Skipper has watched the same pattern play out hundreds of times: teams building products based on assumptions/bias instead of evidence. Talking to customers feels like it’ll slow things down, so they skip it. And more than six (6) months later, they've burned $120–240K on features (or a whole product) nobody wanted.

He helps early-stage startups break that cycle with the Bullseye Customer Sprint — a five-week process combining structured customer interviews with positioning work that gives founders clarity on who adopts first and why they'd choose you. Beyond the Sprint, he works with teams on ongoing coaching, product strategy, design, workshop facilitation, and follow-on weekly customer interviews. No prescriptive answers. Instead, real-life conversations that validate what humans actually need and want.

He's applied this approach previously as founding designer at Sesame (NYC Digital Health 100) and product lead at Shep, acquired by a $1.8B travel management company — he's actively working with another early-stage team through their path to exit. He's also consulted with Fortune 50 firms through Fjord, thoughtbot, and SoftServe. Through How This Works co and The Consulting Lab, he helps early-stage and scaling companies get customer clarity right. He also hosts the How This Works show.

He studied playwriting and English literature (not business school or design school), which taught him the most compelling story needs clarity and heart. He specializes in unblocking teams and creating space for people to do their best work without burning out.

Sweet spot: founders with early users or seed funding. Product-market fit and timing need to be as much in focus as possible before you scale.

Based in the Bay Area, he speaks — and writes — English fluently, five (5) other languages poorly.