This Week in Startups - E35: “Angel” Podcast: Sarah Tavel, Partner at Benchmark shares insights on getting recruited by Peter Fenton, disrupting VC gender norms from the inside, transitioning from operator to investor & more

Episode Date: February 26, 2020

0:50 Jason intros Benchmark's Sarah Tavel 1:20 Aside from Slack, what other companies grew like consumer-facing but charge like enterprise? 3:19 How was Sarah recruited to Benchmark? How is Benchmark different from other major VC firms? 12:04 Limited upside of talking to the press in 2020 17:30 Growing up in NYC and going to Harvard 21:30 Jason on becoming a "Don't touch the thermostat" dad 23:58 How did the offer from Peter Fenton go down? What drew Sarah to Benchmark? 28:36 Sarah's thoughts on disrupting VC as a woman from the inside & from the outside 37:30 How going from operating to investing is trading stress for anxiety 40:51 Jason and Sarah discuss their most personal & significant investments: Calm & Pinterest 47:26 How Pinterest's business model was a mold of Facebook and Google 49:45 Jason tells regulators how to stop Google 58:14 Investing in Chainalysis & Crypto infrastructure 1:12:44 Are the best companies polarizing? 1:16:30 Investing in Hipcamp 1:29:43 Marc Andreessen asks Sarah a question

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For trips of 30 days or more, stay with Zeus for beautiful, thoughtfully furnished housing. Go to zeusliving.com slash angel for $200 off your first booking. Hey, everybody. Welcome to Angel the podcast. This is episode four of season three. And we are cooking with oil. The guests have been transcendent. and people are just raving about the Dan Rose episode. I think you're going to love today's as well.

We've got somebody who has worked at what most people would consider two of the top 10 venture capital firms here in Silicon Valley Greylock and now benchmark. And we're going to talk about Sarah Travel's transition from one of those firms to another and her focus on consumer. You're a consumer investor mostly. Yeah, I mean, marketplace. Nowadays, yeah, a lot of marketplaces, B to B, B to C. and then nowadays you can't ignore SaaS if you're doing actually consumer investing I mean a user as a consumer at the end of the day and so it feels like the two things are starting to overlap a bit Slack feels like a consumer product but Slack is a enterprise company business yeah go to market motion go to market motion yeah what does that mean well just you know it a lot of it depends on how these companies will first get adopted and then

And second, how do they get paid to do that work? And so the go-to-market motion just means that there's a salesperson at the end of the day who's making a phone call probably and talking to someone about the benefits of paying for Slack. Right. And it starts typically without a salesperson. Correct. Yes. And then at some point, what, 10, 50 users, they get a phone call? Or an upsell?

Yep. Who knows? Yep. But that was the first company, I think, that grew like a consumer company while having, the revenue model of enterprise. Is that accurate? Or can you think of another one that did that?

Well, I would think, I mean, Yammer preceded Slack. And I think a lot of that was a similar story of the kind of bottoms up adoption. And look, Slack isn't the only one, Dropbox. Did that go to Market? Yeah, Dropbox would be actually the one that makes sense. But did they ever really go Enterprise? They never worked for them?

They certain, like, they, I remember, I don't remember how many years ago, probably two or three years ago, they hired a real head of sales, like kind of the person that you'd expect to make those big phone calls and get those big contracts. And so they went real into it. And I think to have done a really good job executing on that. And when you look at marketplaces, let's start there. Why are VCs obsessed with marketplaces? Obviously our mutual friend or your colleague, my friend, Bill Gurley, who I think you work pretty closely with? Yes. Was he the one who recruited you? It's a team effort. That's what, that's the stock bench. It's so true.

I cannot. Who made the first phone call and said, hey? That was Peter. Oh, really? Yeah. Really? Yeah. And how does that go?

Hey, we're the Yankees. You're kind of on the Mets or, you know, whatever it is. Like, hey, Greylock's a good firm. But anybody in the industry would say benchmark is a better firm than Greylock. You're not going to say that. I will. They're very, they are. They have better performance.

They're very different firms. They're structurally very different. How so? Well, one of them, you know, Greylock has taken the approach that most venture firms have done right now, which is they've pursued a bigger fund, a platform team. You know, they probably had the best talent team in the Valley when I was there with Jeff Markowitz and Dan Portillo and then an amazing marketing partner, associates, principal, senior partners, junior partners, but it's a way of scaling what they do.

Yeah. And benchmark, we've taken the approach of not scaling what we do because we don't believe it scales. Right. To do early stage venture investing. And benchmark was very intentionally built. And we've had Andy Radcliffe on the podcast three times, four times now. Yeah. One of the most loved guests on the podcast.

And they set up that specific firm to be equal. Yes. So if you come in and you've got five years experience and Bill, has got 20 and Andy's got 30, whatever it is. Everybody gets an equal slice of the pie. Greylock, not like that. Not at all. Right. That's part of the difference. But it's not just a compensation thing, although that's what it, that's kind of the way you reduce it from the outside is that it is. But what happens, what you feel when you're on the inside is that it's actually the culture of the firm and the organization of the firm, which makes a really big difference

when it comes to both, you know, deciding on new investments and then also support. pouring the investments that we've already made. So most venture firms have a hierarchy. There are senior partners or there are principals, associates, all this kind of stuff. Benchmark just said, hey, we're going to have six partners. It's five right now. Five partners. And everybody has an assistant, maybe?

That's right. Kind of old school. But no big, giant associate principal pool. Correct. Or a talent team. Or a talent team. marketing team, all this like extraneous stuff that Andrescent Horowitz threw into the mix. Yes.

And we believe we can't delegate any part of our job. Can't delegate any part of your job. That's fascinating. Yeah. So it's the job of that singular board member to help recruit. Correct. Yeah. The way I think about is most of the platform stuff that other people had, and I benefited from this and felt this when I was at Greylock, is really about scaling the GP. It's not about scaling the founder. And so what we do, the work that we do is like, we believe that in order to find, you know, help a CEO find the best CRO, I can't kind of throw that

over the fence to a talent team. Right. And then have that talent team, talk to the CEO, generate a list of candidates, talk with those candidates, and then play this game of telephone between me talking with the talent team, then talking to the talent team, then talking with the CEO, the CEO talking with me, then talking to the talent team. And instead, I have to be the person that's doing all those calls with you that's, you know, as much mind-melded with you as possible. Right. So that we find the best person because... More efficient. It's more efficient. And we actually think you get to a better outcome because we're as much on the same page as we possibly could be. It also shows a level of dedication to the founder and company that delegating

doesn't. That's, yeah, that's the way we think we can be the most effective at our job. Right. But from the other side of the table as a founder, if Bill Gurley's like, well, I'm going to go find that CMO and I'm going to do it. That's my girl impersonation is ridiculous. He has about 5% of that's why he. That's what we do at the poker table and Bill's making a decision.

I love it. Well, I guess I'm all in. But Bill Gurley says, I guess I'm all in and he puts those chips in, you're, effed. Just public. I don't mean to unlock Bill Gurley's game. I believe it. But when he says, I guess I'm all in, that's literally like Doyle Brunson or, you know, like John Wayne stepping on to the, you know.

He's never bluffs. No, he's got some bluffs in him. He's added bluffs in the later years. He added some bluffs. But if he's going to do a bluff, I would say it's probably going to be what we call in the business, a semi-bluff. He's got a, maybe he's got a flush straw, but he's got like a pair, but or mid, you know, bottom pair plus a flush draw. So, you know, he's going to have some.

He's not reckless. He's not reckless. Yeah. Absolutely. As opposed to Shamath, super reckless. Reckless, kind of his best attribute is a little recklessness. So Peter Fenton calls. How does that happen?

He texts you, hey, call me, or he emails him. He says, can we set up a call? How does that go down? Well, Scott Belski introduced me. Okay. And it was, look, like it. Explain what Scott Belsky is. So Scott Belsky was, at the time, one of the general,

partners at Benchmark. He had been a founder of a company called B. Hans and an angel investor in Pinterest, which I got to know him through that, just and just an all-around great person. So he he just sent me an email. He said, hey, look, Peter is always looking to meet, you know, rising stars and venture and wanted to grab a coffee. And so, well, you know, you got that big smile on your face. You get that email. That's a great email. You get that email and you're not going to say, no, of course you're going to meet Pete. But it's a great email. It can't, yeah.

The great email. Yeah, of course. And when you read that email, do you say, they're recruiting me? Or do you say they're dipping their toe? What is your, when you talk to your friends or your spouse or whatever, or another or your mom and dad, I don't know who you talk to? He said, I got this email. It's interesting. What do you say?

Well, I didn't even, I didn't mention it to anybody at the time because I was, I'd been at Greylock for a year. I was pretty heads down at Greylock. And so I just kind of saw it as getting to know someone who I can learn from in the industry and then and just assume it that's all. You're being recruited for the Yankees. I got the feeling that this was just a getting to know you conversation. Got him. Like maybe this could be getting recruited to the Yankees in four years, but maybe not now. That's right.

You meet the team. One by one. One by one. Yeah. Takes a week or two? Oh, no. This is over the course of several months. You covertly meet the team.

