Transcript of Lucy Guo’s Billionaire Playbook: Startup Secrets, Hidden Money Rules, and the Power of FOMO

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Do you think some of this changed? Obviously, youngest female, self-made billionaire, headlines everywhere?

I would actually say no. I think it really changed when I learned to become very confident in myself.

You've heard the Wall Street lore, the college dropout who made it big in tech, the founder who left a tech unicorn and built their own. But Lucy Gwo has lived the lore. She's a college dropout who co-founded the unicorn Scale AI. Now she's running passes. Today, she tells me about the wildest, scrappiest money stories you will ever hear.

He took my lap I sprinted out the door. Damn, girl. Yeah, and I caught him, I would say, a mile, mile and a half in.

And then what happened?

I just lunged myself at his backpack and tackled him.

God, Lucy. Money tips she learned after becoming a billionaire.

So what a lot of people do, I could take out a loan against my shares. And then I would be able to take out a loan at a very cheap price and then be able to make money off of that and never pay taxes. And then as those assets grow, continue to take out loans.

And what it's really like to work hard and play hard. I have an ex who closed a lot of deals at strip clubs, and I always wondered if there was an equivalent for women closing deals.

I have done diligence on companies at Constance & Raves.

You are going to love this episode with Lucy Lucy Gwo. I'm Nicole Lappen, the only financial expert you don't need a dictionary to understand. It's time for some Money Rehab.

Lucy Gwo, welcome to Money Rehab. Thank you for having me.

Oh, my God. You look incredible.

This is my DJ outfit.

I think that hanging out with you now is going to give me some cool points. I don't know.

I need all the help I can get. You seem very cool to me.

Thank you. Thank you so much. It's nerd cool, but I'll take it for sure. And you said that right after this, you were going to Berries, which you're- Oh, no, no.

I did Berries at 6: 00 and 7: 00 AM. 6: 00 and 7: 00. Yeah. So I do 6: 00 and 7: 00 AM every day. But I was just like, I woke up at 5: 55. I was a little groggy. I was like, I'm just going to pull the first thing I see, DJ outfit. So here we are.

I love it. We haven't had this much sparkles on the show, but you never forget your first. I did Berries yesterday morning in your honor, by the way. I love that. I'm not the the number one Berry's champion of the world. But when I show up, I do feel better. Yeah.

I think it's all about the effort you put in, right? As long as you put an effort, you're going to get that serotonin release and you're going to feel good because you tackle the challenge that day.

I mean, I had a baby last year, So thinking about vulnerability that Brené Brown talks about, it's not like livestreaming your bikini wax. It's showing up postpartum to berries. It was a very vulnerable experience.

Most badass people at berries are always a pregnant woman. I start them and I'm like, Oh, my God, you're You're pregnant, and you're literally kicking ass.

I love it. Okay, so you are all over the place, from double hitters at Berries to all the podcasts, to all the conferences, to all the things. Do you feel like you still work as hard as you did had hustled as hard as you did from before you were successful?

I would say so. My routine hasn't changed at all. I think I've always believed in the power of routine and waking up early in the morning to work out, to get your day started. And I think that There was at some point in time where I let go of that routine, and I felt like I wasn't working as hard because I wasn't getting as many hours in a day. But I'm back on that routine, right? And that was how I lived when I was first trying to build companies. And that's how I live right now, where every single day I'll wake up between 5: 30 and 5: 50, and then I'll get up, go to Berry's, do two double workouts, and then just go straight to the office and work.

I mean, even take me back to childhood, right? You grew up in an immigrant family like I did. I feel like there's a different mentality around needing to make money or the strive to make money. So you've always talked about the idea that making money was a goal for you, even back to like, Neo pets days. Where did that come from? From your parents?

I had Chinese immigrant parents, so they always emphasize the importance of education and money. But education was to make money, which is why in Asian culture everyone jokes that, Oh, my parents want me to be a doctor, lawyer, engineer, or else I'm a failure at life, because those are three well-known jobs to make money. I think where I wanted to make money really young, though, was the fact that I was bullied in school. I I've never had the coolest clothes or the cool toys, et cetera. And these are things that I wanted to get that my parents wouldn't get for me. So I figured out how to make money on the internet so I could get these things myself.

It's crazy because I have a very similar story. I've actually never heard anyone else talk about it. But when I was growing up, I was also bullied for wearing fake Doc Martens, and they were called Nurse Martens because I couldn't afford it.

I remember on the playground, someone told me, Hey, if you wore Abercrombian fit, she'd be considered cool, but maybe we'd be friends with you, but you're wearing Airpastel. In my head, Airpastel was this expensive brand, right? So I was just like, Wow, I splurged on this, and you don't like this? That hurts.

I mean, and look at you now, sister.

Well, I mean, this is actually really cheap. This I got in a Mexican. But it's how you wear it. Yeah, also true.

So how do you feel like that has stuck with you? Because even today, I've done a lot of things that people would find impressive. You have done All the things that people find impressive. But somehow the bullies from high school still get to me. I can talk to anybody, except sometimes when I hear these girls' names from middle school come up, I'm viscerally upset by it in a way that I'm not in my mind.

Oh, wow. That actually surprises me because I think I'm the exact opposite, where now I'm just so happy and so confident and so grateful, right? Every single day, I'm thankful that my life is how it is. And I also think my The mentality has shifted a lot to where when bad things happen to me, I just think it's a lesson that I need to learn. I'm like, Okay, this sucks. But I am just going to take this as a lesson, look at the warning signs, and I almost postmortem everything in my life, I guess. So I'm like, Okay, and then this isn't going to happen the next time because these are going to be the preventative measures.

I need to adopt that. How did you get this really healthy mentality?

I think at some point, I just became really happy. And I was like, Okay, I have this support system around me. I have the best friends in the who I would do anything for, and they would do anything for me. I think that hatefulness really does stem from jealousy at the end of the day. There's no other real reason to think about someone and just be so angry at them. It could be someone with a nasty personality, but you might still be jealous about what they have, right? So yeah, I'm just like, whatever. Haters are always going to be haters. You're doing something right if you have haters.

Yeah. I mean, comparison is the thief of joy, and it's also the idea of taking poison and hoping the other person will die because really it's poisoning yourself. Some of this changed, obviously. Youngest, female, self-made, billionaire, headlines everywhere.

