Ep 62: I spent the weekend with multi-millionaires

As I drove from Chapel Hill, North Carolina back to Athens, Georgia I had the chance to reflect on an unforgettable weekend. My friend hosted a gathering of entrepreneurs, a house full of influential, successful, thoughtful, badass people. Some of them are billionaires that have sold businesses for millions of dollars and still operate massive businesses as well. We spent time together playing basketball, getting to know one another, talking about life, business, and what it’s like to build wealth.

One uniquely common thing is that most people there worked extremely hard on something special and different for a long time. There were very few overnight successes, most sacrificed 60-70 hours a week for years. This actually made me a bit self-conscious and embarrassed feeling that I hadn’t worked as much as the others in the room and therefore hadn’t earned my spot there. But it was insightful to hear people talk about how hard they had to work to get to where they were.

There also wasn’t much alcohol consumed. Of the 25 people in attendance, over 10 of them didn’t drink at all. This was a positive change of pace for me that I found quite refreshing compared to a lot of my friends who still look forward to social drinking and partying.

The most shocking realization was just how human everybody at the gathering was. For one, there was a uniform emptiness associated with the act of reaching enough cash to be comfortable. We all got hooked on the thrill of generating business and landing deals, getting addicted to the game of starting a company and learning to execute. It can be really challenging to pull away from, but we all have our teeth sunk in.

A lot of folks were really vulnerable and insecure too. Their insecurity has driven them to work their butts off, get good at something, and find success. But we all deal with a fear of failure, inadequacy, and emotionally taxing times. Very few wealthy people talk about how they don’t feel adequate and how awful it feels to make a critical bad decision that costs you years or millions of dollars, but we all shared those feelings.

I’m coming back from this weekend with a greater focus on being balanced and present in all areas of my life. Staying fit, being a good father and husband, maintaining hobbies and having a good social life has always been important for me, but this can be a struggle for many entrepreneurs because we’re not wired for balance. I worry that I’m not being a great father right now, as I’ve come to really understand the difficulty of parenthood. I need to come to terms with my Twitter and email and deal addiction. A few folks from the weekend talked about how much seeing a therapist has helped them, and I’m looking into that as well. I want to keep working on my business, but I’m also looking forward to drinking less and focusing more on my family and hobbies.

You may think of wealthy millionaires and billionaires as having everything together, but really we’re all goofy dorks and nobody is overly special. These people are brilliant and great at what they do, but they’re still people; they’re still struggling, and money doesn’t solve all of these problems. This weekend left me energized to find things that give me energy and find people that make me the best version of myself, that can challenge me and ask me the hard questions.

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I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.