40:10

       ... it's a little different but basically the same.

    5. TCTom Conrad40:13

       Um, so I'd say my lesson from, you know, my, my, my lesson from, from You Don't Know Jack was definitely like it really does pay to get good at something and not just be a generalist.

13. 40:24 – 48:24

    Lessons from building Pandora

    1. TCTom Conrad40:24

       And then, I mean, you know, Pandora, it, it, it was, was quite the next thing that happened after You Don't Know 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'd been doing enterprise software. The consumer internet was like nonexistent for those years, early aughts. And, but around 2004 things started to thaw a little bit and you started to hear the first signs of the companies that we came to call web 2.0, like Flickr would have been one of the, the early examples. And, um, one of the enterprise software things I did was a, a personalization recommendation engine that used a vector space. It's like a lot of the things that we're talking about now in AI, you know, albeit 20 years ago. And so I knew something about recommendation systems in the enterprise space and I was super passionate about music. I'm not a musician, but I was that kid in college who would corner you and be like, "Oh, if you like this band, I've got to play this for you," and, you know, stick you with brainwave 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. Um, introduce them to music that they would love but otherwise would miss out on. And I promised that I was gonna tell stories about luck in my career. There's been a gazillion of them, but one really dramatic instance of that is I, I was sort of biding my time to exit this enterprise software company. I was VP of engineering. I had a whole team that reported to me. I felt a lot of responsibility 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 it to kind of get back to the team. So I, I flew down to Los Angeles to go out to Coachella in 2000, in the spring of 2004-... and completely randomly, like physically bumped into a guy that I had gone to high school with on the polo field. And hadn't seen him in a decade, and the thing that we had in common in high school was we loved music. And so I t- tell him the story of like, "I'm gonna start this company to do personalized digital music on the internet." And he said, "There's this woman I work with who just left our company to move to Oakland to work for this little company called Savage Beast that like are also doing something in music recommendation. Do you want to talk to them?" And I said, "Sure, why not?" So I got introduced to Tim Westergren, who was the founder of Savage Beast. Savage Beast was like a seven or eight full-time employees at that point. They made a, a music recommendation engine that they licensed to other companies to put in consumer products. So Savage Beast's customers were Best Buy, who put it in kiosks, and AOL, who used it in the AOL Music, uh, website. And they were looking for a VP of engineering and I got the offer, thought about it a little bit. I declined because it was kind of this B2B2C thing and I really wanted to do something in consumer. I had an idea about the, the app. And like a month later they called again and said, "You know, we keep talking to people and we really think that you're the person." And interestingly, one of the reasons they thought that I was the person is they were really impressed by the fact that I had run engineering at pets.com. (laughs) So I mean, it's just one of those things where, like, these things do pay dividends even when they're a disaster. And honestly, in like a, in like a, what I would really say was like almost like a lapse in judgment, I, I said yes, even though it wasn't, it wasn't the product that I wanted to build. And I won't bore you with all of the details, but like 90 days later, after some, like, you know, typical early stage founder drama stuff, the founding head of technology and product had resigned, completely unrelated to my arrival, and the company had a new CEO, Joe Kennedy. And Joe had this idea for what he called a one click personal radio. And Joe is a product marketer and just the best CEO in the whole world. We spent 10 years together building Pandora. And he sort of gave me the keys and just said, like, "As long as it fits the brief, one click personal radio, like, it's all yours." And I got to, you know, I got to build the team and the culture, you know, in collaboration with him and Tim, the founder, over the course of the, the, the next 10 years. And, and yeah, it's just every, every, every good thing. So I mean, there's just a million, billion lessons from Pandora. I mean, everything I am as a product leader and an engineering leader comes from, from things that happened at Pandora. Um, but maybe the thing then that I think of first is, I think we met our early audience in like an incredibly genuine way. For example, when we launched, the support at pandora.com was an alias for all at pandora.com. So if you sent-

