From brand savant to accidental entrepreneur

Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.

SOPHIA AMORUSO: I’ve heard “hire slow, fire fast,” but I’ve spent so much time with people upfront, and you only know what it’s like to work with them when you work with them.

JEFF BERMAN: Sophia Amoruso says “hire slow and fire fast” was common advice she got early and often when she was starting out as an entrepreneur. But it’s one of many corporate axioms she’s shirked along her scale journey. Sophia built the buzzy e-commerce brand Nasty Gal, and under her leadership, it reached nearly $100 million in annual sales. She managed to get there with absolutely no formal business training.

AMORUSO: Firing fast is kind of risky. Don’t fire too fast. You should give people opportunities to improve and point at, “This is your job description.” If that doesn’t work for you, that’s cool. Maybe we’re not aligned.

I think treating people with humanity is really important, and something that I used to be a lot more mercenary about and didn’t do. It’s something that’s really important to me now.

BERMAN: I’ve known Sophia Amoruso for more than a decade. Even in a world of other founders who lean toward the unconventional, she stands out as an unabashedly irreverent expert in branding. She is also the first to admit that she learned a lot of entrepreneurial lessons the hard way.

I’m Jeff Berman, your host.

Today, we’ll hear from Sophia about scale lessons from her first two ventures: The apparel brand Nasty Gal – which she started in her early twenties, and the Girlboss media empire that became her personal brand. But first, I wanted her to catch us up on what she’s been doing since exiting those businesses.

BERMAN: Sophia! Welcome to Masters of Scale.

AMORUSO: Thanks for having me.

BERMAN: It’s nice to see you.

AMORUSO: Yeah, it’s always nice to see you.

Copy LinkSophia Amoruso on her newest venture: Business Class

BERMAN: Right now you’ve got two major things going: Business Class and Trust Fund VC. Tell us about Business Class first, if you would.

AMORUSO: I started Business Class during COVID in 2020. I was like, “I want to go back to bootstrapping,” right? It wasn’t like, “Wow, I want to start a big business.” It was, “There are all these amazing tools at my disposal. I have so much to share. I’ve been through the gauntlet. I’ve been through experiences that very few entrepreneurs have, and I’ve seen the ups and the downs and the guts, and I just wanted to share that.”

So, I put together a course for entrepreneurs. It’s mostly bootstrapped entrepreneurs in the program. It’s a membership, and you get like eight hours of training from me where I go through everything from finding product-market fit to putting your brand together and naming your business, and all the weird kind of sideways that I did this in a way that other people didn’t.

And then some things that I’ve learned that are more traditional. Maybe you might learn this in business school, or I’ve learned from really amazing executives that I’ve had the pleasure of either employing, working with, or knowing along the way. So, it’s just like a treasure trove of knowledge, and then it’s also a community.

We have workshops and co-working sessions and ongoing content, and then probably at this point over 100 hours of video with workshops and interviews that’s exclusive to the community.

BERMAN: Part of what’s so interesting about this is not only does it build on the crazy incredible experiences that you’ve had, relationships you’ve built, and knowledge that you have, but it’s a way to scale yourself, right? Because you can’t do this in one-on-ones. It would take 29 hours a day.

AMORUSO: I’ve done a little bit of one-on-one consulting, which is actually really fun. But the one-on-one stuff that I do is with the founders that I invest in. And then the way I can scale myself, or be a master of scale, or scale my mastery, is through being able to distribute what it is that I know. I do that for free on social platforms, and I have a newsletter with like 140,000 subscribers. So, I do it in all the ways that I can.

But it’s like the more we can share what it is that we’ve learned, especially the hard stuff that’s been really painful, and put it to use. It just feels really good to do something with it beyond internalizing it and trying to apply it over and over again for ourselves, but for other people to see around the corners because of what we’ve been through.

BERMAN: Yeah, and the free part is sort of the Gary Vaynerchuk “give, give, give, ask” of it, right? It’s like, “I’m gonna keep giving you, and at some point, I’m gonna ask or offer you something more. And if you want to go deeper and get more…”

AMORUSO: Like jab, jab, jab, right hook, or whatever. Or “know, trust.” So it’s like, “Oh, I’m aware of who you are. Oh, wow, I like you and your personality.” And then trust, it’s like, “Oh, I trust you and what you have to offer and what you’re selling, and I’m gonna go through the bottom of the funnel.”

