Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Reddit, Grubhub)

1. 0:00 – 3:36

   Casey’s background

   1. CWCasey Winters0:00

      Every person on the product team is acting like they work at Google and have these infinite resources and infinite time to make sure everything is perfect. And there became such this focus on the right way of doing product management that no one's taken any risk. And I felt like, "Oh, am I responsible for this?" Like, I've created a bunch of, you know, frameworks on Reforge. You know, I'm onboarding these EPMs. It's like, "Is this... Is this my fault?" But, you know, you know, at Reforge we're building frameworks that are tools in a, in a toolkit. You pull them out when relevant. They're not a coloring book, you know, to stay, you know, inside the lines of.

   2. LRLenny Rachitsky0:38

      (instrumental music) Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Casey Winters. Casey was one of the first ever guests on the podcast, and the first to make a return appearance. He's a legend in the growth and product community, having worked with or advised companies like Pinterest, Reddit, Canva, Airbnb, Tinder, Thumbtack, Grubhub, and many more. He recently led product at Eventbrite for just about three years, and recently returned to full-time advising and he's exploring new opportunities. In our chat, we cover something he calls the zero interest rate phenomenon product manager and how to avoid that, what he's found works best when interviewing product managers, what impact he expects from GPT-4 on the role of product management, when to trust your instincts versus your team's insights and instincts, what are all the different kinds of network effects and how do you effectively leverage them, plus a great story about what Grubhub missed that let DoorDash and Uber eat their lunch. I always learn so much from chatting with Casey, and I am 100% sure you will learn a lot from this episode. With that, I bring you Casey Winters after a short word from our sponsors. This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics, while Amplitude unlocks the power of your product and guides you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free, visit amplitude.com. Amplitude, power to your products. This episode is brought to you by Eppo. Eppo is a next generation A/B testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Contentful, and Cameo rely on Eppo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to wasted time building internal tools, or trying to run your experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved about our experimentation platform was being able to easily slice results by device, by country, and by user stage. Eppo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles, and helping you easily get to the root cause of any issue you discover. Eppo lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscriptions, and payments. And Eppo supports tests on the front end, the back end, email marketing, and even machine learning clients. Check out Eppo at GetEppo.com. GetE-P-P-O.com. And 10X your experiment velocity.

2. 3:36 – 5:24

   What Casey is up to

   1. LRLenny Rachitsky3:37

      Casey, welcome back to the podcast.

   2. CWCasey Winters3:39

      Thanks, Lenny. Great to be here.

   3. LRLenny Rachitsky3:41

      You were the first ever return guest to my podcast. How does that feel?

   4. CWCasey Winters3:46

      I feel honored. Perhaps a bit unworthy. But, you know, I'll go with it.

   5. LRLenny Rachitsky3:52

      Well, you're both worthy and I'm honored as well. So thanks for joining me again. I have a lot of stuff that I want to chat about. But first of all, I'm just curious, what are you up to these days? I know you left Eventbrite as CPO, I know you're doing a few advisorships with startups, but how are you spending your days and what do you think is next for, for Casey Winters?

   6. CWCasey Winters4:10

      So I'm still, still spending some time with whatnot and Eventbrite as, as advisors. You know, I stepped back from the, the CPO of, of Eventbrite in October, but still working on some-

   7. LRLenny Rachitsky4:20

      Mm-hmm.

   8. CWCasey Winters4:20

      ... long-term marketplace strategy stuff, some growth strategy stuff. Uh, I'm on the board of a company called Beak, which is like Netflix for audio in Latin America.

   9. LRLenny Rachitsky4:30

      Mm-hmm.

   10. CWCasey Winters4:30

       And I'm doing some angel investing in, in marketplaces, in, in what I call tech debt as a service, which is, you know, what are startups that are building out things that were hard for my teams in the past to, like, build or maintain inside previous companies? The other thing I'm working on is revamping the product strategy program for Reforge. So-

   11. LRLenny Rachitsky4:48

       Mm-hmm.

   12. CWCasey Winters4:49

       ... I've got some things keeping me busy, but, but definitely not as busy as I was last year.

   13. LRLenny Rachitsky4:53

       This is, like, a rare, uh, free agent Casey Winters time. Should people reach out if they're interested in maybe working with you? What's your advice for people listening and like-

   14. CWCasey Winters5:00

       Yeah, I always love seeing how I can help companies, right? So everyone should err on the side of reaching out and seeing if I have time to help, if there's something they think I can help with. I just, you know, I love talking to startups. So yeah, absolutely. Like, can't, can't promise anything, but, uh, yeah, I, I just love talking to people about this stuff.

   15. LRLenny Rachitsky5:19

       Awesome. And we'll point people to how to get in touch with you at the end of the episode, and it'll be in the show notes too.

3. 5:24 – 7:26

   Why the CPO position is frequently short-lived

   1. LRLenny Rachitsky5:24

      But talking about the CPO role, so you're at Eventbrite, you're a CPO. It reminded me of a post you wrote about how hard the CPO role is, and there's some quotes that I recall in your post about how, one, if you ever ask a CPO, chief product officer, how they're doing, no one's ever gonna say, "I'm ju- I'm crushing it right now."

   2. CWCasey Winters5:41

      Yeah.

   3. LRLenny Rachitsky5:41

      And then there's this other quote about how you basically as a CPO just try to put some points on the board before you inevitably get fired. Why is that? Why do you find that, and do you still believe that to be true after, you know, leaving that role?

   4. CWCasey Winters5:53

      Yeah, I would say I still believe those things I said. Yeah, it was funny, um, a product leader who will remain nameless-

   5. LRLenny Rachitsky6:01

      Mm-hmm.

   6. CWCasey Winters6:01

      ... emailed me when I hit year three at Eventbrite and they said, "Congrats, you didn't get fired after two years. What's your secret?"

   7. LRLenny Rachitsky6:07

      (laughs)

   8. CWCasey Winters6:08

      You know, I, I think it's very hard to keep product-market fit as a CPO within a company for a long time. You know, the needs of the business shift over time, and of course we all have different strengths and weaknesses in our game. Like, no one's perfect at everything. And in general, you know, as an executive, it's just impossible to do everything perfectly, and any little misstep, mistake, or something you just miss can blow up in a major way. You know, frequently, CEOs have visions that can change and get misaligned with, with the product leader. And also, you know, with leadership roles, you don't get put on a PIP, right? Like-

   9. LRLenny Rachitsky6:43

      Mm-hmm.

   10. CWCasey Winters6:43

       ... if a CEO loses confidence, it's over, uh, immediately. So, nothing like that happened at Eventbrite. I started to see that the areas of leverage for a product leader were just less in my wheelhouse over time, and I just talked to my boss about it and, you know, we worked out something where I could continue to advise on the things that, you know, I'm uniquely good at, and, and find other people who are better at some of these other things that were maybe more important at the time. But yeah, it's, it's a really hard role, a, a really, uh, challenging role. You know, it can be a lot of fun, uh, and I, I, you know, I learned a lot from doing it. But yeah, I still believe, uh, and I think I've still yet to hear someone say they've really crushed it.

4. 7:26 – 10:15

   What Casey learned in his role as CPO of Eventbrite

   1. CWCasey Winters7:26

   2. LRLenny Rachitsky7:26

      Is there anything that you learned from that experience to s- to survive in that role for three years? You know, I imagine you have a lot of skills and you were very valuable to the company, but I don't know. Any... For someone that's in that role maybe right now, just like, here's something that I did that maybe you should do?

   3. CWCasey Winters7:40

      Uh, the first one I can think of is a big change from being a product leader to a, you know, a CPO or, or something equivalent, is you're actually a comp exec first and a product exec second. So, I think some mistakes I made, you know, early that I, I corrected successfully is, you wanna show that you are caring and paying attention to the overall business first before just taking care of your own, you know, product designers, product managers, researchers, whoever. So that's, that's advice I found myself doling out to other product leaders a lot more now that I've, you know, gone through it. You have to not only truly care, but sh- create the perception that you care about sales, about marketing, about, you know, legal, et cetera. Because first and foremost, you're expected to lead the business, you know, at, at that level. So I think that's something that I think is really important, and I think something else is really trying to diagnose, without as much bias as possible, where are the strengths and weaknesses of your team, where are the strengths and weaknesses of your product? Lay that out with your peers (laughs) and say, "Here's where we are. Here's where I think we need to go. Here's the timeline on w- which I'm gonna work to get us there." Because I think product's such a confusing, uh, discipline for people who aren't in it, like a sales leader, many CEOs, uh, you know, marketing leader, that they don't necessarily know what great looks like, and the things they know about great leadership, they don't know if you know those things.

   4. LRLenny Rachitsky9:18

      Mm-hmm.

   5. CWCasey Winters9:18

      So, you have to make it really clear, "Yeah, I know our OKRs are not as quantitative as they should be yet. That's because this team isn't ready for X, Y, and Z. This is where we're gonna get them to, but it, it's gonna take some time." So one of the things we did at Eventbrite that I thought was really helpful is, you know, when you go public, you tend to rotate over your executive team and get public company execs versus startup execs. So, uh, a few of us were new, and it's just like, "Hey, let's do a deep dive on product. Let's do a deep dive on customer support. Where is it at right now? What do you feel like your job is? What do you feel like are the issues you're facing? Where do you want to take it over the next three to five years? And then let's talk about it." And just forcing you to, like, write it all down is, is really helpful, but then it forces you to explain it. Um, and, and it helps the rest of the executive team get better company execs because, you know, now they really understand product a lot more deeply or understand finance a lot more deeply, whatever the function is.

