
46 segments available
Casey Winters is a longtime and legendary advisor and operator. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit and until recently was the Chief Product Officer at Eventbrite, where he managed the PM, design, research, and growth marketing teams. Before Eventbrite, he led growth and product teams at Pinterest and Grubhub. In today’s episode, we discuss what Casey calls the “zero interest rate phenomenon” product manager and how to avoid becoming one. He provides valuable insights on thinking outside popular frameworks, shipping products efficiently, and avoiding overreliance on user research. We explore the three types of network effects, how to leverage them, and how to break someone else’s network effect. Finally, Casey shares his contrarian approach to interviewing product managers and his thoughts on the future of PM roles with AI. — Brought to you by Amplitude—Build better products | Eppo—Run reliable, impactful experiments | Ahrefs—Improve your website’s SEO for free Find the full transcript at: https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey Where to find Casey Winters: • Twitter: https://twitter.com/onecaseman • LinkedIn: https://www.linkedin.com/in/caseywinters/ • Blog: https://caseyaccidental.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Casey’s background (03:36) What Casey is up to (05:24) Why the CPO position is frequently short-lived (07:26) What Casey learned in his role as CPO of Eventbrite (10:15) The “zero interest rate phenomenon” product manager (12:17) Advice for thinking outside common frameworks (18:35) When to bring in research (21:16) What Whatnot does (21:59) Casey’s approach to interviewing PMs (23:29) Red flags in interview responses (24:27) The future of product management with AI (27:47) Founder intuition vs. team expertise (37:17) Adding the delivery driver app at Grubhub (40:00) Network effects (43:10) Why Zillow is a sticky product (44:05) How Grubhub’s network effect got taken over by DoorDash and Uber Eats (51:47) Don’t underestimate the competition (54:43) SaaS adding marketplace and vice versa (01:02:30) Defining marketplaces (1:05:43) Tips for B2C subscription startups (1:13:15) Lightning round Referenced: • Casey Winters on Lenny’s Podcast previously: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/ • Whatnot: https://www.whatnot.com/ • The 700-calorie breakfast you should eat if you want to live forever, according to futurist Ray Kurzweil: https://www.businessinsider.com/what-ray-kurzweil-eats-to-live-forever-2016-4 • The Way of the Gun on Hulu: https://www.hulu.com/movie/the-way-of-the-gun-0fc9590c-3f85-48ab-96e9-1da1b9695065 • Notion AI: https://www.notion.so/product/ai • Zapier: https://zapier.com/ • Founder intuition vs. team expertise vs. customer expertise: https://caseyaccidental.com/founder-intuition-team-expertise/ • Erika Warren on LinkedIn: https://www.linkedin.com/in/erika-warren/ • Alyssa Ravasio (Hipcamp) on LinkedIn: https://www.linkedin.com/in/alyssa-ravasio-23114717/ • Marketplace supply strategy: comprehensive, exclusive, or curated: https://a16z.com/2021/03/31/marketplace-supply-strategy/ • Nassim Taleb on Twitter: https://twitter.com/nntaleb • The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244 • OpenTable: https://www.opentable.com/ • Booking.com: https://www.booking.com/ • Faire: https://www.faire.com/ • How to increase your retention: https://www.lennysnewsletter.com/p/how-to-increase-your-retention-issue • The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951 • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/r • Profit from the Core: A Return to Growth in Turbulent Times: https://www.amazon.com/Profit-Core-Return-Growth-Turbulent/dp/1422131114/ • Party Down on Starz: https://www.starz.com/us/en/series/party-down/2011 • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • Station Eleven on HBO Max: https://www.hbomax.com/series/urn:hbo:series:GYZWoOQ6F9cLDCAEAAABP • Kicking and Screaming on Netflix: https://www.netflix.com/title/70052286 • Raven by Kelela on Spotify: https://open.spotify.com/album/06uhdSmIYrWRkdnAPjcRcT • Optical Delusion by Orbital on Spotify: https://open.spotify.com/album/2jQbFspnSh7erex6RDKQGJ • Stakes Is High by De La Soul on Spotify: https://open.spotify.com/album/3jlC2uhYNrhikZXLviEnpu Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Casey Winters discusses the unrealistic expectations placed on new product managers, who often act as if they have infinite resources and time. He reflects on the risk-averse culture that has developed, where the focus on following frameworks stifles innovation and creativity. Casey emphasizes the importance of using frameworks as tools rather than strict guidelines.
