Ian Rickwood, Founder and CEO of Henley Group, has quietly deployed $4B+ across US and Europe, built and sold food chains, and is now rolling up US car washes using AI-driven site selection. We also dive into what great operator partners look like, how to handle bad deals, and what it’s really like to build a serious firm with your spouse and kids.

TIMESTAMPS:
0:00 “Don’t give up” Ian’s core lesson on entrepreneurship and resilience
0:34 Who is Ian Rickwood and what is Henley Group?
1:04 The scale of Henley today: capital, sectors, and strategy
3:02 Early career: Procter & Gamble and Pepsi
5:02 Discovering Subway & winning the master franchise
7:04 “More margin in the lease than in the sandwich” real estate awakening
11:01 From 17 Subways to buying Benjys
13:03 Scaling Benjys to 90 stores + ~200 ‘vanchises’… then getting crushed
15:05 A tough exit and what it taught Ian
17:04 Starting Henley from lifestyle dev to serious platform
19:03 Surviving the GFC and pivoting the model
21:03 A 12-year run and Henley’s track record
22:07 Building a firm with your spouse “colors and numbers”
25:08 Bringing the kids into the business (without ruining them)
29:04 Dealing with bad deals and problem assets
31:02 Geographic expansion Holland, Germany, Poland, Ireland
33:06 Entering the US and timing the exit
33:56 From deal-by-deal to first fund
37:03 “It’s all about the deal” capital vs conviction
40:13 Sponsor: Capitalpad marketplace for acquisition deals
41:20 What a perfect operator/entrepreneur partner looks like
43:03 Reading people in a 60-minute meeting
45:02 Why car washes? Entering a ‘boring’ but beautiful business
47:03 The failed first platform: overpaying, over-spending, bad sites
48:00 Rebuilding from scratch: launching Aquasonic the right way
49:02 Data, AI and picking car wash sites
52:05 The most expensive beliefs Ian has changed
55:11 Big-picture lessons keep learning, don’t give up, pivot fast
57:17 Favorite books and how Ian unwinds
57:47 Closing thoughts and wrap-up 

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This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.