5. 10:15 – 12:17

   The “zero interest rate phenomenon” product manager

   1. LRLenny Rachitsky10:15

      Speaking of, uh, gaps and opportunities for people in the company to level up, you've kind of been, uh, highlighting this trend that I thought was really interesting, uh, something you called a zero interest r- rate phenomenon product manager. Can you talk about what that is and what you've been noticing?

   2. CWCasey Winters10:32

      (laughs) Yeah, s- sure thing. So, this is something I started noticing while managing, you know, PMs and product designers at Eventbrite, and it's now coming up with, um, with Whatnot as I hire, help them hire new PMs, um, is the environment in which a lot of product managers have come up is, is very distorted from when you and I started doing this kind of work. I think we used to always describe PMs as, you know, this gang of misfits. We all started in different functions. We all had different strengths and weaknesses. And the PM team, you know, gained as a whole from that diversity of skills and, and previous experiences. So what I noticed is when we started doing product reviews at Eventbrite, if there was any sort of, like, uncertainty in a problem or a solution, the product manager, instead of, like, s- shipping to learn, would talk about all this research they have to do to, to really learn the problems, really learn a solution. You know, and, and my feedback would be like, "No, like, we... You know, user research is a scarce resource. We have to reserve it for the areas that have, you know, extreme uncertainty and a high leverage for getting to certainty." So if you're redesigning the login page for Eventbrite, you don't need to use that resource to learn what to do. Just go see what Fang and the top unicorns did. They probably did a good job. And, you know, even if they didn't, all of our customers also use those products, so they're gonna be familiar with us copying any approach that they've taken. So, I, I think we sort of forgot in the industry that many times the fastest way to learn is to ship.Uh, s- so then, if you actually get them to skip research and just go look at competitors...

6. 12:17 – 18:35

   Advice for thinking outside common frameworks

   1. CWCasey Winters12:17

   2. LRLenny Rachitsky12:17

      Hmm.

   3. CWCasey Winters12:18

      Another thing I was noticing is I'd get, like, a list of options other companies have done. But there would be no analysis of why those companies chose different options and what's, you know, most applicable, you know, for us. So i- it got me thinking, like, "Okay, every new person on the product team is acting like they work at Google and have these infinite resources and infinite time to make sure everything is perfect." And there became such this focus on the right way of doing product management that no one's taken any risk. And I felt like, "Oh, am I responsible for this?" Like, I've created a bunch of, you know, frameworks on Reforge. You know, I'm onboarding these UPMs. It's like, "Is this, is this my fault?" But, you know, you know, at Reforge we're building frameworks that are tools in a, in a toolkit. You pull them out when relevant. They're not a coloring book, you know, to stay, you know, inside the lines of. So, at one point I got so fed up I wrote, like, an internal blog post. And I called it On Best Practices and Breakfast Rituals. And I talked about how there were these articles about the morning habits of the most successful people. And if you try to do all those things, it'd take you, like, six hours every morning.

   4. LRLenny Rachitsky13:29

      (laughs)

   5. CWCasey Winters13:29

      And there was this article, I think it was on Business Insider or something, about this futurist at Google. And he talked about all the pills and food he eats for breakfast every morning to try to live longer. And the reporter estimated that it cost him one million a year to have these habits.

   6. LRLenny Rachitsky13:45

      (laughs)

   7. CWCasey Winters13:45

      So (laughs) I was like, "Hey, I want to make it clear. At Eventbrite we don't have that much money. We don't have that much time. There's no framework that allows you to not use your brain at this company and just follow some sort of process for success in, in this profession." So, I, I adopted this thing into, like, a, a public blog post that's on my blog now. But now that I've had some time outside of Eventbrite, I, I feel like I at least partially missed the mark on what's really going on. And, and, you know, you see this with, like, Whatnot, because one of the things I'm helping them with is interviewing iCPMs again, which I haven't, you know, done in a while. And it's fascinating interviewing a PM or managers early in their career, because Whatnot is a startup. And, and, you know, you know better than most of us, as a former founder of one, startups typically require us to wear lots of hats. You have to write SQL, you have to talk directly to customers, you have to prep marketing and sales. And most importantly, you have to make a lot of decisions under uncertainty, which you wouldn't necessarily expect a PM to do at, you know, say, at Google. But it all boils down to using your brain in different ways. You know, uh, Lisa, who's on our legal team, she called Eventbrite a, a public startup, because the pandemic basically erased her business-

   8. LRLenny Rachitsky15:01

      Hmm.

   9. CWCasey Winters15:01

      ... and we had to build it back from scratch. So now that I'm doing these interviews and whether they come from a small startup, a unicorn, a, or a public company, they all sort of look the same, because there's been so much funding to all these companies. Every company's been acting like they're Google with Google margins, meaning a lot of engineering support, a lot of design support, a lot of research support, lots of analysts around them. And they actually seem pretty ill-prepared for a real startup or even a public company with some uncertainty around it, like Eventbrite. So y- you start getting these weird responses in the interview process. You, you ask them to solve a problem, and they'd say things like, "I can't even begin to come up with solutions until I see all the data and talk to customers." And I'm like, "Yeah, I get that, that's something you would normally do if you took the job. But, like, you don't have the data. You can't talk to customers. Make a decision now. Like, what would you do? I want to see how creative you are. I want to see how much you're intuiting about the real problem and solution." And they can't really answer. And then, you know, my followup, which I don't ask but what I really want to ask, is like, "So when's the last time you used your brain versus followed a process someone else designed at your company?" 'Cause, like-

   10. LRLenny Rachitsky16:06

       Hmm.

   11. CWCasey Winters16:06

       ... I want the former, not the latter.

   12. LRLenny Rachitsky16:09

       Wow. Amazing. Uh, there's a lotta things I want to dig into here. And I was gonna ask why you call it zero interest rate phenomenon, but I think what I'm hearing is it's when interest rates are zero, everyone's got a lot of money, things are going great, everyone looks like they're killing it, successful, everyone thinks they've got it all figured out. And then when that goes away, it's like, "Oh, shit. Maybe, maybe not so."

   13. CWCasey Winters16:27

       And also, I think zero interest rates allowed every startup to operate like it was a public company-

   14. LRLenny Rachitsky16:32

       Mm-hmm.

   15. CWCasey Winters16:32

       ... with billions of dollars.

   16. LRLenny Rachitsky16:33

       Yeah.

   17. CWCasey Winters16:33

       And, you know, that's gonna go away over the next five years. And it, and it sort of takes us back to what product management used to be like, which was, you know, you didn't have all these resources around. You didn't have all this time to figure it out. Because if you don't figure it out now and make it work, you may run out of, you know, funding. Right?

   18. LRLenny Rachitsky16:51

       Yeah. Like, a very concrete thing that's changed is a lot of research teams have been laid off, because they grew really large and companies kind of found maybe we don't need the... Like, of all the things we can cut, it's probably an area we can cut.

   19. CWCasey Winters17:02

       Yep. For sure.

   20. LRLenny Rachitsky17:04

       There's probably PMs listening to this wondering, "Shoot, am I one of these?"

   21. CWCasey Winters17:07

       (laughs)

   22. LRLenny Rachitsky17:08

       "Am I just, like, following a bunch of frameworks?" What's your advice for someone that may fear that, "Oh, shoot. This is maybe who I am and I don't want to necessarily be this"? And what could they maybe do?

   23. CWCasey Winters17:17

       I always advise going to companies where you can, you know, learn quickly and, and try things. Right? And I think, you know, it's certainly okay to, like, learn a bunch of frameworks. There's a reason I've invested a ton of time in Reforge, 'cause I think it actually really does help people to see how other people have built things in a way that they can, you know, scale to their other companies. But you have to understand that the job is not to follow the process. The job is not to learn every framework possible. The job is to figure out how to add value to customers that translates into value to, to the business. And, you know, just reorient your north star if you've gotten away from that. When I joined Eventbrite, you know, there was this team that didn't ship anything in a quarter. And, you know, I went to the designer, who I knew, and, uh, you know, I know that he, you know, likes to, likes to get stuff out there and likes to get feedback. And I was like, "Dude, you didn't ship anything. Like, how could you have gone the entire quarter not shipped any of your designs and felt that that was okay? And if you didn't feel it was okay, why just censor yourself? Come to me."Tell me why this team is not letting you ship. There's just no way you can get better as a designer, there's no way you can have impact on the company, there's no way you can have an impact on our, on our users. So, um, you know, those are some things that, that come to mind to that question.

7. 18:35 – 21:16

   When to bring in research

   1. CWCasey Winters18:35

   2. LRLenny Rachitsky18:36

      So if you're a PM on a team that maybe isn't shipping, maybe is overusing research, do you have any advice of just like when it makes sense to invest in research? Say you have the resources, like is there kind of a rule of thumb you have of like, "Okay, let's actually spend the time on this," sort of stuff?

   3. CWCasey Winters18:51

      Uh, I think about it a little bit depending on the type of job you have and the types of customers you have. So, you know, the more scale you have tends to be you have less sophisticated customers because you're generally like, you know, a consumer thing where the customers are rational, they're not experts.

   4. LRLenny Rachitsky19:11

      Mm-hmm.

   5. CWCasey Winters19:11

      And that's generally where you just try things, you measure the impact they have, and you only really bring in user ch- research when the impact seems confusing, right? But you can run experiments, like you can get data really easily. So biased towards, you know, getting stuff out there and seeing what, what users respond to.

   6. LRLenny Rachitsky19:29

      In consumer, in consumer products is what you're saying?