You got to meet them in places where you're not going to get noticed. You can't go to the battery and have a meeting with these folks. You've got to do it on the DL. That's true. So you do these meetings just at like a coffee shop or you go to a Walmart and meet in the back by the butter. How does one do those covert meetings where you know that if people see you at the Rosewood, you're going to get a phone call from your colleagues or something? How do you do that? Where do those go down?

Yeah, they go down in conspicuous places. but it's not hiding. You're not, it's not a, it doesn't feel like you're hiding. Okay. So it's not like some American CIA. Correct. Yeah. Where you're dropping notes to each other and mailboxes.

I'll say that when it started to feel like more real was when we did dinners together. Oh. And that's when, you know, that's like, look, for benchmark and really for all venture partnerships, like you really are bringing on not just someone who, how they pick, but it's also a person who becomes part of the culture of your partnership, especially with a small group where each person's personality really does change the culture of the group. And so we had casual dinners to really get to know each other in that context.

And that's when you start to feel like, all right, well, let's find something a little bit more private. Right. You need a private room. Correct. Or they've got that triangle desk. That special desk. You know about the desk.

Of course I know about the desk. Come on. When we get back, we'll talk about it. It's a table, not a desk. table. That's true. I'm sorry. There's a table. We'll describe the table when we get back. You should have Peter on and he'll talk. He has a very nice. Monologue. Okay. Yeah. Peter's, we're trying to get Peter on the podcast like 20 times, but I think Peter's been beat up by the press and like, it's just like what I think he's

taking a couple shots here or there. And I think just, you know, when you start getting beat up in the press a little bit, like you just, what's the upside of coming on a podcast or talking to any press today for people like us? I agree with you on that point. Not relevant to Peter because I've never seen any bad stuff. And I think like Harry Stevings always talks about how the 2020 that he did, the 20 Minutes VC that he did with Peter's the number one downloaded podcast. Yeah, because Peter's podcast shy. Right?

It doesn't do a lot. Yeah, yeah. But the point you made about public figures having conversations, like it just feels like there's so much more to lose for people than to gain by talking to press. Yeah. There's a real thing there. It's, it's, there's a negativity in the press right now. There's, I think it's Twitter. You think it's attributable to Twitter. Yeah. Because Twitter, it's a, it's like, first of all, like the, the character restriction, the way that, you know, it's a headline and most people just read that and then reach, and how easy it is to retweet without any nuance.

It just, yeah, creates these flash mobs where people like, um, research. tweet content without ever reading. The actual story. The actual story. They read someone else's take on it, which is always biased. Yeah, hot take. Here we go. The hot take. And it creates this, like, terrible, like, mob effect that I think is, it's just really unfair and not the way humans should interact. I agree. And my thesis on podcasting and its ascension is for folks like us who are trying to discuss new. points, you cannot worry about me misquoting you. Right. I can't misquote you.

You can stop this interview at some point and say like, Jason, I think it's a silly question. Here's how I look at the world. Now, if you were to say, if I was a journalist, Jason back in the 90s and I said to you something, and you'd be like, that's a silly question. I mean, I really don't think that that's the right question. Here's how I look at the world. That phrase that I just said, that's on the cutting room floor. And then the next thing you say, or the thing you say that's more, you say, that's

most provocative is the lead. Right, right. Right. Yep. And that just devolves the trust between the subjects and the journalists, which is where we are today, is this completely gone adversarial. When we get back from this quick break, I want to know at the moment where the deal and the actual offer gets passed across the table from Axe Capital to you, right?

And Axe slides it over and Wiggs is in the room and Taylor. You watch billions. That's the best show. The greatest ever. We'll talk about our love of billions in segment three. So good. And then actually surprise for you. Mark and Drason heard you are on the call.

And I know that they tried to recruit you. He's going to just ask a question at the end of the pod. When we get back on Angelop Podcast. Hiring the right person is the major unlock for you and your startup. You know this. There are two things that you waste way too much time on. One is hiring people. Two is raising money.

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I do. Sarah Tavill. We both grew up in New York. I know. Interesting. I'm a kid from Brooklyn. I'm a Manhattan kid. You're an Upper West Side girl, huh?

We could have like maybe Lincoln Center. We could have both gotten off when I went to Fordham. Yeah. I went to Fordham at Lincoln Center at night. You went to Stuyveson. I did. Really hard to get into, but a public school. Yep.

Very diverse. Very vibrant. And when you went, it was on the West Side Highway. Correct? just opened? It had just opened, that's right. Way downtown in Manhattan. And when you went, they didn't have the bridge yet.

They put the bridge up later? They did have the bridge. The bridge went up. Yes, brand spanking new. Because that was the big issue. Kids were crossing the West Side Highway 12 lanes. And people, I don't know if it was a student, but somebody had gotten killed crossing the West. I remember that.

Yeah, it was really tragic. Then they built the bridge. And then the kids still would cross the West Side Highways. Kids are apt to do. Yes. But the bridge was a very good idea. Yeah. Yeah.

And Stuyveson on the West Side Highway there at that cafeteria looking out on the Hudson, I mean, it really is a special institution. Is it not? Yeah, it's a special institution. What was special about it? What was it like? I mean, honestly, I think the special thing was that the kids that were there were extremely driven. Yeah. Right kids driven. Yeah. It was like a very, you said diverse. It was very heavy on immigrants. So, I mean, a lot of, it. probably 60% Asian when I was there. A lot of Russian immigrants, a lot of people who, it was their shot at a really great education.

And I'd say like the teachers there were a mix. Like it's, you know, it's an intense public school where you have 34 kids in a class, eight classes a day. So it's still public school. Yes. So you have to make your opportunity. Correct. It's not like somebody's going to stop the class and be like, oh, sorry, you're a little bit behind.

Right, right, right. Pause the whole class. Yeah, it was a factory. It was a factory. And I, you know, honestly, by the time I got to college, it had kind of crushed the love of learning out. I mean, it took me a couple of years to, to rediscover that, yeah. Because it's just, you know, it's, it is the way that they did is like how much work can someone take. And that was the way, and that was the way that they would separate the, you know, the wheat from the trap.

Like, that was the way that they would really figure out who deserved the 95 or whatever. And it was just a very, very competitive school. Yeah, it was very competitive. I remember. I went to Survearian high school. Brooklyn. And we had some friends who, you know, went to public school in Brooklyn and then wound up in Stuyvesant. But that was the goal. Yes. Would you want to go to college? Harvard. You went to Harvard. Oh, my lord. Undergrad. And then MBA or no? No. Just went to work. Just went to work. I just want to make money.

You know what? That's refreshing. That's what I wanted to do. I was a kid from Brooklyn. And you know what I wanted? Yeah. Money and power. Yeah. You know why? Why? I didn't have it. Nobody had it. Yeah, yeah. Where I came from, nobody had money. Nobody had power. I knew one person who had a Mercedes, a doctor. I didn't care about power. I wanted money. I was a terrible student in college because I just worked. Really? What'd you do? I sold, you know, I did a bunch of things. I sold ads for a lot of publications. I started a house painting company that became a general contracting business. Like, I just did anything I could to make money. Where did that come from? What did mom and dad do that? Put that little fire in you. Or did you see like entrepreneurship up close or something? You know, my dad was always a really hard work. And so you definitely saw that model. And, you know, we were well to do, but there were definitely fights about money that you would, you know, you couldn't help. In my house. Yeah. I would say nine of ten fights my parents had, money.

I think that was for us too. Maybe eight out of ten. The other two of my dad having a couple too many drinks. Okay. Mine were religion. It was money and religion. Yeah. Yeah.

Absolutely. Yeah. And my parents had a very, very loving marriage. But, like, I remember my dad. dad getting mad at my mom about cereal, you know, and how much it costs. And so... What are we doing? There's 365 at Whole Foods and you're buying Captain Crunch.

We got the big jumbo ones that we go stale. This Costco. We could go to Costco. I'm turning... My mom would die if she heard this. I am literally... I'm 49 now. I'm older.

You're like 10 years younger than me. What are you 35? A little bit. Yeah, 10 years younger. I'm 38. You're 38. Okay. You look great. You look like you're 22.

I look like I'm 65. I don't know what happened. I look in the mirror. I'm like, wow, I'm turning my... I'm literally turning into, like, the classic dad. I'm like, who left the refrigerator open? The nest has eco mode for a reason. Do you not care about the planet?

You got the heat on 72 and the doors open. I live in Hillsborough. It's 70 degrees in Hillsborough. And if somebody puts the air conditioner on to 68 or they put it on to 72 to make it warm, I'm like, we're in Hillsborough. We're in Northern California. It's 70 every day.

You don't need to touch the thermostat. There's a sweater. That's the thermostat. You either put the sweater on or you put a t-shirt on. If you're hot, you take off your pants, you put on shorts. That's it. That's how heat works. Yep.

It's called clothes. But you got to burn oil. I'm literally going mental. There's something that happens when you have children and a family. You'll appreciate. My dad create, I have four siblings. He created an incentive system so that if we turned the lights off and we kept energy cost low, he would split the gain with us so that I was a person.

And we're wondering where you became love of entrepreneurship. He gave you a metric. Who would have thought? He gave you like, what do they call it? Like, at a startup, but we have a key metric. An OKR. He gave you an OKR. He's like, here's how your comp works.

Compensation system. Com for 20. Comp for 1998 is going to be based on. Yep. That's exactly what happened. Savings. Here we go. Me, touch his thermostat.

