The Deal Flow Show

I Interviewed 45 Billionaires… Here’s How They Got Rich


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In this episode, Richard C. Wilson explains how he built the world’s largest family office network by focusing on value, positioning, and long-term niche domination. From owning FamilyOffices.com to interviewing 45 billionaires, he breaks down mental models, marketing strategy, and how to win exclusive deal flow. If you run a fund, raise capital, or want access to better deals, this episode shows what it takes to play at the highest level.Sign up to our newsletter: https://offmarketmemo.beehiiv.com/ 00:00 Intro to Richard C. Wilson01:36 What FamilyOffices.com actually does03:18 How he discovered the family office world06:15 What problems family offices actually have08:50 Breaking down family offices like a 5th grader13:03 Dealing with ultra-wealthy while broke16:12 Why trust beats pitch decks18:45 The power of cognitive dissonance22:05 What truly drove him to build wealth25:32 The risk he took that changed everything28:44 How he made $35,000 in a single day30:40 Why he bought FamilyOffices.com33:21 How he used blogging and SEO to launch35:44 Marketing mentors and the choke point strategy39:18 Why finance people are terrible marketers41:32 How his AI tools help fix that44:40 Why family offices often have bad deal flow48:15 Positioning = better deal flow50:29 How media and distribution became his moat54:20 The deal structure tool that changes the game57:42 What the best family offices are doing differently59:41 Strategic acquisitions to remove bottlenecks01:02:40 The billionaires.com play and trifecta moat01:07:01 What billionaires do differently than millionaires01:10:35 How long-term niche focus compounds01:12:58 Don’t wait for permission — publish01:14:04 How far behind are PE and family offices, really?01:18:00 The biggest mistake family offices make01:21:20 His #1 quote from billionaire interviews01:24:06 Richard’s 10-year vision

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The Deal Flow ShowBy Ivan Acuna