   7. CWCasey Winters19:31

      Right. If you're super enterprise, it's kinda the opposite, right? Each customer, first off, is sophisticated and tend to be rational. They're paying you like six figures or more, and you could talk to the customers and sales who knows the customers really well directly, and they tell you what they want, they tell you what they're willing to pay for. You build it, they pay you, bing, bang, boom, right? It's not obviously as simple as that. But, um, you're basically doing the research directly with the customer and with the sales team and, and translating that to things that are strategic to, to the business. And I, I would say those are the two extremes probably most people are familiar with, but we now have a lot of companies in the middle where they have more customers. Those customers are more sophisticated, they're consumers, they're maybe employees at companies or they're small businesses. And that's where you have to be nor- more nuanced, and, and this is of course where Eventbrite was, on, "Hey, when do I really lean in on research? When do I lean in on data? When do I pay attention to internal feedback?" Uh, so, you know, for Eventbrite we really tried to focus research on the B2B side of Eventbrite where the problems seem big but not well defined enough. Or that problem's well defined, but we just really don't feel like we have the right solution yet. And, you know, if research is gonna be, um, a scarce resource, uh, inside the company, which I, I think it will in most places, you have to figure out where it's a high leverage area, which means either really big problem, uh, that we don't, we don't understand it well enough, or we know the problem's big, we understand it well, but we're just not sure if our solution's gonna at any way like, you know, hit the mark.

   8. LRLenny Rachitsky21:06

      Makes me think about some of the best researchers I've worked with, and they often tell me like, "We don't need to do research on this."

   9. CWCasey Winters21:10

      (laughs) Yes.

   10. LRLenny Rachitsky21:11

       "We have enough information. Like we, we have other things we should be doing."

   11. CWCasey Winters21:13

       I, I love it when they say that. Yes.

   12. LRLenny Rachitsky21:15

       Yeah.

8. 21:16 – 21:59

   What Whatnot does

   1. LRLenny Rachitsky21:16

      This would have been a really good segue to another topic I wanna talk about, which is around i- gut instincts versus team expertise, which we're gonna get to, but I have a couple more questions a- along these lines.

   2. CWCasey Winters21:24

      Sure.

   3. LRLenny Rachitsky21:25

      You talked about interviewing PMs at Whatnot. Can you actually describe Whatnot just 'cause you mentioned a couple times, just so people know what we're talking about there?

   4. CWCasey Winters21:31

      Oh, sure. So Whatnot's a, a live streaming marketplace, mostly focused on the collectibles market. So, you know, sellers, whether it's like, you know, baseball cards or women's handbags or sneakers, you know, they'll go live on video and show you the products they have that they're selling and people who are watching the stream can engage with the sellers and bid on, you know, different items. So kind of like Twitch meets eBay-

   5. LRLenny Rachitsky21:53

      Awesome.

   6. CWCasey Winters21:53

      ... would be a good way to describe it. Yeah.

   7. LRLenny Rachitsky21:54

      Awesome. And I'll just mention I'm a tiny angel investor in that company.

   8. CWCasey Winters21:56

      Oh, that's why you brought it up. Okay, I get it.

9. 21:59 – 23:29

   Casey’s approach to interviewing PMs

   1. CWCasey Winters21:59

   2. LRLenny Rachitsky21:59

      (laughs) Yeah. I just wanted to make sure people understood what this word was 'cause it's like a, a fun word, Whatnot. Uh, but what I wanted to actually get to is you said you were interviewing a lot of project managers for them.

   3. CWCasey Winters22:09

      Yeah.

   4. LRLenny Rachitsky22:09

      What is your approach to interviewing PMs? What do you find is a, is a really good signal for someone that's gonna be successful?

   5. CWCasey Winters22:14

      I feel like the whole thing's gotten so performative.

   6. LRLenny Rachitsky22:17

      Mm-hmm.

   7. CWCasey Winters22:17

      It's like interviewing is handing out Oscars based on who's prepared the best tell me about a time response-

   8. LRLenny Rachitsky22:23

      (laughs) Mm-hmm.

   9. CWCasey Winters22:24

      ... versus actually assessing like who can do the job we're hiring for. So it's like most PMs are better PM interviewers than PMs now. There's this quote from a movie called The Way of the Gun, I don't know if you've ever seen it.

   10. LRLenny Rachitsky22:35

       Nope.

   11. CWCasey Winters22:35

       Uh, but Benicio del Toro says in it, it's like, "These days they wanna be criminals more than they wanna commit crime."

   12. LRLenny Rachitsky22:41

       Mm-hmm.

   13. CWCasey Winters22:42

       And I think about that quote a lot when it comes to interviewing. So I would say I'm a bit contrarian here in, in my approach. I don't ask about your work history. I don't care about your perfectly practiced answers.

   14. LRLenny Rachitsky22:55

       (laughs)

   15. CWCasey Winters22:56

       I'm gonna give you real scenarios that I expect from the role. I wanna hear how you'd approach them. And if you can't come up with a few reasonable ideas, figure out how to test them quickly without analyst support or research, I'm just not interested. And I'm not saying this is a perfect approach. Interviewing is a very lossy format. But the more I can see them do the job we're hiring for with questions, whether it's a presentation, a prompt, that gets me the most comfortable that they know the job they're signing up for, that they've shown in a practice scenario they can do it, and they actually enjoyed it in some way.

10. 23:29 – 24:27

    Red flags in interview responses

    1. CWCasey Winters23:29

    2. LRLenny Rachitsky23:29

       Are there like red flags you look for in these interviews? Like one is maybe you said, oh, but like, "I can't even begin to answer this without research and data." Is there anything else?

    3. CWCasey Winters23:36

       Some things I pay attention to is if they're talking about solutions that are gonna take a long time to get signal from.

    4. LRLenny Rachitsky23:44

       Mm-hmm.

    5. CWCasey Winters23:44

       Um, you know, whether it's months and months of engineering time before you actually, you know, see the impact on users or the, or the business, I think that's, you know, always great. If they're not factoring in the amount of time it will take, uh, i- in general is not, you know, a, a good sign. And not thinking a bit more holistically about the types of metrics they expect to improve versus track to make sure like they haven't gone down. Those are some things that I pay a lot of attention to.

    6. LRLenny Rachitsky24:11

       How much do you think, uh, they're intimidated by being interviewed by Casey Winters? How much do you think that factors in?

    7. CWCasey Winters24:16

       (laughs) I, I think you overestimate my importance or awareness in the community. I think most people have no idea who I am when they start talking to me.

    8. LRLenny Rachitsky24:25

       Mm-hmm.Well, I don't know.

11. 24:27 – 27:47

    The future of product management with AI

    1. LRLenny Rachitsky24:27

       Another thought is there's this meme that GPT-4 is gonna ... or 5 or 6 or 10, is gonna replace product managers. And any time some new feature comes out, people will put out these videos of, "Oh, look. They're doing all the PMs jobs." What's your take on the future of PM in, in AI, if any?

    2. CWCasey Winters24:41

       Well, I think if you thought the PM job was just filling in the latest, you know, Reforge or Shreyas framework, and then getting, you know, that automatic FAANG promotion every year and a half-

    3. LRLenny Rachitsky24:53

       (laughs)

    4. CWCasey Winters24:53

       ... then yeah, you're gonna get replaced by AI. But I think the real PM job is the least likely to get replaced over time, because you need, you know, real subject matter expertise. You need to, you know, be trading off a lot of different types of things in, in making good decisions for the company and, and for your customers. So, in terms of using AI now as a PM, I'd actually be cautious in, like, the current iteration of the cycle for PMs. You know, it's a tool that's trained on sounding smart rather than always necessarily being smart. I was at Eventbrite the other day and someone was telling me how they were loving the new Notion AI integration. And she asked me if I had used it. I said, "No." She's like, "Oh, you totally need to. Hey, go ask it your bio. It's really cool." And I said, "All right, let's just do it on your screen." So, she did and, like, my bio said I started my career at Google and worked on Google Trends and a bunch of other s- products, none of which happened.

    5. LRLenny Rachitsky25:49

       (laughs)

    6. CWCasey Winters25:50

       Like, it was just complete nonsense. It did have some stuff that did happen. It knew I worked at Eventbrite and it knew I worked at, you know, like Pinterest and stuff. But like, uh, like half of it was just completely made up. It sounded plausible, uh, but it wasn't actually, you know, true. I think where I'm more inclined for PMs to try to get leverage out of something like GPT-4 is a lot of the tedious work that's maybe not their specialty to begin with. So, you know, if you're not great at, like, Excel or Google Sheets and you need to model something, you can ask it how to format something. That'll probably be perfect. Or, like, how to get some Zapier integration to work, like, it probably knows how to do that really well. So, I think at this point, it's a pretty good no-code/low-code tool, and it's obviously gonna become a lot more than that. But for a lot of these other use cases that people are touting, there's a decent chance it confidently tells you the wrong thing. And, and that would scare me as a PM.

    7. LRLenny Rachitsky26:45

       I've had the exact same experience. I had it s- uh, describe what I've done, and it was, like, 70% mistaken.

    8. CWCasey Winters26:51

       (laughs) Yep.

    9. LRLenny Rachitsky26:53

       Is there anything you've found value in yet with GPT of any kind in your, in your work? Or is it still kind of just poking around in novelty for you?

    10. CWCasey Winters27:00

        Yeah. I've had a couple of those things where it's like, "Hey, how do I actually get this weird thing done?"

    11. LRLenny Rachitsky27:06

        Mm-hmm.

    12. CWCasey Winters27:07

        And it's been like, you know, clear bullet points, take these steps. And I'm like, "Oh, great." Like, this was actually really hard to find on Google. So, things like that, I actually quite like it for. Uh, so that's where my head goes to, like, more confidently use it. 'Cause of course, I'll try it, and if it's wrong, I'll learn where it's wrong-

    13. LRLenny Rachitsky27:26

        Let's start with it.

