From Gimlet Media, this is Without Fail, I’m your host Alex Blumberg. This is the show where I talk with entrepreneurs, artists, athletes, visionaries of all kinds -- about their successes… and their failures, and what they learned from both.

When my co-founder Matt and I started Gimlet, four years ago, I was coming into it in a way that I think happens with a lot of founders. I was a product person. I made the product that this company was going to be selling. I made podcasts. For most of my life up until becoming the CEO of Gimlet, I had been a nonprofit journalist working in public radio. And early on that was fine, that was actually good for us. Because I knew how to make the thing we were making and I knew how to make it pretty well. It felt like the next phase of my career.  

But one of the weird things about going from the maker to the person running the company is that the skills that got you there don’t necessarily seem like they apply anymore. As the company grew and we hired more people and we had investors come on, I noticed I was having this feeling that I hadn’t had for a long time. A feeling like, I don’t know how to do this job. 

And you know it wasn’t just a thing I was feeling. It was something that everybody else was noticing too.

Matt and I just had 360s done about us. It’s this thing where you go and hire a company and they go and talk to lots of people all around you. They talk to the people who work for you, people on the board, they talk to your friends and family and they ask them all these questions about when are you at your best, when you’re at your worst, what are the things you need to work on.

Just imagine the most naked, most unflattering photograph of yourself that you ever could. That’s what a 360 is. Every single blemish, every single fault is highlighted in bold relief. And this one was no different. 

There’s a bunch of nice things. But there’s a lot of things that I’m not doing very well. 

Quoting from my 360, “communication, organization, prioritization, blind optimism.” And a biggie, “taking my seat as CEO.” Being comfortable being the person who is making lots and lots of decisions. And they have all these quotes and like they are like ask examples of sort of where did you see Alex most not taking his seat as CEO and I mean man, there’s pages, there’s literally pages, I’m scrolling through pages of all these examples of where I’m not being decisive enough, where I’m not being clear enough in my communication, where I’m not actually saying what the people who work for me need to hear from me. Where I’m not being a leader.

I know a lot of CEOS must go through this. Especially CEOs who started like I did -- almost accidentally. Like they were just good at this one thing and then that thing took off and now they are the head of that company that does that thing. And that is why I’m very excited about the conversation that I’m about to share with you today. A conversation with Sophia Amoruso.

Three years ago, Sophia Amoruso was on the cover of Forbes as one of America's richest self-made women. She’d started a company called Nasty Gal, when she was just 22 years old. And grew it into an online women’s fashion brand that was valued at 350 million dollars. She wrote a best-selling autobiography, Girlboss. She gave speeches to sold out auditoriums. Netflix made a show based on her book. But then, in November of 2016, it all fell apart, very publicly and very spectacularly. 

I wanted to talk to Sophia because she like me was a first time founder who never really imagined herself as an entrepreneur, and then all of a sudden there she was, and she had to learn everything on the job. 

I had a very candid and very illuminating conversation with Sophia. About what happened during the 10 years that she found herself at the head of this company and what she learned from everything that went down. 

And I should say before we begin, this episode has some strong language...so you might not want to listen with kids around.

Sophia and I started our conversation at the beginning, before she was on the cover of Forbes, or a best-selling author. Back when she was a 22 year-old college drop out, who’d managed to land a job with health insurance as a security guard at a local art school: 

SOPHIA: My title was Campus Safety host. My job was to sign in people who didn't have a student ID. And for those people looking for admissions, to tell them it was on the second floor and to sit behind a computer I guess I mean I wasn't supposed to be on the Internet but there was like a secret way to hack into it if you just pushed the mouse like a thousand times like the computer would go nuts and you could get on I was like you like bust through the firewall. Spent a lot of time on MySpace this was 2006.

ALEX: And on Myspace, Sophia kept getting friend requests from eBay stores. People who’d set up shops on eBay selling vintage clothing. Mama Stone Vintage wants to be your friend. Indiecult Vintage wants to be your friend. Sophia would follow the link on these friend requests, and see how occasionally, huge bidding wars would break out over some item, and the seller, these stores, could end up making a lot of money. Sophia thought, I have a good sense of style, I love to shop at vintage stores, I can start my own store on eBay. So she did. She decided to call that store Nasty Gal. 

