The Exchanges

Q 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?

A 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 seated, 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 10 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. 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…

AI assessment note: “Well, that'd be Uber by far. The story behind that was”

Q 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 guess, what was the genesis for founding Long Journey?

A 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. It 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, because it was true sweat equity and putting it into something that was literally blowing up on launch pads 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 a…

AI assessment note: “I made my way into startups back in 1998, 99... my first check was into SpaceX”

Q don't know 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, a hundred to two fifty-k checks in them just doesn't make any sense at that point. Like, what do you make of multi-stage being so aggressive at seed?

A 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 A-Six, Z, 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. And they usually don't let angels in unless it's like a tiny bit, like 50 K or a hundred K 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 …

AI assessment note: “it's a strategy to cut out the seed ecosystem and other Series A investors”

Q 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 an experience, and I've been learning, and have you always trusted in your convictions, or has it come with time and success?

A 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.

AI assessment note: “I think I've always trusted my convictions, even before I was an investor”

Q 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 an experience, and I've been learning, and have you always trusted in your convictions, or has it come with time and success?

A 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.

AI assessment note: “I think I've always trusted my convictions, even before I was an investor”

Q the show. And both of them said about kind of how fast you ought to build conviction. It was actually the 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?

A Oh man, pattern recognition, I guess. I think that I am a very curious person and I talked 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? And a lot of the times I make up my mind about the person before ever hearing about the product within that 1:10 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…

AI assessment note: “One of the things I'm looking for is overcoming some kind of hardship”

Q don't know 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, a hundred to two fifty-k checks in them just doesn't make any sense at that point. Like, what do you make of multi-stage being so aggressive at seed?

A 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 A-Six, Z, 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. And they usually don't let angels in unless it's like a tiny bit, like 50 K or a hundred K 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 …

AI assessment note: “it's a strategy to cut out the seed ecosystem and other Series A investors”

Q I love that in terms of the genesis, and such a special team at Founders 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. Did it almost make it challenging post that?

A 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.

AI assessment note: “I became more bold rather than less. So I think that it definitely gave me fuel”

Q 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 the experience and I've been learning. And have you always trusted in your convictions or has it come with time and success?

A 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. When 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.

AI assessment note: “I think I've always trusted my convictions even before I was an investor”

Q 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 as a 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?

A 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 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 U.S. 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, 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 p…

AI assessment note: “Cash drop might be the most recently announced public investment.”

Q And some founders will say, I just want to make a shit ton of money, and I think this is Is the best way to do it. And I find the startup world kind of chastises it and kind of use 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?

A 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 wasn't 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. 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.

AI assessment note: “I don't think we should demonize it. I think there's nothing wrong with anybody”

Q I love that in terms of the genesis, and such a special team at Founders 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. Did it almost make it challenging post that?

A 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.

AI assessment note: “Not really, because I assumed I kind of buried that nut”

Q 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 the experience and I've been learning. And have you always trusted in your convictions or has it come with time and success?

A 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. When 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.

AI assessment note: “I think I've always trusted my convictions even before I was an investor”

Q You know, we're seeing pricing now at levels that I've never seen before. 25 pre's for seeds played by, you know, multi-stage funds when there's nothing there. And great for the entrepreneurial ecosystem in some respects. But I am interested now with Long Journey and investing again on your own. How do you think about and assess your own relationship to price and price sensitivity coming in at the seed?

A 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 of this company becomes a billion dollars, ten billion dollars, et cetera, because everything has a ultimate end point value. It's not infinite. And I think some people think that things are infinite, but if you actually count how many companies in the last 10 years have been worth over ten billion dollars, it's very few, right? 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. …

AI assessment note: “to be able to get those kind of returns, you've got to be more price sensitive”

Q 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?

A 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. There'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? 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 and somehow through osmosis gain 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 Whe…

AI assessment note: “I try to be very careful with what I say and how I say it”

Q that I am, I do have to ask that 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 rollercoaster 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?

A 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, 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 betwee…

AI assessment note: “sometimes the market tells you things and you should listen and not be as contrarian”

Q the show. And both of them said about kind of how fast you ought to build conviction. It was actually the 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?

A Oh man, pattern recognition, I guess. I think that I am a very curious person and I talked 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? And a lot of the times I make up my mind about the person before ever hearing about the product within that 1:10 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…

AI assessment note: “One of the things I'm looking for is overcoming some kind of hardship”

Q 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 guess, what was the genesis for founding Long Journey?

A 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. It 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, because it was true sweat equity and putting it into something that was literally blowing up on launch pads 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 a…

AI assessment note: “my husband talked me into putting it into high risk startups”

Q 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 about kind of this?

A Sure, it hurts. I've had days where, I'm just going to 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 cancelled, 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 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 that I was going to come back stronger because I was like, yo…

AI assessment note: “Sure, it hurts. I've had days where, I'm just going to be honest”

Q You know, we're seeing pricing now at levels that I've never seen before. 25 pre's for seeds played by, you know, multi-stage funds when there's nothing there. And great for the entrepreneurial ecosystem in some respects. But I am interested now with Long Journey and investing again on your own. How do you think about and assess your own relationship to price and price sensitivity coming in at the seed?

A 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 of this company becomes a billion dollars, ten billion dollars, et cetera, because everything has a ultimate end point value. It's not infinite. And I think some people think that things are infinite, but if you actually count how many companies in the last 10 years have been worth over ten billion dollars, it's very few, right? 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. …

AI assessment note: “you've got to be more price sensitive”

Q Do you not think that's where we are now?

A 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 they're, 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. 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, reall…

AI assessment note: “We're getting there. Yeah, absolutely. I think we have not seen the worst of it.”

Q And some founders will say, I just want to make a shit ton of money, and I think this is Is the best way to do it. And I find the startup world kind of chastises it and kind of use 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?

A 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 wasn't 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. 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.

AI assessment note: “I don't think we should demonize it. I think there's nothing wrong with anybody”

Q 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?

A 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. There'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? 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 and somehow through osmosis gain 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 Whe…

AI assessment note: “I try to be very careful with what I say and how I say it”

Q that San Francisco has enjoyed over the last many decades, actually, when you look back at the historical timeline. And when you look at the exodus 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 has had, or do you believe in the longstanding kind of future that it could hold?

A 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, 20, 20 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. 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. Well, of course they're …

AI assessment note: “Like there's a reason startups aren't staying. There's a reason that people are fleeing.”

Q Do you not think that's where we are now?

A 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 they're, 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. 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, reall…

AI assessment note: “We're getting there. Yeah, absolutely. I think we have not seen the worst of it.”

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

A Well, it's a very complicated past, 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. It's really interesting how people don't see that they're eating themselves. So this town is just literally eating itself. Would you be found 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 lik…

AI assessment note: “his parents are convicted murderers, and I think that probably shaped his worldview”

Q 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.

A Yeah, I think she understands it more. I think that her generation tends to be, I'm going to say 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, and 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, and the repercussions of it are going to be long-lasting, so it'll be really interesting to see what happens. But I learned 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.

AI assessment note: “Yeah, I think she understands it more. I think that her generation tends to be”

Q 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?

A 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 this 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. 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 n…

AI assessment note: “Diversity is the solution to that. So we have no diversity in politics.”