20VC: Cyan Banister on Her Relationship To Money, Risk, Her Investment Decision-Making Process, Why We Will See A Reckoning in the Early Stage Market, Her Biggest Takeaways from HQ Trivia & The Future of Silicon Valley

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle. In Today’s Episode You Will Learn: 1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC? 2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions? 3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting? 4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows? 5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world? Items Mentioned In Today’s Show: Cyan’s Fave Book: Snow Crash As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is the 20 Minute VC with me, Harry Stebbings, and I always get in so much trouble with my intros on Twitter and I sound too excited to have someone on the show, apparently. I hope you forgive or at least understand my excitement for this episode, but my word, I really have wanted to have this incredible individual on the show for a long, long time. And so with that, I'm thrilled to welcome Cyan Banister, one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of, check this out, SpaceX, Uber, Affirm, Open Door, Postmates, Niantic and Thumbtack, to name a few. Today Cyan is a partner at Long Journey Ventures, joining the team there following a four-year stint at Founder's Fund, where she led deals in both Niantic and HQ Trivia. Prior to Founder's Fund, Cyan was a super-successful early operator and angel, co-founding Ziviti,

• 0:43Harry Stebbings?

  and before that being an early employee at Ironport, leading to that acquisition by Oracle. I'd also want to say a huge thank you to Kevin Harts, to Brian Singerman and Catherine Boyle. Some amazing questions today, really did so help me there. But before we move into the show today, I'm sure you've heard about it, but my word, I love a product called Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity, and Carter now offers fund administration, so you can see real-time data in the Carter platform and work with Carter's team of experienced fund accountants. Go to carter.com/20vc to get 10% off.

• 1:27Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:55Harry Stebbings?

  You have to check them out. But the time's come and now I'm very, very excited to hand over to the one and only Cyan Banister.

• 3:06Speaker 01

  You have now arrived at your destination.

• 3:09Harry Stebbings?

  Cyan, as we were just saying now, we've been wanting to do this for a very long time. So I cannot thank you enough for joining me today. I've heard so many great things from Brian Singeman, from Kevin Harts and so many other people. So thank you so much for joining me.

• 3:19Speaker 02

  Yeah, thank you for having me.

• 3:20Harry Stebbings?

  Not at all, but I would love to kick off with a little bit on you. So tell me, how did you make your way into the wonderful world of startups, but especially investing? And my guest, what was the genesis for founding Long Journey?

• 3:29Speaker 02

  Yeah, so I made my way into startups back in 1998, 99. So my background is I come from the internet sort of laying pipes era, which gives away my age. But I basically worked at ISPs and then eventually came to San Francisco and joined a series of startups. Many of those startups failed. There's like four or five that failed. Before I won the startup lottery, which was a company called Ironport. And Ironport exited to Cisco for a sizable amount. And I basically tried to figure out what to do with the money that I made. It was the first financial windfall I'd ever had in my life. And so my husband talked me into putting it into high-risk startups. So my first check was into SpaceX. And I have to tell you, like, taking everything that I worked really, really hard on for many, many years,

• 4:13Speaker 02

  because it was true sweat equity and putting it into something that was literally blowing up on launchpads at the time, was incredibly difficult decision for me. So basically, that's what got me started. And then I made a series of not so great investments after that. And just like all investors do, you learn as you go along. So I've been investing for about 10 or more years now. And when I first started investing, there were very few early-stage investors. We kind of all knew each other. And the ecosystem, it's flourishing and there's lots of early-stage angel seed investors now. And so at some point, around the time that Y Combinator kind of really hit its stride, some of the valuations of companies were out of whack. And so I took a step back and decided I was going to go work at Angelist for a little while and help Naval with syndicates, because I was leading my own syndicates. And I had a lot of fun there. And that's where I met Lee Jacobs,

• 4:58Speaker 02

  who's my partner at Long Journey Ventures. And we basically saw eye to eye on a lot of things. And we worked together on building the ecosystem for Angelists. And we all love working with Naval. And well, I guess that kind of sent the international signal that I was hirable, because I think a lot of people didn't think I was hirable. So Brian Singerman reached out to me. And I'll never forget this meeting I had with him. He took me to breakfast. And I was expecting him to talk to me about like relationship stuff or something like that. But he then asked the question, he said, hey, we had a whiteboard and we're trying to figure out who our next partner is going to be, because we just raised a new big fund and we need help deploying it. And your name was at the top of the list. And I have to tell you, like, I about cried. So there's very few venture firms I would join, and Founder's Fund is one of them. And so the opportunity to work with that team for four years was just phenomenal.

• 5:42Speaker 02

  But I also discovered that I'm not cut out for late-stage investing. It makes me deeply unhappy. So I decided to go back to my roots and do early-stage. And who better to do it with than Lee, to be honest with you? So that's kind of the genesis of Long Journey.

• 5:54Harry Stebbings?

  I love that in terms of the genesis and such a special team at Founder's Fund. I do have to ask, when SpaceX is your first check, did that actually make it challenging? Because you have such a great first check. It's almost kind of hard to live up to you. Did it almost make it challenging post that?

• 6:07Speaker 02

  Not really, because I assumed I kind of buried that nut, so to speak, kind of like a squirrel. And at some point, it would turn into something. At first, though, I thought that I'd made potentially the worst financial decision of my life. And I think that when that ended up not being the case, and SpaceX started having successful launches, and the trajectory of SpaceX started taking off, literally, I became more bold rather than less. So I think that it definitely gave me Fuel, if you will, to launch my own career. So I was very fortunate to have access to a company like that at my first check. And a lot of people don't have access to those sorts of deals. So I think that I was incredibly lucky to be able to put my first check in there.

• 6:43Harry Stebbings?

  I love the space analogies and SpaceX analogies that we've got going here. I do have to ask you, because you mentioned winning the startup lottery with Ironport, and then obviously the first check into SpaceX. And obviously, it changes a lot of trajectories around personal finance and personal wealth. And you've spoken before about leaving home and building a life for yourself. I guess with such a journey, how do you think about, and it's one that I think a lot about, but how do you think about your relationship to money today and how it's changed over time?

• 7:06Speaker 02

  It's funny because I used to hate money, literally hate money.

• 7:09Harry Stebbings?

  Why did you hate money?

• 7:10Speaker 02

  So I started out not being a capitalist in my younger years, and I felt that all corporations were greedy. And the only way that people rose ahead of anybody else was through nefarious means. I definitely fell along those lines of thinking. Partially, it was because of lack of experience and because I was also down and out myself. And so I looked at the world around me and it just seemed unfair. When you have that mindset, then all of those things become true internally, right? And I changed that mindset when I started my first job and then also when I started my first business. And when I started realizing the power of capitalism and the power of being able to earn a paycheck and the pride and the sense of well-being that it gave me, that was incredibly transformative.

