A newsletter for people who work for themselves (or want to)

I've moved to Substack.

I wrote last week’s newsletter from Big Sur, California, saying I was about to fly back to London. Instead I took a hard left (right?) and found myself in the remote fishing town of Guriú on the northeastern coast of Brazil. This update is super on theme, so keep reading to find out why.

When I hit 40 in April, I found myself inspired to upend everything about my life: the city I call home, the places I work, who lives in my house (not me!), whose house I live in (not mine!), how often I travel (hint: it’s a lot), and who I’m (mostly not) dating. 

So, I thought, why not do the same with this newsletter?

I’m too impatient to bury the lede on this, so I’ll get straight to the point:

This newsletter has a new home on Substack, with better access to me and over 100k entrepreneurs and creatives.

If you’re just finding me for the first time today, let me briefly introduce myself: I'm a misfit community college dropout from Northern California. I started selling vintage clothing on eBay when I was 22, called it Nasty Gal, and eventually scaled the business to over $100 million in annual revenue. Then I wrote an 18-week New York Times Bestselling book about it called ​#GIRLBOSS​ that sold 500,000 copies, and was adapted into a​ Netflix series​ (weird!) produced by Charlize Theron (weirder!). 

In 2020, I launched a digital course and membership called Business Class, where I teach entrepreneurs how to build businesses. It’s a pretty massive program, with over 8 hours of lessons taught by yours truly, 100 hours of video trainings, and 300 pages of worksheets to work through.

Over the years, I rather accidentally became an angel investor, writing over $1m worth of checks into over 20 companies like 1stDibs, Liquid Death, Eight Sleep, Therabody, Ceremonia, and Kindbody. From this, I realized I had great access to deals and loved helping founders. 

So in 2022,  I decided to raise a venture capital fund called Trust Fund. Since then, I’ve invested in 14 early-stage software companies (see the full portfolio here), and have found the support of legendary backers like Marc Andreessen, Jason Calacanis, David Sacks, Paris Hilton, Andrew Chen, Jeff Jordan, Jeremy Liew, Ev Williams, Anthony Noto, Sam Parr, Andrew Wilkinson, and Codie Sanchez, to name more than a few.

When I launched this newsletter earlier this year, it was to share not just my own expertise and experience, but learnings from the fascinating people I know and continue to meet, insider knowledge I’m privy to, founders I’m inspired by, news that’s relevant to you, and, as someone who still considers herself an outsider, my oblique view of it all. 

Over the past several months, the engagement has become more and more pronounced. Dozens of readers began writing in each week, sharing their thoughts. It began to feel like a community. And Substack is where newsletters become communities.

Free subscribers will continue to get occasional free posts.

Paid subscribers are about to get a whole lot more, including…

• A regular roundup of the most relevant news for people who work for themselves (per my reader survey, that’s you, or soon-to-be-you!) on the topics of entrepreneurship, money, social media, marketing, cultural trends, and style – and the ability to share your commentary with the reader community

• What my buds in biz are buzzing about, and their insider perspectives

• Live interviews with cool founders, marketers, finance bros, creatives (kind of like a podcast without committing to the word podcast, and an excuse for me to learn for an hour, but broadcast to you too!)

• Regular updates on my increasingly weird life (investing in audacious ideas, relocating poodles across the planet, dates with 24 year-olds, etc. etc.)

• Community features, including live chat, the ability to connect with other readers, start your own threads, and weigh in on the week’s topics. Like a 24/7 chat room for the coolest people in business. 

You can subscribe now for $8/mo or $58/year, which is 40% cheaper than paying monthly.

Exclusive to paid subscribers, I’m kicking off this new era with a series of live video chats with Trust Fund’s portfolio of founders. Tomorrow, October 3 at 5pm ET, I’ll be chatting live with Megan Duong, co-founder at Plot, the creative management platform for fast-moving content teams, with customers like Tory Burch, Staud, and La Roche-Posay.

We’ll chat about…

• How Megan got the idea for Plot, and how she convinced heavy hitters like Alexis Ohanian (and me!) to invest (especially as a first-time founder)

• How she listened to customer feedback, iterate on the product, and what she’s built around their needs

• What it’s like to build software without engineering experience

• The deep insights she’s gleaned having worked with dozens of brands, both big and small on their social media strategies 

Drop your questions for Megan in the chat:

See you there!

Wheels up,

Sophia