I would actually say no. I think it really changed when I learned to become very confident in myself. And this actually happened back in when I... During COVID, I moved to Miami. And I guess I was always a little bit bullied within friend groups before Miami. And Miami was the first place where I received this extreme selfless love. I can't really explain it. I think it It was a new era for me. And I think also as my confidence grew and the energy around me was more positive, I was able to just start blocking out all negative energy.

Why Miami? I got bored during COVID. No, so not a tax situation.

Not a tax situation. I actually am paying... I obviously have my liquidation vent last year, right? And I'm paying all my California taxes. I had the opportunity to escape, but at the end of the day, I'm like, I think it's worth paying the taxes to be somewhere that you need to be, whether it's because it makes you happiest or whether it's professionally, right?

The sunshine tax.

Yeah, it's the sunshine tax.

When you surpassed this certain networth, did you feel like that added confidence or had nothing to do with it?

No, it didn't have anything to do with it. I was not really liquid until quite literally last year, a few months ago. But I felt this... I would say I turned much happier, literally in Miami, which was 2020.

Love that for you. You guys, field trip to Miami. Let's go. Was it weird when that headline became public?

I wouldn't say it was weird. I would say I expected it, but it didn't mean anything to me because for me, I'm like, Okay, this title is going to be taken over. It's whatever. It's not liquid. At least it wasn't at the moment. I believe that with anything illiquid, things can go to zero, right? So I was like, It's all paper money. But I would say it opened a door to new opportunities. I suddenly had a lot of DMs from famous people. Like who?

I can't say. But In a sexy way or in a business way? Because I don't get any sexy DMs. I'm sure you're not shocked, but I get businessy type DMs. Do you want to invest? Or that stuff.

I would say, obviously, mix of both. The ones I was obviously excited about were probably just old celebrity crushes. I love that.

Okay. My imagination is running wild. And with these superlatives that we hear around, like youngest billionaire on all of this, how do you feel about the youngest component of it? Because I had that early in my career. I was the youngest anchor on CNN or CNBC, and then I wasn't. It felt like a weird shift for me, that moniker. How do you think about that?

I think what I think about it is just it gives people hope, maybe, that they will achieve it one day. But in reality, you're going to have the title for a few months, and then someone else is going to take it, right? I think someone else is ready to take it. The Kalshi co founder, she's like, So cool. Yes. Won't let me invest in her round because it's close, but so cool.

But you tried.

I totally DMed her, and I was like, Hey, is the round closed? The answer was yes. But in the moment, because I think every single person is different. So when they see someone that looks like them, grew up in the same lifestyle as them, et cetera, they get hope. The Calchee co founder is very different than me. She was, I think, an immigrant. Valarina? Yeah. And that's just so different. But other people will relate more to her than they relate to me and get that hope. And I think that as new people get this title every few months, it just gives more of the world hope. And then hope drives a lot people, right? They work harder because if you don't have hope, why are you on this planet doing anything?

It's really interesting that you say that because I know that you've talked about not being a role model or not considering yourself a role model. But it sounds like you do know that you give other people hope.

I know I give other people hope. I'm not sure if I'm a role model, but I give other people hope, and I always try to give my advice in the bluntest way possible. I like giving back that way.

I think when people see those types of headlines, they assume that you have a billion in your bank account. So for people that don't understand the liquid, not liquid thing, can you explain? Because we talk about the idea of don't mourn paper losses or don't rejoice paper gains, but you really live by that, which is incredible.

Yeah. So I guess The best way to explain it for people is if you start a company, right, and it becomes worth, let's say, $2 billion and you own 50% of it, that $2 billion is dictated by whoever invested in it, but it's not really actually $2 billion. One person could decide, Oh, it's $2 billion, so I'm going to give you this valuation, when it could really, in reality, be worth zero. There's actually a lot of investors that are just stupid and they'll invest, let's call it 200,000 at multi-billion dollar valuation. The founder could literally say, Oh, now my company is worth a billion dollars, even though there's 200,000 in the bank. I think another maybe easier to understand an example is, let's say your family gifted you a bunch of Picassos, and suddenly you have billions of dollars in art, but you still have zero dollars in your bank account. And are you going to be able to sell those Picassos? It's like, you don't know how much you're going to sell it, when you're going to be selling it, et cetera. So it's very different when you have money and things versus actual cash.

Were people hitting you up for money after that? Because they didn't realize.

I would say people have been hitting me up for money even before I had a dollar, really. But yes, a lot of people hit me up for money constantly.

And do you lend people money?

I don't lend people money. No, that's a big no-no for me.

Oh, interesting. Or friends. Or sometimes when friends ask me for money, I give it to them and I just think of it as a gift. I write it off. Yeah.

I would say if a friend was homeless, right? What I prefer to do, which actually just recently happened, is I'm like, Oh, here's a room in my house. You can stay here however long you want, right? But if someone asked for, I guess, money, I usually ask for something in return, just because I think it's principle, whether it's like, Oh, will you be my PA for for a week then exchange for, let's call this, $5,000.

I've actually done that, too, with a friend. I gave her a token job. And I think that gives people a sense of worth, too, around it, versus just charity.

Because you never really want people expecting free things from you. And I do think that you, for the most part, can expect the money is never paid off. I've only loaned one friend money ever, and it's because he comes from a very wealthy family, and he makes a lot of money, just in his line of business, you need to reinvest it all, right? So he's always pay me back early and gives me a large percentage on top of the money that I loan him.

Okay, so you're like a bank. Yeah. He just needed cash flow, it sounds like. Yeah, exactly. It was more of a business transaction. But yeah, people say, decide what you want more, the friend or the money, if you loan friends money. So did you have a bad experience? You're just really cautious.

I would say I have gotten scammed by a friend. It was more of an acquaintance friend, but it was almost structured like an investment, but the investment was in a document as a loan. But he pretended to run this meme coin crypto fund and showed returns. He showed me a cold wallet with millions of dollars saying that if he lost the money meme coins, he would back it with that. It turns out he stole someone's cold wallet. So, yeah. What?

And so did you give him money? Did he give him money?

Yeah. No, it's a whole FBI case now.