• 7:53Speaker 02

  But for a while, I had an unhealthy relationship with money. There's a funny story that one of my best friends loves to tell, which is, I would get home from work and I'd empty out my pockets and I would throw all the money on the floor. By the time I moved out of this apartment, which was like a year and a half later, there was, I'm not joking you, like a good centimeter, centimeter and a half of change and money all over the floor. And luckily, it ended up being a lot of money. And we ended up going to Coinstar and turning it into things that I could actually use. But I just didn't like touching it. It was almost like I was money phobic. It was really weird. And so even to this day, if I have change in my pocket, I have to get rid of it. So luckily, there's tip jars everywhere. And so any cash that I have on me that's kind of spare, I just shove it into a tip jar. I've been doing that for quite some time now because I really don't like carrying it on me. But I do like making it.

• 8:36Speaker 02

  If I wasn't an investor, maybe I'd be doing other things, but I get really excited. Excited when a company does really well and there's an exit and then I can redeploy that money into yet another company. So a lot of my investment style is evergreen, even though I'm wealthy on paper, often cash poor because I redeploy almost every dollar back into the ecosystem that I don't live off of. So I think that shocks people sometimes because sometimes people expect you to have a ton of liquidity that you can just have available to you at any given time. But that's not necessarily true for everybody, including me. So anytime I have an exit, it's a celebratory moment, not for my own personal gain, but because that means that more startups are going to flourish and I have another chance at it again. If I were to fail over and over again, there goes my chances.

• 9:16Harry Stebbings?

  I mean, I guess the question that arises for me from that is like, risk is often what stops people, you know, they have an exit and then they introduce savings and they introduce alternative finance products which can provide stability to them. How do you think, and again, it's rather another deep one, but how do you think about then as a result, your relationship with risk, given what you just said?

• 9:31Speaker 02

  Oh, I take a lot of risk and I think with great risk comes great reward. If you're risk averse, some people are incredibly good at being risk averse and investing and I really admire them. Because there's people who will deliberate over a deal and maybe only do one or two deals a year and those deals end up being great. But that's hard to do. It's really, really hard to do. And I admire it because it takes a certain analytical ability, quantitative ability, to be able to do that. I'm more qualitative and I'm definitely driven by pattern matching, gut instinct, watching trends, reading things constantly. But it's not necessarily data driven. I just have hunches that things are going to work and I have a good feeling about the people who are building those things. I think that I take extraordinary risk and sometimes it makes people uncomfortable, but it often means that I'm the first check in.

• 10:16Speaker 02

  I'm sometimes the largest check and I move very quickly and that's how I win some of the deals that I win. I don't recommend that people without that level of conviction to do that strategy because it may not work out. It works out for me and I trust my conviction. And so when you learn to trust yourself and trust your convictions, I think that definitely works in your favor.

• 10:35Harry Stebbings?

  Have you always trusted your convictions? Because Bunny, you know, in the past when I look at myself as an investor, I've only been investing for say three years. And I've had convictions and I haven't trusted them because of market size or whatever analysis or theory that I've done. And it's in most cases not worked out, but I haven't trusted it because. I've been in experience and I've been learning and have you always trusted in your convictions? Or has it come with time and success?

• 10:55Speaker 02

  I think I've always trusted my convictions, even before I was an investor. And partially as a survivor, as someone who depends on making decisions, just literally to survive. You know, I come from the streets. You have to have conviction, right? You can't really not have conviction. So I think that I've always had it. The moment I decided I wanted to leave school, I left school. I make very quick decisions and I do think that some people find that intimidating. And sometimes these decisions are wrong and I go back and I reevaluate like my thinking on that. And then maybe adjust how I react to things in the future. But I tend to be, some might call it impulsive, but I think high conviction and quick.

• 11:30Harry Stebbings?

  Totally agree with you in terms of kind of the importance of it, especially on the investor side. And actually, you know, I spoke to Mazzio before the show. I spoke to Catherine Boyle at General Catalyst before the show. And both of them said about kind of how fast you are to build conviction. It was actually Catherine Boyle that said, in terms of like the gut feeling you get with founders. She said, how incredible you are with it. But she said, how do you test founders for traits like grit, resilience, internal fight? And where does that like conviction come from when meeting them?

• 11:52Speaker 02

  Oh, man, pattern recognition, I guess. I think that I am a very curious person and I talk to so many people from all walks of life. And I don't Google search people before I meet them. It's a hard and fast rule for me. So that way, when I go and I meet them, I'm getting a very raw, unfiltered version of them, other than what they're kind of putting up as a facade to me, right? But my version of them is unfiltered. And so all I know at the time when I meet them is that they're a founder and they're starting something. And I just want to know more about it. So the first question I ask every single founder is tell me their story. Like not the business, I don't want to hear about the business. I want to hear about how they got to where they are and why this problem? Because every single human being has a choice on how to spend their time. What causes them to wake up in the morning and decide and choose to do the thing that they're pitching me on?

• 12:37Speaker 02

  And a lot of the times I make up my mind about the person before ever hearing about the product within that first 10 minutes of them telling me their story. And often what they do is they tell you a story of resilience. And maybe they're a founder who came from Pakistan and they came to America. And the journey to get to America is incredibly hard. And so that shows grit, right? To be able to like leave a country and come to America is extraordinary. Or they were on the streets themselves, or they put themselves through college. One of the things I'm looking for is overcoming some kind of hardship, some kind of struggle that someone had. And a lot of times it's really interesting because the struggle leads them to the problem they're trying to solve. A great example of this is Siren Care.

• 13:18Speaker 02

  The founder comes from a family of basically podiatrists who treat people with diabetic foot. And she was expected to go to school to basically also become a doctor. She had tiger parents who expected her to follow their footsteps. And she decided she didn't want to because she was really upset at having to watch her mother amputate people's feet. And instead wanted to solve the problem so that the amputations never happened in the first place. So she grew up in this environment. The fact that she rejected going to school in favor of starting this company and went against parental advice, which can be incredibly hard to go against for a lot of people, to start a sock company that monitors temperature on people's feet. I mean, it was a no brainer for me. Once I heard that story and then I saw kind of how she navigates working with people, the product,

• 14:03Speaker 02

  then the rest of the story comes into play, right? So I think that's how I get to quick conviction on people. And a lot of times people are really surprised that I ask this question. That means that other investors don't, which I find weird. You know, we have this period of time at the beginning of a pitch meeting where you have an opportunity to get to know each other. But what I see other people do is they sort of exchange niceties, like social lubricant, if you will. Like, what did you do this week and how are you? Okay, let's get to the point. What are you working on? But you're not going to figure out who the person is sitting across from you with those types of questions. You're just not.

• 14:30Harry Stebbings?

