This Week in Startups - Sophia Amoruso on branding, raising a fund, portfolio construction & more | E1684

Episode Date: February 23, 2023

Sophia Amoruso, Founder and GP at Trust Fund, joins Jason to discuss her angel investments (1:23), raising a fund publicly (5:54), and the creative process (12:14). Then, they discuss portfolio construction and putting past identities to bed (27:04). (0:00) Molly kicks off the show (1:23) Previous angel investing experience (5:54) Why Sophia is raising a public fund (10:45) Linode - Apply to Linode's Rise program for up to six figures in discounts at https://linode.com/twist (12:14) Branding and the creative process (20:55) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (22:25) What stage of investing is Sophia going after (27:04) Portfolio construction (37:16) Brilliant.org - Go to http://brilliant.org/twist to start your 30-day free trial today and get 20% off your annual premium plan (38:44) Pro rata rights (46:56) Putting past identities to bed (1:01:18) Fund cycles (1:05:17) Investing in founders or investing in ideas & more FOLLOW Sophia: https://twitter.com/sophiaamoruso FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

All right, everybody, welcome to Thursday. The week is almost done, a short week for a lot of you, but we have a great interview for you today. I'm going to be saying that a lot over the next couple weeks, but I mean it every time. Today, we have Sophia Amoroso of Nasty Gal and Girl Boss fame. She joined Jason, not me, to talk about raising her first venture fund, which she's calling trust fund, breaking into the venture capital industry as an outsider with a unique skill set and her approach to branding and design much more as well. It's a fascinating conversation. A great interview. It's going to be a great show. Stick with us.

This week in startups is brought to you by Linode. Apply to Linode's Rise Program for founder-led early-stage startups and get a $500 credit up to $120,000 in infrastructure credits in year one, cloud consulting, and so much more. Apply at linode.com slash twist. Lemonio need to speed up your product development without draining your budget. Hire vetted engineers from Europe at Lemon. I. Go to lemon.io slash twist to get 15% off for the first four weeks. And brilliant.org. Brilliant.org is the best way to learn math science and computer science interactively.

Try everything Brilliant has to offer for a full 30 days and get 20% off an annual subscription at brilliant.org slash twist. All right. Sophia Amaroso is here. She is a serial entrepreneur content creator, author, and now she's raising her first fund called Trust Fund. Get it. Trust Fund. You're so good at branding. Thank you. Trustfund.vc if you want to check it out. Second time on the program, last time was four years ago, 2019, episode 962, if you want to go back. For those of you don't know, she founded Nasty Gal, the clothing retailer.

And she wrote an amazing memoir, Girl Boss, that was made into a TV show. and she did some girl boss rallies, then you did, what was your school? Oh, first class. Business class, sorry. Business class. Yeah, so still doing business class.

Still doing business class. And now she's raising her front. Welcome back to the program. Sophia. Thank you. Hi, Jason. Hello. Hi, everybody.

So how's, you decided you wanted to start investing in other people's company. Had you done some angel investing before raising this fund? Yeah, so I've invested over a million dollars in my own money into over 20 startups, including Kind Body and Public and Pipe and Liquid Death early, and realized how much I really love doing it and how much I just love working with founders. And so that's why I started business class, which is my online program for entrepreneurs, it's a course in a community.

And at a certain point, it was like, okay, I think I'm actually pretty good at this investing thing. Angel investing is different than running the fund. So I absolutely have a lot to learn on that front, but realized I'm sitting on this arsenal of assets that I didn't really realize until I was like, wait, I have great deal flow. I can have a material impact on the outcome of these early stage companies and help these founders see around corners that sadly nobody showed me around while I was building my first company. and I have access to amazing LPs and people to send, you know, deal flow my way and also to be helpful to the portfolio founders. So it's like, you know, and I'm done starting businesses. I'm a zero to one founder.

Now I get to work from zero to one over and over and over again and not be the person that has to manage the team of 20 and hopefully 40 and hopefully 100 as these companies grow. But I've seen it and I've tried it and I know I can help. I just don't want to do it again. I hear that over and over again from founders. There is a group of folks who love that zero to one. Hey, I have an idea and now it's manifested. It's in the world.

But boy, going from 100 employees and a couple of million in revenue to a billion in revenue, it's a lot of repetitive stuff. It's not for everybody. So it's good that you figure that out, yeah? Yeah. Yeah. It's a different job. It is a different job.

I find it's like repeating yourself over. over and over again and then refining the same wenty things. Messaging. Yeah. Yeah. I mean, your job in the beginning is like you're doing everything. And then you know how to do everything. You train people how to do everything.

And then you bring people in. And they're like, here's how you need to do everything. And the people who've been doing it are like, hey, we have our way to do it. And there's like new leadership that's like, no, this is how you do it. And it's just your job becomes managing timelines and inspiring people and hiring and managing their expectations and building culture, which is also really fun, but it's not the job that you sign up for,

that you think you're going to have when you start a company and think it's going to give you a bunch of freedom because that's not necessarily the case. I have a friend who refer to it as, like, you have to do your chores. So everybody loves the creation part. Everybody loves ideas and trying to turn them into a product.

And then there are the chores. And you must do your chores, hiring, firing, culture, accounting, legal, scaling, open up this office, whatever it is. It just, it never ends. And, you know, some people love it. And God bless them. There's operations people out there who can't get enough of that stage of a company.

Yeah. So you're raising the fund publicly. Yeah. Like I am. I'm raising my fourth fund publicly. I'm curious. How did you find out about the concept of raising publicly? Why did you choose that?

Yeah. I don't remember how I heard about it. I know Ryan Hoover did it, and he's a good friend of mine. So Ryan found a product hunt. He now has a fund called Weekend Fund. And they did their most recent raise as a 506C, or he called it a community raise. So I just used the same term. And it's something that allows you to raise in public.

So typically, when you're raising a fund, you can't talk about it. The SEC won't let you. you can only have 99 LPs with a 506C, or maybe that's a separate thing. There's like a parallel fund. There's a bunch of like acronyms for different things. But essentially, you can raise in public, you can talk about it. And it means that anybody, if you want, can apply. You can use it as a way to, you know, amplify the fact that you're fundraising and get

million dollar checks or five million dollar checks. But you can also use it like I did to say, hey, I want to give access to people. I didn't have a trust fund. So let's make a trust fund. And I shouldn't be here. And I don't have the pedigree that people who have my access or experience typically do. How can I bring people who could be accretive to the fund, who could be helpful to portfolio founders,

who can bring deal flow to me, who can help amplify the products and the companies who wouldn't otherwise have the opportunity. So a few weeks ago, in January, I announced in TechCrunch that I was doing, that I was raising in public, and made a website and Webflow, which I'm like learning and I really love, and I made a type form and I made an application. And I said, hey, we're allocating up to a million dollars for people to apply. Tell us why you can be helpful. Tell us about you. Where are you, you know, tag the different categories where you could contribute, tell us about your experience. and would you like to write a check between 2 and 20K? So I allowed people to apply to write checks between 2 and 20K,

which in this world is very, very, very small. That doesn't exist, yeah. For a $5 million fund. And we got in a few weeks, not a million in applications, but $6.1 million in applications for checks between 2 and 20K. So it was like over 800 accredited investors, people who are self-identifying, you know, qualified because they can only, they have to be accredited investors. And so we've taken the fund from five to ten.

