Cyan Banister on Her Relationship To Money

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, 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 ten or more years now. And when I first started investing, 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 gonna go work at AngelList for a little while and help Nabal 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, 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 AngelList and we all love working with Nabal and well, I guess that kind of sent the international signal that I was hireable because I think a lot of people didn’t think I was hireable. 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 Founders Fund is one of them.

And so the opportunity to work with that team for four years was just phenomenal. 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.

Not really because I assumed I kind of buried that nut, 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.

It’s funny because I used to hate money, literally hate money. Why did you hate money? 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 kind of unfair.

When you have that mindset, then kind of 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. 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 in 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, like 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. If I wasn’t an investor, you know, maybe I’d be doing other things. But I get really 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.

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, sometimes it makes people uncomfortable, but it often means that I’m the first check-in, 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.

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. Know, 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.

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 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 first ten 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 The journey to get to America is incredibly hard. And so that shows grit, right? To be able to 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 Cyan Care. 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, 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, 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 asked this question that means that other investors don’t, which I find weird. You know, we have this period 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 gonna figure out who the person is sitting across from you with those types of questions. You’re just not.

Well, 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, 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? 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.

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’re 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. 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, etcetera. 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 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 and so I think at this point, I mostly interview drivers to see who’s the happiest 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, 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.

Well, what’s gonna happen is there’s gonna 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 gonna be great. And so I think that will create some discipline in the market. So one of the things I love about my partner, 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 gonna take on? Am I actually going to do my pro rata? How does this play out if this company becomes a billion dollars, $10,000,000,000, etcetera? Because everything has a ultimate endpoint 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 ten years have been worth over $10,000,000,000, it’s very few, right?

Sure. 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. But what 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 $250,000,000 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, which is not as bad as as high. I just wouldn’t say bad, but as high as some other firms are. Some need 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.

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 sixteen z, etcetera, 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 multistage 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 100 k or whatever. And then the seed funds definitely 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 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. If the founder wants to have ten, twenty of us, then they have ten, twenty of us versus just one person. I think having one person and one fund can be detrimental because if they don’t follow on, you’re kind of dead in the water.

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.

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 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 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. 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.

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, 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 works, so maybe there’s some sort of magic to their dysfunction.

So it’s 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’ve 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, I actually get really excited about them. I mean, Collinsons 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 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.

Well, okay. So first of all, I’m pretty sure if 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 and 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 a 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. 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 a 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. 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, I’m not part of Antifa, 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.

I think that people hear and see what they want to see and what they want to 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, and I question things around me, and I don’t just accept the dominant narrative in any given thing. So, yeah, I’m gonna say something 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 messaged me saying, gosh, I wish I could have said this, I can’t, I’d get fired.

I mean, how horrible is it that we live in a time where you can say something that is a 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 a bad intolerant? I don’t think so. I think it’s miserable. Can I ask, does

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, 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 me. For 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, you know what, I’m not going to 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 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 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? 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, think that’s a really dangerous place where people are so afraid to speak that they double down on some of their bad ideas.

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. 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 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. 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.

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 centrist. 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, 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 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 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. 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. 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.

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. 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, could but 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, take home 30¢. Well, of course, they’re gonna 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, Chesa, who will not prosecute crimes. I just found out yesterday a friend of mine whose house was burglarized.

The perpetrators 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 gonna be prosecuted. So when you don’t prosecute crimes or you call them quality of life crimes, people are gonna move elsewhere where they feel safer and where they can defend themselves and their families.

That’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 Chesa 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. What do you think? 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. You know? So

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, maybe we can turn this place around.

Sounds great.

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 say my favorite book. It’s going to be very cliche, but it is what it is, which is Snow Crash by Neal Stephenson and probably seconded by Diamond Age by Neal 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 him 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.

You haven’t said Sapiens yet. I haven’t read it yet. I mean, I can’t say that because I

Well, I’m fascinated by what they’re into. I think that it helps me like, I understood that Roblox was gonna be a thing before it had its meteoric rise just by watching kids play it. So I think that there are 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 touch screens, with voice to text. Siri is actually a real thing in their world, whereas like a lot of grown ups, 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. 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 can be furthest from the truth for me. I love my kids fiercely.

Yeah. Think she understands it more. I think that her generation tends to be, I’m gonna 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. 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 our age. Kids were supposed to graduate from school and they’re 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.

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. But 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 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 me updates on the business. And basically, it was when I met Travis for the first time at an off-site 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.

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 ahold of Ryan Graves. And then that’s how the investment happened.

get so excited? 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 100% 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 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. 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 hotdog 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 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 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? 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, I 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.

me. Absolutely. Thank you.