SOPHIA: I never for a moment thought I was starting a company. I was just like let me see if I can like not leave the house and sell some stuff and make a few bucks. And so yeah, I started with some stuff that I owned I went to a thrift store bought some stuff that I thought might be cool you know styled it on like a random friend took some you know probably shitty photos and put it up on eBay to see what would happen. And then some stuff sold and some stuff didn't. So I just learned and tweaked and then you know spent time really trolling my competitors and seeing what was working for them and putting my own spin on it. But going in sourcing that vintage. Oh, a wool cape with a bow tie or you know a 60s baby-doll mini dress with like a ruffled bib or whatever the fuck the language was that was you know trendy at the time. 

Alex: What was the first thing, in the early days, what was the first thing you remember that did pretty well.

Sophia: There was a dress; it was a wool Lily Ann dress and I didn't know what Lily Ann was but it was like a nice 1960s shift dress finely knit like heavy wool and it was sleeved 

Alex: And then you notice that like the bidding was going like just like there was a lot of interest in it?

Sophia: Yeah, the auction price just rose and rose. Yeah eBay is so interesting because you know as a seller you're sitting there and it notifies you when there's another bid like oh my god it's twenty five dollars higher. Oh my God it's 50. Like people are duking it out. So just watching people fighting over it. And then I remember I was drinking I don't know like Tecate, like canned Tecate in LA with some goofball friends of mine and I had like I think a Blackberry Pearl at the time which was like oh my god I can look at the Internet on my phone and my auction closed and I made like 2500 bucks in a week and I was like What. It's just it's just like felt like I was like rich.

Alex: Describe that feeling.

Sophia: I guess it was like I'm on to something. Everything else I did ever was just so intolerable. Like every job I had every class I took I was like I can't apply this right now. Why am I here. I was really impatient and I had something where each day I learn something new, each day I could see the proof that I was you know when I when I worked harder at something or I thought more about something or what I'd just done the success or failure of that had you know informed like a better choice and how everyday it was it was you know building on itself. It was just like so gratifying it's it's like no other feeling.

Alex: What is your identity at this point?

Sophia: I don't know if I had much of an identity at this point like I was behind Nasty Gal and Nasty Gal was cool and was gaining traction. Nobody like knew who I was and I didn't care. it was like all day it was just all I did for years 

Alex: At what point in these early days did you realize like things were going well here. I'm I'm on to something

Sophia: I eventually saved a million dollars in cash in a bank account. It was all cash like I didn't have a credit card. I didn't have debt. I have a screenshot of the company's account it has like nine hundred ninety five thousand dollars. And I was at the top of the pack in that vintage category. People were bidding them up to the highest of the highest I could buy something for 20 bucks and sell it for 400.

My average auction closing price was 150 dollars and I usually spent no more than like 15 20 dollars on on on something. So it was just like it was like free cash. It was literally alchemizing something through...it was just like perceived value. It's like I'm literally taking something off a floor putting it on a person styling it into something modern and it becomes valuable.

Alex:  What happens next. Eventually you move off of eBay though?

Sophia: Yeah I mean it was a place where I was like sending a lot of traffic from MySpace marketing things and then you know at the bottom of my listing there's like for other items from other sellers and I was like Why am I giving this away? 

Alex: Why am I sending all of this traffic to other sellers to eBay why don't I just send it to myself since I have the audience on MySpace I have all the friends on MySpace. I'm the one who's built this audience that should just be coming to me. So you build your site. What was your state of mind?

Sophia: Directing your traffic to someplace completely new is a really big risk. 

Sophia: But I didn't realize that I had editors shopping with me like L.A. fashion editors and at the time DailyCandy was a thing which is like a massive email list Who What Wear you know the editors founders Who What Wear were shopping and so when they caught wind that I was about to launch something they sent out like dedicated emails to their audiences about nasty gal launching a Web site before it ever happened and there's just tons of tons and tons of interest and and that's I kind of knew it would do well. I had no idea it would sell out so fast.

The Web site sold out like oh it launched it and it sold out overnight. I was like alright, alright Kelly Rippa's stylist was calling it like. Do you have another one of that vintage jacket in an extra small. And I'm was like no, it's one of a kind but cool Kelly Rippa's stylist is L.A. seemed like oh my god LA, What? Someone who knows a celebrity.