    2. LRLenny Rachitsky45:42

       (laughs)

    3. TCTom Conrad45:42

       ... a customer service request to Pandora, every single person in the company received it. And because we had no... We made a decision to have no customer support team in the first year, the expectation was that whoever sees the, the request first should respond to it. And so, you know, you would write to us and you would get the founder or you'd get me or you'd get the engineer who wrote the feature, you'd get the CEO, and there were no, there were no macros to, like, respond to, to, to a commonly asked question. There was, there was no read the FAQ. There were... And there were no rules about what you could and couldn't say. If the person's like, "I think this feature is, like, stupid and broken," we would encourage people to say, like, "You know what? I think you're right and I'm, like, really struggling to get our stupid head of product to agree with me. Would you... You know, I'm gonna CC Tom and maybe we can convince him that, you know, this was a bad decision." And we did all of that because we thought one of our, like, superpowers as a young company was that we could just, like, engage with our audience, like, as real human beings, not like as a shiny brand that was trying to, you know, you know, be something that we could just never be. Like, this is... Th- th- this, this period is where the iPod and iTunes are, like, at the peak of their powers. And so, you know, there was no way we could sort of out Apple Apple on the brand front. And so we were just ourselves and I think it, it really, really was a catalyst for the, the word of mouth that developed around Pandora. And, like, we never spent any money on paid user acquisition. Like, literally no dollars in the entire time I was there, because people loved the product and they told their friends about it and that's how it grew.

    4. LRLenny Rachitsky47:21

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

    5. TCTom Conrad47:31

       We did those things.

    6. LRLenny Rachitsky47:32

       ... not bad.

    7. TCTom Conrad47:33

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

    8. LRLenny Rachitsky48:06

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

    9. TCTom Conrad48:09

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

14. 48:24 – 55:17

    Looking back at Pandora and what could have been done differently

    1. TCTom Conrad48:24

       since have.

    2. LRLenny Rachitsky48:25

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

    3. TCTom Conrad48:37

       One of the things that was tough for Pandora was that when we started it, digital music was like a, like a c- a category that no investor wanted to touch. You know, it was lawsuits, it was, there was no money to be made, there were relationships with the labels that were completely impossible to nurture, and there had been no big outcomes. Like the, I think the biggest exit in digital music when we got going was I think Yahoo had bought Musicmatch for like 400 million dollars. And so that was seen as like kind of the ceiling on the opportunity. And you know, along the way, we found investors who, who believed in our vision and invested, you know, ultimately hundreds of millions of dollars in the company over its pre-public years. But there was never like a investor enthusiasm for the company and the category that was anything like the investor enthusiasm that a company like Spotify enjoyed just six, seven years later, Snap enjoyed for, you know, its, you know, pre-public tenure. And you know, the, I think part of it was different in, for Spotify is that the comps were not... Musicmatch at four, 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, you know, Spotify really played that to their advantage in a way that, that we couldn't because we had gone public and the public market investors were still trying to, you know, figure, figure us out. So we didn't have access to capital. It was very hard for us to, to, to, to take the same kind of risks that, that, that Spotify took. But then I think we just completely misjudged one really important thing, which is that we were really inspired by disrupting terrestrial radio. Terrestrial radio is like the predominant form of music consumption in the country, you know, people spend, I can't remember the exact stats, but it's like, you know, by minutes consumed it's something like 10 times more music minutes a month on the, on radio in the aughts and, um, early 10s, uh, than on owned music. And the advertising supported sort of radio market was $30 billion category and recorded music was eight billion dollars. And so we had this idea that we're going to reinvent radio and Spotify and Rdio and Apple Music and like the 14 other, um, Rhapsody, which was Spotify, before Spotify, they were all gonna chase this smaller reco- owned recorded music opportunity and that, you know, we could be left in, 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 gonna be delivered, you know, as a stream from the cloud and that the record labels in particular are going to, they were going to set the terms on what the structure was and the structure that they preferred was the Spotify structure. And we operated under a different licensing regime that they hated that was a statutory license that we got from the government and it was exceptional, would have been 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 too. And, and eventually the company got around to it and, and, and, but it was just, it was too late.

