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).