I know, it's really exciting and have a list of amazing LPs like Mark Andreessen, Chris Dixon, and you, Jason, Andrew Chen, Rob Hayes, Paris Hilton, I don't know. It goes on. It's an evidence. It's a great, it's amazing. So feeling like I have wind at my back, which is a great feeling, has it always felt like that. I'm sure we'll talk about that. Yeah, I mean, in any career, there's headwinds and yeah.

Oh, yeah, you're a bit of a very public person. So that's why you should do 506C. I chose to do it in this fourth one because I was like, we have a podcast or two. And I have a Twitter following like you. And why not democratize venture capital? We get more people access to it. and yeah, I did a couple of webinars. I didn't do any press.

I should have done that. And maybe I should. And I'm taking a year to do it. I'm like, you know what, this whole idea of like high pressure going on the road, pitching people really hard.

I'm kind of over it at this point in my career. The first fund was 10. The next one was 11. The third fund was 44. And the fourth one, we had 52 million in demand already. The problem is there are some caps. On accredited investors,

you can only have 250 up to 10 million. than on qualified. You can have 2,000 people and I think it's, I don't know what the number is, but it's pretty high. So I did a very similar thing to you. I just talked about it publicly,

talked about on the podcast, and I should have done the thing where I said, how can you be helpful? But I filled up all the accredited, and that's what you'll experience, I believe, is once you have a track record, which you'll have quickly after this first one,

or I should say, you'll have it in three to five years after this one. So let's talk about, we'll assume you hit 10 million. And if people are interested in something like this, once again,

the URL in WebFlow, which is a cool product. Yeah, I know a lot of people using it. Trustfund. dot VC. You're great at design. Thank you. I think your zone of excellence is just design and branding. As somebody who is into branding and design, I'm just in awe of your ability to make great brands. So fun. I think I just make things so I have an excuse. I start businesses and do things so I have an excuse to name them. Or I just name them and I'm like, what should this be? and like will it into existence.

No, I'm a lot more deliberate than that, I'm kidding. Sometimes we get a partner here that has an offer that's so amazing. I barely need to read you the ad copy. I just read you the benefits. Linode has a startup program. It's called Rise, R-I-S-E, and it offers more than just free credits. Startups get up to $10,000 per month in year one credits, followed by a 50% and 25% discount in each of the next two years.

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And you can apply for their startup program, Rise. Rise members receive up to $120,000 in free infrastructure credits during their first year and up to 50% off in the years after that. Take us through the creative process of business class and trust fund because they're both funds. And then before that, Nasty gal and Girl Boss. These four brands are just all spectacular. So take us through your creative process in branding or coming up with a name. What do you do? Smoke a joint and get a whiteboard app or have a glass of champagne and what do you do? We'd make me kind of weird. I don't know. I can't do. I can't fall in conversations.

Makes me a little dumb. It makes me slow. I think that's kind of what it's known for. Yeah. I don't have time. The learning curve is high. So Nasty gal, I was like, okay, what do I name? I almost named it. I heart vintage, which was like, oh, God. It would have just been so. Yeah, I know. It's not even. And my, I was like, oh, it's memorable. I think I can get the name or something like that. Yeah. But then I was like, okay, there's all these girls selling hippie stuff on eBay. And I want to do something different. And my spirit is not hippie-dippy.

My spirit is like, I don't know. The word edgy also feels kind of dated. But there was this, I worked in record stores and was really into music. And music was the thing that like I wasn't, I played bass in high school. But I just loved like collecting records and downloading stuff and these weird private servers that record nerds had and would like rip stuff off of vinyl that wasn't, you know, re-released on CD yet. It was just like, it's what I love. And this, and I remember when this album was re-released, it's called Nastygal by a woman named Betty Davis. And Betty Davis was

married to Miles Davis for a little while. And she was allegedly like too wild for him. And her music is saying something. Yeah. Her music is so good. And she was so stylish. And I just absolutely loved it. Um, so I was like, I'll name it nasty. And I didn't think it was a word I'd be saying for the rest of my life, right? It was an eBay store. I wasn't like, yes, I'm going to go out. You know, I'm going to somehow get on this week in startups. I'm going to, I didn't know what tech crunch was.

I don't know what investors were. It was just, it was like an eBay store. And it cut through the noise, you know, the first website. So it was nastygal vintage.com. When I had to buy nasty gal.com, you can imagine what kind of website I had to buy it from, which was like entertaining. It might have been an adult in nature. Yeah.

Never owned Nastygalleryd. I haven't been there in a while, but there were definitely, like, girls who were like 20 years old being like, grandma, look at this dress and typing the URL and wrong. There was like upset parents looking at their credit card statements being like, what is this? Which is like, if you have your parents credit card, I don't feel bad for you. I'm sorry. It's hilarious. And then Girl Boss? Where did that?

Girl Boss, another dink reference. So, Girl Boss, I took from the name of a film. called Girl Boss Gorilla, G-U-E-R-I-L-A from the 70s, which is a very little known female Japanese revenge film of a genre called Pinky Violence, which Tarantino has taken a lot of inspiration from, admittedly. And they're just, again, super stylish, really fun. It's like these super cool Japanese girls like knife fighting in the street. Yeah.

It's so good, right? So I was like, Girl boss. Girl boss, yeah, girl boss. Yeah, girl boss. Yeah. So that's where I was just like, cool, I'm going to call it girl boss. So that's interesting.

The genre films that Tarantino is obsessed with, I just read, or I listened to, I should say, his audiobooks. Cinema speculation. Did you get it yet? No, but I heard it's so good. It's great. And then I started watching some of the films that I'm like, these films are, uh, what they would call a genre film, right? Like horror, revenge.

Yeah. Female revenge. Yeah. And, um, they're not exactly for me. I like thrillers. I like mysteries. I like a little more going on there, sci-fi. Uh, but I get why he likes it because they're, they have a certain, as the word

says, genre films. They have a certain purpose, which is to excite you and delight you and, make you uncomfortable in the theater. And I highly recommend this book. But yeah, that's interesting. Yeah. Mining old media from the 70s to find interesting where it's a spectacular. And then business class, I was like, oh, my God.

Naming of entrepreneurship course so difficult. So it's like, ooh, do I call it Founder Academy? Do I, there's just the common, all the combinations of words are like, academy, university, you know, the circle, the club. They would be, and they're so generic. Descriptive is good because you don't want, for something like that, you do want it to sound relatively straightforward. Like, you want the title to kind of tell you what it is instead of be like, you know, illumination. I'm just looking at this like coffee cup of intelligentsia illuminating coffee.

But like, you know, that's no one's going to know. It's good coffee. I will say. It's great coffee. Mine's super cold, but I'm just sitting here camping out of my desk. John Zia has a great logo as well. It does. We named Darry's founder university and it's problematic because.

because people keep calling their own things Founder University. And I'm like, hey, that's our trademark. Yeah, try your boss. Can't trademark that. But I was on a walk and was with my ex. And I was just like, okay, I was just straining together words. I'll just do that. I'll just shoot, shoot the.

