The Entrepreneur Experiment

Imagine selling your startup for $18 million in less than a year—only to watch it vanish into thin air when the dot-com bubble burst. Sounds like a wild ride? That’s just the beginning of John Dennehy’s incredible journey. John is one of Ireland’s most successful (and underrated) serial founders. He’s the only entrepreneur I know who’s managed to sell the same company twice. Yes, twice! In this episode, John shares how his journey went from massive wins to gut-wrenching losses—and back again. In 2024 alone, he pulled off two major sales, including the recruitment platform HireHive. But the real magic lies in how he bought back his old company, Zartis, reinvented it, and sold it again. John’s story has more twists and turns than a Hollywood blockbuster, and it’s packed with lessons for every entrepreneur. This is the ultimate guide to resilience, reinvention, and embracing the unpredictable. Don’t miss it! --- Thanks to my season title partner Local Enterprise Office: https://bit.ly/leodigital21  Find out more about digitalisation for your business in the link above.

Every great founder needs a mentor. That is why every single week, I bring you a new one. In this Mentor Moment, James Whelton dives into the importance of finding joy in the process over just chasing outcomes. He shares a key insight: if you're spending 90% of your time on the journey, it only makes sense to enjoy it. James reflects on his own experiences and how this mindset shaped his approach to work and success. This is a must-listen for anyone seeking a fresh perspective on aligning passion with purpose. To listen to the full episode go back to episode 306. --- Thanks to my season title partner Local Enterprise Office: https://bit.ly/leodigital21  Find out more about digitalisation for your business in the link above.

What does it take to build the backbone of one of the biggest gaming franchises in history and revolutionize digital safety for kids? In this episode of The Entrepreneur Experiment, Gary Fox sits down with Dylan Collins, the mastermind behind Demonware and SuperAwesome. Dylan shares the story of creating Demonware, the tech infrastructure that powers the online experience for games like Call of Duty, before selling it to Activision Blizzard in a landmark deal. But his journey didn’t stop there. Dylan went on to found SuperAwesome, a company dedicated to making the internet safer for kids, which was later acquired by Epic Games, creators of Fortnite. In this candid conversation, Dylan unpacks: The high-stakes decisions behind building and selling two global companies. How he predicted and shaped the future of gaming and children’s technology. Why digital safety is the next frontier in tech innovation. The mindset that keeps him asking, “What’s next?” after every success. Get inspired by one of the sharpest entrepreneurial minds of our time and learn how to anticipate trends, scale businesses, and stay ahead in the fast-moving world of tech.   (00:00) Entrepreneur Experiment Podcast With Dylan Collins (10:51) Surviving and Thriving in Business (14:37) Future of AI and Market Growth (21:41) Future of Physical Service Layers (28:42) The Future of Technology and Society (34:07) Global Fertility Rates and Investment Trends (47:24) Founder Insights on Selling Companies (01:00:54) Gaming Industry Entrepreneurship Explored (01:04:41) Building Relationships for Successful Acquisitions (01:10:54) Retail Power and Financial Literacy (01:20:43) Learning From Experiments and History (01:28:23) Ancient Mysteries and Founder Chemistry (01:38:29) Effective Capital Allocation Strategies (01:53:24) Strategies for Business Growth and Investments (02:02:56) Extended Entrepreneurial Interview With Dylan Collins   --- Thanks to my season title partner Local Enterprise Office: https://bit.ly/leodigital21  Find out more about digitalisation for your business in the link above.

Today's mentor is serial founder & investor, Ray Nolan. Ray built and sold Hostelworld for one of Ireland's biggest tech sales at the time for $500 million. He gives us a brutally honest assessment of the entrepreneur ecosystem in Ireland and the faults in the political support or lack of it. If you want to listen to the full episode with Ray, go back to episode 304.  --- Thanks to my season title partner Local Enterprise Office: https://bit.ly/leodigital21  Find out more about digitalisation for your business in the link above.