Copy LinkHow Sophia became an accidental entrepreneur

BERMAN: And this builds on two extraordinary entrepreneurial experiences. So, I know you’ve talked a lot about both Nasty Gal and Girlboss in other places, but will you tell us how you got started as an entrepreneur and where this journey began?

AMORUSO: Well, I didn’t mean to be an entrepreneur. I guess I’m an accidental entrepreneur. I was 22 years old, and I didn’t consider myself ambitious. I was just really bad at working for other people. I was pretty much unemployable. No one really told me what a career even was. Like, were I to pursue it, I would not have known where to start.

So, my way to evade working was to start an eBay store selling vintage clothing, right? At that time, eBay was the marketplace. Amazon had book reselling, which the first stuff I sold online was actually on Amazon as a book reseller, but I was selling stolen books. I was like 17. I paid my rent, and it was great. I’m not proud of it, but it happened a very long time ago because I was like, “I’m eff capitalism,” right? And now it’s in my title. I’m a venture capitalist.

But I started selling vintage clothing on eBay. I followed my nose and I did a better job each week, and sales went up. It wasn’t about making money. It was just exciting. Like, “Wow, what can I pull off here?” I didn’t think I could do any of this. I didn’t think this was possible. I still didn’t consider myself ambitious, but it was really fun curating stuff, styling it, photographing it, writing descriptions for it, and seeing how much people liked it. Having that positive feedback loop was so motivating.

BERMAN: And at the same time, there were thousands of people selling on eBay who weren’t creating a brand.

AMORUSO: I think I’ve just always had an irreverent point of view. I came out of stripping and stealing and wasn’t trying again. I didn’t really care. How I operate just naturally cuts through the noise.

As someone who grew up really angry at authority and is able to pull from asymmetric references and bring them together and combine things in the same way that someone who’s writing a song does, right? Everything’s referential. Almost nothing’s new, but borrowed from a bunch of different influences. I called it Nasty Gal, which was after this amazing album by Betty Davis, an amazing 70s funk singer who was married to Miles Davis, and allegedly too wild for him. Her lyrics are just awesome.

I was like, “Okay, hippy-dippy whatever, I’m gonna call it Nasty Gal Vintage.” It was just naturally kind of edgy. A brand is so many things. Like, you can’t pinpoint what it is. It’s the name, it’s the spirit, it’s what you curate, how those things blend together. It’s the models you cast, the way you style it, the quality of the photography, the way you describe something. It’s the copy on your website, the design of the website, the user experience on the website. What happens when you write customer service.

The brand lives within the organization. It’s how people operate. It’s the things that they live by, and that has to live out in every pore of every component of your business. That is also your brand. All of those things matter to me. The way I slapped a label on a shipping box when I was still shipping stuff was important to me. The little handwritten thing people got in the very beginning, that was whatever, XOXO Nasty Gal or something, was important to me. I had stickers that said, “I’m a Nasty Gal.” I eventually created something with Nasty Gal and eventually with Girlboss where the name of my business was put at the end of a statement where people said, “I’m a Nasty Gal. I’m a Girlboss.”

I think the best and highest thing you can do with a brand is have somebody identify with it, have their identity tied to it, and have it give people a sense of confidence or see a future for themselves that they didn’t otherwise. That’s peak brand, that’s what I’m most proud of.

Copy LinkScaling with intention

BERMAN: It’s literally building identity brands, but you’ve done it more than once, which is a stunning thing. So when you went from Nasty Gal to Girlboss, were there lessons from Nasty Gal that you immediately applied to Girlboss that you kind of supercharged that journey?

AMORUSO: Yeah, absolutely. Nasty Gal, I was totally at a disadvantage. I had never worked in an office before. Every office I’ve worked in, my name has been on the lease of, I had never managed anybody. I didn’t know what leadership was, which are totally different things.

After 10 years at Nasty Gal, Girlboss had become this whole thing. It was this book that spent 18 weeks on the New York Times bestseller list, sold half a million copies, became a Netflix series, and it became part of the zeitgeist in a way I could never have predicted. Even though Nasty Gal was doing over $100 million in revenue, the noise of Girlboss was even louder.

