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

di Josh Comrie

Stagione 5

26 years of Huffer, and what came next | Steve Dunstan | 2 Commas by Josh Comrie

$20 and a fax machine. That's what Steve Dunstan started Huffer with. Twenty-six years later, he'd built one of New Zealand's most recognised streetwear brands, scaled it to around 200 people, survived the GFC, wrestled with a US expansion that didn't go to plan, and lost a co-founder along the way. In this one, Steve is straight about the part founders rarely admit: what happens to your identity when you and the brand become the same thing, what it takes to sell a business you built from the ground up, and how you rebuild yourself once it's gone. We get into: The $20 start and why the constraint helped $35k to over $1m in four years, no outside money Surviving the GFC as a fashion brand Why belonging became the thing that drove performance The exit after 26 years, and what came next Would you know how to stop being the business, the day you finally sell it? Subscribe to the 2 Commas Journal Order the 2 Commas book Follow Josh on LinkedIn Connect with Steve Dunstan

S5 · E29

30 set 2026

1:22:41

Three exits, three very different endings: What fast money does to founders | 2 Commas by 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. Subscribe to the 2 Commas Journal Order the 2 Commas book Follow Josh on LinkedIn

S5 · E28

17 set 2026

54:19

3 X GM's hired but only 1 exit: How I got this wrong | Dom Sutton | 2 Commas by 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. ⁠Subscribe to the 2 Commas Journal⁠ Order the 2 Commas book⁠ Follow Josh on LinkedIn

S5 · E27

9 set 2026

1:11:28

How I went from "I Think I Want to Sell" to the $$ in 81 days! | Dr. Michael Filosi | 2 Commas by Josh Comrie

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. I'm building a community for founders serious about a real exit. Come find out what it's about, Click here to join the FREE Webinar. Follow me on LinkedIn Connect with Dr. Michael Filosi on LinkedIn

S5 · E26

2 set 2026

55:53

$100k to $10 million in four years: The cost of doing nothing else | Sarah Page | 2 Commas by Josh Comrie

$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/

S5 · E25

27 ago 2026

1:16:16

The non-performing salespeople weren't the problem. I was. | Rich Conway | 2 Commas by Josh Comrie

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/

S5 · E24

19 ago 2026

1:15:23

Taking on and beating the giants | 2 Commas by Josh Comrie

The Comma Club is now open for founding members — a private community for NZ founders building toward a multimillion-dollar exit: https://www.joshcomrie.com/club Shane Young flew to Sydney six times to get a single purchase order out of Woolworths. On launch day, he walked into the flagship supermarket to find his product had separated in transit and was leaking yellow puddles across the shelf. Four years of work, and he thought it was over in an instant. It wasn't. This is a special episode of 2 Commas built around one question: what does it take for a small New Zealand business to take on far bigger competitors and win? Three founders answer it from three angles. Shane covers product, and how getting locked out by contract manufacturers forced him to build his own factory and made the business unbeatable. James McGlinn covers strategy, and how Event Finder survived the NZ Government launching a taxpayer-funded competitor by fighting back with a guerrilla Twitter campaign that put the responsible minister on the spot live on Breakfast TV. Cornelius Boertjens covers market, and how raising his prices, building a deliberately annoying presence in Australia, and engineering deal tension between two acquirers turned a niche agency into a Havas exit. We get into: Why Shane's Brisbane disaster became the thing that made his business defensible How James won against a competitor with millions in government funding behind it Why pricing up got Cornelius more demand, not less The modesty penalty that quietly costs NZ founders across the Tasman The annoying itch strategy that makes a giant come to you If you're building something small in a market full of big players, this episode is three different maps for the same territory.

