My son, Braxton, was “forced” into homeschooling this spring. At first, it was a daunting task for all of us. He had to get used to creating some structure, while my wife Amy and I had to become fifth-grade teachers overnight. After a few weeks, we created a system, and it was a breeze. Of course, Braxton did his math, reading, Latin, science and core classes. That was the mundane required work. And in addition to schoolwork, he learned about payables, cash flow, receivables and inventory management. He even (unfortunately) got to see dad lose a deal and get mad. All part of life. From “Zoom-bombing” me on CEO peer calls to listening in on conference calls, he became more and more curious as to how my peers found their individual success. He asked me if he could interview successful people, ask them questions, write down their answers and repeat the process. This spring, I taught Braxton geometry, and Braxton taught me lessons about life.

Each successful person we asked was happy to allow Braxton to interview them. All were honored to oblige and made time for him; more time than we expected. He wrote down his questions on a legal pad prior to meeting with each person. I offered to be his scribe and he declined. They seemed to appreciate his preparedness and lack of small talk. The enjoyment displayed by the interviewees was clearly visible as an 11-year-old asked them questions about their personal stories. Here are some common themes to questions this wise kid drummed up:

Getting Started. Each person lit up as they described how hard they worked to get started. They shared their successes early on as well as their failures. “Grit” was a common word used to describe the early days. “When you fall, get back up.” “Never give up on your dreams.” “Success comes after many failed attempts.” “Keep going.” On too many occasions we only see the success side of people. The back story and courage to get to where they now are is amazing to hear about. 

Tell me about your second deal. The common theme here was how much smoother the second deal went than the first deal. Each person shared lessons learned the first time and how they were more efficient the second time around.

What do you enjoy about your work? Believe it or not, money never came up. Answers ranged from helping others succeed to being around people. Most would think successful people only care about money. Quite the opposite was true as a theme of selflessness clearly was witnessed.

What do you dislike about your work? Stress, criticism and challenging issues were talked about most.

What mistakes could I avoid? Allowing expenses to get out of control, investing where everyone else is investing (like lemmings), and not paying attention in church.

Do you invest in the stock market? I’ll sum all the answers up in one word: NO! Most of the those interviewed have built their wealth in some form of real estate that they could (for the most part) control.

Who else should I talk to? Of all the questions, this one has the most wisdom. People genuinely want to help people succeed. Each interviewee was eager to name people they know who they thought would love to sit down and share their wisdom. The following superstars were interviewed by Braxton: an apartment developer, one of the largest homebuilders in the USA, a private equity investor and a star quarterback from Clemson University. They all named people even more successful than them that Braxton should talk to. As his dad, I can not wait for this to play out!

As always, feel free to email your comments and suggestions to me at