  Listen, I totally agree with you, which is why I often ask questions, kind of like I asked you, which is, you know, relationship to money, relationship to risk, relationship with parents often. I'm totally with you in that respect. One thing that I find challenging is how we denigrate people's desire for money, actually. And some founders will say, I just want to make a shit ton of money and I think this is the best way to do it. And I find the startup world kind of chastises it and kind of views it in this kind of demonic way. Do you think that's fair? And how do you think about it when founders like actually just fundamentally hungry for wealth creation?

• 14:58Speaker 02

  Well, I guess it depends on what they want to do with that wealth creation, right? They could turn into Elon Musk. And I'm sure that Elon was an Elon in the beginning days of his trajectory. And maybe he was out to have lots of money, but now he's transformed the world with electric cars. And potentially space travel and private rocket launches. So I think that sometimes you start out with just wanting money as your goal, but then you learn that just having money and lots of it is kind of not fun. It does not make you happy. It makes life easier, like you don't have to sit and count your change at the cash register to make sure you have enough money for everything that's on the conveyor belt, right? You know, it's a different type of life, but at the same time, I don't think we should demonize it. I think there's nothing wrong with anybody on this planet wanting to make money. And I think that it's a beautiful thing because then it gives you freedom to do other things.

• 15:42Speaker 02

  And those other things could be giving back to other people so that they also have freedom to do other things. So there's a lot of ways that people could go with it. I think demonizing it is wrong. You'll never find me ever demonizing a single human being that wants to make money.

• 15:54Harry Stebbings?

  You mentioned space assets there and you mentioned Elon and we chatted a little bit about it before. The thing that kind of also I'm kind of in awe of you for is, you know, when you look at the antique, you look at space assets and a number of your investments, there's inherent market timing risk in a lot of them. It's something that I always feel very uncomfortable taking as a risk category, so to speak. How do you think about an approach market timing as a risk when you're investing today?

• 16:13Speaker 02

  Well, sometimes I'm wrong. It's all about timing, right? And sometimes I invest in a company that's too early. And then what happens is they fail and then five years later, the timing is right. And then somebody else does it and they succeed. And that's happened to me. I'm not always right on my timing. But the question I ask myself is, do I believe in this future that this entrepreneur sees so clearly in their mind? If I do believe in that future, do I believe that they are the right person to execute it? And so let's look at Travis from Uber, for example. So Travis was a no brainer because he is aggressive. He is competitive. He is a lot of the things that people say about him. He's also brilliant. There's a lot of things about him that people never got to see because the media, anytime you rise and you do well, the media starts to kick in. And usually you're not their darling.

• 16:58Speaker 02

  I'll just put it that way. If it bleeds, it leads. And so they'll do everything they can to take you down. And Uber definitely had missteps culturally. They pushed people to move fast, break things and challenge all regulations, et cetera. But in order to be literally a world changing company, they had to do that. And they had to have those behaviors. They weren't going to be able to do it by being nice all the time. So Lyft has benefited from Uber and Uber definitely helped pave the way for Lyft to exist. So Lyft had the luxury, if you will, of being the nice company with the pink colors and the fist bumping. So. Does that make them a better company? No, it's a duopoly and one was doing the fist fighting and the other one was putting on a marketing face of being the kinder, gentler company. I take both Lyft and Uber. I've had shares in Lyft and Uber. At this point, they're kind of fungible.

• 17:41Speaker 02

  And so I think at this point, I mostly interview drivers to see who's the happiest and who's treated the best, and that indicates who I will ride with. Right now, I have a problem with Uber where I'm locked out of my account, which is kind of ironic, and it's just too much effort to reset my password. Like, I went through the reset process and it was too painful. So they have a UI problem, so I just decided to switch to Lyft for the time being. So for years and years and years, probably eight or nine years, I rode Uber and now I'm riding Lyft.

• 18:06Harry Stebbings?

  Absolutely. When I'm in SF, I actually like Lyft too. In London, it's Uber all the way, but in SF, it's Lyft. I do want to ask one thing, and I wanted to ask you when you mentioned earlier, but you mentioned kind of pricing being incredibly high coming out of YC in that time when you went to Angel S. You were seeing pricing now at levels that I've never seen before. Twenty-five prees for seeds played by multi-stage funds when there's nothing there. And great for the entrepreneurial ecosystem in some respects. But I am now with Long Journey and investing again on your own. How do you think about assessing your own relationship to price and price sensitivity coming in at the seed?

• 18:36Speaker 02

  Well, what's going to happen is there's going to be a reckoning, and there always is one, market will work itself out, where people look at their returns seven, eight years from now, and they're not going to be great. And so I think that will create some discipline in the market. So one of the things I love about my partner, Lee Jacobs, is he's incredibly disciplined. And just so you know, like, he founded Long Journey and I joined him. And I joined him because he has this level of discipline. I can become irrationally excited about a deal, but the price can be out of whack. And then you have to sort of do the economics, okay? And you just say like, okay, well, how much dilution am I going to take on? Am I actually going to do my prorata? How does this play out if this company becomes a billion dollars, $10 billion, et cetera? Because everything has a ultimate endpoint in value. It's not infinite. And I think some people think that things are infinite, but if you actually count how

• 19:19Speaker 02

  many companies in the last 10 years have been worth over $10 billion, it's very few, right?

• 19:24Harry Stebbings?

  Sure.

• 19:24Speaker 02

  So to be able to get those kind of returns, you've got to be more price sensitive. And the other thing is that I think that people have FOMO, and so they don't want to miss the deal of the century. And the deal of the century may look good on the outside because you see only valuations being posted. You don't see are the returns that people are making on those valuations. Right. So I think somebody pointed out the other day, and it was very wise, which is a company that exits for $250 million that you have better economics on is a better return profile than a company that exits for a billion dollars that you don't. So if you're in the returns business, you should definitely care about these things. And that's the business I'm in. And so I think that at Long Journey, we're often the first check in. We have led deals now that we're excited about and we have to get our target ownership,

• 20:07Speaker 02

  which is not as bad as as high, I shouldn't say bad, but as high as some other firms are. Some need 15, 20% ownership and we actually aim for 5%. We're a seed fund and we're small, but I think that people who are not conscientious of this, what's going to happen is at the end of the road, LPs at the end of the day, look at returns. And then the fund managers that have the best returns will continue and the ones that don't will probably have to hang up their hat.

• 20:29Harry Stebbings?

  What do you make of the big multi-stage firms, all the names that we're talking about here? What do you make of them going so aggressively back into seed? There's been quite a few deals where I haven't done now because as I said, they're 25, 30 pre's and bluntly 100 to 250K checks. And it just doesn't make any sense at that point. What do you make of multi-stage being so aggressive at seed?

