The Pomp Podcast - #559: Bobby Goodlatte on Bitcoin, Design, And Investing

Episode Date: May 19, 2021

Bobby Goodlatte is the co-founder and General Partner at Form Capital, an early stage venture capital firm focused on leveraging their design expertise. Previously, Bobby has made over 50 angel investments and was a former early designer at Facebook.  In this conversation, we discuss the importance of design, angel investing, hunting deals, rational vs irrational investors, Facebook, Coinbase, Form Capital, UX/UI in crypto, and Miami.  ======================= Circle is a global financial technology firm that enables businesses of all sizes to harness the power of stablecoins and public blockchains for payments, commerce and financial applications worldwide. Circle is also a principal developer of USD Coin (USDC), the fastest growing, fully reserved and regulated dollar stablecoin in the world. The free Circle Account and suite of platform API services bridge the gap between traditional payments and crypto for trading, DeFi, and NFT marketplaces. Create seamless, user-friendly, mainstream customer experiences with crypto-native infrastructure under the hood with Circle. Learn more at circle.com ======================= OKEx is a leading crypto exchange known for providing the most options for crypto traders and investors. Whether you want to trade spot, futures, options or swaps, OKEx gives you institutional-grade tools and a best-in-class trading engine. The platform offers credit and debit card funding options and supports 40 different fiat currencies, including EUR, CAD, GBP, TRY, INR and RUB, to name just a few. You can invest, trade, and earn yield, all within one place at okex.com. OKEx is not available to customers in the United States.  ======================= Exodus is an absolute game changer in the crypto wallet space, and we’ve teamed up to offer an exclusive discount for you, as listeners of the podcast. Sign up for Exodus today using my promo code Exodus.com/pomp. This is a no brainer for both newcomers and crypto heavyweights - go sign up today.  =======================

What's up, everyone? This is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Now, let's kick this thing off. Bobby Goodlade is the co-founder and general partner at Forum Capital, an early-stage venture capital firm focused on leveraging their design expertise. Previously, Bobby has made over 50 angel investments and was a former early designer at Facebook. In this conversation, we discuss the importance of design, angel investing, Hunting Deals, Rational vs. Irrational Investors, Facebook, Coinbase, Form Capital, UXUI and Crypto, and of course, Miami. I really enjoyed this conversation with Bobby and I hope you do as

well. Before we get into this episode though, I want to quickly talk about our sponsors. First up is Circle. Circle is a global financial technology firm that enables businesses of all sizes to harness the power of stablecoins and public blockchains for payments, commerce, and financial applications worldwide circle is also a principal developer of usd coin known as usdc which is the fastest growing regulated fully reserved dollar stable coin in the world now standing at more than 15 billion dollar market cap and is adding nearly 300 million dollars of net new digital dollars in circulation every single week the free circle account and their suite of platform api services bridge the gap between traditional payments and crypto for

trading, DeFi, and NFT marketplaces. You can learn more at Circle.com. I've had Jeremy, the CEO on the podcast before. I'm a really big fan of what they're building. So I highly suggest you go check them out at Circle.com. Stablecoins are going to be a big part of this market moving forward and Circle's doing a fantastic job. So head on over to Circle.com and let me know what you think. Next up is OKEx. Crypto moves fast and many crypto-focused companies can't keep up. Crypto exchanges that cut through the noise are the ones that give you access, wherever you are in the world, to the cutting-edge projects emerging in this new asset class. If you're looking for an industry leader that gives you access to a huge variety of crypto assets, tools, and services, I'd recommend OKEx. As we all know, Bitcoin and other crypto prices can be volatile.

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so you know they're good in my book. So head over to okex.com slash Pomp. Last but definitely not least are my friends at Exodus. Exodus has been supporting this podcast for a while, so make sure you go check them out. They're leading the world out of the financial system by building beautiful and user-friendly blockchain products. With its focus on design and user experience,

Exodus has become one of the most popular and loved cryptocurrency apps. It's supported on both desktop and mobile, allowing you to sync your wallet across multiple devices so you can have access to your funds anywhere. You can instantly exchange around 100 different cryptocurrencies straight from your wallet. Interactive charts let you view an asset's price history and your portfolio's performance over time.

And maybe the best part, Exodus is integrated with the Treasure hardware wallet, making advanced security easy for everyone. Visit exodus.com slash POMP for your free download or search Exodus on the App Store or the Play Store. Again, go to exodus.com slash Pomp for your free download or search Exodus on the App Store or the Play Store. All right, let's get into this episode with my friend Bobby. I hope that you enjoy this one. Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments.

You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only. All right, guys. Bang, bang. I've got Bobby here. We're basically just going to talk shit the entire time and tell everyone if you don't live in Miami,

you should move here immediately. Just kidding. What's up, man? How are you? I'm great. And are we kidding? Because I think people should move here to Miami. I think they should too.

We will get to Miami in a second. What did you do before you moved to Miami? And what, out of school, you worked at Facebook first? I did. Anyways, thanks, Pomp, for having me. And yeah, so my background is I'm a product designer by trade. Right out of school, I worked at Facebook. I was one of the first product designers there.

I was their first designer on the user growth team. So I designed a lot of Facebook's kind of onboarding and registration systems. So if you sign up for Facebook, kind of 2008 to 2012, give or take, you probably use some of my interfaces. And yeah, that's kind of where I started out my career. So I worked on the growth team at Facebook. That's right. We know a lot of the same people.

That's right. They are fantastic. It's probably the best growth team in the world, I would say. I think you would probably agree. Yeah. But you left in 2012? I did. 2013?

I did. Okay. What was the thought process between, I'm here at Facebook, things are going great, and then you leave to go do other stuff? What drew you away? Yeah. I mean, look, to be honest, Facebook just completely changed my life. It was an incredible opportunity.

And that user growth team in particular was just pretty legendary. You know, when I first joined the company, it was not the sexiest assignment to get. You know, I was joining as a new designer and people wanted to work on, you know, the stuff that's like front and center, the newsfeed, the profiles, photos. And to work on the user growth team is like not the most exciting assignment. But it kind of turned out that that team was this fairly legendary team. We kind of invented a lot of new design patterns for how to build these social networks. But yeah, and then I spent about four and a half years at Facebook, totally incredible place. And, you know, honestly, I was extremely excited to start angel investing and even had a specific investment in mind that I wanted to make, but I couldn't.