And I was like, business class. And my God, that sounds so basic. And then I was like, business class. And I was like, ooh. And then I was just, you know, started putting Pinterest boards together of like old Pan Am kind of ads and just like all the, you know, uniforms and fun puns and references. So in business class, you know, there's modules and there's lessons in a course and the modules are called flights. There are seven flights over the course of a cohort that lasts 10 weeks people get lifetime access to the whole program. But it's really, it's self-led, but we also drop one flight a week.

so that people are kind of taking, consuming that content together and not overwhelmed. Within those flights, the lessons are called legs. And over those 10 weeks, because there's only seven flights, there's three layovers, which are catch-up weeks. It's just like endless, it's just like endless puns. Endless things to build. Well, I mean, that's the great thing. When you strike a theme, and I remember seeing it, and I was like, oh, she's doing a business class.

And then you always do photo shoots of yourself and, you know, great, logos and everything. And I saw you doing it on Instagram or something. And I was like, ah, yeah, pull it up. It's businessclass.com to my producer. I don't know where trust fund came from. But in business class, I go through naming and branding and visuals and, you know, finance and legal, everything. But I do take people through, well, obviously like the thesaurus. So anything you think it is, like,

what's just one degree away? What's the kind of like asymmetric reference that isn't the thing that you're necessarily talking about. You don't have to be super on the nose about it. And then just because I love rhymes and puns, I go to rhymedictionary.com. Oh, so great. And I'll just like jam out on like, okay, here's one thesaurus word. And then how can I turn that thesaurus word into like something that rhymes with that?

And it can be a, what's that called when you put two words together? There's alliteration. it's a portmanteau I don't know it sounds fancy it's when you combine two words to make a new word

Port Mando yes I've heard this something like that I didn't know that when I was doing it someone told me that recently so but it sounds fancy alliterations when you have

two of the same letter to be in sound yeah letter or sound yeah Kim Kardashian Oh yes there are better ones there are there are better ones

but that's that's a fine one as well yeah Yeah, Portamento is when you blend words together, right? Yeah, to make like a new one. So what would an example of that be like a norm core? I don't know. Oh, yeah, no, there's, there are some of those words now that I listen to a podcast called Red Scare.

And they are into this kind of normie culture or whatever. And they use all these hip words and stuff like that. Okay, imagine this. You got an idea for a great tech startup and you think it's going to change the world, but you got a problem. You just don't have the engineers that you need to make it come true. Why? Well, it's obvious. It's hard to find engineers. There's a lot of competition. And, hey, you're trying to keep your burn rate low. You need to conserve cash. Now, imagine you had a partner who could provide you with more than 1,000 on-demand developers, right? As many as you need. And these developers were all vetted, experience, result-oriented, and they were incredibly passionate about helping you grow your startup.

And what if they charged competitive rates, things that you could afford? Does this sound too good to be true? Well, let me introduce you to lemon.io, startup shoes, lemon.io, because they only offer handpicked developers with three or more years of experience and who have strong portfolios. In fact, only 1% of candidates who apply to work with Lemon.io get in. A couple of our launch founders have worked with Lemon.io and they had an amazing experience. And listen, I have used outsourced full-time teams for decades, whether it was way back at Weblogs Inc, Mahalo, ontoinside.com at launch, this is the way to do it. Go to lemon.com slash twist and find your perfect developer or tech team.

And you can do that in 48 hours or less. And Twist listeners get 15% off for the first four weeks. Stop burning money, hire developer smarter. Visit lemon.io slash twist. So what stage are you going after with the fund? Yeah. And then what stage? And are you vertical specific?

Because I think people would say, oh, Sophia Marosa, girl boss, nasty gal, this, that the other thing, she's going to do content and she's going to do fashion. And is that true or not? completely untrue, none of the above. I tried to build a billion dollar direct-to-consumer fashion business. It's really hard. I've watched my friends try to build billion-dollar direct-to-consumer businesses, and while some of them may be valued at a billion dollars,

it's doubtful whether or not any exit will ever happen remotely near that price. And doing a billion dollars in revenue is like a whole other question. So I put enough stuff in landfills. I don't want to do stuff. Liquid death was a great investment, but in general, stuff is not interesting to me. Consumer and kind of the consumerization of enterprise

or B2B is really interesting to me. So that's one area I like to invest in. It's seed and seed and pre-seed and maybe seed plus, whatever. I'm not investing in anybody's bridge rounds from having raised their seed a year ago. These are like new companies that are just starting now because it's going to be a great vintage, because valuations are very much in line with,

I think, where they should be. And the word profitability is finally in the mix. And I bootstrap my first business with no investors or debt to $12 million in revenue. So I get what that means. But I'm also investing in companies that I think can become billion-dollar businesses and are tech-enabled. So they don't have to be purely technology companies. It could be, as far as products go,

probably the only thing I would invest in that's a physical product. might be something like a wearable. So my investments will be across like B2B and the consumerization of enterprise. So workplace products, largely stuff that entrepreneurs can use because I was the C when I started on eBay. eBay was a B2B business. It was a marketplace. Nobody knew was using that term.

It was the average person starting a business. eBay gave me this framework that said, here, fill in these blanks and you have a business. And that was a very new thing. Would I become an entrepreneur or opened my own vintage store on what hates trade? No, like, no one would have given me the money. But I was able to cobble together my skills and, you know, my computer and a little digital camera and buy some vintage from vintage stores. And there it was.

I had a business. So today, the people using the Shopify's of the world or the calendlies of the world, the calendar user could be someone who is an eyebrow, like a brow artist who does. people's brows, but she's also a business person. But she doesn't know what SaaS is. Caldly's SaaS, Shopify's SaaS. Like every person that read Girl Boss, the 500,000 people who bought it in this entire generation,

if they're not entrepreneurs, they're entrepreneurial, and they're probably using BDB tools, even if it's a sorority using Slack for something, right? So people are hacking these, what would at one point have been considered enterprise tools for their personal use. They're using communities that were meant for individuals

for professional use. And what was the B2B, I think, is the C to B, I guess, in that these are brands that people are, that are getting into, these products that are supporting

entrepreneurs or the business of one are ones that are attractive because they're also great brands and there's something you want to align yourself with and they're great tools. Like, Webflow is cool. Like, I'm like, I want to say I use Webflow. I want to say I use Notion and someone who's not necessarily running a business can use

notion, but for the most part, it's marketed as like a B2B tool. And this is a great observation. Yeah. If you think about it, you just said, raising your fund, you talked about Nastygal and how you did that with the tools. And you look at raising your fund. You're using, I believe, Angelus platform, which has made it like, that abstracts 90% of fundraising,

type form, web flow, the press, and your social media following, right? And then when you did, you know, business class,

I'm sure you used some collection of technologies and printing and all kinds of stuff. Yeah, I don't want to reinvent the wheel. Never, ever again. Yeah. Have you thought about your,

how many portfolio construction? Let's talk about portfolio construction and then follow on funding. This is a lot of lessons I learned with the $10 million fund. I think $10 million is the perfect solo GP number. It's constrained. And have you thought about how many names you're going to put in there and the average

check size? We know you're going for the scene stage, great, maybe Series A sometimes. And you're going for tech enabling tools. You're not going for fashion or whatever people might pigeonhole you into because of your previous success. Got it. Check, check. What is the check size going to be?