When I started Girlboss, I wanted to be really deliberate. I didn’t want to start another business on accident because when you start something on accident or without intention, it’s serendipitous, and, oh, accidental entrepreneur. It doesn’t scale.

Having intention at the beginning, having a foundation for how the company operates, making what you think is implicit explicit for people as early as you can, and reiterating it.

BERMAN: Make the implicit explicit. Can you give us an example of that?

AMORUSO: At Nasty Gal, the brand just lived in me, right? As it exploded, I had people buying and curating. There was a person who bought knits and dresses and wovens and planners, and a creative director and photographers, and people styling stuff, hair and makeup people, people doing casting and locations, a huge creative team in an in-house studio.

All of those people were trying to decode what the brand was. It was very late by the time we had this thing that was like, “This is the brand book. This is how you use the logo. This is the voice of the brand. It’s this, not that. It’s irreverent, but it’s not snarky. It’s warm, but it’s not saccharine,” right? All of these things where you can point at them.

When somebody writes some copy, or when someone takes a photo, or when something is out there that represents the brand, it’s not “Oh, Sophia wouldn’t like this,” or “Oh, it’s my opinion. I think that’s ugly,” right? It’s like, here’s what it is. Because at a certain point, people were just kind of trying to predict what it was, and their egos get attached to it. They’re like, “Oh, but that’s not cool.”

There were conversations in rooms without me, where I would hear eventually that people were saying things like, “Oh, Sophia wouldn’t like that,” which is like, “Oh wow. That’s cool that they care, but also, maybe they’re wrong.” The people you’re telling that to feel bad. They’re like, “Oh, I don’t get it.” They’re telling me I’m not cool, or that’s not on brand.

That’s the worst: “That’s not on brand.” If that is debatable — what’s on-brand or off-brand — then it’s just gonna be a cluster of people disagreeing. And the haves and have-nots of creative or culture or whatever it is that you’re trying to create.

Something objective outside of you that says, “Look, this is what it is. We can all point to this North Star as our source of truth.”

Copy LinkWhat Liquid Death gets right about branding

BERMAN: One of the contradictions of the current world is it’s never been easier to build a brand because the barriers are down, right? I mean fragmentation of media, etc. And at the same time, it’s never been harder because it’s never been noisier. I mean, we are bombarded with impressions second by second, effectively. Who’s doing a good job of this right now? Who’s breaking through in a way by taking an outsider perspective, an oblique angle, and creating a really meaningful brand in the world?

AMORUSO: I think Liquid Death is a great example. So, I invested in Liquid Death when it was worth like $50 million, and they’re over a billion now.

BERMAN: And Mike Cessario is a phenomenal CEO.

AMORUSO: Yeah, he came out of the punk hardcore scene, right? He was a creative director, I think, at an advertising agency or something.

BERMAN: Yeah, we had him on recently.

AMORUSO: So he’s bringing a totally different perspective and has the audacity to make water tough. Again, it’s like peak brand. People have Liquid Death art tattooed on their bodies.

Copy LinkThe power of brand recognition

BERMAN: I was part of the founding team of Together, the women’s sports and culture company with Sue Bird, Alex Morgan, Chloe Kim, and Simone Manuel. We said from the beginning that we will know that we have a brand when someone tattoos our logo on their body, which has now happened multiple times. It’s an incredible experience to see that happen.

What are the other metrics that you look for, particularly now as we evolve into the investor life you have, where you go, “That’s a brand that’s breaking through or is going to break through”? What are the data points you’re looking for that tell you that? Or is that gut for you?

AMORUSO: That’s a really good question. It’s pretty gut for me. One thing that I always considered when I bought something for Nasty Gal was, “Is the product inherently shareable?” You get one millisecond when someone’s scrolling for something; they may or may not read the description. Every piece of real estate that you have to catch someone’s attention is important.

If you can see the silhouette of the product in more of a Rorschach — is that how you say it? — kind of way, if the brand or the logo or some copy or something about it is so strong that it imprints on your brain like a stamp, it’s gonna last. That can be marketing, a logo, the product, and it kind of all has to work together. When I see that, I really understand the power of a brand.