Alex: Kelly Rippa’s stylist, that’s a real..lot of people see Kelly Rippa!

Sophia: Yeah, it’s pretty exciting. Yeah. 

Alex: So that basically sort of launched you into the next phase. You've gone from essentially a business where you can do it by yourself it's like you can operate it and you can outsource where you need. But like it's just you. How did you go from that to at a certain point you had how many employees.

Sophia: Around 300

Alex: How do we get from you to 300.

Sophia: So long story short I just kept doing that I kept buying stuff that people liked and stopped selling things that people didn't like and spent less money than I made and kept reinvesting in the business. And so I mean my first year on eBay I think I did seventy five thousand dollars which is like I mean again, I wasn't making that as a salary it was the businesses money. And then second year was 250 grand.

Sophia: And the year after that it was one point one million than it was six and a half million than it was 28 million and it was really just like there was so much demand there was so little like e-commerce at the time there was nothing for for this girl with any kind of personality, this is 2007, 2008. And I just hired a few more people to ship stuff than you hire a receiving person then you hire a dedicated customer care person you break out all of the functions of the business and hire people who are not generalists but specialists and— 

Alex: How are you feeling about it? That's pretty that's a pretty big upgrade from like you know living living in a closet in Sacramento.

Sophia: Totally

Alex: And pretty quickly.

Sophia: Totally. I had a balcony. It was like I furnished it with CB2 and it was like I had a parking space. And I had bought myself a Nissan Murano. I was living it up, right? Like I could eat as many burritos as I wanted. And I move the company to L.A. in late 2010. And I rented a house with a backyard and a hot tub and it was like a two bedroom house but it's like an actual house in Los Villas and I think I paid maybe 2800 dollars a month, which was a lot. And I wasn't sure if I could afford it. And I felt like I would like grow into affording it.

And I really do think that making commitments before you know how to keep them is how you manifest things. It's also like how you end up like fucking up, but it's like you won't step into that opportunity or being able sometimes to afford those things as irresponsible as it may seem without like actually committing to it. And so so yeah I was living in L.A. and and it was around, it was at the 28 million dollar mark in 2012 when investors venture capitalists started calling me.

And I had no idea how my life would change when when venture capitalists came came in to play.

After the break, how her life did change when venture capitalists came in to play. That’s coming up after these words from our sponsors. 

(AD)

Welcome back to Without Fail. In 2012, Sophia’s company, Nasty Gal was doing really well. It had over 28 million in revenue. A loyal customer base. It looked like she was just going to keep growing. That all changed when investors started showing an interest - calling Sophia, wanting to talk about investing in her company

Alex: And what were you saying about this were you intrigued, were you like I don't know what were you thinking around the first call.

Sophia: Well I had a profitable business. And they like wanted and they were like How did this freak bootstrapped a business 30 million dollars profitably you know. We want in. I didn't need to raise venture capital. And then I met Danny Rimer at Index Ventures who's I think one of the founders and he called me and he said I get it you have a community. And that was when I said OK this guy gets it.

Alex: Your life sounds pretty good. Why did you why did you want to take investment? You're you're making 28 million dollars, you're making profits. How much money do you have in the bank?

Sophia: Maybe like a million bucks or something I mean me personally I don't know. I mean I mean maybe like 15 grand or you know I had a salary and I could pay my rent. I had no debt. No you know I didn't I didn't have a lot to pay for other than other than that I didn't have expensive taste. Right.

Alex: But even though even though the revenue from the business was 28 million dollars you're still not it's not like you were you personally were bringing home a ton of money.

Sophia: I was not a millionaire, no.  Nothing I could. Nothing memorable before investors came in.

Alex: Got it. So was that partly what it was like this was oh this can be a way for me to get paid back for a lot of this hard work that I've put into building this brand to this point?

Sophia: For me it was like these guys valued the company at 350 million dollars post money, which meant I sold like I don't know what 15 percent of my company. And I had two seats on the board and Danny had one and that was that. And the company had you know they had put 40 million dollars in and I sold a little bit of secondary which means like I personally took a little money off the table. The majority of that investment went into the business. But for me it was like an amazing cushion to have and be like wow like I just busted my ass for six years and now there's like something to show show for it because I never took a dollar out of the business and that was that was the life changing moment. Like I became a millionaire.

