How Sophia Amoruso Turned a Side Hustle Into a $350M Brand (Nasty Gal)

On December 19. Based on the best selling novel, Amanda Seyfried and Sydney Sweeney star in the Housemaid. A wildly entertaining thriller about a live in housemaid and the wealthy Winchester family experience a twisted world where perfection is an illusion and nothing is as it seems. The shocking twists will leave you guessing until the very end. Can you keep a secret? The Housemaid Rate Rated R only in theaters December 19th. Get tickets now.

Your home should show off who you are, telling your story in every detail, meeting you where you are. Ashley has styles that balance timeless appeal and modern trends to bring your personal look home. Pairing eye catching design with features like stain resistant performance fabric, Ashley offers well crafted, affordable pieces built to stand up to real life. Plus they provide fast, reliable white glove delivery right to your door. Visit your local Ashley store or head to Ashley.com to find your style. We are in a world where really anybody can start a business.

Our guest today is Sophie Amoruso, the powerhouse who built Nasty Gal from a thrift store side hustle into $100 million global sensation and kicked off the hashtag girlboss movement.

She's a bestselling author and Netflix inspiration and now she's empowering and investing in the next wave of founders with her platform business class.

I'm Sophia Maruso. Welcome to the Vern Outs.

I want to dive right into you being an ebay seller. How did that start and how did that transition into becoming, you know, the hundreds of millions of dollars brand that you built with Nasty Gal?

Well, it took 10 years. I was 22 and I was like working in the lobby of an art school. You know, I wasn't in college. I wanted to go to art school and I got into the San Francisco Art Institute in North beach, which was an incredible art school. And then CCA in Oakland, which is an awesome art school. But it was like 50 grand a year. And I was like, I didn't have any credit. Parents didn't have 50 grand a year. So I ended up not going. And I worked in the lobby of an art school, not because I wanted to work in the lobby of an art school, but because I needed health insurance. And I worked there for three months. And during that time I had all this time to kill on eBay and MySpace, really. And I was like getting friend requests on MySpace from eBay sellers who are selling vintage and trying to like promote their business. Just like an Instagram account might try to follow, you know, you and be like, hey, pay attention to me or whatever. And I clicked through and I saw what their auctions were going for, because they were starting the bids at, like, $9.99, and it could very well have sold for $9.99. But these girls, like, auctions were going for, like, hundreds of dollars. And to me, it was like, I know where to find this stuff for, like, eight bucks. I spent enough time in thrift stores. Like, I loved vintage. So I was like, quit my lobby job and I launched an ebay store called Nasty Gal Vintage. Not everything worked at first. You know, I wasn't like, I'm gonna be an entrepreneur. I was like, 22 and just like, oh, I. I, like, don't want to work for anyone else. I'm actually not capable of it. Maybe I can, like, not work. And then, you know, fast forward. I'm like a CEO and like, the COVID of magazines and stuff, which, like, you know, is still just kind of wild to me, but, you know, bootstrapped it. Cause, I mean, I didn't know what venture capital was. And I wasn't like, I'm going to build a company that does $100 million in revenue. Like, I would never have even had goals like that. Cool. Maybe I can, like, work for myself. And I was like, you know, I remember, like, checking auctions on my BlackBerry pear. Holy shit. These auctions are, like, going so high. So after a little while, I, like, figured out what worked, built my own brand, reverse engineered what had worked for other people but didn't do the same thing. Was really resourceful about, like, sourcing vintage and somehow really good at, like, copywriting and good enough at photography and good enough at a lot of things. Just kept going. And year one, I think it was, like, 75k in revenue, which I was like, I just kept the money in the company. I didn't, like, want things. I was, like, 22 and too busy like, having fun with my head down, being like, oh, my God, this is crazy. Something's working. And then year two was like, 250K. Wow. And then it was 1.1, and then.

1.1 still through eBay fully.

No, I left eBay, like, mid 2008. So I started it in late 2006, left eBay mid 2008, and then launched my own website. And it sold out day one.

And were you still selling vintage or did you start selling something else?

When I launched it, it was just vintage. And then I was like, oh, shit, I need to buy depth. And went to my first TR show in Vegas called Magic. And at that point had spent so much time understanding what my customer wanted, which was like mvp, you know, you could call it like, oh, wow, I just sold. I did something that didn't scale. I took photos of one thing and I measured it and I wrote a description and, you know, and to be able to buy six and smalls and mediums and larges and have things that like, I could take a photo and sell, you know, multiple items of. I was able to really scale the business, being able to curate other brands. And eventually we had a design team and we had our own brand. And then venture capital came in, I think in 2012 when we were doing about 30 million in revenue. And I had like bootstrapped it and owned 100% of it. And the first money in was out of a growth fund. And they said the company was worth $350 million five years in.

It's so interesting because 2% of VC capital goes towards solely female founded businesses. It's ridiculous. And it's about 12% that goes to businesses that have like a male and female co founder, which I think is just a huge crime, but then also a huge opportunity within the market to different things and to try different things that actually serve this customer In a lot of ways. Our target consumer that we're looking at is very similar for Fia. We're looking at a girl who's obsessed with shopping. She wants to get the best deal. She wants to, you know, have the.

Hottest dress for summer.

I think it's really interesting because talking about really getting to know your customer, people talk a lot about product market fit, but not founder market fit. And you had that because you knew, okay, what's hot, what's cool. I want to go back to the beginning of the business when you transition off of ebay and you start doing your own sales. Who's your first hire and how. How do you pick that person?

My first hire I found on Craigslist.

You found your first hire on Craigslist?

There weren't like, I don't even remember LinkedIn being a thing. And I was just looking for a girl who like worked at a shop, you know, someone to show.

So what did you want them to do?

I was like, the things that I don't have to do.

Yeah, yeah.