Oh, damn. Yeah. I'm so sorry. Oh, it's all good. It makes total sense.

I feel lucky because I didn't give him my networth, right? But there were a lot of people, like childhood friends, that have known him since they were three years old, five years old, that gave them their networth. And that's much worse.

They gave him all their money?

All their money, yes.

Do you think you have a lot more people hitting you up for investments?

I do have a lot of people hitting me up for investments. I think I need to stay disciplined, obviously, to make good investments. And my thesis with investing has always I'm going to invest in the best engineers. When I go early stage, so my hypothesis is just like, they can live off of ramen until they give up, essentially, because otherwise, engineers don't need to hire the people. You can continue pivoting different ideas. I actually just had an investment in Exit where he tried ideas for a decade. It failed after failed after failed, never gave up, just lived inside an apartment in Oakland on a couch eating junk food, and he just sold his company to Anthropic. So decent return for me. I'm pretty happy. I'm very happy for him. And I think that's just like, I've had so many investments go that way where it looks like a dead company, and then the founder never gives up, strikes gold.

But you see that because you know what that's like. Exactly. To be a scrappy engineer. Exactly. Do you have an idea of an amount, like a fund, or you're just ad hoc?

So I have been doing it with personal money. That being said, it happened like a week ago, but I had an LP interested. It's just moving along. So it's probably going to be closed by next week. So I'm starting a new fund. Knowing you. $250 million fund. Yeah, let's go.

Hell, yeah, Lucy. Let's go. And proven founders, too. Get a lot more cred and get a lot more money. It sounds like you were raising for your next company and just sent a bunch of texts, which you probably couldn't have done before you had that successful. Exactly. Yes.

So that was just a blessing. I was like, okay, great. Because I was a little bit nervous. I was ready to fund. I was like, oh, my God, are my LPs going to be mad that I'm starting a new company? So the first thing I did was allow my LPs to invest before letting other investors in. And it was a whole mess. It was way oversubscribed. I think it was raising like 2 million. Ended up being 9 million.

It was very high class problems.

Yeah.

If someone's watching and they have an idea that fits this thesis, how can they pitch you?

They could just email me at luci@passes. Com. Or actually, I have a new one, luci@criticalmass. Vc. Is that what it's called? Yeah, we're calling it a VC. As of now, we came up with that name. When I say literally this all happened within the span of a week, I was like, well, I mean...

What can she not do, ladies and gentlemen?

What can she not do?

One or two LPs. Can they slip into your DMs?

Yeah, they can slip into my DMs. I actually read them and just send I like a Doc send. I like reading about the founder, too. So a LinkedIn and then a Doc send is nice.

Good to know. And AI doesn't have to be AI.

It doesn't have to be AI, but I like seeing how a founder uses AI in their daily lives to make running their company more efficient. And what do you think is the thing that's going to gain most traction within AI?

Because five years ago, if you had AI anything, I mean, you were doing AI before it was cool, but people would invest more because it was the buzzy thing. I think now potentially, prediction markets is the buzzword for investors. But where do you think there's specific residents? Agentic AI or what?

Yeah. So I think at the moment, boring industries that are implementing AI to be more are going to be the big killers. Ai is extremely good at repeatable tasks and analyzing long-form documents, for example. I think that Harvey AI legal. It's a huge, huge market. I think that AI is better at doctors or radiologists, looking at images and detecting cancer, et cetera. These tasks that require extreme memory, extreme computer vision, just analysis. The more data, if you enter an industry where there's tons of data, you can just pour into the software or into a model to learn from, you can 10X efficiency, right? I think that where it's going to improve is probably an industry I'm not even thinking of because I'm unaware of how the industry works, but very old industry.

Yeah. The boring. Yeah. The boring stuff. The more boring, the better. Yeah. And when you worked on the other side by taking money from investors, did you ever have a weird experience that you want to do differently now that you are an investor?

Honestly, my fundraising strategy has always been the same as a founder, which is cause FOMO. And then through that FOMO, jack up the price of the valuation.

I see. So cause FOMO, make them want. Be like, this is a rocket ship. If you're not on this rocket ship, you're missing out.

Kind of. But also just plant seeds without telling who you're talking to. So say, Oh, yeah. I would rather be like, Oh, yeah. I'm going to Sand Hole Road. I have a few meetings, so this day at this time works. Because then they're like, Oh, crap. Who is she talking to? Sandhill Road has all the best VCs. This is going to be a killer deal. I need to move fast. That causes FOMO. Even if you're not going. I try to time all my meetings around the same time. So then I get multiple term sheets at the same time and then make those term sheets bid against each other.

How did you learn that? Because it's an art. There are some people that are really good at fundraising, and then there are people that are really good at this 3D chest of playing people off each other.

I think it's a lot of it is psychology. There's the kickstarter method, where when 80% of the kickstarter is filled, it's going to get oversubscribed. People have a fear of missing out. The best advice I always give founders is start at a lower valuation. Say you're raising less than you want to raise. If you're trying to raise 2 million, say you're raising 1 to 1. 5, right? Because then you could say, Oh, there's barely any left. It's oversubscribed. And then for the next, call it 500K to let's say, you bump it to 3 million. So 1. 5 million that you try to raise, you can jack up the valuation, which a lot people do.

It's better to be low expectations.

Because if I tell you, Hey, I'm raising 1. 5 million. A whole million is taken already. You're like, Oh, shit. I don't have much allocation left. But if I'm telling you, Hey, I'm raising 2 million. I have 1 million raise. It's like, Oh, I'm not even at... I'm at 50 %, right? It's not that great.

Totally. This is what happened in real estate a few years ago, especially in LA. People would put their homes on the market for one point, something.

Because a bit more. Yeah, exactly. Yeah. But I think that's why you want to give a façade of, I don't need the money, right? Because that makes people more confident that you will make them a lot of money. I know.

It's so hard, though.

It's a kickstarter method because you don't need the money, but you do need the money.

Yeah. I mean, are there any other psychology tricks that you would give founders?

