Leadership Lessons From A Serial Entrepreneur

Brad Jacobs’ book provides you a treasure trove of leadership lessons from a man with more than four decades of CEO and serial entrepreneur experience. So, even if you don’t envision yourself wanting to earn a billion dollars, don’t pass up reading Jacob’s, How To Make A Few Billion Dollars.

In the book, Jacobs defines the mindset that drives his remarkable success in corporate America – and distills a lifetime of business brilliance into a tactical road map. And he shares his techniques for:

Turning a healthy fear of failure to your advantage.
Building an outrageously talented team.
Catalyzing electric meetings.
Transforming a company into a superorganism that beats the competition.

“This book is about what I’ve learned from my blunders, and how you can replicate our successes,” says Jacobs. He shares his candid account of the highs and lows of entrepreneurship.

Jacobs has founded seven billion-dollar or multibillion-dollar businesses, completed approximately 500 M&A transactions, and raised 30 billion dollars of debt and equity capital, including three IPOs. He began his career at age 23 when he founded Amerex Oil Associates, followed by Hamilton Resources, both privately held. He subsequently created five publicly traded companies—United Waste Systems, United Rentals, XPO, and XPO’s two spin-offs, GXO Logistics and RXO.

This entrepreneurial titan leads with humility, compassion, and accountability, and recommends all leaders do the same. For example, regarding the importance of staying humble, Jacobs writes, “Coming out on top when your company is under attack feels thrilling in the moment. But nothing—I repeat, nothing—could be worse for your decision-making skills than that feeling of being invincible.”

Brad Jacobs

Some of my favorite leadership lesson takeaways from the book, written in an easy-reading, conversational and friendly style, include:

Successful people are self-aware enough to avoid the following three impediments to effective leadership:

The belief that you’re right, no matter what.
The belief that other people must hold the same opinions as you do.
The belief that every inch of a potential course of action must be analyzed before you act.

Two book chapters in particular stood out to me:

How to Build an Outrageously Talented Team
How to Run Electric Meetings

First, regarding building a talented team, Jacobs explains that you need a team of people who are smart, hardworking, honest, and kindhearted. He recommends you hire for intelligence, hunger, integrity and collegiality.

In addition, he states that it is better to be slightly understaffed, but not badly understaffed. “A team that’s appropriately lean has a more concentrated focus and gets more done,” explains Jacobs.

Next, to run your most effect meetings, Jacobs says you should have everyone follow these four rules:

Turn off all devices.
Only one person talks at a time. No side conversations.
Give the speaker your full attention and keep an open, receptive mind.
Disagree, but disagree respectfully.

Toward the end of the book is Appendix C, which lists 45 core questions to help you assess job applicants. “The questions will give you insights into a candidate’s self-awareness and behavioral traits prior to the interview so you can get to know the real person before you sit down with them,” shares Jacobs.

Finally, as an unexpected special treat, Appendix B provides a fascinating History of Technology Timeline, starting with the first technological milestone dating back to more than two million years ago. And with the latest entry being 2023 – when Google released its generative AI natural language processing tool.

As you review the timeline you can test your memory regarding when the following were invented:

Eyeglasses
Telescope
Telephone
Frozen food
Commercial jet airline
Mobile phone
Wearable continuous glucose monitoring system (as approved by the FDA)

Finally, and perhaps my favorite learning from the book, is Jacobs’ recommendation for an easy way to create an optimistic frame of mind. He suggests asking this question of individuals you encounter each day:

“What was the happiest part of your day?”

That question Jacobs professes has a more uplifting effect on you and the person answering the question than the question, “How was your day?”

Thank you to the book’s publisher for sending me an advance copy of the book.

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