The Exchanges

Q Now, I'd love to dive into a snapshot of your background prior to starting your AngelList syndicates. So, so can you tell us a little bit about you and your history?

A Sure. I'm sort of a classic Silicon Valley guy. I'm a engineer who's always been tinkering and starting companies and, uh, Then was one of the early folks at eBay where I learned how to sell beanie babies on the internet. Spent eight years at eBay running various different functions and groups as the company grew from about a hundred people when I joined to about 15,000 when I left. After eBay, I ran a spinoff of Wikipedia called Wikia, uh, which is now a large consumer content site. Left Wikia and worked with a friend of mine to help start Fastly and Then in my spare time, I was, you know, through all of this, I've been an angel investor, basically as a way to connect to Young people who are trying to do interesting things.

AI assessment note: “Spent eight years at eBay running various different functions and groups as the company grew”

Q Now, I'd love to dive into a snapshot of your background prior to starting your AngelList syndicates. So, so can you tell us a little bit about you and your history?

A Sure. I'm sort of a classic Silicon Valley guy. I'm a engineer who's always been tinkering and starting companies and, uh, Then was one of the early folks at eBay where I learned how to sell beanie babies on the internet. Spent eight years at eBay running various different functions and groups as the company grew from about a hundred people when I joined to about 15,000 when I left. After eBay, I ran a spinoff of Wikipedia called Wikia, uh, which is now a large consumer content site. Left Wikia and worked with a friend of mine to help start Fastly and Then in my spare time, I was, you know, through all of this, I've been an angel investor, basically as a way to connect to Young people who are trying to do interesting things.

AI assessment note: “Then was one of the early folks at eBay where I learned how to sell”

Q And why did you go for the multi-syndicate model then? As you said, IOT, fintech, SaaS. Why did you choose that over one large, large syndicate?

A Yeah, I, I guess I look at what works in related industries, and I try to see if those patterns replicate, and in this case, the related industry would be, you know, the mutual fund industry. If you look at a Fidelity or Vanguard investment company, they don't just have one fund, like the S&P, 500 fund. They believe consumers should have choice, and the different consumers have different theories about what's going to do well, so You know, when I go to Fidelity, I can also invest in enterprise versus consumer versus utilities. Um, I can invest in, you know, Southeast Asia versus a Euro fund, and so we're really trying to give consumers on AngelList, you know, the, the other Angels, A choice in where to put their money, and, and that seems to work, right? They're very different people in the fintech syndicate than there are in the edtech syndicate.

AI assessment note: “we're really trying to give consumers on AngelList, you know, the, the other Angels, A choice”

Q And do you, do you see that vary? I mean, what's your probably most, uh, popular occupation invested in your syndicate? So they entrepreneurs themselves? Is it, uh, startup employees?

A Yeah, I'd say about 30% are in a entrepreneurial venture. They're either a founder or, or, Executive at an early stage company. Another 30 or 40% are more broadly working in technology, whether that's, you know, IBM and Accenture or, or Dell or, you know, bigger companies like that. And then there's another 30 or 40% that are just people who want to be part of the revolution all over the world. Doctors and dentists and private wealth managers and Yeah, I think the only thing they seem to have in common is an interest in business, and in many cases, someone who owns their own business or, you know, is an equity owner in a business. So, ownership seems to be a common theme.

AI assessment note: “30% are in a entrepreneurial venture”

Q This Week in Startups, um, you said with regards to deal flow that you don't see deals until they're pretty much done nowadays. And you said your job's to convince people to give you their money instead of VCs in blue jackets. So, what's included in your cell then? How do you convince people to give you money, and what's been the driving force behind your huge success in it?

A Well, I, I honestly don't think we convince people to give us money. We invest in startups that we think are very exciting, and that have a lot of potential, and either have, you know, great teams, great traction, or very disruptive ideas, and then we offer to let Our friends co-invest with us, and no one's obligated to, and we share information so people can understand why we're doing what we're doing, and if you think about it, every investment has a cap of 99 people who can invest, and we have about 3000 backers across the portfolio. So really, you know, on any one deal, only three percent of the people are able to invest, and I often find that, if anything, I tend to get complaints from people that they Weren't able to get into the deal they wanted to get into. So we're trying to think about ways to fix that.

AI assessment note: “I, I honestly don't think we convince people to give us money.”

Q And do you, do you see that vary? I mean, what's your probably most, uh, popular occupation invested in your syndicate? So they entrepreneurs themselves? Is it, uh, startup employees?

A Yeah, I'd say about 30% are in a entrepreneurial venture. They're either a founder or, or, Executive at an early stage company. Another 30 or 40% are more broadly working in technology, whether that's, you know, IBM and Accenture or, or Dell or, you know, bigger companies like that. And then there's another 30 or 40% that are just people who want to be part of the revolution all over the world. Doctors and dentists and private wealth managers and Yeah, I think the only thing they seem to have in common is an interest in business, and in many cases, someone who owns their own business or, you know, is an equity owner in a business. So, ownership seems to be a common theme.

AI assessment note: “about 30% are in a entrepreneurial venture. They're either a founder or”

Q So at five times cash on cash performance on your angel investing, you could have raised these started your own VC fund. Why did you choose to go down the angel this syndicate route?

A Yeah, it's an interesting question, right? I, I mused on venture a couple of times. Basically, I think I, I approach the world too much as an entrepreneur and, and not enough as an investor, to be perfectly honest with you. You know, I get excited about the idea and then I get a lot less excited about negotiating annoying terms and things like that, which is sort of the primary VC profession, it seems. I never really wanted to do a full-time angelist is this great sort of happy medium where you're working with entrepreneurs, my fellow investors, the backers of our syndicate to fund, you know, small checks, a hundred grand to a couple of million dollars to other entrepreneurs. And so it's really more of a community. Of people helping people than it is professional financiers trying to make money for, you know, Oxford and Harvard and Princeton's endowments.

