This week, I sat down with Ian Rickwood to unpack a career that spans entrepreneurship, private equity, consumer businesses, failed exits, market downturns, and ultimately the building of a long term real estate investment and capital platform.

Ian is Founder and Chairman of Henley, a fast growing private equity real estate investment and venture capital business operating across the UK, Europe and the US. Over the last two decades, Henley has invested across residential, industrial, social and supported housing, urban regeneration and large scale development, working with institutional capital, high net worth investors and operating partners.

In this conversation, Ian shares how early years in FMCG and entrepreneurial ventures laid the foundations for his approach to risk and execution, why scaling consumer businesses taught him lessons that many investors only learn later, and how navigating both successful exits and painful failures shaped his long term mindset. We discuss what it really feels like when a deal does not work, why some businesses are structurally broken regardless of management quality, and how those experiences directly influenced Ian's transition into real estate and private capital.

Ian also explains how Henley was formed out of operational experience rather than financial engineering, why long dated and complex projects can offer an edge, and how the firm thinks about platform building, partnerships and capital alignment. We explore social and supported housing, urban regeneration at scale, the challenges of deploying capital through cycles, and why conviction becomes more important as markets tighten. The conversation also touches on US expansion, joint venture models, and what experienced operators look for when backing people rather than just projects.

Key Topics Covered in This Episode

✅ From Operator to Investor

How early entrepreneurial and operating experience shaped Ian's approach to capital, risk and decision making.

✅ When Exits Do Not Go to Plan

Why some businesses fail despite strong management and what those lessons teach long term investors.

✅ Building Henley Through Cycles

How private equity thinking, real estate fundamentals and operational discipline came together.

✅ Complexity as a Competitive Advantage

Why long dated, operationally intensive and misunderstood assets can outperform.

✅ Capital, Partnerships and Conviction

How Henley approaches joint ventures, institutional capital and platform growth across markets.

And of course, I asked Ian the big question:

Who are the People, what Property, and which Place would you invest in if you had £500 million to deploy?

If you have thoughts or questions about this episode, drop them in the comments. I'd love to hear your take.

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