#72 with Sophia Amoruso - GIRLBOSS

Date
Duration
48 min
this episode is brought to you by super sides so super side dot com if you need something designed quickly go to super side dot com give them a try that was it like i have savings and i went from upgrading from my eighty seven volvo to a a year and a half later or if i can hand me i'm was like what is this i can like my everyone oysters off the net what's up i'm here sam's here and we got special guests sophia so we're just explaining what this podcast is and i think we're we're kinda shit explaining it because most people when they come on a podcast they're like cool these people are gonna interview me and we kinda do we do ask questions because we're curious but for the most part the feel of it is what if the three of us were sort of at dinner and we were just shooting a shit on stuff that's interesting to us and let the conversation go where it may and that's that's really the the overall vibe of the podcast and so so we can start with whatever sam's roger book i've read or twitter i have a question off your twitter that's just a a fun little ice i saw that you tweeted a very controversial tweet actually not so controversial because many people would agree you said that peter is a national disgrace you watch the bachelor oh yeah yeah i thirty seconds why is peter in national disgrace man my boyfriend was saying last night i was like it's okay like you're into the bachelor and i was like i'm not into the batch if you watch it every season that insert into it and i'm like that is not part of my identity i am not into the bachelor and i guess what you do it's who you are right what is that like ben new butt or something and he's like a dupe he just like he's just like the most generic i just don't know how you find people that generic yeah there's just like no devi whatsoever and not just like creeps me like i think the word is basic yeah basic i think what he to be where this guy pretty lot all here this guy's yeah he's pretty he's pretty universally disliked as the bachelor nobody dislikes him because he's not controversial he doesn't do anything that necessarily that bad he doesn't also do anything period he's sort of a non decision maker which is yeah what you're just like flip flops and hurts people why would you wanna take that not great okay so that's your thoughts on the bachelor sam you read the book so i think you you have maybe some some more interesting questions than than well i just had just i wanna dive deep in all this but but the first quick question is what type of porsche do you have hi john that's like that's like many cars ago what do you have now i i did the portion then i did i had like the jaguar f type like right when it came out again which is just like why am i driving a sports car like i like car well and and that type is like a super car right or is that the suv no it's yeah it's like a it's like a ra race car right like like the wing that's you the the doors go up i don't think they go up but i do have the model x now and the doors do go up but so i had the f type and then i had a range rover for like five years i wrote girl like seven years ago so i've been through many cars and now i drive the model x and i like it a lot what type of porsche was it it's savannah worth it or not may i hear mixed things on that it's huge car i mean honestly anything other than a tesla feels like driving like an agent in the past like why would you pay to like hassle with car or whatever it's called i i don't know i i was about to buy the model x a few months ago but then i got spooked because i'm on twitter all the time and i ended up in this rabbit hole on twitter of the people who believe that tesla is like a giant fraud like great product but the company is sort of in dire straits financially and it's pretty convincing if you end up going down there like most conspiracies if if you sort of go down that road you'll end up believing you know somewhere between thirty and eighty percent of it and so i got spooked by dan i was like okay i i don't wanna buy this car if this company is not gonna survive long term so that was that was my takeaway what do you think of that i mean i own s tesla stock and i'm really enjoying the volatility and i'm like in it for the long haul i you know in terms of tesla fraudulent it's like what company isn't at some point it's like think it till you make it i mean he really he's like very much a a liability but i mean it's just a great product so also the model x is over six thousand pounds which qualify the inertial vehicle which means you can write it off yeah that's what i ended up doing i ended just buying a really big heavy bmw to to write it off yeah i i didn't know about this so sofia to the listeners you i'm gonna give your i'm gonna tell you folks what i know about you and which is that you started as it was nasty gal originally it was a vintage closed shop which i did i used to work for that tv show called american picker and we went by buy and sell a ton of old the other jackets and things like that so that's one the reasons why i was interested in you early on years ago and then you scale that to just nasty gal dot com i mean like a a proper menu clothing brand it got quite huge and then it went down as it went down as fast as it went i mean was roller coaster server ride right and walk faster the day it it was a roller coaster and then you went and launched girl boss which was a well it's a whole brand of books and tv shows but a social networking site and you sold that to nick bell at attention capital right yeah so joe mark casey nick bell i don't nick is not even super involved anymore so that's interesting so the company at the end of last year to you know joe's like that friend of mine for like five or six years just someone like a really bug who's been one of girl bosses and my biggest supporters like put my end indigo lost before i even had a deck you know just months after nasty all fell apart but yeah that's the gist of the story it's a real long story and when i wrote girl boston in twenty fourteen that was you know that was i wrote that when i was like at my tea and i was like naive and like on