    14. CWCasey Winters27:26

        ... so that it's, it's low risk. But it's been right on some of those things, and it's like, "Oh, cool. I couldn't figure out how to do that." There's something on Google Docs that I needed to figure out how to do that was kind of fancy. I asked ChatGPT, it told me how to do it, and I was like, "Oh, great."

    15. LRLenny Rachitsky27:39

        I had a similar experience where I just needed a formula in Google Sheets and I just told it, like, "I need this thing," and it just gives me the actual formula.

    16. CWCasey Winters27:45

        Yeah. That's, that's so magical when it happens.

12. 27:47 – 37:17

    Founder intuition vs. team expertise

    1. CWCasey Winters27:47

    2. LRLenny Rachitsky27:47

       Yeah. I don't know. I'm not that good with Sheets formulas. Uh, shifting course a little bit. You also wrote this really interesting post on founder intuition versus team expertise, and there's a lot to it. And I think it's a really interesting topic, 'cause it's this classic discussion that startups have. How much should a founder trust their gut and how much should it be top-down, "Here's what we should be doing," versus the team kind of bottom-up, figure out what to build? And so, I'd love to spend a little time here. So, maybe just to start broadly, what is this? You kind of came up with a framework of how to think about when founder intuition should overrule, say, team expertise, and how that changes over time. So, maybe just talk about that.

    3. CWCasey Winters28:26

       You know, if founders are lucky/good enough to find product-market fit, they've usually built up all this intuition about their customers, about their product and their business that are really hard to explain to others and may even be, like, subconscious. So, when they start to hire people, you know, these people will come in with a lot of, you know, excitement, you know, ideas, maybe even really relevant experience, especially, you know, senior leaders. And I've seen some founders who are like, "Cool. I need to let these experts start to own these areas and get out of the details." And I think that's actually the opposite of what you want, because none of these people know the business as well as you yet. You actually need to direct them until they show you they've really got it and are making better decisions than you would.

    4. LRLenny Rachitsky29:16

       Mm-hmm.

    5. CWCasey Winters29:16

       So, I've ... This is not a founder example, but I remember when I hired, uh, Erika Warren to build our, our loyalty program at Grubhub. And she now leads growth at, at Change.org. And after a month or so, she was like, "Dude. You're in all my meetings. I got this." And, you know, that let me know she was in a different part of the situational leadership framework than I had put her in. So, I backed away and, you know, she crushed it from there. Founders will put a lot of new leaders in that delegate bucket too quickly. It's like, "Oh, it's theirs. They got it. They know more than me," when founders actually know the right answer and should just tell them. Uh, and this can, of course, change. Like in the case of Erika, you know, if you hire the right people, they, they do get smarter than you. You can and should start delegating. And many founders don't notice the signals where their founder intuition has been usurped by team expertise.

    6. LRLenny Rachitsky30:06

       Hm.

    7. CWCasey Winters30:06

       Or maybe it's just ebbed in effectiveness over time. And, and that, of course, makes sense, right? Founders have all these different things they're dealing with and your employees can really dive deep in certain areas. So, I encourage employees to proactively signal both directions. Like, "Hey, I need direction from you," or, "Hey, I got it from here. Trust me on this one."

    8. LRLenny Rachitsky30:27

       Interesting. So you're saying as a founder, the heuristic should be if you feel confident about a decision, generally you should be clear like, "Hey, I think I know what we need to be doing here." And don't just, like, make people feel better necessarily by just saying, "Okay. You tell us what you want to do." And then on the flip side as a dr- as an employee at the company, if you feel really confident about something, make it clear to the founder, like, "I really think this is the right move." Eh, is there anything more you wanna add there?

    9. CWCasey Winters30:55

       Yeah. Well, I mean, there's obviously the, the feedback loop of that, of like, you know, w- what happens when you do-

    10. LRLenny Rachitsky31:01

        Yeah.

    11. CWCasey Winters31:01

        ... either of those things. Um, so, you know, depending on the, the founder's response to that or the employee's response to that, there's kind of different approaches, you know, you can take.

    12. LRLenny Rachitsky31:13

        And part of this, uh, yeah, this cool chart of just, like, over time the founder expertise becomes less and less relevant. And I guess is that because they just don't spend as much time with the customers 'cause they have other stuff going on, or they hire people that are smarter, and then over time team expertise goes up?

    13. CWCasey Winters31:26

        If you're lucky enough to scale a company, there's just more and more things going on that all will reach the founder in some way. E- e- but it means more breadth and less depth on any particular issue. And, uh, the reverse is true for, you know, the people you hire, right? They're able to get really deep into things that maybe you were really deep into two years ago, um, but, you know, you just can't... you can't stay deep in anymore. So I- I- I built this, you know, chart on, um... or, or I guess I should say table on the different phases of-

    14. LRLenny Rachitsky31:59

        Mm-hmm.

    15. CWCasey Winters31:59

        ... you know, a startup, right? And when you're, you're finding product-market fit, like, everything goes through the founders. Like, you cannot outsource that. Um, and then, you know, when you start scaling the company 'cause you found product-market fit, it's the first time that founders run into this, like, classic problem of what got you here won't get you there. What got you to product-market fit was iterating on product and doing things that don't scale. Guess what? You found a product that works. Don't do that anymore. Make it scale. Don't come up with new products. You found the one that works. The reason I came up with this, um, you know, framework, uh, originally is when I was at Grubhub, uh, you know, we were scaling pretty nicely and, and fairly organically. I, I think, um, Mike and Matt, the founders, had intuited these phases of, like, building a company, like, pretty well. But we acquired a competitor and, you know, I saw how that company we acquired operated.

    16. LRLenny Rachitsky32:52

        Hmm.

    17. CWCasey Winters32:52

        And even though they were largely in the same phase as us, they still operated like they were founding the company. Like, everything was going through the founder. And, you know, intuitively I was like, "Oh, this is why we're acquiring you and not the other way around." (laughs) Um, so, uh, I think it's really hard for founders to get those signals or- organically, and I think it's up to us as employees to help. And you know, the, the founders can listen to those signals or not listen to those signals, but that's part of why, why we're here. But we should also give those signals when we're confident we really get it, not like coming day one being like, "I know what your sales strategy should be. You're doing it all wrong." 'Cause chances are the founders weren't doing it all wrong. They knew something you don't know about yet.

    18. LRLenny Rachitsky33:34

        What is it that you think made it such that you won and they didn't? Is it because they didn't invest, they didn't shift to scaling and delegating to their employees as much as the founder just telling everyone to

    19. NANarrator33:42

        Yeah.

    20. CWCasey Winters33:42

        Correct, right? Like, the, um... everything was, like, not moving as quickly because everything had to go through the same person to get done, so it just allowed them to not launch as many markets, to not sign up as many restaurants, to not figure out as many, you know, growth channels, uh, you know, as we had done.

    21. LRLenny Rachitsky33:59

        Got it. So they just bottlenecked themselves and they weren't able to move as fast because the founder thought they needed to make these decisions and they were still the ones that knew everything.

    22. CWCasey Winters34:08

        Yep.

    23. LRLenny Rachitsky34:08

        That makes me think about most companies, eh, maybe not most, but many founders just, like, believe they have the answers. Like, they are confident they know what to do-

    24. CWCasey Winters34:18

        Right.

    25. LRLenny Rachitsky34:18

        ... and it's rare they get to a place of like, "No, I actually don't." (laughs)

    26. CWCasey Winters34:22

        Well, I, I would say no one gets to, n- no one gets to it super intuitively.

    27. LRLenny Rachitsky34:26

        Hmm. Any advice for either as a employee at a company with a founder like that or a leader of just how to push back and help the founder understand maybe you should let go and trust people to make decisions?

    28. CWCasey Winters34:38

        I think the first thing is you have to understand that it's their company, not yours, and the founders have impossible jobs. They're not going to scale perfectly with the needs of the company. Like, it's just something's gonna be off, and it may be because there's a whole lot of hubris by being the one of a thousand startups that made it, or you know, they just have personal styles. But they can run the company any way they want. And I think it's sometimes surprising when founders actually want to run things suboptimally. Like, I think we've seen examples where founders just wanna build cool shit versus focusing on what customers want, or they're too obsessed with the design. They're always rebranding, redesigning things in ways that confuse customers. And you know, of course that's gonna happen and those are some of the, the worst cases. Um, but I think, you know, if you do state your point, you've actually built up the expertise, you're confident, and you are refuted for whatever reasons, you have to find ways to be contrarian and prove you're right. And different founders have different forms of feedback they listen to. It might be talking to other CEOs, or other operators, or trusted advisors, certain customers. Some might be very data oriented, so you just run the experiment and ask for, you know, forgiveness after you prove it worked, wh- wh- whatever. Like, everyone's got, like, a different thing they respond to. So you try to figure out what actually influences, you know, the CEO and build that case, whether it's through an experiment, the right customer intro, the right external advisor. And if they rebuke that as well, then you gotta disagree and commit or find a new company to join or start your own. Like I said, it's their company. They can make the call. I remember when I joined Pinterest...I was just coming off, you know, 100X increase in user growth from Grubhub. And I was ready to drive the same sort of impact at Pinterest. But no one knew who I was. I didn't come from Facebook or Google like most of the other people or Pinterest. No one gave a shit about Chicago startups at the time. So, you know, when they didn't trust my proposals, I just went and talked to the heads of growth at all the startups they did respect. I talked to Dropbox, I talked to Facebook. And when they said all the same things I was saying, but I said that they said it, not me, that was sadly more convincing. But I didn't care, 'cause I still got what I wanted out of it, which is to, you know, do the right thing to grow the company.

    29. LRLenny Rachitsky37:09

        And now you're one of those people that people go to. If Casey says it, it's probably the right way to do it.