How many names and then follow on funding? Because that must have come up a bunch when you were doing the fundraising. Totally. Yeah, people ask all these questions. And I guess I just want to clarify, because I mentioned wearables and that has nothing to do with entrepreneurship. Healthcare and fintech, money faster, more accessible, more convenient, more beautifully designed in a new way. Doesn't have to reinvent the wheel. But fintech and health, digital health are also two areas that I find myself really attracted to. So businesses that make people's lives better just through technology. Entrepreneurs and individuals. So it's a 10. million dollar fund. We'll write 150k checks into probably 60 or 70 companies and I'm not planning on having any reserves. I may do follow-ons through SPVs, never done an SPV before, but I expect to

offer those SPVs to my LP base. And yeah, so that's something that they'll have the opportunity to invest in along with me if those companies, when those companies go raise subsequent rounds. It's a nice way to do it. That's how I did it in the early days was just, hey, there's a round coming up. Does anybody want to participate? LPs go first. It works. It becomes a lot of paperwork and a lot to manage.

So the funds might be a more efficient way to do it in terms of operations. You really need to have a lot of operational people when you start getting into SBBs is what I've learned after 260 of them. Sounds like a nightmare. Do you use Angel's? We started on Angels. I was the first one famously. And the first one we ever did was com.com. So I think that's the most successful one ever done to date.

I put in 50K, I think, from our fund and 328,000 from the syndicate. Again, it was a $10 million fund. We were making 50K bets. And a meditation app seemed like a crazy stupid bet at the time. People criticized me pretty hard. And it's a $2 billion company. So that worked out. We own 5% of it.

I think it's the most successful syndicate ever done. Certainly on Angel's. I don't know if there's other ones, but in terms of a multi-dollar company. The pull. It's probably the most successful ever done. And then we did a shore, but a shore fund management went out of business. And so I just hired the top three people from a shore in the tax department, and I created SPV solutions, my own SPV company. Cool.

Because none of the ones out there, I think, are going to be long for the universe. With exception of Angel List and Card, I think, those are super expensive. Card is $40,000, I think, to maintain an SPV for 10 years. Oh, wow. Better be a big SPV. Yeah. Super expensive, yeah. So then no follow-on reserves got it. 60 names.

Talk to me about how you're going to process all this deal flow because you're kind of legendary. You're going to get a lot of inbound. Yeah. How are you dealing with that? And from what I know of you, are you an introvert or an extrovert? I'm very much an introvert, but I'm also really curious. So I love meeting people.

I mean, I've been on like a full listening tour for the last year before I've been decided to raise a fun because I know what comes on the other side of doing something successfully and okay, this is going to be a 10. Now it's real. I've heard from enough solo GPs and, you know, people like, okay, fundraising is a slog. It's not as fun. It's just having conviction and writing a check and do a founder you like. You know, it's very different. I have a lot of deal through it flow just through the website, which is interesting. So, yeah, trust fund. v.C. And then stuff from other folks, like founders that I've invested in in the

past, people I've met over the years, some of my LPs, other GPs and in big funds, you know, you've sent me deals. Sometimes I get invited to SPVs and I'm like, hi, can you make a direct intro? I've also just gone cold to people and, you know, for Kind Body when I invested, I went just to their DMs and I was like, hi, can I talk to the founder? So people will just get on the phone with me. It's if I need to, if I want to source something, it's not hard. That's such a huge advantage that I have. It is a huge advantage. You're underestimated.

Deal flow, I believe, proprietary deal flow is the name of the game. And so what's great is having sold 500,000 books and you know, you're following, you're just going to get deal flow. Other people aren't. And then the second thing is, in deals that are of high quality, the founder wanting you on the cap table is a major thing. So you get both of those things going for you.

I'm never not going to be allocation. But again, 20 checks. This will be very different. And my checks are small. And the check size, and I'm sure, I mean, maybe you thought about this when your fund's much larger now. And so I'm curious what size checks you're writing. But what was easy for me was getting as an angel, okay, 25, 50, 100, 150K allocations where I had to go raise a first time fund and be, you know, have all the glory, it'd be like, I'm going to raise a $50 million fund. It's my next move. I'm the girl boss. Like, that's not what I'm going for. Like, I want to do a really good job. And there's enough of a learning curve with managing a fund and managing the deal flow.

But also, when you have a much larger fund, you're fighting for allocation. So if I was trying to lead seed rounds and put in million, two million dollar checks, all my friends that are sending me these great deals, they may be people who are trying to write million and two million dollar checks. Yeah, now your elbows, you're bumping into each other. Yeah. So that part was just like a really easy layup for me to be like, okay, this is already happening and working at this size. let me just keep doing that and, you know,

formalize it beyond angel investing. And in terms of managing the deal flow, I actually hired someone. I've like, my fees, you know, it's a small fund, but I found someone amazing.

Or you're charging the two and 20 kind of situation? I'm charging two and 20, yeah. So for people who don't know, 20% carry, 2% fees a year, basically 10% fees, or 20% over the life of the fund or something,

probably tails off. There might be an upper cap, but that's only 200K a year. Yeah, and that's like travel, entertaining, taking a founder to dinner. You may are made on it invest in. It's like everything.

It's nothing. This is the challenge. You have to have a, when I did the first fund, the first two funds, I think I had no fees. Third fund I finally put fees on. And I paid for all my team

out of the podcast revenue I have. And just starting to change that a little bit as I go into the last two funds. So I just found someone who's been living in Pitchbook and at someone else and worked for a friend of mine. Do you know James Vincent? He founded Media Arts Lab and then and now does this strategy firm called Founder. They also have a venture fund. So like a researcher or an analyst associate.

Yeah, she's been working for him for the last six years. Okay. Great. Yeah. So she was on her way out anyway and, you know, came to me a known entity. And so people I don't know, I don't know. I don't know. And also with deal flow, like, I'm looking for really high quality stuff as much, you know,

as much as like cute that I was a community college dropout. And yes, I'm giving access to people who maybe don't have like the pedigree of the typical person who would, you know, invest in a fund or be invested in as a founder. Like I've already over-indexed on the like community college dropout side. Like I'm for the first time my career, I'm going to be a little bit of a follower because, again, I have a lot to learn and I don't need to be finding like the diamonds in the rough. I'm going to be investing alongside top tier firms who can see the landscape because if I'm looking at a fintech product, I'm going to see some of them. Yes, I have great deal.

I'm not going to see all of them. They're going to see all of them. And I can be like, this is so cool. Check this out. And if I send it to any of these guys, chances are they're going to be like, yeah, we saw 10 things like that. This is why we passed and then like, oh, cool, I have an opportunity to learn rather than be like, I'm excited. about this thing, you know, they've got a partnership that sees the full landscape. They're also doing diligence on the founders and on the, on the companies, and they're possibly taking board seats. And that's just like a much safer bet for me. And with money, I want to make safe bets. And with the $10 million funds investing in that many names,

if you do wind up doing 40, 50, 60 names, given the staff size, you're also not going to have the ability to do deep due diligence. You're not going to have the ability to do. You're not going to have the ability to do governance. You don't have, you know, three managing directors to put on, or two managing directors to put on boards to represent you. So, you know, it's, it's, I think the approach you're taking is perfect. Um, learn. Deploy five, 10, million, 15, whatever you get to. And, um, learn. The only thing I would edit in it would be to save one million for reserves. Um, and, you know, maybe do five less investments. Because I do think when you hit 30 or 40, you have enough diversification that you'll hit a winner.

