What does it take to build a life that feels like your own? Sometimes it looks like chasing opportunity, sometimes it looks like falling flat on your face, and sometimes it’s as simple—and as complicated—as choosing to live authentically.
Today, I had the joy of sitting down with my neighbor and friend, Danielle. We first met over wine and deep conversation, and I knew instantly she was someone special—someone who could ask hard questions, laugh easily, and live with a kind of fearlessness I deeply admire.
Her story is wild, brave, and layered. From growing up on a farm in Illinois to launching a sunglass empire on the early internet, from carrying $50,000 of debt at 18% interest to negotiating million-dollar deals in New York, and then stepping fully into her truth as a transgender woman and comedian—Danielle has lived more chapters than most of us could imagine.
And yet, the thread running through it all is simple: persistence, humor, and the courage to be real.
Key Themes + Takeaways
How growing up on a farm shaped Danielle’s work ethic and resilience
The highs and lows of building a business from scratch (and nearly losing it all)
Why diversity and authenticity make organizations—and people—stronger
The surprising lessons comedy teaches about trust, fear, and connection
What it really means to live bravely and embrace your story
Our Favorite Quotes
“I learned early on—don’t bet the farm. If the worst that can happen is people don’t laugh, then maybe that’s exactly what you should try.”
“I lived 50 years in the closet because I couldn’t afford to be authentic. Money was my security blanket. But once I let that go, I found freedom.”
“The diversity made us stronger. I still don’t understand why more people can’t see that.”
“Sometimes bravery is just asking: what’s the alternative? And then choosing to keep going.”
“There are really only two ways to change someone’s mind—be their trusted advisor, or make them laugh.”
Chapter Markers
00:02:44 Meeting Danielle – wine, hard questions, and instant connection
00:04:01 Farm life: danger, grit, and freedom before cell phones
00:07:11 The first failed business and $50,000 in debt
00:17:09 Discovering the internet—and the first online sunglass sale
00:29:01 Negotiating domain names, growth, and big deals
00:35:11 Venture capitalists, big checks, and big crashes
00:44:33 Transition, family, and the long road to authenticity
00:47:16 Why comedy: confronting fear and controlling the narrative
00:58:50 Business, lawsuits, and the harder work of comedy
01:12:40 Bravery, diversity, and the freedom of living openly
Your Turn
This week’s reflection: Where in your life are you waiting too long to live authentically? What small step could you take—today—that would move you closer to the life you know is yours?
See Danielle Live
Danielle is always on stage, and she’s got some incredible shows coming up:
November 8 – Headlining at Wussow’s in Duluth, MN
November 22 – Performing at Honest Dog Books in Bayfield, WI
✨ The best way to connect with Danielle and see what’s next is through her website: www.xaos.com
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