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

Money that arrives fast doesn't fix you. It finds out who you already are.
Everyone assumes building real wealth takes twenty years. These three founders didn't wait. Seeby Woodhouse registered Orcon for $29.85 at nineteen, doubled it every year for nine years, and exited at twenty-nine, then spent $18 million on property six weeks before the GFC. Keith Davison failed at five companies before Cloud Conformity went from nothing to a $120 million exit in under two and a half years, with no founder taking a salary for most of them. Joshua Parsons was a cop at seventeen, cleaning pools at twenty-seven, and had built and sold two companies by his early thirties. This best-of episode is three honest accounts of fast money and what it costs.
We get into:
Seeby doubling his company every year for nine years straight
Why Keith took zero salary for two and a half years before a $120m exit
How Joshua learned to sell as a cop before he ever ran a business
What Seeby did with millions at twenty-nine and the GFC lesson that followed
Why all three say the money was the start of the hard part
Getting rich young is a skill nobody teaches you how to survive.
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Dom Sutton hired three general managers to run the business he built. Two didn't work out, and he owns most of the reasons why.
Dom started Pumpt with his last paycheck, running cold calls from a tiny room next to the toilet while his two boys slept on a mattress beside his bed. He grew it into an advertising business putting 70 million items into NZ letterboxes a year. This is an unusually honest conversation about the founder-to-owner transition, the difference between delegating and abdicating, and why the lack of the right metrics let good months quietly slide into losses. He also tells the story of the toy business he bought on a lick-of-paint story that lost him a dollar a minute for two years, and how that exact disaster became StockTrim, the inventory forecasting software he now sells in 26 countries.
We get into:
Why two of his three GM hires failed and what he'd do differently
Delegating vs abdicating, learned the hard way
The $1.2 million toy business mistake and the due diligence lesson behind it
How that failure became a global SaaS
Why he walked away from selling Pumpt before finally exiting to his own GM
Sometimes the business you build next comes straight out of the one that nearly broke you.
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81 days from "I think I want to sell" to the money clearing. No broker. No lawyer. Dr. Michael Filosi did the whole thing himself.
He sold the largest dental practice in Adelaide to private equity at 41, at a multiple well above the industry norm. Ten years earlier he'd bought it with a possum living in the wall, two chairs, and pen-and-paper appointment books, the practice nobody else wanted. He saw the busy patient base underneath the mess, took it from worst to first, and built it into a genuinely sale-ready business. That's why, when he finally decided he'd had enough, it sold at warp speed.
We get into:
Why the sale moved in 81 days when most deals take months
The buy-in structure that locked his purchase price years in advance
What frictionless actually means to a buyer, and how he engineered it
Why he refused to let private equity condition him down on price
The four Ds model he used to get out of the chair and design the business
Build it to sell long before you ever want to, and the exit takes care of itself.
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$100,000 in year one. $10 million by year four. When people ask Sarah Page how she did it, her answer makes them uncomfortable. She did nothing else.
Sarah is the founder and CEO of The Kindness Collective and the 2024 New Zealander of the Year for community work. What began as a car full of pantry cans driven to a woman's refuge during the darkest period of her life is now a charity supporting over 130,000 New Zealanders a year. This is a genuinely honest conversation about total focus and what it costs. Sarah has ADHD, which she's reframed from a source of shame into her greatest asset, and she's candid about the parts most founders won't touch: the brutal shift from founder to CEO, learning to give up control, and being told she's too much.
We get into:
Why doing nothing but the one thing scaled the charity so fast
How ADHD makes founders 400 times more likely to start something
The founder to CEO identity shift and why it nearly broke her
Learning to hand control to a board smarter than her
The charity misconceptions that cost real people real help
The intensity people find uncomfortable is the same thing that built it all.
📩 Subscribe to the 2 Commas Journal → https://www.joshcomrie.com/subscribe
📖 Order the 2 Commas book → https://www.joshcomrie.com/2-commas-book-order
👤 Follow Josh on LinkedIn → https://www.linkedin.com/in/joshcomrie/
🔗 Connect with Sarah Page → https://www.linkedin.com/in/sarahpagenz/

Rich Conway spent hundreds of thousands of dollars proving he was hiring the wrong salespeople. He was wrong about that too.
He was bringing in good people, then setting them up to fail with no systems, no metrics, and no structure to succeed. When he finally hired a sales manager who put that scaffolding in place, the same calibre of people started producing straight away. It's one of the more honest leadership admissions you'll hear from a founder. Rich is an introvert with imposter syndrome who built Pure SEO into the number one search agency in New Zealand, arriving here in the depths of the GFC with no friends and no family. He refused to guarantee Google rankings when every competitor did, nearly went under, then watched the market swing his way.
We get into:
Why his best salespeople on paper kept failing and what he owned about it
The systems that turned the same people into producers
The emotional call to let go of his best mate, who he'd hired as GM
Two exit processes that fell over and why he's glad they did
How he rebuilt the whole business around AI search
Sometimes the hire isn't the problem. The setup around them is.
📩 Subscribe to the 2 Commas Journal → ⁠https://www.joshcomrie.com/subscribe⁠
📖 Order the 2 Commas book → ⁠https://www.joshcomrie.com/2-commas-book-order⁠
👤 Follow Josh on LinkedIn → ⁠https://www.linkedin.com/in/joshcomrie/⁠
🔗 Connect with Rich Conway → ⁠https://www.linkedin.com/in/pureseo/