The Exchanges

Q I do want to move into my favorite element though, chaps, in terms of the quick fire round. So I say a short statement. You give me your immediate thoughts. Finn, you're a master at this already. Todd, this will be great fun, and I'm going to start with you, Todd. I promised myself I would read more in twenty-twenty. Help me out here. What's the favorite book and why?

A All right, so I'll give you two books that I actually heard on this podcast, so kudos to you, Harry, for sourcing some great reads. The first one is Creative Selection. It's a story of how the design process Work internally at Apple during the age of the iPod, the iPhone, and the iPad. And I'm just definitely a sucker for any book that talks about the internals or the secret sauce of a great company like Apple. And the second is Trillion Dollar Coach by Eric Schmidt and Jonathan Rosenberg. And I just loved it because there's so much gold in there about how to be a great leader of people. And also because it gave me this window into the very early days of Google before I got there.

AI assessment note: “The first one is Creative Selection.”

Q products that you've worked on from, as you said, Google Mail there to To two hundred million, now in a billion, Facebook newsfeed, the Dropbox, and Twitter. My question to you was, in terms of the learning, if you were to choose, say, two or three of your biggest takeaways from working at these incredible product companies, what would they be, and how do you think they impacted your mindset?

A So there were so many, but I'll highlight three big takeaways. One on products, one on business model, and one on culture. So on products, you know, it was really interesting to see how Google approached product development from the inside. We were all about products that were simple, fast, It's useful. And the interesting part was what it took behind the scenes in order to get that. So for example, you know, I mentioned I was on Marissa Meyer's APM team, and she used to run this very rigorous process called consumer UI review, where you would bring your early product designs in front of this panel of senior designers. You'd project them up on this big screen, and then they would critique them. And then you go back to your desk and improve them. And this created an environment where all the details were scrutinized and everything was in service of making the UI as intuitive as possible. And Gmail was the same way. You know, we were totally obsessed with making an email experience that was powerful and simple and always fast. So there were features we'd refine over and over before releasing them, and our bar was just incredibly high. And I remember one time we had gone through this big redesign of the label system in Gmail, and we were about to launch it. And actually the night before launch, we held it back because we realized we had unintentionally added about 30 milliseconds …

AI assessment note: “I'll highlight three big takeaways. One on products, one on business model”

Q products that you've worked on from, as you said, Google Mail there to To two hundred million, now in a billion, Facebook newsfeed, the Dropbox, and Twitter. My question to you was, in terms of the learning, if you were to choose, say, two or three of your biggest takeaways from working at these incredible product companies, what would they be, and how do you think they impacted your mindset?

A So there were so many, but I'll highlight three big takeaways. One on products, one on business model, and one on culture. So on products, you know, it was really interesting to see how Google approached product development from the inside. We were all about products that were simple, fast, It's useful. And the interesting part was what it took behind the scenes in order to get that. So for example, you know, I mentioned I was on Marissa Meyer's APM team, and she used to run this very rigorous process called consumer UI review, where you would bring your early product designs in front of this panel of senior designers. You'd project them up on this big screen, and then they would critique them. And then you go back to your desk and improve them. And this created an environment where all the details were scrutinized and everything was in service of making the UI as intuitive as possible. And Gmail was the same way. You know, we were totally obsessed with making an email experience that was powerful and simple and always fast. So there were features we'd refine over and over before releasing them, and our bar was just incredibly high. And I remember one time we had gone through this big redesign of the label system in Gmail, and we were about to launch it. And actually the night before launch, we held it back because we realized we had unintentionally added about 30 milliseconds …

AI assessment note: “I'll highlight three big takeaways. One on products, one on business model, and one on culture.”

Q so well there, Finn. So again, I'm flunking the schedule, but I'm a massive product market Fit nerd. I'm obviously a huge believer in a lot of what Rahul at Superhumans proclaimed and provisioned with a lot of his work. Todd, what are your thoughts on product market fit today? How founders assess it, your experience with it, when you know you have it, how do you think about that?

