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

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The Deal Flow Show

Ivan Acuna

14 episodes

1 day ago

The Deal Flow Show is where private equity gets real. No scripted answers, no corporate fluff—just raw, unfiltered conversations with the top dealmakers in the game. We pull back the curtain on the industry, sharing the stories, strategies, and hard-earned lessons that you’d normally only hear behind closed doors. Whether you’re deep in the world of M&A or just starting to navigate private markets, this is where you get the insights, mentorship, and war stories that actually matter.

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

The Deal Flow Show

55 minutes 16 seconds

4 months ago

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

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