AI assessment note: “I approach the world too much as an entrepreneur and, and not enough as an investor”

Q So at five times cash on cash performance on your angel investing, you could have raised these started your own VC fund. Why did you choose to go down the angel this syndicate route?

A Yeah, it's an interesting question, right? I, I mused on venture a couple of times. Basically, I think I, I approach the world too much as an entrepreneur and, and not enough as an investor, to be perfectly honest with you. You know, I get excited about the idea and then I get a lot less excited about negotiating annoying terms and things like that, which is sort of the primary VC profession, it seems. I never really wanted to do a full-time angelist is this great sort of happy medium where you're working with entrepreneurs, my fellow investors, the backers of our syndicate to fund, you know, small checks, a hundred grand to a couple of million dollars to other entrepreneurs. And so it's really more of a community. Of people helping people than it is professional financiers trying to make money for, you know, Oxford and Harvard and Princeton's endowments.

AI assessment note: “I approach the world too much as an entrepreneur and, and not enough as an investor”

Q And why did you go for the multi-syndicate model then? As you said, IOT, fintech, SaaS. Why did you choose that over one large, large syndicate?

A Yeah, I, I guess I look at what works in related industries, and I try to see if those patterns replicate, and in this case, the related industry would be, you know, the mutual fund industry. If you look at a Fidelity or Vanguard investment company, they don't just have one fund, like the S&P, 500 fund. They believe consumers should have choice, and the different consumers have different theories about what's going to do well, so You know, when I go to Fidelity, I can also invest in enterprise versus consumer versus utilities. Um, I can invest in, you know, Southeast Asia versus a Euro fund, and so we're really trying to give consumers on AngelList, you know, the, the other Angels, A choice in where to put their money, and, and that seems to work, right? They're very different people in the fintech syndicate than there are in the edtech syndicate.

AI assessment note: “we're really trying to give consumers on AngelList, you know, the, the other Angels, A choice”

Q This Week in Startups, um, you said with regards to deal flow that you don't see deals until they're pretty much done nowadays. And you said your job's to convince people to give you their money instead of VCs in blue jackets. So, what's included in your cell then? How do you convince people to give you money, and what's been the driving force behind your huge success in it?

A Well, I, I honestly don't think we convince people to give us money. We invest in startups that we think are very exciting, and that have a lot of potential, and either have, you know, great teams, great traction, or very disruptive ideas, and then we offer to let Our friends co-invest with us, and no one's obligated to, and we share information so people can understand why we're doing what we're doing, and if you think about it, every investment has a cap of 99 people who can invest, and we have about 3000 backers across the portfolio. So really, you know, on any one deal, only three percent of the people are able to invest, and I often find that, if anything, I tend to get complaints from people that they Weren't able to get into the deal they wanted to get into. So we're trying to think about ways to fix that.

AI assessment note: “I honestly don't think we convince people to give us money.”

Q And again, I'm gonna quote your interview with Jason, where you said together that you like to shit on VCs because it's fun, but, but you did say you were, but, but, But you did say you work with some. I'm adding that as a caveat. Uh, so who do you like to work with, and what makes a good VC for you?

A So again, I, I approach the world as an entrepreneur, right? And when I'm out fundraising, I meet with a lot of VCs, and, and honestly, there are a lot of good ones. The, the challenge is, Part of the VC sales pitch is they say they want to help, and so every meeting you'll take, they'll talk about, you know, hey, let me help you with this, or let me do this introduction, or let me get you this information that might be helpful for you. I always find the meetings are awesome. And I walk away all excited about the help I'm going to get. And to me, the best VCs in the Valley will actually help with one of the three or four or five things they mentioned. And a lot of VCs, you know, I'll send them a note afterwards and say, hey, uh, you know, can we follow up on these three things you mentioned? You know, the average VC ignores that email because they were selling, they weren't actually promising, you know, and the worst VCs will actually just tell you like, no, I'm not going to help. Like, You know, once I, once you let me invest, I'll help. But until then, I'm just, I was just storytelling.

AI assessment note: “the best VCs in the Valley will actually help with one of the three”

Q And again, I'm gonna quote your interview with Jason, where you said together that you like to shit on VCs because it's fun, but, but you did say you were, but, but, But you did say you work with some. I'm adding that as a caveat. Uh, so who do you like to work with, and what makes a good VC for you?

A So again, I, I approach the world as an entrepreneur, right? And when I'm out fundraising, I meet with a lot of VCs, and, and honestly, there are a lot of good ones. The, the challenge is, Part of the VC sales pitch is they say they want to help, and so every meeting you'll take, they'll talk about, you know, hey, let me help you with this, or let me do this introduction, or let me get you this information that might be helpful for you. I always find the meetings are awesome. And I walk away all excited about the help I'm going to get. And to me, the best VCs in the Valley will actually help with one of the three or four or five things they mentioned. And a lot of VCs, you know, I'll send them a note afterwards and say, hey, uh, you know, can we follow up on these three things you mentioned? You know, the average VC ignores that email because they were selling, they weren't actually promising, you know, and the worst VCs will actually just tell you like, no, I'm not going to help. Like, You know, once I, once you let me invest, I'll help. But until then, I'm just, I was just storytelling.

AI assessment note: “to me, the best VCs in the Valley will actually help”