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Sophia Amoruso
Investing in winners at Trust Fund, NYT Bestselling Author, Serial Founder, Keynote Speaker. Returned the dress I wore on the cover of Forbes. 💸 Pitch us at trustfund.vc 💸
Sophia Amoruso is the Founder & Managing Partner at Trust Fund, an early-stage venture fund focused on pre-seed and seed stage companies.
In 2020, Sophia founded Business Class, a comprehensive 10-week digital course for entrepreneurs, creatives, and freelancers, which has built a community of over 3,000 founders across the globe.
In 2017, Sophia founded Girlboss, a community for ambitious women. Sophia also hosted podcast Girlboss Radio from 2015-2020, which garnered over 20 million downloads. In December 2019, it was announced that Girlboss had been acquired by Attention Capital.
Her 2014 New York Times Bestseller #GIRLBOSS, which chronicled her early life as well as her experience as the founder of fashion empire Nasty Gal, was adapted into a scripted TV series that premiered on Netflix in 2017 and was produced by Charlize Theron. Sophia has also authored two other books: Nasty Galaxy and the Girlboss Workbook.
Sophia made her mark when she founded Nasty Gal in 2006 and bootstrapped it to $28 million profitably, raising $60 million in venture capital and scaling the business to over $100 million in revenue. Sophia became a member of the CFDA in 2016.
Sophia has been featured on the cover of Forbes magazine's 2016 America's Richest Self Made Women issue and featured in the Fortune 40 under 40, Forbes 30 under 30, Inc. 30 under 30, and Fast Company’s Most Creative People in Business lists.
Highlights
If you're a founder or early employee, this post could put a few million (or a hundred million) in your pocket.
One of my portfolio companies is raising a Series A, and the founder just reached out to me to ask whether they needed to consider any personal financial planning. That's when QSBS trust stacking came up.
You've likely heard of trusts. You're less likely to have heard of QSBS.
QSBS trust stacking is one of the single most powerful tax-savings tools founders and early employees can take advantage of.
QSBS (Qualified Small Business Stock) is a US tax rule designed to reward early risk-takers by allowing founders and early employees to shield up to $10M of startup gains from federal capital gains tax.
Let's do the math. Same company, same exit. Two different founders.
Founder A
- Exits for $50M
- No trusts. No stacking.
- Only $10M qualifies for QSBS.
The remaining $40M is taxable.
At ~40% combined taxes, that’s roughly $16M gone.
Founder B
- Same $50M exit.
- Set up 4 QSBS-eligible trusts early, each holding $10M of founder shares.
Each trust gets its own $10M QSBS exemption. That’s $40M tax-free.
Founder B just kept ~$16M more, without changing the business or the outcome.
This only works if the stock is issued early (before the company’s assets cross ~$50M). That’s why this has to be done before Series A, not after success feels guaranteed.
This is how wealthy founders structure their equity.
https://t.co/VGhvQSif9H (another Trust Fund portfolio company) was founded by @SandroChess and fellow early members of the Carta team to digitize trust creation and stacking. Dynasty sets up, funds, and maintains QSBS-eligible trusts with ongoing compliance so founders and early employees can capture $10–$15M per beneficiary at exit.
The biggest mistake with QSBS isn’t doing it wrong.
It’s learning about it too late ⌛
Damn! When you put it that way! I’m blushing ☺️
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Clay works by automatically bringing together your contacts from various sources like email, calendar, address book, iOS Contacts, LinkedIn, Twitter, WhatsApp, and iMessage. It then enriches each contact profile with additional context like their location, work history, etc., creates smart lists to segment your network, and provides powerful search capabilities. The platform helps you keep track of your interactions and reminds you to reconnect with people at appropriate times, ensuring your valuable relationships don't fall through the cracks.
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