    4. LRLenny Rachitsky52:28

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

    5. TCTom Conrad52:35

       Yeah, one click for, uh, radio-

    6. LRLenny Rachitsky52:37

       ... like you stayed so close-

    7. TCTom Conrad52:37

       Yeah.

    8. LRLenny Rachitsky52:37

       ... one click 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 y- seven years later. And I feel like there's this interesting trend with the companies you've worked at, pets.com and, and, uh, Pandora that it's 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-

    9. TCTom Conrad52:59

       You know what's really, really funny about that?

    10. LRLenny Rachitsky53:02

        ... or whatever.

    11. TCTom Conrad53:02

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

    12. LRLenny Rachitsky53:53

        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 were pitching. That's amazing. All right. I think what I've learned, I need to bet all my money on this new Quibi clone 'cause-

    13. TCTom Conrad54:04

        (laughs)

    14. LRLenny Rachitsky54:04

        ... timing is, timing might be right. This episode is brought to you by HelpBar by Chameleon, the free in-app universal search solution built for SaaS. Your help content lives outside your app and is scattered in many places, forcing users to waste time hunting for answers. HelpBar solves this. It delivers answers directly inside your app and eliminates context switching. Users can search or ask questions to get AI-generated answers and lists of the most relevant documentation from all of your help sources, including your knowledge base, docs, blog, and video libraries. You can also use HelpBar to navigate your app and launch actions, such as scheduling a meeting or viewing an interactive demo. The best products today use Command+K for in-app search and navigation. HelpBar makes that readily available within your app without engineering or new code. Give users a faster and more delightful self-serve experience that reduces friction and increases in-app engagement. Upgrade your user experience with this modern component, and supercharge your product-led motion. Sign up for HelpBar today. It's free and easy to set up in minutes. Check it out at helpbar.ai/lenny. That's helpbar.ai/lenny.