And the thing I'm trying to learn, because I have 350 investments over 12 years, is how do you find out which ones are the winners and then get more money into them before other people figure out their winners and take all that opportunity? Because, man, the ability to invest in the series A, B, and C of Uber or Robin Hood or any of these, which I didn't, because that was won and done. that was the big challenge for me. And now we've kind of fixed that. And I think that's what most fun managers do.

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100%. We'll not do anything without them. Wow. I would advise you to not do that either. And they'll say, oh, well, I'll just be a handshake agreement, previously known as the gentleman's agreement, the handshake agreement. you don't want to do, you want them to do a side letter and say, listen, I'm Sophia Amorosa,

I can help you with tweets, I can help you with introductions, I need pro rata, my LPs, I told them I get it, and then almost universally they'll do it for you. Ooh, I told my LPs,

I love that, I can blame my boss. Oh, that's so cool. In my case, it happens to be the truth. Yeah, and here's the next card that'll happen. The founder will give you pro rata,

a series A will occur, the term ship comes in, they're like, oh, this big, venture capital firm says they'll put in $5 million at $20 million post. But everybody has to waive their pro rata. And then so what I do, after this happened to me over and over again, maybe four or five times I called those VC firms.

I said, hey, listen, do you really want to run me over? Because I need to get this prorata and they would say, no, no, no, no, of course not, Jake. We love you. Yeah. You're like, because I have weight to throw around. Well, and you do too. And the greatest weight is, I will not pay.

pass you the ball. And I literally said that to somebody. I said, listen, I'm Chris Paul. I'll bring the ball up to the court. I'll pass it to you where you like it. If you try to screw me and take my pro rod away, I will ice you out. I will never pass you the ball, which is what you would do in Brooklyn if somebody wasn't, sure, you just don't pass on the ball. You pass it to the other people let them score the ball. People get the point real quick. So you can use that. And then the thing I started doing is I started preparing founders for this. Later stage VCs will try to screw your angels and seed investors, be prepared for it and understand that

I have your back for all time. And if they screw me, there's only one person after me because I'm one of the first investors, is you. So if somebody is willing to screw your angels and seed investors, guess what? They're going to screw the founders next. Or the team.

It's just the nature of some sharp elbow people in this business. Yeah. You have to stand up for yourself And then you have to have information rights as the other thing. Yeah, I was going to ask you about that. I just put in our documents. I say write a monthly update in the first couple of years of the business.

And then, you know, when you get your series A, series B, maybe it goes to six times a year or quarterly. But we actually put it in there. We track it. We follow up with them. And if somebody, this is my best advice, month one, I'll have somebody on my team say, hey, we didn't get January something. Month two. Hey, we didn't get February's. And then in March, hey, we didn't get January, February's.

we checked our spam folders. Did it get sent or do we miss it? And how about we do a Q1 with you? Well, I said, how about we do a Q1 and I have them and then they CC me? Or they CC, you know, my wags, aka Mike. You know, they say, hey, Mike would love to jump on a call with you or Jason would love to jump on a call with you. And then we'd have a phone call. Yeah.

How did the first quarter go? And then I'll just take them right up front. I know how this is as a founder. If you're not sending an update, it's either because you're so busy, things are going so well, or there's a lot of problems and you want to fix them before you send the update. Am I right?

And they're like, yeah, you're right. Which is it? They're like, the latter. I'm like, okay, what are the problems? How can we help you fix them? Yeah. And that's the early warning system.

You know what? Nobody does it in our industry anymore, especially not the C investors. They put a bet in and they disappear. There's not. And I think that's the problem in the industry right now is all these new GPs. A lot of them have never run a business

like you and I have. Therefore, you know, they've never hit you. 10, 20, you must have hit 50 million of revenue much more than I did. Over 100. Over 100, yeah. And so, like, you've run a business with a hundred million of revenue. Like, you know what you're talking

about? Like, that's why they want your money. Yeah, that's the thing. It's like, let me be helpful before the it's the fan. That's why I'm here. Don't email me telling me your company's falling apart because like that's happened with two of my portfolio companies. So frustrating. In the, you know, last few months and it's, it's a

bloodbath. People are overvalued. they can't raise their bridge rounds and their, you know, even down rounds, whatever, it's hard. But, you know,

don't tell me when it's too, you know, and then I'm like, okay, well, here's, here's, here's someone who might be able to buy it,

but like, I'll get wiped out anyway, but I still want to help. Even if I'm going to get wiped out, I want to help. Like, I can help. It's harvesting all of the shit that I've done for the last 16,

17 years for free. It's not like for free, but the founders aren't paying me, right? Like, I'm giving them money. I'm giving them money. to harvest my expertise to like it's it's I love it's what I love doing because I don't want to

keep learn and of course I'm going to continue learning all the time but there's so much that I can add that I would much rather give to someone else to apply to a startup than for me to do after again after you know building companies for so long use it like use me like text me text me at 11 p.m. just use me ask for things I did something early on where I told founders, you know, again, language matters and then saying something two or three times, like you really care about words like I do. And I came up with just a little phrase like, and I just said, at some point, everything is going to be a complete utter disaster. It always is, especially for the successful companies. When that happens, you can't tell your employees

because they're going to get scared and they're going to quit without your fear. Can't tell you're board because then you get scared and they're going to fire you or try to replace you. I said, just call me and just tell me exactly how f-up it is. And I will tell you 10 stories. I guarantee you that are more effed up than what you told me. And then I can just give you candid advice of how I would approach it. And, uh, you know, at one point I had somebody call me and he's like, I can't take it anymore. It's a Saturday afternoon. He said, you just to call you. I said, where are you right now? I said, I'm in my bathroom. I just threw up in the shower.

I'm so anxious. I said, okay, you want to get coffee or something? It's like, I got the kids and my wife waiting in the car. I got to go take everybody to brunch. I said, okay, have the best brunch ever. That's the most important thing. And then meet me for coffee after. Just tell your wife, your investor needs to see you.

You got no choice. Okay, great. We talked. It wasn't that bad. Yeah. And I always tell them the same thing. Like, listen, if this company doesn't work out, you shut it down. We all take a loss.

