EE473 - 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

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