And I still had to buy, I still had to style and, you know, photograph everything. Like all the creative stuff, but like steam clothes, write product descriptions. But even then it was like I was very specific about how I wanted things done. I didn't know what a standard operating procedure was, but I like, like call it glitter, not sparkles. So, yeah, customer Service, shipping, you know, ordering any kind of supplies we needed, steaming stuff. So. And her name was Christina and she had worked on a store on Haight street and she actually knew about the trade show that I went to and she was the person who told me about it. And I remember I was like, I committed to a full time job for someone and I, I wasn't even paying. I was paying her more than I had made and I think it was like $16 an hour. Like I was paying her more than I was paying myself. I was like, oh my God, this is so scary. Like, what if it doesn't work out? Like somebody's livelihood is on the line. And like, little did I know that that was like, you know, the first of hundreds of people that I would end up employing and livelihoods that I would be somehow responsible for.

And how much money did you start making before you made the decision of it's the right time to bring on someone?

It was like probably 250k that year or something. It was just basically when things were breaking, when I couldn't keep up with customers. It was like, you know, I think, you know, the company was just exploding and I couldn't keep up with the demand. And that was, that's like, I think the best time to hire people rather than like hope it works out and hire people ahead of it working out because, you know, it's like, that can be very expensive.

I think it's so important to stay as lean and scrappy as possible in the beginning because you need to learn everything yourself. I feel like if we were in a position where we had extra resources, then a lot of stuff that we ended up up doing, we would have delegated. And I think it's such a valuable skill to really know your business in and out so that if people are taking things on and they're floundering or they're confused, you can step in and actually coach them. Building up your own skill set makes you more valuable as a founder, as an employee, whatever it might be. Being scrappy prevents you from getting into situations where you have a bunch of money and you end up deploying it in ways that are inefficient just because you have a true understanding of like, what is it that the business needs. Obviously it's unfortunate and stressful when things start to break, but it's bad than things not working and then being stuck with a bunch of people who have no idea what to do with their time.

I also think you guys are building software. There's a speed there's speed's really important. You have engineers, you're never gonna know what the engineers know. So building ahead of that or having people, I mean, it's just what I was hiring for was like a bootstrap business. It was someone to do really basic stuff. So if there were things that, from day one had to happen that I didn't know how to do, I wouldn't have had the capital to do. But if you do and you're building, I think a technology company, it can be, like, very different. I mean, there's a reason why a lot of software companies are started by engineers.

You know, I mean, I find it so interesting because I love what you said about you had these very specific inclinations where you really understood your customer to say, call it like glitter, not sparkles, etc. Because you actually knew it was resonating. And something I wanted to walk back to that. I'm curious about that. When I was reading about you, I thought was really interesting is that you worked a series of, like, different odd jobs and you were doing a lot of things before you ended up starting Nasty Gal. And correct me if I'm wrong, I thought I saw, like, a viral Instagram reel where you said, I used to be a stripper. Which I was like, that is so cool. I mean, I'd love to just better understand you as a person and the things you did before you started Nasty Gal. Do you think there was specific jobs or specific things that you did early in your career that kind of helped you become an entrepreneur and taught you things?

I think so. I think I tried to cut corners, and I think that just doesn't work, like, long term. It just doesn't for me. My idea of a perfect job was, how little can I do for as much money as possible. Can I just sit here and do, why would I work harder if they're not gonna pay me more? There is a theme of that. There's the lazy girl whatever, which is cute when you're 20, good luck when you're 30 kind of a thing. Or that just is not gonna scale at some point unless you become a trad wife or whatever. Just doing things that didn't work. There were things like I worked in a bookstore and they taught me take someone over to the whatever nonfiction section instead of point basic customer service stuff that I think I ended up applying to the business even though it was a digital business. That really helped me. Yeah, I was a stripper for a few months in Portland. And honestly, like, nobody fucked with me. It Was just fun. I got to, like, dance to music that I liked. And I was the person like a few years prior who was like, oh, my God, don't look at me. Like, if I was, like, making out with somebody, I was like, I'm going to, like, get up in the dark and go to the bathroom or something. I was just, like, not comfortable with my body. And it. It was kind of like exposure therapy in a way where I was like, also, again, I was like, doing. It wasn't as little as possible. Cause it was actually work, but it was just fun. I didn't really engage with anybody there. I was just danced and went and had a white Russian in the back room and then did it again or whatever. It made me really comfortable with my body in a way that I'm super grateful for, because I think that's something that can take a long time for people.

I saw this viral tweet yesterday. I spend, like, X or whatever. I spend way too much time on it. But it was basically saying, this stripper taught me more about sales than anyone I've ever met in my entire life. And it was talking about, like, building an emotional connection with someone and understanding, like, the levers to pull to really make someone trust you. And he was saying how he learned it all from a stripper, and he learned more than any sales coach he had ever talked to in his life. And I just thought it was so funny, but also really interesting because I think it's so unexpected, the things you end up doing in your life that end up teaching you so much. And I feel like, especially for you, you had such an untraditional trajectory that I'm kind of curious, like, if you were to peel back the layers and especially give people adv, like, what kind of things you would say are important to do when you're young to set you up with a good foundation if you want to be, like, a founder or go into entrepreneurship.

I probably. There was no emo. That's fine. But I never connected with anybody totally. No, I don't think I learned that. I think I learned that way later. For the record, I wasn't like, building, which is, again, it's fine. But I didn't. I was not.

No, for sure. It was just so funny.

