The Exchanges

Q Does that not go contra kind of entire portfolio thesis when you think about it? In terms of, does it, does it go against a, yeah, in terms of if anyone said that they're putting their whole fund in one company, would it not go completely contra anyone's ever?

A Yeah, absolutely. The thing is, when you're sitting there, we were debating the check size initially, and, you know, when you're talking about putting in 50 to a hundred million dollars into Uber, you're thinking, okay, well, that's pretty much, you're, you're still dependent upon Uber's success to make this fund back, largely, so why not just Do the entire fund. So for us, it was, it was, we were kind of teetering on, should we do a much smaller check? What should the dollars be? And then eventually we got, okay, let's do a hundred, let's do a 150. And then we realized like, it just, it really doesn't make any sense at that point, um, one way or the other, and they needed the capital. So let's just put the entire fund in. And for us, GB was a little bit different than your, your typical fund that is invested over the course of two to three years, whereas ours was refreshed annually. So We had a brand new, uh, you know, three hundred million dollar checkbook come January first.

AI assessment note: “Yeah, absolutely. The thing is, when you're sitting there, we were debating”

Q Can I ask, how's your thought process transitioned from making those early stage, 10, 20, to then obviously, as you said, scaling up 50 K angel checks to now, and when you're at GV, when you were investing from an instant Institutional perspective with a team. How did that kind of psyche and mental approach change?

A Yeah, I mean, the nice thing about GV is that you had a handful, there was seven other partners around the table that made the investment decisions. So having a, I think two, two ways into that it changed. One, I received exposure to a whole asset, a set of assets that are asset classes that I would never have thought of before. I mean, I'm not a life sciences investor, but We had, um, the Krishna, for example, was our, our kind of life sciences, um, guru, where he's a MD, PhD, and brought a lot of really interesting deals to the table. So you would see investment that I typically wouldn't go after that were being brought to the table. So that was a lot of fun. But in terms of just general thought process, we would bring these deals to the table. And ultimately it was kind of a round table debate and we'd hash out whether or not we thought it was a good deal to put our funds into. Um, And then we would take a vote and ultimately decide whether we wanted to do the deal or not. So it was just a different process in that, you know, when you're an angel, you go out, you meet with the founder, you sit down, you have a coffee, potentially do a second coffee. There's something you want clarified or you want a little additional data. And then you just decide to do it, you know, kind of on the spot. So this is a little bit more thought out and the check sizes are completely different. I…

AI assessment note: “I think two, two ways into that it changed. One, I received exposure”

Q Does that not go contra kind of entire portfolio thesis when you think about it? In terms of, does it, does it go against a, yeah, in terms of if anyone said that they're putting their whole fund in one company, would it not go completely contra anyone's ever?

A Yeah, absolutely. The thing is, when you're sitting there, we were debating the check size initially, and, you know, when you're talking about putting in 50 to a hundred million dollars into Uber, you're thinking, okay, well, that's pretty much, you're, you're still dependent upon Uber's success to make this fund back, largely, so why not just Do the entire fund. So for us, it was, it was, we were kind of teetering on, should we do a much smaller check? What should the dollars be? And then eventually we got, okay, let's do a hundred, let's do a 150. And then we realized like, it just, it really doesn't make any sense at that point, um, one way or the other, and they needed the capital. So let's just put the entire fund in. And for us, GB was a little bit different than your, your typical fund that is invested over the course of two to three years, whereas ours was refreshed annually. So We had a brand new, uh, you know, three hundred million dollar checkbook come January first.

AI assessment note: “Yeah, absolutely. The thing is, when you're sitting there, we were debating”

Q Can I ask, how's your thought process transitioned from making those early stage, 10, 20, to then obviously, as you said, scaling up 50 K angel checks to now, and when you're at GV, when you were investing from an instant Institutional perspective with a team. How did that kind of psyche and mental approach change?

