The Entrepreneur Experiment

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