Lenny's Podcast: Product | Career | Growth
00:00:00 · Casey Winters
[00:00:00] S0: Every new person in 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.
00:00:41 · Lenny Rachitsky
[00:00:41] S1: 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 four 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 led DoorDash and Uber Eats 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 AB 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 GrowTeam stack. This leads to wasted time building internal tools or trying to run your experiments through a clunky marketing tool.
00:02:57 · Lenny Rachitsky, Casey Winters
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 analytics, and helping you easily get to the root cause of any issue you discover. 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 getepo.com, geteppo.com, and 10x your experiment velocity. Casey, welcome back to the podcast. [00:03:39] S0: Thanks, Lenny. Great to be here. [00:03:41] S1: You're the first ever return guest to my podcast. How does that feel? [00:03:45] S0: I feel honored, perhaps a bit unworthy, but, you know, I'll go with it. [00:03:52] S1: 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 wanna 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 adviserships with startups, but how are you spending your days, and what do you think is next for for Casey Winters?
00:03:52 · Lenny Rachitsky, Casey Winters
[00:03:52] S1: 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 wanna 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 adviserships with startups, but how are you spending your days, and what do you think is next for for Casey Winters? [00:04:09] S0: So I'm still still spending some time with Whatnot and Eventbrite as it... As advisers. Know, I stepped back from the CPO of Eventbrite in October, but still working on some long term marketplace strategy stuff, some growth strategy stuff. I'm on the board of a company called Beak, which is like Netflix for audio in Latin America. And I'm doing some angel investing in in marketplaces and 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. [00:04:48] S1: So I [00:04:49] S0: got some things keeping me busy, but but definitely not as busy as I was last year. [00:04:53] S1: This is like a rare, 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...
00:04:53 · Lenny Rachitsky, Casey Winters
[00:04:53] S1: This is like a rare, 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... [00:05:00] S0: Yeah. Look, I always love seeing how I can help companies. Right? So everyone should on the side 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, yeah, I I just love talking to people about this stuff. [00:05:18] S1: 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. But talking about the CPO role, you're at Eventbrite, your 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 I'm crushing it right now. [00:05:40] S0: Yeah. [00:05:41] S1: And then there's this other quote about how you basically, as a spiel, 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?
00:05:53 · Casey Winters
[00:05:53] S0: Yeah. I would say I still believe those things I said. It was funny. A product leader who will remain nameless 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? 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, 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, if a CEO loses confidence, it's over 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, worked out something where I 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 really, challenging role. You know, it can be a lot of fun, and I I, you know, I learned a lot from doing it. But, yeah, I still believe, and I think I've still yet to hear someone say they've really crushed it.