My dad within five months come running. There he goes. This is the great. greatest thing, though. I got my revenge. How? The Nest has an app. I open that app up sometimes. Yeah. I see what's going on with this thermostat in the middle of the day. You know what I do? You turn it down. Eco mode all thermostats. I can do it. Boom. All three thermostats are now in eco mode. Good. Go change them. Nobody else even logs into the Nest app. I know that. Nobody asked me for the password. And then people are like, what's going on with the heat? It's not working. My wife thinks sometimes that the nest is just flaky. I'm like, yeah, that nest, this bug reports all over the the internet. It's a great idea. I'm so glad you mentioned this. I just, that's what I say. I just

say, listen, you know, there's bugs. It's sometimes defaults back to Eco Mode. It's using AI. I told my wife this. Don't want to tell her on the show. Don't clip this. Don't tell your aunt. Neither of our parents are our families can watch this episode. So there's a moment where all of these dinners, whatever, three, four months in, where the actual offer happens. How does that go down? Is it a phone call? Hey, we want to make you a formal offer. Or somebody says they float it. So what are you thinking, Sarah? How do they actually put the offer on the table? Oh, you're really getting into it, aren't you? I think people are just curious on a mechanical basis, how it goes down. I mean, we get there's a

courtship, there's a bunch of meetings, there's checking out that the culture fits. Let's assume that's none. Is it like an official letter or is there just somebody going to walk with you and you're walking across? For me, it feels like an Embarcadero walk. You get somewhere on the ferry building, you hit the blue bottle, you get a little macchiato. And Bill Gurley says, so what do you think, Sarah? You want to join the team? That's my view of it. I'm thinking like Brian Cappellman on the billions. A nice, big vista, a little walk. You get the iconic espresso and it's in glasses, not paper. They put the espresso down. You walk away from the blue bottle. So what do you think, Sarah, cut. Let's go for the promo for next week. How close am I? You know,

the way it works well first of all the letter doesn't happens way after because the nice thing about an equal partnership is that there's not really a negotiation it's like one fifth yeah that's essentially what happens and so it really is this conversation at the end which you know i'll say kind of early on there was there was a point at which the one-on-ones had happened and then there was this point of like well we're we actually this is what this has been about like we want to have a conversation with you about potentially joining benchmark and just getting to know each other more. And at that point, I actually said no. What?

Well, I, you know, I was, I was at Greylock. For 12 minutes. Well, Greylock had been really good to me. And I felt like it wasn't, it didn't feel right. I wasn't ready. It just didn't feel right. Were you there for a year? I was there for, by the time I left, it was, yeah, a little over a year and a half.

Yeah. I mean, you're like old school like me. You want to put in four years. Yeah, I felt, I mean, more than four. years. When you join a partnership, it's more like a marriage. You know, the expectation was that if things work out for both of us, this is the last job that I'd have. And so there was something that really didn't feel right. And so I actually said no. We walked away. And then I ended up having a call with Rich Barton, who I had met through Cresaca, actually. Rich Barton had done Glassdoor.

He has done a number of companies. Expedia, Zillow, Glassdoor. He's a baller. He's like an operating machine, right? He's so freakishly talented and so many different dimensions, it'll make you angry. This is what I hear. Yeah. Producer Nick, lock it down.

I know. He's so good. Why is he not on the pot? And so what happened then is like he basically like, look, what do you have to lose? At the very least, it'll make you better at your job. And so, and there was some truth to that. Like, what did I have to lose? I was, if I got to know benchmark better, at the very least, I would learn how to do my job better within Greylock.

And so, tell me how the Yankees work. Yeah, no, that's exactly it. And so I, and it's one of those things that as I got to know benchmark, I just realized, it was like one of those things that once you saw it, you couldn't unsee it. That it was just, it felt like, oh, this is how it should be. This is how I want to like spend my career. And this is how I think I'll be best at what I do is working with these people and this structure. And so it was kind of this moment of realizing like, oh yeah, I, you know, I love Greylock. I love the team there.

But I really owe it to myself that I should explore this further. And then it got to a point where it just, the fit started to feel more and more strong through each of those interactions that we had until finally it was kind of this moment. moment of being like, all right, shall we do this? And the answer was yes. So they just said, should we do this? Basically. Wow. That's how you say. Should we do this? Yeah, kind of. I mean, you know, they had a much better, you know, benchmark knows how to close. And they had a much, they had a much better way of doing it. Really? I'll keep that one. Okay. Yeah. So they basically gave you their top ten list? Top ten reasons, right? Top ten reasons. Like the Letterman show. Number ten. One fifth. Just. Just.

Well, I mean, and also if you think about it as a woman adventure, you're the first female partner at benchmark. Is that right? Correct. And you think about this moment in time. I think you look at how much alienly, how much effort she had to put in over a decade or whatever. And all that work, all that fighting, you look at... who was the other partner, Kleiner, Ellen Powell. Oh, yeah. You look at all of the folks who came before you and fought their way through the industry when it maybe wasn't as easy for women and maybe actively hostile or even, you know, in Ellen Powell's case, obviously harassment.

And, you know, obviously shouldn't win the lawsuit, but there's some bad stuff that happened. So it was no perfect victims, but obviously there's bad stuff occurred. in a way, for me, it's almost like your, this latest stage of the venture capital firms, the elite ones, finally putting women as equal partners with checkwriting ability at equal economics. This is an important moment. Was that important for you in a way? Did you feel a sense of history or importance as a female in the industry or just think, listen, I'm a great player?

That's it. It's not about that. No, I think by that point, you know, I was the first female partner at Greylock as well. And so, well, and you know, and when I joined Bessemer, I was the first woman that they had hired in, I don't know, a decade or so. And so I, you know, at this point, I think like what it more felt to me is like there are, there are two ways to attack the problem of there not being enough women in kind of check writing venture roles. One of them, which is a path that I've chosen, is to try to, disrupt the hegemony from the inside. And the other path is what a lot of people have done very, very successfully, Aileen Lee, Kirsten Green, and others to create separate funds outside of that hegemony and then disrupt from the outside. And I think these two, that's like the combination of both is making a lot of change happen in the industry.

Do you feel any sense of I'm the only women in the room in these situations? I've never been as a white guy. in my life, I can I can count on like a small handful of times when I've been not the majority of the room. Yeah, yeah. In business. Certainly as a, you know, socially I've been, you know, the minority in the room on a demographic basis, gender basis, race basis. But in business, it very rarely happens. Yeah.

Well, when I started at Bessemer, so I was a year out of college, you know, I was new to the investing world, new to the technology world. I had been a philosophy major in college. Oh, really? And I was, you know, I was the youngest. I was the smallest. I was one of 25 and I was the only woman. I couldn't, it was my first experience of being the only woman, and I couldn't not feel it. You know, I felt like.

Yeah, 24 to 1 is, you know, 4% of the room being female is traumatic. And it wasn't, you know, it was, the room itself would be probably call it 15 people and there was other rooms. You know, it was all over video, but you would still feel your otherness. Because it was my first experience, I would say like, you know, that's, I joined, I joined Bessemer in 2006. So that was, and, you know, there were, the number of women VCs I could look to as role models was, I could count them on one hand. And all of them were on the West Coast. I didn't know any of them. I was in New York at the time. And so, like, as my career progressed, I, you know, it went from being, honestly, a daily struggle, like, something that just felt like, I, couldn't participate with, I just, I couldn't participate in the culture the way that the other, like my peers were, because I felt my otherness. But it's gotten to a point for me now where, and I think, you know, context is everything too, where I, like, I notice it sometimes, certainly, but it's not, it's more, more often than not, 98% of the time I don't notice it. And you know what?

And I'm assuming this and you can confirm it for me because I don't want to mansplain this, But I got to think, walking to a room, even at benchmark, which would be 20% female, which is a lot more than 2% or 4% as we just discussed in the room, knowing I am equal economically. Then that's got to take the edge off because everybody is making decisions and everybody's paper is the same. Yeah. Again, it's not about the, you know, there's, I kind of think. think of these systems as you have compensation, you have the organizational structure, and then you have the culture. And it's those three things I interplay that make you feel. I remember when I started at Greylock, I felt like, okay, I'm the new partner. I really got to build my credibility and like go up, you know, the rungs of a ladder of like what a GP is at Greylock. But when I started at

benchmark, you just from day one feel like an equal. And that's not a compensation thing that creates that because you don't feel that in the same way. It's, it's the culture of the people. And it's, you know, it is the, like, when it, well, I remember that there's a, we had to make a decision on something. And it was like having five CEOs on the phone at the same time. Like, you know, because there's no one person that makes a decision at benchmark. Like, there's, it's literally the five of us making a decision together, which means that we're terrible at operating benchmark. And we all, we're all doing what we do. because we want to invest, not operate.

But it just feels very different. When we get back on this quick break, I want to know why the decision, how the decision-making process works. If you feel passionately about an investment, you did Hip Camp, I believe? Correct. And we had the founder on the podcast.

She was amazing. Yeah, she was amazing. I want to talk about, like, when you're, what is the process of bringing that to the Yankees, right? Listen, this is a storied franchise benchmark at this point. And you're the new one and you're bringing something in and an idea. Was Hip Camp there or was that at Greylock? It was at benchmark.