A Yeah, I mean, the nice thing about GV is that you had a handful, there was seven other partners around the table that made the investment decisions. So having a, I think two, two ways into that it changed. One, I received exposure to a whole asset, a set of assets that are asset classes that I would never have thought of before. I mean, I'm not a life sciences investor, but We had, um, the Krishna, for example, was our, our kind of life sciences, um, guru, where he's a MD, PhD, and brought a lot of really interesting deals to the table. So you would see investment that I typically wouldn't go after that were being brought to the table. So that was a lot of fun. But in terms of just general thought process, we would bring these deals to the table. And ultimately it was kind of a round table debate and we'd hash out whether or not we thought it was a good deal to put our funds into. Um, And then we would take a vote and ultimately decide whether we wanted to do the deal or not. So it was just a different process in that, you know, when you're an angel, you go out, you meet with the founder, you sit down, you have a coffee, potentially do a second coffee. There's something you want clarified or you want a little additional data. And then you just decide to do it, you know, kind of on the spot. So this is a little bit more thought out and the check sizes are completely different. I…

AI assessment note: “two ways into that it changed. One, I received exposure to a whole asset”

Q How do you respond to that? Like, I honestly, I'd love to hear how you bring yourself back and re-repeat it. Do you know what I mean? Not re-repeat it, but kind of just bring yourself up from the ashes.

A Well, I think it's, it's really sitting down with the founders and encouraging them to find their own personal balance. And that can be different for everyone. You know, they need to have and understand that life is not just their startup. If they believe that, then eventually they will burn out. They have to figure out what are the two or three things that they must do every week in order to feel as though they got a proper balance of both work and personal life. And that can be different for everyone. For me, I'll tell you, it was going to the gym three times per week. So, you know, for me, I was making sure Monday, Wednesday, Friday, I would carve out some time during the work day and go out and hit the gym for an hour, hour and a half and sit in the sauna for And that reset allowed me to be more productive. It would allow me to, you know, I'm not, I'm not talking, I'm not talking about, you know, working four hour days here. We're still all working very hard. It's just really finding downtime to, to oftentimes let your, your mind just have a moment of silence. And I find that that allows me to be more creative. If I'm constantly going and constantly being strung out on caffeine and working until two or three in the Functioning optimally. And I feel like that is going to hurt my creativity longterm.

AI assessment note: “For me, I'll tell you, it was going to the gym three times per week.”

Q appreciate the enlightening. Uh, I do want to ask one particular thing though, in particular, with regards to your podcast, you did the foundation. And now you're doing the journal. I love both of them. But I do have to ask, obviously, as a podcaster turned VC myself, what are your big learnings from doing this show? And what's the kind of driving force for you to do the show?

A You know, around foundation, it was really to hopefully inspire a new generation of entrepreneurs to let them know that when they hear someone like an Evan Williams or a Systrom or Elon Musk on the show say, That I really wanted to take, you hear the standard Bloomberg interview, and it's all about talking about finer details of the actual business and, and things at scale and these big intimidating questions that these CEOs are quite good at navigating. But one of the things that they really don't tap into is just like the human aspect of the entrepreneur lifestyle. And I, and I think that sitting down and talking to Elon Musk about how he got into tech and his comic book collection as a child, uh, And, you know, his favorite books and things of that nature. That was kind of a side of him and of these founders that I wanted to expose to everyone because once you, you sit down with these founders and you, and you speak enough about their just kind of general day to day life that is outside of, of work. And of course I would touch on their businesses as well, but you get to understand that they, they kind of, the whole old saying of they put their pants on one leg at a time is, is very, very true. They still make the same mistakes that you and I do. And just exposing that kind of realness of the founder, I think was the goal of foundation was to let other entrepreneurs know that…

AI assessment note: “exposing that kind of realness of the founder, I think was the goal”

Q appreciate the enlightening. Uh, I do want to ask one particular thing though, in particular, with regards to your podcast, you did the foundation. And now you're doing the journal. I love both of them. But I do have to ask, obviously, as a podcaster turned VC myself, what are your big learnings from doing this show? And what's the kind of driving force for you to do the show?

A You know, around foundation, it was really to hopefully inspire a new generation of entrepreneurs to let them know that when they hear someone like an Evan Williams or a Systrom or Elon Musk on the show say, That I really wanted to take, you hear the standard Bloomberg interview, and it's all about talking about finer details of the actual business and, and things at scale and these big intimidating questions that these CEOs are quite good at navigating. But one of the things that they really don't tap into is just like the human aspect of the entrepreneur lifestyle. And I, and I think that sitting down and talking to Elon Musk about how he got into tech and his comic book collection as a child, uh, And, you know, his favorite books and things of that nature. That was kind of a side of him and of these founders that I wanted to expose to everyone because once you, you sit down with these founders and you, and you speak enough about their just kind of general day to day life that is outside of, of work. And of course I would touch on their businesses as well, but you get to understand that they, they kind of, the whole old saying of they put their pants on one leg at a time is, is very, very true. They still make the same mistakes that you and I do. And just exposing that kind of realness of the founder, I think was the goal of foundation was to let other entrepreneurs know that…

AI assessment note: “around foundation, it was really to hopefully inspire a new generation of entrepreneurs”

Q How do you respond to that? Like, I honestly, I'd love to hear how you bring yourself back and re-repeat it. Do you know what I mean? Not re-repeat it, but kind of just bring yourself up from the ashes.

