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

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

by Josh Comrie

Entrepreneurship

Season 3

Pro services company legends: timeless business lessons

Marisa Fong, Matt Chapman, and Jovan Pavlicevic each built and exited companies on their own terms — but the lessons they share are universal. From chasing government contracts as a two-person team, to scaling a global freight train, to selling before the market turned, their stories reveal how ambition, timing, and resilience shape the founder journey. This best-of episode isn’t about theory or glossy headlines. It’s the messy, human side of building and exiting — told by founders who’ve been there, scarred, and succeeded. If you’re growing, scaling, or planning an exit, these are the insights you’ll want in your back pocket. 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.

Startup legends on how to start, scale, and sell

Mike Carden, Will Palmer, and James McCarthy each built, scaled, and sold SaaS companies in very different ways — but all with lessons that matter for founders today. From surviving the GFC with no cash, to putting profitability ahead of vanity growth, to mastering the art of storytelling as a sales weapon, their experiences cut through the myths of startup success. This “best of” episode isn’t polished theory. It’s real stories, hard scars, and the kind of wisdom you only get from the trenches of building and exiting. If you’re starting, scaling, or staring down an exit, you’ll find insights here worth stealing. 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.

Vicki Ammundsen: NZ's top Trusts Lawyer tells all

Vicki Ammundsen didn’t become one of New Zealand’s most sought-after trust and tax lawyers by playing it safe. She’s spent decades helping founders, families, and advisors navigate the uncomfortable questions most people avoid—until it’s too late. In this episode, we explore the hidden cracks in succession planning, the emotional blind spots that derail even the best-laid legacies, and why giving your kids shares in the family business might be the worst gift of all. Vicki shares the patterns she’s seen behind high-stakes exits, multi-generational wealth plans, and business transitions that either protect the founder’s vision — or slowly unravel it. Whether you’re planning to step back or just starting to build something worth passing on, this conversation is a wake-up call to plan with clarity, intention, and courage. 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.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Symon Thurlow: We 4 X'd our earn-out! Here's how.

Symon Thurlow didn’t set out to sell his business — but when opportunity knocked, he took the deal and stayed on for seven more years. What followed wasn’t just a transition. It was a transformation. In this episode, we unpack what really happens when you scale a niche services business to $20M+, navigate an earnout with zero prep, and lead post-acquisition without losing your identity. From trusting your gut to learning the language of corporate, Symon’s story is proof that exits aren’t just about walking away — they’re about stepping into the next version of yourself. Whether you’re building a business, considering a sale, or already on the inside post-acquisition, this conversation offers grounded insights into navigating the long game. 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.

Ben Forman: I walked away from millions. Here's why I'm at peace.

Ben Forman built an incredible business around storytelling, intuition, and timing. From pioneering New Zealand’s first commercial drone business to selling Wrestler after years of soul-searching, Ben has seen both the magic and the messiness of entrepreneurship. In this episode, we unpack what it really means to build something meaningful, why knowing your “why” can save you millions, and how letting go at the right time can be the most powerful move of all. Whether you're scaling, stalling, or standing at the edge of an exit, Ben’s story is a masterclass in clarity, timing, and staying human in business. 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.

Kimberlee Sweeney: My first divorce wasn't my marriage. It was my business.

Kimberlee Sweeney has seen what tears relationships apart, not just in marriages. As New Zealand’s first divorce coach, she also works with business partners, co-founders, and leadership teams to stop breakdowns before they happen. In this episode, we dive into the psychology of founder dynamics: the unspoken expectations, emotional blind spots, and behavioural patterns that can quietly destroy a great business. From prenups for partnerships to navigating resentment when roles aren’t equal, Kimberlee offers a roadmap for conflict prevention, repair, and clarity, especially when the stakes are high. Whether you're in a co-founder relationship, planning an exit, or leading a team through friction, this conversation will change the way you think about trust, alignment, and emotional due diligence. 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.

Kaz Staples: $15 cereal; Impossible they said! I built the category and my empire.

Kaz Staples didn’t set out to build an iconic food brand—she just wanted to make honest muesli. But over 25 years, she turned Pure Delish into a household name. Along the way, she faced near-collapse during the GFC, fought through burnout, and rebuilt a business on gut instinct and grit. In this episode, we explore what it really takes to lead through chaos, the emotional cost of carrying a company on your back, and what happens when you finally walk away. Whether you’re building something or wondering how to let go, Kaz’s story is a masterclass in resilience, reinvention, and the power of staying true to your values. 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.

John Bolton: At 32 I walked from a $60B portfolio. Into nothing.

John Bolton (JB) walked away from managing a $60 billion portfolio at the onset of the Global Financial Crisis, betting everything—his house, savings, and future—on a dream. His journey with Squirrel wasn’t just about creating a successful mortgage and lending business; it was about embracing uncertainty, surviving near-bankruptcy, and building resilience through relentless innovation. In this episode, JB candidly shares why naivety can be an entrepreneur’s greatest asset, the critical importance of timing and capital strategy, and how stepping aside from leadership allowed his company to scale. Whether you're navigating your own startup journey or considering what comes next, JB's insights provide an authentic roadmap to taking bold risks and transforming challenges into lasting success. 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.

Ryan Sanders: $34M in revenue. Slashed by 94% overnight.

Ryan Sanders didn’t exit because the business was broken—he left because he was ready. After building one of Aotearoa’s most iconic tourism brands, he walked away on his own terms, in the middle of a pandemic. In this episode, we unpack the emotional terrain of stepping back while the business is still thriving, the quiet toll of staying too long, and the unspoken identity crisis that comes with no longer being “the founder.” Whether you’re thinking about selling or just asking yourself what comes next, this is the conversation you didn’t know you needed. 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.

AJ Wilderland: Block my company sale? I'll find a better deal!

AJ Wildland co-founded one of the coolest tech companies to come out of NZ and helped revolutionise DJing globally. From bootstrapping Serato with a groundbreaking algorithm to navigating a $100M exit and stepping into the political arena, AJ’s journey is as bold as his beliefs. In this episode, we explore how a bass guitarist’s personal pain point became a global solution, why selling Serato wasn’t just about the payday, and what happens when a tech founder decides to fix the country instead of another product. Whether you're a founder, creative, or voter this conversation is equal parts insight, inspiration, and provocation. 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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