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PodMine
Founders
Founders•October 28, 2025

My Conversation with Brad Jacobs

David Senra interviews Brad Jacobs about his entrepreneurial journey, discussing his approach to building businesses, the importance of recruiting top talent, embracing technology, and maintaining a positive mindset while continuously learning and improving.
Corporate Strategy
Startup Founders
Venture Capital
David Senra
Brad Jacobs
Ludwig Jesselson
Fred Smith
FedEx

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

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Podcast Summary

This episode of "David Senra" features an in-depth conversation with serial entrepreneur Brad Jacobs, who has built eight separate billion-dollar companies over his four-decade career. (00:56) The discussion covers Jacobs' unique approach to business building, his philosophy on problems and opportunities, and the crucial lessons he learned from mentors like Ludwig Jesselson. (02:14) Key topics include his systematic approach to company building, the importance of recruiting exceptional talent, and his methods for maintaining high-performance teams through innovative compensation structures and meeting methodologies.

  • Main Theme: Brad Jacobs shares his proven methodology for building billion-dollar companies, emphasizing the critical importance of embracing problems as opportunities, recruiting A-players, and maintaining long-term relationships built on integrity and mutual benefit.

Speakers

David Senra

David Senra is the host of the acclaimed "Founders" podcast, where he has obsessively studied over 400 biographies of history's greatest entrepreneurs for nearly a decade. He has now launched a new show called "David Senra" featuring conversations with the greatest living founders.

Brad Jacobs

Brad Jacobs is a serial entrepreneur who has built eight separate billion-dollar companies over his four-decade career, including United Rentals and XPO Logistics. He's the author of "How to Make a Few Billion Dollars" and is known for his systematic approach to industry consolidation and value creation through disciplined acquisitions and operational improvements.

Key Takeaways

Embrace Problems as Your Greatest Opportunities

Brad learned from his mentor Ludwig Jesselson that "business is problems" and successful entrepreneurs should run toward challenges, not away from them. (04:55) Jesselson taught him that problems are how you make money - the more problems you can solve, the more value you create. This perspective transforms how you view setbacks and obstacles, seeing them as pathways to success rather than roadblocks. Brad emphasizes that if you're going to get beaten down by problems, you won't be successful or happy in business.

Get the Major Trend Right

One of the most important maxims Brad learned from Ludwig Jesselson is to "get the major trend right." (03:03) As a commodity trader, Jesselson understood that you could do thousands of things correctly, but if you missed the major trend, you'd still fail. Brad applies this by looking at long-term technological and societal trends when selecting industries to enter, ensuring he's building businesses that align with where the world is heading rather than fighting against inevitable change.

Recruit Superlative People Above All Else

Brad considers recruiting top talent the CEO's most important job, stating "there's no substitute for smarts." (51:14) He uses a mental exercise where he visualizes each team member quitting - if his reaction is pure terror and panic, that's an A-player he can't afford to lose. He deliberately seeks people smarter than himself and structures compensation with significant equity that vests over five years to ensure long-term commitment. This approach creates what he calls a "superorganism" where the collective intelligence far exceeds individual capabilities.

Apply the Same Proven Toolkit Across Industries

Brad has developed a repeatable methodology for building billion-dollar companies that works across different industries. (28:06) He looks for large, growing, fragmented industries where technology can create advantages and AI won't disrupt in the near future. Once he identifies the right industry, he assembles an exceptional team, aligns compensation through equity partnerships, and applies systematic improvements to acquired companies - typically doubling their profits within 3-5 years through better pricing, technology, and operational efficiency.

Build Intense Feedback Loops Throughout Your Organization

Brad emphasizes creating "voluminous feedback loops" between all constituents - employees, customers, vendors, and investors. (67:08) He regularly conducts employee surveys asking what single idea would improve the company and reads customer feedback personally. His monthly operating reviews involve 25 senior leaders for 10 hours with minimal breaks, using crowd-sourced agendas based on what the team collectively believes are the most important issues to address. This constant flow of unfiltered information prevents echo chambers and ensures rapid identification and resolution of problems.

Statistics & Facts

  1. Brad Jacobs has built eight separate billion-dollar companies over his four-decade career, with his teams completing over 500 acquisitions while evaluating thousands of potential targets. (106:43)
  2. When running XPO Logistics, Brad managed approximately 150,000 employees worldwide, representing about 1.2 million hours of work per day that needed to be optimally managed and motivated. (102:00)
  3. In Brad's monthly operating reviews, he limits attendance to exactly 25 senior people in 10-hour sessions with minimal breaks, having experimented with larger groups of 40-50 people and finding them ineffective. (56:20)

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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