• 20:45Speaker 02

  So it's a strategy and it's a strategy to cut out the seed ecosystem and other series A investors down the road. So there are certain firms like A16Z, et cetera, that have ownership targets. And so if you want to ruin their chances of getting the ownership targets down the road, you gobble up ownership early. And so that's the strategy that they're deploying, which if they're the bigger firms that are multi-stage, they don't make money necessarily at the seed. They make money identifying and plowing money into in the A and B. And so in order to have that relationship already in place, it takes writing a seed check or an angel check, if you will. It has so many different names now. I don't know what to call it anymore. But that first check that a company gets, often you'll see these multi-stage funds write a million dollars or something into them.

• 21:27Speaker 02

  And they usually don't let angels in unless it's like a tiny bit, like 50K or 100K or whatever. And then the seed funds definitely don't participate. And part of that is just to literally it's sharp elbows at the series A and B level. There's a reason I'm not cut out for that type of investing is my elbows are not very sharp. I tend to like collaborative party rounds. I like it when everybody does well. I often have scaled down my allocations to let people in. To deals that I think are beneficial to the company because I think if they help the company, we all benefit. I do think that some people definitely don't view this world in that same way. And that can be challenging and I understand it. I don't want to knock them because at the end of the day, they're looking at returns as well. And they're trying to get the best returns possible. And sometimes that means having sharp elbows. But at the seed stage, I tend to like the angel approach to things where the more the merrier.

• 22:11Speaker 02

  If the founder wants to have 10, 20 of us, then they have 10, 20 of us versus just one person. I think having one person in one fund can be detrimental because if they don't follow on, you're kind of dead in the water.

• 22:20Harry Stebbings?

  Yeah, absolutely. And then on the flip side, though, you can also have no one doing it because there's too many people with too small an allocation.

• 22:26Speaker 02

  Exactly. There's a lot that's not optimized right now in the ecosystem. I think it will be over time, but right now there's just an abundance of early stage capital. And we'll see where it all lands, but it takes a while to figure it out. We'll see who has the best strategies and what actually works down the road.

• 22:41Harry Stebbings?

  Can I ask a tough one? It's like, given your gut conviction around people and then given kind of what you said there about kind of sharp elbows. And I think Bunny, you're kind of such human first and people first approach. Help me out here. How do you deal with it when founders are not performing, when CEOs are not meeting expectations? What does that conversation look like?

• 22:57Speaker 02

  This is an area of growth for me, I think, because sometimes I'm conflict avoidant. I love being helpful. And then when it comes to giving that hard advice, I like literally lose sleep over it. For someone who's so blunt and open, like when you're telling somebody where they're failing. I try to be very careful with what I say and how I say it to people because there are power dynamics, right? And like your investor calling you up and being like, wow, you are really screwing up should be rare. And I've had to have those calls and they're, they're tough. And a lot of times it has to do with management style. And a great example of this would be working with HQ Trivia. I had to have a lot of phone calls for that company. Here's an example of a very high conviction investment that I did that went wrong. But a lot of times people are doing their best with the tools they have in their tool shed, right?

• 23:39Speaker 02

  Like we often invest in people with little to no prior experience managing large teams or scaling businesses. It's not like they woke up, but somehow through osmosis gained these skills. And a lot of them are afraid to reach out for help because of the whole crushing, killing it nature of our world. Where they have to put on a good face and pretend like everything's okay. So I just think you have to be careful about how you do it, but. It's really important that we do do it because when we withhold this information and we don't tell them how we're thinking, they don't have an opportunity to learn about themselves. The other thing is that if they choose not to take my advice, that's their prerogative. I always tell every entrepreneur that they have a choice on how they act on my inputs. Because I'm not running the company day to day. I don't see the nuances of everything. I don't understand the business like they do. This is just an observation from the outside and I could be wrong, but I also could be very right.

• 24:23Speaker 02

  But this is an area where I'm constantly trying to improve because you can really destroy morale and you can add negative value to a company, which I try not to do.

• 24:30Harry Stebbings?

  Totally with you and I listen, I suffer the same. I'm always completely conflict avoidant, being the true Brit that I am. I do have to also, when you think about HQ trivia, I'm never one for like, oh, you learn more from something not working than from something working. You know, it was such a roller coaster ride in many respects. Were there some big takeaways for you from being there and being so involved, as you said on many calls and being as involved as you were?

• 24:47Speaker 02

  Well, sometimes the market tells you things and you should listen and not be as contrarian as I tend to be. So there's a reason that everybody pulled their term sheets. So that was one of the most competitive deals that was out there. I think there wasn't a single firm that didn't issue a term sheet. And I waited and waited and waited to see like how the news would pan out with what was going on with the co-founder Colin. And I am skeptical of media. And so when there is a narrative that is dominant, are there narrative violations to be had? That's something that Jeff Lewis came up with. I know that people use that all the time now, but there's definitely violations out there. And I believe that in the Me Too movement, there was a spectrum, which again is controversial to even talk about a spectrum in that movement,

• 25:27Speaker 02

  but of really bad actors like Weinstein and the Olympic coach who abused hundreds of girls, to someone who said something not so great at work. That is a far, I call it a canyon of difference. And Colin was in that category where he said something inappropriate at work. And so I had to figure out whether or not I forgave that situation and whether or not it warranted ruining his career and the company not being funded. And ultimately I decided that I would take a stand for him. It shouldn't ruin his career. But what I discounted was the founder relationship between him and his co-founder. So that was something that was always in the back of my mind, was in the back of everybody's mind. And I chose to ignore it, even though it was right in front of my face because. I had some weird belief that they built Vine together and that worked.

• 26:12Speaker 02

  So maybe there's some sort of magic to their dysfunction. So it was a narrative I told myself. There was no magic to their dysfunction. They were dysfunctional together. And why they chose to start another company together is mysterious to me. But and I may never understand that. They both were incredibly gifted and are gifted and talented, but could not see eye to eye as founders. And when you have those kinds of conflicts, they will break a company. Now I've adjusted how I invest in companies. So when a company has multiple co-founders, I add a question, which is how do you resolve conflicts? How long have you guys known each other? What's the last conflict you had together? So now I do a lot more investigation around conflict. This is why I also love husband, wife and brother, sister and brother, brother, sibling teams is often they've had an entire lifetime or many, many years to resolve conflicts, right? And some people shy away from those teams, but I actually get really excited about them.

• 26:56Speaker 02

  I mean, the Colosseums are a great example for Stripe. But it definitely changed my style of investing. Probably we'll see in the future, but probably for the best, where hopefully I can avoid investing in companies that have underlying founder conflicts. So that company failed entirely because of founder conflicts. It was the right time. It was the right product. HQ trivia was transformative and could have been how we consume media in the future, had they played their cards right. But if you have a lot of infighting and you don't have a good culture and you don't have a cohesive team, then these things fall apart, especially if you're lightning in a bottle and you're moving really fast like they had to.

• 27:28Harry Stebbings?