"every new person in the product team is acting like they work at Google and have these infinite resources in infinite time to make sure everything is perfect and there became such this focus on the ri..."
In this segment, Lenny welcomes Casey Winters back to the podcast, highlighting his impressive background in product management and growth across various companies. They discuss Casey's recent transition from Chief Product Officer at Eventbrite to advising startups, setting the stage for a deep dive into product management insights.
"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 gues..."
Casey shares his experiences as a Chief Product Officer, discussing the inherent challenges of the role and the difficulty in maintaining product-market fit over time. He reflects on the pressures faced by CPOs and the reality that few can claim to be 'crushing it' in such a demanding position.
"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 un..."
In this segment, Casey offers valuable advice for current and aspiring Chief Product Officers. He emphasizes the importance of understanding the broader business context and the need to balance product priorities with overall company goals. Casey also discusses the significance of diagnosing team strengths and weaknesses to drive product success.
"Casey welcome back to the podcast thanks Lenny great to be here you're the first ever returned guest to my podcast how does that feel I feel honored perhaps a bit unworthy but you know I'll go with it..."
Casey introduces the concept of the 'zero interest rate phenomenon' in product management, describing how many PMs today are overly reliant on research and data before making decisions. He contrasts this with the need for product managers to take risks and ship products to learn, highlighting a shift in mindset that has occurred in the industry.
"listening I'm like yeah I always love seeing how I can help companies right so everyone should err on the side reaching out and seeing if I have time to help if there's something they think I can help..."
Continuing the discussion on the zero interest rate phenomenon, Casey stresses the importance of shipping products to gain insights rather than waiting for perfect data. He critiques the tendency of product managers to overanalyze and emphasizes that sometimes the best way to learn is through action, not just research.
"a company for a long time yeah the needs 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 kn..."
Casey reflects on the unique challenges faced by product managers in startups, where resources are limited and decisions must be made under uncertainty. He shares insights from his experience at Eventbrite and how the pandemic forced the company to adapt quickly, highlighting the need for creativity and intuition in product management.
"first and a product exact second so I think some mistakes I made you know early that I I corrected successfully is you want to show that you are caring and paying attention to the overall business fir..."
In this segment, Casey discusses his approach to interviewing product managers, particularly in startup environments. He emphasizes the need for candidates to demonstrate creativity and problem-solving skills, rather than relying solely on data and established processes. Casey shares his perspective on what makes a successful product manager in today's landscape.
"I think products such a confusing uh discipline for people who aren't in it like a sales leader many CEOs you know marketing leader that they don't necessarily know what great looks like and the thing..."
Casey Winters shares insights from his experience interviewing product managers at startups like Whatnot. He discusses the unique challenges faced by PMs in early-stage companies, emphasizing the need for versatility and decision-making under uncertainty. He contrasts this with the expectations of PMs in larger organizations, highlighting how many candidates are ill-prepared for the realities of startup life.
"partially missed the mark and what's really going on 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 do..."
Winters explains the 'zero interest rate phenomenon' in product management, where abundant funding leads startups to operate like public companies. He discusses the implications of this phenomenon, particularly how it can create a false sense of security and preparedness among PMs, which may not hold up in times of financial strain.
"like Eventbrite so 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 ..."
Casey advises product managers to focus on adding value to customers rather than strictly following frameworks. He shares his experience at Eventbrite, where he encouraged a design team to prioritize shipping products and getting feedback, emphasizing the importance of creativity and intuition in product management.
"concrete thing that changes 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 probabl..."