A Yeah, so I think it's probably a good time to talk about my startup, which was called Cover in 2013, and we thought a lot about this at the beginning. And honestly, when you talk about finding product market fit, in my opinion, the most important choice you make As a founder is picking a good market. And other than choosing your co-founders, I actually think that that's the single most important choice that a founder makes. And so Josh Koppelman refers to this as the pick. And so I'll share the framework that I recommend that founders use, which is the one that we use to cover. So number one, does the idea or the product address a clear functional need that users have? And that's often why they will try the product. But does it also address an emotional need that users have? And that's often why they'll tell others about the product. Is it in a large, underserved market, or is it in a market that can become large? And not always necessary, but helpful. Is there something just kind of novel or unique about the user experience? Does it feel a little bit like magic the first time you use it? And so really quickly, I'll just run through how we experienced this at Cover. On the market, Cover was an Android-focused company, and Android was just a terrific market for us to focus on. It was massive. I think at the time, there were like three times the number of Android users to iPhone …

AI assessment note: “I'll share the framework that I recommend that founders use”

Q mean, Todd, that is Such amazing news. Huge congratulations. Before we dive in, I guess, I would love, though, to kind of hit on a little bit of your background. As Finn mentioned there, the incredible product experience that you've had, but how did you make your way into the world of venture then, as of, you know, the news today, and come to be a partner at first round?

A Yeah, so I started my career in Silicon Valley at Google in 2004 as an associate product manager. I think I was actually in the second class ever of Google APMs, and I shared this tiny office with my boss, Marissa Meyer, at the And I worked on Gmail for five years and it had just launched in beta when I joined. So these were four of the days of G suite before anyone was really using Gmail for work in a serious way. And we grew Gmail to over two hundred million users during my time there. And now I think it's well over a billion, which is just mind boggling to me. And then I went to Facebook in 2011 because I wanted to experience a different culture and I wanted to work on a social product. And so at Facebook, I worked on photos, groups, and this big redesign that we did of newsfeed. And then ultimately I wanted to be a founder. So I left Facebook to start my own company in 2013, which was called cover. And first round was our lead investor. Josh Koppelman was our board member. So that's when I first got to work with first round and cover was a custom lock screen for Android phones. So we were one of the first companies in Silicon Valley to really focus a hundred percent on Android when most other companies were treating it as this afterthought. And so at cover, I got the experience starting something from scratch, finding product market fit, We grew to over two million users in…

AI assessment note: “first round was our lead investor. Josh Koppelman was our board member.”

Q journey with cover and short journey though. I want to ask in terms of how you think that impacts you as an investor, Todd, having raised for your own startup being covered in the last seven years or so, how do you think that informs maybe the founder experience and the type of investor experience that you would like to deliver to founders now as a partner at first round?

A Yeah. So in our seed fundraising process for cover, we actually talked to over Angel investors, seed funds, all the big Sand Hill Road firms, and we actually met First Round and Josh Koppelman towards the very end of that process, so we had developed a good sense of what the other VCs were like, and immediately we knew that First Round was the right firm for us. And so kind of drawing from that experience, here's what I hope to personally deliver to founders as an investor. First off, just as a former founder myself, I went through fundraising. I went through the early days of finding product market fit. Growing organically to millions of users and ultimately through this successful acquisition. And I leaned so much on Josh during the most critical pieces of that journey. And so I just have a good recent feel for how investors can and should be helpful to founders. You know, but I've also had other experiences of scaling as an executive through an IPO and managing big teams of people across product design and analytics. So I know how to run large teams and I want to help founders evolve from the very early days of just these two people sitting in a room together all the way through to being a world-class CEO running a thousand person company. And I've already spent a lot of time over the past couple of years advising founders and angel investing, and as a way of seeing what it'…

AI assessment note: “drawing from that experience, here's what I hope to personally deliver to founders”

Q Todd, you sold your startup to Twitter. If the time came again, would you do it again, and what's the reasoning?

