I Made $50M Buying & Running Boring Businesses

This podcast episode interviews Brent Beshore, founder of Permanent Equity, about his journey in acquiring and managing a portfolio of 16 companies generating over $350 million in annual revenue. The conversation starts with Beshore's accidental acquisition of his first business and details his path to raising significant capital, his unique investment strategy (all-cash deals, no debt, long-term hold), and his high rate of return. Beshore emphasizes the importance of finding the right operators, using personality assessments (DISC, Myers-Briggs, Enneagram), and shares his philosophy of either operating with high authority or delegating completely, avoiding the middle ground. Listeners gain insights into Beshore's unconventional approach to private equity and practical advice on identifying and acquiring successful businesses.

Outlines

Part 1: Introduction to Brent Beshore and Permanent Equity

Part 2: Investment Strategy and Structure

Part 3: Beshore's Skills and Practical Advice

Part 4: One-Liners and Business Insights

Part 5: Evaluating Businesses and People

Part 6: Conclusion

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My First Million

Part 1: Introduction to Brent Beshore and Permanent Equity

Introduction and Brent Beshore's Success

Beshore's Portfolio and the "Golden Goose" Concept

MediaCross: The First Golden Goose

The Accidental Acquisition of MediaCross and SBA Loans

Just-in-Time Learning and Early Mistakes

Subsequent Acquisitions and the Importance of Long-Term Perspective

Part 2: Investment Strategy and Structure

Securing $50 Million in Funding

Permanent Equity's Unique Investment Structure

The Rationale Behind Avoiding Debt

Investment Returns and Benchmarking Against the S&P 500

Permanent Equity's Investment Performance and Market Inefficiencies

Risk Tolerance and Early Success

Warren Buffett's Early Investments: Sanborn Maps and Dempster Mill

Part 3: Beshore's Skills and Practical Advice

Beshore's Key Skills and Investment Approach

Investing to Retire a Sister: Initial Steps

Advice on Buying a First Business

Part 4: One-Liners and Business Insights

One-liner Discussion: "All businesses are loosely functioning disasters."

One-liner Discussion: "The more humility a leader has, the more their business can grow."

One-liner Discussion: EBITDA vs. Bullshit Earnings

The History and Critique of EBITDA

One-liner Discussion: "You either operate with high authority, top down, or delegating authority. Hell is in the middle."

The Importance of Incentivizing Managers and Scaling Leadership

Part 5: Evaluating Businesses and People

Market Selection, CEO Quality, and Luck in Business Success

Evaluating CEOs and Utilizing Personality Assessments

The "Asshole Test" and Identifying Character

Part 6: Conclusion

Conclusion and Call to Action

I Made $50M Buying & Running Boring Businesses

My First Million

Part 1: Introduction to Brent Beshore and Permanent Equity

00:00Introduction and Brent Beshore's Success

Introduction and Brent Beshore's Success

02:03Beshore's Portfolio and the "Golden Goose" Concept

Beshore's Portfolio and the "Golden Goose" Concept

03:41MediaCross: The First Golden Goose

MediaCross: The First Golden Goose

05:54The Accidental Acquisition of MediaCross and SBA Loans

The Accidental Acquisition of MediaCross and SBA Loans

09:16Just-in-Time Learning and Early Mistakes

Just-in-Time Learning and Early Mistakes

11:27Subsequent Acquisitions and the Importance of Long-Term Perspective

Subsequent Acquisitions and the Importance of Long-Term Perspective

Part 2: Investment Strategy and Structure

13:47Securing $50 Million in Funding

Securing $50 Million in Funding

15:21Permanent Equity's Unique Investment Structure

Permanent Equity's Unique Investment Structure

18:04The Rationale Behind Avoiding Debt

The Rationale Behind Avoiding Debt

20:16Investment Returns and Benchmarking Against the S&P 500

Investment Returns and Benchmarking Against the S&P 500

22:33Permanent Equity's Investment Performance and Market Inefficiencies

Permanent Equity's Investment Performance and Market Inefficiencies

24:19Risk Tolerance and Early Success

Risk Tolerance and Early Success

25:31Warren Buffett's Early Investments: Sanborn Maps and Dempster Mill

Warren Buffett's Early Investments: Sanborn Maps and Dempster Mill

Part 3: Beshore's Skills and Practical Advice

28:45Beshore's Key Skills and Investment Approach

Beshore's Key Skills and Investment Approach

31:17Investing to Retire a Sister: Initial Steps

Investing to Retire a Sister: Initial Steps

33:14Advice on Buying a First Business

Advice on Buying a First Business

Part 4: One-Liners and Business Insights

36:18One-liner Discussion: "All businesses are loosely functioning disasters."

One-liner Discussion: "All businesses are loosely functioning disasters."

37:02One-liner Discussion: "The more humility a leader has, the more their business can grow."

One-liner Discussion: "The more humility a leader has, the more their business can grow."

38:41One-liner Discussion: EBITDA vs. Bullshit Earnings

One-liner Discussion: EBITDA vs. Bullshit Earnings

40:36The History and Critique of EBITDA

The History and Critique of EBITDA

43:35One-liner Discussion: "You either operate with high authority, top down, or delegating authority. Hell is in the middle."

One-liner Discussion: "You either operate with high authority, top down, or delegating authority. Hell is in the middle."

44:46The Importance of Incentivizing Managers and Scaling Leadership

The Importance of Incentivizing Managers and Scaling Leadership

Part 5: Evaluating Businesses and People

47:31Market Selection, CEO Quality, and Luck in Business Success

Market Selection, CEO Quality, and Luck in Business Success

50:32Evaluating CEOs and Utilizing Personality Assessments

Evaluating CEOs and Utilizing Personality Assessments

54:08The "Asshole Test" and Identifying Character

The "Asshole Test" and Identifying Character

Part 6: Conclusion

58:53Conclusion and Call to Action

Conclusion and Call to Action