YouSaid · the spoken record

Casey Winters

lines on the record: 93
first: 2023-03-30
most recent: 2023-03-30
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“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 want to 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. Of course, that's going to happen. And those are some of the worst cases. But I think if you do state your point, you've actually built up the expertise, you're confident, and you are refuted for whatever reasons.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Correct, right? Everything was 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 growth channels as we have done.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 So I think it's really hard for founders to get those signals organically. And I think it's up to us as employees to help. And the founders can listen to the signals or not listen to those signals. But that's part of why we're here. But we should also give those signals when we're confident we really get it, not like come in day one being, I know what your sales strategy should be. You're doing it all wrong. Chances are the founders weren't doing it all wrong. They knew something you don't know about yet.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“And then when you start scaling the company, because you found product market fit, it's the first time that founders run into this classic problem of what got you here won't get you there, what got you to product market 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 framework originally is when I was at Grubhub, we were scaling pretty nicely and fairly organically. I think Mike and Matt, the founders, had intuited these phases of like building a company pretty well. But we acquired a competitor. And I saw how that company we acquired operated.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, but it means more breadth and less depth on any particular issue. And the reverse is true for the people you hire, right? They're able to get really deep into things that maybe you were really deep into two years ago, but you just can't stay deep in anymore. I felt this, you know, chart on, or I guess I should say table, on the different phases of a startup, right? And when you're finding product markets fit, like everything goes through the founders. You cannot outsource that.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, I mean, there's obviously the feedback loop of that of like, you know, what happens when you do either of those things? So depending on the founder's response to that or the employee's response to that, there's kind of different approaches you can take.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, this is not a founder example, but I remember when I hired Erica Warren to build out our loyalty program at Grepup. She now leads growth 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 just tell them. And this can, of course, change, like in the case of Erica, you know, if you hire the right people, 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, or maybe it's just ebbed in effectiveness over time.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“If founders are lucky slash good enough to find product markets 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 These people will come in with a lot of excitement, ideas, maybe even really relevant experience, especially senior leaders. And I've seen some founders 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 get. You actually need to direct them until they show you they've really got it and are making better decisions than you would.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I've had a couple of those things where it's like, hey, how do I actually get this weird thing done? And it's been like 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. So that's where my head goes to like more confidently use it. Because of course, I'll try it. And if it's wrong, I'll learn where it's wrong so that 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 need 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like it's just complete nonsense. It did have some stuff that did happen. It knew I worked at Eventbrite and it knew I worked at Pinterest and stuff. But like half of it was just completely made up. It sounded plausible, but it wasn't actually 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. You know, if you're not great at like seller 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 zappier 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 going to become a lot more than that but for a lot of these other use cases that people are touting there's a decent chance confidently tells you the wrong thing and that would scare me as a PM.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I was at Eventbrite the other day, and someone was telling me how they were loving the new notion AI integration. She asked me if I'd used it. I said, no, she's like, oh, you totally need to. Hey, go ask you 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 products, none of which happened.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think if you thought the PM job was just filling in the latest reforge or Shreyash framework and then getting that automatic fang promotion every year and a half. Then yeah, you're going to get replaced by AI. But I think the real PM job is the least likely to get replaced over time because you need real subject matter expertise. You need to be trading off a lot of different types of things and making good decisions for the company 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. It's a tool that's trained on sounding smart rather than always necessarily being smart.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Some things I pay attention to is if they're talking about solutions that are going to take a long time to get signal from. Whether it's months and months of engineering time before you actually see the impact on users or the business, I think that's always great if they're not factoring in the amount of time it will take in general is not 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”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm going to give you a real scenarios that I expect from the role. I want to 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel like the whole thing's gotten so performative. It's like interviewing is handing out Oscars based on who's prepared the best Tell Me About a time response. Versus actually assessing 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. But Benicio Del Toro says in it. It's like these days, they want to be criminals more than they want to commit crime. I think about that quote a lot when it comes to interviewing. So I would say I'm a bigotrion here in my approach. I don't ask about your work history. I don't care about your perfectly practiced answers.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, sure. So, Whatnot's a live streaming marketplace, mostly focus 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 different items. So kind of like Twitch meets eBay to describe it.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Internal feedback. So, you know, for EdPri, 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 going to be a scarce resource inside the company, which 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. 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 is going to at any way hit the mark.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“If you're super enterprise, it's kind of 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 pop to the customers and sales who knows the customer's 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 you're basically doing the research directly with the customer and with the sales team and translating that the things that are strategic to the business. And 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. There are maybe employees at companies or they're small businesses. And that's where you have to be more nuanced. 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?”