There's more companies. And then start a new one. based on what you learned here. That's the great part of this. The thing people don't realize is that they're not, of course, you're going to stick it out as long as you can, but not every idea is going to work out. And sometimes you make mistakes as an operator, you hire the wrong people or you're overvalued or there's macro things happening outside of your control. And hopefully we're all going to have multiple lifetimes and we can all be cats that land on our feet after, you know, with nine lives, right? Yeah. But a lot of people think that because they attach their identity to something, that if that's no longer part of their, you know, who they are, then they're not worth anything or they're a failure. And it's just like, that just comes with the territory. And I haven't learned anything from, I mean, I've learned from success, but I've learned the most from the challenging times. It's like when the tide is high, you're like, oh, cool. Like, there's no like weird crabs shells and, you know, cans and bottles.

stuck in the mud and then the the tide recedes and then you're like oh all this crap was happening under the surface in my organization I had no idea and then you get to see all the crap that was like hiding out under you know all the you know celebrations and champagne cliques and you know milestones and accolades that was like it was still there even when your company you know even when business atrophies or plateaus like that stuff's there all the time and it's a gift to see it because then

when you do company number two you know what the with the murk looks like also you start with the time low you mentioned like you become identified with this you were the nasty gal you were the girl boss to an extent that like

people wanted this to be your identity and they made a TV show about you like talk about how you put those things to bed and just or how you manage it now because listen I had the same thing I was the silicon alley reporter for my first magazine I was Mahalo I was engaged I was this week at startups now I'm all in I was angel investor in Uber yada yada yada I mean the public wants to pin you and put you in a box forever you want to move on and do the next thing so how do you how does sophia amorosa handle that let me just paint a picture from June of 2016 to April of 2017 so June of 2016 I'm on the cover of Forbes

magazine named one of America's richest self-made women with a net worth of $280 million, allegedly richer than Beyonce. On paper, like, you know, my company was worth $350 million. I'd bootstrapped it, so even after raising 60, I owned 80% of it. So I owned 80% of, yeah. The first money in Danastigal is out of the growth fund. July of 2016, my husband of like less than a year. year like bails and it's like we've been together for like four or five years like what's going on

what were you like emotionally could you just give me warnings or something that was really that was that sucked and then November of 2016 while I'm standing in front of a thousand people at a conference in Australia promoting a book that I was like you have to go on the book tour right like the wheels are you know and I had hired a CEO for nasty gal two years prior. So I had a CEO running the business because I didn't like being the CEO because I know my strengths and one of my strengths may not be hiring CEOs, turns out. And it was on the day that Trump became, Trump was elected in November of 2016 that I'm on stage in Sydney moments after having had a board call saying, all right, like we have to send this thing into

chapter 11 because it was like Hail Mary after Hail Mary after, you know, down rounds being cock blocked by, you know, you could guess who, whatever. Yep. And then April. And then it's just like the girl boss is, you know, she's not the girl boss. You know, she had to make tough decisions. How dare she, you know, ask people to work hard and toxic culture. And it's like, guess what?

I'm like 20 something. And I've never even worked in an office. like the only office I've ever worked in my name was my name has been on the lease of doesn't say that I'm not responsible for having you know for anything right yeah um and so that was just all the conflation of who I was as a CEO the person who wrote this book you know this girl millennial's 20 something year old with like an edgy haircut you know standing a kimbo looking like she knew what was up inspired so many people and then oh wow watching this like this slow face plant. And then in April of 2017, the Netflix series came out. So four months after Nastygal fell apart. I laughed. I stepped off the board.

And I was like, cool, I'm 10 years. You know, it was like, it sucked. But it was also at that point, I just was like, I don't know what to do with this thing. It was my entire youth. I was like kind of ready to move on. It's hard to quit and it's hard to be fired when you're a founder. and you've raised money, and it was torture for the last few years.

And now there's this scripted comedy. I mean, it was amazing. It was a Netflix series was produced by Charlize Stheron. It was like amazing talent. Called Girl Boss with a girl who's 22 in San Francisco, starting an eBay store, called Nastygal, being streamed into 130 million homes in 195 countries in almost every language. a few months after I have like divorced myself from the thing and the person I was for the first, for the last decade.

So now there's this, all this new awareness of this nasty gal and the girl boss and Sophia, her name was Sophia in the show. And it was like, well, who is she really? The character's kind of abrasive. Well, is Sophia really like that? It was just like the show was the thing that really kind of like, you know, and there's people whose jobs are literally critics for television. Like, I've been critiqued. Like, I've been put through the ringer, but, you know, there were headlines like, um, the worst thing about Netflix's Girl Boss is its source material.

Ooh. That's, that's, that's, that's, yeah. So how did I deal with that? I just kept moving. I'm like, I'm not, I don't know. I'm not going to disappear. Girl Boss still has momentum. Like, it inspired so many people and it did so much.

And I can't tell you how many thousands of DMs I've gotten over the years from people who were like, I quit my job because of Girl Boss. They finally started my business. Like, it's amazing. I wouldn't, I didn't know that someone like you or me could start a business because Girl Boss came out a year after Lean In. And that was the big new modern book that was written by a woman in business. And it was like Cheryl Sandberg and Susie Orman.

It was just like, holy shit. And I threw a wrench in it as a community college dropout. And every other probably even college educated girl, but just maybe not Ivy League or like MBA girl was like, Oh my God. Like I could start a eBay store. I could start a Nazi store. I can start a Shopify business. I can,

if she's confident and she didn't come from a lot, then maybe I should be too. You de-mistified it. I just kept running with Girl Boss, and it was a great ride. Yeah, I mean, the, what I think of when you tell the story, and thank you for sharing it, by the way.

I think it's good to be honest like that because other founders, especially the ones you're going to invest in, can see. Like, they build you up. They build you up. They build you up. Yeah. The press, the public, the social media, everything. And then, yeah, they love, they love the face plant. They love when you trip and fall. But I think about our discussion about creating great brands, right? And great names. You create this a great name, girl boss. And then it's like, oh, well, that just writes the headlines for the critics. But these critics mean nothing. They literally mean nothing in the

arc of history, there have been like three or four critics who actually matter. Roger Ebert was an exceptional thoughtful critic who was a super fan. Quentin Tarantino's book of criticism is actually very thoughtful, but almost universally, critics don't matter. And their life's work is often to take other people down. You know, once in a while they support something, but most often they get a real kick out of kicking people or laughing when they trip and fall and they they risk very little and this uh is plagiarized from the Anton Ego speech at the end of Ratatoui. Have you ever seen Ratatoui the Pixar film? Yeah, it's been a while, but yeah.

Watch the, just type in Anton Ego. He's the, he's the food critic and he does an incredible speech at the end just about the creators versus the critics. Yeah, it's just like consider the source. It's someone evaluating you who's never. done what you're doing, that has no idea what that's like. And it's like they've never been in the ring. How could they understand what's that like enough to even criticize you, right?

Like, you have to be an expert. Well, then gender plays a huge role in it too, because you were pioneering in the tech industry and the name of the book is Girl Boss, Nassie. So then Gender comes into it and they're like, oh, look at this little lady who wrote a book. It was like, yeah, totally. it was like Natalie Masseney from Netter I mean it was like Tony Schaeferms

I started an e-commerce business in 2007 pre-glossier, pre-away, pre-outdoor voices, pre-Bumble, amazing women I've had been really lucky to watch have their own awesome rides build great companies

so it was really weird and lonely and I was kind of heralded as this poster child because there was no one else to point at. Also, I probably sold magazines. Like, I, like, knew very well. Like, just the, the whole kind of, the whole kind of thing. The machine. Let's face it. Yeah. And the headlines when NastyL fell apart was, does the failure of Nastyau mean that millennials aren't ready to lead? And it's like, I'm sorry, like an entire generation. How am I responsible for an entire generation? That's wild. That's me. I mean, it's like, if I,

to be, and especially with the word girl boss and, you know, maybe we'll talk about that, you can only hope that the brands you create or the mark that you make is such a part of the zeitgeist that's representative of whether it's good or bad or becomes warped by culture or ages poorly or, you know, becomes the coolest thing ever and stays the coolest thing ever forever, which nothing really does. Like, leaving that kind of a mark and putting something out there that is so ubiquitous, it's like it's a wind no matter what. Like, it's such a fascinating thing to do. glad to hear you say that, Sophia, because the way I look at it is lean in and girl boss, both of these. And I have three daughters, so I care very deeply about this.

