Bill Kerig is an American entrepreneur, filmmaker, and author. His peripatetic career through sport, print, film and tech is united by one simple question: I wonder if I can? He asked it about becoming a pro skier , writing for a living, making movies and magazines, as well as creating and running tech companies. And every time he asked, he was answered by a chorus of Hell, No. You can’t. The naysayers only served to fill his fuel tank. Today, he’s taken some 19 companies, films, books, and magazines from concept to market to exit.

And as he gotten older, he’s become bolder.

Although he’d owned and ridden motorcycles his whole life, the world opened up for him when his children dragged him into dirt biking at age fifty. Taking motocross lessons with twelve-year-olds, he found not only humility, but a new and outlandish liberation.

When his sixtieth birthday coincided with crushing professional and personal loss, he turned to adventure motorcycles for the solace and space to find a way through one of life’s most difficult and underrated transitions. In adventure motorcycling he found a metaphor for getting unstuck, for leaning in, for using throttle to clear obstacles, and for loving the wild ride that a risk-embracing life can provide.

Through it all, he’s developed a steady, systematic approach to early- and growth-stage endeavors that minimizes uncertainty and maximizes opportunity while staying forward-focused amidst difficult but predictable challenges. Today, he is working on his twentieth and twenty-first endeavor (a film and a book) and has found a new passion for helping other entrepreneurs answer their own I-wonder-if-I-can questions through his Traction Business Accelerator service.