    30. CWCasey Winters37:13

        Whether I'm correct or not, it is a role I sometimes play in the ecosystem,

13. 37:17 – 40:00

    Adding the delivery driver app at Grubhub

    1. CWCasey Winters37:17

       I will admit.

    2. LRLenny Rachitsky37:17

       Is there an example where you were convinced something was the right way to go and the founder at one of the companies you worked at had a different opinion and they were... They ended up being right?

    3. CWCasey Winters37:25

       When I was at Grubhub, one of the ideas one of the founders came up with was to build an app for delivery drivers. So at the time, you know, uh, restaurants had their own delivery drivers. They did not work for us. And we wanted to build an app for the delivery drivers so you could see where the food was along the way, so you could-

    4. LRLenny Rachitsky37:41

       Hmm.

    5. CWCasey Winters37:41

       ... know if it was five minutes away, whatever, right?

    6. LRLenny Rachitsky37:43

       Mm-hmm.

    7. CWCasey Winters37:43

       Um, Domino's was the first to have done this at the time. And we thought that would, that would make a bunch of sense. And I was just like, "How am I supposed to convince the delivery driver who doesn't have a relationship with us to download this app from Grubhub, to actually turn it on, to create, you know, anxiety for the consumer of like, they maybe didn't take the right turn or whatever?" I was like, "I don't think this makes sense. No one's gonna use it." And, you know, Mike and Matt, like, overruled me and, and pushed us to do it. And in the long run, it ended up being quite necessary because of the innovations around DoorDash and Postmates and, and later Uber Eats into having their own delivery network and, and us needing to counter that. That's, of course, a key piece of technology that needs to lever- have parity with those new services. So, that was an area where perhaps they were thinking a little bit lo- more longer term than I was. And, you know, I was not able to kind of get where they were going on, on the longer term time horizon of, of how this would be actually ultimately adopted and useful.

    8. LRLenny Rachitsky38:39

       This is an awesome segue to the next area. But real quick, how did they get drivers to start using this app? Was there anything really clever they did?

    9. CWCasey Winters38:46

       I, I think it was fairly low adoption for a while. Uh, and leveraging basically restaurant authority. So if we were able to push on our restaurant customers effectively to say like, "Hey, if you use this, well, it'll get you more orders. We'll get you prominence in the, the UI," things like that, to then push down, you know, to their direct relationships with the drivers to get them to adopt.

    10. LRLenny Rachitsky39:10

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14. 40:00 – 43:10

    Network effects

    1. LRLenny Rachitsky40:00

       Okay. So, shifting to our last topic that I was excited to chat about is around network effects and marketplaces and SaaS and kind of how those things connect. I feel like you have the clearest way of thinking about and explaining network effects. So maybe just to start, can you just, like, simply explain what is a network effect and then the different types of network effects that exist?

    2. CWCasey Winters40:20

       Yeah. No pressure after you say that, right?

    3. LRLenny Rachitsky40:23

       (laughs)

    4. CWCasey Winters40:23

       Yeah. So, uh, at its core, a network effect is when a product or a business gets better with more users or customers using it. And there's three types that I tend to focus on. So, the first and probably the most well known is called direct network effects. And that's when every additional user makes the product better for all the existing users. So when someone joins WhatsApp, other people can talk to them that they, that wouldn't be able to talk to them before. And that makes WhatsApp valuable, more valuable for everyone. And then there are cross-side network effects, where there's two distinct types of users. And adding an additional user on one side of the network makes it more valuable for all the types of users on the other side of the network and vice versa. So when a restaurant joins Grubhub, it creates more selection for users to order food. And when more users start ordering more food, Grubhub becomes more attractive for restaurants to join so they can make more money from, you know, delivery orders. The, the last network effect I focus on is data network effects. And that's when the quality or cost of something improves as more data is collected through the product. So, when you save content to Pinterest to a board, it gives Pinterest signal on the quality of that content, its relevance to other pieces of content since they're shared to the same board, and more signal on your preferences. And this allows Pinterest to better recommend more content to you as well as to other people who look like you and share similar interests. So, uh, one thing that's tricky about these network effects is most people talk about network effects in the context of social network, not marketplaces or, you know, SaaS, like my background. And the thing that's really tricky in understanding social networks is they're traditionally described as these direct network effect businesses. But all of them have to become either cross-side and/or data network effect businesses over time. The only companies that stay direct network effect businesses are these pure commu- communication tools like Messenger, iMessage, WhatsApp. And there isn't a clear path to make money with those, but if you wanna sell ads, you're becoming a cross-side network effect business. And also creators versus consumers creates a cross-side network effect business. If you wanna get better at personalization, guess what? You're recommending content by leveraging, you know, data network effects.

    5. LRLenny Rachitsky42:44

       I love that. No, you, you nailed it. I imagine marketplace founders listening to this may be wondering, "Hey, how do I ... Can I add on these additional network effects? Can I evolve towards one of these?" And what you're saying is, not only can you, you need to eventually.

    6. CWCasey Winters42:58

       I agree, right? I think, you know, they're a great form of defensibility, first off. So do they make sense for every business? No. But in a lot of cases, in order for you to evolve properly and continue to grow, they can become a necessity.

15. 43:10 – 44:05

    Why Zillow is a sticky product

    1. CWCasey Winters43:11

    2. LRLenny Rachitsky43:11

       Are there any other examples of marketplace companies that come to mind that did a great job evolving or adding one of these network effects, or are just like interesting?

    3. CWCasey Winters43:19

       Let's take some inventory, right? Um, so I think Zillow's really interesting, in that a real estate listing site is not particularly an interesting product, but the ability of saying very rarely do, you know, both sides of this network, people who are buying homes and selling homes, need to connect. But I can find a way for the brand to connect with both of them by giving real time pricing information on the value of homes. And that creates a much stickier product for both sides. I think that was a, a pretty genuine, uh, innovation, you know, that other people have tried and, and rarely been as successful with. So that's, that's one that definitely, uh, sticks with me, you know, off the top of my head.

    4. LRLenny Rachitsky44:04

       Great.

16. 44:05 – 51:47

    How Grubhub’s network effect got taken over by DoorDash and Uber Eats

    1. LRLenny Rachitsky44:05

       We've been talking about Grubhub a lot, and Grubhub had some pretty strong network effects and-

    2. CWCasey Winters44:09

       Yep.

    3. LRLenny Rachitsky44:09

       ... in large part thanks to the work you did. And one of the benefits of network effects is it creates a barrier to entry. It's hard to replicate and compete with a company where they already have all this network effect. But famously, Grubhub got disrupted by DoorDash and Uber Eats. And I know you talk about how that happened and why that happened, and it'd be cool to hear just like what do you think they could have done differently, and what happened where their network effect got eaten, eaten for lunch, pun intended.

    4. CWCasey Winters44:35

       Sure. Uh, it's a great question, and I think people do mistake any form of network effect as this perfect form of defensibility.

    5. LRLenny Rachitsky44:42

       Mm-hmm.

    6. CWCasey Winters44:42

       They're the best form of defensibility, but that doesn't mean they're immune to disruption. And I think the main way this happens with cross-side network effects that we typically talk about for marketplaces is when a disruptor dramatically expands selection. So I want to be clear. Uh, I left Grubhub at the end of 2013 before said lunch was eaten.

    7. LRLenny Rachitsky45:02

       (laughs)

    8. CWCasey Winters45:02

       So what I'm communicating is more like public knowledge of watching-

    9. LRLenny Rachitsky45:05

       Mm-hmm.

    10. CWCasey Winters45:06

        ... these amazing companies compete, rather than, like, being inside the fire at the time.

    11. LRLenny Rachitsky45:11

        Right.

    12. CWCasey Winters45:11

        But one important thing to remember is Grubhub was an asset-light marketplace model. Restaurants did their own delivery through their own delivery drivers that they hired. And I wrote this post for, you know, Andreessen Horowitz a few years ago about supply, strategies, and marketplaces. So, uh, in that, like, you really need to be comprehensive or have exclusive inventory. And, uh, Grubhub strived to be comprehensive. We show every restaurant that delivered to you, even if we didn't work with them directly for online ordering. So what happened about a year before I left Grubhub was that these competitors started to raise their seed rounds or series As to build delivery networks. Postmates and, and DoorDash were the, the first two that rose to prominence. Uber Eats would come later, but they actually started with a pretty different business model. And this is an extremely different business. You're hiring drivers. You're managing lo- logistics. So we call this a heavily managed marketplace model, as you are now facilitating the transaction versus just connecting buyers and sellers and taking payments, like, like Grubhub did. So on the one hand, you have Grubhub, this extremely high margin business, and these businesses coming up are actually negative margin businesses. At least they were for a long time. So in 2013, Grubhub acquired Seamless, its closest competitor at the time. And, you know, Seamless still had a lead on Grubhub in New York, partially because it had this corporate program where law firms and banks and consultants got lunch stipends you had to redeem by ordering the food through Seamless. So Grubhub operated in these dense cities and, and s- and suburbs like, like, like in New York, because those are the only places that had restaurants that had delivery. DoorDash, when it started, operated in less dense suburbs and worked with restaurants that had never done delivery before, and they would provide, you know, the delivery drivers themselves. So this allowed DoorDash to grow without much competition in the early days. And these companies also took some real gambles. Uh, one of the things they did is they delivered from restaurants they didn't have an agreement with.

    13. LRLenny Rachitsky47:21

        Hmm.