It came at a time where people were like, women, tech industry, and both of them, I think, gave permission in different ways. You know, one is more like, I think, you know, what Cheryl was doing was saying, hey, listen, if you're in that board meeting, if you're in that meeting and you're one of the few women, not, forget about being a founder. Forget about being the boss. Just you're a woman in the tech business. you know, stand up for yourself, stand up for your thoughts, you know, own it, lean in and take responsibility for pushing things, right, is my interpretation of it. And she was sort of saying, like, she didn't lean in enough and she wish she had. So she was trying to pass that on. And then for you, quote unquote, nobody like me, you know, not from the Ivy League,

it's those people, and this informs a lot of my investing, it's those people who are, you know, outsiders who actually make the biggest impact. If you just look at the history of this, we remember Zuck and Bill Gates, you know, dropping out of Harvard because it's so notable and it seems like such a great poetic story. But what you'll find as an angel investor for anybody listening who chooses to do this is it's people who have skills who want to change the world, who are irritable and unsatisfied and, you know, maybe not the most balanced, but who also are obsessed with customers and products to a point that. They want to change the world. And I think that book, and just even the term, it gave permission to a lot of people like you were saying. And you get those DMs. And so the critics and all the nonsense does not matter.

What matters is the legacy. The legacy is amazing. And the legacy, it's just starting. I mean, you're still very young. And this, the big thing that I see in our industry is a lack of people with check writing ability, who are not white guys from Harvard. and Stanford's business schools. And that's the revolution right now.

I was talking to Molly, and this weekend store was about it just the other day, of how now it's 16% of decision makers once that in venture are women. Still, you know, whatever, a third of what it should be. He's got a triple, but it'll get there.

And I think the way to do it is to start your own fun. It's to give me money. Well, bottom line, if you want to see the change in the world, I actually think this is important for rich people. And I've had this conversation especially not just with women,

but women of color. There are a lot of people who should, they virtue signal all the fucking day long on Twitter. They put up Black Lives Matter, you know, BLM or, you know,

some show of support and they're supporting the next thing and the next thing. They don't write the check. You've got to write the check if you actually want to see the change to have it. It's not enough to just tweet

or retweet or like. Take out your checkbook. I'm stoked for you, Sophia. I think you're going to be amazing. this. Thank you. And anybody who's a founder, go to trust fund.V.V.C. slash invest. But speaking of accredited investors, there is a limit. And I have a lot. So QPs call me. I am in the QP phase as well. Qualified purchasers call me. That means you have a lot of money. So the people listening who have like over $5 million in assets. Family offices. I, high

high net worth people. Email. You can write 100K, 250K check. Yeah. This is what you need to do next. In info at trust fund. VC.

Trust fund. Dot fund. VC. Go there if you're a founder. Go there if you're a QP. If you're accredited, sign up just so you have them for next time. I did a,

yeah. Where you're going to be on your second and third fund is where I am now on my fourth fund, which is the lottery. So accredited investors. Cool. I did three or four webinars. I collected all the interest. I had so much.

I said, okay, existing accredited investor, go first, then everybody else is in a lottery. So you have to this date, put your allocation, and then I did the lottery. People dropped off. They didn't fill the paperwork, no problem.

Everybody else. And then I took the people who are a credit investor, they said, in the launch fund five, since you did four, I will allow you to go first in launch fund five, or if we do another lottery, you'll have three ping pong balls to new people's one, let's say. So you have

three X the chance of getting in. And I think the future of this is not the big, endowments for folks like us, I think this public thing, my thinking is, well, maybe instead of going for $150 million, just do $25 or $50 million every 18 months and just allow access to people who don't normally have access to this venture class. Yeah. I think that's a revolution. And I know we're probably out of time, and I'm just going to ask your advice on this.

How long do you plan on deploying this next fund for? I think just the fund cycle is such an interesting thing. Yeah, so I, it's such a great question. I sat out a lot of 2021 and 2021 because of the valuations. It didn't make sense. People want a 50 million before they had product market fit or customers or had even launched their product. And I was like, well, that makes no sense.

There's no chance for, I like a 50X. Anytime I make an investment, I want in my mind to be able to map out a 50X. We're investing at 10 million. Okay, 50X is 500 million. We might get diluted a little bit. how do I get what kind of revenue with this company to have? And then I do what's called a total addressable market, but I do it a bottoms up. So I just, with my team, have that very thoughtful conversation about entry price. And to your question about deployment, it is based

on market conditions. My belief is in 2023, I'm seeing so many good companies that have, you know, five to 50K a month in revenue, which is my sweet spot. And they're priced at five to $15 million. And then I see these other companies come out of certain accelerators. I'm not going to dig anybody for getting a great price. But they've built up such a frenzy, maybe some accelerators, that, you know, raising at 20, 30, 40 million before you have a product in market, not for me. Those companies inevitably come back to market at the same valuation with five customers. So I'm patient.

I think the right deployment schedule, according to everybody I talked to, is 30 months. 24 to 30 months for primary investment, you save a little bit for reserves. That's what I hear. But I think you could do it in 18 to 30 months as well if you have great opportunities. The most important thing is portfolio construction. Picking winners.

You have 40 names. So you have a chance of an outlier. I hit outliers every 25 to 50 and as best as I can tell. So I think this is the vintage where it's going to be extraordinary. If you can invest at $5 million, That's when I invested in Uber Com. Robin Hood was under 20, I think. When you invest in those kind of early evaluations as a seed investor and you maybe can put

in a second bet on the winners, this is why I think the one flaw in your game is the follow-on. And so I'm going to keep pushing you on, just save 10% for follow-on. Because what if you hit an Uber? What if you hit a Robin Hood? What if you hit a Com? You really want to put that 500K check in or 250K check in and be bold. That 250K check, it might only go 30x, whereas you're 150,000.

50 might go 100x, but 30x on 500K. Whoa, you know, returns the entire fund plus 50%. So you're going to know it's a winner. That's the paradox. Yeah. When you're seeing the winner. You know the winner. My management company is called Picking Winners LLC.

I've got an Amex. It says picking winners LLC. That's the goal. That's a good one. I actually bought the domain, Weback Builders, as a I was going to change everybody's email to. You and I think the same. We always like phrases or words.

I buy URLs just for fun. Me too. Me back builders is the one I bought recently. I forwarded to myself. You had another question. Yeah. I like wrapping out with you. You're good, you're good, uh, I'm just learning.

This is like all I do. I'm just love it. I love it. That's why I do a podcast. Who better to talk to you? I know, right? You get to like learn for an hour. I had Franks.

You know, from Snowflake again. You know, Snowflake, the crazy company. this guy Frank Sleuteman, have you read his book yet? Amped It Up? Read this book, Amped It Up. This guy's a maniac. He's like, I call him General Sleuteman. Incredible. Just like, I don't care what you think of how I run my company. I'm here to win, not make friends kind of situation. And he's just about building the energy in a company and the pace of a company. It's awesome. And I'll send you the podcast with him. It's worth listening to. This guy's a beast. Cool.