  Yeah, I totally agree with you there. And I really appreciate you being so open with that. You mentioned kind of the media there and kind of challenges with it in respect to pushback from the media. One thing that was on Twitter last night, when I put out about, you know, I've got science coming on the show tomorrow. What should I ask? And one person mentioned, and I'm taking their words here, a pro cop anti BLM tweet that you sent out a few weeks ago. Talk to me about this. The thing that's so terrible about it is I didn't even know how to ask the question without potentially offending someone. So I hope I haven't offended someone with the way I asked.

• 27:54Speaker 02

  You're so brilliant.

• 27:55Harry Stebbings?

  My only way to say is like, talk to me about it.

• 27:58Speaker 02

  Well, okay. So first of all, I'm pretty sure you go through my entire history, both through podcasts, Twitter, whatever. I have the words, I am against BLM have never come out of my mouth. So I don't know where people get that. One of the things I've learned recently is that people like to infer things. And if you speak in what sounds like a declaration, they try to infer or piece in things that they think might be true about you. I think this is also a flaw of Twitter. Twitter is a beautiful thing. It connects people in ways that are just profound. But at the same time, it also destroys people. And I think that for someone to just sum up a person based off of 140 characters that they may have said, or they inferred that they said, is frankly wrong. And I am not typical in that I don't sit and deliberate over every little thing that comes out of my mouth before I say it.

• 28:41Speaker 02

  The other thing is that I do support Black Lives Matter protesters. I do think that a majority of the movement is well-intentioned. I do think that police need to be demilitarized. I am pro some amount of police. So he was right about that. I think that it's a very complicated thing to talk about in 140 characters. So people try to get you to say very precise statements that you're either for something or against something. And it's a very polarizing thing that people are doing online. So they come after you and they'll say something like, if you're pro-police, you're racist. That's not true. It's just absolutely not true. And there's a lot of people out there who have, the road is paved with good intentions. But they're out policing thought, policing people's language. They're out to point out every wrongdoing that you've ever done. Eventually, we're all wrong. Eventually, we all fuck up.

• 29:24Speaker 02

  And then sometimes these words don't have the gravity that they should have. Racism is a very serious thing in which it is wrong in every way. But if you go around pointing a finger at everybody, calling everybody a racist, then nobody's really racist, right? Like, we have to stand up against these things. Now, granted, he didn't use that word, but that's where that line of thinking goes next, which is, if I don't wear a Black Lives Matter shirt, or I'm not out there marching with people, and even worse, if I'm not destroying businesses and I'm not part of Antifa, or I don't support Antifa, then suddenly, I'm all of these things, which I'm clearly not. So the reason why I didn't think this was spicy was that I can deny all of it because it's just not true. So I think that people hear and see what they want to see and what they want to hear. I know who I am. I'm confident in who I am. I make mistakes, sure. But I also live very organically and out in the open,

• 30:09Speaker 02

  and I question things around me. And I don't just accept the dominant narrative in any given thing. So, yeah, I'm going to say some things sometimes that might be stupid. But I'm also speaking sometimes for people who are afraid to speak. So every time I say something that gets backlash, I can't tell you the thousands of people on the other side who message me saying, gosh, I wish I could have said this. I can't. Get fired. I mean, how horrible is it that we live in a time where you can say something that is 140 characters or less because maybe you're busy that day and you didn't think it all the way through and it's just a career ender for you. Like, should we live in a world that's that intolerant? I don't think so. I think it's miserable.

• 30:43Harry Stebbings?

  Can I ask, does it hurt? I occasionally get someone say something not nice about me and not occasionally so much anymore, more frequently than they used to. And it really hurts me. Like, honestly, it will ruin my day. Does it hurt you? And how do you think that kind of?

• 30:55Speaker 02

  Sure, sure, it hurts. I've had days where, I'm just gonna be honest with you, where I've cried all day long because I can't understand how people come to these conclusions and how they could have so much hatred in their hearts. I don't even want to relive this moment, but there was probably the first time I was almost canceled and the amount of death threats that I got was insane. Now, luckily, I know that most of those are just empty threats. They make people feel good and underlying, I think those people are really hurting inside. And so the way that they can feel good, a momentary amount of goodness is to lash out at somebody and to tell them something horrific. The other thing is that some of it's trolling, which is looking for any kind of response from me. If they can get under my skin, it makes them feel really good. So I understand trolls. I've done a really deep dive study into troll and troll culture and I've even hung out with lots

• 31:40Speaker 02

  of trolls to try to understand them and figure out what they're all about and why they're motivated to do what they do. But mostly, it's just to point out hypocrisy. And the other thing is to rile you up and get a response. So I admit that that day, the day after that, it worked. It got to me. And I had to get offline for a little while. I had to recuperate. And then I decided I was gonna come back stronger because I was like, you know what, I'm not gonna let this happen to me. Because, one, I know who I am. I know what I'm about and what I'm not about. And my friends and family and the people I work with know who I am and what I'm about. And anybody who questions that is welcome to have dinner with me or have a phone call and they can learn for themselves. Some of the people who threatened me, I wrote back to them and I said, I feel sorry that you're resorting to threatening me. A lot of them backpedaled afterwards and said, I'm sorry, that was really rude.

• 32:23Speaker 02

  And I'm like, yeah, it's really rude. Sometimes people don't think that you're even reading what they write. So that's the other thing is they get shocked when you respond to them. And then they realize, oh, I'm not being a good person. So they're just saying stuff off the cuff too. Look, we're all busy people doing the best we can. I think a lot of people don't realize just how busy I am. I am a parent. A lot of people don't know that. I am a investor in over hundreds of companies and there's overhead to that. I'm part of a team. I can't possibly be expected to know every single detail about every current event that's going on in this world. No one should be expected. And so we don't always have all the tools to respond to something. Does that mean we should just be quiet? Because I don't think that's how we get to the right answers is by being quiet. If someone can't challenge you and challenge your assumptions, then how do you get to the right answers? You don't. What happens is you just start getting lonely and afraid and unfortunately, sometimes radicalized, right?

• 33:08Speaker 02

  The more we try to silence other people, the more radical they're going to become. It's just going to push each other to the opposite extremes. And to be honest with you, I think that's a really dangerous place where people are so afraid to speak that they double down on some of their bad ideas.

• 33:20Harry Stebbings?

  Do you not think that's why we are now?

• 33:22Speaker 02

  We're getting there. Yeah, absolutely. I think we have not seen the worst of it. I think it's going to get worse. And this is what happens when there, you know, the red scare where everybody was a communist. Or being gay, if a guy wears pink, then he must be gay. Then there's witch hunts. I mean, historically, we've had multiple of these events in history. And right now, this is no different, except for I think it's really misguided. I think that systemic racism exists. I think that profiling exists. I think that a lot of the things that they're talking about are real issues that exist. But I think the solutions to the problems are not necessarily the best. So I disagree a lot with the prescription that is given, if you will, which is to go around and finger point and blame everyone for it constantly, rather than just sort of addressing the issue. That's how I choose to deal with current events is I have a few wedge issues that I really care about. And so I've just decided to focus on those.