15. 55:17 – 1:01:31

    How Tom became VP of Product at Snapchat

    1. LRLenny Rachitsky55:17

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

    2. TCTom Conrad55:21

       At Pandora, I- I- I- I was the head of product and head of engineering, and our CEO was brilliant, but he was a product marketer, kind of... I mean, he was... Joe was, like, all things. He was a engineer by education, and a great marketer, and a great finance person, and, like, just such a, such a, a, a utility player at, at a very, very high level across e- every discipline. But he was also really, really good at letting his team do their jobs, so he really let me run product and engineering. And so, you know, not only did I have tremendous latitude to make good and bad decisions about product, I also got, really got a seat at the table to, like, help lead the company. So rewarding, so gratifying. Best professional experience that one could have. So, uh, I leave Pandora after a decade. I take, like, a, a year and try to figure out what I'm gonna do next. But after about a year, I got introduced to, to Evan. And it's kind of a funny story. Uh, I... A mutual friend sent this in- in this introduction over. Evan immediately responded and said, "Why don't you come down to Los Angeles and, like, have a coffee with me?" So I fly down. It's not clear if it's a job interview or, like, what it is really. I mean, I was just, like, lightly exploring things that were out there and was a big fan of what he was doing with Snapchat. So I spent, like, 45 minutes with him, and then I spent 45 minutes with the head of engineering, and another 45 minutes with, like, the head of legal. And then they tossed me into a conference room with, like, a dozen product designers, all in their mid to late 20s, many of which had gone to school at Stanford with Evan. I would come to learn, like, all really, really, really impressive, super, super talented people. But, like, you know, it was just, like, 10 of us sitting around a conference table. And it, it wasn't really clear that they knew why they were talking to me, but we had kind of a, you know, hour-long free-ranging conversation. And, uh, so I left and I thought it was like... It was like a, like a totally fascinating morning, but I wasn't sure what had happened really. I was like, "Well, were these interviews... Like, it all seemed very ad hoc. Is there a job opening?" Like, it was str- it was, like, a little odd. And I, uh, I went to lunch on Abbot Kinney and got a text from Evan's admin saying, "Can you come back to the office? Have you gotten on your plane yet?" I was like, "Oh, no, I was just, like, ordering lunch. I'll, I'll, I'll just come back right away." So I go back. Now it's, like, one o'clock in the afternoon. This entire thing started at nine o'clock in the morning. I sit down in the conference room. Evan comes in with a manila envelope and says, "We loved you. We'd like for you to be our VP of product." And, like, handed me a written offer. Like, all, all the terms, like, the stock compensation, the whole thing. I'm... Like, I'm gobsmacked. Like, I... Like, I'm, I'm, I'm, I'm flattered. Like, this is, like, really playing to my ego. I, like, I kind of can't believe that this company that feels like maybe the most interesting thing that's happening in consumer tech, that, you know, their, you know, notoriously brilliant and mercurial founder has, like, taken a- enough of a shine to me that he wants to, like, give at least some of the keys to the product kingdom over after such a short courtship. So I leave and, and when some of that buzz wears off, I start to wonder if there's, like, some red flags (laughs) later, maybe. So I tell Evan, "Listen, I'd like to come back and, like, meet more of the leadership team, spend more time with you, go a little deeper on what this means." And so we extend our courtship by another week or so, and I, you know, super impressed by the rest of the leadership team and the, the, the product thinkers and, and definitely designers and things that I was gonna get to work with on a daily basis. And so I take the job full knowing that it's, like, gonna be wildly different than Pandora, where I had all of this latitude to, like, kind of do whatever I might want to do. And in the, you know, the context of Snapchat, at best, I was going to be Evan's kind of right hand. You know, a person that, that principally executed his vision. And, and that's certainly what it was. I mean, Evan and I ended up having, like, a really great collaboration. But, uh, it was certainly most days I was... I was executing on his vision, both at a high level and very much in the details. And Evan's, Evan's truly brilliant. I mean... And he's also actually a really nice guy. I think in some ways he gets a, a bad rap for, uh... He has very high standards, but he's, he's a very kind person in my experiences with him. But it was a super exhausting job and not as soul-satisfying as I wanted it to be. And after a couple of years, I... Like I said, I thought maybe I just wanted to, like, make croissants or something. But one, one really, really big important lesson that I learned at Snap is about risk-taking. And, like, when you have the, the financial support and the, the foundational relationship with your investors that Evan has, it really allowed him to take these really big swings. You know-... acquire technology that he thought was game-changing, build features speculatively that maybe would be pruned in any other product or met planning process because the odds of them having an outsized impact were modest. And it just l- allowed him time after time to, like, make bets that paid off. And like, we forget about the ones that don't work, um, when there are so many home runs, you know, in those years. And we didn't have... Environmentally we weren't set up for that at Pandora, but I think in some ways, like, I wasn't temperamentally inclined to those kinds of big swings and I think I'm, I, I think I'm a ... I take bigger risks and encourage bigger swings now because of the things I learned from, from Evan and Snapp.

    3. LRLenny Rachitsky1:01:18

       That is an awesome story. It resonates a lot with what Brian shared about how he thinks about product now, which is kind of telling people kind of what to build versus very bottom-up, "Tell us ideas you have." Did that impact the way you

16. 1:01:31 – 1:05:51

    Tom’s philosophy on being involved as CEO

    1. LRLenny Rachitsky1:01:31

       run ... We're gonna talk a bit about you as CEO now, but I guess do you have a place that you try to be, uh, CEO as, "Here's what we're building"?

