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

Laetitia Peterson: Wall St doesn't prepare you for startup life

Laetitia Peterson sold her investment company, Liontamer, to a global banking giant - only to watch her buyer teeter on bankruptcy just months later. From navigating a sale at the peak of the market to reclaiming her business during the Global Financial Crisis, Laetitia has faced entrepreneurial highs, daunting lows, and every challenge in between. In this candid conversation, we explore the unexpected twists in exits, the resilience required to pivot amidst chaos, and why the best strategies aren’t always about predicting the future, but being prepared for uncertainty. If you're building towards an exit, or simply wondering what comes next, this episode offers real-world wisdom on managing the unpredictable journey of selling your 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.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Keith Davison: 0-$120m exit in 2.5 years!

Keith Davison persevered through five failed startups before achieving a remarkable $120 million exit (in under 3 years from first revenue!). From hustling without a salary for over two years to strategically navigating market timing, Keith’s story reveals the gritty truths behind entrepreneurial success. In this candid episode, we explore what it truly takes to scale a startup, the risks and realities of exiting at the right moment, and how relentless resilience can transform failures into life-changing outcomes. Whether you’re an aspiring entrepreneur or contemplating your next business move, Keith’s insights offer a practical and inspiring blueprint for navigating the highs, lows, and unexpected turns of entrepreneurship. 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.

Jessie Stanley: From pies to flies. Passion, purpose & problems!

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 entrepreneurship—showing that sometimes, exits aren't endings, but rather new beginnings. 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.

Gary Gordon: $1B of property developed. Here's what I know.

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. 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.

Kelly Brown: 18 yrs of leadership; leave a legacy

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 with more intention, this conversation is a masterclass in long-game leadership. 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.

Alliv Samson: $300m NZ success story "NO silicon valley"

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 startup, considering an exit, or just curious about the resilience needed to thrive through uncertainty, this conversation will inspire and equip you for the road ahead. 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.

Season 2

Mark Clare: You set the price, l'll set the terms!

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 valuations, and the hidden pitfalls in negotiations that can cost you millions. Whether you're planning your exit or just curious about the strategies behind successful deals, Mark's insights offer essential guidance to maximise your outcome and avoid costly mistakes. 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 Munt: Reverse engineering a $150M vision!

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 business models without losing your best people. If you're building towards an exit, considering your next strategic move, or simply looking for clarity on how to scale smartly, this conversation is packed with insights you won't want to miss. 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.

Nick Crawford: You're rich, but still miserable. Here's why...

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 exit or navigating what comes next, this is an honest, nuanced look at wealth, identity, and the planning that truly brings peace of mind. 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.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Janine Grainger: Crypto billions: how I sold Easy Crypto!

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 felt like the right thing to do. If you’re navigating uncertainty, leading with purpose, or thinking about the long game this conversation is invaluable. 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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