It was like a pretty in ambitious stripper. I guess there is a lot of people get really excited hearing stories like mine where it's like, oh, just get started with no experience and like, no, like, no education. Like, my story is such an outlier. And people were so attracted to it because it inspired a girl with like a login to shopify or ebay or whatever to start a business, you know, which was not possible before Marketplace. Like ebay was just digitally. It was just like not. You couldn't just stand up a business. You had to like go get a physical retail space to sell vintage, which was. Was like, I would never have done that. And so we are in a world where really anybody can start a business. I don't think education is overrated. And I especially think that if you can, when you're young, learn some chops on somebody else's dime, work in a company, even if it's for a bad boss, experience what leadership looks like or shouldn't look like just by exposure, that when you go become a leader when you start a company or you need to manage somebody or there's a certain kind of domain expertise that you want to have cultivated before you move into your career or starting a business, like you've done that and gotten paid to do it, rather than putting like all the risk up front and doing it for the first time after you start your business. You know, that works differently for different people. It ended up working for me, like to a point. But I think, you know, the whole like serendipitous founder story of just like, you know, you know, dropped out of school, whatever thing is like a little over glamorized. Yeah. It's like I really wish I had that foundation because it would have given me a lot, lot more empathy for the people that I was employing and a lot more chops to be able to kind of run that team when the job became about more than like shipping stuff or things that I had already done myself. Right.

Do you feel like there's mistakes you made as a boss that you're looking back like, wow, I wish I had done this differently.

Yeah. I really wish I'd coached people more, didn't know how, I didn't know what that meant. I hired people that were, you know, three times older than me or whatever, twice as old as me. And I was like, you're gonna diagnose the business and do what it needs to happen and you're gonna work with the other people like a grown up and coordinate and it's all gonna happen. Right. I just thought that's what like grownups with like, like lengthy careers did. And nobody had to tell me what to do. So I just like didn't understand that even executives had to be held accountable and that they actually want that. I was like, oh, they're gonna be so insulted if I'm telling them what to do. Like, they're, they've got their, like, shit together, right? Well, you know when people even like, really, really great talent doesn't fulfill on what it is that they set out to do. And you haven't like, led them to it or coached them or checked in and talked about milestones and just been like, oh, cool, you're gonna go do that. It doesn't set them up for success. I think it's easy to be like, well, you fucked up. But actually that's just like, people need more than that. I could have given people more chances kind of in the same. I'd be like, this is absurd. How did this happen? If you're, I just kind of whacked people and it puts a business at risk. When you just like, remove someone from the company. It's like a game of like Jenga. It's like, you know, sometimes the best thing for the company is to keep the person that's not working out in that role until you find someone to fill that role, because you can remove someone from the company. And then the people under them are like, I got all this responsibility, like, what they. The, what the hell? And then they're like, I want a raise. And you're like, you're not qualified. And you're like, now you're going to get a new boss. And they're like, we don't, they don't know what we know. And it's like, but what got us here is not going to get us there.

On December 19, based on the best selling novel, Amanda Seyfried and Sydney Sweeney star in the Housemaid, a wildly entertaining thriller about a live in housemaid and the wealthy Winchester family experience a twisted world where perfection is an illusion and nothing is as it seems. The shocking twists will leave you guessing until the very end. Can you keep a secret? The Housemaid Rated R. Only in theaters December 19th. Get tickets now.

Meta is investing $600 billion in AI infrastructure bringing jobs to communities across America. Phil a Meta building engineer in Las Lunas, New Mexico, says welcoming Meta into our community is creating more opportunities. Learn more@meta.com buildingameric One iced coffee, 99 cents, please. For real? No way. Mmm.

One iced coffee, 99cents, please. For real?

No way.

Mmm.

What a deal. Your new morning groove. Iced coffee from McDonald's, any size for just 99 cents till 11am Price and participation may vary. Cannot be combined with any other offer.

I want to continue to kind of hone in on your journey with Nasty Gal, was there a specific milestone that you hit, especially when you were initially bootstrapping, where you thought, oh, my God, like, this is actually working. This could actually be the thing that I do full time as my business.

The moment where I was like, oh, wow, I can do this full time, was when I launched the website. It was when I left ebay and I was doing it full time, where I was like, oh, shit.

And why did you leave ebay?

I had a customer base that was coming to ebay. For me, selling in a place like Etsy or ebay or Poshmark or any of these reseller sites is great because people, there's a sense of discovery, and if somebody's looking for X item, they can find it. But my customers were coming for, like, what I was curating. And so I think ebay was good in the beginning to get awareness about the brand and to find customers. But ultimately I was like, why are people coming here for me? And that I'm giving my business away to, like, you know, suggested sellers, suggested other shops, suggested retailers. And I was like, I just got kind of selfish about it.

As you should, though. It's your business, right?

I was like, I'm doing more for ebay than they're doing for me at this point. Also. I was like, I wasn't planning on leaving ebay. I was gonna, like, launch the website and still sell on ebay. But I was like, I'm gonna market the out of this website. And so I was leaving feedback for customers that was like, check out Nasty Gal Vintage coming soon. And ebay basically suspended me for doing that at the same time that the website launched. So I didn't really have a chance, a choice to go back. So that was really why I, like, left left ebay. I didn't really have a ch. Also, when I launched the website, everything sold out within hours. So who, what, where and Daily Candy were really huge at the time. Who, what where is called Click Media Group now, and they own, like, Birdie and all these other platforms. Katherine Power went on to, you know, found Merit and Aveline wines with Cameron Diaz. But at the time, like, Cartier would pay them I don't know how much money for a dedicated email. Okay, here's today's trends. It was really mostly a newsletter business.

What year is this?

2008. And so she was a customer, like, Anne Hathaway was a customer, like, on ebay, you know, who later came and shadowed me for the intern, which is. Was kind of like, interesting.

Anne Hathaway.

Yeah.

That's hilarious.

Yeah, yeah, yeah. She came to our offices and, like, followed me around for a day for the role. And Nancy Meyers came to the office.

How did all these people find out about you?