a high and i had experienced adversity but like a warehouse melting down customers being angry but not to the extent that you know it was coming for me and so i'm writing a book right now that's you know it's not gonna be out until twenty twenty one i think i'm calling it tough shit and it's everything that happened after a girl boss so like the two years before now city face planted and everything like a divorce like everything that could gone wrong went mom pretty entertaining how big was nasty gal at its peak yeah so we over a hundred million in revenue and the company was worth like three hundred and fifty million dollars so index put fifty million in i booth bootstrap it to twenty eight million props and then investors were like who is this free because the only thing i understood was you buy something for a dollar and you sell it for two dollars and then you invest like a dollar twenty five and like don't spend more money than you have to like how often are you gonna have a business if it doesn't like produce money i just didn't know i'm a community college dropout so it's like buy something for more sell something for more than you buy it for and then don't spend all your money like it's pretty basic oh front well and at twenty eight million in sales bootstrap what we're what was the income off what's what's an income off twenty eight million for that type of business what was the profit i don't even remember honestly i was just like at that point i had saved over a million dollars in just cash in the bank like i have a screenshot like the basic bank america of america like bank account where and and and also under it is my personal account and i have only like eight grand like i didn't really pay myself i didn't stuff well the business had a million and you and you were all in i just like i mean i was all in and that like i there wasn't like equity i just like was a small business owner of a business that got big it was like a mom and pop shop that got big so to me it wasn't like oh high risk i don't have you know a lot of stock there was no stock and so i owned a hundred percent of the company until index came in in twenty twelve and invested fifty million on a three fifty post and after that i owned eighty percent of the business so that's great index come from so were you out like hey i need to go raise money or did somebody say hey this thing is taken off let's go talk to about venture capital yeah venture started like sniffing me out like they started coming to me and i was like know i had an adviser who was like just build it as big as you can because then you'll sell less for more and also simple math right so i you know i didn't we didn't need the capital but i was like whoa you someone gives my company that much money and all i have to give up is like and i still control the whole thing and i how those numbers came about how did the number because i i've done this before when you raise money and you know sometimes you go in and looking for two and they're like how about seven only what okay seven million that sounds good what was the valuation and then they throw out a big number how totally i mean they wanna own their twenty percent right and it was a growth it was the first money on was out a branded growth fund right it was like the second investment out of that after like their big investment in dropbox at the time so think growth rounds or you know people aren't looking to you know play small bets they wanna own they wanna own a significant amount of money and then or the business and i i didn't like game it like i didn't i was just like well that's crazy you think worth three hundred and fifty million dollars and we're making like thirty million in revenue whatever i didn't like you know have more than one term sheet i never when i think i might have like barter the way you barter like you know like a like an estate sale and i was like no this much for this much and that was like that was it right it took some money off the table that was totally life changing let you say how much no no how'd you decide to do that because me and sam both been through this where we're trying to decide how much and you know investors are are cool with it if you have momentum but they're also like look we're not we don't want you sort of sleep in soak sheets every night either so how decide the amount just pick the number good yeah because the company didn't need need money they were just like i didn't know what secondary was and they were like yeah like well you know a company doesn't need fifty million so here we'll put the majority of it right into the business but you know more than half into the business but a lot into my bank account because it was just it was still it's it's just the same stock like they have the same position regardless and you know at at the growth you know stage especially when the entrepreneurs you know still owns a significant amount of the company like you're incentivized even if you do take a money people if you're not diluted to the point where you own like ten percent of the company like you know have like fuck new money then like that's a different position but for me to have that big of a stake in nasty gal and and yeah like be able to like not worry about you know their whole thing is like we don't want you to like worry about money which at the time was like i had a paycheck but like that was it like i didn't have savings and i went from you know driving like you know upgrading from my eighty seven volvo to nissan mara to like you know a year and a half later fucking pan and was like what is this i can like buy everyone oysters that do would the would the company have thrived had it not taken any money i don't know what do you i think the expectations would have been there weren't expectations it was just like great like we won't spend more money than we have and i never would have honestly like i wouldn't have known how to control like a company's finances but i did have great people who were the kind of people that had built profitable businesses they weren't the operators that come in from venture backed businesses and you know understand you know wild expectations that