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 innovation, Jessie’s story explores the personal side of entreprene...
Jun 25, 2025•1 hr 43 min•Season 3Ep. 4
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. Follow me on LinkedIn: www....
Jun 18, 2025•1 hr 17 min•Season 3Ep. 3
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. Whether you're years away from selling or simply want to lead wit...
Jun 11, 2025•1 hr 12 min•Season 3Ep. 2
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 never distract you from your mission. Whether you're growing your sta...
Jun 04, 2025•1 hr 28 min•Season 3Ep. 1
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 Zealand founders miss the mark here), what truly drives company va...
May 28, 2025•1 hr 7 min•Season 2Ep. 16
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 your buyer's mindset is crucial, and the delicate art of pivoting ...
May 21, 2025•1 hr 13 min•Season 2Ep. 15
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 mistakes are driven by ego, not strategy. Whether you’re approaching an...
May 14, 2025•1 hr 11 min•Season 2Ep. 14
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 launched a skunkworks project during a bear market because it fe...
May 07, 2025•1 hr 19 min•Season 2Ep. 13
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 wi...
Apr 30, 2025•1 hr 33 min•Season 2Ep. 12
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. Wheth...
Apr 23, 2025•1 hr 14 min•Season 2Ep. 11
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 pla...
Apr 16, 2025•1 hr 20 min•Season 2Ep. 10
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 ...
Apr 09, 2025•1 hr 13 min•Season 2Ep. 9
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 c...
Apr 02, 2025•1 hr 25 min•Season 2Ep. 8
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 ...
Mar 26, 2025•1 hr 42 min•Season 2Ep. 7
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. Follow me on...
Mar 19, 2025•1 hr 14 min•Season 2Ep. 6
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 th...
Mar 12, 2025•1 hr 26 min•Season 2Ep. 5
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, resilienc...
Mar 05, 2025•1 hr 51 min•Season 2Ep. 4
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.
Feb 26, 2025•1 hr 32 min•Season 2Ep. 3
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. Follow me on LinkedIn: www.linkedin.com/in/joshcomrie Download my e-book, "...
Feb 19, 2025•1 hr 14 min•Season 2Ep. 2
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 business growth with a strategic exit. If you're an entrepreneur, e...
Feb 12, 2025•1 hr 11 min•Season 2Ep. 1
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 my journey. We talk about the best (and worst) advice I’ve rec...
Feb 05, 2025•1 hr•Season 1Ep. 12
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 next move, this episode is packed with insights on scaling, s...
Jan 29, 2025•1 hr 22 min•Season 1Ep. 11
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 for founders and CEOs seeking inspiration for scaling, selling, ...
Jan 22, 2025•1 hr 32 min•Season 1Ep. 10
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 prepare for an exit. This episode is a must-watch for anyone eager t...
Dec 18, 2024•1 hr 18 min•Season 1Ep. 9
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 against the odds, and the lessons learned from navigating partners...
Dec 11, 2024•1 hr 14 min•Season 1Ep. 8
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. Follow me on LinkedIn: www.linkedin.com/in/joshcomrie Dow...
Dec 04, 2024•55 min•Season 1Ep. 7
In this episode of Two Commas , I sit down with Jovan, a former firefighter turned entrepreneur, who built and sold a FinTech business for a 7-figure exit. From starting out in a cramped room in London to negotiating three competitive offers, Jovan shares the highs, lows, and lessons learned along the way. We explore the grit it takes to disrupt archaic systems in financial services, the balancing act of "one foot in, one foot out" during the exit process, and the reality of life after the deal—...
Nov 27, 2024•1 hr 12 min•Season 1Ep. 6
In this episode of Two Commas , I sit down with Miles Valentine, a seasoned entrepreneur who shares the inside story of his $40M telco software exit. From bootstrapping in New Zealand to breaking into the US market, Miles offers hard-hitting lessons on pricing strategies, scaling challenges, and navigating investor dynamics. Whether you’re preparing for an exit or looking to scale smarter, this episode is packed with expert insights and real-world strategies. A must-listen for founders, investor...
Nov 20, 2024•1 hr•Season 1Ep. 5
In this episode of Two Commas , I sit down with James McCarthy Toia, an innovative problem-solver who transformed his aviation tech venture from a small startup to a global leader, culminating in an 8-figure exit. James takes us through his journey—from his beginnings in rural New Zealand, where his entrepreneurial drive first sparked, to building technology that reshaped aviation safety tracking. We unpack the key decisions and strategies that set his company apart, the hurdles faced during sca...
Nov 13, 2024•1 hr 21 min•Season 1Ep. 4
In this episode of Two Commas , I sit down with Tom Price, a self-made entrepreneur who grew an air conditioning business from a scrappy startup to a multimillion-dollar operation, ultimately leading to a high-stakes exit. Tom shares his unique journey—beginning with flyers and DIY installations to scaling his business and even starting a manufacturing line in China. He reveals the gritty, hands-on decisions that built his company and the unforeseen challenges of due diligence with venture capit...
Nov 06, 2024•1 hr 13 min•Season 1Ep. 3