She found me on ebay. It was just. It was organic. Like, people talked about it. People thought it was cool or it stood out on ebay to them, or they were looking for something, you know, similar. But who, what, where sent out a dedicated email about Nasty Gal's launch to I don't know how many people. It was one of the biggest fashion newsletters out there because the co founders were customers. And that was just like, Kelly Ripa's stylist was calling. She was like, do you have that motorcycle jacket in an extra small? And I'm like, it's one of a kind. No, but, like, what the fuck? How did you, like, get my number? You know, and it's like, hollywood, that's crazy. So it was just, like, sitting in this, you know, little warehouse up in Benicia and. But fuck Bay Area. And, yeah, that was when I was new. I was. That was when I knew I was onto something.

So it was really that you were intentionally curating, and then these celebrities, like, organically found you, and then it led to more people finding out through referrals or. What do you think was kind of that critical unlock that made more people discover the brand?

Yeah, I think, like, I mean, when we raised money, it was something like. Like 60% or some crazy number was organic traffic. We weren't really running any paid media. So at the time, it was just, you know, people didn't. What? MySpace wasn't even around at the time, so people were really just finding us through word of mouth. It just became like a cult, like, obsession. Yeah. And eventually maybe social media, but it really was word of mouth. You know, people wearing Nasty Gal, somebody asking, you know, where did you get that? And the name of the company itself, I think, lended itself to a certain amount of virality. You know, girls would get a package and people would be like, what's that? Or their parents would see something on their credit card and be like, what are you doing? And so I think that really ended up standing out because at the time, I mean, everything was just really generic. It wasn't as hard to stand out.

And is there a reason you named it Nasty Gal? How did you land on that?

The other name I almost called it was I Heart Vintage.

No, I like Nasty.

So there I worked in a record store in San Francisco for a little While. And there was an album I discovered there by a woman named Bette Davis, who had been married to Miles Davis for a short period of time. And she was like, reportedly too wild for him, but was this incredible front woman, funk singer, super duper stylish. Like, if you look at photos of her, she is so fucking cool. And her lyrics are like, I don't want you back. They're all just like, you know, it's like, your mama wants you back. I'm the best thing you've ever had. I don't just like really kind of ballsy lyrics. And the spirit of that was just what I wanted to infuse into Nasty Gal. The brand was very. And I hate the word edgy now, you know, but there was an edge to it that didn't really exist anywhere else. And the name very much inspired that.

Walk us through. You were talking about all these different revenue milestones that you were hitting. And then. So when did you make the decision to raise venture capital and do you regret it at all?

You know, I owned 100% of the company when they valued at $350 million. Had I sold all of the company when it was worth, even if it was worth $200 million to private equity, or had like, even $100 million, like, that would have been a ton of money. When I raised money, you know, I had already built something, so I wasn't really pitching. I was just like, yeah, this is what I did. You know, that was when Jeff Jordan from Andreessen and Jeremy Liu from Lightspeed, like, everybody flew down to LA to be like, who is this freak? What is this phenomenon? How did she build this thing? Where'd this come from? It should be venture backed, but it's not index. A bunch of them leaned in. I found a term sheet from Benchmark and I don't even remember getting one. I was digging through my Dropbox recently.

And it was like, okay, wait, I can raise a bunch of money. I still own 80% of the company. I raised 50 million and I owned 80% of the company. And I was like, I control the board, so what's the downside here? So I sat down with my new investor, which was Index Ventures, and my COO and my CFO at the time was like, okay, let's project next year. Let's just round up by $100 million. So let's go from like 28 to 128. And then we hired into it and we spent money on paid into it, and then the company became less profitable. And you hire 100 people in a year, it is like, you know, you better have really good chops to do that and have like new teams and new leadership and, you know, first, you know, early employees, getting bosses for the first time and no systems and like no processes. And it was just very much kind of like a homegrown business. You know, when you get started, it's like create processes as early as possible so that when it scales, people can take that and run with it. If you're trying to retrofit them into a business, it's really hard because there's already so much complexity. And getting people to like buy into that and do something a new way is a lot more challenging. So that just became this like really loud people being like, I'm doing the same thing that that person's doing. And like, I thought that was my job. And all kinds of things that happen when you hire a lot of people at the same time. And things that happen just when you have people, period. The expectation was that I build a billion dollar business next. And that was never my aspiration. Like, I was fine with the business I had built. I wasn't like, oh my God, if I don't build a hundred million dollar revenue business, I'm going to be a failure. I was like, dude, this is, is amazing already. And you know, I was told I could and I would and it was basically inevitable. And it's just not as simple as maybe it, it was made out to be.

And so by the time you're 32, you guys are doing over like a hundred million dollars in revenue. You also have to guide the business through bankruptcy. Was there a point where you're like, okay, this is going the wrong direction or we're being pushed too fast to scale? What did that look like?

I mean, you don't go bankrupt overnight. There were opportunities to raise money at a lower valuation that we had raised, 200 million even, which is like not a failure. Right. But that would have meant my investors, what they invested in was worth less than what they paid, which they don't want. And so even though I had control of the company, the advice I got was like, don't do that. Some conversations I think that were had when I wasn't in the room, even though I controlled the company, where my investor was like, you know, to a potential new investor who would have been like a strategic apparel, like veteran type of like person company, whatever was like, if you can't invest at 350 million, don't bother showing up kind of A thing. And I learned that, like, later on. And so there was a certain amount of like, cock blocking that happened that I don't think I knew about because I would ask that potential investor later on, like, what happened? And they were like, this is what happened.

Because they didn't want to raise on a down round because their reputation.