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a consumer thing where the customers are rational. They're not experts. And that's generally where you just try things. Measure the impact they have, and you only really bring in your search research when the impact seems confusing, right? But you can run experiments like you can get data really easily. So bias towards getting stuff out there and seeing what us respond to.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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'd you 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 impact on our users. So those are some things that come to mind to that question.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I always advise going to companies where you can learn quickly and try things, right? And I think it's certainly okay to learn a bunch of frameworks. There's a reason I've invested a ton of time in RForge because I think it actually really does help people to see how other people have built things in a way that they can 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 the business. And 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 I know that he, you know, 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?”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“And that's going to go away over the next five years. 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 out now and make it work, you may run out of, you know, funding, right?”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“And also, I think zero interest rates allowed every startup to operate like it was a public company with billions of dollars.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“My follow up, which I don't ask, but what I really want to ask is, so when's the last time you used your brain versus followed a process someone else's design of your company? Because like I want the former, not the latter.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 or a public company, they'll 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 you start getting these weird responses in the interview process. 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. 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Or managers early in their career, because whatnot says startup. And 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 the PM to do at, you know, say a Google. But it all boils down to using your brain in different ways. Lisa, who's on our legal team, she called Eventbrite a public startup because the pandemic basically erased her business.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 heats for breakfast every morning to try to live longer. And the reporter estimated that cost him one million a year to have these habits. So 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 this profession. So I adopted this thing into like a public blog post that's on my blog now. But now that I've had some time outside of Eventbrite, I feel like I at least partially missed the mark on what's really going on. You see this with like whatnot because one of the things I'm helping them with is interviewing ICPMs again, which I haven't done in a while. And it's fascinating interviewing a PM.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Another thing I was noticing is I 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 most applicable for us. So it got me thinking like, okay, 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 frameworks on reforge. You know, I'm onboarding these UPMs. Like, is this my fault? But, you know, on reforge, we're building frameworks that are tools in a toolkit. We pull them out when relevant. They're not a coloring book, you know, to stay inside the lines of. So at one point, I got so fed up.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Really learn a shit. 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 extreme uncertainty and high leverage for getting to certain. 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 in the top unicorns did. They probably did a good job. And even if they didn't, all of our customers also use those products, so they're going to be familiar with us copying any approach that they've taken. So I think we sort of forgot in the industry that many times the fastest way to learn is to ship. So then, if you actually get them to skip research and just go look at competitors,”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, sure thing. So, this is something I started noticing while managing PMs and product designers at Eventbrite. And it's now coming up with whatnot as I hire, help them hire new PMs, is the environment in which a lot of product managers have come up 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 gained as a whole from that diversity of skills and previous experiences. So what I noticed is when we started doing product reviews out of Embright, if there was any sort of like uncertainty in a problem or a solution, the product manager, instead of like shipping to learn, would talk about all this research they have to do to really learn the problem.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is when you go public, you tend to rotate over your executive team and get public company execs versus startup execs. So 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 really helpful. But then it forces you to explain it. 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Really trying to diagnose without as much bias as possible where the strengths and weaknesses of your team, where the strengths and weaknesses of your product, lay that out with your peers and say, here's where we are, here's where I think we need to go. Here's the timeline on which I'm going to work to get us there because I think products such a confusing discipline for people who aren't in it, like a sales leader, many CEOs, 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. 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 going to get them to, but it's going to take some time. So one of the things we did at Eventbrite that I thought was really helpful.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“The first one I can think of is a big change from being a product leader to a CPO or something equivalent is you're actually a com exec first and a product exec second. So I think some mistakes I made early that I corrected successfully.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 worked out something where I continue to advise on the things that I'm uniquely good at 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 a really hard role, a really challenging role can be a lot of fun. And 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it's very hard to keep product martyr fit as a CPO within a company for a long time. 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, 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 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.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 out of Eventbrite, and they said, Congrats, you didn't get fired after two years. What's your secret?”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yook, I always love seeing how I can help companies, right? So everyone should error 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. Can't promise anything. But yeah, I just love talking to people about this stuff.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“Some still spending some time with whatnot and Eventbrite as advisors. I step 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 Beek, which is like Netflix for audio in Latin America. And I'm doing some Angel Investing in marketplaces and 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 build or maintain inside previous companies? The other thing I'm working on is revamping the product strategy program for ReForge. So I got some things keeping me busy, but definitely not as busy as I was last year.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 frameworks on reforge. I'm onboarding these UPMs. Like, is this my fault? But, you know, when ReForge, we're building frameworks that are tools in a toolkit. You pull them out when relevant. They're not a coloring book, you know, to stay inside the lines of.”
2023-03-30 · Lenny's Podcast · Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub) · IDENTIFIED FROM THE TRANSCRIPT · source