AMA: Breakout Founders for 2026 + My Boldest Predictions

Welcome back to The Entrepreneur Experiment for 2026 - and Season 28 kicks off with a special format: an Ask Me Anything Q&A. Gary answers the most “juicy” questions sent in over Christmas (LinkedIn, Instagram, and the newsletter), covering everything from taking the podcast global, to the tools and team behind the scenes, to why he’s doubling down on founder-led brands in the age of AI. You’ll also hear Gary’s hot takes for 2026 (see: remote vs. hybrid: pick a lane), the founders he believes will have breakout years, what he’d do differently if he started again, and the one mindset shift he’s bringing into the new season: decisiveness. 🎧 If you like this AMA style, Gary’s already decided: more Q&As are coming - including AMAs with past guests, o make sure you’re following us on socials (linked below) to get involved, or join the newsletter (linked below). Show Notes In this Season 28 opener, Gary kicks off 2026 with an Ask Me Anything episode — answering questions sent in over Christmas from LinkedIn, Instagram, and the newsletter. We touch on: When (and how) the podcast is going global — UK, Middle East, and the US The 2026 goal: don’t look like a podcast — look like a media company The team + tools behind the scenes (and the one tool Gary can’t live without) Founder-led brands in the age of AI: why Gary is more bullish than ever A few breakout predictions for the year ahead Gary’s hot take for 2026 (and why “uncertainty” kills momentum) What he’s leaving in 2025… and what he’s bringing into 2026 If you want more of these AMAs, tell Gary —-he’s already planning the next twist on the format. Resources (mentioned or referenced) Books Unreasonable Hospitality — Will Guidara People / Brands referenced Manna (Bobby Healy) - https://www.manna.aero/ Tech Powered Luxury - https://www.instagram.com/techpoweredluxury/?hl=en Ireland Fashion Week - https://www.instagram.com/irelandfashionweek/?hl=en Represent (George Heaton) - https://www.instagram.com/georgeheaton/?hl=en Marchon (Ollie Marchon / bottle + products) - https://www.instagram.com/olliemarchon/?hl=en “Open Residency” episode with George Heaton (hosted by Mark Brazil, co-founder of IKONICK) - https://www.youtube.com/watch?v=6tTLUuD06AY Tools Gary uses Notion ChatGPT Calendly Typeform ManyChat Todoist Moleskine ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

Recorded live at The Sugar Club, this special edition of The Entrepreneur Experiment brings three standout Irish founders on stage for an honest, high-energy conversation about building modern businesses in public. Aine Kennedy, founder of The Smooth Company and newly crowned EY Entrepreneur of the Year, shares how she launched her first product with no budget, built everything herself, with the help of her family, and turned documenting the journey on TikTok into 150 million organic views, now shipping to 70 countries worldwide. Nadia Adan, founder of Ashford Motors, breaks down how she went from a small yard and a handful of cars to creating one of Ireland’s most recognisable automotive brands - by obsessing over customer experience, moving faster than traditional dealers, and using social media to build trust at scale. Rounding out the panel, Jack Pierse, co-founder of Wayflyer and now Bold Golf and Happy Stack, reflects on launching a fintech at the start of COVID, scaling to €100 million per month in lending, the realities of hypergrowth, and what he’s doing differently this time. From viral content and community-led growth to staying lean, moving fast, and learning the hard lessons of scale, this live episode is packed with real-world insight, plenty of humour, and unfiltered founder stories. An entertaining and insightful listen for you! Show Notes Hosted by Gary Fox, with Aine Kennedy, Nadia Adan, and Jack Pierse Recorded live at The Sugar Club, Dublin How Aine Kennedy launched The Smooth Company from scratch and built a global brand by documenting the journey online Turning TikTok into a growth engine: 150 million organic views and customers in 70 countries Why building in public — without gatekeeping — is changing who feels able to start a business Nadia Adan’s rise from a small car yard to one of Ireland’s most recognisable automotive brands Using customer service, flexibility, and speed to outperform traditional main dealers Dealing with online trolls when reputation and real-world sales are on the line The Wayflyer origin story: launching during COVID and scaling to €100M per month in lending The realities of hypergrowth, rapid hiring, and the lessons learned the hard way Why Jack Pierse is building his second company, Happy Stack, slower and leaner A candid, entertaining live discussion on growth, community, and staying adaptable in modern business Links & Resources The Smooth Company – https://www.thesmoothcompany.com/ Ashford Motors - https://www.ashfordmotors.ie/ Happy Stack – https://www.happystack.com/ Bold Golf - https://bold-golf.com/ ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE   Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