And at the time, in 2012, if you wanted to do angel investing, you weren't really allowed to as an employee at the company. Now, people still did, and I found that out after the fact that people kind of broke the rules and just didn't tell anybody. And so maybe had that been known to me, I maybe would have done things differently. But yeah, so I kind of left to start my investing career and, you know, kind of in retrospect, I think was fortunate that I left when I did. But again, like I owe Facebook just the world because it really launched my career. I'm in the exact same boat. I feel like I learned so much at Facebook, given that the user growth team at Facebook, we can joke all we want and be like, oh, they're the best in the world. Like they legitimately are the best in the world at this.

What are some of the things you took away from working with that team? And many of the leadership of that team is still there at Facebook, literally a decade later, right? So what were some of the takeaways for you? Yeah, I mean, that's a great question. I think like some of the takeaways were just ways of thinking about how to design new user experiences for startups. So, you know, we came up with this idea. I remember we called it the aha moment, which is that, you know, when a user is signing up for Facebook, they might be struggling through all these forms we throw their way. So we kind of asked them for all this information.

It's kind of a lot of work. And then I remember we did this one user test back in the day where we had someone come in and she was kind of suffering through the status quo of the onboarding flow. And then all of a sudden kind of got to this one screen, which was the screen where we could show the user, here's these folks that you might know. So based on the information she gave us, we could show potential friends from high school, from college, from her hometown, and just kind of this grid of faces. And then I remember we were watching this and we had like an eye tracking computer that could see where her eyes were looking on the screen. And then she kind of got to this step, and by the way, had she not been in the user testing lab, she probably would have just given up because she had to go through all these error states, and it was quite a mess to get here. But she got to this screen, and then all of a sudden, her eyes kind of darted to the friends she knew, and then her eyes lit up. She kind of leaned into the computer, or she was like, oh, wow, okay, I understand the value of what Facebook is.

And so that idea actually got us to completely re-architect the onboarding flow for Facebook. So we reordered steps. We took things that were kind of these really onerous steps like confirming your email account, and we put those as far back in the process as we possibly could. with with the idea of like how do we how do we kind of um um uh backload the the work behind uh the point where the users like really sold on the value of the product and so like so that was kind of like one i guess i guess and we we kind of we gave a talk about this idea and we kind of you know showed the um kind of before and after how much of this is like you just tested a million things that eventually saw this realized it and then like execute on it versus this was like a

preconceived almost thesis and then that's why you ran a like this specific test yeah so um a lot of the ladders a little bit of the former you know there are other cases where for example we had this registration form uh which was like the primary form that that everyone signed up to Facebook through circa 2008, give or take. And it had been A-B tested to death by all these different PMs. And someone said, okay, what if we kind of put this instruction text here? And what if we put this subheader here? And if we kind of put clarifying text here and there. And then basically over time, the form had just been kind of layered upon, layered upon. And each successive test had actually gotten to a point where it actually marginally improved the numbers but then

you know one of the one of the one of the funny things about the success i had at facebook was that um in one afternoon um myself and this ui engineer we were like fed up with this form we were like this thing sucks like let's let's redesign it and so i kind of just did a very basic cleanup of this thing. He built it, we had the thing test overnight. And in on the course of like 24 hours, we were able to increase the top level registration rate of Facebook. And this is like in 2008, by something like 5%, just by like cleaning up a bunch of kind of A B test nonsense. And so sometimes you have these kind of really easy wins that were just like, hey, let's just apply some very basic design sensibilities towards this. Other times it was more like, hey, let's really zoom out and look at what the bigger barriers are here.

Like, how do we kind of, how do we do these bigger architecture projects? But yeah, I mean, I think it was just a very experimental team. And then also one where the sort of eyes, the rest of the company were off of us. So we could really get away with a lot and just like continually run a lot of tests where, you know, if we wanted to put an obnoxiously big green button on things that maybe the other designers would be like, yeah, maybe we shouldn't ship that obnoxiously large green button. And but but they didn't really see these flows because they weren't signing up for new accounts or they weren't using the blank states of our of our of our apps. And so we were able to kind of get away with a lot of things and test a lot of things. And along the way, we actually really invented a lot of new design patterns. So when I was at Facebook, I was running the growth team for Facebook pages and you were doing this 2008, 2009.

This is now probably 2014 when I'm doing this, and one of the big wins that we had was on the kind of mobile web, like the M web or whatever, for really, really old non-smartphone phones, right, so kind of things where you would have to like click, almost like a T9 style, there would be a header, and so it would be things like, you know, home, profile, whatever, and you would have to click through to get to it. And so we literally one time moved create page from like the 27th slot to like slot eight. And all of a sudden there was an explosion in the creation of pages. And everyone was like, oh, my God, this is like amazing. And I remember somebody on the team being like, no one's ever tested this because nobody uses those phones. Right. Right. At Facebook. Like that's such an obscure thing. We forget how much traffic and how many users use that very obscure thing. And so what you just said about this kind of registration page that's also very unique to Facebook and was unique in 2008 but became even more unique over time was just the volume, right?

So you could run this test and 24 hours later have a statistically significant result that you knew as long as you ran that test correctly, right? Hey, is it better or is it not? Whereas a startup or somebody else, it could take them two months to get enough data, right? At Facebook, you got it in 24 hours. And so that iteration speed was just a complete superpower, I think, for the growth team. Yeah, and one of the takeaways from that that I've applied to some of the companies I've worked with since Facebook is that there's a basic idea that the interfaces that the employee base of your company use. So if you're on the team, you're kind of using the product day in and out, those interfaces tend to get refined and optimized just kind of naturally by the very course of employees kind of going about their way. If there's a bug in kind of the core workflow of your product and employees are using that workflow every day, it'll naturally get fixed.

But there's always these interfaces that employees don't use all the time, right? So signup flows are like the biggest category of this blank states where it's like, what happens when there's no data in the system and, and, and how to users interface with that. These things break constantly. And like, that was one of the big takeaways from working on that team at Facebook, which is like, we constantly had to do this cleanup work where everything that was in the eyes of the employee base was just totally scrutinized and cleaned up and optimized. Later in my career at Facebook, I was the lead designer for Facebook photos. And like, I, I redesigned the photo viewer, um, and we, we can iterate in front of the whole company.

