ScaleX™ Insider Podcast

Long-Term Business Growth: Jeremy Middleton on Thinking in Decades

ScaleX™ Insider Podcast

Show Notes

What does it really take to build a business that can keep growing for decades? In this episode of ScaleX Insider, Brendan McGurgan is joined by Jeremy Middleton, co-founder of HomeServe and founder of Middleton Enterprises, to explore what long-term business growth looks like from someone who has experienced it first-hand. Jeremy co-founded the business that would become HomeServe alongside Sir Richard Harpin, beginning a journey that would span around 30 years and ultimately create a multi-billion-pound business. But Jeremy's role in that journey was different from Richard's. As HomeServe developed, Jeremy recognised that Richard was the stronger operator. Rather than competing for the CEO position, they adapted their partnership, allowing each of them to focus on where they could create the most value. It's a lesson Jeremy has carried into his work as an investor today: know what you're good at, know what you're not, and build around those strengths. Jeremy and Brendan explore what founders need to prove before a business is genuinely ready to scale. For Jeremy, it starts with the economics. The business needs to generate cash, the model needs to be repeatable, there needs to be a genuine competitive edge, and the founder needs a sensible plan for growth. And believing those things isn't enough. You need evidence. The conversation also challenges the pressure many entrepreneurs feel to grow faster, enter new markets or raise significant external capital. Jeremy explains why he often finds himself encouraging founders to do the opposite: get the existing model right, prove it works repeatedly and then keep building on it. Because many businesses don't realise their true potential in three or five years. They do it after ten, twenty or even thirty. Jeremy also shares his perspective on raising external capital, why giving away equity too early can become incredibly expensive, and why founders should be clear about exactly what they need the money for before bringing an investor into the business. They also explore what happens when the founder's personal needs begin to change. Taking some money off the table doesn't necessarily mean selling the business. And stepping away from day-to-day operations doesn't mean walking away from what you've built. By separating the business, your ownership and your role within it, Jeremy believes founders can create more freedom while still allowing the business to compound over the long term. Ultimately, Jeremy's approach to scaling is remarkably simple: build something that works, stay focused on it and give it enough time to reach its potential. Timestamps 00:00 – Introduction: Jeremy Middleton 00:37 – What Scaling With Purpose Really Means 03:24 – Knowing Your Strengths as a Founder 07:00 – When the Founder Should Step Back 13:54 – Building Successful Business Partnerships 19:14 – Confronting the Brutal Facts 25:10 – Scaling From £100 Million to £1 Billion 30:09 – How to Know When a Business Is Ready to Scale 35:13 – Think in Decades, Not Years 40:00 – Building Long-Term Compounders 45:04 – When Should You Take External Investment? 50:29 – Where Promising Businesses Break During Scale 53:00 – Taking Money Off the Table Without Exiting 56:33 – Think More and Do Less 58:06 – Jeremy Middleton's Three Timeless Takeaways 60:15 – What's Next for Middleton Enterprises About Jeremy Middleton Jeremy Middleton is the Founder and CEO of Middleton Enterprises, a family office he established in 2000 to help entrepreneurs scale SMEs. He works with the team on new investment decisions while supporting businesses across the existing portfolio to develop winning strategies. Jeremy is also the co-founder of HomeServe, where he worked alongside Sir Richard Harpin during its scaling journey. Connect with Jeremy Middleton Website: Middleton Enterprises LinkedIn: Jeremy Middleton ScaleX / Simple Scaling Book: Simple Scaling: 10 Proven Principles to 10x Your Business

More from ScaleX™ Insider Podcast

Oct 23, 2026

SME leadership lessons become useful when you can put them into practice. In this clip from the ScaleX Insider Season 21 wrap-up, Brendan McGurgan and Claire Colvin revisit Guy Kawasaki's framework for creating a product or service that is both unique and valuable, Stephen Rogelberg's advice on better meetings, and JL Holdsworth's insights on how we respond to pressure. Claire also shares what she wants to bring into Simple Scaling's own team, from turning meeting agendas into questions to agreeing which business problems AI could help solve. Practical reflections for SME leaders looking to strengthen their proposition, make meetings more productive and lead with greater calm. Scaling your business brings plenty of questions. Are your meetings helping people move forward? Where could AI make a useful difference? And how do you keep learning while managing the demands of leadership? In this Season 21 wrap-up of ScaleX Insider, Brendan McGurgan and his business partner, Claire Colvin, revisit the guests, conversations and practical insights that stood out across the season. For SME leaders with full diaries and ambitious plans, there is plenty to take back into the business. From Stephen Rogelberg's insights on better meetings to Paul Cheek's guidance on exploring and implementing AI, Brendan and Claire reflect on ideas that can help leaders rethink how they spend their time and approach growth. They also look back on Brendan's conversation with Silicon Valley legend Guy Kawasaki—a guest whose work first influenced him 26 years ago, while he was helping to scale a software company. Getting Guy onto the podcast took 18 months, several reschedules and one memorable misunderstanding about "PT". In this episode: Brendan and Claire share their reflections on Season 21 and its variety of guests.