    2. TCTom Conrad1:01:40

       As a product-oriented CEO, like, how much you should kind of lean in to the details versus ... set direction and create an environment where great people can do great work, I suspect there's not one answer that applies to every company stage. You know? 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 would get in a room and we would turn over some problem or opportunity and we would talk ourselves out of every good solution because it wasn't perfect. I used to joke that, like, Apple was, like, the only place in the world where, like, a vote of a thousand to one was a tie, because that one person would be so thoughtful in their critique that the other thousand people would be like, "Hmm. That's right. That's right." And even though there's been this huge consensus of what the right answer was, we would talk ourselves out of making decisions.

    3. LRLenny Rachitsky1:02:50

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

    4. TCTom Conrad1:02:53

       He wasn't there.

    5. LRLenny Rachitsky1:02:54

       Hmm. Wow. (laughs)

    6. TCTom Conrad1:02:56

       So, um, so I think, I think what broke Apple out of that mode when Steve came back, and like they didn't vote anymore.

    7. LRLenny Rachitsky1:03:07

       Right.

    8. TCTom Conrad1:03:08

       You know? Steve was just making the call. And so I have some sympathy for Brian and, and, and Evan who have these big, you know, they have thousands of people working for them and as they delegate they, they grow frustrated that there's not progress at the pace that they're looking for and that there's indecision and the people on the teams report that there's just like churn and no progress and there's fightums and politics and all the rest and that as the CEO, as a pro- a brilliant product-oriented 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. Having said all of that, I also think that it can be a mistake to be that kind of leader in a smaller org because part of the opportunity in a small org is to, is, is to assemble a group of people that are incredibly talented that believe in your mission and work ... 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 as to try to surf that edge of like I'm really in the details so I deeply understand the business and the, 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, uh, outcomes. The one thing you'll always have as CEO is no matter how much you tell the team that when I swing by their virtual desk and say, "You know? I've been thinking about this little detail. Ah, it's not important right now, but like what do you think?" The, the, uh, you know, it's like nine out of ten times that person is gonna 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.

    9. LRLenny Rachitsky1:05:06

       There's a really good episode I had with Lane Shackleton from Coda and he shared this framework called flash tags that they use at Coda and I think it cames- comes from HubSpot of you 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."

    10. TCTom Conrad1:05:27

        I try to do a lot of that. I, I, I wish I could say that in my experience that that pays off. I, I-

    11. LRLenny Rachitsky1:05:34

        (laughs)

    12. TCTom Conrad1:05:35

        ... uh, it feels like an awful lot of time even.

    13. LRLenny Rachitsky1:05:36

        No, I get it.

    14. TCTom Conrad1:05:36

        I say very clearly just one person's opinion, focus group-

    15. LRLenny Rachitsky1:05:40

        Yeah, yeah.

    16. TCTom Conrad1:05:41

        ... of one. You know? Don't change your priorities to go work on this. Like it has more of an outsized impact on people's behavior than I do.

    17. LRLenny Rachitsky1:05:48

        Yeah. Easier said than done.