How do you build a powerful business network when you’re starting with no members, no brand, and no shortcuts? In this Mentor Moment, Trevor McFarlane, founder and CEO of EMIR, shares how he built one of the Middle East’s most influential private CEO networks — starting with a single event, a lot of nerve, and an obsession with trust and curation. Trevor explains why optics matter, how credibility compounds over time, and why protecting the integrity of a network is far more valuable than short-term revenue. 🎙️ To hear the full story — including how EMIR scaled across the region and the lessons Trevor learned along the way — listen to Episode 411 of The Entrepreneur Experiment. 💡 If you enjoy these short Mentor Moments, don’t forget to follow or subscribe to the podcast for more founder insights every week. ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE   Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

In this episode of The Entrepreneur Experiment, Gary Fox welcomes back Matthew Coffey, co-founder of Squid, Ireland and the UK’s largest local loyalty network with 550,000+ users and nearly 2,000 independent businesses. What began as a simple tap-for-coffee reward app has evolved into a powerful loyalty and payments infrastructure - and now Squid has launched Wave, a universal points currency described as “air miles for the high street.” You can now earn points in one brand and redeem them in another, all by linking your everyday spending cards. Matthew breaks down how Squid integrated with global giants like Square, raised over €10 million, and is now preparing to expand Wave across Europe as a new rewards-powered payment rail. He also shares the founder lessons he’s learned, from communication to fundraising to scaling fast without losing trust and integrity. If you’re curious about loyalty, fintech, payments, or the realities of scaling a startup into a European network, this episode is essential listening. Show Notes In this episode, Gary chats with Matthew about: How Squid grew from free coffee stamps to 550,000+ users and almost 2,000 independent businesses. Why Matthew & Katie focused on coffee shops to build a two-sided network from scratch. Introducing Wave — “air miles for the high street” where you earn across brands automatically. How card-linking with Visa/Mastercard/Amex enables one-touch loyalty. The impact of integrating with Square to give independents big-brand loyalty and data tools. The journey from early-stage startup to raising over €10m, including a €1.7m+ crowdfunding round. The North Star metric Squid tracks: the total free product given back to users. Squid’s two-step scaling playbook for Europe: launch loyalty locally, then layer Wave on top. Why 2026 will be the “year of payments” as Squid builds a rewards-driven payment rail. Matthew’s biggest founder lessons: communicate better, expand earlier, trust technology, and be relentless. Links & Resources Download Squid on iOS / Android: https://tr.ee/WFmx4sOqmR ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

What happens when a founder opens the company’s books to every single staff member — salaries, P&L, everything? In this episode, Eoin Cantwell, founder of Fitt Meals, shares the bold move that transformed his culture, boosted performance, and created true ownership across his team. Eoin opens up about: why he embraced full financial transparency with staff how he teaches the “why” behind decisions, not just the “what” building accountability and KPIs in a growing food business scaling a bootstrap company while protecting quality the mindset shifts he had to make to become a better leader This is a brilliant, honest look at modern leadership — the messy bits, the growing pains, and the breakthroughs. 🎧 Listen now and hear why Eoin believes the future of high-performing teams is built on trust, clarity, and shared responsibility, and for the full episode, scroll back to episode 409. ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Jac Dunne, CEO of Dimply, an AI-powered financial experience platform that’s quietly reshaping how banks, insurers and wealth managers serve their customers. After almost three decades in legacy finance, Jac made a bold move in her mid-50s into regtech and then fintech, “bookending” her career by building the kind of technology she always wished existed inside the big institutions. She breaks down what Dimply actually does in plain English, how it powers hyper-personalised journeys inside apps like AIB’s, and why the future of money will be a hybrid of human advice and seamless digital experiences. Jac also opens up about leaving a senior corporate role where her voice wasn’t being heard, taking on a startup CEO role, scaling a remote-first team, and building practical programmes to get more women and students into tech. If you’re a founder, operator or leader trying to scale something meaningful and still have a life outside of work, this conversation is packed with insight. Show Notes: In this episode, we cover: 🔥 Reinventing a 30-year career — how Jac moved from legacy finance into regtech and fintech 🚀 The Dimply origin story — why financial experiences need to be rebuilt from the ground up 📱 What Dimply actually does — a simple breakdown of the platform powering smarter banking journeys 💡 Hybrid finance — why the future blends seamless digital with instant human advice 🌍 Anticipatory banking — building for the next generation of wealth holders 🏆 Becoming a fintech CEO in her mid-50s — the moment Jac chose challenge over comfort 📈 Scaling without breaking culture — bringing structure into a fast-moving startup 👥 Leading remote-first teams — trust, energy days and the Monday pulse call 💪 Women in tech — real pathways, not panels, for returners and early-career talent ⏳ Time as a currency — leadership, parenting and designing a life that works inks & Resources Mentioned Dimply – Financial Experience Platform - https://dimply.ai Jac Dunne on LinkedIn: https://www.linkedin.com/in/jackie-jac-dunne-mba-38a50b1a/ ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