    14. CWCasey Winters47:21

        And that caused controversy and lawsuits. But what it meant is when these companies did launch in the cities to go after Grubhub, it felt like DoorDash and Postmates and Uber had dramatically larger selection of restaurants to choose from. And Grubhub was definitely no longer near comprehensive. And, you know, back when we talked about cross-side network effects, the more selection of restaurants, the more attractive it is to users, you know, and vice versa. So at that point, you know, Grubhub's put in a very peculiar position. It had gone public after raising $80 million in venture capital and raising $100 million in an IPO, telling investors it's an extremely prof- profitable, high growth, asset-light marketplace. But now it's got disruption pressure from operationally insensitive negative margin delivery services that were raising $100 million every six months from the private markets. So what Grubhub assumed is that these businesses were just structurally unprofitable, and that VCs would stop subsidizing them eventually. Of course, that didn't happen. They kept raising more money. DoorDash eventually raised, you know, multiple billions of dollars in, in this market. And part of what they used that money for was to lock up agreements with national chains, which Grubhub never worked with. It was always like the local mom and pops, and promotions and discounts o- on the demand side. So all of this is happening, and then the pandemic hits. And all of those negative margins turned positive for DoorDash for the first time, if I understand things correctly.And on top of that, all this corporate ordering that we got from Seamless no longer mattered because no one goes to the office anymore. So this gambit really paid off and DoorDash just took the market. Grubhub then tried to copy the approaches of DoorDash and Postmates, and they wrote kind of this famous letter saying that they still thought the approaches were stupid, but they were... their hand was forced, which is kind of funny to read in retrospect. Um, so, you know, a lot of armchair thinkers are like, "How could GrubHub have been so stupid to let DoorDash take the market that they built?" And look, I'll admit, GrubHub made some mistakes, but I think it would have been extremely hard for GrubHub to come out on top here. So let's say, in 2014, after you IPO, you do actually think what DoorDash, Postmates, and Uber are doing are smart. What do you do? Go to investors that you promised high growth and high profits and say you need to raise more money and debt to compete with negative margin upstarts in a way that will destroy all that potential profit you mentioned? The stock would drop 90%. A lot of your employees would leave because their stock is now worthless. And on top of that, building a delivery network is a heavy operations play that matches none of your core competencies. So to me, that feels like a death sentence. So I think the only play here was to buy DoorDash as early as possible-

    15. LRLenny Rachitsky50:14

        Mm-hmm.

    16. CWCasey Winters50:15

        ... and let DoorDash and their operationally heavy culture eat Grubhub from the inside out. I think Grubhub probably could have acquired them multiple times. For whatever reason, it never happened. It would have seemed pretty risky had GrubHub done that. Investors probably would have hated it, but it would have been their Netflix moment where, you know, Netflix bet it all on streaming, and they bet right. And this is all incredibly easy to say in hindsight. But I think what I've learned, you know, now that I'm more senior, uh, in my career is during existential threats, you know, it's like when Nassim Taleb says, "The only rational reaction is overreaction."

    17. LRLenny Rachitsky50:55

        Hmm.

    18. CWCasey Winters50:56

        Un- unless you have a real viable reason to assume otherwise, you got to assume the disruptor is right, uh, and base your strategy on them playing an optimal game, and I... whereas I think, you know, GrubHub assumed the disruptor was wrong and that it would all play out eventually in their favor, and it clearly didn't.

    19. LRLenny Rachitsky51:14

        Wow, I have never heard that full story. That was amazing. Thank you for getting in so much detail there. And-

    20. CWCasey Winters51:19

        I don't know how much of it is right, but-

    21. LRLenny Rachitsky51:21

        It seem- (laughs) seems right from the outside. And it's interesting that it's like a version of innovator's dilemma. Usually, innovator's dilemma is people come and s- do something cheaper at the low end of the market. And in this case, it was more they were doing something that they didn't believe would scale. It was, like, just much more inefficient-

    22. CWCasey Winters51:36

        Correct.

    23. LRLenny Rachitsky51:36

        ... even though it was a better experience. And is that, is that innovator's dilemma, or is that some other version of innovator's dilemma? 'Cause to your point, they couldn't almost go after it.

    24. CWCasey Winters51:45

        Uh, I, I think it is in spirit,

17. 51:47 – 54:43

    Don’t underestimate the competition

    1. CWCasey Winters51:47

       for sure.

    2. LRLenny Rachitsky51:48

       The takeaway there that you've learned is don't underestimate someone that's trying to do something that's gonna eat your lunch eventually, even though it feels like a terrible business model.

    3. CWCasey Winters52:00

       Right. Like, i- if the market's rewarding it, the market will probably find a way to make it profitable. And, uh, you know, it's essentially when everyone's find, like, a more efficient network effect for demand on the- on the- on the marketplace side, uh, you probably need to copy that, like, as soon as possible.

    4. LRLenny Rachitsky52:17

       Mm-hmm.

    5. CWCasey Winters52:17

       And if you can't copy it, own it, right? Like, buy it. And I think we've seen this a few times. Like, Rover and Wag was another interesting example of this, um, where they found a more frequent use case that fit the same supply and demand, and, you know, Rover just copied it as soon as, as soon as possible. And that ended up, you know, working out for them in a way that, you know, it didn't as much for GrubHub.

    6. LRLenny Rachitsky52:37

       I just did a talk recently on marketplace, uh, growth strategy, and someone asked me a really interesting question. If you were trying to go up- up against a DoorDash or an Uber today, what would you do? And my answer is just, like, money was so freely available at that point that they were able to s- Like, a lot of this was spend. They had so much money raised.

    7. CWCasey Winters52:55

       Yes.

    8. LRLenny Rachitsky52:55

       You said they're raising $100 million every six months. Like, is it even possible in today's climate where you can't actually raise that much money to have any sort of chance to beat a DoorDash or an Uber?

    9. CWCasey Winters53:05

       Yeah, I mean, clearly they took a- a advantage of the zero interest rate environments that we talked about earlier. That is not a replicable strategy in 2023.

    10. LRLenny Rachitsky53:14

        Yeah.

    11. CWCasey Winters53:14

        So any approach to compete with them has to be competing on a very different angle, um, because yeah, they can spend you into the dust. So, you know, we'll see if anyone's able to build a way that creates new supply and market. I think you and I have seen a couple of earlier stage examples of that. We'll see if any of them scale. Or something that feels cheaper or more fun on the demand side, that would be like another way to potentially disrupt things. I think another thing that was working pretty well the... before the pandemic in building disruptors was focusing on the pickup use case, which, you know, DoorDash cannot do as easily. Like, they've tried, right? But, like, their whole value prop is the delivery network, which you don't need for pickup. Uh, but of course, the pandemic put a lot of those startups grinding to a halt as well. So, you know, there's always angles, but you're gonna need to be incredibly clever because just attacking with a war chest is not really gonna work.

    12. LRLenny Rachitsky54:09

        Yeah, I noticed a lot of startups launching that are trying to do white label delivery for restaurants so they don't have to really rely on DoorDash, but that may be- maybe that's a wedge to get in and eventually they do-

    13. CWCasey Winters54:20

        Yeah.

    14. LRLenny Rachitsky54:20

        ... a DoorDash sort of thing.

    15. CWCasey Winters54:20

        And I would say I'm pretty skeptical of those because they're just not really building the network effects on the demand side.

    16. LRLenny Rachitsky54:26

        Mm-hmm.

    17. CWCasey Winters54:26

        They're just more like SaaS businesses, and I think they'll struggle to be, you know, multi-hundred million dollar in revenue businesses 'cause the take rate is typically, like, you know, a third or a fourth of what, you know, a DoorDash can charge.

    18. LRLenny Rachitsky54:39

        Perfect segue to my next question. I only have a couple more.

18. 54:43 – 1:02:30

    SaaS adding marketplace and vice versa

    1. LRLenny Rachitsky54:43

       There's this, uh, concept and I think pull from marketplace founders to add a SaaS tool eventually-

    2. CWCasey Winters54:51

       Mm-hmm.

    3. LRLenny Rachitsky54:51

       ... and have both business models, and then there's often the reverse where a SaaS company wants to add a marketplace. And I know this question is something you get a lot.And so just a question for you. Does this work? Are there examples where they've added this additional way of making money? And which direction do you find is most often successful and not successful?

    4. CWCasey Winters55:11

       You know, the canonical example that a lot of these founders use is, is OpenTable. And that always felt really unfulfilling to me, um, 'cause it's very old at this point. Probably the younger people listening to the podcast are like, "What's OpenTable?"

    5. LRLenny Rachitsky55:24

       (laughs)

    6. CWCasey Winters55:24

       And I think, you know, that business has incredibly underperformed the market it operated in.

    7. LRLenny Rachitsky55:29

       Mm-hmm.

    8. CWCasey Winters55:29

       So it, it had a good exit. It sold for $2.6 billion, I think, to booking.com. But Booking subsequently wrote that value down, like, below a billion.

    9. LRLenny Rachitsky55:39

       Hmm.

    10. CWCasey Winters55:40

        So, you know, that's not really the outcome I think we're looking for traditionally-

    11. LRLenny Rachitsky55:42

        Mm-hmm.

    12. CWCasey Winters55:42

        ... in marketplaces.

    13. LRLenny Rachitsky55:43

        And maybe explain, like, what it was initially, the SaaS tool versus-

    14. CWCasey Winters55:46

        Oh, sure.

    15. LRLenny Rachitsky55:46

        ... an actual marketplace.

