2 Commas: The $multi-million exit show with Josh Comrie

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.

He pre-sold a SaaS product for $150 before it even existed — then discovered it was harder to sell the real thing for $30/month once customers could actually touch it.
In this episode of 2 Commas, I sit down with Yuan Wang, co‑founder of Studio Ninja, to unpack what bootstrapping really looks like when you choose customers over investors. We talk about the early crowdfunding-style pre-sell (including taking card payments over the phone), the painful first launch that landed with silence, and the rebuild that came from obsessive customer feedback and iteration.
Yuan also breaks down how Studio Ninja grew from a niche tool for wedding photographers into a global platform across 70+ countries — driven by SEO, community, and “hero photographers” who became unofficial ambassadors — before eventually being acquired by ImageQuix. We finish with the exit side: what inbound acquisition interest actually looks like, why they turned down an early life-changing offer, and how to keep growing the business while the deal noise swirls in the background.

Most founders think selling a business is a transaction. Find a buyer, get a multiple, sign the papers. In reality, it’s an identity shift, a relationship test, and a stress event that shows you what your company is really made of.
In this episode of 2 Commas, I sit down with Vivian Bryant‑Taukiri, founder of Brand Spanking, to unpack what it takes to build and scale an experiential marketing agency over 20+ years, and then exit it cleanly. We talk about the shift from “promo girls in Lycra” to modern brand experience, why this is ultimately a people-and-problem-solving business, and how mergers, acquisitions, and COVID pressure-tested everything.
This is a practical conversation about partnerships, agency growth, and the reality of selling a service business. You’ll hear what triggered the sale, why a simple offer beat complicated earnouts, and why the most underestimated part of an exit is learning how to sit still after the thing that once defined you is gone.

Most founders hear “AI” and think they get it. Smarter emails. Faster content. A few basic automations. In reality, that’s a jet engine being used as a desk fan, and it creates a dangerous illusion of progress.
In this episode of 2 Commas, I lay out why 2026 is a once-in-a-generation land grab for Western businesses, and why “power is never given, only taken”. I share the moment that snapped this into focus for me, the traps that keep smart operators stuck (the free-tier trap and the tool-shopping trap), and the real shift that’s happening right now: from assistant to agent, where AI stops answering questions and starts running multi-step workflows.
This is a practical call to arms. You’ll leave with a simple three-step approach to take action this week: pick your most expensive recurring problem, define what “solved” actually looks like with a measure attached, then choose one tool and build one workflow end-to-end. Not this quarter. This week.
Download the Whitepaper here 👉 https://www.joshcomrie.com/2026

Founders often think they can tidy things up when it’s time to sell. In practice, the value is won or lost earlier—depending on how much complexity, weak infrastructure, and preventable errors are allowed to accumulate.
In this episode of 2 Commas, I sit down with Jeremy Moon, founder of Icebreaker, to unpack what it takes to build a global brand from New Zealand and then execute a successful acquisition. We cover international expansion, why the “New Zealand advantage” is often a myth offshore, and why hiring local teams matters more than most founders expect.
Jeremy also breaks down scaling and profitability, how brand shows up in gross margin, and what changed when he brought in Rob Fyfe as CEO to professionalise the business. We get into exit planning, sale readiness, the M&A process, and how to position a company so it attracts premium buyers and stronger valuation multiples.