A Yeah, so the biggest thing that I reflected on a lot in the years afterwards, and that I would say I'm not still a hundred percent sure of, were should we have sold and should we have sold to Twitter versus Dropbox or one of the other companies that we were talking to. And I think in retrospect, we made the best decision we could with the information we had at the time. We ran a really good process. We sort of ran it like a fundraising process where we had multiple companies that we were talking to, and so that allowed us to really control the timeline and get a great outcome on the acquisition. If I'm honest, certainly Twitter was a bit of a rough ride in 2014 and 20 15, and the stock price on the day I left was lower than the day I started, and a lot of the acquisition was based on stock. But at the end of the day, it was a really good learning experience, and I'm glad it's in my history so that I have some first-hand knowledge to coach founders with today as they go and think about acquisitions potentially. We worked on some really interesting projects at a very interesting time in Twitter's history, and some amazing people who I still work with today, and we all did fine financially. So I think the best decision is the one we made at the time, given what we knew, and I'd probably make that decision again today.

AI assessment note: “I'd probably make that decision again today.”

Q Can I ask Tom, what does it take to be a great coach to founders, do you think?

A I think that one of the traps that I fell into very early on as an angel investor was trying to solve all of the founders' problems myself. And trying to help them come up with the perfect answers, especially if it was something product related. Product ideas just kind of naturally come to me, and it's something that I'm excited to talk about, but I learned over the course of working with many founders that it's better to be in a listening mode, helping the founder themselves, like, deeply understand the problem and the different approaches they might take to thinking through the problem, rather than trying to answer the question yourself. And I think that's probably something a lot of Former operators and especially a lot of former product people kind of have to learn the hard way as, as they learn to become great investors and great coaches.

AI assessment note: “better to be in a listening mode, helping the founder themselves, like, deeply understand”

Q journey with cover and short journey though. I want to ask in terms of how you think that impacts you as an investor, Todd, having raised for your own startup being covered in the last seven years or so, how do you think that informs maybe the founder experience and the type of investor experience that you would like to deliver to founders now as a partner at first round?

A Yeah. So in our seed fundraising process for cover, we actually talked to over Angel investors, seed funds, all the big Sand Hill Road firms, and we actually met First Round and Josh Koppelman towards the very end of that process, so we had developed a good sense of what the other VCs were like, and immediately we knew that First Round was the right firm for us. And so kind of drawing from that experience, here's what I hope to personally deliver to founders as an investor. First off, just as a former founder myself, I went through fundraising. I went through the early days of finding product market fit. Growing organically to millions of users and ultimately through this successful acquisition. And I leaned so much on Josh during the most critical pieces of that journey. And so I just have a good recent feel for how investors can and should be helpful to founders. You know, but I've also had other experiences of scaling as an executive through an IPO and managing big teams of people across product design and analytics. So I know how to run large teams and I want to help founders evolve from the very early days of just these two people sitting in a room together all the way through to being a world-class CEO running a thousand person company. And I've already spent a lot of time over the past couple of years advising founders and angel investing, and as a way of seeing what it'…

AI assessment note: “drawing from that experience, here's what I hope to personally deliver to founders”

Q Can I ask Tom, what does it take to be a great coach to founders, do you think?

A I think that one of the traps that I fell into very early on as an angel investor was trying to solve all of the founders' problems myself. And trying to help them come up with the perfect answers, especially if it was something product related. Product ideas just kind of naturally come to me, and it's something that I'm excited to talk about, but I learned over the course of working with many founders that it's better to be in a listening mode, helping the founder themselves, like, deeply understand the problem and the different approaches they might take to thinking through the problem, rather than trying to answer the question yourself. And I think that's probably something a lot of Former operators and especially a lot of former product people kind of have to learn the hard way as, as they learn to become great investors and great coaches.

AI assessment note: “better to be in a listening mode, helping the founder themselves, like, deeply understand”

Q Todd, you sold your startup to Twitter. If the time came again, would you do it again, and what's the reasoning?

