The Entrepreneur Experiment

What doesn’t disappear in a recession? Money. What disappears is confidence — and that’s where opportunity lives.

In this episode of The Entrepreneur Experiment, Gary sits down with Ray Ryan, founder of The Noledge Group, for a wide-ranging, founder-first conversation on staying relevant through decades of tech change — from mainframes, to PCs, to cloud… and now AI, agents, and wearables.

Ray shares how he’s built and evolved a business by spotting shifts early, testing relentlessly, and focusing on what actually creates productivity (hint: it’s not hype — it’s time saved). They get into why voice + visual is the real unlock, how agentic AI changes the game, why the keyboard era is ending, and the simple human rule behind adoption: benefit must outweigh friction.

This is a practical, honest conversation about how founders survive (and win) through change — and why systems, experimentation, and enthusiasm matter more than ever.

In this episode:

Why recessions are really confidence cycles (and where opportunity comes from)

Tech cycles: mainframe → network/PC → cloud → AI

The next shift: wearables + edge computing + AI agents

Why voice is the “unlock” (and keyboards are on the way out)

Business is experimentation: testing, packaging, and customer psychology

Scaling through acquisitions — and why “audience” matters in business

Ray’s best advice: cash flow and enthusiasm (and why enthusiasm wins

About the guest

Ray Ryan is the founder of The Noledge Group, working with businesses on improving how they run finance and operational systems—helping leaders move from messy, manual workflows to clearer reporting and stronger decision-making.

Links & resources

The Noledge Group: https://noledge.ie/

Ray Ryan (LinkedIn): linkedin.com/in/rayryanossm

Power Law of Podcasting (course): https://stan.store/garyfox/p/the-podcasting-power-law

Our Sponsors

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Azure: https://bit.ly/azure26 

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

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

Follow & support the show

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In this weekend’s Mentor Moment, Charlene Flanagan and Niamh Ryan - the founders of Ella & Jo - share a refreshing take on what success really means. Instead of chasing someone else’s version of the win, they talk about defining success for yourself: freedom, family time, building from the west of Ireland, and creating a legacy by bringing a brand from “nothing” to customers in over 50 countries.

If you’ve ever felt swept up in external pressure - the numbers, the milestones, the “next thing”- this clip is your reminder to pause, reassess, and choose what you actually want your life to look like.

For the full conversation with Charlene and Niamh, listen to Episode 417 of The Entrepreneur Experiment.

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 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

What you’ll learn

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