you know when it was a bootstrap business we just didn't have it all yeah i think so like i think i probably would have sold the company for like a fair amount of money i mean at one point there was an urban clothing retailer that offered over four hundred and it was like four hundred and twelve million dollars on like a piece of paper when i owned eighty percent of the business and my investor told me to ask for more and it went away fuck how that's well hold on hold on we can't take you shopping that's amazing what was that like like whatever you know they were convinced they were like no it's gonna be a billion dollar business i mean to them it's just like a drop in the buckets it's not like you know it doesn't work out i mean it's just like go big or go home you know if and if they invest at three fifty and it returns at four hundred that's how a win that's a opportunity lost there to why something else yeah they're like why bother and from that point on when we did need to raise capital after that or tried raise capital after that or other people like largely when other people came in and we're k we wanna to invest at of this valuation that was still like a healthy retail evaluation i was cock like they didn't have control but there would side conversations you know after like i someone up and they totally bought i'd be like great i'd love to talk to your board member and i love this guy i always love this guy and after like like a few like they just like kinda disappear personal reason and i didn't really connect the dots eat and at a certain point you know at six months later i reach out to that person to be like whoa you like totally goes to what happened and they're like yeah your your investor told me to like not even show up unless i paid this much and that just happened like behind the scenes over the course of like just like started us out for a long time when we could have had you know much better terms two years or year and a half before nasty gal fell apart i just you know that was stuck that i wasn't i i didn't know what's happening so why did you raise money again then for girl boss why i don't know honestly because know because i i like wanted to do a conference and it wasn't prop the the conference was initially profitable but it wasn't like profitable enough to build a business because i had seen what enterprise value can do and like i get paycheck for the rest of my life or i could go like build another business that's worth more than the revenue that's coming in and girl bosses is a really powerful brand it's an amazing opportunity there was like so much grounds well behind the brand because you know i i founded it in twenty seventeen that was whatever fortune three years after you know the book was a best seller the hashtags been used twenty nine times on instagram and then i started business because i knew there was like this i i had our first conference a month before the netflix series came out which was gonna put the name girl boss and do of a hundred and fifty million homes in a hundred and ninety five countries so i was like oh shit like i better build the mint that like catches all out awareness like i can capitalize on there and and i did but not to the point of like you know i haven't i didn't sell a company for like the brazilian doll ever so my my company the hustle you know i don't don't need i don't have no idea if you know you're not doesn't matter but we started as a conference so i started it did you read sam's book yeah have you read have you have you googled me no gonna box i need during books it's like it done it's like how right so we started it as hustle con and so at we get up until the stupid stuff going on now tens of thousands attendees and i used like the about the first half a million that we made off the first event or two as our seed money so i hear you in conferences it it gives you a little high too they're quite challenging to scale to be very large but it is possible did you like the conference business as a business no but as like an event yeah it's like it's really fun it's really fun to see these women from our community coming out and meeting one another and women from thirty countries flew out for the last one like forty one states or something it's just awareness of g is super distributed because the book was in every report in bookstore in the country so it didn't like start in the cities or you know it's still largely in la in new newark york but very like broad fraud like awareness and so to see just like all these awesome women to descend on los angeles and york and get so much out of it is a great feeling i'm not an ex so getting on stage is like i don't love it but it's like part of my job so there was that part but i loved everything else about it you you and i are from you know i feel like i know you and even though you have no idea who i am because i've listened to your podcast and read your book so i feel as though we're a little bit similar and sean as well in that it seems like you're very creative you're pretty you're a pretty good business person but you're more so creative than anything and do you what what would what's your whole take on operating the company and like running it versus starting it and working on like weird projects like were you running i don't think you're running nasty gal later on were you i did for the last like couple years i i like opted out i was like i don't wanna be i just don't wanna be a ceo i'm not creative anymore and stuck in meetings all day i'm not a great operator i'm like the worst operator like i've done stuff with my executive coach and that's top is like entrepreneurial creativity like autonomy me all of those things are important to me the bottom is general management like people at the the the bottom so i've had to be an operator and just by the sheer nature of having founded companies i'm not very good at it i'm i've gotten a lot better at building culture i don't think i'm a great business person honestly like i think i can build excellent brands and i can drive revenue i think i'm an excellent business person when it's like very hand to mouth i don't think i am when there's just like i don't