I want to know what that was like. Was that the first deal you did? No, Chenelis was the first deal. Great. So I want to talk about when you bring those two deals specifically to the, how does it work when we get back on Angel of Pockets? If you're an accredited investor, you need to understand what an SPV is. That stands for special purpose vehicle.

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In fact, the first time I ever did one of these in SPV, you know what it was for? com.com, the meditation app. And that worked out really well. Yum-Yumski's thanks to Assure for powering my syndicate and for offering this discount to angel listeners. Okay, let's get back to this amazing episode. Sarah, Tavo is here. God, I said travel before, and it's only because I haven't been sleeping at night.

It's not easy. Yeah, you've been up to? I had one last night. Yeah, three o'clock? Two o'clock? That was what I was made between two and three. I was like, this is getting ridiculous. I'm up all night.

This Bloomberg and the debate got me. I know. I got two or three companies in crises at every given point time. and you can guess in from out of town. I just got everything going on at once. The job of a venture capitalist, there are some very anxiety-producing moments. Yeah, I always tell people

who are thinking of going from operating to venture that you trade stress for anxiety. You trade stress for anxiety. Explain the difference. Well, and when you're operating, you can control the outcomes, right? Like you feel the stress of, am I going to be able to execute?

Am I going to be able to get this done by this date? it's in your control and so you can stress about it versus what happens in venture is you don't really have any control, right? Like you're when you're looking for deals, you're just planting seeds and seeing what sprouts, you know, you don't really know where the next deal is going to come from. It's not an outcome that you necessarily can control. You can only control the inputs. And then with the companies that you work with, like at the end of the day, it's the CEO and the team that's running the race and you're on the sidelines trying to cheer them on and coach them. But your ability, you can't stress because you're not running it yourself.

You have the anxiety of, am I going to be all to influence them in the way that I think that they need, you know, could be useful. Right. So that they're able to be more successful in that race. So you have this like low grade anxiety that can just be like, oh. Yeah. You know, 12 months a runway, 10 months of runway, six months a runway. is this invalid, are they going to cut the burn or are they going to just keep racing towards

a cliff? There's, yeah. And you're like, hey, you want to pump the brakes? People are like, why would we pump the brakes? It's just the one that you had a 2.30 a.m. wake up about. At three of them at the same time. Yeah, yeah. When your portfolio gets large enough, just rule of big numbers, you're going to experience

at all. Oh, totally. And I'm currently, that's what it turns out late 2019 and 2020 is about. for me. Like make 200 investments over a decade. Yeah. Get ready. Yeah. Because all the stories you heard are going to be on your doorstep. And by the way, you're the highest profile and you're the first investor. So guess what? Your name is associated most with the company. So it's on you, not the other people who followed on who aren't on the board or aren't there. Yeah. It's, it's, my mom always, like, one of five and my mom always says that she's only as happy as her least happy child. And I feel that

with companies that, you know, you're always like, it doesn't, if the one that's, working, it's working. It's working. You know, and so you don't screw it up. You don't, yeah, I mean, you try to push more, but like at the end of the day, like, where your emotional energy ends up going is to the ones that are struggling. And so that's kind of the reality of the job. And it's, it's hard to see that because everybody's like, oh, you're in Uber, you're in

Robin Hood, you're in Com, whatever. Like, it's great. You know, and you're like, yeah, those are great. Yeah, they don't need me. They literally don't need me. Like, my phone calls with Travis. you know, for a large period of time, we're like, just, really? Like with Alex and Michael from Com, it's just like, really?

They're like, yeah, I'm like, wait, that's the monthly number or the quarterly number? That's the monthly number. Wait, there's more money in the bank account this month than there was last month? We're not, we have profits? I've never heard of that before. I'm like, wait a second, we're building up a war chest. I thought that was only for Apple. Like, what is going on here?

Good for them. for calm. Yeah, they've done an amazing job. It's, you know, I'm going to ask you this question as well, the most significant, like, um, company, not the most successful, but the one that makes you feel the most warmth. Warmth. Just warmth, like, just warms your heart kind of thing. And for calm, that's mine.

Because at some point the founders told me, we had met with like 70, 80 VCs and Westers, and they all said no. Got a couple of 25, 50K angel checks here and there from friends. What was one of them? I remember that. Yeah. No VC would give them the money they needed. And I had just, Naval had just given me the URL of Angel.com slash Jason slash syndicate. And he said, check this out.

And I said, well, and he explained it to me. Like, that's PV. And I'm like, what's an SPV? Special Purpose Vehicle? How does that work? I was like, all right, well, I'll just tweet it. So I tweeted it and like 300 people join my syndicate. Wow.

And then I told Alex to come. I was like, I had the syndicate. I'll put 50K in the round from my little $10 million micro fund. That's me and my poker buddies and friends. And I'll syndicate it. I think another 50 or 100 could come in. And 328,000 came in. It's first syndicate I ever did.

That's great. For $5 million post, I think. We owned 5% of the company. They said to me later, you know, we were going to shut the company. We're thinking seriously about shutting the company down if we didn't close that syndicate with you. And the fact that it overperformed and we got that money was the reason I'm still here. That's awesome. know if that's true.

Yeah. But the fact that they told me to me and they know the impact that has me, it makes me want to go to work every day. You have one of those? Sure. I mean, it's, and I don't. The warmth. I'm not choosing it because it was the highest profile one, but I feel that with Pinterest.

I mean, when I was, you know, we did the series A for Pinterest when I was at Bessemer. The Series A. Yes. And it was. For an image board. It was a, yes. It was a very, you know, it was a four or five person company at the time. Like it was misunderstood by everybody in the valley.

Like we, you know, I was an early user of the product. I just loved it from the first time I used the product. And I loved it so much. And I just was watching it on, you know, Alexa tracker, which was this, you know, it was a website at the time. Yeah. And just saw it keep on going up and keep on going up. And I just realized, like, this is the one.

and I thought it was the most competitive deal ever I just assumed that it was multiple term sheets and I went on to we invested in the series A and I ended up joining the company because I was so excited about it and at my going away party Ben confessed that we were the only term sheet and it was kind of a similar story

where it was just like they you know they had gone up and down San Hill Road that's um I mean who knows like I'm sure they would have found something somewhere. May not be where it is today. It was, I'll put it this way, which was that it was an important moment for the company at that time.

Right. Very important. And this is the time where you're the only woman in the room at Massimer, as we talked about before. And this is a product that is primarily used by women. Correct? 70%. At the time, it was even more so.

Yeah. Oh, yeah, because it's now become such an SEO juggernaut that so many people are winding up on it, that there's men. winding up on it, but maybe not going direct traffic. I wonder if the direct traffic still is 80% women. Probably not range. And this shows the real opportunity for having people different than a bunch of white dudes from Stanford. They didn't see it, did they?

It was the moment I realized. It was the first moment that I realized that being a woman could be an edge, you know? Because, like, in venture, you're always looking for your own unfair advantage. And your unfair advantage can come from the operating experience you have where you really understand a space. It can come from just diving deep and mapping out of space and understanding like all the players. It can come from just years and years of experience.

Or it can come from kind of your own experiences in who you are. And Pinterest was a product that none of the men got. I mean, Jeremy Levine at Bessemer did get it. Like I think he, I don't know if he got the product, but he got the metrics, which were the retention there was real. Undenial. It was undenial. I mean, there was 30,000 registered users at the time.

It was super early. Right. But like it was. The utilization per user. It was extraordinary. Yeah, yeah. The number of boards they created. And the repeat usage.

But, you know, everywhere else, like, it was one of those things where people just thought it was going to be a real niche site. Tell me about the fight to get it funded. Did the, Did you have to fight extraordinarily hard, or did they say, okay, you're at this enthusiastic, let's do it? No, it was, you know, I was lucky because I was working with Jeremy Levine. And so he, at that point, I mean, he'd already done, I think, LinkedIn and Yelp. And so he had the standing, yeah, yeah, yeah.

And so. User generate content was powerful. Yeah, and that was actually the thesis, which was that we had had, at Bessemer, a lot of success with user-generated sites, Yelp, LinkedIn. And social commerce was one of those spaces where I, you know, we had also done a bunch of companies in the commerce space diapers.com, which became quidsey, which got acquired by Walmart, Mark Laurie. And just really believed that, you know, there was going to be an opportunity for a company that was the intersection of UGC and commerce and was looking, looking for what that would be. And that's when, you know, I came across interest. I was on the board of this company called This Next at the time. Oh, yeah.

in L.A., Gordon Gould. And we would have these discussions, like, yeah, Pinterest is doing pretty good too. And it was really the same idea. There were like five or six social commerce. The fancy supply, the snacks, like there were a bunch. And they really had this fascinating moment because they were UGC, all of a sudden you had this flow through traffic coming from Google to the landing pages. And then if the landing pages had any kind of monetization on them, a Google ad that then took you to a search. ad, you all of a sudden were starting to monetize at this $25 to $50 CPM, RPM, whatever you were doing.

And it was like, wait, there's something here. Yeah. But they actually came up with their own, the sponsored pin. Yeah. When did they come up with that idea? And when your partners and when you were analyzing the Pinterest investment, this was an era of don't worry about making money and just get to scale. That's right. Correct.

When did the discussion? Because this has poisoned the mind of a lot of. founders, I believe. You don't have to worry about making money. Is that true? You don't have to worry about making, just worry about getting a lot of users. What's the truth in that?