Alex: Right.

Sophia: When you're like twenty eight or 27 or however old I was I mean that's weird. It's really weird

Alex: What was weird about it?

Sophia: I don't know. Just being able to afford stuff and then like not knowing like as soon as that happened I could like afford things and like everything was expensive so I didn't know how expensive really expensive was. I have no gauge for like whether I'm just being duped or if like that's how much things actually cost. I paid off my mom's mortgage. Yeah I did that was the first thing I did.

Alex: That's that's gotta feel good.

Sophia: Yeah it felt really good. I bought a Porsche.

Alex: Which also has to feel good.

Sophia: The Porsche felt good.

Alex: What felt better?

Sophia: the Nissan

Alex: No paying off your mom’s mortgage or buying the Porsche.

Sophia: I mean paying off my mom's mortgage but as far as the Porsche goes the fucking Nissan was like you will know. You won't ever experience what it's like to like put down 10 grand for a car. I mean I saved and saved and saved to put down ten grand on a used car and have like a low payment like that was the I'll never experience that again.

Alex: That felt better than the Porsche.

Sophia: Oh my god. Yeah. So. 

Alex: OK so. So you take on investor money. And then what happens?

Sophia: Oh my God. I hired C level people. We like licked our finger put it in the air and we're like 28 million. Well next year we'll do 128 million just round it up by a hundred million dollars. And I trusted a lot of people. I was very naive and that's not to like not take responsibility for the trajectory that Nasty Gal went on at that point but we wanted to grow by 100 million dollars. And so we hired 100 people in a year and it became full on the Tower of Babel and we did grow. You know we didn't get to a hundred million dollars in a year I think we got to 60 and then we got to 80 and then we got to 100 and over 100 but that didn't happen 

Alex: But that didn’t happen in one year.

Sophia: It didn’t happen in a year.

Alex: Talk about that. Because I feel like that's a thing that we've also struggled with sometimes is to try to figure out like you have to sort of forecast what you're going to grow. You have investors who are sort of expecting growth like our investors are very like... I've heard horror stories about like where's my growth you know and people are pounding the table and it's definitely not like that with us. But like we have you understand that when you take an investment like you're not going to be you know a simple business anymore you're going to be a growing business like that’s the deal.

Sophia: You work for the board. 

Alex: Yeah.

Sophia: We pulled number out of the sky and we had no history to base it on. It was just like a one point one six and a half 28. Like ok I guess we’ll quadruple that number. And I don't know but we didn't have real like merchandising systems to base like forecasts off of it was pretty basic kind of back end of the business that we had at that point and was very much just like pulled out of the sky. Going from a mom and pop shop really at that scale is and converting that kind of a business that was venture growth without venture capital and the kind of infrastructure and reporting and expectations and way of working that comes with investors and real executives and all these things that just all happened so quickly. The learning curve became really really high for me and I had to trust the people around me and the people that I hired who had experience more experience than in their careers than I had been alive. And and and it grew and it kept growing and it wasn't till several years later where it started to kind of it started to level out a little bit which was probably in late 2014.

Alex: You wrote in your book I didn't plan to start a business. I was 22 and then you said you're looking for a way to pay my rent and buy my Starbucks chai and then you say, “had someone shown me the future of where Nasty Gal would be in 2014. I would have gasped in revulsion.”

Sophia: Oh wow. I don't remember writing that. That's what...I hope my team didn't read that well.

Alex: Yeah.

Sophia: I thought business people were like suits and I thought like the word CEO was just like I thought capitalism was like putrid.

Sophia: I wasn't in it for the money. The money came with like curiosity and going down the rabbit hole. The money was nice once it came I had no idea what kind of freedom or lifestyle or whatever existed. Now I'm probably just a chump. But I mean yeah I thought people in positions of power were like all shitty people. And I don't I didn't consider myself shitty. I don't consider myself a shitty person.

Alex: So you take the investment the like you project you know a hundred million dollars in new revenue that doesn't come but you're growing and you're sort of like growing more slowly than the investors would like. But then at a certain point you plateau you eventually have to lay people off. There's a point where you decide to step down as a CEO. Talk about that decision. What. What led to it.

Sophia: So as a founder your title is CEO just because, cause you founded the company you're like default CEO 

Alex: I’m familiar.

