Skip to main content

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: 

  1. The belief that you’re right, no matter what.
  2. The belief that other people must hold the same opinions as you do.
  3. 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:

  1. Turn off all devices.
  2. Only one person talks at a time. No side conversations.
  3. Give the speaker your full attention and keep an open, receptive mind.
  4. 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.

Comments

Popular posts from this blog

Effective Listening: Do's And Don'ts

Here are some great tips from Michelle Tillis Lederman's book, The 11 Laws of Likability .  They are all about: what to do and what not to do to be a leader who's an effective listener : Do : Maintain eye contact Limit your talking Focus on the speaker Ask questions Manage your emotions Listen with your eyes and ears Listen for ideas and opportunities Remain open to the conversation Confirm understanding, paraphrase Give nonverbal messages that you are listening (nod, smile) Ignore distractions Don't : Interrupt Show signs of impatience Judge or argue mentally Multitask during a conversation Project your ideas Think about what to say next Have expectations or preconceived ideas Become defensive or assume you are being attacked Use condescending, aggressive, or closed body language Listen with biases or closed to new ideas Jump to conclusions or finish someone's sentences

Seven Tough Questions To Ask Your Team

  High-functioning teams can disagree and still produce excellent products and results. Team members can also disagree and still care about each other. And, they can challenge each other to think differently. Best-selling leadership book authors  Scott J. Allen  and  Mitchell Kusy  recommend that leaders ask seven tough questions of their teams to help maximize their results. Here are those questions to ask each team member: What are some obstacles  affecting this team? What are opportunities  we could take advantage of that we have been largely ignoring? Where can you take greater ownership  on this team? Where have you let this team down ? Compared to other teams with which you are familiar,  how are we doing ? When was the last time you complimented the team  or one of its members? How open are you to giving direct feedback  to team members?

70 New Year's Resolutions For Leaders

With 2025 fast approaching, it's a good time to identify your New Year's Resolutions for next year. To get you started, how about selecting one or more of the following 70 New Year's resolutions for leaders? Perhaps write down five to ten and then between now and January 1, think about which couple you want to work on during 2025. Don't micromanage Don't be a bottleneck Focus on outcomes, not minutiae Build trust with your colleagues before a crisis comes Assess your company's strengths and weaknesses at all times Conduct annual risk reviews Be courageous, quick and fair Talk more about values more than rules Reward how a performance is achieved and not only the performance Constantly challenge your team to do better Celebrate your employees' successes, not your own Err on the side of taking action Communicate clearly and often Be visible Eliminate the cause of a mistake View every problem as an opportunity to grow Summarize group consensus after each decisi...

How To Build Great Work Relationships

Here is a new book I wish was published back when I was early in my career. It’s called,  Bosses, Coworkers, and Building Great Work Relationships . It’s one of four books in the new  Harvard Business Review  ( HBR )  Work Smart Series .  The book includes adapted content from 20 articles that previously appeared on HBR.org.  “We probably spend more hours with our coworkers than with anyone else. So even if they’re not all perfect, it’s worth it to build connections that will provide you with support, help you network and learn, and keep your career moving forward,” shares HBR.  “This book helps readers make so-so work relationships better, keep the bad ones from bringing them down, and help them build lasting connections with incredible people.”  HBR adds that the book includes chapter takeaways and dozens of resources so that you can go beyond the book to engage in the media (video, audio, etc.) you learn from best.  As you read Bosses,...

How To Use Failure To Succeed

“On the path to success, we trip and lose our footing from time to time. But stumbling and even falling is the best way to learn from mistakes and is critical to achieving goals,” says  Bill Wooditch , author of the book,  Fail More: Embrace, Learn, And, Adapt to Failure As A Way To Success . “We all fail. It’s a part of business, and it’s a part of life,” explains Wooditch. “It’s how you deal with setbacks is what makes the difference.” The book will teach you how to: Conquer the negative emotions that naturally arise after making mistakes. Clearly articulate lessons learned. Put these lessons to use immediately.  Plus, you’ll learn how to: Navigate all forms of rejection and failure in pragmatic ways. Rationally examine your personal fears and gain mastery over them. Shed the discomfort of uncertainty, which is the only way to open your mind to all possibilities.  Wooditch answers these questions for us about failing, succeeding and his book: Question :  We ar...