know just with venture just expectations and it's just floating in the ether like you know your business model works when you start a company it makes money and pays for itself like that's still i think what i'm still like a small business person that happened to build like big businesses but more than all i'm probably like a voice in a brand you know creative and a marketer do you think that that a lot of people don't don't do that as much or at least people in the like the silicon valley pop culture type of realm they think that hiring a ceo is actually silly because you see folks like the the the the famous entrepreneurs are still the the ceos in some cases i don't know if that's actually the reality like they have strong operators like it's i think it's more common than people realize but this is the whole idea of hiring a ceo or hiring someone to run the company is still a little bit frowned upon i've done it you did it do you think that that was a good move and do you tell people to do that i feel like it was frowned upon i mean the headlines were like that i stepped down but i like stepped up into like a broader role is how i felt but that's what i'm saying that is frowned upon like like what i don't say i'm not saying it's actually frowned upon but a lot of people view it as something that you shouldn't do as a negative event when it happens really event i mean whatever i mean yeah i thought about how it would be perceived and it was i don't give a fuck how it's perceived i'm saying a lot of people in accurately like they may think you shouldn't do that and when i'm in my opinion i think a lot of people should and what i'm asking is do you think that other people should as well totally i may i think it's individual i think pretty much every entrepreneur who's raised venture capital like had a head star like i had never worked in an office or had a manager like my last job was in the lobby of an arts school so i was probably never qualified to be a ceo and you're a ceo by the sheer nature of being a founder but being a founder and a ceo you inherit that title to me like i don't care about titles like i don't i tried to name everyone in the company a c founder but they just like didn't catch on like i was like cool you're all c cofounder put that on your linkedin like i don't care because i just never was like never a goal of mine right so like i don't i don't i don't i feel like in terms of like what i remember and how that was received and whether it was frowned upon or not i've had so many other things that were frowned upon that were much more noisy than that that it just i think it's fallen into the background because i've been like frowned upon like plenty of times much more loud in a much more loud way than having stepped down like we're throughout much bigger reasons or noise what's an example of those frowned upon moments i mean giving sued going bankrupt like laying people off talks culture i mean like a netflix show being like hand tmz covering my divorce like i don't know some stuff and the the skin is thick now or or has pretty thick was pretty thick yeah was was it always was that worth no no i don't think so i mean it was until you know and then writing about this in the book it's just like when people don't know you and they have they judge you it's just kind of like they're totally un qualified but and people's you know it's great on a conference stage to say like i care where other people think and it's like great on instagram to be like care other people think once you don't care about what people think it's like how do you learn and even if it's like totally wrong and coming from something someone who's totally uninformed like i i i do have thick skin but at the same time i have to first assume that everything is true and then weed out the things that aren't true because if i don't consider that things that are said about me are true like it's not an opportunity to learn so as painful as that is and as long as so much of it is like i do think that caring about know what other people think but what i guess like what you're how how other people feel as you know can't argue with people's feelings right well and you you're kinda like a i mean you're kinda of famous like you this tv show is quite popular you have a book all over the place it seems like you got a pretty big personal audience on a a variety of social channels but you said you're introverted and you didn't start the shit to become famous you started because it was a cool it was just like a a cool hobby that made money and it spiral into something it you know bigger what why do you think like they're writing about you on tmz and shit like that i mean that's like mainstream stuff well i think with tmz it was like the are call it quits at a girl boss pays access pigeons like i had a great p and yeah because that's what weird right like mainstream my story is a rare one which has made things a lot more difficult for me but at the same time you know i'm i'm at community called dropout out from sacramento every other business book or anyone any other story even of women for the most part that you hear they have like a a leg up in some way not to say that you know i've i've you know plenty of pro privilege that i started out with but you know education and even working an office or having a manager was not one of them like i started a business with the tools that most pretty much everybody has which is like a digital camera and a laptop and access to state sales and thrift stores right like you know there was no like i don't know what supply chain was or like we weren't i was manufacturing things i just had access to stuff that everyone has access to and i had probably less of an education than most of the people who wrote the book so i think it inspired the rest of the you know world or the rest of women who you know may be accidental entrepreneurs and have side hustle who didn't feel qualified and that someone who was totally un qualified on paper i was able to pull off what i did but he gave like in some ways i don't wanna be like i get a generation hope but in some ways i think my story has alright this episode brought to you by super