Oct 23, 2026

AI for SMEs starts with a clear question: what problem are you trying to solve? In this clip from the ScaleX Insider Season 21 wrap-up, Brendan McGurgan and Claire Colvin reflect on Paul Cheek's advice on adopting AI. Claire shares how her own frustrations with technology have shaped her approach, and why identifying three to five business challenges with the team could give AI experimentation a useful focus. A practical conversation for SME leaders looking to reduce operational friction, improve customer experience and give their teams a clear place to start with AI. Scaling your business brings plenty of questions. Are your meetings helping people move forward? Where could AI make a useful difference? And how do you keep learning while managing the demands of leadership? In this Season 21 wrap-up of ScaleX Insider, Brendan McGurgan and his business partner, Claire Colvin, revisit the guests, conversations and practical insights that stood out across the season. For SME leaders with full diaries and ambitious plans, there is plenty to take back into the business. From Stephen Rogelberg's insights on better meetings to Paul Cheek's guidance on exploring and implementing AI, Brendan and Claire reflect on ideas that can help leaders rethink how they spend their time and approach growth. They also look back on Brendan's conversation with Silicon Valley legend Guy Kawasaki—a guest whose work first influenced him 26 years ago, while he was helping to scale a software company. Getting Guy onto the podcast took 18 months, several reschedules and one memorable misunderstanding about "PT". In this episode: Brendan and Claire share their reflections on Season 21 and its variety of guests.

Oct 21, 2026

Scaling your business brings plenty of questions. Are your meetings helping people move forward? Where could AI make a useful difference? And how do you keep learning while managing the demands of leadership? In this Season 21 wrap-up of ScaleX Insider, Brendan McGurgan and his business partner, Claire Colvin, revisit the guests, conversations and practical insights that stood out across the season. For SME leaders with full diaries and ambitious plans, there is plenty to take back into the business. From Stephen Rogelberg's insights on better meetings to Paul Cheek's guidance on exploring and implementing AI, Brendan and Claire reflect on ideas that can help leaders rethink how they spend their time and approach growth. They also look back on Brendan's conversation with Silicon Valley legend Guy Kawasaki—a guest whose work first influenced him 26 years ago, while he was helping to scale a software company. Getting Guy onto the podcast took 18 months, several reschedules and one memorable misunderstanding about "PT". In this episode: Brendan and Claire share their reflections on Season 21 and its variety of guests.

Oct 16, 2026

What makes someone truly remarkable? Is it their success, their personality, or the impact they leave behind? In this 5-minute clip from ScaleX Insider, Brendan McGurgan speaks with Guy Kawasaki about his experience working with Steve Jobs and what separates remarkable leaders from the rest. Guy shares his candid perspective on Jobs' brilliance and difficult personality, explains why Canva founder Melanie Perkins proves that success doesn't require being difficult to work with, and challenges the idea that remarkability can be judged by a single moment. His message? Being remarkable isn't about copying successful people. It's about the body of work you build over time. Listen to the clip for a fascinating perspective on Steve Jobs, leadership and what it really means to be remarkable. 00:00 – What makes someone truly remarkable? 00:30 – Steve Jobs and Jane Goodall: Two remarkable individuals 01:05 – Steve Jobs: Brilliant genius or difficult leader? 02:00 – Melanie Perkins and why success doesn't require being difficult 02:45 – Why copying Steve Jobs won't make you successful 03:45 – Can you recognise remarkable leadership in a single moment? 04:40 – Why remarkability is measured by a lifetime of work About Guy Kawasaki Guy Kawasaki is the chief evangelist of Canva and a former chief evangelist of Apple, where he played an influential role in the marketing of the Macintosh. He is the author of 19 books, including Think Remarkable, The Art of the Start and Rules for Revolutionaries, and hosts the Remarkable People podcast. Through his writing, speaking and podcasting, Guy shares insights on innovation, entrepreneurship, leadership and making a meaningful difference. Connect with Guy Kawasaki: Website: https://guykawasaki.com/ Substack: https://guykawasaki.substack.com/ ScaleX / Simple Scaling 📊 Free Diagnostic – Score Your Business Across the 10 Principles of Scaling https://scalexaccelerator.simplescaling.com/scalex-10p-scaling-diagnostic ⚡ ScaleX Accelerator (over £3M revenue) – Register Here https://scalexaccelerator.simplescaling.com/sx-programme-application 🚀 ScaleX Elevate (under £3M revenue) – Register Here https://simplescaling.com/solutions/scalexelevate-scale-up-coaching/ 📘 Book: Simple Scaling: 10 Proven Principles to 10x Your Business 🌐 Website https://simplescaling.com ✉️ Email [email protected] 💼 LinkedIn https://www.linkedin.com/company/simple-scaling 📸 Instagram https://www.instagram.com/simple_scaling ▶️ YouTube https://www.youtube.com/@simplescaling

Oct 16, 2026

What if the secret to scaling your business is to stop worrying about scaling? In this 7-minute clip from ScaleX Insider, Brendan McGurgan speaks with Guy Kawasaki, former Apple chief evangelist and current Canva chief evangelist, about what businesses should focus on before pursuing growth. Guy explains why doing things that don't scale is often essential to winning your first customers, why smaller businesses have an advantage when experimenting with new ideas, and how his simple two-by-two framework can help entrepreneurs create something both unique and valuable. Using Apple's iPod as an example, he reveals why differentiation alone isn't enough. Your product or service must also deliver something customers genuinely value. The key message? Before figuring out how to scale, make sure you've built something worth scaling. Timestamps 00:00 – Why great products and word of mouth come first

See all episodes →