Episode Details

He cold-called American trucking companies from a dark office in Auckland at 2am — New Zealand accent and all — and built a nine-figure SaaS exit out of it.

In this episode of 2 Commas, I sit down with Tim Boyle, co-founder of Whip Around, to unpack what it really takes to go from a commercial real estate career and a half-baked idea to a fleet compliance platform operating across the US with thousands of customers. We talk about the accidental pivot to DVIR compliance that changed everything, the decision to plant their sales team in Charlotte, North Carolina, and how they scaled from $1M to $10M ARR in roughly two years.

Tim also gets honest about the harder stuff — being voted off the board of the company he started, the structural mistakes that made it possible, and what he'd do differently from day one around founder rights, cap tables, and governance. He's remarkably at peace with how it all played out, and the lessons he's carrying into his next venture, HelpGenie, are worth the listen alone.

We finish on the exit: what a nine-figure acquisition actually looks like from the founder's seat, why getting to a finish line matters beyond the dollars, and why Tim thinks the old-school ways of building customer trust are about to come back in a big way.