And do people over index on that? Did they know what they were going to do as the model? Do they have the idea that it would be sponsored pins in the beginning? For the earliest days that I can remember, it was just obvious. I mean, you had, what Pinterest was, was the intersection of kind of two big companies. Google with like the discovery intent, search intent, and they had that first native ad unit, which was the, you know, the sponsored links.

Right. And we, you know, it made, like, the wonderful thing about sponsored links is that they actually made the search results better. Right. Because they're super high quality, like, it's only going to be a high quality company with a high quality landing page that's going to spend money to have that be, like, not going to be a spammer. That's correct.

And it's also, it's like conversion rates. take into account. So it creates a great experience. And so it always felt like, number one, there was going to be something like that for us at Pinterest where we would have a native ad unit that was going to be a sponsored pin that was actually going to create a better experience for the users than not having it. And then at the same time, we had an engagement mall that was more like Facebook, where we had people coming in and spending a lot of time on Pinterest in the same way that they'd spent a lot of time on Facebook, but no one spends time on Google as a very transactional system. And so we felt like we had that intersection that would create a really

big opportunity. That's fascinating, because Google, if they do their job correct, they get you off of Google very fast and you don't come back. If you come back, it means they failed. Right. At this point, Google has started to try to own the user more and more. And like, you know, the actual, when you do a search, you give you the answer. You have to. scroll down like 16 pages it feels like to get to the first link. It's so brutal. I mean, I think this is going to be their undoing with the Justice Department.

It's already happening in Europe, which is if any regulator, this is a message to regulators, I can tell you how to stop Google. I'm sorry, Sundar. If you want to understand how to stop Google, all you have to do is record, I'm looking into the camera here so you can make this

into a clip, record 1,000 users doing a Google search randomly selected. record their screen after they do 10 searches, then ask them, of the 10 links they picked, which ones were paid and which ones were not, they will not know. I would say 10 to 30 percent of users actually know if they clicked on an ad or not. In other words, 70 or 80 percent of the commerce going on on Google are users who are confused and don't know they clicked on an ad. and that is the mobile experience on Google. If you do a mobile search, forget about the web.

The web, they're kind of put the little tiny ad chicklet, but they are, Google is, I'll say it right here, and you don't have to say this because I know that you maybe want to have a relationship with them in the future, but I don't care. My brand is to not care. They are deceiving users at a scale that's never happened in advertising before. Is my theory right or wrong? I thought you said you weren't going to ask me.

Okay, I'm sorry. Does my theory, have you heard my theory before in the back halls of conferences and other people are afraid to say it publicly? Have you heard it come up before that Google is deceiving users at a mass scale and that most users don't know they're clicking on ends? I don't think I've ever heard that particular argument. What you do here and you just, you can't help but see it, is the fact that they just have this privileged position in their own search results.

And so anybody else that can participate in it just becomes pushed down more and more. And so it's not necessarily the best thing for the user either because I would much rather see a Yelp, you know, review and the. Yeah, then the FACCA. Then like whatever, yeah. Google. And it's like there's four reviews. And you're like, there's 4,000 reviews on Yelp. You tried to buy Yelp, Marissa.

You lowballed them. You insulted Jeremy. You didn't get it. And now you created this fight for life. Like they could have just been generous and let Yelp have a business and not push them down to the seventh or eighth click. That was some hardcore gangster stuff when they started what they did with Yelp. I think that was where they kind of opened themselves up to this massive criticism. When we get back from the final break, I want to talk about the two first deals you did.

Sure. At Benchmark. That was my teaser for the last one. but you told me about your time at Pinterest, which I also want to go deeper on. So we got to go deeper on Pinterest. Okay. We got to maybe finish up a little of the Google and maybe antitrust at the end of what should happen with these big companies because we all are faced with us with our portfolios. And then your first two deals into the partnership at Benchmark where you're an equal partner on the Yankees' top three firm.

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intelligent, insightful, and actually pretty funny, Sarah Tavel's on the podcast. Didn't expect that. You got a sense of humor. I was never expecting that either. You've got a sense of humor about you. You're pretty candid.

Now I know why they brought you in. You're candid. It's a blessing or a curse. I'm not quite sure yet. I think once in a while, your candidness as New Yorkers can get taken the wrong way here on the West Coast, correct?

You've had this experience where you're like, whoa, that was candid. But then somewhere in the fifth or tenth year being out here, you just know, keep it in fourth year, keep it in third year. People are just not ready for the New York bluntness. Like, when you're in New York and somebody's walking slow,

you're like, can you move? Oh, my God. Can you please move? I actually honk at people. I mean, the thing in New York, that's crazy, since we left, it's turned into... My wife kills me about it. It's turned into Paris.

Like, there's more tourists than New Yorkers, and they're all spinners. Yeah. They walk, they stop. Don't get me started. They look up and they start spinning around. Don't get me started. I'm like, this is not a pinball machine.

Get out of the way. If you want to stop and take pictures, we're trying to get to work. I fantasize about the fast lane and the slow lane. This has got to happen. They need to stay. up everybody who's a, if you're coming to New York. Jason, I feel like you and I have a connection here.

We do. We do. It's locked in as New Yorkers living in Cal. I drive like a taxi driver here. It's terrible. How many speeding tickets you get out here so far? No comment. I put the over under at three.

And I might take the over in that bed. No comment. I got three in three years. If you could get speeding tickets by walking on the sidewalk, I would be. Yes. I'd be in jail at this point. Like I am the fast. I have just, you know, always.

Yeah. And then also, this idea that, like, there's no cars coming. And we're going to sit here on the corner? I know. I mean, what's the point of that? I actually got in trouble, a police car pulled me over when I did that once. For jaywalking. Yeah, he, he was, he, I crossed because there was no cars coming and it, you know,

that's your right. It seemed like safe to me. You're taking the risk. And he literally ran up to me and stopped me. In San Francisco. In San Francisco in the tender line. Okay, you're like, bruh, I know. They're selling, those guys, there's crack in his hand right now.

That person's handing meth to an individual. And that person has a needle in their neck, shooting up heroin. And you're pulling me over? I was, I actually, I looked, I was shocked. And I just said, thank you, officer. And he's like, I've just worried about your safety. I was like, thank you, officer. See, but that's, you're also a New Yorker because you understand how to interface with the police.

Oh, yeah. It's just, you just say, there's like, twithry things. should say to a cop. Yes, officer? No officer. Thank you officer. That's it. You say those three words over and over again. The interaction is going to be very short four to five times as a warning. It's what you say like, why you're stiggling me out? It's like, okay, it's on now. Now it's on. You know, like, you walked across the street against the red light in front of me and then you gave me bunk. Like, okay, well now we're going to have to, this is no longer stop and press. This is, you know. I was waiting for a ticket, but thankfully he didn't give me one.

I was hoping. I had this happen to me in Santa Monica, where they're very serious about it. And they do have a little bit more edge about it because they will give you a ticket. Yeah. Because people do get killed, and there's a lot of car traffic, and people do get killed, sadly, or hit. And they also didn't have any crime at the time there, so the cops had nothing to do. So that was their broken window. Hey, when we left, I really want to get into...

hip camp. Yeah. And the pitch on that one, because I know the company well, but chain alice. Chain alias. Yeah. That was the first one. Is it a crypto one? It is a crypto one. I am shocked that you did a crypto investment. When did you do that one? I did it, you know, October 2018. Okay. So we're coming out of the ICO madness. It was during the ICAO madness. Oh wait. Yeah, that's peak. I'm sorry that you met 2019. So you're in peak ICO madness. Yes. We all know those ICOs as investors were giant fraud. crazy and you take your first deal put it on the triangular table yes and you say I got it I'm here I made it I'm on the Yankees I want a bunt I'm doing a crypto in here we go like this is a non-traditional first investment you could have gone with something safe hey I did

Pinterest here's my next UGC what is I had a thesis yeah let's hear a thesis so the thesis was you know one of my partners like when I started at benchmark in one of the wonderful things about a smaller partnership is that you don't have to choose a lane. Like it's not that, you know, I'm in, I'm like the consumer social person at benchmark. There's five people and we're covering an entire soccer field. And so you take more space. And so I decided I was going to spend more time digging in on the space. And I had kind of an intellectual curiosity around crypto.

I had gotten involved with it when I was at Greylock and I was digging in. And then this was, you know, I was reading anything I could speaking to. people and and then the ICO stuff started to take off and it was like everybody was going towards you know investing in ICOs it was a huge huge thing but it was honestly confusing to me because what I like as I looked at what was happening it felt like everybody was making these investments and infrastructure with this belief that if they built it the use cases would come and and there There was, you know, a lot of very high-fluid in talk about what the use cases would be if we had the underlying infrastructure.

But, you know, one of my partners, Matt Kohler, talks about how our job as investors isn't to predict the future, it's to see the present clearly. And so when I was looking around at how people were using crypto, what I really saw was a few use cases, which is number one, it was store value, which was largely Bitcoin at the time. Yeah, store value seems to be like your country is exploding. Yep. You don't want to be in Venezuela dollars. Yeah, yeah.

My mom's from Argentina, and like, you know, Bitcoin was a real thing in Argentina. And so I understood that use case inflation was crazy. Like, this is an asset that actually should be deflationary. You can't buy dollars. Yeah, you can't buy dollars. You can't get money out of the country. Like, there's real problems. I mean, Argentina amongst many.

