Fireside Chat Notes from a 9-Figure Leader

Nov 4

Yesterday I was blessed to get to attend a fireside chat with an investor and multi-business owner with a net worth of hundreds of millions of dollars. I want to share some of the simple, yet powerful, pieces of wisdom he imparted during the conversation.

On Key Attributes of a Successful Leader

This wealthy individual attributed his success overall to two things:

(1) He was never really the best at anything, but was willing to outwork people to reach the finish line.

(2) He realized early on that he had to make a choice between controlling everything in his businesses or growing BIG.

Ultimately, he decided that he wanted to “go big,” which meant he had to learn how to delegate effectively in his businesses pretty quickly, and he benefitted extremely well from that effort. His new passion pursuit became finding the best people he possibly could to run his businesses better than he could himself. This admission of “never being the best” kept him humble and helped him delegate, raising up talented leaders in his organizations and enabling him to exit the daily operations roles in favor of pursuing his search for even more talent to continue to grow his businesses.

On Following the Cues of Successful People

He has always sought to connect with and learn from people who were ahead of him and more successful in business. He would even pay for the opportunity to get some time with successful people so he could personally learn their models. He shared that he actually spent $50,000 to sit down, for a very short amount of time, with Richard Branson, to learn some of his models for building wealth. He walked away from the conversation with a few models he considered to be foundational for growth in the next chapter of his life. He made it a point to share with us that he considers the pursuit, documentation and implementation of models as a cornerstone of his exponential growth over his professional career.

On Connecting with Others

He's always been adept at connecting with people. He attributes his ability to connect with people to these characteristics: humility, confidence, and persistence. He told multiple stories where people would ignore him at first or flat out tell him “No,” but he continued to persist, reaching out to them in different ways and guaranteeing he wasn’t going to waste their time. They would eventually succumb to connecting with him. He would do his best to bring value to every conversation, while also never failing to gain value from it himself.

He also ended each conversation by asking the other party about their preferred charity organization. Somewhere along the way, he learned that the most successful people are usually those most willing to get behind a cause and contribute financially to it. So, he would seek to figure out what that was before parting ways. After the meeting, he would contribute something to that charity – whether it was $100 or $500+. Then, he would diligently follow up the conversation with a thank you note and share that he contributed some amount of money to their charity of choice in gratitude for their time with him.

On the Importance of Documentation

This individual emphasized the powerful role of documentation in his career trajectory many times throughout this fireside chat. While he documents everything he learns from his meetings and connections, he also shared his very simple formula for his accountability meetings with the leaders of his businesses. In each meeting, he just keeps asking them, “What are you going to do next?...What will you get done this next week/month?” He then writes down the three or four things from their response. In their subsequent meeting together, he ensures that the same paper with those three or four items jotted on it is visibly in front of him when he asks them, “Well, did you get these done?” He figured out that if he just physically kept track of what they said they were going to do in each meeting, the chances of them actually completing those tasks increased exponentially. This documentation made him better at holding his leaders accountable, and it certainly made his leaders more productive. He’s got years of these conversations with his people documented. And he follows the same accountability formula for himself.

On Reflections of a Wealth-Building Journey

Recall that this individual’s wealth amounts to hundreds of millions of dollars. A fellow attendee asked him, “Would you have stopped sooner on your wealth journey if you could go back and do it again?” He replied with a resounding, “YES.” He described how, as he has gotten wealthier, the complexity of his lifestyle has increased and his freedom has dwindled. That has been a bit of a burden for him to bear. In hindsight, he would have stopped earlier – somewhere closer to a net worth of $20Million, a number he feels would have been plenty of money to fund his life, while keeping his life a good bit simpler.

I think this is so interesting to keep in mind: a person with hundreds of millions of dollars thinks that his life would have been simpler and better if he would have stopped at $20M net wealth. The inherent lesson this calls to my mind is that things complicate life. Simply put, our lives are full if we do two things: love our God, and love all the people of the world. Those are the things that give us a fulfilling life. All of the personal goals, the things we want to have, the achievements we desire and pursue are a burden we put on ourselves. There is no Higher Power expectation that we go out to work a job for twelve hours a day to growth our wealth – that is entirely self-inflicted. Remember to keep your priority straight. Life is simpler and easier to bear if we keep this lesson front of mind.

I hope these notes help you in some way. Success leaves clues, and it is always great to learn from those more successful than us.