Winters discusses the strategic use of research in product management, particularly in B2B versus consumer contexts. He outlines when it makes sense to invest in research, emphasizing the need for nuanced understanding of customer sophistication and the importance of direct feedback in shaping product decisions.
"that come to mind to that question 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 y..."
In this segment, Casey elaborates on identifying high-leverage areas for research within a company. He stresses the importance of focusing research efforts on significant problems that are not well-defined, ensuring that resources are allocated effectively to drive impactful solutions.
"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 so..."
Casey shares his contrarian approach to interviewing product managers, focusing on real scenarios rather than rehearsed answers. He emphasizes the importance of assessing candidates' ability to think critically and creatively about the role, rather than relying on their past experiences.
"have that they're selling and people who are watching the stream can't engage with the sellers and bid on you know different items so kind of like twitch meets eBay also they describe it awesome and I..."
Winters identifies key red flags to watch for during PM interviews, such as candidates who rely heavily on data and research before making decisions. He discusses the importance of assessing a candidate's ability to think holistically and factor in time constraints when proposing solutions.
"there like red flags you look for in these interviews like one is maybe set over like I can't even begin to answer this without research and data is there anything else some things I pay attention to ..."
Casey discusses the impact of AI on product management roles, arguing that while some aspects may be automated, the core responsibilities of PMs—such as decision-making and subject matter expertise—are less likely to be replaced. He cautions against over-reliance on AI tools, emphasizing the need for critical thinking.
"how much do you think they're intimidated by being interviewed by Casey Winters how much do you think that factors in I think you overestimate my importance or awareness in the community I think most ..."
In this segment, Casey shares practical ways PMs can leverage AI tools to enhance their productivity, particularly for tedious tasks. He highlights the potential of AI to assist with problem-solving and data management, while also cautioning against its limitations and inaccuracies.
"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 yep it's a tool that's trained on sounding smart rather than always necessarily being sm..."
Casey explores the balance between founder intuition and team expertise in decision-making. He discusses how founders can leverage their unique insights while also integrating team input, particularly as companies grow and evolve. This segment highlights the dynamic nature of leadership in startups.
"there's something on Google Docs that I need to figure out how to do that was kind of fancy I asked chat gbt it told me how to do it and I was like oh great I had a similar experience but I just neede..."
In this segment, Casey discusses the balance between founder intuition and team expertise in startups. He explains how founders often have deep, subconscious knowledge of their business that new hires may not possess. Casey emphasizes the importance of founders guiding their teams until they demonstrate they can make better decisions.
"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 and tuition should overrule say team expertise and how that changes..."
Casey elaborates on the dynamics between founders and their teams, highlighting the need for founders to remain involved in decision-making until their team members prove their capabilities. He shares a personal anecdote about hiring a leader at GrubHub and the importance of situational leadership in fostering team success.
"signals where their founder intuition has been usurped by team expertise or maybe it's just ebbed in Effectiveness over time and and that of course makes sense right Founders have all these different ..."
This segment explores how the relevance of founder expertise diminishes over time as companies scale. Casey discusses how founders must adapt to changing dynamics and delegate responsibilities while ensuring they remain attuned to their customers' needs. He emphasizes the importance of communication between founders and employees to signal when expertise shifts.
"stay deep in anymore so I I built this you know chart on um or I guess I should say table on the different phases of you know a startup right and when you're you're finding product Market sit like eve..."
Casey provides advice for employees on how to effectively communicate their ideas to founders who may be resistant to change. He stresses the importance of understanding the founder's perspective and suggests using data, external validation, or experiments to build a compelling case for new initiatives.
"thought they needed to make these decisions and they were still the ones that knew everything yep that makes me think about most companies maybe not most but many Founders just like believe they have ..."
Reflecting on his time at GrubHub, Casey shares a story about a decision regarding a delivery driver app that he initially opposed. He acknowledges the founders' foresight in pushing for the app's development, which ultimately became essential for competing with newer delivery services. This highlights the importance of long-term thinking in leadership.