The second was actually fundraising, which is what was happening on Ethereum and what was creating the ICO craze. It was too good at raising money. That's exactly. But so it was... So good they were breaking securities law. There was a lot of that. There was a lot of it was a lot of.

Let's be honest. All of ICOs were securities offerings. 98%. Like it was... I don't know one that wasn't a security. 99%. It's incredibly frustrating to me as an angel investor runs a syndicate to watch these local... You would say Ethereum was like an Ethereum was one of the first, like essentially an ICO.

Right. And it was like a real utility token. Yeah. Yeah. What is, explain to people. So this is your second use case. Yeah. Well, the money store and then you have raising money. Yeah. And then the third was criminal activity. Which kind of relates to the second. Yes. And the first. I mean, so like what was the, like, what was the use case that you could count on? That like, regardless of whether Bitcoin went up or down or whether Deutsche or whatever it is became like the token dejor, like what could you count on? It was at. money laundering. It was that illegal things were going to happen with cryptocurrencies. By the way, with currencies. Correct. Yes. Illegal things happen with currency. Yes. Yes. Yes. Yes.

That's the reason people do illegal things. Generally speaking, people are not doing illegal things for the fun of it. They're doing illegal things for the profit. And so that actually felt to me like in a way the most expansive use case. Wow. But what am I going to do as an investor? I'm not going to invest in like the next Mount Gawks or Silk Road. You can't short them. And you can't short them. And then as part of learning and going deep in the space,

I was very lucky to have coffee with Katie Hahn, who had been, this was before she joined Andreessen. She had been a justice department? She was, yeah, and she was a prosecutor for the DOJ. And she was involved with the Silk Road case and Mount Gawkes case. And during, like, while we were talking about it, because she was an early, she's fantastic, A great poker player, so I hear.

I haven't played cards with her, but I met her once at a conference, spent a little time with her, spent a couple of hours talking to her, and it's like really interesting, a prosecutor who's now investing in currencies that, aside from money store, some significant portion of it is people who don't want you to know what they've spent money on. Well, and so what she mentioned when I spoke to her was that while she was at the DOJ doing these prosecutions, she used channelysis to do the investigations. And so I... Well, there's an endorsement.

Well, and so I was like, you know... Where does the DOJ go to solve this problem? Right. So as a good little VC that I am, I wrote the name down and cold email... Zipip? The CEO, Michael Gruniger. As we say in the business.

Yeah. And it was... What was awesome about it was that I, you know, I spoke to Michael and realized that it was even more than I had anticipated, which was that, Yes, it was the tool that the government agencies, you know, U.S. government, but globally were using to do investigations on the Bitcoin blockchain. It was just, it was only Bitcoin at the time where that chain analysis was able to do these investigations for, but that it was actually an enabling part of the ecosystem because if you're a regulated entity, if you're a an exchange, and you are touching both Fiat, U.S. dollars.

and crypto, you need to be able to answer to the same government agencies that are using chain analysis of make, like, this is the compliance I'm doing to make sure I'm not part of some money laundering scheme. Right. KYC, you know, your customer. That's part of it, but AML is the big one for AML, anti-money laundering. Oh, AML, right. Yeah, yeah, to make sure that you're not, you know, part of some money laundering scheme

for a terrorist. Speaking of poker, there was some dipshit kid in Vegas during the Bitcoin era. I was like, oh, you want Bitcoin? Give me a poker chip. I'll give you a thumb drive with a Bitcoin on it. So it's like, well, what does a Bitcoin cost? Like, oh, Bitcoin now cost, let's just pick a number at the time, $2,000. You want a Bitcoin?

Give me $2,100. I'll give you a Bitcoin. Give me $2,200. So he's just doing this like arbitrage. I was walking around casinos, doing this. A's in jail. It's like, what you're doing is called laundering of money. Like, there's a reason why when you're at casinos, those chips have RFID on them.

They know the chain of custody. of every poker chip over a certain denomination. They probably know of all of them. So if you and I are at a poker game in a casino and we say like, hey, I'll bet you 5,000 on the Yankees are going to win or the Warriors are going to win, and I hand you the $5,000 chip. When you go to cash it out, they're like, what did you get the $5,000 chip? They know you got it from Jason Calcanus who lost the bet.

They're just waiting to see where your answer is. You're like, I picked it up off the floor. And they're like, yeah, no. You got to go get that person and bring them here. Yeah. Yeah, AML is one of these things that it's part of businesses that you would never get. I mean, Airbnb had to worry about money laundering, you know, because people would create fake locations and then pay as if they were a traveler to the host and they would just use that to launder money. And so there's all these companies have to be aware of it and have the ability to do the compliance to make sure that they are not a victim of it or being used.

used to do it and that they can, you know, do the work to not just be, you know, to do the investigations if they get contacted by a government agency, but to catch them also. Right. Crazy. And so chain analysis was using this and creating a data moat, really, around all the analytics that they were doing on the Bitcoin blockchain. And they were kind of a classic software business where they were doing a few million dollars of annualized revenue, had only raised a million and a half for,

So, and that was, yeah, yum, yum, that was, and so it was, yeah, and so it was a little bit like there's, this is, you know, it's real. I called it, actually, Michael once, he thought this is so funny. I call it a meat and potatoes company in crypto, because at the end of the day, it's a vertical SaaS company. Yeah. It just happens to be in crypto. Is that what, when you look at crypto, do you think there's an Amazon that's going to come out of this? Is it Google or an Uber going to come out of it? You would say Bitcoin already is the Amazon.

I mean, what an incredible success story. Right. Highly manipulated. That's my theory. Oh, there's definitely Massive manipulation. There's been a lot of manipulation. I think Chinalysis actually published a report on that recently.

They call it Painting the Tape. It's a fascinating concept that came out of, it's a term that Brian Coppulman should definitely make a billions of episode out of this. Painting the tape was a technique where people would take a stock that didn't have a lot of volume. Yeah. And let's say you and I own a bunch of the stock.

We then get a bunch of brokerage account. so we start trading between each other. So we're losing 5% or 2% on the trades, whatever, we're paying a Vig to somebody. But with Bitcoin, you can do this without paying that much of a Vig if you're doing peer-to-peer transfer, right? Now there's volume. Oh, volume's increasing.

Volume's increasing. Maybe it's going up just a little bit, but people go, oh, wow, there's a lot of volume here. And when people look at the cryptos after like XR, when you look at that coin market cap, and you look at the volume, that volume is Fugazi. There's no way that's true. It can't be.

a lot of its exchanges trading with themselves. And so consumers are like, oh, $10 billion traded in crypto today? It's like, really? You really think there was 10? That's a big number. Yeah. There's not $10 billion of crypto. So if you paint the tape and you tick it up a little bit, and then a phenomenon happens

that it went up 3% a day. So you and I paint the tape. We're the original Bitcoin owners at 10 cents or $0.5. We just start painting the tape and we're, you know, chopping up the, you know, raising costs. this with, you know, millions of accounts, potentially, tens of thousands of accounts, wallace can be created in some programmatic way with software. Tape gets painted. All these people watching the news, you plan a couple news stories.

It's going up 3% a day. There was a lot of this. In 35 days, we're going to double. Yeah, yeah. There were a lot of telegram groups that were doing basically what you articulate. I mean, pump, pump. They called them pump, pump, pump. They literally went into those telegram groups, and it was pump, pump, pump with the name

with the group. I know. You spent some time there too? I remember those. Yeah, of course. And it's like, we're all going to buy this coin on Sunday. Yep. But remember, we're not selling until Saturday. I'm like, the person who created this group has already bought their coins. By the way, dipshits. Like, yeah. Whoever created this group is selling their, selling their coins to you as part of the pump, pump. And we'll see who the bag holder is. There was a lot of that. So I like that approach. That's a good one. Yeah. Any pushback from when, we were talking before. for how a partnership works. Do you need consensus? Can somebody block each other or are there

no rules officially? Well, so we do vote and there is kind of the idea that I think it's like, I don't know if it's average or number of people. It's generally, it's probably average. And I say probably because like honestly we've never, while I've been at benchmark, like the way we think about it is like a company comes in to present. And, And we have a conversation about the company. It's a very truth-seeking conversation, and it's not a conversation where I'm, like, defending the company or selling the company. It's really this conversation, because when we invest in a company, like, the only way

we can do our job with five people versus, like, the 200 at Andresen, is to really work as a team. And when, you know, when we invest in a company, it's not just Sarah's investing in this company, it's benchmark as an investing in the company. You know, it's part of the, part of the benchmark. family. And so it's a very true seeking conversation, and a lot of things come out of it, like, oh, we should look into this and this and this. Or, you know, you get a sense of the sentiment. And, and you don't actually ask for a vote unless you really are ready to do the deal.

Got it. So the act of asking for a vote means you're committed. Yeah. Well, it means like you're kind of, you're ready to do the deal. Yeah. And, and for the most part, and like, while I've been a benchmark, we've never gone to a vote. and then not gone on support. There's a little bit of this understanding that if you're bringing this company to a vote, it means you want to do the deal. And unless, like, I have a real point of view.

