The Entrepreneurial Odd Couple

Two Hosts. Zero in Common. Ten Questions. Entrepreneurial Odd Couple is the podcast where an introvert and an extrovert sit down with business owners who’ve actually built something — and ask the questions that get past the highlight reel. Every episode, we sit down with a business owner and ask the same ten questions — the ones that cut through the “hustle culture” highlight reel and get to what actually happened. How they started. What broke them. What they’d do differently. What they’re genuinely proud of. One of us will ask the quiet, thoughtful follow-up. The other will say the thing everyone’s thinking. Somewhere in the middle, you get an hour that’s honest, a little unpredictable, and packed with ideas you can actually use.

Episodes

Latest Episodes

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Oct 1, 2026

1 hr 18 min

Julian Hughes of Gatewen Training shares his journey from a council estate to building training businesses, rescuing a long-standing company, and creating life-changing programs that help people gain practical, work-ready skills.
He discusses entrepreneurship, the importance of apprenticeship-style training like forklift and HGV, the value of purpose and mental health, and small habits that improve performance — showing how focused support, collaboration, and persistence can transform lives and communities.

Oct 1, 2026

1 hr 18 min

Sep 24, 2026

53 min

In this episode Dawn Morris shares her journey from early retail and finance roles to founding Dawn Morris Consultancy, focusing on finance, operations and strategy for charities and social enterprises. She discusses key lessons learned — the dangers of spreading yourself too thin, the power of reputation and networks, and practical habits and tools that help leaders perform.Dawn also talks about her community projects (including the Mandela 8 regeneration and youth programs), the launch of Legal Tech Live, and why values-driven choices matter in business. For contact she points listeners to LinkedIn.

Sep 24, 2026

53 min

Sep 18, 2026

1 hr 1 min

In this episode with sit down with Katherine Jones who has ThinK Wine Group, The National Influencer Awards and We Are SN.
She has a great story to tell, she also went viral not long after this was filmed. Thank you for your time with us Katherine, we really enjoyed it!

Sep 18, 2026

1 hr 1 min

Sep 14, 2026

44 min

In this episode hosts Jamie and the co-host interview Peter Buglass of Director School about his journey from business failure to helping company directors sharpen leadership, make better decisions, and protect their personal assets. They discuss common director mistakes—especially misconceptions about limited liability—how to turn failure into learning, and practical governance and planning tips.
Peter also describes his charity work with refugees at climbing walls and shares actionable habits: listen to understand, define ethics and values, pick the blue paint (avoid over‑debating small things), and ask for help early—plus why Director School is a valuable resource for new and experienced directors.

Sep 14, 2026

44 min

Sep 4, 2026

47 min

In this episode Oli Clarke, Managing Director of the 35-year-old BaaBar Group, shares his journey from working behind the bar to Managing Director and how the family-owned hospitality business reinvented its venues in Liverpool. He explains why scaling back from 15 sites to three increased profitability and how strategic refurbs and new concepts (BaaBar, De Lucas, Frederick’s, and the Orbit room) revived the brand.
Oli discusses leadership in a family business, the importance of culture and atmosphere, staffing and time-management lessons, industry pressures like VAT and new parking restrictions within the Liverpool area, as well as plans to expand regionally over the next few years.

Sep 4, 2026

47 min

Aug 28, 2026

35 min

We sit down with Kris Ali from Ark Technology Group. We discuss everything from how he got started in business, the challenges he's faced along with how he has dealt with them. This is a fantastic episode for any business owner who is unsure about IT Security, Kris gives some excellent insight into projects he has worked on and some of the things he has seen when companies IT security hasn't been robust.

Aug 28, 2026

35 min