Tales of a Serial Entrepreneur

Part 1: My Three Biggest Mistakes

While there are ways to be a happy, healthy, financially sustainable entrepreneur, there are infinitely more ways to be a stressed-out, anxiety-ridden, cash-strapped entrepreneur. And I, not knowing what I did not know, have definitely looked back at some of my choices and said, “Well, that was idiotic…”

Part 2: The Seven Choices That Changed My Life

I’ve suffered through three bouts of depression, experienced severe financial instability, and continue to have friends and family who still don’t understand, much less respect, what I do. I’ve made more mistakes than I could possibly ever count. And yet, I am happier now than I have ever been. While I don’t have all the answers, I do know that I have made choices, intuitively at first, but now intentionally, that have helped me survive, and now thrive, as a serial entrepreneur.

Part 3: The Only Woman in the Room

“Wow, that’s a strong handshake.”

It’s June 23rd, 2014, a short two weeks after Tricia Douglas and I co-founded Nexus Works. We’re meeting the folks at a particular startup accelerator for the first time. In attendance are the Executive Director and one of the accelerator’s mentors. The first thing that mentor said to Tricia was, “Wow, that’s a strong handshake.”

Part 4: Racists Don’t Exist, Racism Does

As an entrepreneur, you’re building scalable organizations that have the potential to impact millions of people around the world. These millions of people do not all look alike, act alike, nor think alike. Instead, they are all different and unique in their own beautiful ways. Your organization cannot, will not grow if you do not build empathy for those who are different from you.

Part 5: How to Build a Safety Net When You’re Born Without One

We need people from the most disadvantaged backgrounds to have safety nets because we need entrepreneurs who are compelled to solve problems they themselves have experienced. Problems that, when solved, will lead to true liberation.

Part 6: I Feel Your Pain

A fellow education startup founder once asked me, “Why do you do what you do?”

I answered, “When I see other people in pain, I feel that pain, too. When I solve for my own pain, I take it upon myself to solve that pain for everyone else as well.”

The work of an entrepreneur is to recognize pain where others don’t and to create solutions where others merely compensate. Entrepreneurs use their empathy to create solutions that work, not only for themselves, but for others as well.

Part 7: Start With Your Core Beliefs

I meet with at least two new early stage founders every week. Whenever I do, I start by asking them

“What are your core beliefs?”

“What do you mean?”

“Well, I mean…

Who do you serve?
What problem are you trying to solve?
What values guide your decisions?
What is your vision of the future?
What kind of life do you want to build for yourself?
What are your superpowers?”

Part 8: I Grew Up Poor in a Rich Person’s World

I stopped asking for presents at age 8. That’s when I understood that my family was poor, and that I couldn’t ask for much, because the answer would be “No.”

Part 9: Coming Out as Bipolar

My therapist thinks I’m crazy for writing publicly that I’m bipolar. Well, she thinks I’m crazy in general, but then again, that’s why I see her. Everyone, though, is crazy in their own way. In fact, it’s perfectly normal to be crazy. The only question is what form your crazy takes.


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