"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..."
Casey introduces the concept of network effects, explaining how products become more valuable as more users join. He outlines three types of network effects: direct, cross-site, and data network effects, using examples from platforms like WhatsApp and GrubHub to illustrate how these dynamics operate in practice.
"it it's probably the right way to do it whether I'm correct or not it is a role I sometimes play in the ecosystem I will admit there's an example where you were convinced something was the right way t..."
Casey Winters explains the concept of network effects, emphasizing how a product or business improves as more users engage with it. He categorizes network effects into three types: direct, cross-site, and data network effects, providing examples like WhatsApp and GrubHub to illustrate each type's significance in enhancing user value.
"I was excited to chat about is around Network effects and marketplaces and SAS and kind of how those things connect I feel like you have the clearest way of thinking about and explaining Network effec..."
Winters discusses the necessity for businesses, particularly social networks and marketplaces, to evolve their network effects over time. He highlights that while direct network effects are common, successful companies often integrate cross-site and data network effects to enhance their value proposition and defensibility against competitors.
"and then there are cross-site 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 th..."
Casey shares insights on Zillow's unique strategy in the real estate market, explaining how it connects buyers and sellers through real-time pricing information. This innovation creates a stickier product by enhancing the user experience for both sides of the marketplace, showcasing how effective network effects can lead to greater user engagement.
"I love that though 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..."
Winters analyzes how GrubHub's asset-light model faced disruption from competitors like DoorDash and Postmates, which adopted a heavily managed marketplace approach. He discusses the challenges GrubHub encountered as these new entrants expanded their restaurant selection, ultimately leading to a shift in market dynamics and user preferences.
"we've been talking about GrubHub a lot and GrubHub had some pretty strong Network effects and yep and large part thanks to the work you did and one of the benefits of network FX is it creates a barrie..."
Reflecting on GrubHub's market position, Casey emphasizes the importance of recognizing and responding to disruptive competitors. He discusses the strategic missteps GrubHub made, including underestimating the potential of negative margin competitors and the need for aggressive adaptation in the face of existential threats.
"first two that Rose to prominence ubereats 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 ma..."
Winters draws parallels between GrubHub's experience and the innovator's dilemma, highlighting how established companies can overlook disruptive innovations that initially seem inefficient. He stresses the need for businesses to adapt quickly to changing market conditions and to recognize the potential of new business models that may disrupt their existing operations.
"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..."
In this segment, Casey discusses the challenges startups face when competing against established giants like DoorDash and Uber. He emphasizes the need for innovative strategies that leverage unique market angles, especially in a climate where funding is less accessible, and traditional competitive tactics may no longer suffice.
"you know it's essentially when everyone's find like a more efficient Network effect for demand on the on the marketplace side you probably need to copy that like as soon as possible and if you can't c..."
Casey explores the trend of integrating SaaS tools into marketplace models and vice versa. He critiques the effectiveness of such strategies, using OpenTable as a case study to illustrate the challenges and potential pitfalls of merging these business models, ultimately questioning their long-term viability in the market.
"perfect segue to my next question I only have a couple more there's this uh concept and I think poll from Marketplace Founders to add a SAS tool eventually and have both business models and then there..."
Casey shares insights from his experience at Eventbrite, detailing how the company started with a SaaS-like approach and is now layering in marketplace elements to drive ticket sales. He emphasizes the importance of achieving cross-side network effects for growth.
"think what people misunderstand about restaurants historical these restaurants are these incredibly low margin businesses and it's like yeah they are because they're paying the rent no matter what hap..."
In this segment, Casey discusses Fair, a company he advises, which successfully built a wholesale marketplace before adding SaaS tools. He highlights how this approach has enabled Fair to grow quickly by onboarding independent retailers.
"got it okay great so keep going so that's open table so look this is definitely the strategy we are working on with Eventbrite where we started with something that was more sas-like you know enabling ..."
Casey argues that marketplaces adding SaaS tools generally have a better chance of success compared to SaaS businesses trying to add marketplaces. He explains the challenges and skills required for each model, emphasizing the importance of customer relationships.
