Build a Board

One of the most valuable lessons I learned while serving time in prison came from studying how successful leaders build strong advisory boards.

In the corporate world, CEOs don’t make decisions alone. They surround themselves with experienced advisors—people who provide insight, challenge assumptions, and help them navigate uncertainty. A well-structured board of directors can mean the difference between building an empire or watching a company collapse.

For example, while I was confined in Fort Dix, I remember reading about Steve Case, the visionary behind America Online (AOL). It was one of the first companies I invested in, and I wanted to know as much as I could about its leadership. When Steve Case was building the company, he put a group of advisors together and they would help him guide strategy, secure partnerships, and navigate the rapid changes in technology. Early board members of AOL included:

• Jim Kimsey, a military veteran with leadership experience, who was a cofounder of AOL and its first chairman.
• Miles Gilburne, a lawyer who specialized in technology deals, offering AOL legal guidance during complex negotiations.
• Robert Pittman, a media executive who later played a pivotal role in transforming AOL into a media powerhouse.

Later, he expanded his board to include people who would help him understand his customers better, and he also invited influential people who had specific expertise that would help AOL grow. Each board member brought a unique skill set, from legal expertise to operational leadership to media experience. That strategy helped AOL become one of the most dominant internet companies of the 1990s, ultimately leading to its historic $164 billion merger with Time Warner in 2000.

I’ve never run a company, but while in prison, I had to run my life and prepare for the future. Since the decades I had to serve separated me from the job market, I wanted to find guides who would help me make better decisions and prepare for the challenges ahead.

Instead of waiting until after my release to seek advice, I built my own board of directors while incarcerated. I identified people who could help me prepare for success at different stages of my journey:

• In the early years: I sought guidance from professors who helped me develop my education. Even though I couldn’t visit a university, mentors like Bruce McPherson and George Cole brought the university to me. They visited me, corresponded with me, and provided intellectual challenges that helped me grow.
• In my final decade: I shifted my focus toward business leaders. I wanted to learn how they built companies, overcame obstacles, and developed strategies for long-term success.

I studied their experiences through books, wrote letters, and connected with people who could help me understand how to build a meaningful career after release.

A strong board of directors—whether for a company or personal development—does three key things:

1. Provides Perspective – A good board challenges flawed assumptions and offers new ways of thinking.
2. Holds Us Accountable – The best advisors ensure we stay focused on long-term goals, not short-term distractions.
3. Expands Opportunities – A well-connected board can open new doors, introduce key relationships, and provide insights we wouldn’t have on our own.

I completed my obligation to the Bureau of Prisons on August 12, 2013. While I’ve never run a publicly traded company, the lessons I learned in prison still guide me today. Now, I have a personal board of directors to help me navigate business and nonprofit work. I rely on three key advisors for guidance in my nonprofit endeavors:

• Bill McGlashan – A seasoned impact investor who understands how to build organizations that create social good.
• Agustin Hunneus – An experienced operator who brings business expertise to decision-making.
• Peter Hardin – A former Assistant U.S. Attorney, who helps me navigate legal complexities in the nonprofit sector.

These individuals help me make better decisions, anticipate challenges, and think long-term.

This strategy of finding qualified advisors can help anyone who wants to grow. If you want to succeed in any area of life, ask yourself:

• Who can provide guidance and offer insight into how to create accountability metrics?
• What qualifications should your advisors have?
• How can you attract and retain people who will help you reach your highest potential?

The strongest leaders find people to challenge their ideas, and that exercise helps people reach a higher potential.

Self-Directed Learning Question:

• Who would you choose for your personal board of directors, and how will you ensure that you are worthy of their mentorship and guidance?

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