side so here's the deal i'm incredibly impatient like horribly impatient i get a an idea at midnight and on eight am the next day i want it done and unfortunately hiring people to get that stuff done is really time consuming it takes forever so super side dot com here's what it does you go to super side dot com they already have a team of designers ready to go you tell them what you want and they get it done it's twenty times faster than traditional hiring and fifty percent more affordable than agencies if you need something designed and need it done well and fast try them out super side dot com i've used them before love them tell us a little bit about the book so books are a funny thing right you you know getting one made is this like weird process and then you know the the point from where you have a story to it's sitting in every airport on the you know on the display stand as like buy this thing there's a lot that goes into that some of which you control some which other people control some of which is just luck so how did your book get so popular was that something that do you feel was like like the easy answer is i don't know people just like it word mouth it just spread and then there's another side of the business where the right publisher with the right kind of footing can get you can can kinda engineer a lot of the the growth so how does a book so popular how did your book gets so popular yeah i mean i tried to drive as many pre orders as possible and not see how to shoot million person email list at the time and for me this was an opportunity to market our story was content marketing i got someone to pay for us to put the logo of my company on the cover of a book like that but like a marketing too like all of these things felt like marketing who's not like opportunities to market myself or for me to have a personal brand and instead of the book selling close the books sold books and like my story which isn't like oh whoa i'd never knew that putting myself on the cover buck when like whatever but i also had no idea you know it would go on to sell half million copies and be published in like a brazilian languages and spent twenty weeks on the new york times best seller list like do you know that you know girl us had an impact on the initial top to get us on the list but you don't stay on the list that long if your book you know if your book doesn't have merit is is five hundred million or sorry five hundred thousand five hundred million would be great but five hundred thousand book sales is that a meaningful revenue driver for you or that that was good money like the the royalty is like trickling now but for those first few years that was like meaningful for me which i did not expect like i earned out my advance like by multiples you know what's a what's a typical advance for that like half a million dollars or something oh god now more less i have no idea maker less like i mean i was just like an un unproven author with the story that like a lot of editors you know even women came to the room read my my proposal and call it and were like you think this is tiffany a niche we don't think like that many women like wanna start businesses they wanna buy clothes we're like i don't know what they were but like i got turned down by you know a handful of publishers and then carrie colon who was at penguin at a time she's at audible now was like yeah i get it awesome and she was kinda i mean she she made the book better but she wasn't she didn't try to make the book what she thought she wanted to to be she just let me run and write a book and that's when i do my best i cannot be told what to do because i don't do a good job and yeah there was an advance but i think it i don't remember it was like maybe one fifty like i don't know i don't remember but like did you do a good job in your opinion now of negotiating the book deal because publishers have a lot of leverage it's almost like venture capital but even worse like this yeah i less i still don't think that i've done a good job with my existing book deal and i'm working on the next one the thing about advances is that like you can get a big advance but if you don't earn out your advanced no one's gonna publish your next book like everybody sees the performance of your book so you either earn back your advance you know on top of your you know if you make five hundred k like you make that two fifty on top of a two fifty k you know let's see like i don't know i got it now but basically if you sell five hundred k five hundred thousand dollars worth of books like you know year breakeven if you sell two hundred and fifty thousand dollars of books like if you try to do do another book deal you'll be held accountable to that so it kinda doesn't really matter you'll say make the same amount of money it'll actually be incentivized to out earn in your advance if it's not that big because it's easy to be like cool i made money great about you know have you so tim ferris was one of our angel investors and we're not i'm not terribly close with him but i should share it with him every once in a while and he has said something like his book was a great like revenue wise at the time but he goes my podcast is significantly bigger in terms of revenue and my angel investing has been way bigger beyond that have you ventured into that world of of start up in investing the early stage companies yeah so back when i got that like big windfall of money i i worked with iconic like mike and those guys like awesome like money i know they've worked only worked with like people who they think who's at least network on papers is like outrageous and mine was like two hundred hundred and eighty thousand million whatever is is iconic mark zuckerberg thing or is i i think that he's part of it but it's not his he's but they got it at some point they managed this money i don't know who they've work with now and and i was invited to invest in there fund so i'm an lp in there fund and put like five hundred k in i put like one fifty k to index is fund this is all back in like twenty thirteen maybe i put like a hundred and fifty k into first d back then i was invited to invest in blue bottle at the