I invest in B2B software. So, the thing that I’m able to help these companies with is — they’re not inherently brands, right? One of the companies I invested in is called Toothio, and they’re a dental labor marketplace, right? I’m investing in companies through Trust Fund that are creating products that I wish I had when I was rubbing two sticks together. There was no Dropbox when I started, right? There were no project management collaboration tools, AI web scraping stuff, social media automation, or really social media. I was adding people manually on MySpace in the beginning.

So, having built a company — a consumer business, yes — but a company on the internet, not having any of these things that have emerged to make it easier to start a business or to become an entrepreneur. The dental labor marketplace, it’s not a workplace tool, but dental hygienists are able to work for themselves and set their schedules for the first time ever because of a platform like that. That’s the power that eBay gave me, and I understand it more than almost anybody.

Also, those tools that I didn’t have now exist, and they’re continuing to emerge. I know which ones entrepreneurs really need, or freelancers, or I think the word “entrepreneur” means something very broad, right? You talk to a lot of people who’ve raised venture capital or whatever, and it’s like, someone doing Postmates is working for themselves. You can do a better job than other people. Doesn’t matter what you’re doing, you can do a better job than other people.

You can take what you learn, even if it’s in a gig marketplace, and you can leave and do your own thing. But all of these things give people an opportunity to move faster — a framework to build a business.

BERMAN: Sophia, I mean, first of all, I’m not going to say “double-click.” I will not say “double-click,” but I do want to pause for a moment on — there’s this popularized version of an entrepreneur who bootstraps a company and then raises venture, and whatever. The vast, vast majority — I mean like 18 million new businesses started in this country over the last four years — are not venture-backed, and there’s no aspiration for them to be venture-backed, and there shouldn’t be, and they shouldn’t be venture-backed.

AMORUSO: And they shouldn’t.

BERMAN: And they shouldn’t be venture backed. That’s exactly right. But they still need software. They still need products and services to help them run their business. Part of what I hear you saying is that’s a marketplace you understand because you were and you are doing that.

AMORUSO: The density that I had, the little amount of information I had, and the complexity I had to decode without that software, and then how far I got. Understanding what that complexity looks like once you have hundreds of employees is kind of an unlikely thing.

BERMAN: Still ahead, we hear how Sophia has translated the scale lessons she learned as a founder into her new chapter as a venture fund operator. Plus, she answers your questions. Stay with us.

[AD BREAK]

BERMAN: Welcome back to Masters of Scale. You can find this interview and more on our YouTube channel.

Copy LinkWhy Sophia Amoruso launched trust fund and became a VC

BERMAN: So tell us about Trust Fund. First of all, why become a VC? Why launch your own fund? And then, what is Trust Fund?

AMORUSO: I had done a lot of angel investing with my money and had access to deals by the sheer nature of having raised venture capital, knowing other VCs, knowing angel investors, knowing entrepreneurs who were starting things, knowing entrepreneurs who were referring me to their friends who were starting interesting things, and those people having heard of me and seen my story, being like, “Holy crap, her expertise, whether it’s through building a business or knowing what not to do building a business now, or especially building brands, could be really valuable to me.”

So, founders wanted to work with me. They wanted me to invest. I was getting into really great deals. I invested in Kindbody, Liquid Death, Public.com, Eight Sleep, Therabody, and some really awesome brands. The founders, I think, generally found me helpful and kept getting those introductions.

There’s a purity to just using what I have and sharing it. When someone asks a question, and I run my mouth, and it’s helpful, and it changes something for them, there’s no better feeling. If that’s the business I get to have, and I have the access, the tenacity, and the track record as an angel, and I can make a material impact, and I can amplify the brands, I can work behind the scenes with the founders, and I can fundraise — it’s like there’s this whole combination of things, this stack advantage that I have, that lends itself to building a fund and having a different point of view.

No, I’m not in finance, but that’s not the thing I’m going to compete and win on. As a fund manager, I can learn a lot of those things, and I have so many fund managers around me and can hire people who’ve done this stuff to augment what I don’t know. The information is out there. Everything you need is out there.

I don’t want to shortchange experience because a fund is not angel investing, right? It’s a portfolio, portfolio construction, and recycling, stuff I didn’t know about as an angel investor. But I like learning, and I like doing things I’m not qualified to do. But guess what — nobody is. That’s the catch.