A Yeah, so the biggest thing that I reflected on a lot in the years afterwards, and that I would say I'm not still a hundred percent sure of, were should we have sold and should we have sold to Twitter versus Dropbox or one of the other companies that we were talking to. And I think in retrospect, we made the best decision we could with the information we had at the time. We ran a really good process. We sort of ran it like a fundraising process where we had multiple companies that we were talking to, and so that allowed us to really control the timeline and get a great outcome on the acquisition. If I'm honest, certainly Twitter was a bit of a rough ride in 2014 and 20 15, and the stock price on the day I left was lower than the day I started, and a lot of the acquisition was based on stock. But at the end of the day, it was a really good learning experience, and I'm glad it's in my history so that I have some first-hand knowledge to coach founders with today as they go and think about acquisitions potentially. We worked on some really interesting projects at a very interesting time in Twitter's history, and some amazing people who I still work with today, and we all did fine financially. So I think the best decision is the one we made at the time, given what we knew, and I'd probably make that decision again today.

AI assessment note: “I'd probably make that decision again today.”

Q from your angel checks and also from Katie Stanton most recently, but I wanted to ask, because when we had Josh Koppelman, your now partner on the show, he said he became more conservative when he made the move to institutional investing from angel investing. I'm really interested. How do you think your mindset will shift with the change from previously being angel to now first round and institutional investing?

A Yeah. So the biggest reason that I wanted to join a fund instead of starting my own fund or instead of staying as an angel is that I really wanted partners. And I've gotten to see a lot of my friends who are great investors. Katie Stanton, like you mentioned, love, love the episode with her, by the way, Ben Ling, Brianne Kimmel start their own funds as solo GPs. And I'm actually an LP in those funds. So I've gotten to see how they've approached it up close. And I have massive respect for them starting brand new funds on their own. But for me personally, I just wanted something different. I wanted partners who were five to 10 years ahead of me in their investing careers and that I could learn from. Because at every point in my career, when I reflect, when I've developed the most, when I learned the most every day was when I had a great mentor. And I think this is especially true in seed investing, where it can take like five to seven years to know whether an investment was a good one or not. And so here's how I thought about it. How will the first round partnership make me better? And the answer is that I'll be bringing the same mindset that I've had and been honing as an angel and an advisor for these past five years. But But that mindset, I hope, is going to evolve rapidly and be accelerated by spending all this time with Haley and Bill and Finn and Josh. And I'll see more com…

AI assessment note: “I'll be bringing the same mindset... But that mindset, I hope, is going to evolve”

Q so well there, Finn. So again, I'm flunking the schedule, but I'm a massive product market Fit nerd. I'm obviously a huge believer in a lot of what Rahul at Superhumans proclaimed and provisioned with a lot of his work. Todd, what are your thoughts on product market fit today? How founders assess it, your experience with it, when you know you have it, how do you think about that?

A Yeah, so I think it's probably a good time to talk about my startup, which was called Cover in 2013, and we thought a lot about this at the beginning. And honestly, when you talk about finding product market fit, in my opinion, the most important choice you make As a founder is picking a good market. And other than choosing your co-founders, I actually think that that's the single most important choice that a founder makes. And so Josh Koppelman refers to this as the pick. And so I'll share the framework that I recommend that founders use, which is the one that we use to cover. So number one, does the idea or the product address a clear functional need that users have? And that's often why they will try the product. But does it also address an emotional need that users have? And that's often why they'll tell others about the product. Is it in a large, underserved market, or is it in a market that can become large? And not always necessary, but helpful. Is there something just kind of novel or unique about the user experience? Does it feel a little bit like magic the first time you use it? And so really quickly, I'll just run through how we experienced this at Cover. On the market, Cover was an Android-focused company, and Android was just a terrific market for us to focus on. It was massive. I think at the time, there were like three times the number of Android users to iPhone …

AI assessment note: “the framework that I recommend that founders use, which is the one that we use”

Q mean, Todd, that is Such amazing news. Huge congratulations. Before we dive in, I guess, I would love, though, to kind of hit on a little bit of your background. As Finn mentioned there, the incredible product experience that you've had, but how did you make your way into the world of venture then, as of, you know, the news today, and come to be a partner at first round?