We shipped a new version of the photo viewer, like every single night for, for, for about a month and like, believe like every, every little detail gets scrutinized. Right. But, but when I was on the user growth team, we were changing the signup flow for the products, which is actually far more important. If you think about it, then, then like, you know, where the buttons go on, on the photo viewer, um, no one had any feedback whatsoever because they didn't use it. And so that lesson has very much stuck with me. And it's actually almost a cheat code. When I work with some of the companies I work with now, once they're at a kind of established point, I think one of the things you can just tell them is have your employees go back and use the interfaces that

they're not regularly using. So have them sign up for the product again and again and again. Have them go through that new user experience again and again and again. And things will naturally get refined. Things will naturally evolve. One of the things that I remember taking away from that team specifically was this idea that every single test, in order to know if you're right or not, you have to perfectly execute and then be right. And the reason why perfect execution of the way that the test is designed is so important is because if you design a test and then you screw up the execution and it doesn't work, you're left wondering, was it the execution of the test that was wrong or it was actually the thing we were testing doesn't work right and i think that

that's when you get into this like very kind of testing heavy growth heavy type environment uh there's plenty of people who yell and scream and say it's horrible they're at least the bad things whatever but at the end of the day as a as a science as a way to use software to grow the metrics of a business bar none nothing beats that right in terms of the actual adherence to truth and the seeking of truth, right? And kind of this belief that like the code wins the argument or the data wins the argument. And I think that's probably the thing that you took away from Facebook and I definitely took away was just like that organization and that team specifically is, um, I think unrivaled in their like pursuit of that truth.

Yes. And I think it gave me a very good anchoring in product design as a, as a discipline. I think a lot of folks think about design in a very unserious way. They think about it as this more artistic pursuit. It's about making things look pretty. And I've never really had that attitude. I've always had the mindset, design is about solving problems. It's about kind of taking in a set of constraints and coming up with a solution that satisfies all those constraints. And then I think in an environment like that early Facebook user growth team, that really forces one to say, okay, is my design solving the problem that's on the table here? And we should be able to measure that. And I think that designers should really welcome that level of instrumentation and that level of metrics.

So I think this is after you left. The data point that I always tell people to kind of hint at, like just how data driven the organization is, is this is now 2015, I think they were trying to measure sentiment on Facebook. And how do you move sentiment? How do you measure that? Right. So what they essentially did was they created a metric called CAU, C-A-U, and it was the response to a survey question that was, does Facebook care about users? So cares about user CAU. And what they would do is they would basically show you various experiences or products or functionality or whatever. And then they would hit you with the survey.

Right. And they had surveyed you before and then they survey you after. And what was so fascinating about this was they could not move the freaking metric. Interesting. They could not move it. Right. And so I'm getting like a crash course in this. And I'm like, this is absolutely fascinating.

Right. You have what is not a data driven problem. It's usually more of like a psychological or sentiment-driven problem, but they're trying to measure it. And so what ultimately ended up being one of like the breakthroughs of this entire exercise was somebody put an interstitial at the top of the kind of news feed. And I forget what it was, I don't know, happy birthday or whatever, but they signed it from all of us at Facebook. From all of us at Facebook. survey bam cow moves this metric for the first time oh interesting and everyone's like whoa what was it like what moved you know and and you can just imagine like now all of a sudden like

there's movement right and everyone's getting really excited trying to figure it out and so they pin it down to from all of us at facebook that one phrase ended up moving sentiment and and increasing people's belief that facebook cared about the user right and so in hindsight i remember looking back and saying like, wow, you never, there is no path that you get to other than pure probability, just working in your favor of coming up with Facebook from all of us at Facebook, that would endear a more positive view of a company, unless you have that data-driven approach and you're actually measuring things and doing all this. But it's the adherence to like such a data-driven approach that not only makes Facebook, Facebook, but it's what led to

billions of users using the product, right? And things that you did on the design side go hand in hand with that, which I don't think people really kind of think of design and data really being the way that it works. Yeah. It's actually funny you kind of mentioned that change of messaging tone because way back in the day, we had some philosophies around what the voice of facebook should be like and it wasn't it wasn't that tone that you described it's actually far more you know like this is meant to be more like an operating system and less like a person speaking to you and i i kind of i had left the company at this point but i do remember like at a certain point uh you know call it 2014 2015 where i started seeing different um different styles

of messaging coming from facebook speaking to users i was like hang on a sec what's going on here. And so there you go. That's the explanation. Close the loop for you. All right. So you leave Facebook 2012, um, and you want to go invest. Uh, I know the story, so I'm cheating, but tell us a story about like, what are the first two investments that you go do? Yeah. Well, the first one was a payments company, which, which, um, I think I was in the right, um, the right general, uh, strike area, but didn't hit, didn't hit stripe. Uh, second one, uh, I was, I was fortunate enough to invest into Coinbase. And so that was my second ever angel investment. I was actually not liquid in the seed round in 2012, but as soon as I kind of became liquid from Facebook at the start of 2013,

I made my second ever angel investment into Coinbase. Okay. How do you find Coinbase? Why do you know that, hey, I should do this? And then explain this hunting process that you went through to track it down. Yeah. Yeah. I mean, it's a great, and it's something where I think like as an investor, I think it's really important to like study what your circle of competence is. How do you find deals and try to remember those things with like a certain amount of clarity. So like these days I write deal memos, the reinvestment I make so that when I look back in time, I can remember what my thought process was like when I made the investment back then. Unfortunately I didn't do these things, but, but yeah, I mean, I was basically a little bit of a

bitcoin nerd in 2012 um and um was it was in the r slash bitcoin subreddit and and i think we had bought my first bitcoins had to buy them through mount gox for those of us who remember mount gox and um and i i really do think that um um for me when coinbase came around it felt more like an obvious, an obvious improvement relative to Mt. Gox. I think for anyone who was in the community at that time, who had kind of suffered through the terrible user experience of Mt. Gox, to contrast that with what Coinbase offered was really quite compelling. And so that's kind of become one of my theses around how do I find these new breakout companies? I like to call it communities which see the future so and I think I've been maybe part of two of these maybe three