time and it's like i didn't drink coffee yet so i was like i can't invest in things i don't understand i like furniture and to a bad idea but brian mee his ceo is like a great friend invested in in my businesses and then i've done some angel investing so i just invested in public dot com yeah i just signed up for it last night yeah so i i'm there i'll follow you i'll i'll look at know yeah you're stocks so i'm an adviser and an an an investor so if i get adviser shares then it gets me up to a point where i have significant stake in the business at least for an angel investor so i feel good about that i invested in something called boo land that's some it's right sustainable yeah cleaning products where instead of using single use prop plastics where you're buying like wind index and eighty ninety percent of what's in that bottle as water and you throw the plastic away they send you these really beautiful reusable bottles and you fill with water and you drop a tablet into it the only thing you buy over and over again is the tablet so the founder sarah pai is super impressive what else i invested in passport which is like a international logistics company they just created a series a i'm an advising there invested in coming park show house oh i invested in liquid debt been drinking it what has been the most lucrative angel investment you've made i mean none of them have returned anything yet but i think first tips is probably like you know they've gone to raise several rounds the iconic investment has you know they i don't know there's like black line and alibaba blah and like a bunch of stuff i invested in back in like twenty twelve twenty thirteen and that stuff like got dumped into fidelity or however it works and i just pulled all of that out i made enough money on it to be like alright i'm gonna like pay those capital gains shit in the bank it's just cash like for now and then i still have like i a lot in my house which is stupid i'm sick overexposed in real estate but i live here it's awesome and and then i have are you in la i bunch in like morgan stanley now manage just that stuff i'm in la i'm up in the hills crazy nice and you know you've done a whole bunch of stuff and i i feel like your your story is cool because you're like okay i didn't sort of expect to go down this path but probably every few years you look around and you're you've hiked up this mountain and you're like wow okay i see a whole bunch of other possibilities now man what's like i don't not like a ten year plan but like what do you see yourself doing going forward do like are you gonna start more businesses do what do want such an interesting question because i in some ways like what i've done wasn't a choice because i'm am a person who's like oh my god opportunity like grow bosses is the only thing i can do after nasty gal it's like the opportunity to redeem myself if i do a good job i can build a happy culture i can build and sell a business and exit and like kind of like heal my with all my scars from nasty gal by you know building something that you know feels better but i didn't you know things i put things into the world that just like have momentum and then that's my life been fourteen years since i founded nasty gal i did that for a decade and this quarantine team thing has had meaning like wow like this is really different i i like working from home i've done my best work solo so i started an ebay store by myself and then it became this big thing i you know i wrote a book alone and it became this like big thing and then i like i have to cash all i mean of course we we should all be and i am so grateful that any thing i put out to the world not anything but like the things some of the things i put on the world just catch fire in that way but that leads me to in some ways just being like behold into the opportunity which is like oh boo right it's like i like had just raise money me again and you know build a business but at the same time my lifestyle is not something i've ever thought about until recently so when you're an entrepreneur you don't work for yourself you work for your business and that comes you know just like what you do is like what the business demands and i'm feeling like you know in the future i wanna have more choices like i you know i i i at some point wanna just work on a smaller i i don't wanna start a company i can so there's that wait wait you don't wanna start a business again no you wanna you don't wanna start a company or a business it doesn't mean she won't she just doesn't want i never wanna raise money issue equity or like build a large team again so do you have do what do you do now i mean are you working at girl boss yeah i'm working with girl boss i mean right now it's like we can't do our conference most of our brand partnerships fell through that's i mean we had something signed that was like four times last year's revenue that would have been a a one one check for a year long deal and that was signed on you know to cfo was desperate for counter signature and then back covid so this shit's really affected our business i have a great operator and have a great vp of finance there's obviously attention capital who are super dug in but the fate of g boss is really uncertain and so like everybody else i've had to think about like oh shit what happens if you don't like make it through this no investors just gonna indefinitely fund the business but it's like may not be viable for the long term even though i sold it like i don't have control over what happens next and i'm writing my next book and i'm you know doing my up like on weekends but like day to day with g boss i'm really more you know leadership position with the team and spending time with our team and having individual calls with people we have our daily stand ups i'm on those but like a mechanic stuff of of like operating the business day to day i actually have a great team who's doing there but what's next i really don't wanna think or talk about what's next because you know of course we think about the first place we go when our future is uncertain is like you know it's natural and human just be like oh shit was you know and the fact is i'll