Fireside Chat with Kent Clothier

2 Feb 2026 · 87 min
Episode

2 Feb 2026 · 87 min

0:00

Kent Clothier built a $1.8B company by 30, lost it all, then pivoted to real-estate wholesaling. He now does 500 wholesale deals yearly across 11 markets through a deal-flow engine powered by education, software, and the Boardroom Mastermind. His tactics: personalized video mailers, light-touch Typeforms to capture seller leads, and a mortality calculator that multiplies remaining days by waking hours to push action.

Questions this episode answers

2012

~$50 million/year by age 23; ~$800 million/year by age 28; ~$1.8 billion by age 30

He says he taught about 60,000 people and the community software has about 15,000 paying customers

Wholesale/paper deals: ~500/year; houses bought/rehabbed/flipped or sold to investors: ~1,000/year across ~11 markets; single-family houses managed: ~8,000; capital raised: ~$200 million

Chapters

More from Ryan

48:37
Podcast

The Estate Planning Mistake That Tears Families Apart (Jimmy Buffett's $275M Lesson)

4w ago
26:35
Podcast

Retire Early or Live Fully? The FIRE Debate

1mo ago
38:25
Podcast

From Passion Project to Corporate Casualty: The TNC Saga

1mo ago
48:51
Podcast

How Equity Consulting Can 10X Business ROIs

1mo ago
21:50
Podcast

Can You Build a Business for Both Cash Flow and a Big Exit?

1mo ago
51:12
Podcast

Why 75% of Founders Regret Selling (and How to Exit Without Losing Yourself)

2mo ago
39:01
Podcast

When to Let the Dumpster Fire Burn (and Why AI Is Breaking Hiring)

2mo ago
43:18
Podcast

SEO vs AEO: What Every Business Needs to Know

3mo ago
20:09
Podcast

Breaking Free from Founder Identity Debt

3mo ago
36:33
Podcast

Micro CEOs: The Future of Agile Business Teams

3mo ago
PodcastUnlocking AI's Potential: Practical Strategies for Entrepreneurs
Podcast

Unlocking AI's Potential: Practical Strategies for Entrepreneurs

4mo ago
See all content