of these throughout my career so the first one was was was with Facebook where I was lucky enough to be a college student when Facebook started and so I think if you were in college at the time when it was college only no one outside of colleges could use Facebook we all had this sort of glimpse of the future and if you'd ask people in college in you know 2006 2007 like hey do you think everyone's going to start using this Facebook thing? They would probably say yes, versus if you talk to somebody who's on the outside who didn't have access to Facebook, they might just scratch their heads and not really understand what you're talking about. And so I think there's this famous quote by William Gibson, the future is already here,

it's just not evenly distributed. And I think of that in very literal terms. So when I was in college, I was kind of fortunate enough to be in this bubble of the future, which used Facebook. And then it became somewhat of a foregone conclusion to us inside of that bubble. Like, hey, this is going to expand to encompass a lot more people, maybe everybody. And then I had a similar feeling with Bitcoin in 2012 and with Coinbase in particular, which is like, well, I thought Bitcoin was kind of this bubble of the future unto itself. But then even within that, I thought, hey, it just seems pretty obvious to me that people are going to use Coinbase over something like Mt. Gox. And so at a minimum, like, this thing has some legs in terms of getting onto that level of market share. Now, did I know in 2013 that it would ultimately rise to where it is today? No, but I think that that lens of like, you know, what, which kind of bubbles of the future am I privy to, you know, what part of the future am I seeing that is maybe yet to be distributed to everybody? And I think like for a lot of folks, if you really, if you really kind of spend some time thinking about it, you can actually come up with some pretty interesting answers.

Yeah. And when you start to think about how to identify that, do you have to be in the community to know that that community knows something or is it possible for an outsider to understand? Yeah, I mean, obviously it helps, right? And there is something about that, you know, kind of firsthand experience where you kind of feel like a bit like an underdog and you just know this thing's going to do really well. and then you see these people on the outside who just don't quite get it and there's something quite special about that. But yeah, I do think that you can sort of systematically hunt for folks who are part of these communities of the future.

It's a little bit more difficult because I do really feel like, at least for myself, my own experience, I think that the best wins are going to come from where you can authentically engage in something and actually get genuinely curious and excited about it. I think like one of my criticisms, this isn't a criticism per se

of kind of the venture capital world, but like it's one of my dissatisfactions with how some folks approach the space, which is I think people don't get genuinely excited about the things they invest in, right? And when someone like truly finds something they actually care about and they really just get fired up about it like that's that's almost rare and when someone's a professional investor and they're kind of you know tasked with with hunting

down these things and and and and kind of putting out a number of investments on a regular interval um i think that that passion that that um that falling into that that that that that special community that sees the future like that doesn't happen that's a more rare feeling um and so even when you're a professional investor, when you're getting a lot of inbound deal flow, it's very hard to get deeply immersed in everything you're seeing because you're seeing so many pitches back to back to back. But then for my personal successes in my career, each one has really fit this pattern of like, yeah, I was kind of part of this early community of folks that really saw the future. And it was almost a sure thing to us when we were inside

that bubble. So how do you go from Bitcoin is going to be a thing to I'm an investor in Coinbase? What's the actual process? Yeah. I mean, maybe this is also my design background coming into play here, but I'm, I really, I really biased towards thoughtfully designed interfaces, interfaces that reduce friction. If you have to ask me like, what's the, what's the easiest way, what's the most straightforward way to make a product that's 10 times better? I think an answer that I would give you, although it's like kind of easier said than done answer is just create a 10 times better user experience, right? And again, it's easier said than done answer.

So for example, one of my companies these days is a company called Linear and they're a competitor to Jira, the task management productivity tool company. And there's like a million little reasons why I could tell you why Linear is like so much better than Jira. And it's very hard to put your finger on it,

but I think they all kind of sum up to this experience that is actually 10 times better. So design is kind of this cheat code in some ways to creating a product that is meaningfully better than an incumbent product. That was certainly the case with Coinbase relative to Mt. Gox back in the day. And again, you could kind of like,

you could kind of document every single reason why, you know, and in retrospect, a big reason why is because Mt. Gox turned out to be a scam, but that helps when you're not a scam and your competitor is a scam. Yeah, it turns out that's a good competitive advantage. But yeah, I mean, I generally think that focusing on user experience, focusing on design really matters. I think especially in financial services companies like Coinbase, where design is kind of a shortcut to communicating trust. So even before we knew Mt. Gox was a scam, it kind of just screamed scam when you looked at it because the design was terrible. It just looked like something that was a scam.

And so if you start from a point where you actually have thoughtful, considerate design, that communicates to a user a certain degree of trust. And then you just have to make good on it not being a scam part, and then you're good. So step one is don't create a scam. Step two is don't make it look like a scam. Right, right, right. And I can't help you if it's, if it is a scam, I'm not going to help you with step two, but like, but yeah, I mean. But, but when you see Coinbase and you're like, okay, this is beautifully designed, right? I think what's so fascinating is my understanding is a number of the best

investments you've made. It was not like somebody called you up and was like, Hey Bobby, we're like doing a fundraiser round. Like, do you want to participate? You were just starting out as an investor. And so you had to go hunting. You had to go get an introduction to the founder. You had to go and convince them to take your money, like walk through that process and, and why you were so willing to go do the work to go hunting. And this is something that's like really high on my mind right now because as I've evolved in my career as an investor, I kind of naturally get more inbound deal flow. Like I get a lot of people sending me deals right now. And then I always have to balance that against the fact that, hey, my best deal I ever did was not a deal that flowed

to me. It was a deal that I found out about and I went and knocked on the door and got into the deal. I would call that spear phishing. And I think in venture capital in general, we talk a lot about deal flow. And we think about deal flow as so much a part of the game. But I honestly think that it can be a double-edged sword. And I think some investors do better in different environments. And so for myself, when I was first starting out as an investor, nobody knew who I was. No one was sending me deals. I got no deal flow. But what that does is that affords a certain amount of kind of white space where I can get genuinely excited about things. I could spend all these hours on R slash Bitcoin. I didn't have pitch meeting after pitch meeting to take up my time.