17. 1:05:51 – 1:10:37

    Tom’s current role as CEO of Zero, and what he’s learned along the way

    1. LRLenny Rachitsky1:05:51

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

    2. TCTom Conrad1:06:19

       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 we all do sort of, you know, soul searching about what I learned and what I might want to do next and, you know, as I thought about it, I realized that I, uh, I really wanted to, to move on to something where I could have like a direct impact on the culture and values of the company that I was involved in. I really, you know, got that opportunity at Pandora in a big way. And, you know, I had spent the-... five years of like Snapchat and Quibi working for Evan and Meg and Jeffrey, who are all incredible business leaders but have a, their own very specific sort of style and approach, and that leaves a, you know, a, a mark on the culture that's unique to the founder. And then as we descri- you know, discussed, like I- I'm, I'm always really interested in, in building things that I, you know, are near and dear to me. And I was particularly thinking about like what could I do that could have like a really positive impact on the world in, in my next chapter. I've been in an awful lot of media stuff through the years, video games and streaming services and so forth, and it seemed like maybe there was something that was, had a little bit more weight to it that I could, I could spend my time on. And so, uh, you know, I ... My first thought was I would start something. So I had an i- a work- a, a company idea, I was kind of quietly workshopping for some months, and completely independent from all of that, it's, you know, eight months into the pandemic and my own personal health was at an all-time low. I was 50 or 60 pounds overweight. My cholesterol was in the red zone. I mean, I was like out of breath climbing stairs, which is something that I had never encountered in my life before. I'm a bit of a yo-yo dieter and I'm always like kind of critical of my, like looking in the mirror, but I was never ever really worried about my health, my longevity. And suddenly, I was. And so my solution to that was to like go really deep on metabolic health, like just like thousands of hours of podcasts and videos and, you know, uh, glucose monitoring patches and Oura Rings and digital fitness gear and just to try to understand, you know, the things that impact health and longevity. And, and, um, you know, as much as I would like to report that what I learned is that there's some like magic pill that you can take, maybe some like off-label rapamycin or something, the truth is, is that, that to live a longer and healthier life, you really have to attack what I would call metabolic disease, which, you know, manifests in overweight and obesity and, um, pre-diabetes and diabetes and high cholesterol and, you know, all of these things that, that, that impact your, your long-term health. And so I found Zero in this path and was using it to, um, to help in my own, uh, sort of health journey. And, uh, Mike Mazur founded the company four and a half years ago, and he and I were talking in this interval about my own experience with the product. I was just kind of giving him product feedback and so forth, and he was telling me a little bit about his own entrepreneurial journey. And somewhere in the conversation, Mike said, "You know, I ... M- my intention is to step up into the executive chair role and to find a CEO for the company." So again, like in my story, just over and over and over this incredibly fortuitous thing happened. You know, I just sort of knew immediately that it sort of ticked all the boxes, you know. Here's a chance to, you know, lead something that already had some momentum to impact the culture and values in a really direct way and was like really, really close to my own personal journey. And so we know, we've got a great little company of 27 people. We've got more than a million users on the platform every month. Um, over 100,000 of them pay us with tens of millions of dollars of revenue through the years. And, you know, we've had double digit growth even coming out of the pandemic when lots of health and fitness companies kind of saw retreats. Um, and most importantly, it like, it actually works. You know? 75% of the people who, who use the platform lose weight. Um, 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. We have no paid user acquisition at all. Um, 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

18. 1:10:37 – 1:18:33

    How Zero builds product

    1. TCTom Conrad1:10:37

       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, you know, convert them through all of the funnels efficiently and get them engaged with the product and then get them to retain and sort of drive that up in a really systematic way? And, you know, I'm ... You look at my whole career, I'm definitely a person who started off thinking software development was like mostly an art form. You know? You find, you know, brilliant visionaries who have a deep understanding of human behavior and they craft solutions for problems that other people don't see and they make them delightful and they get all the little details right. And you know, when you've found product market fit for the art, then you sort of optimize them through a really sort of quantitative sort of take. And so I, I'm definitely a, a person that sees both sides of that sort of left-brained and right-brained, you know, equation that's, that's important in software. But here's the, here's the thing that's really ... my eyes have really opened to, uh, in the last two years. While companies are definitely the software that they make and the products that they deliver and that there is an art and science to that, as I described, there is also, if you step back, there is an equation that describes the business that talks about like how you turn investment into returns. And I suppose if I had come up through finance and been a business major that maybe that's the way that I would have conceived of companies to begin with. And so maybe it's a little embarrassing that I had to be 53 years old before I like, the scales fell from my eyes and I was like, "Oh, like companies are equations." And so, you know, when we first started talking about lifetime value and customer acquisition cost and getting those two things balanced and just to start thinking about the unit economics of the business, my natural instinct was to go immediately to sort of the leaf nodes of the equation. Like, oh, what percentage of people do we convert from installed to registered and from registered to trial? And these like very sort of way down at the bottom of all the funnels and to like ask the product team, like, "Let's try to optimize these."And in the process though, of trying to understand where we could take the business as we optimize those various dimensions, and trying to understand too which of the dimensions had the most leverage, I started building these ever more sophisticated models that describe the whole business. I mean, I've (laughs) I mean, in startups you get to wear a lot of hats, and definitely a hat that I'm wearing that I didn't anticipate at all is I am, I am the full-time FP&A guy for Zero. And so I, you know, I built this (laughs) 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, and all of our expenses and spend, and then can use that to predict future scenarios by sort of manipulating all of these variables. And I ... it's just, it's just not at all the way I ever thought about products before. And, and I know that you've got lots of listeners who are like, "This guy's an idiot." Like, that, you know, this is a, a fundamental way to contemplate, you know, uh, product work. But if there's anybody out there like me who sort of thi- thought of it as art first, and then sort of optimization in the details, it is really, really powerful to spend the time to create the model that describes the whole thing so you can identify, like, what are the high leverage points to focus on? So we've been doing a lot of that at the company in the last two years, and, um, it's really starting to deliver incredible results. You know, like everything in life, you just ... I mean, you, you sign up for things so you can learn, and, and, and, uh, that's the big one for me in the last year.

