Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders
Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm.
We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue, raising $50 million, scaling it to $120 million and a massive team, turning down a $400 million acquisition offer, and ultimately declaring bankruptcy.
She takes us inside what it was like to fail so publicly, what she’d do differently next time around, lessons from building the brand, and why she started her VC firm Trust Fund to back the next generation of founders building consequential companies.
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Timestamps:
(0:59) Selling vintage on Ebay while working at an art school
(04:31) Lessons in marketing and perceived value
(12:38) Knowing when to make your first hire
(18:31) Borrowing from others to build a unique brand
(25:17) Growing to $120m revenue in seven years
(27:24) Sharing the pitch deck that raised $50m
(30:17) Mistakes scaling to 100’s of employees too fast
(34:48) Downsides of raising at too high of a valuation
(39:56) Why being a CEO is fun
(42:57) Declaring bankruptcy
(50:38) How it feels to fail publicly
(54:41) Writing a book, Netflix series, starting the Girlboss movement
(59:13) How to create a new brand in 2026
(1:05:34) Starting Trust Fund to invest and help founders
(1:13:45) Raising $5m from a poker game
(1:18:47) Sophia asks for Turner’s LP pitch
(1:26:53) Traits of the best founders
Trust Fund: https://www.trustfund.vc/
Pitch Trust Fund: https://www.trustfund.vc/pitches
Nasty Gal: https://www.nastygal.com/
Follow Sophia
Instagram: https://www.instagram.com/sophiaamoruso
Twitter: https://x.com/sophiaamoruso
LinkedIn: https://www.linkedin.com/in/sophiaamoruso
Website: https://www.sophiaamoruso.com/
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All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158
Today’s show:
It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more!
It’s an essential watch for anyone building or investing in companies in 2025!
Timestamps:
(0:00) Introducing our amazing investor panel!
(03:15) The panel shares their First Fund experiences
(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
(11:27) Show cont…
(12:46) Where we’re at on the investor Greed-Fear Index
(13:54) The delicate art of investor discipline
(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(21:59) Sophia’s criteria for a follow-on investment
(24:17) Founders are going direct on social media
(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.
(30:49) Show cont…
(32:33) Why we’re seeing so many more Series Bs
(33:30) So when do you trim a position?
(39:35) There are SO MANY COMPANIES! Why surface area matters.
(43:25) Durable vs. brittle revenue and how to tell them apart
(46:15) When it’s time to angel invest outside your fund
(49:04) The panel’s approaches to capital recycling
(57:15) The benefits of co-working “jam sessions”
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Thank you to our partners:
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DISCLAIMER
*All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.
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From brand savant to accidental entrepreneur, with Sophia Amoruso
From founding the viral fashion brand Nasty Gal to inspiring and living the #Girlboss movement, Sophia Amoruso’s ideas tend to catch fire quickly. She joins host Jeff Berman to share her “accidental” entrepreneurial journey – building an e-commerce brand with nearly $100 million in revenue and then starting Girlboss Media – all with no formal business training. Now, Sophia is focused on supporting and teaching a new generation of entrepreneurs, as Managing Partner of the early-stage venture fund, Trust Fund, and the online community Business Class.
Listen to our episode with Liquid Death's Mike Cessario: Apple & Spotify
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NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso
In this new episode Steven sits down with serial entrepreneur Sophia Amouroso.
Sophia Amouroso is an American business woman and New York Times best-selling author of ‘#GIRLBOSS’ which later became a Netflix series of the same name.
Sophia founded the female fashion retailer, ‘Nasty Gal’ in 2006 when she was 22 years old. 6 years later, Nasty Gal was named the "Fastest Growing Retailer” in America. However, in 2016, the same year that Sophia was named by Forbes as one of the richest self-made women in the world, Nasty Gal filed for bankruptcy.
Since Nasty Gal’s bankruptcy Sophia has founded ‘Girlboss Media’, an online community providing mentoring and support for women worldwide. As well as ‘Business Class’, a comprehensive tutorial course that helps founders accelerate and scale their businesses.
In this conversation Sophia and Steven discuss topics, such as:
How Sophia’s rebellious nature helped her to create an original business
How she regards being an outsider as a superpower
Why as a CEO you only know 10% of what is happening in your company
Why Sophia would never want to be a CEO again
You can follow Sophia here:
Instagram: instagram.com/sophiaamoruso
Twitter: twitter.com/sophiaamoruso
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https://beacons.ai/diaryofaceo
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Sophia Amoruso on branding, raising a fund, portfolio construction & more | E1684
Sophia Amoruso, Founder and GP at Trust Fund, joins Jason to discuss her angel investments (1:23), raising a fund publicly (5:54), and the creative process (12:14). Then, they discuss portfolio construction and putting past identities to bed (27:04).
(0:00) Molly kicks off the show
(1:23) Previous angel investing experience
(5:54) Why Sophia is raising a public fund
(10:45) Linode - Apply to Linode's Rise program for up to six figures in discounts at https://linode.com/twist
(12:14) Branding and the creative process
(20:55) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(22:25) What stage of investing is Sophia going after
(27:04) Portfolio construction
(37:16) Brilliant.org - Go to http://brilliant.org/twist to start your 30-day free trial today and get 20% off your annual premium plan
(38:44) Pro rata rights
(46:56) Putting past identities to bed
(1:01:18) Fund cycles
(1:05:17) Investing in founders or investing in ideas & more
FOLLOW Sophia: https://twitter.com/sophiaamoruso
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
#72 with Sophia Amoruso - GIRLBOSS
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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The power of online communities and healthful habits
In this episode of Product Hunt Radio, I'm in the sunny hills of Los Angeles at the home of Sophia Amoruso with Suzy Ryoo.