BERMAN: Right, it’s one of the… I mean, you referenced MySpace. One of the great lessons from my career was Chris DeWolfe, our mutual friend, who was the CEO of MySpace. He walked into my office the day after Google bought YouTube, and I ended up overseeing the launch of MySpace’s video platform. When he put me in charge of it, I was like, “Chris, I don’t know what I’m doing.” And he sort of stage-whispered to me, “No one does.”

The companies you’re talking about are selling to solopreneurs, to small business owners. Those are really hard people to reach. How do you reach them? Brand matters, right?

AMORUSO: Even though I’m not investing in consumer product businesses, my network there is valuable. I can just shoot off a blurb to a bunch of CEOs of mid-size and larger consumer beauty, fashion, whatever businesses, and they’ll take the call. They’re converting — my portfolio companies are making money because of a 30-second email I shot off. They earned it.

BERMAN: And that’s a value that a lot of VCs promise, and very few are actually capable of delivering on. I’m curious, is that part of why you called it Trust Fund? I mean, because you’re not a trust fund kid, but obviously, you’re someone who’s built enormous trust with so many people over the course of your career. So, what’s the rationale for the branding?

AMORUSO: It’s just a good name. That’s it. Rich kids want to wear the bucket hat. Kids that didn’t grow up with money think it’s funny to wear a hat that says Trust Fund on it. Kids in the Hamptons are wearing hats that say Trust Fund. It’s funny, and it cuts through the noise. I could be like, “Yeah, it’s built on trust, and I never had a trust fund, and I want my founders to build.” I don’t have kids, so I don’t even know who I’m making a trust fund for. It was just like, “This is funny.”

You know when you go to the Upfront Summit, and see these VCs I’ve known forever who are still at their firms or spun out their own firms, and they’re like, “Oh, why didn’t I think of that?” I’m like, “Yeah, I don’t know. It’s just fun. It’s just brand.”

BERMAN: Yeah, it feels like they all work for something where it’s “animal name plus tree” or “animal name plus field,” and it’s like endless…

AMORUSO: It’s like endless copywriting fun. I have a pop-up on the Trust Fund website to collect email addresses, and it says, “We’re making a racket,” but it’s like R-A-C-Q-U-E-T, and there’s a Ralph Lauren ad from the ’80s of some waspy guys holding tennis rackets. That’s very funny to me. You don’t forget that.

Copy LinkListener questions: Is the Creator Economy going anywhere?

BERMAN: Okay, I’m going to my phone only to pull up our listener questions, or audience questions.

The first question came in on LinkedIn today. Curious about where you think we are in what has been called the “creator economy.” Are we sort of post-creator economy? Does this have a long way to go? How are you looking at that market?

AMORUSO: I think the creator economy is not going anywhere. People want to learn from people. They want to hear from people. Brands are trying to be creators; they’re hiring creators. People trust people, right? Somebody’s individual experience is more valuable than a textbook or some crowdsourced something-or-other on a blog. Who knows who wrote it, and if they just researched something and put it out, and we’re supposed to take that seriously? People will be held more accountable for what they have to offer, and we’re moving away from just dumb entertainment and people having to provide value.

BERMAN: Nike’s had some well-publicized troubles the last couple of years, and I think some of it is because athletes can go do things on their own, right? Even Together, the company I referenced earlier with Alex Morgan, Sue Bird, Simone Manuel, and Chloe Kim, like that “Everyone Watches Women’s Sports” T-shirt that was everywhere — that’s theirs, not Nike.

Copy LinkBuilding a culture that amplifies young voices

If you’re talking to the CMO of Nike or the head of product for Nike, what are you saying to them about how to engage with this new world that is foreign to how they grew up?

AMORUSO: Hire young people and listen to them. They know better. Even when I was in my 30s at Nasty Gal, we hired kids who were like 20 years old, and they’re bringing a different perspective. You can’t see that stuff from where you sit on a corporate board or having built your own organization. Just embrace the periphery and embrace change.

