Keith, thanks for having me over.
Pleasure to be with you. Yeah, I'm excited to chat and catch up.
So, I think there's a few things we're going to talk about today, Keith. One is we're going to talk about you a little bit. We'll start with your childhood and us working together and then we're going to talk about Aven and machine banking in general, overall.
Sounds great. Awesome. Let's get rolling.
So, to introduce Keith a little bit to everyone else who's watching. Keith, you and I met first as part of OpenDoor and you're obviously one of the founders of OpenDoor and helped build and shape that company. And I was at Facebook at the time and you guys had reached out and I was like if there's any company I would work at, it would probably be OpenDoor. It's intersection real estate which I love, technology which I love even more, and financial services. And I remember going through the process, meeting you and Eric and the team and I was just like, oh, these are great people. I could hang out with them. This is almost a decade ago, I think 8 to 9 years ago.
Yep, 2017, 18 max, maybe 16.
Actually. Yep. Yeah, and I think we met and I remember distinctly the conversation we had at that coffee shop. And we struggled a little bit to find our way to this coffee shop, but we found our way and at the end I remember you telling me, well, even if you don't join, if you ever start a company, you make sure you call me. And so, few years later when we decided to do Aven, you got that call and I came and hung out with you at Founders Fund and that kicked off the whole thing.
Well, it's great if you know, OpenDoor would probably be a hundred billion dollar business if you'd accepted that offer. You know, I wouldn't have had to spend last year fixing the damn company, but one way or the other we made it work out.
We made it all work out, I think. That's great. Let's go to your childhood a little bit. And let's start there. You know, one of the things I love learning about people is what are kind of their formative experiences in like elementary, middle, or high school. So, you know, tell me a little bit about what was like a really hard problem or a hard experience that you had.
So, I don't fit the central casting. You know, I know there's lots of very successful VCs and people who use this sort of prism for interviewing of like what were the hard challenges you confronted as a kid and how they make you this person and blah blah blah and you became resilient and ambitious and all this. I had a pretty normal childhood. I mean, I was like kind of middle class kid, ambitious, introverted which we could talk about. And so, I'd read. I read the World Book Encyclopedia from cover to cover. That's what I would do for fun. I'd come home every day and read a different volume after soccer practice. So, the biggest challenge I felt when I was growing up was I was naturally introverted and I had ambitions to do things let's say in politics or other fields, law originally, that required to be extroverted. And so, that challenge of how do you ideally sit on a sofa by yourself and read a book, but you have goals professionally and otherwise that don't allow you to do that. How do you reconcile those things? So, I used to struggle with that from junior high school on.
Oh, that's something we actually have in common. So, I was also a very introverted kid growing up and I was similar to you. Like reading was my passion. I could go into a universe reading a book. And an experience in sixth grade changed me where I really liked this girl and I wanted to ask her out, but somebody else asked her out for the dance. And I was like, this is not working out for me, this introversion thing. And I had to figure out how to be extrovert. And between sixth and seventh grade, we changed schools. And so, my great relief valve in my life was always I changed schools a lot. So, it allowed me to reinvent the next version of myself.
Interesting. Yeah, I didn't really change schools. I went to after first grade I didn't change schools at all. But what I actually did is I basically figured out ways to challenge myself and just said I'm going to force myself. I didn't do the proverbial theater kid acting, but I did like a lot of debate and pseudo debate and stuff like that and you're on stage. And like you're on stage in front of hundreds of people, thousands of people and like, you know, I gave an address to the UN Assembly and like did crazy things. So, once you can give a speech like that, you learn to do that, you can dial it down into a microcosm sort of. And so, I sort of put myself in the same thing even professionally. Kind of a funny story from 2015, I guess. My friend's birthday, 30th birthday was coming up. I was actually an engineer at Facebook and I wanted to do something cool for his birthday. So, I learned to teach a Barry's class which still created this kind of terrifying moment for me of being on stage in front of 50 people with very tight time constraints and I got incredibly nervous and practiced for like 6 weeks in a row to learn how to do this. So, I still like you can still use challenges like that that are a little artificial in that case, but to force myself to get more comfortable.
Huh. That's great. Actually, you mentioned something really interesting there. You did a speech at the UN General Assembly. How old were you?
Um that would have been the full address would have been senior year high school first time. That's pretty young. Um started actually sophomore year. So, one of the ways I did well in high school was like these kind of competitions sophomore, junior, senior year and you know, we won like these national championships and stuff like that. Um and then later I got to run various organizations and give another one that actually my parents were able to attend which is kind of cool.
That's awesome. There's two things here that are interesting, right? One is that one of the two things that apply a lot to how we do recruiting at Aven are we actually look a lot at what people did in high school to understand their trajectory. In fact, one of my like specially or exclusively weird things at Facebook even where I would look at resumes and look for things on LinkedIn and resumes and what kids did in high school because I really think the world underestimates young people by a huge margin. Systematically. I mean, you've probably heard my speech about like I think hiring interns is the best thing a company can do especially in design and engineering.
In high school actually interesting enough, I hadn't thought about this in a while, but fundamentally I actually coded in high school. Oh. I was actually pretty good at for high school. Like think of languages that no one will remember like Pascal and Fortran and That's pretty sick. Not really Cobol, but in any event I stopped. I went cold turkey after senior in high school. I did not code anything for 20 years.
Like so, but I went every other direction. Now I finally the tools are easy enough that I actually might be able to code stuff again.
You know what's interesting is that you chose to become a lawyer. Yeah, everything you could do is opposite of coding.