• 34:07Speaker 02

  And I'm not going to tweet a bunch of platitudes that are meaningless. Like, there's all these companies and founders and people who, the problem of the day, whatever it is, they'll change their profile picture to that thing so they can fit in and look like they care. And some of these people are some of the worst actors in our industry. Like, if you look at people who are just like really outspoken about women's rights in the Me Too movement, later on, you discover that they were predators themselves, right? So I do question people's motives when they are so outspoken about certain causes, whatever it is. So I just decided I'm not going to go and champion all of these causes that I'm not as knowledgeable about. But there's certain things I care about, like the Second Amendment of our constitution. I also care about mass incarceration and people being put away for drug crimes. So I think those are things- That I'm very passionate about and also homelessness, right? These are things that I experienced.

• 34:52Speaker 02

  And so I'm just going to focus on those things. And I was focusing on them before this happened and I'm going to keep focusing on it. So I'm not going to jump on the latest parade because I'm guilted into it. I'll just put it that way.

• 35:03Harry Stebbings?

  Can I ask, you mentioned homelessness there. And it's, you know, obviously I have a lot of friends in San Francisco and it's always attributed with San Francisco. It's like the homelessness is out of control. How do you think about the homelessness in San Francisco? And how do you think about kind of a solution based around that?

• 35:14Speaker 02

  Diversity is the solution to that. So we have no diversity in politics. So if your government has been run by the far left for so long and it's not working, I think it's time to look at alternatives. So I think the issue is that we need to see people running for office here that are probably more centrists. Because I think somebody on the far right or the right is not the answer for the city. I think it's too polarizing, but I think someone in the center with more right leaning thoughts on the spectrum of thoughts is what the city needs. I understand that you're in England and you have your own political stuff going on over there. But I do think that conservatives and Democrats, I hate to say liberals, because a lot of conservatives are actually more liberal now, which is really weird. But conservatives and Democrats play a very important role in society. And it's not an all or nothing sort of thing. We're all born with our own unique ability to look at the world.

• 35:58Speaker 02

  There's neurodiversity that is really real. Some people are not neurotypical. We're not all the same. We don't come to the same conclusions. And sometimes we're born with certain brains that lead us a certain way, right? And so I think that the way that I choose to look at this is I think that Democrats are really good at short term thinking, really good at innovation, really good at challenging everything, but not necessarily understanding the long term repercussions of their actions or thoughts. So I think that the conservative party is much more concerned about the long term consequences of any short term thinking. And so thus they're conservative. So they move slowly. It's not that they're against change. It's not that they don't want things to happen. It's just that they believe there's a different timeline in which change happens. And it should be thoughtful and it should be deliberated. And that the issue of the day is not necessarily the leading reason why things should be changed, that it should be really thought about.

• 36:43Speaker 02

  Because people's minds change, culture fluctuates. And so they're very thoughtful about that. There's also flaws on the conservative side because sometimes they can be too conservative and they might not move fast enough. But I would argue that in the last hundred years, we have an accelerated rate of change, which is unprecedented. And part of that is due to pop culture. Which is mostly dominated by the left, right? So I have to give credit where credit's due. The reason why we have some of the rights we have around gay rights is because of shows like Will and Grace and Clear Eye for the Straight Guy. And those really move the needle when you watch television and you see someone who is like you on TV. Then you start looking around you and you're like, okay, well, my brother is gay. My uncle's gay, my sister's gay. I love these people. And it just opens up your heart. And then eventually societal norms change and then everybody gets on the same page and we move in the right direction.

• 37:24Speaker 02

  So I think what would solve homelessness in San Francisco is literally diversity of politics. Because currently, the solutions of just take more and more money and throw it at the situation is not solving it. It hasn't solved it and it doesn't seem to be solving it. So I think we need different ideas at the table.

• 37:38Harry Stebbings?

  In terms of kind of the next few years for San Francisco, a lot of people are saying that this is kind of the end of the concentration of power that San Francisco's enjoyed over the last many decades, actually, when you look back at the historical timeline. And when you look at the actions that's happened since COVID, it kind of suggests that. Do you think this is the end for the kind of concentration and monopoly of power that San Francisco's had? Or do you believe in the longstanding kind of future that it could hold?

• 37:57Speaker 02

  It's interesting to me how a lot of people have fled San Francisco to red states. So I'm hearing about people going to Montana and Wyoming and Texas. And I'm not talking about Austin, Texas. I mean, some of them are little liberal enclaves. Like if you look at Montana and you look at Blue Sky, as soon as you go into that town, the political signs start changing from Trump 2020 to Biden Harris, right? But at the same time, I do think that they benefit from some of the conservative thinking of these states. And that's why they're going there, because they're like, gosh, I feel safer here. Well, why do you feel safer there? Could it be that everybody believes in the Second Amendment? Possibly. Or, gosh, my quality of life is so much higher here. Well, why is that? There's all sorts of interesting things I find a little ironic that they want these things out of life, but could not figure out how to make it work here. And I think we can make that work here.

• 38:39Speaker 02

  I do think that politically, we are so messed up that this town is eating itself. And it's caused these problems, to be honest with you. Like, there's a reason startups aren't staying. There's a reason that people are fleeing. That's because of San Francisco and frankly, all of California. You can only tax people so much. And then eventually, they're just like, gosh, every dollar I'm making, I take home 30 cents. Well, of course, they're going to flee to a state that has better taxes. Really, that's what it's coming down to, is that people feel unsafe here. We have a DA, Chester, who will not prosecute crimes. I just found out yesterday, a friend of mine, whose house was burglarized, the perpetrator were let out of San Quentin for COVID. They robbed his house, almost kicked in the door of his neighbor who had a child home. These folks have been let go and are not going to be prosecuted. So when you don't prosecute crimes, or you call them quality of life crimes, people are going to move elsewhere where they feel safer and where they can defend themselves and their families.

• 39:24Harry Stebbings?

  So why does he do that? Is that a desire for a low conviction rate? I mean, help me out, sorry, I'm a Brit.

• 39:29Speaker 02

  It was a very complicated pass. And I don't know the full extent of it, but I do know that his parents are convicted murderers. And I think that probably shaped his worldview as a child and as a young adult, where he has great compassion and sympathy for criminal behavior. So I think his heart is in the right place where he believes that he can give people second, third, fourth, fifth chances, right? And eventually they'll come around to doing the right things. But if you can get away with doing things constantly, then what is the deterrent? There's none. At some point, people will have to protect themselves and they're already starting. Like, I can't tell you how many people's opinions of the Second Amendment in San Francisco have changed. If anything, the silver lining of all of this is that there's more gun ownership and more people who are pro-home and self-defense than ever before. And so I think, to me, that's a silver lining. To someone else, it's their personal nightmare, right? But chess is creating this, the state of California is creating this.