A Well, I think it's, it's really sitting down with the founders and encouraging them to find their own personal balance. And that can be different for everyone. You know, they need to have and understand that life is not just their startup. If they believe that, then eventually they will burn out. They have to figure out what are the two or three things that they must do every week in order to feel as though they got a proper balance of both work and personal life. And that can be different for everyone. For me, I'll tell you, it was going to the gym three times per week. So, you know, for me, I was making sure Monday, Wednesday, Friday, I would carve out some time during the work day and go out and hit the gym for an hour, hour and a half and sit in the sauna for And that reset allowed me to be more productive. It would allow me to, you know, I'm not, I'm not talking, I'm not talking about, you know, working four hour days here. We're still all working very hard. It's just really finding downtime to, to oftentimes let your, your mind just have a moment of silence. And I find that that allows me to be more creative. If I'm constantly going and constantly being strung out on caffeine and working until two or three in the Functioning optimally. And I feel like that is going to hurt my creativity longterm.

AI assessment note: “For me, I'll tell you, it was going to the gym three times per week.”

Q failure is removed from the equation, it becomes an element of comfort replacing it, and that failure actually drives you to work until three a.m. to ship product, or three a.m. to hit the right go-to-market strategy, or whatever it is. Do you know what I mean? Do you, do you agree with that, that the removing the failure actually does not bring comfort, but just brings comfort? Potential success.

A I think of it in a different way. I've, I've changed my opinion on this over the years. I think that, you know, certainly there is a healthy amount of drive that you need, and so you can't become truly passive, and you need to understand that it's important to have that internal feeling and drive to win, but I, I really believe that if you're burning the kind of midnight oil, and you're staying up, and you're pushing your entire team extremely hard, it's okay to do that in very small, small Sprints, but I don't believe that is taking the long-term view. I think that I want my founders not thinking about how they can win over the next three, six, nine, 12 months, but how they can really dominate over the next decade, and I think that you, we have to realize that it's okay to jog sometimes, it's okay to sprint sometimes, but you really have to be playing the long game here, and it can't be just about hustle twenty-four-seven. You need to find balance, otherwise you're going to burn out, and when you burn out, that is the worst Possible position that you can be in.

AI assessment note: “I think of it in a different way. I've, I've changed my opinion”

Q Do you find it concerning in terms of kind of the, the lack of distribution channels that are available to, to up and coming startups that maybe were available?

A I think, I think they're getting better. I think they're, I think distribution is getting easier with smart recommendations. So I'll, I'll give you a couple examples. Like there, there's two things that fascinate me. So one is the recommendations that are happening now on Instagram. So if you go, go over to the, the discover tab, so magnifying glass icon, second one over, you'll notice that The recommendations there for accounts to follow, and I'm not sure, I'd have to talk to Kevin about what's going on behind the scenes there in terms of machine learning or what they're using for, for the recommendations, but they have just improved so much in terms of getting the right content in front of the right eyeballs. So much so that it is very, very, very specific now around the types of content that you like and making those recommendations. I'll give you an example. So this is very, very niche, but it shows you like the power of niche actually is Is increasing. So I was recently affiliated and worked with Hodinkee, which is, you know, one of the biggest watch.

AI assessment note: “I think distribution is getting easier with smart recommendations.”

Q In terms of kind of how do you time the market and approach the timing of the market element?

A Well, uh, you know, in, in terms of public markets, it's just kind of dollar cost averaging in over time. So I'll pick a window of time. I'll pick a certain number of dollars and then I'll, they'll average in through a, you know, a weekly or daily investment depending on what's going on. But I, I have different buckets of risk. So for me, the kind of like early startup stage is just insanely risky class of investments, and so I have no problem going into some of the cryptocurrencies. I look for brilliant entrepreneurs. I look for not just clone products, but a true unique advantage, meaning that like, you know, I'm not going to buy into a cryptocurrency that is just a somewhat slightly version or somewhat slightly tweaked version of Bitcoin. It has to be something that is truly novel and unique, and so I'm When I'm getting into those markets, I'll, I'll place kind of smallish bets initially, and then as I see progress, continue to increase those over time. And that's part of the reason why I go for pro rata rights as an angel, and oftentimes push for kind of a super pro rata come the next round of funding.

