She was asking people if they wanted Botox before most New Zealanders knew what it was, and they were asking her if their face was going to fall off.

Dr. Catherine Stone pioneered cosmetic medicine in New Zealand in 2001, set up her first clinic in Vulcan Lane for $13,500, and built one of the country's most recognised aesthetic brands from scratch. In this episode of 2 Commas, I sit down with Dr. Cat to unpack what it looks like to front-run a trend before anyone believes in it, build a high-end boutique in a space that didn't exist, and scale it through TV deals, London clinics, and a few very well-timed pivots.

We also get into the stuff nobody talks about - buying 23 properties in 24 months right before the GFC, the burnout that nearly ended everything, and three separate cancer diagnoses that ultimately forced the question: what actually matters? The answer led to an eight-week exit to someone she trusted, not the biggest multiple on the table. If you're building something and wondering what it looks like to lose nearly everything, rebuild it bigger, and walk away on your own terms. This one's worth your time.

Rafael Niesten built a nine-figure exit, woke up at 5:30am to watch the money land, and celebrated by going to Indian for $62 and buying three USB-C cables.

In this episode of 2 Commas, I sit down with Raf, founder of PropTech Labs, to unpack what it actually looks like to build, acquire, and sell a portfolio of PropTech businesses without an investment banker in sight. We cover three strategic acquisitions in 18 months, five months of due diligence with a giant US corporate, and why timing the market ended up mattering just as much as building the product.

We also get into the exit psychology - the void that opens up after a frenetic decade, the "one-eyed dog in a meat factory" focus lesson that changed everything, and what Raf's doing with the freedom on the other side. If you're building something and wondering what the finish line actually looks like and what comes after it, this one's worth your time.

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.