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

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

por Josh Comrie

Temporada 2

Trent Mankelow: Exit before you hate it!

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 customer obsession and investor expectations. If you’re building with an exit in mind — or maybe should be — this one’s full of lived experience. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Elena Kim: Founders, don't wait to get your house in order!

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 isn’t about avoiding conflict—it’s about planning for it. Whether you’re preparing to sell or just thinking about what comes next, this conversation is a roadmap for navigating exits with clarity, control, and confidence. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Igor Portugal: The accidental CEO: when startups, divorce, and M&A collide!

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 believes your best trade might be walking away. Whether you're planning your next move or rethinking what long-term success looks like, this conversation is a masterclass in exiting on your own terms. Book Recommendations Unasked Questions by Igor Portugal The Goal by Eliyahu M. Goldratt - Structural inspiration for Igor’s book. The Phoenix Project by Gene Kim - Another narrative-style business book model. Five Dysfunctions of a Team by Patrick Lencioni - A reference point for narrative-driven business learning. Atlas Shrugged by Ayn Rand - Referenced for its philosophical style that inspired Igor's earlier novel idea. On Writing by Stephen King - For anyone learning the writing craft... “an amazing book” for aspiring authors. Economical Writing - For improving sentence-level technical writing. 🎙️ Podcasts for Writers Fiction Author Business School by Lizelle Hill - Igor binged the entire podcast and considers her a key inspiration. The Self-Publishing School Podcast by Chandler Bolt - Tips on self-publishing, writing motivation, and strategy. The Creative Penn Podcast by Joanna Penn - Offers guidance on both creative writing and self-publishing. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Shane Brealey: Impatience, integrity, impact - Brealey on giving it away!

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, I sat down with Shane to unpack the psychology of leaving big business, the truth about what most developers get wrong, and why he believes the best deals aren’t the biggest—they’re the ones that change lives. Whether you’ve exited already or are thinking about what’s next, this one’s a blueprint for building again—with more clarity, impact, and heart. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Debra Hall: “We don’t hire female Engineers...” Challenge accepted!

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 force. Whether you're scaling, selling, or starting over—this conversation is packed with real-world lessons from both sides of the exit. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Linda Jenkinson: How to think (and scale) like a billionaire!

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 personal sacrifices behind bold entrepreneurship — and what she's doing now to empower the next generation. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Roy Crane: Altitude, attitude, & adaptation: Lessons from a life in flight

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 on resilience, leadership, and life after letting go. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Neil Millar: NZ’s top M&A Lawyer on deals, drama, & DD!

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 insights for founders, business owners, and investors preparing for their next big move. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Seeby Woodhouse: A $24m exit in my 20's!

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 telecommunications with Voyager. A candid conversation about risk, resilience, and the highs and lows of life after a big exit. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

Greg Young: M+A Advisor talks vendors out of selling?!

From structuring multi-million dollar deals to navigating complex exits, Greg Young shares the insider secrets of M&A. In this episode, he breaks down the biggest red flags that kill deals, how to prepare your business for sale, and why most founders leave money on the table. Whether you're planning an exit or looking to acquire, this episode is packed with must-know insights. Subscribe to the 2 Commas Journal to receive business insights and real exit lessons straight to your inbox https://bit.ly/47lfcPU Download the first 2 chapters of my upcoming book, 2 Commas, for free here https://bit.ly/3WisuYo Follow me on LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.linkedin.com/in/joshcomrie⁠⁠⁠⁠⁠⁠⁠⁠ Visit https://www.joshcomrie.com/ to see how I can help you on your business journey.

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