"obviously something we're working on um fair is a company I advise more recently that I think is unlocked this model in like the reverse where there is a wholesale Marketplace between independent reta..."
Casey elaborates on the inherent difficulties of building marketplaces, noting that starting with a marketplace model can be more advantageous. He discusses the need for a strong customer base and the challenges of scaling in a competitive environment.
"um whereas you know marketplaces that add a SAS component you know it's a customer acquisition tool like there or a workflow or retention tool to you know increase retention or reduce disintermediatio..."
In this segment, Casey defines what constitutes a marketplace, emphasizing the importance of driving demand to supply. He contrasts marketplaces with tools that merely facilitate transactions without creating cross-side network effects.
"couple things of a couple attributes that kind of tell you that maybe it might work maybe just share those again real quick so take square or sub stack or patreon or like Eventbrite right right all of..."
Casey discusses the evolution of platforms like Patreon and Substack, highlighting the challenges they faced in becoming marketplaces. He notes how Substack has successfully created a network effect, allowing users to discover relevant content.
"yeah there's and then there's of course the marketplaces that win with like standardization of like I can get it at any time it might be from different people but I know the Uber car is going to be th..."
Casey praises Substack's innovative features that facilitate user discovery and engagement. He reflects on how these features have contributed to Substack's growth and the potential for new players to leverage similar strategies.
"what this makes me think about is patreon and sub stack and interestingly when I was looking at early patreon days what I understand is they want it to be a Marketplace they wanted to be a place where..."
Casey shares insights on the challenges of building consumer subscription businesses compared to B2B SaaS. He discusses the unpredictability of consumer behavior and the importance of high retention rates for success.
"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 eighty percent of my new sign ups are coming from sub Stacks..."
In this segment, Casey explains why B2B SaaS businesses are favored by investors due to their predictable revenue and net dollar retention. He contrasts this with the challenges faced by consumer subscription models.
"know there's a lot of happy talk out there a lot of posts here's how you do this sure and sometimes you can't I think in order to understand these businesses you have to start with why do investors li..."
Casey highlights successful consumer subscription companies like Netflix and Spotify, discussing their unique strategies for retention and growth. He emphasizes the importance of economies of scale and network effects in achieving success.
"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 one of these players that's making it wo..."
Casey highlights the critical nature of user retention in subscription businesses, explaining how high churn rates can necessitate constant user acquisition. He shares insights on how companies like Spotify and Netflix manage to retain users despite high operational costs, and discusses the implications for startups aiming to achieve similar success.
"eventually it'll be no longer profitable and what network effects allow you to do is they allow your product to get better or faster than the customers you target get worse normally through increased ..."
In this segment, Casey discusses the trend of B2C subscription companies pivoting to B2B models. He shares insights from his interviews with founders of early B2C apps, emphasizing the importance of efficiency and adaptability in navigating market changes. This segment provides valuable lessons for entrepreneurs considering their business model strategies.
"and this is also why a lot of these companies pivot to B2B they realize uh there's they're not going to get anywhere with b2c the other lesson I took away because I interviewed a lot of these early b2..."
Casey shares his approach to fostering collaboration within cross-functional teams in product development. He introduces the concept of designating a 'driver' for projects, which empowers team members to make decisions and streamline the execution process. This segment offers practical advice for improving team dynamics and project outcomes.
"have time to figure out how to like grow again but if that increases your Burn by like 100 million dollars you have a lot more of a panic on your hands so maybe just to tie the loop tie the knot close..."
In the lightning round, Casey shares his top book recommendations, including 'The Goal' by Eliyahu M. Goldratt and 'Thinking, Fast and Slow' by Daniel Kahneman. He also discusses his favorite recent TV shows and movies, providing a glimpse into his personal interests and influences. This segment is a light-hearted conclusion to the discussion, showcasing Casey's diverse tastes.
"years from now 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 definitely the goal by Elijah ..."