So, let me be a little contrarian on that. I actually think the lawyers that I've worked with that are really good and the engineers I've worked with that are really good are more similar than different.
So, you can actually see this in LLM adoption. Think about the two verticals that are two of the three, coding and legal AI and customer support probably the third. So, large language models are basically proving that the way engineers think and the way lawyers have thought and trained. It's a discipline. I think being a lawyer is very helpful in organizing thought. I think there's some positive selection bias of who becomes an engineer in life and who becomes a lawyer usually has a pretty high IQ, fair amount of discipline, writing skills, expression, logic. Logic. And oftentimes, you know, like the joke that I have with the team is there's a boot camp that we do at Aven where we do a talk to help people onboard into a somewhat esoteric culture of how we work at Aven which is like deeply technical. And one of the kind of key things that we talk about is how do you know the boundary conditions of a solution to a problem and we always talk about there's two real boundaries on how we solve any problem in the world. One is the laws of physics and the other one is the laws of the land. And my world that laws of the land are the regs that and somewhere effectively the source code of society in many ways and it just happens to be expressed in the English language. But, you know, one of the things is you probably know is when we started Aven, we started by reading all the regs that would be applicable. I read TILA and Dodd-Frank Act and I view the regs as just source code of regulators.
So, I got another funny analogy for you. My first day at Square, literally the first day, I used to sit at a table like this. Jack Dorsey would sit here and I'd sit here and his EA would be there. First day, I sit down and I pull out the entire Visa Reg Manual. It's like about 900 pages and I read it cover to cover. And everybody's looking around. There's only 17 people in the office so everybody's like seeing what I'm doing. And they're I was like, you got like I need to I need to know this stuff and like then I can manipulate it.
Yeah, understand and manipulate it, build on top of it.
Let's transition to your experiences at Square. I mean, one of the unique things about you is that obviously you're a very successful investor, but I think you're also a very successful operator. And that's a very unique juxtaposition. Most people do one or the other. Walk me through that kind of transition. You've obviously kind of gone back and forth and done more.
I spent yeah, I spent most of it like I spent it mostly did it sequentially. First 13 years building companies, you know, started at a failed company that went to PayPal, then LinkedIn, and then mediocre company called Slide, and then Square and became an angel investor along the way sort of by accident that I started investing while I was building. 13 years ago now, it's exactly equal in time, I became a professional investor known as a VC. Most people are better at one or the other. I think for example, if you're intellectually curious or ADD, being an investor can be a very good profession. You learn you're paid to learn new things. I actually think it's the only maybe the only field in the world where you get paid to learn new things. Like journalism, you supposed to learn new things, but you don't get paid.
So, love this job if you're ADD. You're context switching every hour on the hour. Different stage company, different market, portfolio company, new opportunity and you have to thrive. You have to be someone who thrives like that. And so, you can turn ADD to a competitive advantage. Company building is mostly about going deep and mastering problems and solving them going all the way to the metal so to speak or literally so to speak literally. So people who tend to be great at dialing in tend not to be ADD. And so very few people I think are great either executives or founders and investors. But there are some people but it sometimes when I meet a friend and they ask for career advice I can tell like this person's very ADD like tell him tell it would be a terrible executive. He's a good founder he founded a pretty good company but like he is intellectually curious and ADD on steroids and he's a very good investor. And then there's other people who are masterful executors. Masterful but they would be terrible investors.
That's great actually. Um in fact in some ways you did both at OpenDoor right where you can experience and OpenStore. So let's talk about OpenDoor.
So OpenDoor one of the reasons why I did that it was I was parallel tracking the idea of starting OpenDoor we used to call it Homerun that was the original name the original trademark and all this stuff. Our original IP while I was considering being a VC and someone you know who's one of the early engineering managers at Facebook I was trying to recruit to be my co-founder and he spent like he's very disciplined about it and he spent all this time studying analyzing refreshing his skills about statistics and all this stuff and he took just a little too long. So I finally felt the pressure to accept joining KV then we did a press announcement two hours after that announcement I get this long email from this person saying I'll do it you know I'm convinced myself I'm ready to go and I'm like oh my god this is the worst possible timing.
So what I decided to do is figure out how to still pursue it unfortunately I couldn't co-found the company with him it's a really unfortunate but if you sent me the email a day before we would have founded and who knows maybe you'd still be a hundred billion dollar business.
That's awesome. What's one thing that you know especially in that overlapping experience what's something that you learn as an investor that made you a better operator?
Well you do get to watch like I get the benefit of now 13 years of working with some of the best entrepreneurs ever and I get to watch what they do how it's different than what I used to do or what I thought you were supposed to do and take advantage of it like there's things I've learned from you like there's things and I you know you kind of take that into your own build your own custom brew and style whereas when you're learning how to be an executive you really only learn with the people that you work with and I had the advantage of a couple company cultures like LinkedIn was very different than PayPal for example which is different than Square. But you only have so many learning environments. Now I work with 15 entrepreneurs closely like at the same time and you know let's say a third of them are world-class. Something like that. So I have five world-class people to learn from like every year and then I add new ones and some go public and you get new ones and so you learn so much and then I try to absorb it so you change some of your views or mix some new ideas in.
What's something that's esoteric and weird and surprising that you learned?
Well you know so I usually eventually share them publicly like I put them out as tweets like I put one that you taught me like out as a tweet which was the you know why you should be basically criticizing people in the company leaders etc. in public which is very contrarian to how most people teach people to do management but it makes so much sense once you understand it and decompose the logic and so I put that out there. So I tend to absorb and then re-share.