A Yeah, so I started my career in Silicon Valley at Google in 2004 as an associate product manager. I think I was actually in the second class ever of Google APMs, and I shared this tiny office with my boss, Marissa Meyer, at the And I worked on Gmail for five years and it had just launched in beta when I joined. So these were four of the days of G suite before anyone was really using Gmail for work in a serious way. And we grew Gmail to over two hundred million users during my time there. And now I think it's well over a billion, which is just mind boggling to me. And then I went to Facebook in 2011 because I wanted to experience a different culture and I wanted to work on a social product. And so at Facebook, I worked on photos, groups, and this big redesign that we did of newsfeed. And then ultimately I wanted to be a founder. So I left Facebook to start my own company in 2013, which was called cover. And first round was our lead investor. Josh Koppelman was our board member. So that's when I first got to work with first round and cover was a custom lock screen for Android phones. So we were one of the first companies in Silicon Valley to really focus a hundred percent on Android when most other companies were treating it as this afterthought. And so at cover, I got the experience starting something from scratch, finding product market fit, We grew to over two million users in…

AI assessment note: “So that's when I first got to work with first round”

Q Now, Todd, I want to finish with you here, and this is a tough one given the recency of the announcement, but what's been your most recent personal or professional institutional investment, maybe, that's maybe publicly announced, and why did you say yes and get so excited?

A So I'll break the rules, Harry, and give you two. They're not the most recent, but they're the most top of mind for me because I've been working really deeply with them over the past year, and because they've also raised great follow-on funding rounds. First is Papaya Payments. It's founded by Patrick Kahn and Eric Meltzer. Papaya is this mobile payments app where you can take a photo of any paper bill, like a medical bill, a parking ticket, and they just pay it for you automatically. So it's, it's that very magical experience that we talked about earlier. And their seed round was led by first round, I think a few years ago, and they later raised their series A from Sequoia. And then Snackpass. So Snackpass is also a first round seed company. Snackpass started when the founders, Kevin Tan and Jamie Marshall, were actually undergrads at Yale. And they built this app that lets you order ahead at restaurants and skip the line. And it's also got a bunch of really cool social features like gifting and group discounts that make it spread virally on college campuses. And so they just raised a fantastic series A led by my friend Andrew Chan and Andreessen. And I love working with the Snackpass team. And it's also been really fun being in board meetings with Andrew.

AI assessment note: “So I'll break the rules, Harry, and give you two. They're not the most recent”

Q from your angel checks and also from Katie Stanton most recently, but I wanted to ask, because when we had Josh Koppelman, your now partner on the show, he said he became more conservative when he made the move to institutional investing from angel investing. I'm really interested. How do you think your mindset will shift with the change from previously being angel to now first round and institutional investing?

A Yeah. So the biggest reason that I wanted to join a fund instead of starting my own fund or instead of staying as an angel is that I really wanted partners. And I've gotten to see a lot of my friends who are great investors. Katie Stanton, like you mentioned, love, love the episode with her, by the way, Ben Ling, Brianne Kimmel start their own funds as solo GPs. And I'm actually an LP in those funds. So I've gotten to see how they've approached it up close. And I have massive respect for them starting brand new funds on their own. But for me personally, I just wanted something different. I wanted partners who were five to 10 years ahead of me in their investing careers and that I could learn from. Because at every point in my career, when I reflect, when I've developed the most, when I learned the most every day was when I had a great mentor. And I think this is especially true in seed investing, where it can take like five to seven years to know whether an investment was a good one or not. And so here's how I thought about it. How will the first round partnership make me better? And the answer is that I'll be bringing the same mindset that I've had and been honing as an angel and an advisor for these past five years. But But that mindset, I hope, is going to evolve rapidly and be accelerated by spending all this time with Haley and Bill and Finn and Josh. And I'll see more com…

AI assessment note: “bringing the same mindset that I've had... But that mindset, I hope, is going to evolve rapidly”