Sophia: And it's like why am I qualified to be CEO. I mean I'm a company of one, I'm the CEO and the president and the secretary or whatever and then it grows and grows and grows and people are looking at you and they're like you're the CEO you must now and you're like I don't know anything. How did this happen? I need to hire people who know. But I'm still like the buck stops with me. But I don't know how to hold these people accountable. I don't think I ever did. And my job eventually became a lot of like bureaucracy and just like stuff that I wasn't cut out to do and I'm really like a marketing person and I'm a brand person. I'm good at the merchandising good curating the entire business and connecting with the customer and intuiting what she wants and loves but doing that job was like I was in meetings all day and I was so far from the creative part of the business so far that it was just like it was a bummer and it wasn't it wasn't fun. And jobs are never fun. Didn't get more fun once I stepped up into the non CEO role, which was my decision. I controlled the board. You know like Danny was like Don't do it my investor, board member was like don't don't and I was like I want to. So I did it.

Alex: What did it mean? 

Sophia: I was still the boss. I still owned most of the company I still controlled board but I hired someone to whom the other C-level executives reported to. The learning curve for the business was just much steeper than the time I had to catch up. And I realized that and I put Sherry Watterson who was the chief product officer at our chief merchandising officer at Nasty Gal. prior that had been the chief product officer Lululemon and really really built the merchandising kind of design organization of of that business and it was a very it was a community oriented business and I saw the parallels between that and Nasty Gal because Nasty Gal was a feeling, Nasty Gal is like she was like I'm a nasty gal. And she was the most likely candidate for CEO. I don't know how you vet a CEO. I thought it did a good job and she was a lovely person.

It was a really challenging role to step into at the time like we had gone through layoffs. Like I wrote this book Girlboss and I put myself on the cover in 2014 and I was like yeah I did it and and then like by the end of that year like we had started laying people off and it was just like oh my god what is this? 

Alex: I mean so much of what you're saying is just like resonating with like I'm thinking about going through and trying to fit and trying to figure out. One of which is just sort of like this idea that like what got you into the position in the first place of CEO of this growing company is not the thing that you need to actually run the growing company. It's hard to figure out like am I the right person for this job?

Sophia: Yeah, I ask myself that every day

Alex: but I I'd be terrified also to like step aside because it does feel like my baby and I feel like I would and I think about it too. But I also feel like I'm definitely not ready to do that because I'm just worried. I'm just worried about like I guess relinquishing control or something.

Sophia: I think that's a good thing and I think I should have felt that way.

Alex: Oh really

Sophia: I think I was tired. Yeah I don't I would like to have stayed CEO. Would our would the fate of Nasty Gal been any different had I stayed. I don't know. Ultimately like I think our fate was sealed the day we were valued at 350 million dollars because it just cock blocked the ability for anybody to come in and be like your worth. You're making a hundred million dollars. You're worth 200 because our existing investors would have been like. No I'm not going to take a big haircut on my you know on on my valuation on what my stock is worth. Which is what happens when someone comes in in a down round as they call it. And that just like that was just it just we couldn't we couldn't raise. After that it was so hard. I would have like great buy in from like a private equity guy someone who was like deep apparel experience who could come in and really really move the needle with us and. And then he'd be like cool I want to talk so and so I guess they don't need to name names. This person who has been involved for a long time and that person would say if you don't if you can't value the company where we valued it, don't bother showing up. And then these people will just disappear like I never knew these conversations were happening and then a year later I'd be like hey you like what happened like we were you know I'm--I'm good at like I mean I'm just good relationships like I think I'm you know getting people excited about what we're doing and like really getting people to see the brand and what the potential was and it was it was a great brand you know. And then these people will just disappear. And later on I heard from more than one of them like Yeah I talked to so-and-so and they said like not to bother showing up unless you know. And then it's just starved us out just starved us out and starved us out of cash. 

Alex: And then eventually Nasty Gal had to to file for bankruptcy. Can you talk about the bankruptcy filing. Where were you how did that come about?