• 40:14Speaker 02

  It's really interesting how people don't see that they're eating themselves. So this town is just literally eating itself.

• 40:19Harry Stebbings?

  Would you be

• 40:19Speaker 02

  I'm from it, I don't know, I don't have a crystal ball, I really don't know. I know that people are really happy moving to Colorado and wherever they've moved, Arizona. And they're like, gosh, I have a swimming pool and a yard and I live in a neighborhood where I can walk around and I'm not stepping in feces. They're like, wow, what a change. Because part of it is you become so desensitized to this that you don't even realize. Like, when I travel, I lock my car wherever I go. And then my friends and other places are like, why do you lock your car? That's so weird. I'm like, how do you feel so safe? That's really weird. So

• 40:45Harry Stebbings?

  I'm from London, we lock our cars here too, otherwise they're gone.

• 40:48Speaker 02

  Yes, I actually think that now that rents are going down and property value is going down, I think more conservatives should move to San Francisco and maybe we can turn this place around.

• 40:55Harry Stebbings?

  Don't, I wanted to do a tweet, narrative violation. As a VC and a contrarian, I'm thinking of dot, dot, dot, moving to San Francisco. Which I'm also worried that people will believe me and then I'll be totally screwed.

• 41:07Harry Stebbings?

  I thought my mother would read it and should probably kill me. So I should quickly. I do want to move that into my favorite element this time. So I'd love to a quick fire answer. I say a short statement and you give me your immediate thoughts. How does that sound?

• 41:18Speaker 02

  Sounds great.

• 41:18Harry Stebbings?

  Okay, so tell me, what's the favorite book and why?

• 41:21Speaker 02

  So I have something to admit, which is I've read very few books.

• 41:24Harry Stebbings?

  Same as me, but everyone comes on, they're like, oh, I read like three a week. And I'm like, oh, really? I read.

• 41:29Speaker 02

  I read maybe one a year if I'm lucky. That's how busy I am. I have a couple of things that make it hard for me to read. One is I'm really busy and two, I have ADD. And so if I sit down and I look at a book, it has to be absolutely riveting for me to want to sit and read it. Otherwise I read a chapter or two and I put it down and then I walk away. So I'm going to say my favorite book. It's going to be very cliche, but it is what it is, which is Snow Crash by Neil Stephenson. And probably seconded by Diamond Age by Neil Stephenson. It's really funny because I'm mentoring someone and he asked me the same question. And he asked everybody the same question and most people gave them business books, but I gave him Snow Crash. And he was really surprised by it because he said, it's really interesting how nobody thinks that I in particular would like science fiction. And so I always recommend that people read science fiction because I think it helps us think about the future and what the future could look like. So I think some of the best business books, believe it or not, are science fiction books.

• 42:14Harry Stebbings?

  I love that. I was worried you were going to say Sapiens, so at least you said Snow Crash.

• 42:17Speaker 02

  I haven't said Sapiens yet. I haven't read it yet. I mean, I just, I can't say that because I don't know what it's about.

• 42:22Harry Stebbings?

  Tell me a really interesting one. How did having children change your operating investment mindset view of the world?

• 42:28Speaker 02

  Well, I'm fascinated by what they're into. I think that it helps me, like, I understood that Roblox was going to be a thing before it had its meteoric rise just by watching kids play it. So I think that there's certain insights that they give you about the future and what it looks like. They're kind of like science fiction novels themselves, just like we were to our parents and our parents were to our grandparents. We do things differently at a rate that exceeds the previous generation. And so by all measures, they're exceeding us because of their access to information that's just at the tip of their fingertips. But they also do things so differently, like with touchscreens, with voice to text. Siri is actually a real thing in their world, whereas like a lot of grownups, you don't see them using it at the same level that I see kids using it at. I think it's fascinating. I think if anything, it made me more focused on how I spend my time.

• 43:11Speaker 02

  I'm not open about it online for a variety of reasons and I've become a little more open about it just because. I have an 18 year old now and she actually wants me to talk about her. So for a long time I would not talk about her because I really felt that she needed to understand what privacy meant. And she needed to understand kind of the cost of giving up that privacy. But recently we had a discussion and she was very excited about joining me on Pop Shop Live and me discussing her openly. I don't think that she feels this way, but some kids feel because we overshare our children online from the moment they're like conceived literally. To every diaper change and every everything, some kids can think, gosh, my parents don't love me or care about me because they don't tweet about me constantly. Or they don't put me up on Instagram constantly, but that couldn't be further from the truth for me. I love my kids fiercely.

• 43:52Harry Stebbings?

  It's a big thing to understand it, the cost or the kind of privilege of privacy. Well, not the privilege, but you know, the cost of kind of being out there and kind of how it can change. Do you think she understands that? Because it's a huge amount to understand at any age, let alone at 18.

• 44:03Speaker 02

  Yeah, I think she understands it more. I think that her generation tends to be, I'm going to say a generalization, but based on my limited experience of kids her age. But I do think that they tend to be more private and they tend to have tighter social circles online. And they have like a public persona and a private persona, and sometimes even a secretive persona that nobody knows about. And they also tend to be very, very minimal. They want for very little. All they want to be is happy. And so I think it's a really interesting change from previous generations that I'm witnessing. The ambitions are different, the goals are different. It's just very different. It's a sad time right now in 2020 for kids her age. Kids were supposed to graduate from school and they were supposed to have a ceremony and they built up their whole lives around this moment. And COVID just basically took it all away. So I think it'll be a very defining moment for this generation, like what we're experiencing right now.

• 44:47Speaker 02

  And the repercussions of it are going to be long lasting. So it'll be really interesting to see what happens. But I learn a lot from young people and I think that people, if you have kids or don't have kids, should spend time with younger people because they have a lot to teach us.

• 44:58Harry Stebbings?

  I totally agree. As someone very young, I totally agree with you. Tell me, what's been the single best returning investment and how did it come about?

• 45:04Speaker 02

  Well, that'd be Uber by far. The story behind that was I had a driver that took me to the airport in a town car. His name was Roger. I've been out of touch with Roger, so I don't know where Roger is. But Roger was one of the first drivers for Uber. And when Uber first started, the marketplace obviously needed to be seeded because it didn't work naturally until it was. So they hired a bunch of drivers to drive around for them and pick up people until they could get that flywheel going and actually. Start making the market work. So Roger and his family were the first group of drivers. Like, he started doing so well that he started bringing in more family members from Brazil and eventually had like ten cars on the road. Well, one day he took me to the airport and he handed me the business card for Ryan Graves. And he said, I'm working for this company called Uber Cab in the future. Don't book me directly. Try to use the app. And he's like, it's cheaper than what I charge because I charge a minimum of two hours.