I'm not a psychology group. So I always try to pitch VCs that I'm not interested in first before I move on to VCs I am interested in just to get all the questions out of the way so I can give a much more complete data room, for example, towards the end. And then they're impressed because they're like, Oh, wow, you've really been diligent about creating this. And you have all the data I need. I don't have to ask you for more data. So you just want to polish up your presentation for, I would say, tier one VCs. So do that. And then another thing, I guess if I were a founder raising a seed round or even maybe a Series A, the kickstarter works especially well when you're going after microfunds or angel investors, because angel investors and microfunds a lot less diligence. A lot of times, like a microfund, so I would call this a fund size of anything below, let's call, $50 million. They don't really do diligence. They'll make a decision, write a check in one day, versus these more institutional VCs. It's their job to do a bunch of diligence, right?

So they may take two weeks before they wire you the money because they're making sure everything is criskost.

Yeah. So it sounds like get your wiggles out, like comedians do at smaller clubs, and they test out their material. Before hitting the Comedy Store or whatever. Now that you're in, I don't know, is it like a billionaires club or like, successful people club? I don't know how you would call it. But now that you're there, are there any financial truths that have been gatekept by the rich?

I don't want to call it gatekept. I feel like this is just something people know, right? But obviously, if you take loans out against your assets, you never really have to pay taxes. So what a lot of people do, and I would I'm going to clarify, I was not able to do this because my company got bought. So then I got a cash payout. And with that cash payout, I actually have to pay taxes on. But let's say it never got bought and it just entered the stock market. It went public. I could then take out a loan against my shares, and then I would be able to take out a loan at a very cheap price, probably just like SOFA, which on average-It's like overnight lending. Yeah, overnight lending. Super cheap price, probably on average, I don't know, 3 to 5 %, and then be able to make money off of that and never pay taxes. And then as those assets grow, continue to take out loans. So that's what a lot of people do. I mean, it's brilliant, but yeah.

We've done a lot of videos and I was about this idea, I found out about it the more successful I became, because I used to think when I had credit card debt when I was growing up and being an immigrant's daughter, I didn't understand this space. It was like, if you don't have cash to buy the house, you don't buy the house. You don't buy the car, you don't buy the thing. And I always thought debt was a bad word. But then the more successful I became, I realized that rich people use debt as leverage. So let's explain this. So you have a portfolio, let's say, a million dollars. Instead of pulling out 200K to put a down payment on a house, rich people will borrow against that portfolio so they don't sell, they don't realize capital gains, and then they use that debt and they pay the- Well, I could do it that way.

I would say with real estate, almost everyone does it with an actual mortgage. But yeah, if you had... This is actually a really good example. Let's say you had a bunch in a stock market right now, and then you were able to take out against all your assets, let's call it your home assets, your art assets, etc. Take out, let's call 50 million, safely, because you won't get margin called on 50 million with how much you own. You could put that 50 million into a private stock company like Anthropic, where you know within a five year time span is probably going to 3X. And then you're paying very, very little interest on this with email. And then when it 3X is, you not only get to write off the interest, but you get, yay, the profits. Yeah. And then you can pay back the loan and call today.

I heard that somebody tried to rob you, right? Or break into your house. What happened? Oh, yeah. You feel like a target on your back?

Yeah. So now I have a lot of armed security. But back then, I didn't. And what had happened was I was in Vegas, and I just posted real-time like, Oh, I'm on my way to Vegas. So someone knew I wasn't home. And then they came to my house and they broke the glass window and then tried to rob me. But my friend was home, and he scared him off.

Oh, my God. Yeah. And you have an amazing person here with you today, but you're not rolling super deep with armed guards right now. Do you have bodyguards?

Yeah. So I actually had an A-list actress ask me this the other day. And I was just like, I think the difference between me and you is that you get paparazzi and followed and recognized, right? No one cares about tech billionaires. I don't think Mark Zuckerberg is getting paparazzi. And if he is, I'm sorry, Mark. Brian Chesky, I'm pretty sure he lives in LA. No one's following him around. You never see him on the news. And these people are much, much wealthier than me. And I do think it's just like, oh, we're tech people. We're tech nerds. No one cares about us, which is great because I don't feel the need to walk around with a bodyguard I actually think that makes you more noticeable. The best bodyguards are ones that are more incognito. They look like a friend or short, tiny. They dress in normal clothes.

That situation scare you? Are you worried about safety?

No, I'm not worried about safety because at the end of the day, if I get robbed, what's going to happen? I don't really have that many nice things. You could rob me and you're going to be sorely disappointed. I don't have expensive art. All my really nice stuff is locked up in a bank vault. I have nothing. I mean, your computer. I do have my computer. Yes, I have had my computer I've stolen once at Starbucks.

That's right. But now I'm assuming... I mean, you forget more than I will ever know, but sharing it's all backed up and everything. Yeah.

Well, I mean, I got my laptop back. I chased a guy.

Stop. Yeah. You ran after them? Yeah.

It wasn't really stupid. It I was a really stupid decision. Looking back, I was like, Oh, he could have had a second guy, and they could have punched me or whatever. But it wasn't the laptop itself. It was just everything on my laptop that I needed, all my work. So I had actually just done two berries classes that day, and I was at Starbucks just working. And And then he took my lap up. I sprinted out the door. Damn, girl. Yeah. And I caught him, I would say, a mile, mile and a half in.

So he was sprinting and you were sprinting after him? Yeah. And then what happened?

I just lunged myself at his backpack and tackled him. God, lose it.

That's insane. I mean, let's go back to some of those days, the scrappy wild days of Vegas. You've done some pretty unhinged things to get by. Tell me about eating for free?

Well, there's a few things I did to eat for free. So I would say, yes, I lived in Vegas and I would just go to the lounge. I would book a Southwest ticket and then check in, get in, cancel a ticket because it's fully refundable, and then go eat. But I've also done other things. It was a running joke that your tech company, you could get free food through VC-funded tech apps. So I'd find all the new food apps that VCs were funding. And I would just post my referral code on different coupon websites, and then people would use because everyone's looking for a discount, right? And then I would just rack up literally thousands of dollars in free referral, free credits, and then just eat for free.

I mean, you've talked about being a really big believer of the fire movement. Do you still want to retire Are you ever retiring?

No, not at all. I tried retiring. It's so boring.

You're never retiring.

