Lessons from 40 years leading a family business with Michael O’Reilly

The Grounded Man

The Grounded Man
Lessons from 40 years leading a family business with Michael O’Reilly
Sep 04, 2026
John Douglas

How do you grow a family business without losing the values that built it?

In this episode, John is joined by Michael O’Reilly, second-generation Managing Director of Pneumatics Group, for a walk-and-talk about his four decades in the family business. Michael reflects on its humble beginnings, why holding stock became a competitive advantage, and how learning every part of the company has been both a strength and a challenge.

Michael also shares the story of buying the business from his dad, navigating recessions and difficult family moments, and the important role his mam played in creating the heart and energy of the company. He explains why reputation, trust, and looking after people have remained central to how the family leads and grows the business.

John and Michael also explore the value of outside support, the impact of working with Deru, and how greater clarity and accountability have helped Michael focus on the areas where his time matters most. Michael discusses achieving the company’s most profitable years in decades, making decisions with greater confidence, and creating more space for his family and life outside the business.


Interested in joining our next Grounded Man Hike? Click here for more: https://www.derunation.com/TGM-Hike


00:01:48 — Introducing Pneumatics

00:04:31 — The Early Days

00:05:43 — Why Holding Stock Pays

00:06:44 — Taking More Responsibility

00:08:08 — Knowing Everything: A Strength or Weakness?

00:11:43 — Reputation Is Our Goal

00:12:09 — Reputation Pays

00:14:11 — Being the Conscience of the Company

00:17:31 — Building a Brand

00:18:20 — Buying the Business Off Dad

00:21:42 — Overcoming Challenges as a Family

00:25:57 — The Role Our Mam Played

00:30:56 — Getting Support to Lead and Grow

00:33:23 — Working with Deru

00:41:16 — The Most Profitable Years in Decades

00:43:34 — Growing with Confidence

00:45:36 — How Michael Leads Outside the Business

00:49:05 — The Deru Mechanism

00:50:13 — What Surprised Michael About Deru

00:52:13 — What Michael Is Most Excited About 



Episode Artwork Lessons from 40 years leading a family business with Michael O’Reilly 57:34 Episode Artwork If you don't take the time, you won't have the energy 17:00 Episode Artwork How a hike can grow your business 15:19 Episode Artwork Success is being in my best energy everyday - Sam Harte 51:01 Episode Artwork Growing your business – and freedom – by growing your people. 21:14 Episode Artwork Does your business Revolve around you – or Run without you? 22:14 Episode Artwork Why can't they just get it — is it them or is it me? 22:14 Episode Artwork Letting go to get your energy back - with Barry Finnegan 43:14 Episode Artwork If There's Not Enough Hours in the Day — You're Counting Them Wrong 24:35 Episode Artwork Your financial pressure has nothing to do with money 22:33 Episode Artwork Am I the only one that cares about the business? 16:40 Episode Artwork Running on empty - or just dirt in the fuel line? 21:13 Episode Artwork Why It's So Hard To Not Doubt Yourself 21:19 Episode Artwork Doing everything you can and still feeling like it’s not enough 18:53 Episode Artwork If the business owns you – it’s time to own yourself. 20:03 Episode Artwork If you can't switch off - switch on 17:47 Episode Artwork Taking the work out of life with Ross Griffin 31:32 Episode Artwork Enjoy the build - Look forward to Mondays again 17:54 Episode Artwork How To Lead with Freedom When Pressure is Constant 20:25 Episode Artwork Carrying the weight without losing yourself 17:35 Episode Artwork Leading By Example Starts With Your State 17:33 Episode Artwork Stop Working to Earn Freedom — Lead With Freedom 21:03 Episode Artwork The Hardworking Man: Old Strength in a New World 15:01