Because they would rather. Venture capitalists would rather just show their investors that what they invested in is still doing fine than mark it down and say, oh, shit, like, the fund that you invested in is worth less or this company is worth less. It's a high risk business, venture capital. So they expect a number of them to flame out. So I think, I think some venture capitalists would rather like, hold their investment at cost than mark it down and give the company an opportunity to, like, get back to where they were. And then at the end, there was like a series of Hail Marys that were like, this person's ready to buy the company. You know, here are different opportunities. Someone did invest. Ron Johnson, who had been at Apple and was like a retail veteran, came in and invested with his, like, crony. And they were like, we're gonna turn it around. The company had taken on some debt and he's like, we're gonna sell it. I remember one of his guys came in and I was like, what's the chance we're gonna sell the company to these people? He was like, 100%. And I was like, nothing's a hundred percent. Like, oh, God, you've been along longer. You've been alive longer than I've had a career.

Yeah.

And I know that most deals fall apart. So that was when I was like, oh, shit. Like, what's happening? I had taken myself out of the CEO role two years before the company fell apart. I didn't want that job. I didn't enjoy it. I was in over my head. I was very aware of that. Nobody pushed me out. And I hired a CEO who had been our chief product officer, who was an incredible merchant, incredible eye, incredible taste. We were making really beautiful things. Maybe wasn't the right CEO think, you know, that's a huge risk to put somebody else in that position. Would I have pulled it off had I not done that? Would the fate of the company been different? I don't know. But I knew that I hit a wall and I just straight up didn't want that job.

I mean, how long after? Eight years.

I was like 32 when I left. Nasty gal after 10 years.

I mean, 10 years is crazy to be that long when you're like, oh, this isn't the vision I had for the company. And now you're forced into what is a grueling job of taking this to. Okay, okay, let's make this a billion dollar brand.

Yeah. I was like, I didn't know what I was signing up for. I didn't know that that job was gonna be as gnarly as it was. And as a founder, by default, you're the CEO.

Yeah.

And it's like a founder and a CEO aren't necessarily the same thing and you don't have to be in that position. I think when you have a co founder, it's amazing. You know, I wish I had a co founder, especially someone who had more experience than I did, but I was very much a founder, very much a creative, but I wasn't a CEO. And now, you know, I have a venture fund called Trust Fund, and I invest at the early stage because that's just where I like to play.

Yeah.

And I get to do it over and over because things I do tend to be successful, which is awesome. But then you inherit this. I inherit the things that I don't like. Which is the next phase, which is the growth phase, which is exciting the first time, but not something I want to do again.

Of your portfolio, what's an investment you've made that you're really excited about? Right.

Yeah. There's two. One's called agree.com and I think they're going to replace DocuSign. It's like you load a PDF in, everything becomes editable and you can collaborate and you. It has version control, so you can see like anytime something's edited. Whereas right now, if you like go into word, you can't see, and it's also connected to payments, so you can sign a contract and as part of the flow, your customer say, it's like a SaaS customer or you're a consultant. Even when they sign the contract, basically they have to pay when the contract is the invoice and you can set up recurring payments. And so instead of signing a contract and then sending them an invoice and then chasing them down for payment, you're able to do that all in the same flow. And so I invested when you. These guys just had a deck and they just raised a big seed round. And so that's really exciting. They did that in a year. And then there's a company called Nectar Social and it's these sisters based in Seattle who worked at Meta, who worked on the Instagram messaging product, and they saw a Huge opportunity in selling via dm. Not like customer service or, you know, hey, how can we help you? But they found out how to connect shopify data at the user level on Instagram and you can look up a customer's entire shopping history and do like, you know, specific targeting to them and sell via DMs. And they just raised a seed round actually from Google Ventures and True Ventures. And I made those introductions and that makes me very proud to send a company that I invested in that no one's heard of with a deck to like, the big, big shots who aren't going to invest because, like, we're friends but are like, oh, wow, you picked a winner. As an investor, that makes me very happy.

As it should. You're bringing them into the forefront. That's amazing.

But as a venture capitalist, I don't operate the same way that my investors did. So I'm like, a lot of them say they're founder friendly, but I think I actually am. I'm just like, you know, raise a lot of money now. Don't optimize for valuation. Extend your Runway as far as you can because sentiment shifts. Companies go up and down and just be careful with valuation because the expectations are really high for what you need to do to get to the next round. And I'd rather a company survive than be able to mark it up and look like I'm successful as an investor.

How can I help you today? Hey, I need to talk about my loan.

No problem.

So I got the email. Sandy Spring bank is becoming Atlantic Union Bank. That's right. And will you still be your banker? Of course. More branches and ATMs.

Way more.

Still community driven, still live here, still give here mobile app easy.

Everything right at your fingertips.

And what about my business?

Always here to help you reach your goals.

Sandy Spring bank is becoming Atlantic Union Bank October 2025. Same bankers you love. With even more to offer, Meta is investing $600 billion in AI infrastructure, bringing jobs to communities across America. Phil a Meta building engineer in Las Lunas, New Mexico, says welcoming Meta into our community is creating more opportunities.

Learn more@meta.com buildingamerica.

If your appliances can't handle the holiday hosting heat. December deal drops at Lowe's makes upgrading easy. Get up to 35% off select major appliances and rewards members. Save an additional $40 on the whirlpool electric range and the over the range microwave. Plus get up to 60% off select ladders so you can deck all the halls. Lowes we help you save valid through 1210 while supplies last selection varies by location. Loyalty programs subject to terms and conditions. See lowe's.com terms for detail.

Walk us through kind of your inflection point and transition. So Nasty Gal started to plateau at. Plateau at around, like, a hundred million dollars in revenue. What ended up happening with the business? And then how did you end up moving forward with your career?

I mean, ultimately, it got to a point where I was like, okay, we can't fund the company anymore. It started to lose money. The responsible thing you do when you can't pay your vendors, like, really as a fiduciary, is to declare chapter 11, kind of that's the best thing to do, because otherwise, eventually you can't pay people. And so I remember I was in Australia actually promoting my second book, which was called Nasty Galaxy, Girl Boss. I'd written a book called GirlBoss, which spent 18 weeks on the New York Times bestseller list and sold half of the. I read Girl Boss.