be fine i i i do well with what i you know between speaking engagements and working with brands personally and what else like books and there's other can i ask you a question about girl boss's business model like i think that for a minute it was like a social it was almost like a a computer link yeah it was like a community now it's kinda like a media company or at least that's what it looks like from the outside why don't you guys just charge these people like thirty fifty bucks a month or something to be part of the this community it seems like it would that would be the initial idea so venture is interesting right you take advice and it was built there's a there's a pay wall that we already built that we were gonna launch it and then that would be a a great business but she's pointing out it's not a venture scale business now i i just so disregard that before we launched you know i have a phone call with my investors and they were like you know don't reinvent a business model that already works no one has launched a social network that you know you have to pay for you have to like at least prove yourself first make it free and then add you know premium features and so a month before launch and we didn't have great cash flow we you know we were like tied on cash already launched something that didn't drive revenue because it would be sex for venture investors and they'd like understand you know something that you know isn't like a subscription social network that we've never seen work before and so the media business which is what we started out with all of our revenues has been from brand partnerships outside of ticket sales for the conference all of our effort went into building something that would be sex year to venture capitalists because media wasn't right like no longer or they've already invested in buzzfeed and advice and everything else with vine and like everything those guys took all the money and then the world changed and be building media companies unless you're transact transaction with your consumer directly which you guys have done such an amazing job at your you know you're reliant you're behold into so whatever it's happening with brands in you know media world so i wanted to build the community that we had offline online because it was just so massive and so special and to be able to connect the women from all the countries that flew for the rally who paid to put themselves up to paid for conference tip conference ticket to give them the opportunity to connect with one another and to bring our lines a really special thing and you know there's people who couldn't afford thirty bucks a month so it felt good to bring something truly democratic forward but it wasn't a great business decision it hasn't i mean obviously it hasn't generated revenue for us but it's something i'm incredibly proud of yeah i i i i hear everything thing you're saying it it's is you kinda putting in a in a hard place here and that's a bummer because i think that this i'm looking at now i think that i i think it it it can it's it's great and it can be even better and it sucks at that business model was people persuaded otherwise because i think that actually the original thing could be awesome yeah we were gonna build an app this year and that's just kind of hold guys doing so we were gonna keep growing it you so you have a huge network you have your hand in the mix and a lot of different things what opportunities bit in business models and spaces do you think or are you spending a lot of your time or you're looking at you're like oh my gosh this this is gonna be this is it's something incredibly fascinating you already said the cleaning company but what was it called blue land blue yeah so i think sustainability you know something else i i'm looking at called cloud paper that's it's like a hundred percent bamboo toilet paper so they cut down like zero trees they're they're they're raising they have a lead know we've got in touch with me and i'm just not sure about it but i think sustainability i think i mean i'm not super deep on fintech but there's another company called main street that's super fascinating who raising who i don't know how to describe it but usually like government incentives are just the super like opaque world where big companies know what a whatever opportunity zone is but like you know small businesses and venture back startups it's just this like you're piecing together this all of these possible grants and you know stuff that is out there for small businesses and so main street actually consolidate all of that and works directly with gust and you're i don't know whatever your payroll system is and with you directly to just basically they they save like on average companies they work with like thirty thousand dollars a year i think and so they're kind of like your central hub for those kind of government and incentives and just navigating that world which is often just very challenging for small businesses i don't know this is awesome yeah cool yeah i like just like money's around you know what do what are you freak freaking forgetting about even startups like those are great actually examples but in addition like what are you just interested in learning about like what are you like just curious about where you're like i wanna read more about that i wanna people who know about this is there anything that's got your curiosity i mean i'm kind of interested in people who build personal brands because it's just like super weird but i think it's something like i should be doing more of but like i don't need the house and i don't know what i'm supposed to post out i just like the lean startup up like couldn't and degree like i just fucking donated all of those books because i'm like i've never raised venture capital with like i i'm just like so happy to get rid of those books and like i've thought you know i've got some meditation books and some design books and some like weird witch books and books about like building habits i think i'm just i'm interested in you know i've only read non fiction that like benefits me like right now to build my business literally like in fourteen years like all of red shit