Forget the corporate polished front - authenticity wins every time. Conor McHugh, founder of Alchemy Search, shares why building a personal brand has been key to his success in Dubai, how honesty drives relationships, and why you should never pretend to be bigger than you are. 🎙️ For the full episode (412) of The Entrepreneur Experiment, listen to Conor’s full story on reputation, relationships, and building trust in business. 💡 New here? Hit follow or subscribe for weekly Mentor Moments and full founder interviews. ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1   ---  Visit my partners  Azure Communications: https://bit.ly/azureEE   Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

In this episode of The Entrepreneur Experiment, Gary sits down with Laura Dowling — “The Fabulous Pharmacist” — a pharmacist, founder, educator, entertainer, and one of Ireland’s most recognisable health voices. From 20 years behind the pharmacy counter to running a fast-growing wellness brand stocked in 1,500+ stores, Laura shares the real story behind Fabu Wellness: the failures, the stolen idea, the long nights in labs with breastfeeding babies, the near-quit moments — and the explosive online launch that changed everything. She reveals how she built a deeply engaged audience during COVID, why simplifying health information is her superpower, the truth about going viral, and how humour, honesty and empowerment built a movement behind her sell-out show Viva La Vulva. If you're a founder, creator, health professional or anyone thinking of starting something from scratch — this episode will give you courage, clarity and a reminder that nothing is ever “overnight success.” Show Notes In this episode, we cover: How Laura built her platform by simplifying health information during COVID. The power of answering real patient questions and showing up consistently online. Why humour is her secret weapon for breaking taboos in women’s health. The origin story of Viva La Vulva and how it grew into a national tour. The 12-year journey behind Fabu Wellness — including the major setback that nearly stopped her. Leaving pharmacy in 2022 to go “all in” and launching Fabu via Instagram Stories. Selling out her first launch and securing distribution with Wholefoods Wholesale. Scaling to 1,500+ stores while staying authentic and refusing fear-based content tactics. Mistakes entering the UK market — and why toning down the humour didn’t work. How she handles criticism, customer care, and running a business with her family. 🔗 Links & Resources Mentioned Fabu Wellness – https://fabuwellness.com/ The Laura Dowling Experience Podcast: https://www.youtube.com/playlist?list=PLN4xDBAAv7WCZCJ0VJC8lIXiX8_QtHFZJ ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

How does a schoolteacher from Connemara end up buying his own airline? In this Mentor Moment, Pádraig Ó Céidigh, former owner of Aer Arann, shares how instinct and courage led him to take one of the boldest entrepreneurial leaps in Irish business — remortgaging his home to keep a vital island service alive. 🎙️ Listen to the full conversation in Episode 408 of The Entrepreneur Experiment to hear Pádraig’s full story of risk, resilience, and leadership. 💡 If you haven’t already, hit follow or subscribe for more weekly founder insights and Mentor Moments. ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE  Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.

In this episode of The Entrepreneur Experiment, Gary sits down with Mark Breen, co-founder of Safe Events Global, the Irish team behind some of the world’s most ambitious events - from Dublin Zoo’s Wild Lights to Formula 1 in Qatar and mega-city festival sites across the Middle East. Mark shares the real, behind-the-scenes story of how a student “helping people up at a Frames gig” turned into running safety for shows with half a million attendees, expanding internationally, and building a 25-person specialist team that’s redefining how event safety is done. He reveals why the best events feel effortless, how the industry changed post-Covid, why “no lazy no’s” is the company philosophy, and how one email from Saudi Arabia transformed their entire trajectory. If you’re an entrepreneur who loves hearing how niche expertise becomes a global business — and how culture, clarity, and instinct can build a category-leading company — this episode is for you. Show Notes In this episode, we cover: 🔥 Mark’s unexpected journey from student security team to global event specialist 🚀 How Safe Events grew from 4 people to a 25-strong team 🔑 The game-changing first hire that accelerated their growth 🌍 The email that opened the Middle East market — and what happened next 🎪 The “invisible hand” behind the world’s best events 🦺 Why great safety is all about design, not control 🧠 The philosophy of “no lazy no’s” — and how it wins clients 💡 Why instincts matter, but structure matters more as you scale 📈 How to build long-term client relationships in a project-based industry 💻 Why Safe Events built a digital operations department and a design team ❤️ Mark’s refreshing view on success, leadership, and building a life you enjoy Links & Resources Safe Events Global: https://safeevents.ie/ Mark Breen on LinkedIn: https://www.linkedin.com/in/breenm/ ——  Subscribe to our newsletter for weekly inspiration on Business, Brain and Body, as well as exclusive events, courses and more, straight to your inbox. It's free! https://www.mrgaryfox.com/subscribe-1  ---  Visit my partners  Azure Communications: https://bit.ly/azureEE   Nostra: https://bit.ly/3HHwSMo —- Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.