    2. LRLenny Rachitsky1:14:36

       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 it all the time. And so if you're not, you're missing out on, like, "Here's a way to influence them. Here's a way to ..."

    3. TCTom Conrad1:14:56

       It's so funny too, because it's a thing ... I suddenly understand something that mystified me through my entire career, which was, I'd go to board meetings and, you know, the investors would ask these probing questions, but they were really never about the product and what the product did and what the product roadmap was, and like what the features were and what this ... you know, it was all ... It all seemed to operate at this level that sort of was almost completely independent of the details of like the, what is the solution you put into the world? Which as a product, you know, oriented thinker was just completely baffling to me. And, and I, like, I now realize that they, they were, they were tilling the soil that I'm talking about. They were tilling like what ... It doesn't really matter what the screens are, what the features are, and like, you know, it, that ... I mean, it certainly matters, but, like, it ... there's another higher order way to look at a company, which is really about the optimization of this equation. And I think particularly if you sit on 25 boards, it's probably a much more efficient way to evaluate how your companies are doing and where to spend your time and how to help by, by thinking about them abstracted up at that layer. So, you know, I will never stop thinking about software development as being an art form, and I will never stop enjoying, you know, the days when I get to sort of lean in on the details. But, uh, but it's been, it's been pretty eye-opening.

    4. LRLenny Rachitsky1:16:18

       The other thing that stands out here, one is, I think this is especially true for consumer subscription apps, which I've done some research on, and basically they never work. There's, uh, Duolingo, there's Zero, which I didn't know how much scale you guys reached. Uh, my math here real quick. So you have a million users, 100,000 paying users. You charge, like, 10 bucks a month. I know there's a discount for an annual plan, but basically you're making somewhere ... a million dollars a month, which you don't have to confirm or deny it, but that's the math I just did, and that's crazy. So congrats. That's a rare, successful cons- consumer subscription app. It, like, never happens.

    5. TCTom Conrad1:16:53

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

    6. LRLenny Rachitsky1:17:08

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

    7. TCTom Conrad1:17:21

       One thing that's really fortunate for, uh, for Zero is Mike Masur, who founded the company, and I, have both been sort of around the block long enough and enough times that, you know, we remember 2008, we remember 2000. And so in these moments, like kind of in the pandemic, you know, there were companies in our category that were raising hundreds of billions of dollars with the intention of sort of throwing it at paid user acquisition. And we made a conscious decision to, to optimize the, the value of the organic traffic that we were getting and to drive our growth through LTV expansion rather than top of funnel expansion, which was candidly not in fashion in, you know, 2021, 2022. Turns out, it's much more in fashion these days as, as, as companies are, are, are called upon to be much, much more capital-efficient than they were during the, the pandemic era. And so, um, you know, it, it ... it's ... I g- I guess I feel somewhat fortunate that my, you know, my, my natural inclination as an entrepreneur is more in sync with the expectations of the market than, than it was for, for a while.