I don't think I'm ever retiring. I can see myself doing different things. Maybe I stop building startups. I think VC is actually a more relaxing life. So maybe I end up doing full-time VC. I do a family office. I go into foundation work. But I think I always need a work because I get happiness off of my brain running and solving problems. That excites me and gives me this serotonin, adrenaline rush. I remember I was traveling around the world. I was so happy because I love meeting new people, making new friends, learning about new cultures, seeing how beautiful the world is. I still have great memories of just being on top of a mountain by myself and just be like, Wow, this is really pretty. But I was lacking that serotonin high I would get from solving problems, and I think I need that for the rest of my life. So here we are.

Here we are. I mean, that's priceless. That's something you can't buy. Yeah. And so you tried to take a little break after a big liquidity event, and you just thought it's not for you.

Well, this is actually not after the cool day event. I was like, okay, I think I have enough to do... It was a mixed view of Fat Fire, Lean Fire. I was like, I could be comfortable, right?

Tell me the difference, fat fire, lean fire. Lean Fire.

Lean Fire is retiring off of very little money, and fat fire is retiring off of more money I guess, and living a more grand lifestyle. But I also have little hacks to live grand lifestyles, right? So I was like, Okay, let me just... I don't care about where I live. So I bought this $70,000 apartment in Sexton Airport. Sexton Airport? Yeah, Sexton Airport. It's two bedrooms, two baths. Yeah. I don't know, 2,500 square feet. It was next to a bunch of homeless people. And there is a hole on the roof now because I think someone broke in and was living there because they started getting utility bills again.

Wait, this is your hack to live a luxury lifestyle No, no, no.

That was how I was able to reduce my rent cost.

I see. I see. I see. Like your main nut. So then I could spend everything else on my luxurious lifestyle. I see. So live in a shithole and then- And then, yeah, you could do like, rent a churn, but then also- Charter your job.

Yeah. Let's say you wanted to fly for free first class everywhere, right? Just go to the airport lounge and start being really friendly to every airline employee, and someone could list you as a buddy, and then you get to fly for free everywhere. Has that happened to you? Every time I talk to a flight attendant, I always make a joke like, Oh, yeah. Do you want to list me as your buddy? I'm still trying to get Jet Blue right now. But yes, I have been airline buddies.

So they can just list you and you'll get upgraded?

Oh, so then they can list you and then you could basically fly first class for free. Yeah, because you fly on standby, but then you get upgraded to... You book business, right? And then you go fly business for free.

How many buddies can they have?

Usually a few. Yeah, you can list your parents, buddies, siblings, three gentlemen.

They are into getting deals? I love for things. No matter what's in your bank account or what you have in your paper.

No, it's a running joke in the office that I love buy one, get one free because Bogo is the best. Yeah, and I was telling My friend was asking me, How do you discover good restaurants? I'm like, Oh, so I literally go on Uber Eats, I click on the deals, I find a Bogo, and then I go on Yelp and match the restaurant and dish to see if it looks good and it has good reviews. And if so, then I try it. And if it's good, then I go to the restaurant and I try other items. But I find all my new food through Bogo deals.

And do you think that's always going to be the case?

I think so. And the reason I think so is I think that people that make their money really understand the value of every dollar. And then from that, they really value when they can save money.

I agree. I had a small negotiating win with a vendor that I was so, so excited about. It was $20 or $30. But for me, it just felt like a win or something that I was for less on this fiber person.

Even when I had a few million, I was still riding Uber Pools, and I was using a McDonald's app to save a dollar or whatever. And my friends thought, I was batshit crazy. They're like, Dude, your time is more valuable. I can't believe you're still riding Uber Pools. And I'm like, Why? I don't feel like I'm really wasting time. I can work on my laptop. I'm a great conversation with the drivers and the riders. So yeah, I think I've always just been somewhere where I'm like, okay, I still ride. I try to optimize for what is fastest, but also look at the price difference on Uber. I'm like, okay, cool. If it's like $30 versus $60, I'm going to take the $30 ride even have to wait longer. But if it's like, 30 versus like, 40 and the wait time is the same, I'm going to take the Uber X over the comfort.

Yeah. I mean, look, there's the saying that rich People stay rich by acting like they're poor and poor people stay poor by acting like they're rich. And I think that if you want sustainability, you can't ball out on everything. Exactly. Maybe you can get anything, you can get everything.

Yeah. When I spend money, it's usually for comfortability or if I don't want to do a bunch of layovers and sit not a lie flat, I will consider getting a jet. But otherwise, I prefer just... Or if I don't want to be around... Because I'm girl. And I know I'm in a scene, so I can always get free tables. But I'm like, If I'm at a promoter table where I have to talk to a bunch of dudes I don't want to talk to, I'd rather just get my own table.

You go out a lot, as you mentioned. Have you ever closed a deal at a concert or a rave?

I have done diligence on companies at concerts and raves. Not to my knowledge that I can remember in my head, have I closed a deal.

Because I have an ex who closed a lot of deals at strip clubs, and I always wondered if there was an equivalent for women closing deals.

No. That actually fascinates me, too, because I hear this, too, where businessmen, specifically, will go to strip clubs or just clubs in general and close deals. And it was just so icky to me. What?

Yeah. I mean, there's also sweat working, which I'm sure is up your alley, too, where people are taking runs or walks while they're having a meeting, so they're getting their.

That being said, I will say I think that people... There are people that do close deals at music festivals/raves. And I think it's usually the DJ themselves. So let's say you're a DJ and you have a venture fund.

Which is crazy that that's not uncommon.

Yeah, it's not. It's so common. But there are DJs with venture funds where they'll be like, Oh, let us in the deal and we'll let you backstage, on stage, and show you a good time. Does that work? Oh, fully works. Because I think you have these founders who they love EDM music. I think a lot of founders like EDM music. My hypothesis is that we were really nerdy growing up. We probably went through a depressed phase. And the BPM of EDM literally opens up the heart chakra and makes you all happy and joyful, right?

In your throat chakra, too, because you're screaming all the anger and all the whatever pent-up stuff that you have.

I don't know if you're screaming, but you're definitely singing. But yeah, I think Yeah. Then they get so struck. And then- That's how I say it, is by screaming.

But it's true. And also sports, too, which is why a lot of deals get done for courtside tickets or getting into minority stakes of sports teams and stuff like that. Because I do think, yeah, it's like- Yeah, I actually think sports is probably where a lot of people do deals to.