I read Girl Boss when I was literally in high school.

I love that book. Yeah, I mean, it was 2014. That book came out 11 years ago. It's pretty wild. And so I had gone off as an author and done other things and moved out of the CEO role. But I was on the board. And I remember having a board call minutes before I was going to walk on stage in front of a thousand women to promote a book and talk about all my success. And nobody knew how much the company had been struggling. And I remember that call. And the call was the day Trump was elected and Hillary Locke, and I mean, it was just the worst time. My husband. I had gotten a divorce that year. It was four months before a Netflix series about my life came out, talking about this, like, girl who started a company called Nasty Gal. When for the first time, I stepped off the board, I was like, I don't know how to do this process. You're not going to need me here. And after 10 years, I did. I think it was selfish, but I was like, I just need to preserve myself. I could have been there and been a spiritual leader and talk to the team, but, like, I wasn't. I hadn't been the CEO for a while, and I was like, I'm just gonna go kind of into my own mode. And, you know, I'm someone who likes to be occupied. I find new things to be inspired by. In some ways, it was a relief because I was able to move on because I felt so stuck in the company, even though, you know, even when it was doing well, and especially when it Wasn't doing well. I was like, I'm. My hands are tied. Like, I don't know what to do here. And so not long. I was like, this Netflix series is coming. I'm an opportunist. So it's like Girlboss has, like, so much brand equity. You know, people were talking about that more than they were talking about Nasty Gal. It's not like Girlboss was even a business. It was like a book, and people called it, like, a movement. And so I was like, I'm gonna throw a conference, and I got, like, brand partners. And, you know, so I think four months after Nasty, I left Nasty Gal. I was like, I'm gonna do this Girl Boss thing. And it was basically a media company. I had a podcast for five years called Girlboss Radio, had, like, 22 million downloads. You know, I think about doing a podcast again, and it's like, it's a lot of work. But I moved on. And, you know, we had a newsletter, we had an editorial content. We did events with, like, 1500 women in LA and New York. We did really big brand partnerships, raised a little bit of money, eventually sold the company to, like, a hold a media holding company during COVID And so I did GoBoss for about three years. And then I was like, I just want to do lightweight things that can scale without a big team and use, you know, digital products to do that, you know, and now AI it's like, you know, it was like, I started an online course, and, you know, that was a very easy thing to put together. I was like, I'm going to scale my knowledge. So I started an online course called business class during COVID after I left Nasty Gal. And, you know, I've had, like, 3,500 students in there, and it's like, I've put all of my knowledge into this one thing, because I get asked advice all the time, and I just can't respond to everybody. But I am, like, optimizing for.

You know, as much impact as possible with the smallest team.

This is so interesting for us because we're at the beginning of our journey, right? And I feel like already some of the things you're talking about, hiring people and learning how to coach people, are like things, frankly, we've failed at having to learn today. So the fact that you've had this business and gone through all of these different chapters and frankly, found success at each and every one, I think is a huge learning lesson, especially because for us, from a young age, wanting to be an entrepreneur, when we were at Stanford. I was reading your book. I was following your journey. So to be able to, like, talk and go through those different milestones is really interesting for me.

And it's like, what I enjoy the most. It's like, I don't have a warehouse full of clothes, my inventory, my experience, and that's like, super high margin. And it's just what I enjoy doing. Like, it feels like it was all worth it. When I can pass on, like, anything that or make an introduction that, like, changes the trajectory of a company, that's what's really gratifying to me now. And it's like, such low effort to make such a high impact. Everything that could have happened probably happened. And to be able to take that and share with a new generation is, like, super rewarding.

What would you say your biggest piece of advice for young entrepreneurs today is? Who are getting started? Would you open an ebay store? What would you say?

I think most of the people listening to your podcast, like, 99% of people, are probably not going to raise venture capital, probably shouldn't for the type of business they're starting. Most people who are business owners are like, they're entrepreneurs, but they're not. Like, they don't need venture capital. So I think there's a lot of glamour around raising money, but for most people, you don't need to do it. And you can spend a lot of time thinking about it and talking to people. But to be able to stand up a business today with AI and with the digital tools, whether it's an online course or, you know, you're selling clothes online, or you want to get something, like, manufactured even, like, there are so many resources for you online where you don't need as much as you think you do, and you can be scrappier than you think you have to be.

I'm also curious, like, through all of this time, do you feel like there's really consistent bad advice that people give that you would want to dispute or that, like, you tell the people you work with differently?

I just feel like advice is different for everybody, which is why it's so hard to dispense at broadcast level. Like, I actually think advice can be dangerous. So listen to advice, but choose what advice to listen to that's right for you. Listening to yourself and trusting your gut and doing what you know is right for your business is more important than getting or taking advice.

That is good advice. That's pretty good advice.

Yeah. Just like advice is overrated, can be really trite. And I think everybody Wants a silver bullet. If you fail, at least you can blame yourself.

That is true, yeah.

Because I really want to dig into also where you are at now, because I think that's also super fascinating. I mean, you built girl boss, now you're running your own venture fund. You're also doing these business classes. Like, you are doing so much. And what I was really interested about was that you, like you were saying, you literally four months ago, decided to leave LA and move to London. Why did you decide to do that? Kind of. What role did it play in your career?

I mean, I'm able to work from anywhere and I think that applies to a lot of people and what a lot of people want. And for the majority of my career, I was. Even though I worked for myself, I worked for my team, I was in an office, I had to be physically present and I was in relationships. So it wasn't going to be like, babe, let's move across the world. So I found myself, like, single in this house that was kind of too big for me, that I'd never lived in alone. And I was like, oh, shit. Like, I can be wherever I want and I can, like, lease this house out and make passive income and it'll, like, pay for a flat in Notting Hill and I can go to Italy in two hours. Like, that's crazy. I was in LA for 14 years and I love LA, and no part of me was like, I need to get out, I need to change my life. I'm dissatisfied. If I move, it's gonna change something. Like, actually, I was just like, oh, because I want to and because I can.