Even I was kind of late when the influencer thing started happening. As someone who worked extremely hard to build my business, I was like, “No, we are not paying people to put clothes on. Like, these people aren’t doing — they’ve never done anything, and we’re… What?” Fundamentally, I was grumpy because I was like, “No, you should have to work hard for stuff.” But that’s not how it works. You can’t white-knuckle change away.

BERMAN: And yet at so many of these companies, you hire that really sharp, ambitious, creative 22-year-old, and then you don’t have a culture in which their voice can actually influence the decisions.

AMORUSO: That’s all about culture. You can put it on the wall, but if you don’t live it, and if everybody in your organization doesn’t actually live it out, and it doesn’t start at the top and make its way all the way down and then back up again, and you’re not listening, you’re going to miss out on a lot.

I let that happen in my company, where people were saying that we have a no-asshole policy or that people’s opinions are considered and valued, and they’re just delegating to them, and they’re not really letting them contribute. The consequence is that maybe you’re going to get left in the past, or maybe you’re not going to embrace new trends, or maybe you’re not going to hear new ideas from new people who are bringing in new ideas or young people who are closer to culture.

But also, people are going to hate their jobs. Outside of how that can hurt your business from a marketing perspective, nobody’s going to want to show up because they don’t feel heard. Just build a good culture, and then you can listen to people. I don’t even know if it’s a marketing problem.

Copy LinkThe impetus to go to London

BERMAN: As we sit here today, a few days away from you going to London for a few months — why?

AMORUSO: Because I turned 40, and I’m single, and I don’t have kids, I realized I can be anywhere. After almost 15 years of being in businesses I built with teams and offices I had to show up to, and be kind of rah-rah the world has changed. You can work from anywhere.

I don’t want to be a nomad per se, but I’ve been in LA for 14 years, and I’ve been in my house for 10 years. I bought my house when I was 28, and I don’t want to maintain as much. I don’t want as much. I got rid of 80% of my closet. My closet was the size of a bedroom. I’m not missing anything. I’m not wondering where anything went. I don’t remember what I put in bags. I’m going to have some kind of a clothing sale.

The world has put me in circumstances I have to find my way out of, and I’m like, “An apartment in Notting Hill is not that uncomfortable,” right? Like, in the grand scheme of things. But I just want to try different things on for size and see what inspiration or perspective bounces back at me. I could change my mind. That’s the beauty of it.

Copy Link“I don’t have it figured out”

What do you do going forward to help take care of your mental health on the incredibly complex, demanding, relentless journey that you’re on?

AMORUSO: I don’t think I do a very good job. I think the word “masters” is in the title of this podcast. I’m just gonna refresh everybody and be like, “I don’t have it figured out.” I have ADD. I’m chaotic. I don’t have a morning routine. I got really frustrated yesterday and overwhelmed, and I just laid down for half an hour in the middle of the day. I’m like, “What is wrong with you?” I’m late to yoga. I don’t have a solution.

I’m really grateful for what I have. I have great friends. I’m not uncomfortable asking for help, advice, or reaching out to people. I don’t suffer in silence. As masochistic as it is, and unsustainable as it is sometimes, staying busy is not the worst thing. My answer is, I don’t have it solved.

BERMAN: Well, and yet I’m hearing gratitude. I’m hearing rest. I’m hearing moto yoga, and I’m hearing connecting with friends.

AMORUSO: Okay, I guess that’s a normal human answer. It’s not like I take ice baths and I wake up at 7 a.m., and I gratitude journal every morning, and I don’t deviate because you hear that stuff on podcasts and it just makes you feel really crappy about yourself.

BERMAN: Right, I wake up at 4 AM.

AMORUSO: Yeah. So my answer to everybody listening is, you’ve probably got it together better than I do, and the whole “Habits of Highly Successful People” thing doesn’t always correlate with people who are considered highly successful.

BERMAN: You were incredibly generous to come spend the time with us. Thank you for being here.

AMORUSO: Thank you. Such a treat.

BERMAN: Sophia calls herself an accidental entrepreneur. And she was. But since starting Nasty Gal in her early twenties, she’s become a veteran, making decisions with the intention and humility of the very best business people you could ever hope to meet. She’s sharing those lessons with all of us in her new venture, Business Class. Learn more about her online classes and community at Business Class.co.

I’m Jeff Berman, thanks for listening.