I was lucky enough to spend the weekend with some very successful people. My friend Shaan Puri put together a group of 24 entrepreneurs, rented a few big Airbnbs and scheduled a chef and rented a basketball court in Raleigh NC.

There were a few billionaires and famous people. A handful of folks with companies worth over $500 million. Several more with $100 million + exits and a lot more. We played 5 hours of hard basketball in one day and I'm so sore I can barely get out of my chair right now.

I recorded this podcast episode on the experience on my drive home. I spent 5 hours behind the wheel in complete silence. Working to digest what I had learned and figure out the plan moving forward.

A quick note:

I sent this text to my wife after a cigar around a table after midnight when I was trying to wind down for sleep:

A few main takeaways:

1. We were all dorks.

I was expecting a room full of giants. People with the charisma of Barak Obama and the ability to command a room like Jerry Seinfeld. There was some of that - but for the most part these were just normal, average looking / acting people.

They were brilliant, don't get me wrong. They had overcome the odds to build and sell tech companies. They were insanely smart and excellent at storytelling and conversation.

2. We all suffered with insecurity, fear of failure and a general sense of emptiness at times.

Talking with a few guys who enjoyed their success more than 5 years ago and have been worth $20 million + for a longer time, they spoke about business as an unhealthy addiction and how it can leave them searching for more and an empty feeling after an exit.

Others discussed the nagging ego and need for more and bigger. Others discussed a constant fear throughout their career that they weren't worthy or didn't have what it took and just general insecurity.

3. They all had a lot of kids.

It seemed like many of them are very glad they have kids and spend a ton of time and energy in this area.

It is what I learned the most, as you heard in my podcast episode. Most of the folks at this meet up spent a lot of time thinking about and talking about how to raise good kids. The conclusion:

Good kids know how to struggle with grace. Embrace the struggle, don't protect your kids from it.

4. Very few of them started new, groundbreaking businesses.

They started normal businesses doing things that already existed. No new ideas. No revolutionary technology. They saw a need in the market and they got after it and executed better than anyone else. Good old fashioned boring stuff.

5. Expectations that don't align with reality is the cause of all unhappiness.

Almost all unhappiness comes when they expect 1 thing and something else is the reality. Marriage struggles, fatherhood struggles, business struggles. Its easy to get and keep really high expectations when you're a badass in one area of life or another. These folks are badass at making money. So when other areas of life get hard or don't go as well we really struggle with that.

Work on expectations and embrace the struggle.

6. The humility is astounding

Money hasn't turned these folks into prissy or soft jerks. They are still mentally tough and able to struggle through hard stuff. If business is easy they go after other struggles - golf or fitness or whatever.

They're still humble. They ask good questions and try to understand how other people get better. They genuinely care to learn about other people.

They're constantly searching for ways to improve. They are vulnerable and talk openly about their struggles. They're eager to help other people and selfless with sharing their network and giving folks a leg up with no expectation in return.

7. Very few of them drank alcohol - and none drank a lot

15 of the 24 people didn't drink any alcohol on the trip. Not that they don't ever drink, but they didn't need it as a social lubricant. The rest of us had 1-2 drinks per night. This was surprising to me and I'm still thinking about the correlation here - but it definitely inspired me to do less drinking when I socialize with friends.

8. The search for meaning and fulfilling joy continues beyond money

None of your kids or those closest to you will stand up and mention at your funeral how much money you made and that they wish you would have made more.

When you get good at only this, and you accomplish it, you feel empty. Business is fun and exciting as hell. Nothing beats making big amounts of money and doing deals, etc.

But life isn't so sexy all the time. Kids shit their pants. Golf balls go out of bounds. Travel is tiresome. Marriage gets hard and boring.

Finding a deeper meaning is a struggle for many of us. What am I going to do with my life?

"I walk around my house acting like I'm doing something and then end up going out to cut wood." was a stark and vulnerable statement from a successful entrepreneur while sitting around chatting.

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Overall - this was an incredible experience. I can't wait to do more of it and build relationships with people who are trying to live life to the fullest and improve at everything they do while also making those around them better.

Thanks for reading!

Nick

PS. I'm using a new cost segregation firm and it has been a great experience. REcostseg.com (brought to you by Baldridge Financial) is a great, aggressive, low cost option to get your cost segregation studies done. Check them out!