• 45:48Speaker 02

  And this is like by the ride. So I started using Uber Cab. And at the time, I think I texted to get a car because I think the app wasn't where it is today by any means. And it was interesting because Ryan's phone number and address was not local. And I really wondered why a taxi company was not even located where they were taking it on. So I kind of dismissed it based off of that and didn't call Ryan right away. And Roger insisted every single time I went to the airport, you need to call Ryan. You need to call Ryan. And he kept giving the updates on the business. And basically, it was when I met Travis for the first time at an offsite event that I was on. So the other thing that I do is I kind of catalog away founders as I meet them that are interesting and just sort of store them away for future, looking at what they do next. But Travis was basically not working on anything at the time. And he was incredibly aggressive in nature and all of the things I told you about earlier.

• 46:32Speaker 02

  And so I thought, well, that's a really interesting person who's outspoken and definitely sticks out. So like, I'm gonna keep track of him. Well, I saw him presenting Uber at another event. And I thought that was very fascinating because he was pitching it as an investor because Ryan couldn't make it to this event because Ryan was the CEO at the time. And I had this epiphany that someone who's that aggressive in nature wasn't gonna let someone else be the CEO of the company for long. And most likely, he was the right person to take on the taxi industry. So I made a gut decision, which I posted the email where I emailed my husband and I said, we need to put money in Uber ASAP. And he said, how much? And I wrote back, how much? And then I got to work just finally getting a hold of Ryan Graves. And then that's how the investment happened.

• 47:08Harry Stebbings?

  What a story that is. I didn't actually know that on the full background there. I've heard little tidbits, but I didn't know that was the full story. Okay, so moving from that investment to your most recent investment. Tell me, what's the most recent publicly announced investment? And why did you say yes and get so excited?

• 47:19Speaker 02

  Cash Drop might be the most recently announced public investment. Cash Drop's amazing, first of all. Sometimes when I download an app and try an app, if I love the person afterwards and that whole sort of inception story pans out for me that I talk about, then I'm just a hundred percent in. And this was no exception. I downloaded the app and tried it. It was amazing. And then I got on. On the phone with Ruben, the founder, and what an amazing story he has. He came here as an undocumented immigrant and went to school, graduated at the top of his class. He's a polymath, he's brilliant, and eventually worked his way into getting a US citizenship, which again, going back to what I was talking about, is incredibly challenging to do and hard. There's a lot of friction to it. So he's a dreamer. And the fact that he's a polymath, I also find interesting. So he's a really, really good pianist. He's got so many skills and they're amazing.

• 48:01Speaker 02

  And he's basically setting out to change the world for people who are like him. And it really resonates with me because those people are also like me. So there's people who are entrepreneurial on a smaller scale, who running a taco stand, or a hot dog stand, or selling a T-shirt, or a vinyl pin, is literally life-changing for them. And so what he's made is a frictionless, super simple way to list an item and put it up for sale that can be done socially or in person. And the rate of growth that he's had on this is just incredible. And so for me, it was just like a no-brainer investment. I was so excited to invest in it. I just think that, again, it's the founder journey. His journey is just incredible. So I admit that I have a soft spot for immigrants. If anything, I lean immigrant biased. I tend to like people that come to this country who still understand why this country is so precious

• 48:45Speaker 02

  and understand what they're leaving behind and why there's opportunity here. I think multi-generational immigrants such as myself sometimes lose touch with that, right? We all came here from somewhere. And I think people forget about the struggles that our families all had and where they came from to make America. I think that that's part of what's going on right now with a lot of the protests is that we've forgotten also a group of people who also helped make America. And so I think that that's also at the core of the pain and the sorrow and the suffering of what people's families have gone through. And that journey for those families is incredibly hard. So I'm always impressed with people who talk about their journey in such a way that they're putting it behind them and they've learned something from it and they're going to make the world a better place because of it. Does that make sense? Like, they're like, "My family and I had this incredible hardship and I decided, rather than feel bad about it for the rest of my life,

• 49:30Speaker 02

  I've decided I'm going to change it for everybody else, or I'm going to be different in some way." And I think there's something profound about that individual journey where someone makes that pivot in their life to do something different. And that could be defying your parents, that could be defying your culture, that could be defying a country, that could be defying all sorts of things. But I think there's something remarkable about people who have that level of conviction and that level of spirit that propels them every single day to get up and do what they do.

• 49:54Harry Stebbings?

  Cyan, listen, I've completely flouted the 20-minute PC rules for this interview, but I've just loved talking to you so much. Honestly, I've been thinking that's a terrible name for a podcast when I think about this interview. Honestly, I've just so enjoyed this. I can't thank you enough for being so open and brilliant. So thank you so much for joining me.

• 50:08Speaker 02

  Absolutely. Thank you.

• 50:12Harry Stebbings?

  I mean, if you can't tell, I absolutely loved having Cyan on the show there in such a more broad and diverse conversation than we normally have on the show. If you'd like to see more from Cyan, you can on Twitter at Scientist, C Y A N T I S T. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at Hstebings1996 with two Bs. I always love to see you there. But before we leave you today, I'm sure you've heard about it, but my word, I love a product called Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to Carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity, and Carter now offers fund administration.

• 50:54Harry Stebbings?

  So you can see real-time data in the Carter platform and work with Carter's team of experienced fund accountants. Go to Carter.com/20vc to get 10% off. And if you've been listening to our show, you've probably heard of Brax, the first corporate card for startups with no personal guarantee or credit check, up to 20 times higher credit limits than traditional cards, plus rewards like three X on eligible Apple products and seven X points on tools like Zoom and Slack. Brax has helped thousands of companies scale faster to reach their potential. This month, they are extending their special offer to our listeners. Apply for the Brax card by November 30 with the code 20VC, all spelled out, to receive a $500 credit after spending $1,000. Even better, you can also apply for Brax Cash, a bank account alternative

• 51:38Harry Stebbings?

  with unlimited free wire and ACH transfers with no minimum balance required to create an account. You can apply for an account today at Brax.com. And last but by no means least, if Carter and Brax really change the game in terms of fund admin and finance, Amplitude is that for product. Amplitude helps the top product in growth. Themes, companies like PayPal, Instacart, Peloton, my favourite, and Atlassian, build product experiences that convert and retain customers. With their product intelligence platform, you and your team will really be able to better understand user behaviour, ship great experiences faster and retain more customers. They've become the gold standard in analytics for teams asking, what is happening in their digital products, why are users converting and what do we build next?

• 52:20Harry Stebbings?

  See for yourself how companies like Twitter, DoorDash and Cisco build for growth using Amplitude and visit amplitude.com/20vc. Discounted scholarship plans are available for qualifying startups, you have to check them out. As always, I so appreciate all your support and I can't wait to bring you another fantastic episode this coming Thursday with Owen McKay at Intercom.