And so you could find this genuine curiosity, this genuine excitement. And then, oh, well, here you go. Here's this new company, Coinbase. I've been in this community for a few months. mount gox is terrible i really need to do anything i can to go to go get into this deal and and i i think that that that mode of spearfishing is is a really compelling alternative to this idea of um you know i'm just gonna i'm just gonna have this gravitational pull of deal flow and have everyone come pitch me when what did you do to get an introduction to brian yeah yeah so again i i leaned heavily on my background as a designer and i had a had a friend of ours um make an introduction and um you know basically i i spent um two or three uh sessions in the office just

like helping them on their their new user account flows on some very basic kind of um onboarding um interfaces for for very early coinbase and then i said hey you know look i just made my first angel investment i'd love to make my second one into this like can i can i get into the next round and they said sure no problem and i think that idea of um of um of of offering something very specific in my case like a very a very minor amount of design support which wound up kind of widening and over the years i helped them recruit a couple designers i connected them to two different design firms uh later did like a more intensive uh onboarding review for for them And then they kind of rewarded me with that, with allowing me to invest more capital into

later rounds. And then ultimately was able to raise an SPV into the last round before they went public. And just all by the virtue of kind of spending a little bit of time and helping them with something that I was kind of relevant and informed to help them about. And so when you think about that deal and when you deployed capital, obviously you're going to have some hindsight bias, but do you think it's a $50 billion company? Or do you think it's like, hey, maybe they can grow and they'll get bought at 100 million? What's the upper bound of what you think that potential investment has at the time? Yeah. So I don't think I was... I think if I'm being honest, I didn't have these sorts of thought exercises fully established in my head

as an investor when I did it. But that's part of how I think about investing now, which is I think a really important question wherever you see an opportunity is you have to ask yourself, like, what if this goes perfectly right? Which I know sounds like a silly thing to say, and it might seem particularly naive for a Silicon Valley investor to say something like that. But I think the default for most people is that they default to cynicism and skepticism. And when you pitch someone a new idea, I think most people will start shooting down the reasons why it won't work. And those are really important to capture. And as an investor, you need to have that skepticism. You need to be able to do that level of intellectual rigor. You need to be able

to apply that towards the idea. But before you do any of that, I think it's really important just to imagine that kind of unicorns and rainbows scenario where everything goes right. And what that does is that it basically lets you ask the question like how much will this like where does this where's this uh peter out like where's this end and i think for for many ideas um you will find you will come up with some kind of cap where you say okay i think if this thing goes really well this is this kind of enterprise sas company and i think it could get to this level of recurring revenue and that would make it worth this amount of money and this is what the world looks like when everything goes right for this company.

And when you could find yourself coming up with like a very concrete cap and thereby kind of coming up with a pretty concrete expected value calculation about it, I tend to shy away from those things versus going after things that I think have potentially uncapped outcomes where when I start assessing,

okay, okay, what if this thing starts going right? And like, okay. And then with something like Coinbase and with bitcoin in general you start getting into these scenarios in your head where really you have to start thinking about like how governments are going to start responding to this thing and that's that's a really good sign when you start to if it's big enough for the government to be worried about it then you probably did it right as an investor yeah like that probably enters in this uncapped category outcome and um and and yeah i think um those are worth worth

we have because again it all comes back this sort of i like to call it a fuzzy expected value calculus where again like i think a lot of the a lot of mistakes a lot of investors make are that they're kind of overly scrutinous of ideas they kind of shoot them down and then the only thing the only thing that gets to the filter are these more capped outcomes they're more sure bets and you know when they when they work they sure they can they can result in some great outcomes But what I found in practice is that, you know, the failure rate between these sort of kind of smaller base hit capped outcomes and the failure rate between that and these kind of grand slam, you know, launch the ball into orbit outcomes, it's actually not terribly different. And if you're going to take the risk on investing in something that can go to zero and that takes on a lot of the same style of risks, regardless of what the startup is, you might as well really swing for the fences. Yeah. One of the things that to me is just absolutely fascinating is being rational is actually a hindrance to making good investments because what you're essentially doing is you're looking for something that's doing something different and right. And so it's an outlier and therefore it's irrational. And so if you're a rational person evaluating something from a rational standpoint, in most cases, you're going to miss the absolute most asymmetric things, right?

you're definitely going to find things that are less likely to lose money. So it's, you know, low probability of losing money or lower probability, but the upside is capped. The more irrational you are actually the higher the asymmetry is, but the lower probability of success. And as a venture investor, you want the latter. You don't want the, uh, the former. Yeah. Yeah. Or like, I also, I also think that, um, things that might feel really irrational, um, can actually, you can, you can flip over in your head to having a real rational belief in them if you can just get past this like one like immediate point of skepticism which is again why i think i think it's almost a cliche in if you talk if you talk to folks who work at these larger

venture capital firms and they kind of hire um you know like a junior person to come onto the team and they go to their first partner meeting it's almost a cliche that this new person will just like start firing out all these reasons why uh the idea that's on the on the table will fail and it's really easy to do that it's actually like it's and i think like it's table stakes for any investor is to be able to kind of come up with this list of of um of criticisms and like it's it's a very again it's a very it sounds very silly to say this but i think it actually is a worthwhile mental exercise to just like put those to the side and say what if everything goes right and like let's just pretend for a moment what does that scenario look like because at

least that gives you this upside calculation where you could start to get this fuzzy expected value calculation. Because again, the downside risk of all these things is the same. The downside risk is you lose all your money. And so when you find one of these things where you just can't even imagine how big the upside case is, even if the odds are quite slim, those tend to be things worth swinging at especially when you're constructing a you know a balanced portfolio when you think about uh investing you obviously are good at it you've had a number of hits uh you now have started an actual fund right form capital we can talk about that uh what is it that you enjoy about this but like why do you enjoy why did you not go and join another company and say hey i'm gonna go find you

know facebook 2.0 and um and kind of go do this all over again why have you spent so much time investing well part of it is that i think i'm a bit scatterbrained i really do enjoy um going from um working on a healthcare startup to working on a crypto startup to working on um uh you know a social game and uh i like i like as a designer i i really love getting involved in these companies and and kind of just trying on a new set of problems and seeing how i can i can resolve them. And so that somewhat speaks to our model with this new fund. So we're a very small seed fund. We're kind of a supporting fund. So we invest alongside other investors typically. And then beyond just a check, we offer what we call a design sprint. So with every investment,

we offer roughly 40 hours of hands-on design support. So we have a small team of designers on staff that works with our founders. And that's what makes it interesting to me. Because if I was just kind of writing a check and giving a wave bye-bye, I think it wouldn't be as meaningful, wouldn't be as exciting to me, wouldn't be as fulfilling. I think investing in a lot of ways is getting more commoditized. That's a good thing. And so for myself to kind of make it exciting, to make it interesting, I really want to have that participatory aspect to it. And that's kind of what I found with this new fund. The fund structure is very unique.