I can see that at games. We take people out to games when we're trying to, not close deals, but build relationships, stronger relationships.

Do you think there's a stigma around people who work hard, play hard?

So I think the world is very sexist, and I think the stigma only exists with women. And I say this because I'm biased. Am I salty that I have this stigma? Yes, I think that people are like, Oh, she's a party girl, whatever. She doesn't work. And I'm like, I'm just awake more hours in the day than you. And I actually am in the office longer than you. And on my laptop longer than you. I wake up earlier than you. I sleep later than you. I'm sorry that you did not get born with a gene where you need your full eight hours of sleep. That's not my fault. Do you have that?

The gene that you don't require sleep? Because that's the thing.

I would say, according to my eight sleep, I have pretty high recovery, even when I sleep five hours. I would say I was a lot stronger, younger. Younger, I could do three hours and be fine. Now, I would say five hours, I feel great. But if I'm on 4, I'm not happy. I'm really not happy on 4. But all the guys in tech I know, they're party animals. They're crazy. I think they're a bunch of public examples out there. Their tea has been spilled, but also privately, ones that you don't hear about as much. They are doing everything possible, imaginable. They're out at 4: 00 AM on Tuesday nights, mornings, I guess. And nothing. Nobody says a thing.

I was so surprised by this. When I lived in New York, I saw it more. Guys would be out, guys more, four o'clock, whatever, than going running in morning and then to work. I feel like there are some people that are just superhuman in that way. Now that you're so deep with passes in the creator space, what have you learned about the fees? Or where do creators get tripped up by not earning what other creators are potentially earning. Oh my God. Or I know you've talked about this idea that people shouldn't sign these 360 deals with managers.

Yeah. So 360 deals are terrible. I think I'm learning that some people have extremely predatory contracts. I can just go through red flags where, let's say, a manager takes 20 % of a deal, but then if the brand doesn't pay the creator, they still owe the manager the money and the manager can collect from them. That's some of the more predatory things I've seen. I've seen managers quite literally steal money from creators, where the creator might be getting offered $20,000, but the manager only gives $5,000 out of that $20,000, or they keep all the upside in a deal. I think my main problem with the industry, though, is that they think very short term, and I think Hollywood is very cash hungry. So they're not thinking about the long term of a creator. And it might even be how agencies are structured, right? You have to get, let's call it, a million dollars a quarter in brand deals for creators. So it's not Yeah, the quota. So they're not thinking about the equity upside for creators, which I think really matters just for both long term generational wealth, but also when companies are giving creator...

When companies are using creators, they're betting that the creator is going to be cheaper than any other marketing spend they can do. And that's because creators don't have the typical customer acquisition costs when they promote a brand because they have followers that convert better than ads. So I really do wish that this equity component were included. So creators can... Certain creators might actually just bet on themselves and then take equity in a company like Alex Girl with like, sip marks, right? Like she bet on herself with equity. And I think you're seeing a lot of creators do this, both with incubating brands with other companies or taking profits from an entire line.

I don't know why managers wouldn't just utilize the same percentage for the equity. If you got a point or whatever, couldn't they take 20 basis?

Yeah, so they could. I think that it's not valued in Hollywood. The ones that really do value it got burned from it before. So I've met a few influencers, celebrities, whose agents turned down the equity deal for them, and then they lost hundreds of millions. And then they're like, Oh, fuck, we need exchanges. Now, those are actually the people that I've met that ended up creating their own companies. And then they're now worth hundreds of millions. But I think once you realize the power of equity, you really value it. But because most people never really understand it because they didn't... You never really understand it until you lose it, right? And then you're like, Crap, that FOMO hits.

And to be clear, the 360 deals deals are basically where they're commissioning off stuff that they didn't book for you. Oh, yeah.

So many people are in these 360 deals where even if you started your own brand and you were making money from it and your agent had nothing to do with it or your manager had nothing to do with it, they still take that 20 %. And I have friends that have music managers, and all that manager does for them is music, and they take 20 % from everything else they do, which is super unfair. And their manager's argument is like, Well, we're making you bigger through music, so we deserve 20 % of everything you do. But I just like, I don't think that's fair.

It's not right. There's this old South Park skit that's like... I'm sure the writers were pissed at their agents. They were like, If you have all the talent, do all the deals, make all the connections, we'll be the best agents in the world. If you If you just handle everything. Yeah, I mean, I've gotten myself into bad situations with agents and managers. It's hard. And I think that I didn't realize early on, but I did later when I had some weird stuff happen with agents that tried to commission stuff that they didn't do. I fought back with them. And so I think sometimes creators think that just because they get a bill, they have to pay it. Or just because they got a scary email or a letter.

Yeah, and the better ones will negotiate, but there are some that immediately jump into lawsuits. It, which is not great. Not today. Yeah. I had a friend that their agent was collecting their money on their behalf and sending it to them, but also handling their rent, their bills, etc. And then he found out his agent was selling money when the landlord called and was like, You haven't paid rent in three months.

Yeah. I hate that. Yeah, it's crazy. With Passes, I know you have said that there will be a unicorn creator. Will that happen in 2026?

I don't think it'll happen in 2026. I'm going to be completely honest. I think that if I can make a unicorn creator in the lifespan of this company, I'll be very happy. So let's call it the next 10 years before it goes public or it gets acquired. But we are starting to incubate some brands. So I'm excited.

If somebody wants to be a creator or join Passes, what's the process like? And And if somebody is now just waking up to the idea that maybe a creator, a lifestyle, or career is for them, do you think it's ever too late?

I never think it's too late, especially now with TikTok and Instagram reels. Discovery has become a lot easier. So you can gain followers pretty quickly. And I think there's just certain scripts you can do to gain followers. I always tell people the best way to gain followers is probably just do a part 10 series and write a script or copy one of the scripts on TikTok. The difference between followers and fans, though, there is a pretty key difference. And that's are they interested in you as a person? Do they want to stalk you, talk about you outside of your TikTok and Instagram comments? And that's actually what we evaluate when we see if someone will do well on passes or not. Are you being talked about on Reddit, Discord channels, Telegram groups, forums, etc. Because that means that you have real fans or are fan pages making videos and collages of you versus just interaction on your page. Because it's so easy to comment like, So hot, so So Pretty Ha Ha, that was funny. But real fans go one step above, right? So I would do a 10-part series and then start doing live streams to showcase your personality, throw in a random videos also that showcase your personality to become an influencer.