How To Be A Learn-It-All Leader

“Great leaders are great students, and the world is their classroom,” says   Damon Lembi , author of the new book   The Learn-It-all Leader .  “Learn-It-All leaders are constantly creating and re-creating themselves, their companies, and their leadership. They are information extractors. They pull what they learn about everything—be it product innovation or how to inspire a team—from their lived experience,” adds Lembi.  These types of leaders also model and directly encourage a culture of learning inside their organizations. This attracts higher-quality workers, improves their performance over time and holds onto them longer.  The book is divided into two parts: Part 1:  Being  –  explores how Learn-It-All leaders think . Part 2:  Doing  –  examines what Learn-It-All leaders do differently .  Damon Lembi Some of my favorite takeaways (including some quotes) from the book include:  Quote : “Live as if you were to die tomor...

How To Be A Collaborative Leader

Edward M. Marshall 's book,  Transforming The Way We Work -- The Power Of The Collaborative Workplace , remains relevant today, two decades after Marshall wrote it. Particularly useful is the book's section that teaches readers  how to be a collaborative leader . Marshall says that there are  seven different, important roles and responsibilities of collaborative leaders when leading teams , and those leaders should select the appropriate style to meet the team's needs. The seven roles are : The leader as sponsor  -- You provide strategic direction, boundaries and coaching for the team. You also monitor progress and ensure integrity in the team's operating processes. The leader as facilitator  -- You ensure that meetings, team dynamics, and interpersonal relationships function effectively. You also ensure internal coordination of activities among team members. The leader as coach  -- You provide support and guidance and you serve as a sounding board. The lea...

How To Fix The 12 Most Common Presentation Mistakes

Here is a must-read book for anyone who makes presentations at work, a club, a non-profit, or to any group of individuals the presenter wants to persuade to take action.   The book is,  Presentation Ready , by  Terri L. Sjodin , one of America’s leading experts on persuasive presentations. Her specialty is blending communications theory, field research, and practical sales experience to help professionals and non-professionals become more polished and persuasive presenters.   When you read the book, you’ll discover the  12 common sales presentations mistakes  and you’ll learn why the mistakes happen, why the mistakes are damaging, and how to avoid the mistakes.  Presentation Ready  is divided into three sections:   Building your case  – the foundation of your persuasive arguments and content. Leveraging creativity  – How your persuasive message resonates with listeners (storytelling, visual aids, structure, curiosity) Honing your de...

6 Ways To Seek Feedback To Improve Your Performance In The Workplace

Getting feedback is an important way to improve performance at work. But sometimes, it can be hard to seek out, and even harder to hear.  “Feedback is all around you. Your job is to find it, both through asking directly and observing it,” says David L. Van Rooy, author of the new book,  Trajectory: 7 Career Strategies to Take You From Where You Are to Where You Want to Be . As today's guest post, Van Rooy offers these  six tips for how to get the feedback you need to improve performance at work . Guest Post By David L. Van Rooy 1.       Don’t forget to as k :  One of the biggest mistakes people make is assuming things are going perfectly (until they make a catastrophic mistake). By not asking, you’re missing out on opportunities for deep feedback: the difficult, critical feedback that gives you constructive ways to improve. 2.       Make sure you listen :  Remember, getting fee...

10 Quotes From The 5 Levels Of Leadership -- John C. Maxwell

Soon I'll post my full review of John C. Maxwell's latest book, The 5 Levels of Leadership .  In the meantime, here are some of my favorites quotes from the book that I believe should become a must-read book by any workplace/organizational leader: Good leadership isn't about advancing yourself.  It's about advancing your team. Leaders become great, not because of their power, but because of their ability to empower others. Leadership is action, not position. When people feel liked, cared for, included, valued, and trusted, they begin to work together with their leader and each other. If you have integrity with people, you develop trust.  The more trust you develop, the stronger the relationship becomes.  In times of difficulty, relationships are a shelter.  In times of opportunity, they are a launching pad. Good leaders must embrace both care and candor. People buy into the leader, then the vision. Bringing out the best in a person is often a catal...