Some stories follow you through your whole life. My grandmother, Esther “Betty” Warner Cleveland, is one of mine.
She earned her pilot’s license at just sixteen—at the time, the youngest licensed pilot in the State of California. Her uncles, both Army Air Corps veterans, trained her in an Alexander Eagle Rock biplane they’d converted from a World War I fighter into a trainer. It’s the kind of origin story Hollywood would overplay, but she lived it without a trace of drama.
There’s a black-and-white photo of her standing beside that biplane. It hangs on my wall now. Every time I pause in front of it, I wonder what she was thinking in that moment—wind in her hair, hand on the wing, ready to lift into a sky most young women were never invited to enter. Whatever it was, it carried a quiet conviction. A belief that she belonged up there. A belief that courage is an everyday verb.
She never bragged about being a trailblazer. She simply learned to fly, and then moved on to the next thing that needed doing. She taught piano in her home, hosted student recitals in her living room, and shared music with families who still remember her. Long before entrepreneurship was a buzzword, she built a life around service, creativity, and self-reliance.
And she was a maker through and through. She canned fruits and vegetables by the hundreds of jars. She spun wool. She shaped clay. She worked with her hands the way some people breathe—naturally, generously, endlessly curious. Sitting beside her, I learned that usefulness and beauty don’t have to compete. They can come from the same set of hands.
That spirit carried through to my dad, a pilot himself, who insisted I learn enough to take over the controls of his Piper Cherokee if I ever had to. I didn’t go on to earn a pilot’s license, but I did end up earning my Class C parachutist’s license—over 170 jumps, leaping with joy out of perfectly good airplanes. People sometimes ask me why. The truth is simple: adventure runs in our family. It’s heritage.
What my grandmother taught me is that adventure isn’t about chasing adrenaline or taking reckless risks. It’s about believing you can step into something bigger than you’ve known—and doing it with a steady heart.
Her life continues to shape mine. Her grit, her curiosity, her kindness—they’re baked into the way I build companies, raise teams, and navigate uncertainty. She showed me that the real legacy we leave isn’t the trophies or titles. It’s the courage we model. The creativity we practice. The quiet confidence we pass down without ever needing to say a word.
Her wings still lift us.