    16. CWCasey Winters55:47

        So, so OpenTable promised both a SaaS tool that would help you understand, like, what tables were open and where to seat people, so for, like, the host at the, in the front of the house in a restaurant, but also bring in additional reservations to fill up your restaurant, right? Because I think what people misunderstand about restaurants is they're like, oh, these restaurants are these incredibly low-margin businesses. And it's like, yeah, they are because they're paying the rent no matter what happens. So once you're already paying the rent no matter what happens, you're incentivized to pump as much food out the kitchen and to get as many people seated in-house as possible. So people would say, like, "Oh, Grubhub and DoorDash, you're charging too much." Uh, and it's like, no, like, delivery orders and catering orders are basically pure margin to restaurants. The chefs are already there. The, you know, the rent is already being paid. The more things we pump out of the kitchen, the more money we make, um, which is why, you know, restaurants are, are willing to pay higher fees. Like, r- these restaurants are not stupid. They're not being, like, misinformed, right? So OpenTable, well before there were any delivery startups was like, "We're gonna fill up your tables. And we're gonna give you the software that helps you manage your tables most effectively to, to make the most profit."

    17. LRLenny Rachitsky57:01

        Got it. Okay, great. So keep going. (laughs)

    18. CWCasey Winters57:03

        So that's OpenTable. So look, this is definitely the strategy we are working on with Eventbrite, where we started with something that was more SaaS-like, y- you know, enabling, uh, easy payments and, you know, certain tools to make event creators' businesses more efficient. And we're layering in more the traditional marketplace value prop of demand, you know, driving more ticket sales for these event creators. And, you know, I would say it's got a ways to go to be working really well. And what does working really well look like? It's when the marketplace model unlocks those cross-side network effects that make it easier to grow. So, you know, event creators, when Eventbrite started, they would just go do their own marketing to bring people to Eventbrite to transact on their events that they had listed there. And now Eventbrite drives, you know, 25% of the ticket sales itself. And, you know, that percentage is growing faster-

    19. LRLenny Rachitsky57:52

        Oh, wow. That's amazing.

    20. CWCasey Winters57:52

        ... than... Yeah. It's growing faster-

    21. LRLenny Rachitsky57:53

        I didn't know that.

    22. CWCasey Winters57:53

        ... than the rest of the business, which is great. But it probably needs to be closer to, like, 50% to unlock those real cross-side network effects. And that would mean that creators start selecting Eventbrite because of all the demand Eventbrite has versus the quality, you know, of the SaaS tools. So, uh, that's obviously something we're working on. Um, Faire is a company I advised more recently that I think has, uh, unlocked this model in, in, like, the reverse, where Faire is a wholesale marketplace between independent retailers and brands so that you could sell products at these retailers, like a, you know, a boutique, you know, in, in your local neighborhood. So Faire built the marketplace first, and then it later built a SaaS tool that allowed the brands to onboard their current, you know, retailers into the platform and get better terms, uh, on payments and, and free returns. And it didn't charge anything to use the SaaS tool for any rebookings that happened through that platform. But what that did is it onboarded more independent retailers that they could cross-sell to other brands without, you know, needing to use a sales team. And when they cross-sold, of course Faire did, you know, take their percentage on those transactions. So I, I think that model has worked out really well, well and, and Faire has grown quite quickly.

    23. LRLenny Rachitsky59:06

        And so the examples you gave, uh, Eventbrite was a SaaS tool trying to add a marketplace.

    24. CWCasey Winters59:10

        Yep.

    25. LRLenny Rachitsky59:10

        Faire is an example of a marketplace adding a SaaS tool. And is the takeaway there that it's, in your experience, it's generally more you're gonna have a better time if you're a marketplace w- adding a SaaS tool versus the other way around?

    26. CWCasey Winters59:24

        Yeah. I, I think that's right. So I think, you know, uh, I don't know when it was, it was maybe, like, 2015 or whatever, a, a bunch of investors started writing about SaaS to marketplace transitions. And, like, that's the transition Eventbrite's going through. It's going to work, but it's hard. And it's not replicable for a lot of other SaaS businesses. You need to have a direct relationship with your customer's customers, first off. Those customers need to have needs beyond that single supplier. Usually it's, like, a discovery value prop, you know, for other suppliers. And you be n- need to build, like, this totally new skillset, uh, to build tools for your customer's customer, who is very different from your current customer.

    27. LRLenny Rachitsky1:00:02

        Mm-hmm.

    28. CWCasey Winters1:00:03

        Whereas, you know, marketplaces that add a SaaS component, you know, as a customer acquisition tool, like Faire, or a workflow or retention tool to, you know, increase retention or reduce disintermediation, I think you'll see that be a lot more common approach and, and much more replicable.

    29. LRLenny Rachitsky1:00:20

        Is this just rooted in the fact that marketplaces are incredibly hard no matter whether you start with them or whether you add them? Like, is that the root of the issue here?

    30. CWCasey Winters1:00:28

        I, I, I think that's a good way to frame it. I- it's... So if, you know, if you're building a startup in 2023 and you're like, "Oh, I'm gonna build this SaaS business, and then five years later I'm gonna build this marketplace business on top of that," it's kind of like, it's gonna take a long time for you to de-risk the hardest part of that strategy. Whereas if you get the hard part done upfront, it opens up a lot of amazing, you know, adjacencies, different ways to grow. So I, I think there's definitely truth in that statement.
19. 1:02:30 – 1:05:43

    Defining marketplaces

    1. CWCasey Winters1:02:30

       dig into it.

    2. LRLenny Rachitsky1:02:31

       It might be helpful just to define like what makes it a marketplace. In my eyes, it's you are driving demand to supply. That's like the nuance, right? Because otherwise you're just a tool that they're using to do something they want to do.

    3. CWCasey Winters1:02:40

       Yeah. E- e- exactly right. It's like the primary value prop of why supply signs up is that you're gonna bring them extra business. And if you have, you know, customer buyers and sellers, but the primary reason supply signs up is for tooling or payments, like how Eventbrite started, that's not really a marketplace. You know, I call it a SaaS-like network. Some people might just call it a SaaS business, a payments business, whatever the case may be. But it's, it doesn't really have those cross-side network effects that we associate with marketplaces.

    4. LRLenny Rachitsky1:03:10

       What this makes me think about is Patreon and Substack, and interestingly when I was looking at early Patreon days, what I understand is they want it to be a marketplace. They want it to be a place where artists come, they collect payments, and then people can discover artists to patronize. And what they found is nobody needed... that wasn't a problem anyone had.

    5. CWCasey Winters1:03:30

       Exactly. Exactly.

    6. LRLenny Rachitsky1:03:30

       (laughs) I'm not looking for-

    7. CWCasey Winters1:03:30

       I'm not looking for other people that donate money to... same with GoFundMe, right?

    8. LRLenny Rachitsky1:03:34

       Mm-hmm. And so with that story in mind, when I was chatting with the Substack people early on, I was like, "This is exactly what you're going to run into." No one's like sitting around looking for more newsletters to subscribe to. But shockingly, they've actually pulled it off.

    9. CWCasey Winters1:03:47

       Yeah.

    10. LRLenny Rachitsky1:03:47

        They have a really wild network effect going now and, uh-

    11. CWCasey Winters1:03:50

        I've been very impressed with what they've built. I don't know if I'd call it, you know, a marketplace yet.

    12. LRLenny Rachitsky1:03:56

        Yeah. Yeah.

    13. CWCasey Winters1:03:56

        But, uh, I, I think they were able to abstract away the version of what you just said to something that was actually useful, which is, yes, I don't want more emails to subscribe to, but I do, I am fundamentally interested in more articles relevant to my interest, and no one has really solved that super well. Twitter was a very hacky form of that, you know, where I follow you and then I see when you post a new blog because you, you tell everyone on Twitter you post a new blog, but it isn't built for that. Whereas, you know, the Substack reader will now allow me to be like, "Oh yeah, sure, I'll subscribe." So I really like what they've done. It'll be interesting to see, you know, how big a business that is and, and how it all plays out. But I think their execution has been really solid.

    14. LRLenny Rachitsky1:04:39

        Awesome. I feel the same way. And it is... I also wasn't sure whether it makes like it's worth calling a marketplace, but for whatever it's worth, 80% of my new signups are coming from Substack's network, the recommendations feature and they're onboarding things like that. Like-

    15. CWCasey Winters1:04:51

        Do you think that's unique to you because you are already a top one percenter Substacker? Or is that a meaningful number for newish players? Like if I finally switch my (laughs) email list to Substack, which has been on my list for a long time, uh, you know, that probably won't be the same percentage for me, right?

    16. LRLenny Rachitsky1:05:11

        Absolutely not. Yeah, no, I think there's definitely... if you're there first and people know of you, more people will recommend you. But I think over time more and more people start to recommend you. I think they released a stat that something like 40% of their new users are coming from a recommendation or new signups or something like that. So it's pretty widely happening, but I don't know how much of that is just the top 10.

    17. CWCasey Winters1:05:33

        Excellent.

    18. LRLenny Rachitsky1:05:33

        So it's pretty incredible. It was a really innovative feature and good job, Substack. And we had, uh, their head of product on this podcast talking about that exact feature for a whole, for a whole hour if you're interested.

20. 1:05:43 – 1:13:15

    Tips for B2C subscription startups

    1. LRLenny Rachitsky1:05:43

    2. CWCasey Winters1:05:43

       Awesome.

    3. LRLenny Rachitsky1:05:43

       Okay. Final question and then we have our very exciting lightning round, and this is around consumer companies and s- consumer subscription companies. I know you work with a lot of founders that are building consumer subscription companies and just consumer startups in general.

    4. CWCasey Winters1:05:57

       Yeah.

    5. LRLenny Rachitsky1:05:58

       You often tell me how they're incredibly hard to build into thriving businesses. Can you just talk about why consumer subscription startups are so hard-

    6. CWCasey Winters1:06:06

       Yeah.

    7. LRLenny Rachitsky1:06:06

       ... and products are so hard?

    8. CWCasey Winters1:06:07

       I feel like you're making this quite a downer podcast, Lenny, but, uh...

