The Entrepreneur Experiment

In this brand-new Masterclass Special, Gary Fox sits down with Diarmuid Corcoran of Chartered Capital to unpack the money questions Irish founders avoid - until it’s too late.

They talk openly about why money can still feel like a “dirty word” in Ireland, why founders can be brilliant at making money but hesitant to manage it, and how wealth often compounds simply because of maths. Diarmuid breaks down the core principles of long-term investing (without the hype), the psychology that causes people to panic at the wrong time, and the practical founder moves that build real security - like taking a salary, using pensions properly, and keeping “fun investing” firmly contained.

If you’ve ever said “I’ll start later,” “I’ll wait for the markets to settle,” or “my business is my pension,” this episode is the reset.

Important note

This episode is education and perspective - not personalised financial advice. Always do your own due diligence and speak to a qualified advisor/accountant for your circumstances.

Show notes

• Why the “rich get richer” is often compounding in action
• Why Ireland has a unique relationship with money (scarcity mindset + property-first thinking)
• The hidden risk of “safe” cash: inflation eroding purchasing power
• Time in the market vs timing the market (and why “waiting” usually backfires)
• The psychology behind bad money decisions: recency bias, fear headlines, and the Dunning–Kruger effect
• “Set-and-forget” investing, and why boring usually wins
• The founder dilemma: all eggs in the business and no personal de-risking plan
• Pensions: why they can be tax-efficient, protective, and misunderstood
• The “de-risking” concept approaching retirement (and the 2008 lesson)
• A simple way to start investing regularly (and remove emotion from the process)
• The “playpen” rule: keeping speculative investing (stocks/crypto/startups) to a small %
• Founder mistakes Diarmuid sees constantly:
  • Not taking a salary early
  • Not paying a spouse/partner (where relevant)
  • Being far too cautious in long-term pension funds
  • Missing employer pension matching

More about Chartered Capital:

Chartered Capital Initial Query Form (https://bit.ly/4a89Mcp) for people who want to get in touch. When people fill this out, Chartered Capital will reach out to  them afterwards to arrange a meeting. They also circulate a monthly newsletter that generally only consists only of good news and isn’t ever in any way technical:  Newsletter link (https://crafty-innovator-3012.kit.com/57ab7f6ffd)

 Link to Blogs on Chartered Capital website (https://charteredcapital.ie/insights/blogs-and-news/)

Chartered Capital Website (https://bit.ly/charcap)

This is a super video on Robert Cialdini’s work for those who don’t have time to read the full book = Science of persuasion - Robert Cialdini (https://youtu.be/cFdCzN7RYbw)

The Financial Planners Ireland website: https://fpireland.ie/

Our Sponsors:

Nostra: https://bit.ly/nostra26

Azure: https://bit.ly/azure26 

Rory’s Travel Club: https://bit.ly/rorys26

Chartered Capital: https://bit.ly/49ZuFrk

Book Recommendations

General Psychology = Influence – The Psychology of Persuasion (https://amzn.to/4bB6q4c) by Robert Cialdini and The 48 Laws of Power (https://amzn.to/49XcBON)by Robert Greene.

Running a business = Traction (https://amzn.to/4qgiJGM) and Rocket Fuel (https://amzn.to/3ZdOqWa) by Gino Wickman.

Personal Finance = The Psychology of Money (https://amzn.to/4rosi7w) by Morgan Housel.

In this Mentor Moment, Keilidh Cashell shares the exact moment her career pivoted - she left her job on the makeup counter with plans to build a weekend client business… and instead, brands started reaching out with paid opportunities straight away.

Keilidh breaks down how she stayed true to her values, learned the realities of the influencer industry, and why trust and long-term partnerships matter more than a quick ad.

🎧 Want the full story? Listen to Episode 414 of The Entrepreneur Experiment for the complete conversation with Keilidh.

Our Sponsors:

Nostra: https://bit.ly/nostra26

Azure: https://bit.ly/azure26

Rory’s Travel Club: https://bit.ly/rorys26

Chartered Capital: https://bit.ly/49ZuFrk

In this episode of The Entrepreneur Experiment, Gary Fox sits down with Spencer Matthews - founder of CleanCo, endurance adventurer, and the definition of a modern founder operating across business, body and brain.

Spencer shares the real story behind his identity shift: from heavy drinking and coasting, to building extreme discipline through endurance challenges, and channeling that same intensity into building CleanCo. He opens up about raising big money, moving too fast, the U.S. expansion that didn’t land, stepping back from the day-to-day, and what he’d do differently if he was starting again.

If you’re building something and trying to balance ambition with sustainability, this one is a masterclass in reinvention, risk, and rebuilding properly.

Show Notes

In this episode, we cover:
🔥 The wake-up call that made Spencer quit drinking, and why “identity shift” beats habit change
🚀 How CleanCo started: spotting the gap in non-alcoholic spirits and going all-in with zero experience
📈 Scaling lessons: big fundraising, big valuation pressure, and the hidden cost of moving too fast
🇺🇸 The U.S. launch mistake: “no education” + rushing expansion and the 3-year cleanup
🔁 Rebuilding properly: consistency, patience, and focusing only where you can win
🏃‍♂️ Why hard challenges feel liberating, and how endurance became his operating system
🧠 How he runs life week-to-week: training, staying busy, trusting great people, and avoiding the scroll
🏝️ The long game: why he sees a future chapter in the Eden Rock family business

Links & Resources

• Spencer Matthews (Instagram): https://www.instagram.com/spencermatthews/
• CleanCo / Clean Liquor: https://www.clean.co/
• Untapped (podcast): https://open.spotify.com/search/Untapped%20Spencer%20Matthews
• James’s Place (mentioned): https://www.jamesplace.org.uk/
  
  Our Sponsors:
  
  Nostra: https://bit.ly/nostra26
  
  Azure: https://bit.ly/azure26 
  Rory’s Travel Club: https://bit.ly/rorys26
  
  Chartered Capital: https://bit.ly/49ZuFrk

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

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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/
  
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  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.

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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:

1. How Squid grew from free coffee stamps to 550,000+ users and almost 2,000 independent businesses.
2. Why Matthew & Katie focused on coffee shops to build a two-sided network from scratch.
3. Introducing Wave — “air miles for the high street” where you earn across brands automatically.
4. How card-linking with Visa/Mastercard/Amex enables one-touch loyalty.
5. The impact of integrating with Square to give independents big-brand loyalty and data tools.
6. The journey from early-stage startup to raising over €10m, including a €1.7m+ crowdfunding round.
7. The North Star metric Squid tracks: the total free product given back to users.
8. Squid’s two-step scaling playbook for Europe: launch loyalty locally, then layer Wave on top.
9. Why 2026 will be the “year of payments” as Squid builds a rewards-driven payment rail.
10. 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

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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.

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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/

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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.

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Music Credit: “Nobody Knows” by Andrew Applepie — used under royalty-free license.