And, look, I brought a company to a vote once, and, you know, we go on a 10-point scale, and I got a three on one of them, you know? And it wasn't one that I ended up doing, but it was like I was almost there to do the deal. And someone had a real reason to not like it. And, you know, I spent more time. I'm on that and ended up being right.

But so you, but... Is it anonymous when they do the score? No, no, no. You just put it out there. Does everybody do three to one and turn it over? You kind of, we read an issue of paper and gave it to the person. Wow. Yeah.

And the person just reads it. Because you don't want anybody to influence. That's what I was thinking. It's very, this is why when I do voting at our events or whatever, I hate having people go first because I watch people change your votes because they're like, oh, a group thing hits in. But the best companies, aren't they polarizing? that's you know Is that true or not?

I don't know at Benchmark well I'll say this at Greylock we would talk about that a lot actually that some of the best investments were polarizing

Facebook is one of the more famous examples where David Z got a note from one of the more senior partners that this investment was going to ruin the firm you know it was like that type of really three million dollars

going to ruin the firm and even you know Airbnb B, which Reed did, was on one, on one hand, it was an obviously incredible company. I mean, clear network effects growing really quickly in marketplace, like the type of business that Reed like salivates over. Yeah, live for. Yeah. And on the other hand, it was, I think, five percent ownership, you know, and so all the time, you know, as VCs, we're talking about, we want to get a real ownership stake to be worth the time. And so there is some, you know, some polarity.

on that point. But for the most part, like the belief is, is that if you, if a company is great, there's going to be at least one other strong advocate for that company. That's what we believed at Greylock. And I think that's, that's by and large, pretty true. I mean, there are certainly exceptions. Why are people obsessed with ownership percentage and are you? Well, we, we really are. And the reason, the reason is, is it, there's a, there's a a couple different reasons, but number one is like for, for benchmark, like, again, we have zero leverage in our system, you know, like, we're not a firm where people are taking on 20 boards because there's just no fucking way we could do that, right? Like we have, there's nobody to whom I can

say, do this, you know, find, help this person find a CRO or, uh, do the analysis, kind of dig into the financials for me. Like, we are doing all the work ourselves. And so, our, we're not able to scale ourselves. And that means that each time we make an investment, we have to make that investment really count, you know, and we make it count because we're doing a lot of work on it, and hopefully that has a real positive benefit to the company itself. But we also make sure that we're, you know, able to buy as much of the company as we can when we invest because we actually have a small fund.

And so we don't tend to be the group that's then doubling down each round after that. It's really about that first investment. And then pro rata from there. Well, we don't go heavy on the pro rata. We're not the group that is saying, like, defend our pro rata. We're the group that says, look, I have to be internally consistent. And usually when we invest, because we're trying to get as much ownership, it means the difficult conversation to the seat investors of what's the right way to allocate pro rata.

But then when the next round happens, we're not going to, you know, speak out of both sides of our mouth. Right. And so you'll step back. Step back to make the financing successful. Right. Yeah. I got bullied a lot in my early days as an angel where it's like you got to give up your

prorodda. And now I don't. I would for Bill Gurley. I would for Sequoia. I would for Chema. And I think that's always the conversation, which is. But I'll take half. You know, like I'll negotiate a little bit because I don't want people rolling over me.

Yeah. And look, like I don't want, if someone's creating value for the company, I don't want to take value away from them. I want them to continue to be adding value. But as you know, what happens a lot for these companies is that there are a lot of people around the table and they're, you know, they're not creating value and the founder has to be optimizing for the future value of the company. Right. You invested your second deal as a camping startup. Yes, hip camp. Hip camp. Now, most people would be like camping startup, really? Yeah. It's not venture scale. I had the same reaction when I looked at the seed. However, yeah. You got Airbnb.

and you've got a couple of other trends going on. People may or may not know this. But every time I've tried to go to Yosemite... Yes. No vacancy. Impossible. So I go to the Evergreen Lodge, which is outside the entrance, which is charming. It's like an old 50s lodge, like in the Catskills, where everybody eats the same time.

There's two seatings for dinner, and it's pre-fix, and then they have marshmals for kids. They've got all the activities for kids going on, three regalaise, all this good stuff. I like that better. But to get into having... or into like the the valley and stay there. I think you have to book a year, I was told, or something or six months. So there's something going on that people want to get back to nature. That's exactly it. Is that it? Oh, that's a huge part of it. What was your thesis on this? I mean, the thesis, so, look, I had the same reaction when I met Alyssa for the seat. I met her at Greylock.

And I was super impressed by her. But I had a similar reaction to what you articulated, which is that it's like, I don't know. Like, does it feel big? It doesn't, like, like, camping, like, you know, it's just a niche audience. And, and there was, there was something that was starting to work, but it was still incredibly early, and she hadn't really figured out how to acquire supply. Like, she had maybe a handful of hosts, but it wasn't a machine yet. And so, there was a little bit for me of the combination of not really knowing how to acquire supply, which, as you know, for marketplaces is a really, you know, 90% of the time, the first step is to aggregate supply that it just didn't feel like she had totally figured that out and I wasn't I didn't

have conviction on the magnitude of the opportunity and so I passed and what ended up happening is we stayed in touch I spent a lot of time I mean I led product at Pinterest for the discovery team and so we would end up doing some product sessions you know and like digging in together so this how can we be how can I be helpful and being helpful even though you don't have equity yet that's yeah people the new VC brags and how can I be helpful all this like anti or like mocking VC Twitter

which I'm interested in your position on I love it. I love it. You love it? It's so great. Of course. Why is everybody blocking these? I'm watching like the ball's blocking

the Lexus is blocked. I just watch everybody block them and I'm like, do you guys not have a sense of humor? They're breaking your chops. Exactly. You're wearing a fleece vest drinking $7 coffee. My favorite one right now

is the VCs congratulating themselves. It's so great. Just three. And I'm trying to link bait them with my tweets. So I tweeted. They should just automatically retweet you. They won't. Dude, they won't.

And this is my big existential problem is I'm so laughable in my own behavior that I'm not parable. You can't parody me. I'm uncansable. Are you the Trump of Venture? That's what I'm, that's what Harris Fisher is trying to do. And I'm like, please don't do that because I'm not a horrible human being. I actually care and I go to work. I like to think I'm smart.

Maybe. I think I'm Tverson, but I'm not an idiot. But maybe. Okay. Maybe. Tremendous portfolio, okay? A couple of unicorns. Six, seven.

Stop counting. Okay. But how can I be helpful, which is parried, is actually... It's so, like, it's a genuine thing, most of the time. It's a real thing. Yeah. You want to be helpful. Yeah.

Because it feels good to be helpful. No, you wouldn't be in this business if you didn't want to be helpful. Yeah, it's a service-based business. Yeah, exactly. All right. So you pitched everybody. So how did you get passed? Well, you know, what happened, it was funny.

Like, I, you know, what we do when we, when we have a company that you're spending time in is we pass the ball to one of the other partners. You have another partner. And usually you figure out who's the partner, who's the best fit to, like, help you figure out whether we should make the investment or not. And, you know, I, like, I had been spending time. time with Alyssa, and you could tell that something was really starting to work. Like, she had cracked the code on acquiring supply. Oh, okay. Supply is very important in a marketplace. And then

the classic thing of a marketplace, which is that if you unlock supply, demand follows. And that was exactly what was happening is that she was unlocking supply and you would just see the correlation, you know, the economics. And supply in this case was a landowner. Correct. Because she was on the pot. I forgot which episode. I'll get the number right now. But Oh no, actually I do know. It's episode 959. Alyssa Robavaggio. She's dynamic.

I was taken by her. I was like, this is a killer founder. Yeah, yeah. She's very compelling. Self-possessed. That's the word, right? Like self-possessed. Yeah.

I think I've been really focused on that word because I think I heard Michael, what's the author's name who did? Lewis? Michael Lewis. Somebody asked Michael Lewis, like, what are you, what are all your subjects have in common? I think he said self-possessed. Interesting. You know, they have this sense of who they are.

Who they are. You're not going to, like, knock them out of their seat. Yeah. You know, if you criticize them or whatever, they're just, they know what they're doing. They know where they're going. They know why they're doing what they're doing. They got like a sort of samurai Jedi, like confidence to them. Yeah.

Like, a good Jedi is not like, yeah, I don't know what I'm going to do next week. It's like, well, I'm a Jedi. I know exactly what I'm doing next night. I'm going to be a Jedi. That's what I do. But unlocking the supply. Yeah. So she was unlocking the supply.

Which is landowners. correct. How do you get a landowner? Well, to say, let some random San Francisco hippie, yuppies go camp on my land. Sounds risky to me. Lawsuit coming. You know, and it's like one of the key things for any marketplace is how do you create trust, right? And so one of the things that Hip Camp has now and had then is an insurance policy so they can kind of allay that fear. And there's there's a culture with. hip campers where it's, you know, leave it better than you kind of found it, you know? Right, sure.

Leave only, take memories, leave footprints. Oh, I like that. That's what we were told is Boy Scouts. Like, you just, you take the memory. Of course I was. From New York? What people don't understand is when you're a city kid, they want to get you out of the city. I totally get that.

So we would go up to 10 Mile River Camp. Jewish kids would go to Catskills, right? Mm-hmm. I don't know if you're Jewish. Yeah, I'm Jewish. Never went to the Catskill. You said your dad would argue about religion. I'm just thinking like, well, so he's either Catholic or Jewish, because those are the few people who are arguing.

