Welcome back to the Real Conversations Newsletter!

My name is Jacob O’Connor and I’ve interviewed 300+ high performers for my podcast, Real Conversations. Every Tuesday I send out 3-4 of my biggest takeaways from that weeks podcast episode. Short, concise, and never spam.

Today’s newsletter post is from this weeks Real Conversation’s episode with Brian Estes- Entrepreneur, Angel Investor, Crypto Expert, & NCAA Wheelchair Basketball National Champion. Know someone who you think might be interested in this newsletter? Forward this email to them (we’d appreciate it 😉).

Brian Estes- Entrepreneur, Angel Investor, Crypto Expert, & NCAA Wheelchair Basketball National Champion

At the age of 16, Brian was paralyzed from the waist down. He went on to become a 3x NCAA wheelchair basketball champion before eventually spending time at the University of Cambridge and the London School of Economics. Brian is now the Founder and CEO of Off the Chain Capital, an alternative investment fund, as well as an angel investor in many notable companies including Coinbase. Here are 3 takeaways from my episode with Brian:

1. You Play with the Cards that You’re Dealt

At 16 years old, Brian was 6’4 and being recruited by some of the top universities for football. A few months later he was paralyzed from the waist down after a car accident.

Reflecting on this, Brian said, ”I focus on the things I can do…not what I can’t…That’s what I’ve always done”.

Understanding the hand he had just been dealt, Brian focused on developing his mind and becoming as sharp as possible. Business would eventually become his new sport, and man, did he ever get good at it…

2. Understand Compound Interest

“Today, we have a lot of assets because of the sacrifices my wife and I made when we were younger"

Brian talks about being 22 years old and not going out on the weekends— instead he was working, trying to save money and build his future because he knew the power of compound interest. You might ask yourself, how does someone end up managing $350M for endowments and universities out of a small office on Main Street in Columbia, Illinois (small town with a population of ~10,000)? Just look at the trajectory he was on when he was in his early 20s…

If you can understand that both money and habits compound, then you can make compounding work in your favor. If you don’t understand compounding, then it will work against you. Either way, compounding is occurring.

3. There’s Always a Way

After Brian sold his practice, he wanted to start investing in private startups focused on Bitcoin and Blockchain technologies— but he didn’t know how he was actually going to do this.

Investing in private companies isn’t easy— it’s not like the stock market where you can go to Robinhood, type in the name of a company, and invest $100. You need to know the right people.

Brian finally found a company he wanted to invest in, Coinbase, but didn’t know anyone there. So he emailed the Founder, Brian Armstrong, who rejected his offer to buy shares. He didn’t give up though.

Brian started emailing employees at Coinbase who had shares until eventually one of them sold him some of their shares. He eventually bought more shares and even become a paid Advisor for the company.

Brian has replicated this strategy over and over, and has gone on to invest in many successful startups and build an impressive portfolio.

You can watch / listen to the episode here. 

You can follow Brian on X here. 

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-Do Hard Things & Live a Meaningful Life-