Sophia: So the six months preceding that were pretty wild. I wound up on the cover of Forbes magazine and then my husband of a year left me a month later and then I was in Australia promoting a book called Nasty Galaxy which was like oh god I did this thing called Girlboss, this book. I thought it would sell clothes it didn't sell clothes I guess I'll do a book that's like marketing Nasty Gal. So I was in Australia promoting that and you know you don't go bankrupt overnight like it was two years of layoffs and you know budgets and you know just moving things around and fundraising and deals just deal after deal. Hail Mary after Hail Mary kind of slipping between my fingers. And it just it just became like kind of like total hell. And I I could have been I could have been more involved I could have been more engaged. It was just so far beyond my ability to course correct at that point. So I was in Australia it was the day Trump became was elected that we had that final call and voted you know because it's like you're actually like you have a fiduciary duty to file you know really at the point of no return. And you know there was 24 hours 24 hours. We're going to get this through. This is going to happen. The fundraising, these guys are going to buy us this this this oh what's the chance of this. You know I would go to people and say what's the chance of this happening and when anyone responds 100 percent and there's not a paper signed they're a fucking idiot.

I mean listen I made a ton of mistakes like I don't know if I hired the right people I probably made some decisions too quickly and some too slowly like I was naive and young and again no excuse. There's tons of founders who were like 26 who were doing fine.

After the break…how those mistakes added up..and left Sophia on a stage in front of thousands..announcing that Nasty Gal was out of business.  That’s after these words from our sponsors.

(BREAK)

Welcome back to Without Fail and my conversation with Sophia Amoruso. 

Alex: So. OK. So you tried all these things and then on the day of Trump's election I'm going to go out on a limb and say that you probably were not a supporter of Donald Trump.

Sophia: No

Alex: And so on the day that he gets elected. You have to have the bankruptcy...

Sophia: Yeah I'm on a call with the board where we voted to send the company into into Chapter 11 literally in a green room before I walk on a stage in front of like a thousand women and the press broke at the same time. And then I walked on stage and not everyone, I don't think anyone in the room had seen the press. It's like what are you going to do not talk about it. It's like on the Internet all of a sudden and and I just I mean it was like you go bankrupt and five minutes later you're standing in front of a thousand people like what the fuck is my like biblical like weird ass like ride? What is this? It's so. It's like I forget this stuff cause I go about my day and I'm like should I have steamed vegetables for lunch. And then I say this stuff and I'm like what the fuck. So that happened and I cried.

Alex: What were they there to hear you talk about?

Sophia: My book and girl boss and being the girl boss and Nasty Galaxy and nasty gal and they love the clothes and the clothes sold in Australia and like whatever and there I am like I'm like crying on stage in front of these people.

Alex: What did you say?

Sophia: I don't remember but there was a sense of relief. You know I'm not supposed to say that but it was such a gruelling last few years. So many people's lives were affected by it. If I could have changed the course of that I would have.It was just like it was 10 years. You know I put in 10 years 22 to 32. I mean it's not my whole youth but I like to say that. And so it was like it was a little cathartic but it was still really really sad. But it's not like it wasn't a surprise like it doesn't happen overnight.

Alex: Right. Right. It's so weird that feeling like of just like oh my god like all this responsibility and like trying to make everything work and having it sometimes work and sometimes not and then that mix of just sort of like man if somebody would just if..

Sophia: You're not supposed to say, you're not supposed to say it. What did I get myself into? How did this happen. I just want to go home.

Alex: But then also, this is this is the thing I care about.. So after the bankruptcy you started a new company girl Girlboss. What are you doing differently now? What are the lessons that you take away from Nasty Gal that inform Girlboss.

Sophia: I mean everything. I didn't know shit at 22. 

You know I'm I'm I'm thinking a lot about culture. And it it's challenging like the most the most unpredictable thing about a business is humans and so I'm I think a lot about that and I think a lot about leading by example. I don't do dinner meetings, I don't go to the Chateau for the magazine party so I can like stay relevant. Like I don't care like the glamour is so lost on me because I was such a ho.

Alex: That was something you were doing back in the Nasty Gal days?

Sophia:  I did. I mean like I wanted to do all of it because I didn't. I had no access you know I didn't know what the stuff was. I thought it was really cool. Now it’s like I built my Rolodex drinking a lot of wine and not being at home and eating a lot of oysters and clinking champagne glasses all the way to fucking bankruptcy. And I don't care about that stuff anymore. 