in that you intentionally are keeping the fund rather small. You're intentionally having a pretty large GP commit. Walk through just like, why are you doing things different than let's say a traditional fund would do? Obviously, you're very well connected. You've got a great track record. You could probably go raise $50, $100 million funds very easily. Why go after this specific strategy? Right, right. So I think there's two pieces to the fund. One is the value add, which is very exciting to me. It's kind of the reason why I do it. And then there's the economics of it. And the economic side of it also informs how I'm thinking about being an LP and other funds. So I'm an LP in about 15 different small seed funds, all around the same fund size

as mine. And I generally have this current market thesis around seed stage capital, which is that But obviously, we're all seeing an abundance of capital flow into this environment. There are a lot of funds that are lead check writing funds, meaning they've raised, let's call it between $50 and $80 million. And when you raise a fund of that size, you wind up having to invest a certain check size with every deal. And typically, for a seed fund, that would be something on the order of like $1 million five per deal. And what I've seen just firsthand is there's a lot of competition to be that lead

investor. I think there's a certain degree of adverse selection challenges that come with that. In other words, if you can't be the lead investor, it's a binary proposition. You're either in the deal or you're not versus these smaller fund managers and angel investors who put in these smaller checks, let's say they put in a 200K check as opposed to a $1.5 million check, they tend to get access to the deals that they want to invest in. And when they want to deploy an amount of capital into a deal, they tend to secure that allocation versus someone running a lead fund may more often than the smaller investor get rebuffed entirely. Or if the lead investor says, hey, I would like to invest a million five, and the founder comes back to them

and says, how about 200k? Well, that's kind of fatal to that investor, like you can't make the fund math work on an investment that size, versus if someone who's running a smaller fund comes to them and says, hey, I'd like 300k. And the fund manager comes back says, how about 200? Well, you can kind of make that work and still return the entire fund. And so when I think about how to structure both my LP checks throughout the industry and also how to structure my own fund in terms of like, how do I maximize the returns that I want to pursue? I think it's really important to be able to invest every time I want to be able to invest. And I think if you're running a lead fund in seed, you need to have a very, I think you need to be very honest with

yourself and ask yourself, am I able to invest every time I want to invest? And I'm increasingly seeing that answer as no. And again, I think like some of these seed funds that I'm LPing are probably some of the smartest investment checks I'll ever write. I actually feel very similarly about the LP checks that I'm writing right now as I did about the angel checks I wrote eight years ago. It has a very similar kind of feeling to me about it. And I kind of like this strategy. We call it like a nano fund strategy. What does that mean? Sub $15 million funds. Got it. So sub $15 million, not lead. How many companies on average do you think go into these funds?

It depends. Our structure is a little bit more weighted in that we like to put kind of more wood behind fewer arrows, but I've invested in other smaller managers who do 60 deals per fund, which I think is too much, but even so, it's a very big difference to me when you're able to get the allocation you ask for. I think that's almost like the most critical thing in terms of being a fund manager, where it's like, when you talk about investing, you kind of have to um, see the deal, right. You have to say yes to the deal and then you have to win the deal. And, um, you know, let's just say that, you know, those first two things are somewhat, somewhat table stakes in the sense that like, okay, you have to have, you have to have good

deal flow or kind of nowhere to look. And, um, you have to have good judgment and you have to say yes to the thing that's going to work. Um, this latter category is like, it's so much in controlled by the structure of how you run your business, right? Again, if, you know, investing is, you know, startup investing is like one of the few forms of investing where the asset picks the manager, right? What do you mean by that? Well, again, it's not enough for me to say, oh, I think this startup is really great. I'm going to go invest in it. Well, they might tell you, well, great. There's no allocation for you, right? Or we don't like you. Or we don't like you or any other things right and so and so and so i think a lot of a lot of um investors focus on

things like um again like how do i maximize deal flow how do i how do i think about picking skills i think a really important quality of any good investors they're being picked skill right and then there's like i think there's the two dimensions i can think of offhand to optimize for that is like um have something valuable to offer you know we've kind of we've kind of gone on with this design value offering. And we think that's compelling. And then two, like, you know, just structurally positioning yourself such that you can, you can be accommodated into these rounds. And when you have to eat up the whole thing, well, that's just going to limit the number of opportunities you can pursue. And so hopefully one of those lead checks, you know, a lead writer

will write, will wind up, you know, kind of being the grand slam they hope it is. But for myself, for my style of investing, I really like to structure myself in a way where I'm focused on finding things that I really enjoy, that I really want to invest in. And I don't like optimizing for doing this battle royale with some other startup investor. Who's going to lead the deal? I don't want to get into that competition. And nor do I want the fund managers that I back to be involved in that competition. I'd rather just get into everything interesting and I think go an inch deep and a mile wide in this category. When you think about crypto, it's something that seems like you're dabbling a little bit in. It's intellectually stimulating. The design is

horrendous, right? We spend a lot of time talking about early stage investing. Crypto is everything we just talked about on steroids, asymmetry, weirdness, all this kind of stuff. What is going on with the design the user experience the user interface is like one why is it so atrocious and two like do you expect to get better well it is getting better okay i think and again um maybe this is you know me having a hammer and thinking everything is a nail but i can really track the the ease of use of crypto and and i think i think runs in complete correlation with the mainstream adoption of it as as you've seen either either companies or um or projects that have extended um extended the user base of crypto i think they all have one thing in common which is

they they tend to be well designed they tend to be they tend to value user experience and i think there's there's there's a few cases of like some more esoteric um highly technical use cases evolving that I think can be very financially lucrative and that can drive adoption as well. But we were talking about like the mainstream general public adopting crypto. I think design has almost always been the limiting factor and will kind of continue to be for a long time. And so again, that's why it was very exciting for me to back Coinbase back in the day, because I saw that as like this really enabling factor for crypto overall. And I think a lot of folks in crypto really have a bias towards thinking about the technology, the protocols, the kind of

technical developments going on in the space. That's what's creating the adoption. But I think you really have to give credit to folks that make this easy to use, that make it accessible to everybody, folks like Coinbase, who have brought so many more people into the crypto universe. Is that probably the number one limiting factor to more mainstream adoption is just the user experience, the user interfaces of these products? I think so. And I think in general, like, design tends to, you know, follow behind the technical developments. In other words, like, there's a few projects where I think the end user experience becomes a goal at which the technology gets warped to accommodate. but that's kind of the exception, not the norm. In other words, like the technology is kind of

created as it exists. And then it's up to the designers to try to, you know, bang this thing into shape to actually make it easy to use. And I think some of the, you know, some of the most exciting projects that I see on the horizon are ones that really think about like, how do we make this easy to use from the get go? And it feels almost like the idea of crypto is so antithetical to like the way people have thought historically that already you're asking people to make a big leap on like the philosophical or kind of the point of whatever the product or service is.