Now. When you look at where you're at in your career, what are you most excited about? I love seeing your social media and you saying, like, you feel like you're on your 3.0 version and you're doing the things that feel fulfilling. Like, walk us through what that means to you.

I think I'm just optimizing for impact because, like I said, it's so gratifying. And if I can do that through investing or I can do that just through creating content, or I can do that through, you know, I have, like, one consulting client. Like, I'm not really a consultant, but if there's a way that I can pass on my knowledge to other people, that makes me very happy. If I can do it while also having flexibility to be spontaneous, that's also at the top of the list. And the least number of people I need to do it are like, those are kind of, I think the three things, because to me, the ultimate luxury is spontaneity. Get out when I want to. Like, my boyfriend was like, I might be in Turkey for a job. Want to come? I'm like, I could. Yeah, you know, not something you can do over here. I had a friend who was like, I'm doing my 40th in Egypt. I didn't end up going, but it's like, oh, that's five hours. Like, that's crazy. Bucket list items when you live in LA are like weekend trips here. I'm just kind of fully taking advantage of that while building the fund and investing in amazing entrepreneurs and helping them build their companies and eating good food and riding a lime bike.

And how did the fund come about? Why did you decide to start that?

I'd done a bunch of angel investing, so I invested in, like, liquid death and ate sleep and, you know, some software companies, some consumer companies. And it was like, okay, I can't eternally keep angel investing, but I really, really enjoy this and went out to people that I know primarily. And, you know, so my investors are like Marc Andreessen and Jeremy Liu and Jeff Jordan and Chris Dixon and Andrew Chen and like, half of Andreessen and like, Jason Calacanis and David Sachs and like, it's kind of an incredible. It's like the Midas list of people who showed up and were like, hey, we support you. And for them, if they lose their money, it's like a rounding error. But I think they knew that. He's like, I have access. So it's like, what do you have? What are your advantages? I was like, I have access. I can make an impact both through helping the companies and I understand, like, their end consumer, because I was that when I was building my company. And I can amplify their companies to an audience that's really qualified and interested in the kind of things that they're building. And then I can, like, go upstream and make introductions that, you know, in the first fund, I've been able to prove are, like, not just valuable introductions, but, like, really qualified introductions to the kind of people who, in response and these are the best introductions are like, oh, my God, thank you for introducing me. It's not like a favor to the founder. Everybody, everybody, even on the other side who have made the introduction to is super grateful for it. I have, like, investor thesis fit. And, you know, so there's like, you know, product market fit, there's founder market fit. But I think I have, like, investor thesis fit kind of unlocked with trust fund and it's also just another fun brand to keep building.

Do you feel like you're now doing things differently than your investors and walk us through what those things are?

I think so. I just had a retreat in Mallorca for my founder and it was literally like, it's a house, it's a residency, show up, cowork, we'll go eat some dinners, we'll go to the beach. But it wasn't like we're gonna have talks and it's gonna be super structured. And at 8am there's like breakfast that everybody, you know. Cause I go to things like that just to network and to hang out. Everybody has phone calls to make and everybody's busy. So I was like, just come hang out. And that's kind of what everybody wants. And we made some content. I haven't posted it yet, but I think with Trust Fund there's an opportunity to just like create experiences founders that like, bring them together in a way that just feels really organic. I don't want my founders to raise at crazy valuations. The job of a venture capitalist is, you know, historically to make it look on paper like what they invested in is worth more. Of course that's what I want and I've done that. I want to be able to report that to the people who invested in me, but not at the expense of what can come down the line where, where a company goes from like 0 to $100 million valuation and doesn't necessarily have and has no revenue. I mean, you own 10% of a billion dollar business, you're fine if it sells like you're in good shape. So if you end up owning less of the company because you didn't have the highest valuation for everybody here, it's called dilution. You can ask ChatGPT about it.

I think it just gives you more optionality and there's more people who would want to invest later on and they're not like, sorry, we're not going to pay that. Because sentiment can shift. Like maybe there are more competitors or maybe retail's down or, you know, there can be reasons a year from now or two years from now where people who are really excited about this kind of product, like maybe aren't and maybe they will be again in a couple more years. But you just have to be able, it's more important to survive, you know, than it is to raise as much money at the highest valuation possible.

I mean, Forbes once valued you at $230 million. And then seemingly like overnight, all of this stuff changed. I Mean, how, how does that kind of impact your view on risk and like, how you want to move forward in your life?

There's a retailer of urban apparel who offered over $400 million for the company when I owned 80% of it. And I literally was going through my Dropbox again. And I have the red lines where I ask for more money at the advice of my investors because again, $411 million is not that much of a success. When they paid $350 million, they want it to be worth a billion dollars. So I basically said no, but like, my life would be very different if I actually had like 200 plus million dollars in the bank. Like, I'm good, I'm not retired. But I'm also like, I, I made money. Like, you know, and I continue to make money, whatever. So again, back to the advice thing. I, I would say like, take the money. You may not get another acquisition opportunity. You know, there may be someone who's like, great, we'll buy you for $100 million while you own half the company. Like, go do the next thing. You know, you've got like so many lives in you. You don't have to like build a bazillion dollar business to be successful. You guys are so young. Part of me is just like, take the money.

There's a famous quote that's like, show me the incentives and I'll show you the outcome. And I think that that's really important to remember is like, the incentives aren't always aligned. When an investor's goal is to get that markup is to show their LPs. Hey, look, this business scaled so fast when we got into it versus the founders incentive is how do I keep this business alive? How do we sell it at a good valuation? And so I think that that's really interesting for you because I think your business is a case study of, yeah, the incentives were not aligned for the investors.

