Episode 9:

How to Be a Successful Serial Entrepreneur: In Discussion With Sophia Amoruso

From Running a Fashion Brand to Building a Media Company to Online Courses and Angel Investing

Just like ClubHouse, sometimes we need invites to the party. Several years ago, Sophia Amoruso invited Morgan to the angel investor party, a place where, unfortunately, women are often excluded from the guest list.

On this episode of WorkSmart, we chat with Sophia – legend behind the brands Nasty Gal and Girlboss – about her journey to entrepreneurship, the un-sexy parts of running a media company, making hard choices after success, and why bringing other women to the party is never a faux pas.

Sophia’s Story

In Morgan’s first round of funding, she faced rejection after rejection from Black venture capitalists. Feeling discouraged, she put her nose to the grindstone and decided to bootstrap her business…until a friend recommended she raise money from social impact investors. 


After her first round of funding, enter Harlem Capital. Harlem was a new venture at the time, focused on helping Black startups. Morgan quickly realized that her vision and Jarrid’s aligned perfectly, so after a memorable business brunch, they took a chance on each other!

An Unwavering Criteria

When you succeed as an entrepreneur, you feel incredibly privileged. So it’s hard to say no to people asking for advice and throwing opportunities your way. While there is a responsibility to pass down knowledge, let’s cut the pressure to accept every email and launch every startup.

Sophia knows what she’ll say yes to versus no and while she (politely) says no to most, that also includes herself. She prefers project-based work for herself and knows she won’t be valuable for every entrepreneur. Even and especially in the early stages of business, be careful what you choose. Because being CEO isn’t something you can easily turn off.

Extending The Invite

The world of angel investing is still pretty new for Morgan and, without Sophia, who knows when she would have entered the game that guarantees wealth for many of its entrants. While it’s important to prioritize, it never takes long to pull up a seat for women at the table.

Homework Time

No matter where you are on your entrepreneurial journey, write out your personal decision-making criteria today. Knowing what you’ll say yes to is just as important as determining what you’ll decline. And remember to be unwavering! Your time is valuable and you should have the freedom to spend it how you choose.


Remember: work smarter, not harder.

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Angel Investor

Someone who invests capital in a start-up in exchange for ownership equity or convertible debt. Angel investors typically invest in the seed stage, giving companies early financial momentum.


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