And so the more you can make the design in some ways similar to what they're used to, right? Being user, very user-friendly, being easy to quickly sign up, being able to understand, hey, if I click on that tray, I know exactly what the action is gonna be inside the app. Like that seems to be in some ways missing,

but also like the lowest hanging fruit, again earlier you said like this idea of like design is the fastest way to kind of build trust or or signal trust in crypto like where else do you need that with some of these products then you know that industry right right and um yeah i mean i think i think um oftentimes it's it's a it's a smart idea to maybe build an interface that um that borrows heavily on um kind of a mainstream uh financial interface that folks might already be familiar with that that maybe has to be a bit shoehorned into crypto but but but if it's something that people can immediately grok and understand like it's it's almost worth having that um that simplification that reduction

just in order to get people to understand it and i think i think sometimes we build uh we really reinvent the wheel we build highly technical interfaces when uh a more simplistic reductive interface maybe something that hides some of the options that people don't necessarily need to tweak um is going to be the better choice and how much of um what you're looking at in crypto is like infrastructure so like coinbase is an exchange it's a piece of infrastructure there's hundreds of other pieces of infrastructure versus more like protocols tokens and like what i'll consider like more of the extreme end of crypto that's not necessarily infrastructure it's kind more of the quote-unquote new stuff right well i'm looking at a smattering of things right now

um at the moment i have like very specific um there's like specific apps that i want to exist and i'm like hunting for those do you want to share them so that people can come inbound or no um um you don't have to yeah i mean um give us one yeah yeah so um and i'm already looking at things in this category as well so so i don't necessarily need a bunch of inbound pitches but but please you know bobby formcapital.com please drop me a line um so if you think about bitcoin as creating a sense of digital scarcity and obviously there's a financial product attached to that with bitcoins i think something about this whole nft explosion that's excited me is this idea of can we take objects in the physical world that already have real world scarcity and can we

digitize them can we financialize them and so for example um collectible cars uh trading cards collectible watches these things in a sense already have a scarcity algorithm if you will In other words, in 1952, Mercedes made only so many 300 SL Gullwing cars, right? And so the minting for that car has already happened in the past. And so as you look at digital currencies as sort of this means of creating artificial scarcity and then mapping a financial instrument to that, can we take actually scarce physical objects and then pair them with a digital token, maybe a fractionalized digital token, and then make that into a financial instrument? So that's like one thing that I'm kind of broadly interested in. And that's really trying to anchor physical goods in the digital world, but still be able to prove kind of provenance over it and also the scarcity, who originally made it, created it, where to trade hands, etc. But it's a physical item, not a digital item, but the digital world still kind of respects or acknowledges the physical item.

Yeah. And I think in terms of this becoming an asset class, I think maybe a lot of your listeners would agree that gold is sort of under fire as taking this hedging position in people's portfolios. And something like Bitcoin offers a pretty interesting alternative, but I can even imagine a future where there's a basket of actually scarce, kind of provably scarce goods, some of them digital, some of them physical, that replace what has been gold. Maybe gold is a piece of this basket, but it's not the entire basket. And so this idea of like financializing scarce assets is interesting to me. All right. We're recording in Miami. We're in person. I think you may be one of the only people other than like Keith and Delian who like Miami more

than I do. Why did you move to Miami? And then what are your thoughts so far? Yeah. So, well, so far it's been fantastic. As to why I moved, I've lived in San Francisco for about 10 years and kind of just watched this wave emerge starting in last November and kind of got to the point in December where I was like, you know what, this seems pretty fun. A lot of people I respect are coming here. Why not take a bit of a flyer on this? And then if I don't like it, I can kind of, you know, go back with my tail between my legs. And we kind of got here in January and have really just only seen upside from this, have just been tremendously happy about the move. You know, one kind of thought process I had for myself as an investor, you know, I could be

one of thousands upon thousands of small new seed funds in the Bay Area, or I can be one of a tiny handful here, be part of this kind of exciting wave. It feels like very rebellious, very exciting. there's there's a lot of camaraderie about it um and um you know have have a mayor hype us up and um and and i said yeah it's like it's almost a no-brainer and um again i really have um i've really felt very little downside to the move so far and a whole ton of upside a lot of friends of mine kind of told me you know you'll you'll move here and then you'll just kind of be kind of bored to tears you're you're gonna be always pretty boring people and it's been the exact opposite. It's like I've had interesting person after interesting person kind of come into my

life. My calendar is completely booked in terms of deal flow, in terms of work. I've never been busier. And that's very much taken me by surprise. And it just kind of makes it all the more exciting. So the two things I always tell people is one, people who moved here are not moving here to retire. Right. People are moving here with a chip on their shoulder and they're here to work. and uh that alone you can feel the energy when you're here when you're meeting with people etc is that uh the folks who are here are not going to stop until this is successful yeah uh and then two is i think you're very similar to me in that like i'm just happier here yes right and i literally don't know if it's as stupid as like it's sunny all the time right and so therefore you're happy

i don't know if it's because it's a new place i don't know if it's because somehow i'm uh eating healthier food like i i literally have no clue right i just know that when i'm here i feel happier than anywhere else yeah and that alone is the reason for me to be like yes i should live here and we all want to make it work and i think like that is like if i had to pitch a founder on coming here and and starting their company here as opposed to the bay area i think that the camaraderie and the the kind of um the the this like unified sense of like hey we're all trying to make this thing happen and and so you're you find up getting a lot of support and contribution from people who if this was all back in the bay area like you know they wouldn't they wouldn't

give you the time of day but because we're all just like trying to make this thing happen um it's really it's really an awesome feeling it's something i haven't felt in this industry um since maybe like 2010 and i remember like going to you know going to parties in san francisco like 2011 like the the airbnb people they had like house parties like okay kind of similar vibes to what i'm feeling here or like south by southwest circa 2008 where it was a small enough community you can kind of get to know people you can you can i've kind of converted a lot of um online friendships to in-person friendships this you know ourself included and like it's awesome it's like um there's honor among thieves right that's the way i think about it right is we're all in this together right

right and it does feel like a little bit of a rebellion like it feels and and you know there's there's people who really um take umbrage with this um and that kind of makes it more fun you know i saw i saw today that um tyler cowan had an article where he's you know um not not so excited about Miami being a tech hub. And I'm like, you know, I respect the hell out of Tyler Cowen, but like almost the doubters give us some amount of energy.

