Ian Rickwood on AI, Private Equity, Car Wash & Real Estate Investing | Henley Group

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Nov 14, 2025

Ian Rickwood, Founder and CEO of Henley Group, has an impressive track record deploying over $4 billion in private equity and real estate. He dives into scaling successful businesses, from car washes to food chains, and the importance of site selection using AI. Ian shares insights on partnership dynamics with his spouse and children while emphasizing resilience in entrepreneurship. He candidly discusses handling tough deals and what traits make a great operator partner, all while learning from past successes and failures.

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ADVICE

Persist And Pivot

Don't give up when starting a business; persistence matters more than instant success.
Expect several failures and pivot quickly rather than quitting early.

ANECDOTE

Real Estate Beat Sandwich Margins

Ian discovered real estate upside while leasing Subway stores and saw yield compression boost asset values.
He found buying the leased store produced much faster capital gains than selling sandwiches.

ANECDOTE

Rapid Expansion Then A Tough Exit

Ian grew Benjys from ~28 to ~90 stores and added ~200 mobile 'vanchises' before a tough sale in 2006.
Supermarket competition and rising rents caused revenue drops that turned profits into losses.

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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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