AI assessment note: “in terms of public markets, it's just kind of dollar cost averaging in over time”

Q failure is removed from the equation, it becomes an element of comfort replacing it, and that failure actually drives you to work until three a.m. to ship product, or three a.m. to hit the right go-to-market strategy, or whatever it is. Do you know what I mean? Do you, do you agree with that, that the removing the failure actually does not bring comfort, but just brings comfort? Potential success.

A I think of it in a different way. I've, I've changed my opinion on this over the years. I think that, you know, certainly there is a healthy amount of drive that you need, and so you can't become truly passive, and you need to understand that it's important to have that internal feeling and drive to win, but I, I really believe that if you're burning the kind of midnight oil, and you're staying up, and you're pushing your entire team extremely hard, it's okay to do that in very small, small Sprints, but I don't believe that is taking the long-term view. I think that I want my founders not thinking about how they can win over the next three, six, nine, 12 months, but how they can really dominate over the next decade, and I think that you, we have to realize that it's okay to jog sometimes, it's okay to sprint sometimes, but you really have to be playing the long game here, and it can't be just about hustle twenty-four-seven. You need to find balance, otherwise you're going to burn out, and when you burn out, that is the worst Possible position that you can be in.

AI assessment note: “it can't be just about hustle twenty-four-seven. You need to find balance”

Q What was the point when you realized that it was actually something you wanted to do far more than just a hobby as an angel investor, but as a, as a VC?

A Yeah, I think that it started off, like you said, as, as just a hobby, and I never really thought about becoming a full-time VC. For, for me, as an angel, it was a way to support friends, to back what I thought were really novel ideas that, that could change the world, hopefully. But it wasn't until I made the move to Google that Where I met Bill Maris over there that ran Google ventures that he kind of got me excited about the opportunity of becoming a full-time VC because I was already doing angel investing anyway. And when I first started, started investing, when I say angel investing, I don't mean the types of investments that you hear typical angels do. Like for me, I didn't, I didn't really have any money. So, so it was a challenge. It was a, it's a challenge to be an investor when you don't have any money. So, you know, it started off by, I did a couple little advisory roles, um, You know, I did one at NG MoCo, um, which I was just helping out on the product side that eventually was sold for a couple hundred million dollars. And, you know, it's, it's all about taking these little wins and rolling that money back into real angel investments. So eventually I was able to make, you know, smaller little 10,000 dollar investments. And then eventually kind of the 25 to 50,000 dollar investments that you see, uh, angels doing today. But it's kind of, uh, it's very risky at that …

AI assessment note: “wasn't until I made the move to Google that Where I met Bill Maris”

Q In terms of kind of how do you time the market and approach the timing of the market element?

A Well, uh, you know, in, in terms of public markets, it's just kind of dollar cost averaging in over time. So I'll pick a window of time. I'll pick a certain number of dollars and then I'll, they'll average in through a, you know, a weekly or daily investment depending on what's going on. But I, I have different buckets of risk. So for me, the kind of like early startup stage is just insanely risky class of investments, and so I have no problem going into some of the cryptocurrencies. I look for brilliant entrepreneurs. I look for not just clone products, but a true unique advantage, meaning that like, you know, I'm not going to buy into a cryptocurrency that is just a somewhat slightly version or somewhat slightly tweaked version of Bitcoin. It has to be something that is truly novel and unique, and so I'm When I'm getting into those markets, I'll, I'll place kind of smallish bets initially, and then as I see progress, continue to increase those over time. And that's part of the reason why I go for pro rata rights as an angel, and oftentimes push for kind of a super pro rata come the next round of funding.

AI assessment note: “in terms of public markets, it's just kind of dollar cost averaging in over time”

Q Do you find it concerning in terms of kind of the, the lack of distribution channels that are available to, to up and coming startups that maybe were available?

A I think, I think they're getting better. I think they're, I think distribution is getting easier with smart recommendations. So I'll, I'll give you a couple examples. Like there, there's two things that fascinate me. So one is the recommendations that are happening now on Instagram. So if you go, go over to the, the discover tab, so magnifying glass icon, second one over, you'll notice that The recommendations there for accounts to follow, and I'm not sure, I'd have to talk to Kevin about what's going on behind the scenes there in terms of machine learning or what they're using for, for the recommendations, but they have just improved so much in terms of getting the right content in front of the right eyeballs. So much so that it is very, very, very specific now around the types of content that you like and making those recommendations. I'll give you an example. So this is very, very niche, but it shows you like the power of niche actually is Is increasing. So I was recently affiliated and worked with Hodinkee, which is, you know, one of the biggest watch.

