2 Commas: The $multi-million exit show with Josh Comrie
Welcome to 2 Commas: The $multi-million exit show I've spent over two decades helping founders scale their businesses and achieve successful, multimillion-dollar exits. I've also achieved this myself on multiple occasions. With my experience as an entrepreneur, advisor, and investor, I’ve had the privilege of guiding companies through the highs and lows of business growth and exit strategies. Each episode will bring you the previously untold stories of entrepreneurs who have successfully scaled and exited their businesses for seven-figure (2 comma's) plus returns. You’ll hear more about the journeys, challenges, and pivotal moments that led to these transformative exits. My goal is to inform and inspire founders who are looking to scale their ventures to seven, eight or nine figures and beyond. Follow me on LinkedIn: www.linkedin.com/in/joshcomrie Download my e-book, "The Exit Factor" and sign up to receive the Business Growth Journal weekly: https://www.joshcomrie.com/the-exit-factor
Episodes
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 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.
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.
In this episode of Two Commas, I sit down with Kris Nygren—an expert in business strategy, governance, and scaling companies to successful exits. From leading Optimal Usability through rapid growth to navigating its acquisition by PwC, Kris shares the hard-won lessons of scaling, selling, and transitioning leadership. We explore the role of trust in high-stakes deals, the nuances of governance, and what it really takes to align bus...
For the first time ever, I switched seats in this episode of Two Commas. My wife, Tina, put me under the spotlight, asking the tough questions about my entrepreneurial journey, the lessons from multiple business exits, and why I started this podcast in the first place.
From my first paper round at 12 to building, scaling, and exiting multiple businesses, we dive deep into the lessons, the missteps, and the mindset shifts that shaped...
In this episode of Two Commas, I sit down with legendary entrepreneur Tony Falkenstein—NZ Business Hall of Fame inductee and serial founder with over 50 ventures to his name.
From scaling companies to public listings, navigating high-stakes acquisitions, and bouncing back from failures, Tony shares the raw lessons of a lifetime in business. Whether you're a founder eyeing growth, an investor assessing value, or a leader shaping your...
Discover the incredible journey of Matt Chapman in this episode of Two Commas.
Growing up in a small country town in Australia to building a global HR search firm with a virtual workforce ahead of its time, Matt takes us through his journey of reinvention and resilience. Hear how he scaled his business to a $100m exit, navigated the challenges of burnout, and found new purpose as a custodian of transformation and wellbeing. Perfect ...
How do you turn a bold idea into a global SaaS success and achieve two multimillion-dollar exits? 🎙️
In this episode of Two Commas, Michael Cardin shares his entrepreneurial journey, revealing the strategies and mindset shifts that helped him build and sell thriving businesses. From mastering SaaS sales from New Zealand to navigating high-stakes negotiations, Michael offers practical insights for founders looking to scale and prepa...
What’s the secret to turning a small recruitment company into a national powerhouse, leading to a multimillion-dollar exit? 🎙️
In this episode of Two Commas, I chat with Marisa Fong, a trailblazing entrepreneur who scaled her business from a part-time receptionist setup to a thriving enterprise acquired by a major player.
Marisa shares her unfiltered insights on crafting a scalable business culture, winning government contracts agai...
What does it take to scale a company from two people to 400 and secure an £87M exit? 🎙️
In this episode of Two Commas, Rudi Bublitz reveals the key inflexion points that drove his company’s success, the art of training talent over hiring experience, and the critical role of timing in making the perfect exit.
From bold cultural moves to strategic decisions, Rudi shares lessons every founder scaling towards their big win needs to hear...
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