that's like i can apply this right now like and i wanna read things that like benefit me personally or maybe spiritually or my you know i could become a well rounded person i never could do that out so i think just like things that have less to do with business like i don't really wanna to read about business again anytime soon i i i'm in the similar boat you i've been reading a lot of fiction just like american classics like catcher in the ride just like stuff we used to reading in great school but i wanna recommend something to you because i like i said i you and i have a little bit similar personalities where like chaos is kinda like the comfortable place to live in and but anyway there's this great book it sounds like a horrible book but your personality is very similar to this guy his name is felix dennis have you heard of this guy mh he's kinda like he's british he's dead now he got a cancer about ten years ago he he started maxim magazine he also started micro warehouse which was a large publicly traded company he if i had to describe him i would say he's like richard branson but more vulgar and it admits to being in like a coke head and like a and like a rolling stones like he's kinda like mick ja if mick ja was like a little bit more responsible and in business and he's got this great book it's horribly title but bear with me yeah you you just can't tell her the title the the the description was great but as soon as you say if you had said the title up upfront i don't i try to tell the title because it's it's so off putting it's called what's the title shot is it how to how to get rich to get rich that's it's horribly titled but the i know was like offensive or something but it's like he he it's it's exactly what you're saying you're not interested in these like sort of business book i know but he doesn't write that way it's not he writes an air he like he like loves poetry and he's just such an interesting person and he and he like tells funny stories about it's kinda like like i said it's like going on tour like with the rolling stones so that's kinda like i what i feel this guy's his life is similar to but he has a lot of amazing advice on how to delegate to your employees how to hire people but it's all woven in this kind of like rockstar like interesting book i would highly recommend reading that it's super interesting i use it as a reference book on how to manage people but it sounds like that book that guy solved a lot the problems that you seem to struggle with it's super interesting but in this business but it's written in a in a in almost like a fiction way yeah i have to commit to actually re mean like i in through books like i let the like of the scent i just let the scent locked up and i'm like it's like a camera cool i get it like i get enough of it i don't need to finish this book and honestly like buying books is like enough of a statement about like oh this matters to me like i know it's like spending money but it's just like oh this it just like solidifies something that's important to you like i'm i'm gonna pay certain amount of attention this even if it's buying a book that sits somebody books show when i fly i take xanax because i hate flying and i i don't drink alcohol but i take i a fair bit of xanax when i fly and every single time i go to the airport i leave with two hundred dollars of the books because i'm a little like hopped up and i'm like oh the best books at the airport you're like oh this looks awesome this like come back with a massive bag i do that with magazines i'm just like not talking about me anymore kidding sean is there anything else you wanna go over no this been good i i gotta say you are incredibly candid and i appreciate that you know i i or i i get honest i think it's a better way of saying it because mo you know we we have some people on here and actually we stop bringing on guests for a while because i was like what's the point i don't want this person's info commercial they're sort of you know you try to talk about anything that was difficult or messy and then they give you kind of like the the story that's like i had first thing i overcame and it's like my biggest weaknesses that i can't care tomorrow yeah and so i actually anytime there's like a guest episode i'm like okay like i get it you know i wish we could just have the conversation offline honestly it'd be way more interesting this what to me was like a conversation of if we were you know whatever at the bar just having drinks this is that conversation but but on a podcast so i actually really feel grateful that that we had this conversation thank you i'm around feel free to reach out i think you have my email if you if i think you do but yeah this has been blast

Episode Notes

Today we hang out with Sophia Amoruso (@sophiaamoruso), founder of Nasty Gal & Girlboss. Her story is bananas. She is a community college dropout who created a company that at its peak was valued over $400M+. She has had highs (sold over 500k copies of her book) & lows (nasty gal eventually crumbled) and we talk about both. I was pretty blown away by her honesty. She wasn't trying to make herself sound good or look good (which ironically, made her sound/look great to me). We start with some fun topics like The Bachelor & her favorite cars she's owned (2:23), About her background and businesses (4:45), The story of Nasty Gal: $30m revenue, Index putting $50M investment and her selling life changing secondary (6:44), Expectations after raising venture capital (11:31), Starting conference businesses (15:54), Being a starter vs. operator (17:16), Downsides of being the CEO (20:52), How she got her book to sell 500K copies (24:54), Her investment portfolio of startups and funds (29:17), What's in store for her in the next 10 years? (32:45), Freemium vs Subscription for content (37:13), Opportunities and trends she's seen in the media + retail space (40:06) and Sam's great book recommendation with a horrible - How to Get Rich by Felix Dennis (43:27) Today's ep is possible because of Superside! Head to www.superside.com to hire a dedicated team of designers for your project! 

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