AI assessment note: “I think they're getting better. I think distribution is getting easier with smart recommendations.”

Q No, absolutely. I think Naval Ravikant mentioned that on the show is one of his favorites too. I'd love to hear though your biggest mentor and how did that relationship come about?

A Oh, wow. Biggest mentor. I've had a few over the years, and I think part of the reason I do that foundation podcast is to really kind of pick the brains of those people that I really respect. Certainly, Bill Maris over Google Ventures and Tony Conrad has been another one and helped me think through some of the issues around how to deal with certain issues around management of employees. Also, Ben Horowitz, when I was going through a lot of the dig layoffs and the kind of transition and the hard times at dig, you know, I would sit down with him in his office and he would It's been a ton of time, even though they had just a few dollars, well, not a few dollars, but very few dollars, um, invested in dig, uh, the amount of time that he dedicated to help me out and think through some of these scenarios and outcomes for dig was just really helpful. So I've, I've had a, I've had a few, but I, I tend to be one of these people that I have a question about something and I'm, I'm not sure how to approach something. I try now to go and seek out advice and, and try and find the right person. So I I'll ping a variety of different people and say, you know, who do you know that's the best speaking coach, or who has done this well, and, and, and, you know, I have a handful of trusted friends that can generally point me in the right direction, but I think that the hardest thing for anyone is rea…

AI assessment note: “Certainly, Bill Maris over Google Ventures and Tony Conrad has been another one”

Q What was the point when you realized that it was actually something you wanted to do far more than just a hobby as an angel investor, but as a, as a VC?

A Yeah, I think that it started off, like you said, as, as just a hobby, and I never really thought about becoming a full-time VC. For, for me, as an angel, it was a way to support friends, to back what I thought were really novel ideas that, that could change the world, hopefully. But it wasn't until I made the move to Google that Where I met Bill Maris over there that ran Google ventures that he kind of got me excited about the opportunity of becoming a full-time VC because I was already doing angel investing anyway. And when I first started, started investing, when I say angel investing, I don't mean the types of investments that you hear typical angels do. Like for me, I didn't, I didn't really have any money. So, so it was a challenge. It was a, it's a challenge to be an investor when you don't have any money. So, you know, it started off by, I did a couple little advisory roles, um, You know, I did one at NG MoCo, um, which I was just helping out on the product side that eventually was sold for a couple hundred million dollars. And, you know, it's, it's all about taking these little wins and rolling that money back into real angel investments. So eventually I was able to make, you know, smaller little 10,000 dollar investments. And then eventually kind of the 25 to 50,000 dollar investments that you see, uh, angels doing today. But it's kind of, uh, it's very risky at that …

AI assessment note: “it wasn't until I made the move to Google that Where I met Bill Maris”

Q No, absolutely. I think Naval Ravikant mentioned that on the show is one of his favorites too. I'd love to hear though your biggest mentor and how did that relationship come about?

A Oh, wow. Biggest mentor. I've had a few over the years, and I think part of the reason I do that foundation podcast is to really kind of pick the brains of those people that I really respect. Certainly, Bill Maris over Google Ventures and Tony Conrad has been another one and helped me think through some of the issues around how to deal with certain issues around management of employees. Also, Ben Horowitz, when I was going through a lot of the dig layoffs and the kind of transition and the hard times at dig, you know, I would sit down with him in his office and he would It's been a ton of time, even though they had just a few dollars, well, not a few dollars, but very few dollars, um, invested in dig, uh, the amount of time that he dedicated to help me out and think through some of these scenarios and outcomes for dig was just really helpful. So I've, I've had a, I've had a few, but I, I tend to be one of these people that I have a question about something and I'm, I'm not sure how to approach something. I try now to go and seek out advice and, and try and find the right person. So I I'll ping a variety of different people and say, you know, who do you know that's the best speaking coach, or who has done this well, and, and, and, you know, I have a handful of trusted friends that can generally point me in the right direction, but I think that the hardest thing for anyone is rea…

AI assessment note: “Bill Maris over Google Ventures and Tony Conrad has been another one”