EE 396 - Behind the Scenes of Building a Unicorn with Jack Pierse

Welcome to the final podcast of 2024.  In this special episode recorded live at the first-ever guests reunion in Dublin, I sit down with two of my most popular guests, Nadia Adan and Michael Corcoran. We look back on the highs and lows of 2024 sharing the lessons, wins and learnings from the year. With over 70 founders in the audience, we also delved into the trends and predictions that will shape the next 12 months.  Shot live with a studio audience at Baseline in Dublin City. --- 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.   *Music by Andrew Applepie. 

What does it take to create a unicorn startup? Jack Pierse, co-founder of Wayflyer, and now co-founder of HappyStack joins us to discuss the thrilling journey of building one of the most successful startups in recent years. From securing millions in funding to scaling operations across the globe, Jack shares invaluable insights into the entrepreneurial highs and lows, including the pivotal moments that shaped Wayflyer’s meteoric rise. Jack opens up about his life before and after Wayflyer, including his working for Liam Casey and how he’s now channelling his expertise into new ventures. Whether it’s advising other startups, investing, or exploring new industries, Jack’s approach to entrepreneurship continues to evolve. His latest venture, Bold Golf has also just launched and counts Shane Lowry among the investors.  --- 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.

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.

In this episode, I sit down with Phillip McGlade, the CEO of Therapie Clinics, to uncover the secrets behind building Europe’s largest aesthetics chain—a business turning over €100 million annually. With 77 clinics across the globe, Therapie has become a household name in beauty and wellness. But Phillip isn’t stopping there; he’s now expanding into fertility clinics, tackling deeply personal and impactful challenges. We dive into the mindset that fueled 14 years of relentless growth, the sacrifices Phillip has made along the way, and how he balances family with building a business empire. You’ll hear about the big risks, bold moves, and lessons learned from scaling not just one, but two life-changing ventures. Whether you're a founder, aspiring entrepreneur, or just curious about what it takes to create a €100+ million business, this conversation will leave you inspired and ready to take action. --- 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.

In this episode, Gary sits down with Conor Sheridan, the mastermind behind Mad Egg & Nory, to dive into the nitty-gritty of the restaurant world and how he's shaking things up. This is the second time Conor has been on the pod and we catch up on a whirlwind few years for Conor as he raised $25 million to build Nory, the operating system for restaurants. Conor is building the ultimate operating system for restaurants to help them thrive, not just survive. We chat about why so many restaurants struggle with profit, how digital tools can change the game, and what it takes to scale up from a local spot to a powerhouse brand. Whether you’re in hospitality or just hungry for business insights, Conor’s journey will inspire and entertain. Tune in and get a taste of the future of dining!   Here is a sneak peek of some of the lessons in today's pod. Optimize for Efficiency: Profitability often hinges on operational efficiency rather than just increasing sales. Adapt Quickly: Embrace adaptability as a survival tool, especially in competitive or challenging markets. Leverage Technology: Use digital tools to streamline operations and stay competitive in a fast-evolving industry. Tell a Compelling Story: When fundraising, present a clear vision that solves real, pressing problems. Build a Strong Culture: Cultivating a positive work culture aligns your team with the mission and fuels growth.   Show Notes Connect with Conor Sheridan: Mad Egg Nory Connect with Gary Fox: Follow Gary on LinkedIn Join Gary's free weekly email newsletter community.  Listen & Subscribe: Don’t miss out on future episodes where we uncover the founder’s formula for success. Subscribe on Apple Podcasts, Spotify, YouTube or wherever you get your podcasts! --- 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, we have a world exclusive. Will O'Brien unveils his stealth startup to the world for the first time. Will is my pick for the rising star of season 22 and this episode will clearly show why. Not only is he backed by some of the hottest investors in the world, he is solving a problem that could potentially save the world.  Will shares the rationale behind keeping his company under wraps for so long, focusing on engineering challenges away from the public eye. Our conversation then turns to the ambitious quest of seagrass restoration, an innovative solution for carbon removal. We explore the immense potential of scaling restoration efforts, fueled by global climate goals, and discuss the strategic fundraising journey that brought on board top-tier investors aligned with the venture's long-term vision. Will is a fascinating guy and we explore some of his wilder adventures including going to live with Buddhist monks and writing letters to Denis O'Brien which landed him a dream job. --- 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. Bad writing and communication is holding your business back.  Learn how to unlock this marketing superpower in today's Mentor Moment.  Eamon Fitzgerald has used writing and in particular email newsletters to grow a business worth millions. Eamon is the founder of WineSpark. --- 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. --- Listen to the full Eamon episode: https://youtu.be/YKIHvFW6hEc?si=6KtBT1xCZktYWpQ7