There's also an apparel business. Venture capital should be reserved for software. I'm sorry, you guys can build one thing and 100 million people use it. Like, I have to keep a warehouse full of clothes that cost a lot of money. It's just, it's not a venture for the most part. I don't think like retail is a venture scalable business which kind of goes back to, you know, if you want to start a business selling clothes, like, go figure out how to fund it yourself in the beginning if you can, or like take a loan or something. But you, you don't need investors for venture it's like, I think it's a little bit different. So you just have an opportunity to build something much bigger, much more quickly. And so there. Speed is important because there will be people who creep up and see your success and want to do the same thing.

And, like, how do you set goals and routines for yourself now?

I achieved more than I think ever thought I could and built something bigger than I ever thought I could. Could. And I. I kind of had goals, but I kind of just followed my nose to a certain extent today. It's like, my goals are really freedom, alignment with what I'm really good at, and not having a huge team of people that, like, keeps me in place and makes me, like a big manager because I'm really good at being nimble and making, like, a direct impact. I don't know, buy a house in London, you know, like, stop renting.

Figure out how to deal with three poodles who are like, a lot of work that I moved across the world and had, like, help with in LA and a boyfriend and housekeeper and stuff like that. So I think just like, I really like my life. Just keep leading the life that I have and keep making an impact and just deal with my shit.

I think you had said that your investors had made you invest $2 million of your own personal capital into the business, which is insane. Why did that happen and why did you agree?

Yeah, I mean, it ended up just kicking the can further down the road because the company could have just fallen apart then and I would have saved $2 million. But they were like, we already own 20% and we don't want to put a dime more in. And when you're trying to raise funding, which I was, you know, this was maybe like a year before Nasty Gal ended, and it's still going. It's like, own, owned by Boohoo now here in London or whatever. But he wouldn't put a dime more in. And when you have people that want to invest in the company, if your prior investor doesn't want to keep investing, even if it's just a tiny bit, it's a really bad signal. And so he was like, we own 20%. The only way I can convince the partnership to invest anything is we'll double whatever of your money you put back. And the idea was that it was going to motivate me to. To turn things around, but I just didn't know how to do that. And I already knew that. So it was kind of like a donation in a way to, like, okay.

A $2 million donation?

No, but it was like, I reinvested, but I had the CEO in place, and it was the only way I could get new investors in. Which we did do about a year before I stepped off the board and, you know, left the company. So I really resent it made me really resent.

Yeah.

The company. Instead of, like, motivate me to, like, double down on it and figure out what to do with it. Like, I had already kind of made clear that, like, I didn't want that job and I wouldn't have known what to do anyway. So I left it to the more experienced people. And, you know, what. What happened, happened. But, yeah, I mean, do I regret that? I don't know. You know? Yeah, sure. But whatever. Like, I'll always make money. It's just nice knowing that when you're smart and have experience and have relationships and, you know, if everything goes to zero, you can start over. It didn't go to zero for me. The. You know, but just, like, I know that if everything fell apart, like, I could still rebuild something really significant.

Wait, and where did love fit into all of this?

Yeah, I mean, I have a boyfriend. He's awesome. So we went to, like, we. I'd never met him before. We met in, like, a piazza in Venice for the first time, like, four days after I turned 40 a year ago and spent three weeks together. Then I came and stayed with him in London for a week, and I was like, oh, my God, I love this city. And that's when I really fell in love with London. We've been together for, like, five months or something. And he's English, but he speaks fluent Italian, which is very cool. So I'm like, can we just, like, move to Italy?

Yeah, you honestly should. Why not?

Right? Yeah, just, like, have a pool again.

And so, yeah, that's been, like, really fun and great. He's back in Sicily right now, actually.

Yeah. Because that's something I feel like our audience has been so interested in, is kind of advice around balancing career and relationships, both romantic, but also friends. Friendships.

I mean, I think in the end, you're just gonna disappoint people. Like, you're gonna be. If you're successful, you're just gonna be busy where at a certain point, you're not going to be able to, like, catch up with somebody. Even. Like, you might not have time for your best friends sometimes. And the right people are going to stick around and understand that, and the ones that don't are gonna, like, resent you. And there's a graceful way of being like I can't right now or I'm super heads down with something. But you know, it's kind of an easy way like should. People shouldn't take things personally when they they are excited for your success. Those people will be there when you come up for air after building a startup and raising money and running across the world and launching a podcast and killing it.

So, Sophia, I can't thank you enough for coming on the burnouts today. We've learned so much about incentive structures, how to build a business, what it looks like to scale, how to move on to the next chapter. And it was incredible to have you on. Thank you again.

Awesome to meet you guys. Congrats on everything.

How can I help you today? Hey, I need to talk about my loan.

No problem.

So I got the email. Sandy Spring bank is becoming Atlantic Union Bank. That's right. And will you still be your banker? Of course. More branches and ATMs.

Way more.

Still community driven, still live here, still give here. Mobile app. Easy.

Everything right at your fingertips.

And we're. What about my business?

Always here to help you reach your goals.

Sandy Spring bank is becoming Atlantic Union Bank. October 2025. Same bankers you love, with even more to offer. Every holiday shopper's got a list. But Ross shoppers, you've got a mission like a gift run that turns into a disco, snow globe, throw pillows and PJs for the whole family, dog included. At Ross, holiday magic isn't about spending more. It's about giving more for less. Ross, work your magic.

One iced coffee, 99 cents, please.

For real? No way. Mmm.

One iced coffee, 99cents, please. For real?

No way.

Mmm.

What a deal. Your new morning groove. Iced coffee from McDonald's, any size for just 99 cents till 11am Price and participation may vary. Cannot be combined with any other offer.