I was going to say that literally means we're onto something. Right, right, right. It's kind of like a startup. If you keep hearing no a bunch of times, you're probably onto something. Right. More so than not, if you're right.

And same thing here. It's like the more people yell and scream, they're like, no, it can't happen. No, it can't happen. It actually convinces me like it's going to happen. Right. There's a certain amount of like self-compounding narrative to this uh that that that people who are uh you know very vigorously against it i think

they don't fully appreciate how much they contribute towards it um and then i think it just leaves folks like yourself and me to just be generally positive about it because again i'm only seeing positives and um it's just such a such a fun thing to be part of and such an easy uh, welcoming community to join, uh, that, uh, it's just a really fun, fun thing to do. I couldn't agree more. Uh, I got three questions before we end and you could ask me one first is what's the most important book you've ever read? Um, man, I didn't get any no prep coming. Yeah. So, um, there's a book called the denial of death by Ernest Becker. Okay. It's kind of a, um, psychology slash philosophy book. Why is that one stick out to you? Um, I think it,

it helps explain and frame how people think and how, um, you know, our, our mortality is this like very, uh, um, interesting motivator and guiding force for, for, uh, you know, for how we, how we view the world. It's fascinating the topic of mortality and how important that is, right? Because I think when you get reminded of that, it focuses everything else. Right, right. And so much of our society is designed, and this is what the book talks about, is kind of designed to build these trappings that help you forget about the fundamental mortality. Sleep, second question, comes from our friends over at Eight Sleep. Yes.

they have this thermoregulated bed i sleep on it every night i love it um i put mine really really cold and i sleep like a little baby what's your sleep schedule now and how has that changed over the years um i also have an eight sleep nice and it has markedly improved my sleep so cheers to them and uh this is becoming a trend now on the podcast ask this question oh i haven't eaten sleep of course and then they go and they cut the clip and they put it on uh the internet look at how smart we are um i mean it's probably one of the few things that actually can make you like notice notably smarter on a day-to-day basis just getting a good night's sleep so yeah it's crazy it literally is crazy yeah why not what did you used to do did you sleep like five six hours or were

you always a pretty good sleeper well um again i'm very pro miami so i don't mean to be anti-sf but But I'll be anti-SF in one dimension, which is no one has air conditioning in San Francisco. And so I was just sleeping, you know, sweating, you know, sweating bullets. And everyone said, oh, you're going to be so warm here in Miami. I'm like, no, no, actually, I'm having to adjust to like set the AC to the right temperature. I'm actually too cold most of the time. So I got to adjust to that new reality. Yes.

I love it being cold. Most people ask me, like you remind me, why do you always wear a hoodie? It's because literally we keep the office cold as well. Yeah, I mean, look at me, man. Um, last question is aliens. Are you a believer or non-believer? Um, in the, um, in the science fiction movie aliens, I think it's one of the best movies of all time and actually just rewatched it the other night. Uh, as far as the, um, as far as the actual extraterrestrials, um, I don't know. I think, I think that's the only fair answer to get, but all right. I sure hope they're not

like the James Cameron aliens. Um, I'm with you on that. I think everyone's with you. That would be bad. That would be bad. Well, one question you have for me, um, you know, where, um, so what would you like to see happen in Miami next? Like what, what's your vision for the next year of all this? I think just having more founders, start more companies here and having more success. Like I'm a big believer that success, but get success. And therefore, if you have big companies built here, then people will spin out there, create their own companies, big exits. Then people get capital. They can invest. And like, it just, you start the flywheel, right? Um, and so like, that's kind of like a bland answer, frankly, but like, I think it's just

like blocking and tackling, like, Hey, how do you make a place a tech hub? Same way that Silicon Valley made themselves a tech hub, right? Like get investment, build big companies, start new companies, get investment, build big companies. And like, and you just start the fly wheel. And the next thing you know, like the institutional knowledge of how do you build big companies gets built up in a space. People come to that place because they want capital. They want knowledge and they want workers. Right. And you're off to the races. And so like we're pretty damn far down the road already in terms of some of the companies that have moved here. Now you just got to start the flywheel and do more and more and more of it faster and faster. Well, we should

look at co-investing on a Miami company together. Do you have some? Maybe. I don't want to spill the beans here on camera, but let's work together on this. Just send it my way. All right. Where can people find you? What? Bobby at formcapital.com? Bobby at formcapital.com. I'm at RSG on twitter and that's about it how did you get rsg let's do it hold on you guys those are my initials i was just i was just really early just really early got the initials and done if you want to add me on facebook here's a here's a flex for the kids at home all right uh facebook.com slash g wow too bad no one actually uses facebook usernames for anything so that one was facebook.com slash g that's pretty good uh that one's a total whiff because uh no one like who who cares about

facebook usernames right so i have facebook.com slash pump that's pretty good uh and at the time when i was working there they didn't give out the four letter names and i like begged i was like come on like i gotta get this i gotta get it uh and eventually i got it and i was like yes and i can't believe i'm about to tell a story the way that i convinced them to give it to me was uh boz yeah has slash boz b-o-z and i was like he's got three letters i'll even take a fourth letter just give me slash bomb so finally i found out who who was doing it and got it and whatever but slash i've never heard of a one letter there are a few of us obviously there's less than uh less than the numbers in the alphabet yeah less than a number of letters in the alphabet

i love it all right and then uh formcapital.com slash uh dot co.com capital.com yeah all right awesome man thank you so much for doing this we'll do it again this was so fun yeah thanks for having We'll be right back.