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

Jessie Stanley built a thriving pie empire from scratch—only to realise that success wasn’t what she imagined. In this candid conversation, Jessie shares her journey from obsessively hand-making pies to the complexities of scaling, the emotional rollercoaster of selling her beloved brand, and finding identity beyond the exit.

From navigating burnout and balancing motherhood to reinventing herself in the world of sustainable food inn...

Gary Gordon didn’t sell his company—he made the impossible call to shut it down. After two decades in property development and over $1B in completed projects, Gary walked away at the peak.

In this episode, we unpack the real reasons why, the lessons behind the numbers, and what it means to choose integrity over inertia. If you’ve ever questioned the cost of scale—or what it truly means to exit—this one will stay with you.

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Kelly Brown didn’t just grow a profitable business, she exited on her own terms. From a failed M&A attempt to a four-month sprint that led to a clean, quiet sale, she shares what it really takes to build a company that’s not just valuable, but truly sellable.

In this episode, we dive into what founders get wrong about exits, why culture without accountability doesn’t work, and how to create a business that thrives without you. W...

Alliv Samson didn’t just build a startup, she redefined how classrooms work around the world. As the co-founder of Kami, she navigated massive growth during the global pandemic, scaling from 7 million to 40 million users almost overnight. From nearly shutting down to becoming one of the fastest-growing EdTech companies globally, Alliv shares candid insights on knowing when to pivot, handling rapid success, and why money should neve...

Mark Clare hasn't just advised on hundreds of successful business exits; he’s seen firsthand the pivotal moments that make or break multi-million dollar deals. As the founding partner of Clare Capital, Mark has become the go-to expert for Kiwi founders navigating the complex world of mergers and acquisitions, particularly in the SaaS space.

In this episode, Mark shares why competitive tension is your best friend (and why many New Ze...

Greg Munt always knew he was building to sell. Even the name of his business, One50 Group, was a constant reminder of his ambitious $150 million exit goal. From a high school dropout buying properties at 19, to becoming a top mortgage broker in his twenties, Greg's journey is one of relentless drive, strategic pivots, and impeccable timing. In this episode, Greg shares how setting audacious goals shaped his decisions, why knowing y...

Nick Crawford didn’t build a career in wealth management AND a philosophy around what money really means after the cheque clears. From advising lottery winners to helping founders post-exit, he’s seen firsthand how sudden wealth often triggers more anxiety than freedom.

In this episode, we dive into the emotional aftermath of selling your business, the psychology of “how much is enough,” and why some of the biggest financial mistake...

Janine Grainger built conviction in a space most people didn’t know or trust. From raising NZ’s largest-ever first-round funding to leading through crashes, cutbacks, and global scrutiny, she grew Easy Crypto into a $3.5B platform before its exit to an Australian acquirer.

In this episode, we unpack what it takes to build credibility in volatile markets, the emotional reality of exiting a mission-led company, and how Janine quietly ...

Trent Mankelow is one of the OGs of New Zealand’s design and startup scene — a founder, UX leader, and advisor who helped shape the early digital product landscape here. In this conversation, Trent and I talk about what happens when you hit product-market fit... but aren’t ready for what comes next.

We unpack the emotional weight of selling your company, the governance gaps that nearly cost them the deal, and the tension between cus...

Elena Kim didn’t just become one of New Zealand’s most influential lawyers—she built her career helping founders exit well. From navigating M&A deals to managing complex stakeholder dynamics, she’s seen what breaks deals, what builds value, and what founders often learn too late.

In this episode, we unpack the human side of selling a business, the real risks hidden in your shareholder agreements, and why the right legal strategy...

Igor Portugal spent two decades mastering markets—leading hedge fund strategies and managing billions in capital. But when the industry no longer aligned with his values, he made a rare move in finance: a voluntary, intentional exit. No dramatic blow-up. Just a calculated decision to leave while ahead.

In this episode, we unpack how to know when it’s time to exit, the strategy behind leaving a high-performing career, and why Igor be...

Shane Brealey doesn’t just build buildings—he builds movements. After leading Multiplex NZ and founding NZStrong, he made what he calls his “Jerry Maguire” exit: walking away from corporate power to do things on his own terms. Since then, he’s gone from construction heavyweight to housing reformer, using his deep industry knowledge to deliver affordable, high-quality homes through NZ Living and now Simplicity Living.

In this episode...

Debra Hall is a serial founder, governance expert, and one of New Zealand’s most respected angel investors. She sold her award-winning market research firm, Research Solutions, to global giant Synovate, and now mentors founders on building exit-ready businesses.

In this episode, we dive into the emotional rollercoaster of selling your company, why strong governance drives higher valuations, and how to shift from founder to boardroom...

Linda Jenkinson is a serial entrepreneur, impact investor, and the first New Zealand woman to list a company on the NASDAQ. In this episode, she unpacks what it takes to scale globally, lead across continents, and create businesses that drive both profit and purpose.

From managing hundreds of thousands of gig workers to building companies that solve real-world problems, Linda reveals the mindset shifts, leadership challenges, and pe...

Roy Crane is a seasoned entrepreneur who turned his helicopter training business into a thriving enterprise before successfully navigating a high-stakes exit. In this episode, Roy shares powerful insights on the emotional toll of selling your business, the strategic moves that sealed the deal, and how to redefine your purpose post-exit. Whether you're planning to sell or scaling for growth, Roy’s journey offers invaluable lessons o...

Neil Millar is one of New Zealand’s leading M&A lawyers with over 25 years of experience, advising on multi-million dollar deals across various industries. In this episode, Neil shares how he navigates complex transactions, the unexpected pitfalls founders face during exits, and why successful M&A requires balancing persuasion, preparation, and patience. From grumpy markets to regulatory shifts, Neil offers invaluable insig...

Seeby Woodhouse, a pioneering entrepreneur in New Zealand's internet space, built Orcon from the ground up, starting at just 19 years old. In this episode, he shares how he scaled the company, navigated near-bankruptcy, and sold it in a multimillion-dollar exit before turning 30. He reflects on the lessons from that deal, the fortune he left on the table, and his journey through investments, photography, and a return to telecommuni...

From building 10 companies to executing 15 strategic acquisitions, Mike Marr shares the secrets behind scaling through M&A. In this episode, he breaks down the five-stage acquisition process, the common pitfalls buyers face, and how culture can make or break a deal. Whether you’re a founder eyeing an exit or an entrepreneur looking to grow through acquisitions, this episode is packed with invaluable insights.

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