I've said yes I'm now in like I say no period for like you know. Yes yes yes serendipity yes. And I'm like no, intention. No, focus. No. Now the way I think about like I knew the company was struggling when I was like yeah put me on the cover of Forbes magazine and I'm one of America's richest self-made women and like my stock in the company was still worth a lot. But it's like it's all like Monopoly money or money or whatever. 

Alex: It sounds like what you're saying is like you're you're focusing very much more on essentials and like less on sort of like the other stuff going out and sort of like taking meetings and stuff like that and the other as you said you're focusing a lot on culture.  What were signs what do you think about when you think like when you think back up like that was a sign of culture. That was that was not working. That I definitely don't want here in this new company. 

Sophia: I mean I had bosses sleeping with people who reported to the person under them. I had a guy embezzle 500,000 dollars from us. I had people with like a code word for our CEO that was like really offensive that they were using to their reports.

Sophia: There was a lot of like cattiness and silos and fiefdoms or whatever the fuck the words are for those things. And what was missing which I'm trying to do now is creating objective tools for people to understand what it is not what I want. Like oh Sophia wouldn't like that. Like I don't want that to be a conversation in a room ever whether I'm in it even worse when I'm not in the room. This isn't about whether Sophia likes it or not. Here's the brand look does this fit with that objective guide. This is what we're all signing up for. It's this thing. That's not me. I never figured out how to scale me. And then it became like a haves and have nots of culture and like oh this person is cooler than the other person. Well you know we should go with their ideas, Sophia would like that.

Alex: Well you reach a point. I mean this is something that is so this also just resonates so deeply because you can get to a place where like you can you just go by on the force of your personality at a certain size and then you get to a certain size and you're like oh right I've become but that becomes an impediment because like as you said like then people are judging like by how close they are to you and like getting access to you becomes the goal rather than sort of like doing what's best for the company based on the mission. It's like such a classic thing to struggle with and it's so hard to get right. And that is something that we struggle with as well.

Sophia: Yeah. How do you scale yourself? I mean it's if everybody starting with you and the people under you don't sign up for all the things that you talk about, it'll never find its way into the greater company and it's just a bunch of lip service and people don't. People lose respect so quickly.

Alex: You do have to be a role model and be a role model is a little bit of a buzzkill.

Sophia: Yeah. I mean who you talk to who you spend the most time with is an indication of who's most important in the company. Everyone is watching. Everyone is watching every expression every microexpression and they don't care how self-deprecating you are. You better know.

And even when there are things happening deep under the hood and people are you know maybe there's things behaviors that are not aligned with your culture and you don't know about it and you sometimes won't know about it ever or for six months. Everyone is looking at you thinking how is he letting that happen. Nothing is personal it's about getting the work done. Doing the best work possible celebrating the work and yeah having some fun along the way but your loyalties and everyone on your team's loyalties have to be to the greater business.

Alex: Yeah yeah. It's about taking yourself seriously as the boss.

Sophia: Yeah and it's hard because it's just like what how do I get here? Who let me in the back door?

Alex: You've got to fight your own imposter syndrome...but not publicly. 

Sophia: Yeah, I mean, there's something to be said for having adversity upfront in a business because you have to think about the things that will allow you to scale more beautifully. When something just explodes and you don't have haven't looked at those things like when the tide recedes there's so much junky shit hiding out like under under the water that by the time you discover it, it's too late to clean up. 

So like I want real substance in my life. Like again the tide has lowered and actually there's something really cool under it this time.

(MUSIC)

Coming up, next episode of Without Fail..

Longtime Hollywood studio executive Nina Jacobson has made quite a few hits in her life. The Sixth Sense, Remember the Titans, Pirates of the Caribbean, and most recently, Crazy Rich Asians. But she’s also had her share of flops. And she says you can tell the flops right after that very first screening. She remembers one in particular:

NINA JACOBSON: Afterwards people would come up and congratulate me on what a brave movie it was. At which point I knew, that I was fucked. Because brave is code for stupid in Hollywood. And I was like, oh god.

That’s next on Without Fail. 

Without Fail is hosted by me and produced by Sarah Platt. It's edited by me, Nazanin Rafsanjani and Devon Taylor.

Peter Leonard mixed the episode. Our music is by Bobby Lord.

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We’ll be back next episode. Thank you so much for listening.