    8. LRLenny Rachitsky1:18:27

       Okay. So you've probably had the longest career arc of anyone I've had on this podcast.

19. 1:18:33 – 1:27:22

    Advice on work-life balance

    1. LRLenny Rachitsky1:18:33

       You've worked at all of these different companies in a lot of different phases. You're still at it, and I'm curious what you've learned about how to maintain your mental health and avoid burnout, essentially-

    2. TCTom Conrad1:18:44

       Mm-hmm.

    3. LRLenny Rachitsky1:18:44

       ... through this journey. You mentioned you take some time off. Is there anything else you found ... Or is that, is that a trick of just how to not burn out?

    4. TCTom Conrad1:18:51

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

    5. LRLenny Rachitsky1:18:55

       Mm-hmm. Yeah.

    6. TCTom Conrad1:18:56

       Um-

    7. LRLenny Rachitsky1:18:56

       But, uh, share it. Share for folks that may not be familiar.

    8. TCTom Conrad1:18:59

       So, uh-The idea is it's a Venn diagram, and there are four spheres. There's one, a sphere that's labeled what you love, there's a sphere labeled what you're good at, there's a sphere labeled what the world needs, and there's a sphere called what you can be paid for. And where they all intersect is this Japanese idea, ikigai. It's like the intersection of what you're good at, what you love, what the world needs, and what you can be paid for. If you find that, it's ikigai. And interestingly, y- your, your listeners should go and find this, because th- there, there are 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 th- the ones that are three but not four, I think because they are, they're the ones that are, like, close but not quite to this really satisfying thing. And so it's like when you, you find those, it's really easy to choose a job or to choose a, a, a path where you have three but not four, which is a really great recipe for feeling like there's something just out of your reach that's really important. Anyway, it's a great framework, uh, to think about your life and your career. So to start, I'm incredibly lucky that, like, it's all ikigai for me. Like, what I'm good at, what I love, what the world needs, what I can be paid for, like, they're just, they have 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, I..." Like I feel like, "I don't think I have any hobbies." And I think about, like, well, what kinds of things do I do on the weekend for fun? And it's like, you know, I'm like teaching myself After Effects or something, which I will immediately forget, but like I... You know, I just, like, it's just sort of fun to go really deep on some piece of, of so- of interesting software. So I'm very lucky and so that, I think that has been super sustaining for me, you know, like one of the reasons I've been able to do it as long as I have without really burning out is that just, like, it's what I do. And in some ways, it's why I come back to it, like, it's easy to say, "I'm gonna become a pastry chef," but, like, left to my own devices, like, I, I use software. I make software. It's my hobby, it's my, you know, passion, it's my... It's all the things. But a couple of thoughts about how one engages with their work. One thing is I, I'm, I'm really not, like, a hashtag hustling kind of, of leader. I, I... There was a woman that I worked with on the Finder just out of college that left a really big mark on me. My own style of work then, I think I mentioned it, my memory of, like, flashing, like, plinking the, the folder animation was like a 2:00 AM kind of thing. I mean, I was 23 years old, I woke up at 11 o'clock in the morning. I, you know, went to the office, I screwed around and played, you know, video games in the Apple Arcade and went to a couple of meetings and had lunch and stood at the whiteboard and pontificated about some nonsense, and then about four o'clock every day, I would start writing software and I would write software until 2:00 or 3:00 in the morning, and then I would go out to dinner with s- with people from the team in the middle of it and whatever. And so it, it kind of looked like I spent 14 hours a day six or seven days a week at Apple.

Episode duration: 1:40:03