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

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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Connect with Dr. Michael Filosi on LinkedIn

$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/

Most founders sell a business once, with no idea what they're doing. Shivani Gupta refused to go in blind.
Before she sold her wellness business, Shivani tracked down more than 20 founders who'd already exited and asked every one of them the same questions. What did you sell for, did you use a multiple of EBIT, what would you do again, what would you never do again. She put every answer into a spreadsheet, found the three lessons that came up most often, and applied all three. It added 25% to her final sale price, with no broker. A former electrical engineer who left corporate life after a trip to Nepal, Shivani had already built the business to 10X and exited at 11X. This conversation is the closest thing to an exit strategy masterclass you'll get from someone who taught herself the whole thing.
We get into:
The research process that added 25% to her exit
Why squeezing every line item flows straight through to your valuation
Why she turned down a higher offer that would not give her staff contracts
How she brought her key leaders inside the sale rather than hiding it
The scaling mindset she now uses to help founders think past incremental growth
The best time to learn how to sell a business is long before you have to.
📩 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/