Sophia Amoruso is an incredible entrepreneur who I've gotten to know over the past year. She got her start very young, when at 22 she founded NastyGal, selling vintage clothing on eBay. It turned into a massive company with hundreds of employees, until a decade later the company filed for bankruptcy. She's the author of the New York Times bestseller #GIRLBOSS and more recently founded Girlboss, a company focused on bringing together and helping women professionals. They put on community events, publish a daily newsletter and host a wildly popular podcast.
Suzy Ryoo is a very special person to me (full disclosure: She's my SO). We met at Coachella in 2015 just before she transitioned her career from entertainment and media to venture capital. At Atom Factory, she works with entrepreneur, artist manager, and investor, Troy Carter. They manage the Prince Estate and are investors in companies like Lyft, Uber, Warby Parker, Spotify, and Girlboss. She is also a partner at Cross Culture Ventures, a seed stage fund in Los Angeles.
In this episode we talk about:
The best tools and techniques we've used to build healthy habits, whether it's getting more exercise, meditating more frequently (even for five minutes at a time) or just having a calmer mind. We also talk about the ways that being part of a non-judgmental online community — yes, those do exist online — can help everybody involved reach their goals.
Sophia talks about her journey as an entrepreneur, including building a huge company like Nasty Gal “by accident” and the lessons she's taking from her time at Nasty Gal as she starts Girlboss, which, as she likes to say, is the first company she's started “on purpose.”
Why Suzy is still a power user of location-based check-in apps like Swarm and Foursquare. We also talk about some of the unappreciated merits of what sometimes seem like “creepy” products.
The ups-and-downs of investing, and why sometimes you can make a sound decision at the time that you later come to regret.
Of course, we also chat about some of their favorite products, including a $40 (!) astrology app, apps that promise “a vacation for your mind,” as well as startups that deliver the best vitamins and probiotics.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Also, big thanks to our sponsors, Airtable, GE Ventures, Intercom and Stripe for their support. 😸
Quotes from This Episode
“Platforms can become really huge, but when you have a community and there's a sense of context around what they’re talking about and what they’re there to do, ultimately if they help one another, then that's as good as the internet gets.” — Sophia
“Twitter can be like a dialog with yourself, especially if you don’t have a following. I promised myself that I would tweet every time I run, and little known to me, during 2017 I ran 200 miles. I think that feedback loop really helped me.” — Suzy
“I like to say that I’ve started two brands on accident but this is my first business I've started on purpose.” — Sophia
“Like my dad says, 'health is wealth!'” — Suzy
“You don’t really count the places you go in real life, but then you do it digitally [via check-in apps like Foursquare] and you’re like wow, I do a lot of stuff!” — Sophia
Companies and Products Mentioned in This Episode
Bird — Enjoy the ride — quick scooter hires for city commutes.
Complete — A community-based to-do app. Help each other GTD.
Co-Star — Hyper-personalized astrology.
Evernote — Note taking gets even simpler.
Fair — Get a car right on your phone and return it whenever you want.
1st Dibs — It's like Fab for the 1%.
Foursquare — Find the best places everywhere.
Girlboss — A new media site for women.
Headspace — Meditation made simple in just 10 minutes a day.
Highlight (RIP) — Find friends and new people nearby.
Hi Hello — Exchange contacts, seamlessly.
Lime — Rent bikes, e-bikes and e-scooters.
Nike+ Running — Track your runs.
Polymail — A simple, beautiful, and powerful email client for Mac.
Ritual — Reinventing the vitamin, delivered monthly.
Sanctuary— Free daily horoscopes for the cosmically curious.
Seed — Your daily probiotics + prebiotics for systemic health.
Simple Habit— Meditation for people who never have time.
Swarm — Keep up and meet up with your friends.
Tesla — The mass market electric car.
TimePassages — Astrology tools at your fingertips.
Trello — Organize anything, together.
Uber — Get a ride in minutes.
Universe — The easiest way to make an awesome website. From your phone.
Wonderschool — Airbnb for preschools and child care.
#112: The Nasty Icon of Retail, Sophia Amoruso
Sophia Amoruso (@Sophia_Amoruso) is the Founder and Executive Chairman of Nasty Gal, a global online destination for both new and vintage clothing, shoes, and accessories. Founded in 2006, Nasty Gal was named “Fastest Growing Retailer” in 2012 by Inc. Magazine, thanks to its 11,200% three-year growth rate. Sophia has been called "fashion's new phenom" by Forbes magazine, and she has become one of the most prominent and iconic figures in retail. She recently founded the #GIRLBOSS Foundation, which awards financial grants to women in the worlds of design, fashion, and music. Sophia's first book, #GIRLBOSS, is a New York Times bestseller published in fifteen countries. Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is brought to you by Athletic Greens. I get asked all the time, “if you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. Get 50% off your order at Athletic Greens.com/Tim. This podcast is also brought to you by Vimeo Pro, which is ideal for entrepreneurs. In fact, a bunch of my start-ups are already using Vimeo Pro. WealthFront uses it to explain how it develops personalized investment portfolios. TaskRabbit uses it to tell the company’s story. Twitter uses it to showcase Periscope. Why are they using it instead of other options out there? Vimeo Pro provides enterprise level video hosting that typically costs thousands of dollars for a tiny fraction of the cost. Features include: Gorgeous high-quality playback with no ads Up to 20 GB of video storage every week Unlimited plays and views A fully customizable video player, which can include your company logo, custom outro, and more You get all this for just $199 per year (that’s only $17 per/mo.) There are no complicated bandwidth calculations or hidden fees. Just go to Vimeo.com/business to check it out. If you like it, you can use the promo code “Tim” to get 25% off. This is the deepest discount you will find anywhere for Vimeo Pro.
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