And then to join passes, really simple process. You just apply and we review your application, check you're a real human, and then we accept you. And then depending on how many followers you have, what your earning potential is, we'll have someone in the company reach out and really hold your hand while setting up your profile and setting up launch day, et cetera.

So if you join, you then get a lot of monetization tools. Where did you see the system was broken around monetization for creators?

I would say it was probably around COVID. At the same time, I got really I was really frustrated about brand deals and equity because I had a lot of creator friends, and I was like, Why are you guys not taking equity in these companies, guys? And over COVID, I had a lot of friends where the brand deals dried up. And then around the same time, Patreon raised $4 billion evaluation. I was like, Holy shit. There's probably something here. I looked at the monetization tools they had. And it was pretty bare bones at the time. Sorry, Patreon, you guys have done a really good job improving. I was like, Okay, great. When I look at what tech companies to build, I think that the best tech companies are when there's a stagnant product that's lacking innovation. Startups do better than these large companies like Google, Facebook, et cetera. They're able to come in because they're able to move faster. I saw an opportunity to move faster and build more tools deals for creators to monetize. And I think we're also thinking of it very differently than Patreon, where Patreon's entire motto is like brand deals aren't paying you enough.

So monetize with your fans and have consistent income. And ours is like, have that, but then build generational wealth. That's the approach of how we've taken it and how we're thinking about the 360 of the company.

What do you think the future of the creator economy is?

I think the future of the creator economy is that it's going to grow for sure. When you talk to kids these days, they all want to become creators. I think that's a good sign that is growing. I think that people are going to care a lot less about just how many followers you have, what engagement you even have. And it's going to be more based off of how can you convert, right? So people are going to start measuring superfan communities because I think it is a direct correlation to Will this person be able to actually influence product sales? And then I think AI is actually going to have a much larger influence than people think. I don't believe in AI creators because fans are emotionally attached to creators, right? And there is no emotional attachment when it comes to an AI creator. You can't really relate to their life. You don't get excited to see who they're dating, etc. Because it's just not real. That being said, I can see for certain brand deals, it might make more sense to license out your likeness to a brand versus having to fly out for a week, set up a production studio, and have to have makeup artists, video editors, et cetera.

Ai is going to be much cheaper at doing that. And as long as you don't dilute your brand, so you don't work with a hundred different brands. You're going to be able to get paid relatively the same. I think that, yes, you'll make last be able to work with more brands and expand your time, scale your time. But you'll have more time to now reinvest into your content and interacting with your fans and growing an even larger fan base.

What would you just say to somebody asking for a friend who's nervous about showing more of their personal life? Do you think that that's a necessary ingredient to becoming successful I think you either have to share a lot of knowledge and people will latch on to knowledge, which is why all these finance podcasts and TikTok, et cetera, do so well, because they're like, Oh, I learned something.

Let me follow and continue to learn things. I think you can be successful off of creating story lines and scripts. Those mini TV series on TikTok, those do well because that's entertainment. And then you can be successful off of being very personable. But I think being personable is one of the most important things if you want to build a brand. Because if you do these... For example, there's a lot of actors and actresses out there, right? But not all of them are going to be able to build a killer brand because you might be a star in a movie. But if you're not personable, no one really cares about you. And I think... I'm trying to think of examples. I don't really want to throw anyone down, but there's creators who's tens of millions or hundreds of millions of followers that can't convert at all because they might have them. They might have great engagement because they're hot or whatever. But no one really cares about what they're saying, versus Taylor Swift, right? People are obsessed with her because her songs are so relatable. She's made it a point to interact with their fans, et cetera.

People love her.

Myself included. Yes. I think that's probably the North Star of- She's a North Star of fan obsession. Super fan. What do you think the big trends are for this year? I know Gary Vee talks a lot about live shopping being the next live streaming. Where do you see Where's it going?

Live shopping, yes, that's going to be trend. I think these other things, I want to say creators using more AI tools to create content or selling their likeness or licensing not their likeness, et cetera. But at the end of the day, I actually think AI tool adoption is going to be a lot slower than we expect amongst the creator community because we had that new AI actress pop up, and everyone's freaking out. I think it's going to explode once creators realize and everyone in the creative industry realizes AI is not going to replace them. But at the moment, yeah, I'm curious. I guess one consumer trend I think is going to happen is, and I don't know if it's going to be 2026 or 2027, but I think it will happen relatively soon. Is vertical movies and TV shows.

Explain. So off streamers.

Yeah. So right now, everything is horizontal, right? When you watch a movie, it's horizontal, et cetera, et cetera. I think we're going to get full-length films, and I think Netflix will adopt too.

Like broken up.

Yeah. I think it'll be part-based. I think that we're going to see maybe interactive movies and TV shows and videos. But I fully think that it's going to go from a horizontal format to a vertical format.

You've been on a lot of shows. What do you wish somebody asked you that didn't?

I don't know. It'd probably have to be more of my crazy lifestyle, things I do for fun, I guess. I think that I'm interesting in the sense of I I have no sense of fear at all. So my sky diving license. I ride electric plong boards. I have my scuba diving license. I went nighttime diving without ever being trained. Apparently very dangerous. My motorcycle license. Don't try it at all. Yeah. I guess I just... I think I have a lot of outside interest outside of business. I think I have a very multi-hyphenate, very different personality types because of that. Yeah.

I mean, when we assess in the finance world, called risk, you look at those factors, too. So it's not just risk tolerance within what you feel like the stock market is going to do. It's like, would you go to sky diving? I mean, you exude risk tolerance. So 360 in all aspects of your life. And because, of course, we're at money rehab, have you felt like you needed money rehab or made financial mistakes that you can help advise others not to make?

