Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
www.lennysnewsletter.com
Popular Clips
Simply describing a product idea in words is not as compelling as seeing a testimonial from a user on top of a prototype or a mock and, like, really feeling the pain points. Is there an example that we could talk about? I know you can't talk about the product you're working on yet, but from the past of a vision that you crafted, maybe just share what the vision was or how you came to that to make this even more real. So, before I was working on, the new product, I was working on the FigJam team, and I was an early member of the FigJam team. And whiteboarding was sort of something that really took off during the pandemic because it was the first time that people were not together in office, couldn't, like, jam together, couldn't just, like, throw up a whiteboard behind them physically. And so there was kind of this question of like, okay, how do you combat these, like, disparate, teammates and pull them together into a common space? And I think that when we think about FigJam and what success might look like for FigJam, so a part of it that I was really invested in was the meetings experience. And specifically, like, what the world would look like if we were successful at bringing people together into a common space. And one of the early insights was, okay, what is, like, the most common meeting that takes place in a FigJam file? It's a brainstorm. Right? It's like you have a bunch of people, you've coming together, and they're, like, dropping a bunch of stickies and stuff like that. And so you have this, proof point of an activity that works really well inside of a FigJam file. But then at the same time, something that's really interesting about FigJam, people often ask, like, oh, you guys are Figma. Like, how do you guys use Figma as a company? And it's kind of interesting because I feel like we use Figma Figma the way that everyone uses Figma, but we use FigJam on steroids.
Seeing everything people apply to YC with, people all kinda have the same idea. One of these themes is simple pragmatic advice, sell shit, make money. One of my mantras is just don't die. Being coached and being reminded of the fundamentals and basics puts you in the right mindset. You have this concept of Tarpit ideas seems like an unsolved problem. You'll get all this positive feedback from the world, and people have been starting that startup since the nineties. Recently, you put out a request for startup 20 categories of ideas and the YC wants to fund. We're trying to mix up some of the information diet about what kind of ideas people might be contemplating they incur. A lot of people say you're the king of the pivot. A good pivot is like going home. It's warmer. It's closer to something that you're an expert at. Are there other patterns you find across startups that do well? There's a lot of founders that come this close to it all be it over and through sheer will kinda just keep it going. Today, my guest is Dalton Caldwell. Dalton is Managing Director and group partner at Y Combinator. Where he's worked for over 10 years across 21 different YC batches, including working closely in the earliest days of Instacart, retool, Brex, deal, DoorDash, Webflow, Replit, Amplitude, whatnot, Razorpay, and 20 other unicorns. Prior to white combinator, Dalton was the co founder and CEO of INEAM, which was acquired by Myspace and co founder and co of app.net, which was an early ads free competitor Twitter. Dalton has seen and worked with more startups than nearly any human alive. And in our conversation, we get incredibly tactical and deep on the startup journey. Why it all comes down to simply not losing hope and not letting your startup die? What to do when your startup struggling and how to know when it is time to give up what makes a great pivot and signs its time to pivot, had actually talked to customers, why every single startup goes through a point they feel like all hope is lost. Why investors say no to startups? What most often leads to startups failing? Why
We always say, hey. Please go look at our issue tracker. And if there's something you like, vote it up. If there's something you want to see change, leave a comment. And I think that's unique to GitLab. I think we've actually caused other organizations to do something similar because of that. And the other one is our direction and our strategy you mentioned earlier. Sometimes it's just a high level, like, paragraph, but sometimes if you go deeper, We have, like, a 1 year direction that is very detailed. It links over to our issue tracker to help you see, like, hey. We're going to do I don't know. We're gonna build widget x, and we're gonna do that in the next 6 months, and here's how we're going to do it. And I think those are those all those things together have really allowed Gillette to be the most transparent publicly traded company in the world. And we're very proud of that because it's just in our DNA to do it. Think what's really interesting about this is it's kind of the epitome of it's not the idea. It's the execution. You gotta share so many of the things that most people keep secret, and it's worked. I guess, is there any lessons there? Just like it's actually a lot. The execution is what separates you from everyone else. Someone could just basically copy everything you're doing in theory, build something like you built, but but they haven't. Yeah. I I think you're touching on actually my I when I interviewed in 2019, I actually asked Sid, our co founder and CEO, a similar question. I said, hey. I and I came from security in the GitHub. And I said, like, hey. We don't share more than 4 or 6 weeks with a road map with customers and even sales because we were in the situation where we didn't want our great idea to be taken and built before we built it. And then it happened to me at other places I've worked. And so what we in that conversation with him, he basically said, you know, it's products job to be ambitious instead of engineering's job to meet that ambition. And if you think of it that way, and it's that collaboration between the 2. It becomes less scary to put the information out. But you are right. We're very
So what you can change in order to get unstuck. If you're a founder or building a new product within a company and feeling like you're not making as much progress as you'd hope, You will find tremendous value in this conversation. With that, I bring you Todd Jackson after a short word from our sponsors. And if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube, it's the best way to avoid missing future episodes and it helps the podcast tremendously. This episode is brought to you by work OS. If you're building a SaaS app At some point, your customers will start asking for enterprise features, like SAML authentication and SCIM provisioning. That's where Work OS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand, that you can ship quickly and get back to building other features, and hundreds of other companies are already powered by Work OS, including ones you probably know, like Vericel, webflow, and Loom. Work OS also recently launched authkit, a complete authentication and user management service, It's essentially a modern alternative to auth 0, but with better pricing and more flexible APIs. OT kits design is stunning out of the box and you can also fully customize it to fit your app's brand. It's an effortless experience from your first user all the way to your largest enterprise customer. Best of all, off kit is free for any developer up to 1,000,000 users. Check it out at workos.com /lenny to learn more. That's workos.com/lenny. This episode is brought to you by Epo, Epo is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on EPO to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. An EPO helps you increase experimentation velocity while unlocking rigorous deep analysis
People often think that I get hired into later stage companies because I'm supposed to teach them how to operate like a big company. And if fact, I say I'm hired to remind them. They can operate like a startup. Everybody wants this. Everyone's like, yes. Move fast. Amazing quality. What's an example of that for you? I communicate to my leaders that my expectation is they bring in the clock speed 1 click faster. If you think something needs to be done this year, it needs to be done this there may be a trend happening here of combining engineering product. I'm using CPTO for short code of running product and engineering design functionally to other. There should be no debates over what's best for product or what's best for engineering, what's best for design should be. What is best for the organization? You built a tool called chat PRD. My guess is it's the single most popular AI PM specific tool out there. Is it gonna eliminate PMs next year? Probably not. Are the skills required gonna shift? Yes. Could these shift much faster than we all anticipate? Probably. Today, my guest is Claire Voe. Claire is a long time chief product officer at Color, Optimizely, and currently chief product officer at lunch, darkly. She's also been a 2 time founder, engineer, designer, and a marketer. She's also the creator of chat PRD, which I suspect is the most used PM specific AI product out there, which he builds on nights weekends. In our conversation, we dig into what PM skills AI complement and potentially replace in the future, the story behind chat PRD, and Claire's advice for how to stay ahead of the curve on AI, within the PM role, the importance of feeling agency over your career and how to bend the arc of the universe to achieve the things that you want to achieve, insights into what it takes to be a successful woman in tech, especially as an exec, how she creates a fast pace within larger companies, while also keeping the bar bear high, the rise of the CPT overall, combining product and engineering under 1 leader, plus a ton of career advice both for early career people and senior