    9. LRLenny Rachitsky1:06:10

       This is... pe- people need to hear the, uh, the truth, you know? There's a lot of happy talk out there and a lot of posts, "Here's how you do this."

    10. CWCasey Winters1:06:16

        Sure.

    11. LRLenny Rachitsky1:06:17

        And sometimes you can't.

    12. CWCasey Winters1:06:18

        I think in order to understand these businesses, you have to start with why do investors like B2B SaaS? Why do they like B2B subscription? And I think the way most people respond to that question is they're like, "Oh, predictable revenue," right? And it's like, ah, sure. I mean, that's cool and all, but e- I think that's actually not the most important thing. So I, I'd argue there's two great attributes of B2B SaaS. One is that businesses are more predictable in how well they retain. They're rational. You can understand who are good versus bad businesses for your product, as well as which ones are gonna grow versus go out of business. And more importantly, the second thing that's great about B2B SaaS is net dollar retention. So what is net dollar retention if, if you don't work at SaaS? Well, a-As a SaaS company, some of your customers are gonna churn. Some of your customers are gonna stay. And normally, outside of potentially current macroeconomic conditions with all the layoffs, when customers do stick around, they tend to spend more. Either they buy more seats if you're a seat-based model or they use the product more if you're a usage model. So, the SaaS company just makes more money in year two, year three, et cetera. So, consumer subscription just doesn't have any of these benefits. Consumers are way less predictable, they tend to retain worse than businesses, and they also don't have net dollar retention characteristics. So, if the user retains paying you in year two, you probably making the same amount that you made from them in year one, not more. What that means is you need higher user-based retention than a B2B SaaS businesses with more unpredictable users, and it's a lot higher than I think, you know, founders tend to think. We're talking annual retention that needs to be north of 60, perhaps even 70%. So, you look at who's actually been able to do that at scale? And it's a really small list. Netflix in the US, Amazon Prime, Spotify, Duolingo I think is emerging as, as one of these players that's making it work. And when you look at how they do it, they're either doing it with massive OpEx and economies of scale or through a network effect or some other bespoke growth loop that's not that easy to replicate. So, Duolingo has a strong data network effect, the- the lessons get better the more people use it. You know, Beak, the company I'm on the board of, has a cross-end network effect between creators who create the content and the listeners, and the creators bring a lot of, uh, distribution from their existing, you know, uh, social networks to bring, you know, c- new people in the app to listen. Netflix and Amazon, they spend billions of dollars, you know, on content. So, I think the default path of like, "I'm gonna spend money on paid acquisition. I'm gonna retain half of my audience year over year," that's just a path to going under eventually. And I think what's interesting about these businesses is you can model it, so you can learn when it's gonna happen. You can learn like, you know, when the retention dips and when you can no longer

    13. LRLenny Rachitsky1:09:18

        (laughs)

    14. CWCasey Winters1:09:18

        ... properly acquire users. And if you wanna look at like a model in real time, just look at Blue Apron. The, the company raised $300 million in an IPO that valued it at $2 billion. It's worth $50 million today on the New York Stock Exchange. And I think people understand now if they didn't before that paid acquisition tends to get worse as you scale. You, you know, you target the best customers first. They have great conversion, great retention. And then as you expand your targeting o- of new customers, every one of those metrics gets worse until it's no longer profitable. It maybe two years from now, it maybe could be five years from now, but eventually it'll be no longer profitable. And what network effects allow you to do is they allow your product to get better faster than the customers you target get worse, normally through increased selection like, you know, some of the examples we gave, you know, with DoorDash and, and others.

    15. LRLenny Rachitsky1:10:11

        Such a cool topic. I, I actually have a post about this that I recalled now as you're talking about it. And just to kind of double-click on the retention point a- and it's like freaks you out when you really get into it, that say your retention is like 70% like cohort retention for a year. I forget the math, but like every three or four years you basically have to rebuild your entire user base because it just, it keeps trickling out, so your growth just has to continue.

    16. CWCasey Winters1:10:34

        It's mind-boggling. You run out of humans.

    17. LRLenny Rachitsky1:10:37

        (laughs)

    18. CWCasey Winters1:10:37

        Like, it's, it... Yeah, it's really hard. So, like if you can retain people incredibly well, meaning those people just never churn, yeah, you've got a great business. But look at the effort the companies that have done that are doing to do that. Spotify doesn't make profit. Netflix, Amazon, they spend so much money to try to do that. And how replicable is that for a startup? I'd rather say like, "Let's try and get some network effects involved here. Let's get our customer acquisition cost to zero. You know, um, let's think about other ways to monetize because this alone feels like hard."

    19. LRLenny Rachitsky1:11:08

        And this is also why a lot of these companies pivot to B2B. They realize, uh, there's, they're not gonna get anywhere with B2C. The other lesson I took away 'cause I interviewed a lot of these early B2C subscription app founders employees, and I think about companies like, uh, Grammarly, Duolingo, Noom, forget there are a few more. One of the other trends across them all is they're all very efficient and very small for a long time because they needed time to figure out how to make anything work and then just continue to stay small and super scrappy.

    20. CWCasey Winters1:11:37

        I think that's a great point. It was an interesting case study between Calm and Headspace.

    21. LRLenny Rachitsky1:11:41

        Mm-hmm.

    22. CWCasey Winters1:11:41

        'Cause Calm remains like 10 people forever. (laughs)

    23. LRLenny Rachitsky1:11:44

        Wow.

    24. CWCasey Winters1:11:44

        And you know, He- Headspace had gone into like, you know, hundreds of people. And Calm, like basically never lost money. And that allowed them to be, you know, allowed them to pivot easier during, you know, massive changes like, you know, app tracking transparency like threw a wrench into all paid acquisition. So, if you're not losing money, like cool, you have time to figure out how to like grow again. But if that increases your burn by like $100 million, you have a lot more of a panic on your hands.

    25. LRLenny Rachitsky1:12:12

        So, maybe just to tie the loop, tie the knot, close the thread on this, uh, topic. If you're a B2C subscription founder, what would be some takeaways that you would want to put in their head to think about how to maybe survive?

    26. CWCasey Winters1:12:26

        Yeah. So if... What your plan is is to use paid acquisition on top of a freemium model to get a percentage of people to convert and hopefully stick around forever, I'd pivot right now. Like, I just can't see it working. So, how do you pivot? Well, how do you make it social so that people are bringing in other people? How do you get a supply side to the, you know, content or education or whatever you're building and make it in the supply side's interest to refer people? Like, you have to do something that's either, you know, building some more organic growth loops into the business or building network effects into the business, or else likeWe could go spend two hours and model out exactly when you're gonna run out of money. Like, it's just that predictable. And you know, a lot of founders don't like to hear it when I tell them that, but I'd rather them hear it now than learn it three

21. 1:13:15 – 1:14:58

    Lightning round

    1. CWCasey Winters1:13:15

       years from now.

    2. LRLenny Rachitsky1:13:15

       Well, we've reached our very exciting lightning round. I'm just gonna dive right in. What are two or three books that you've most recommended to other people?

    3. CWCasey Winters1:13:23

       Definitely The Goal by Eliyahu Goldratt, um, which explains how my brain works pretty well.

    4. LRLenny Rachitsky1:13:31

       Hmm.

    5. CWCasey Winters1:13:32

       Uh, Thinking, Fast and Slow by, uh, Danny Kahneman. I took a lot of the behavioral economics classes in, um, my MBA program and, and then his book came out like a year after, so I just like absorbed it as quick as possible.

    6. LRLenny Rachitsky1:13:48

       Wait, was you a professor or that was just the, the topic?

    7. CWCasey Winters1:13:50

       Uh, some of his like pupils were professors of mine, yeah.

    8. LRLenny Rachitsky1:13:54

       Amazing.

    9. CWCasey Winters1:13:55

       Um...

    10. LRLenny Rachitsky1:13:55

        Very cool.

    11. CWCasey Winters1:13:56

        And then the third is a book called Profit from the Core by Chris Zook.

    12. LRLenny Rachitsky1:14:02

        Amazing. That's a new one. I love when there's new books being added to the collection.

    13. CWCasey Winters1:14:05

        There you go.

    14. LRLenny Rachitsky1:14:06

        Okay, next question. Favorite recent movie or TV show?

    15. CWCasey Winters1:14:10

        Uh, well, well, Party Down just came back, uh, and that's like-

    16. LRLenny Rachitsky1:14:14

        I've been watching that.

    17. CWCasey Winters1:14:15

        ... that's one of my favorite-

    18. LRLenny Rachitsky1:14:16

        I've never heard of it.

    19. CWCasey Winters1:14:16

        It's one of my favorite comedies of all time.

    20. LRLenny Rachitsky1:14:18

        Yeah.

    21. CWCasey Winters1:14:18

        Yeah, go back-

    22. LRLenny Rachitsky1:14:18

        Cool.

    23. CWCasey Winters1:14:19

        ... go back and watch the first couple seasons if you haven't.

    24. LRLenny Rachitsky1:14:20

        That's what I've been doing.

    25. CWCasey Winters1:14:21

        Okay.

    26. LRLenny Rachitsky1:14:21

        That's what I've been doing.

    27. CWCasey Winters1:14:21

        Great, okay. Uh, other things like The, The Last of Us is great. You know, I really enjoyed the, the video games. Severance is great. Station 11 is great. I, I loved the book too, but I thought that was really good. Movies? There, there haven't really been and a lot of great movies lately, but I, I did re-watch, uh, Kicking & Screaming from the '90s and it really holds up well. It's, uh, I don't know how many of you have heard of it, but it's about a group of college kids who graduate, but they just decide not to leave campus and start their lives and they just stick around campus. Um, so I- I really enjoyed that one.

Episode duration: 1:17:43