I would say my main financial mistakes I have personally made are buying apartments because you don't own the land. So it almost never goes up, right? And then you have to pay a fucking HOA fee. I say this because this is probably does relate to the audience. You always want to buy a single family home so you own the land. Very rarely are you going to make money on an apartment after you have property taxes. And then when you resell it, you have to pay a real estate agent fees, et cetera, et cetera. Almost always a house is going to be a better investment. I can't even think of an apartment I looked at where it would have made me money. I should maybe there's one in New York. But at the end of the day, HOA fees are also uncontrollable. They can always rise. My HOA fee is literally over doubled after being promised they wouldn't. And then there's just so many rules. You don't want that. So single-family homes only. But also when you buy a single-family home, you really have to hold it for a while. Otherwise, you're probably going to lose money on it.

And I think that above a certain price point, it's just not I love it. I think that my LA house, I'm actually going to lose money on. Why? Maybe look at the historicals of LA mansions over the last decade. They don't really go up in price. It's pretty flat-lined, I'd say. Not to mention that the larger the house, the more problems it has. It breaks every single day. And so do my friends' houses that are large. That's just a problem with large houses. And then then you need to get a house manager that you didn't factor into the cost. It's just a I think that anything like 5 million and under, if the historicals look good, you can make money off of it. Amazing. But when you start going higher and higher, you buy the house knowing that you're going to lose money. Not to mention that now you're locking up money because even if you do get a mortgage, you're still having to put a down payment on. That money could be reinvested elsewhere. Renting, from what I found, is actually almost always cheaper. I always see all the other goals going like, Home ownership, My Key to freedom, et cetera.

And then I think you really need to do more research on what apartment or house are you looking at? What's the area? What's the historical look at the last 10 years? And then factor in other costs, like maintenance costs, property taxes, et cetera, insurance, because I would actually argue most of the time you're saving money renting.

I argue that all the time. We argue that on this show a lot because if you look at actually just the numbers, it's not a good investment. Maybe you're getting the home because it's an emotional thing or stability. I saw my house foreclosed on when I was a kid, so maybe I want a home or something like that, which is just as valuable and just as important, but it's a different conversation than a strictly financial investment conversation because it's growing four and a half % year over year, which is less than putting your money in VEO. Exactly. Okay, so we talked about a mistake or a misconception in finance. We end our episodes by asking for a final tip that listeners can take straight to the bank. Is there something that you would suggest financially?

I just have such different risk tolerance where I prefer going all in versus playing it slow and easy. So for example, if I had only $100,000, I'd probably just be like, Okay, let's just put it in Amazon and call it a day and close my eyes finally. Because if you're going to just go with the S&P, yeah, it grows. But you're never going to make a lot fucking money, versus if you go all in on something, you have the opportunity to make a lot of money.

I mean, higher risk, higher reward, right?

Yeah, exactly.

It goes in parallel.

So I guess for me, my financial advice, it would be really different between on someone's risk tolerance. So I'm the type of person that really does go all in, which is wide. It's startups, right? I left a multimillion dollar job to be able to have the 1% chance, less than 1% chance of building a unicorn. And it worked. That being said, I think that the smarter piece of advice would probably be put maybe 70% of your money into S&P because it's always going to grow in return. It does beat every hedge fund when you look at it long term. And then maybe put the other 30% in riskier investments, whether it's Bitcoin, whether it's your friend's company that you really believe in. I think if you are, very specifically, if you are deciding to go all in on a startup hoping that you'll succeed, what I would personally do is, I hate to say it, but there's a reason why in VCs. People do follow. We're considered cheap and we follow tier one VCs because they do make the best judgments and have the best calls at the end of the day. So if you see a company that, let's call it, went through Y Comnator and Sequoia invested within them.

It's in them, and it's in the AI space and the founders went to MIT. Chances are, worst case scenario, they'll get acqui-hired and you're still going to make a return, and a pretty good return. Just put the 100,000 in there. Put your other 30,000 in there and call it a Close your eyes.

If you have your risk tolerance.

If your risk tolerance is there.

And you mentioned being in corporate. If somebody works at a Snap type company or if they're offered some equity package, where do you see mistakes made around that or knowing what that should be, options, what are the questions that you should be asking?

So what I've seen is a lot of people just get a dollar amount of like, this is how many RSUs you're getting, but you're not understanding, okay, at what valuation, how many shares is this actually? Which isn't great. Other times you'll get an offer saying, Okay, you have 2,000 shares, but you don't really know what the value of those shares are. And you should always ask these things to clarify so you know an exact amount of how much you're actually getting. And then outside of that, I think a big mistake I see is that if you're at a startup that's not public yet, just take the lower salary. I'm going to assume if you're at a startup and you probably are younger and you don't need the safety net of a larger salary, you don't have kids to feed. And if you do have kids to feed and you're joining a startup, chances are you are already successful and have a savings and you decided to finally take some risk in your life. So I always say, as long as you're below a Series C, like Series C and below, take the larger equity package.

Well, one of our most popular episodes actually was understanding private company equity and asking those questions about how many shares are outstanding or liquidation preferences or stuff like that. Because I think, to clarify, yes, equity can be better, but it's not always. And it's also never always going to hit the moon or whatever, because I think they see- And you'll see your strike price if you're getting shares, et cetera. You mentioned putting it 30 % potentially in riskier assets like Bitcoin. What's your latest take on crypto? How much crypto do you have?

I actually have no crypto. No crypto? Yeah. So I mean, I had some crypto, and then I forgot. I don't know where my wallets passcode are. So I now have no crypto.

And for the- But didn't you get Bitcoin at like 100 or something?

Yes. I got Bitcoin at 100 when I was in high school. Crazy. Wasn't I? I've had wallets? I don't even know where my wallets are anymore. It's funny because I always see people trying to hack my Coinbase, and I'm like, I have nothing in there. You don't have to go in my Coinbase. Yeah.

And then I did- You can't get it back?

No, I made a bunch of different MetaMask wallets, and I'm like, Oh, whatever. But I never really had that much. And I did recently. I was really stupid a year, but I down on this app called MoonShot, and I was like, Oh, like meme coin investing. Let's try this. And I was making so much money on meme coins. And then I got a text going like... I was literally running on a treadmill and it's like, Okay, put all your money in Rizmus right now. And I was like, Whatever, right? It was gambling for me. And like I said, I was willing to go all in. So I put all my crypto into Rizmus. Anyways, it tanked. Went to zero.

So now you're out.

Yeah, I'm out. But who knows? Maybe Rizmus will pop up this Christmas.