Yes. Yeah. Well, and so I'll, the other thing that I realized with Hip Camp, just kind of back to the conversation on how big could this get, was twofold, which was one, I realized that one of the things that was special that was happening was that, you know, it was progressing from just campers to glampers. you know, because landowners, huge change. And landowners were investing in their land. They were adding a tree house or a yurt or a tent, which was opening up the addressable market for Hitcham. Exactly.

Which is why happened with Airbnb because it used to be couch surfing, but not families and not business travelers. And now they have business accounts. And this for business travelers are like, I much prefer to stay in an apartment with a, you know, kitchen. Yeah, and it's classic marketplace, which is you start with a really small niche, you nail it, you get it, like you make people really happy, and then you expand from there.

Each head, wedge strategy, what do you call it? I mean, I kind of think of it as like just the bullseye, the red hot center, and then you expand from there. Super important. Yes, super important. Why? Because that's the only way to build liquidity in a marketplace. What does it mean liquidity?

For people who haven't heard that. Most people, like, I kind of call it the Dilbert version, which is it's just the efficiency with which you match a buyer and a seller. The way I think of it, I call it the hippie version, is like just the happiness that both the buyers and sellers have when they transact. And I think about it's happiness, not just efficiency, because it's more than just how efficient the matches and do you have the right supply. It's about the product.

You know, it's about the policies you use. Like, how do you delight a user and make it? How did you unpack that and learn that? Did you operate an Airbnb or how did you? get that the happiness and the joy between the two parties? Because I'm operating in Airbnb for the six months. Yeah. And I, we do a text message to people when they're coming in. Yeah. And in the text message, we remind them no parties, 10 people, there's a security camera, quiet time at 10, all this stuff. If you want to have a party or a photo shoot or anything like that, there's a separate

prize. You can request a quote for that. And we do it for that reason because we had a party. And people denied they knew that. So we started making it really explicit. But we, we We also started putting in my picks, best ice cream, best ramen, best delivery on Uber eats, best delivery on postmates, and we would give them these things and then say best activities, half moon bay, you know, here's how to go to the Presidio, here's Pacifica, here's all kinds of things you do. People started taking our suggestions and then writing us back on the SMS, then we would tell them, hey, thanks for staying.

We also left the gift basket out, which nobody does. then we started getting crazy reviews. Then the trust happens. You get the reviews. Now the place books like crazy. We just got a very famous NBA player who wants to stay at the place for three months or whatever. I was like, well, that's interesting. And it's about that joy. I like operating it. Forget about the finances. I just like being a host.

Yeah. Fun. I mean, I just was reflecting, I guess, on why, like, you look at goat. The shoe. The shoe company. The shoe marketplace. You guys invested in that? No, I wish. I wish we didn't. And then there's StockX.

Yes, StockX. We had StockX on the pod. Oh, cool. Goat hasn't come on. No goat. Have we tried goat? Or we just... We got to work on it.

They have a great story. I've never... Why no goat? What's up with goat? Someone's getting in trouble right now. Goat? Ghosted? Jake how?

200 plus thousand views per episode? It could be a little jelly. They're a little jelly on the sock ex. All right. Well, the story, you know, one of the things that you you can't help but reflect on for Goad is, imagine, you know, you're looking at this incumbent eBay. They're massive.

Yes. They have, like, you are this little startup, and you have, like, zero inventory. And they have liquidity. And, well, eBay. eBay, massive liquidity. Massive, you would think. But then there's, like, there's this vulnerability, which is actually the catalyst for the company, the founder, they were working on another company.

And they, it was not working, running on fumes at this. point looking for a pivot and the founder had ordered a pair of shoes off of eBay got them and they were counterfeits. And it was kind of, it's a real pain point, right? You spent 600 on your Yeeas and they're not real? Exactly. No, and that's, that's, and so what Goat realized was that there was a real unmet need here. And it wasn't, it wasn't like, you know, liquidity, just like that Dilbert version of

liquidity, you kind of think, oh, I just have to add more supply, more supply, more supply. But then how are you ever going to disrupt an incumbent? And you do it because Goat made a better product. Like there's all these things you can do. If you're looking for that pair of Uisies and they don't have your size, you leave a notification, like set a reminder or notification if they get it. And just the data normalization, because you're doing one vertical, you have complete data on the category, which, like eBay's, they might have complete data of eBay mortars because

there's a lot of stake, but they're not going into shoes. The taxonomy, how to do the search. And then of course, and then the most important thing, which is that's kind of assurance of authenticity. And so that is, you kind of have to like if you're, and I'm a product person, like that's just who I am. And so you can't help but think more expansively and realize that there's something about the happiness and how happy someone is. And that's why part of what you want to do with a marketplace when you're starting is you want to really, really focus because it's a classic, like, if you try to make everybody happy, you'll make no one happy. Exactly. You got to go deep.

Yeah. All right. And then, and sorry, so then just to loop back to Hip Camp, I introduced Bill to it. And he was basically like, well, if you don't do this, I will type thing. Oh, that's a great reaction. And that's, you know. And so, and look, like I was leaning in, like, I wanted to do it, but then to have that confirmation that there was, you know, and it's kind of back to the gray lock. Like, if you don't get at least one other person to be as enthusiastic as you are, then you might be standing alone. it was a good sign. All right. Listen, I've kept you for a long time.

You can follow Sarah T-A-D-E-L on the Twitter. You active on the Twitter? I am. Yeah, all right. Oh, wow. Here we go. Mark Adreason, you know, he's a huge fan of the show, and he doesn't do any meetings anymore.

All he does is, like, listen to the pod. And he's texting me, like... All the time. It's the critique is that I'm like, Mark, I do this for a living. I don't need you to tell me that I'm talking over Sarah or... Like, literally, that was his feedback on the list. You keep talking over the guest.

Let him talk. I'm like, okay, Mark. Oh, anyway, he's listening right now. Congrats to Peter on hiring you. Can you give me some New York City recommendations for my upcoming trip to Manhattan? Great question, Mark. Yeah, yeah.

I'll send you my Pinterest board, Mark. You got a favorite, favorite? Oh, New York has changed so much. It's so weird going back, isn't it? It's crazy. It's so weird going back. I walk around. I'm like, who put up these weird,

30-story, 60-story, 100-10-story buildings that look like a jenga. Yeah. It's a weird situation. But I'll give you the place I love to go when I go there now. Decoy. Oh, yeah. You know Decoy?

I think so. The duck place? Yeah. And then what's the name of the other restaurant upstairs? He's got two restaurants on top of each other. Anyway, this guy, he's a Jewish chef who is obsessed with Chinese food. So he's hybrided it. So he's got a pastrami dumpling.

Whoa. He puts like pastrami. that he makes Jewish style into a like fried dumpling Chinese style, but he also got obsessed with Peking Duck. So he makes downstairs in a place called DECO. I'm going to go to flight tomorrow. It is so unbelievable. I rent out they have a communal table.

That's why I know of it because I'm obsessed of Peking Duck. That's my obsession. I am obsessed. Have you been to Hong Kong recently? Oh, like actual Hong Kong. Like 10 years ago. Mott 32 is the best Peking Duck right now. in the world, I think.

They do it so perfectly. They cut it so perfectly. Oh, my God. Beautiful. The best PKK duck here is that Hakasan. Yes. I'm so with you. It's unbelievable.

I feel a kinship here. What is going on here, Sarah? We could have met in our 20s. And this could have been it. But I don't think, and they were on different teams. Different teams. You're married to a woman. So it wouldn't have worked out.

But we could have been besties. We could have been best. Feels like we could have been besties. these in New York. We definitely have a Peking duck in our future. Let's do it. Let's do it. Look at us. It's the best. Look at us. Who would have thought it? Not me.

Not me. This is my, you know that Paul Rudd clip? The viral clip? No. There's a viral clip of Paul Rudd. Okay. On a show called like Hot Wings. And all they do on this Hot Wing show is eat wings. And increasingly

hotter sauce. And he doesn't know why he's on this. He's a movie star. And he's on a YouTube show about eating hot wings. And he goes, at one point, the guy's like, look at us. And he's like, yeah, look at us. He's like, who'd have thought it? And Paul Rudd just looks at him. He goes, not me.

This is the greatest. Roll the clip of Paul Rudd. All right, listen, Sarah, you crushed it. Thanks for coming on the pod. Continued success. And I really would like to get a little slice of hip camp. If you do another round. All right.

Appreciate that. Can you just put a good word for me with Alyssa? I'm talking like, just want to maybe 500K, maybe 750. Just let me sneak in to get a little slice on the B. I'll have to send this to Alyssa and make the ask. I'm asking Alyssa right now on the pod. Give me a slice. I'll go.

And I tell you what, when you hit your next milestone, we'll do an episode of the pod. I'll offer a podcast episode to get an idea. I like the barter. We'll barter right now. Let's horse trade. We'll do an episode. me, you are Peking duck

from a yurt I'll get the Peking duck from Hakasan I'll have them ride it up to the yurt the three of us do You know how plenty of your audience Absolutely I'll get on that cap tape

I'll get her a benchmark cap tape Well let's do it all We'll see you all next time On Angel Dude you crushed it Well done That was hilarious