S5 · E23

5 ago 2026

29:38

50 Ferraris, 4 exits and a fight for his life | Grant Baker | 2 Commas with Josh Comrie

The Comma Club is now open for founding members — a private community for NZ founders building toward a multimillion-dollar exit: ⁠https://www.joshcomrie.com/club⁠ Grant Baker was sitting in his office on credit watch with BNZ when his phone rang. Eric Watson was calling from Palm Springs to say he'd sold Blue Star for a hundred million dollars. The deal had been done on a golf course in the dark. Grant thought he was joking. He wasn't. Ninety million came in shares. Six months later, when the lockup expired, those shares had doubled. Blue Star had grown from $2M to $1B in sales through 56 acquisitions and almost no working capital. That was exit one. Then came Empower, an electricity retailer Grant built to 150,000 customers and 10% of all NZ electricity sales before selling to Contact Energy. Then 42 Below, which Jeff Ross was making 500 cases a year of in his garage when Grant got involved, sold to Bacardi for $165M USD on $20M revenue. Then Turners, bought for $70M when Grant's own company was worth $20M, now approaching a billion dollar market cap. Along the way: a bowel cancer diagnosis the morning of his first Bacardi meeting, 50 Ferraris, and a decade backing Liam Lawson from a $4,000 airfare to Formula One. We get into: What 56 acquisitions taught him about what kills a roll-up strategy Why Bacardi paid a technology multiple for a spirits business and what that tells you about brand How to build a business that a specific buyer will have to acquire The cancer diagnosis, the 50/50 odds, and what his father's death three weeks later changed Why he disagrees with "follow your passion" and what he'd tell any young NZ founder If you're building something and wondering what four decades of exits, setbacks, and survival actually looks like from the inside, this one's worth your time.

S5 · E22

29 lug 2026

1:13:40

He’s invested $billions and not taken a single share of equity | Tim Wixon | 2 Commas with Josh Comrie

Tim Wixon has put debt funding into more than 1,700 New Zealand tech companies. He has never taken a single share of equity in any of them. As Head of Technology and Innovation at BNZ, Tim spent 11 years building a lending model most traditional bankers said was impossible. Debt against recurring revenue, interest only while you scale, no personal guarantees, and no dilution. His first deal set the tone: five million dollars to a zero-profit software company buying another zero-profit company, secured only against the software. His colleagues laughed when he said he wanted to fund tech. One deal led to another, and it grew into a portfolio of over 1,700 companies. A former lawyer and FMA regulator, Tim brings an outsider's clarity to how founders should actually think about capital. This is the clearest explanation of non-equity funding you'll hear from anyone in New Zealand. We get into: How BNZ funds companies with no profit, no tangible assets, and no personal guarantees Why interest-only debt while you grow can protect your cap table better than a raise The lead indicators Tim looks for that most founders never track What the SaaS apocalypse did to founder attitudes toward debt in NZ The one question that turns a bank's no into a roadmap Debt or dilution is a choice most founders make without understanding one side of it.

S5 · E21

22 lug 2026

1:07:39

Simplicity: The $11B charity, that's worth nothing, and can never be sold! | Sam Stubbs | 2 Commas with Josh Comrie

KiwiSaver fees in New Zealand will hit a billion dollars this year. Sam Stubbs has been the loudest voice in the country saying that's a scandal and building something to prove it doesn't have to be that way. Sam is the founder and CEO of Simplicity, an $11 billion KiwiSaver fund owned by a charity. It makes almost no profit. It is worth essentially nothing. It can never be sold. That's the point. When you ask people to trust you with their retirement savings, being unbuyable turns out to be an extraordinarily powerful thing. Before Simplicity, Sam was at Goldman Sachs listing Chinese companies on the New York Stock Exchange, flying on the Rolling Stones jet, and having lunch at the Ritz in the same room where Princess Diana dined the week she died. He made all the money he needed by 50, felt nothing from it, planted trees on an island for three years, then came back to take on the finance industry from the inside. Simplicity now gets between $5 and $16 million in member contributions every single day. It gives $10,000 to charity daily, builds 1.3 houses a day, saves its members $100,000 a day in fees, and gets 10% of new signups directly from AI engines with zero advertising spend. We get into: Why the finance industry is a priesthood and how they've kept it that way for decades The deliberate bank lobbying that set NZ open banking back 10 years Why KiwiSaver heading toward $1 trillion by 2070 is the most significant economic event in NZ history that founders aren't paying attention to How KiwiSaver funds could become the exit buyer of choice for NZ baby boomer business owners What Sam would say to any exited founder wondering what to do next If you're building something and wondering what it looks like to take on a billion dollar industry with almost no marketing budget and a model nobody thought would work, this one's worth your time.

S5 · E20

8 lug 2026

1:34:38

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