You had one more question, go ahead. Yeah. How much of your investment is. this stage is in the idea or the founder? Like, five million is sometimes pre-revenue, five million valuation is like, all right, there's some traction, but it's still the chance of that becoming, you know, an Uber is slim.

So is it the founder? Is it other people's cosigns? It used to be founders. I don't trust anybody else anymore. There's too many funds. There's too many games going on. People are sending you deal flow that are the ones that can't raise money,

and they invested in the winners in their portfolio, so they're sending you the negative portfolio because then you get to extend the life of their losers, or I shouldn't say losers, they are companies that are destined to not be able to raise money. They want you to fund them, but they didn't tell you about the ones that they funded and did an inside round on.

So, be careful. There's a little games we should be going on there. You know, as best as I can tell, now, people have decoded what it means to be a founder based on books like yours, mine, Y Combinator, content, podcasts. So people can put on a pretty, pretty good show.

So your ability to get snowed is pretty high now, right? People know how to tell a story, you know how to pitch. All that's been decoded and gamed and hacked. So I look at what my eyes tell me. Product velocity, product design, customers, and team members. If you look at those, it's kind of, you can't fake a team member who's a winner joining a company.

You can't fake a customer being delighted. You can't fake a product that looks gorgeous. and is functional and beautiful. And so I'm trying to believe from first principles what I can see, as opposed to my ability, which I think is great, where I thought was great, to read people because I have, in my later years as an investor, been snowed so many times now,

where people told me some great story, and they just, the products never hit 2.0, 3.0, they never advanced. They never hired anybody. And, man, they burnt money like drunken sellers. So, yeah. Anyway, just one theory is that founders have figured out how to snow people like us. Capital allocators.

They know how to put on the show. Yeah. How do I know any family offices? You know, great question. There's a database of them. But I think the best thing for you to do is to do what you're doing. Do the media tour. And every time you do a media tour, you come on this podcast, go on another podcast.

You're a great podcast guest. You're honest about your time, a nasty gal and girl boss. That's super fascinating. So I would just lean in sort of see. Into the media thing, which I am giving you the advice I need to take. I don't do media because I have so much stuff going on, but I do need to do some more media. I haven't done one press story about raising this fund, but I should do more. Yeah, I did tech crunch.

I'm doing this, but it's, you know, your team reached out to me and I'm so excited to get on here with you again. And I was like, well, Sophia's a great guest. Thank you. And you're a podcast shy. and I'm like, well, if I'm going to put money into this fun, at least I should get a podcast on it. I can't afford a publicist, so I'll just like DMs. You don't need a publicist.

Here's what you do. Yeah. You have to do it yourself now. You DM somebody who's a podcaster. This is my technique. I just tell people when I like something they do. So I just texted or I DM'd Rain Johnson, the guy who did knives out.

Cool. Yeah. And he's doing this new thing called Pokerface, which is kind of like Colombo, the TV show that I just love with Natasha Leon. And I just DMed him and I was like, I'm two episodes in, this is great.

And I'm just sincerely telling him that. And like, I think you just sincerely tell somebody you like their podcast. Next thing you know, you'll be on it. Yeah. You're Sophia Amorosa.

I'll get a list for you. Thank you. All right. This has been another amazing episode of this weekend startups. Everybody go to trust fund. If you want to get money or if you want to support Sophia's new fund, I'm in it. Andreessen's in it, Paraselton's in it. How much more do you need to know? Parishelten's in.

You're friends with her? Yeah, a little bit. Friendly? I'm closer with Carter, her husband. They just had a baby. Yeah. Yeah, they're great. She's kind of a genius. She's really smart. She's very smart. What is her genius? Is it brand? Is it? I don't know. I think it's like playing in pop culture. I don't know. She made it. pop culture. She invented that's hot. She invented the first

meme. It was like the first reality show. You know, the simple life, the simple life, yeah. No, she was like pioneering. And the baby voice is like, like she admitted when I interviewed her on stage at the Girl Boss Rally, like, yeah, there's a baby voice. Like, that's not really the thing. Oh, really? So that's like a interesting. She's just smart. She's a, you know,

I mean, I'd rather her, describe. You should have her on. You know what? I should. I went to a brother-air house once. I had a couple conversations with her. She's very intelligent. She's so lovely. She's interested in people. And I just think there's something there that is, I don't want to say savant, because savant kind of means like you're deficient in other areas. Yeah, I think there's a zone of excellence. Yeah, that's, but I want to use that word savant, but it does mean like, yeah, you're like, idiot savant, whatever. Yeah, people put the idiot automatically.

I know. She's a virtuoso is what I would say. There is a zone of excellence where she is unrivaled, which is capturing attention. Like even when they did a fake meme, there's one picture where she's in a club and she's got her arms up like this. And it was just like a blank t-shirt and somebody put on it, stop being poor. Oh, my God. It's not her. I didn't know that.

I swear I've seen that. The stop being poor meme is like unbelievable. And she's just like, yeah, I don't own a t-shirt that says that. Somebody Photoshop that. My God. The media so warped. Yeah. Well, I guess I'll go on a media tour and hope they don't skewer me.

I would say, like, you should be on Tim Ferriss, Lex Friedman. I just did both of those in the past year. They're really smart. You should be in, what will be another? You'll pull up the picture. You'll see it. You'll recognize us immediately. This is like from the 80s.

Yeah. Oh, Ryan Johnson. By the way, it's not Rain Johnson. It's Ryan Johnson. Oh, okay. Yeah, there it is. Stop being poor. Stop being desperate. That's my, by the way, when I was broke. I just had the picture of that on my desk.

And I would just look at it and be like, Jakehouse, not being poor. Yeah. Stop being desperate. Oh, is that the original? It would stop being desperate. And somebody replaced it with poor. I swear I've seen stop being poor. Yeah, for sure.

Yeah, stop being poor is the one. Yeah. Funny. But yeah, I would do. I think Lex Friedman would be interesting. He's like a, like, the ultimate AI interview. you were robot. Tim Ferriss was like the soulful OG. Yeah, I've been on Tim's,

but it's been so long and I don't really. I don't think he has people on a second time that often. I haven't stayed in touch with him, yeah. 20 minute VC would be good if you done that. I know, yeah, I was going to be on it. Harry actually on WhatsApp. When I sent him my first deck, he made a loom video like tearing it apart and was like, here's what you need to do. And I was like,

this is so cool. Thank you. That kid's amazing. He came to the intro like five or six years ago. He's like, no, Jayal, I just want to let you know, I'm a huge fan of your podcast and I'm gonna start a podcast that's kind of derivative or like inspired by what you've done and I don't know if that's true or not

but would you be a guest and I'm like of course I'll be a guest kid whatever you are and now this gets like you know I'm doing like 8,000 episodes a year I'm like rock on Harry Stevings he's nuts he's so that guy is always

yeah he like writes me back at hours that I know are not normal in London so I don't know I wonder if he sleeps all right everybody great to see you Sophia great to catch up and we'll talk soon

All right, how's going?