Lessons from a Billionaire

Sep 6, 2021 | Exit Planning, Strategy

What can you learn from a billionaire?

I recently led a peer group meeting where I met two ultra-wealthy entrepreneurs.

The first was a “Boat Man” – a wealthy retired gentleman who loves his boats.

The second was a “Car Man” – a very active billionaire who really loves his cars.

Day 1: Meet the Boat Man

In the first afternoon of our Leader’s Edge peer group meeting, we met in an unassuming boat barn, filled with 10+ antique wooden boats which the Boat Man restored personally; some with help and some by himself.

He shared with us the origination stories of each boat; where they came from, the rich and famous people who owned them, and the stories on how he was able to acquire them.

It was an amazing peak into a world foreign to me.

Our peer group meeting in the Boat Barn.

Our peer group meeting in the Boat Barn.

lessons from a billionaire: We watched presentations which took place at the Boat Shop bar.

We watched presentations which took place at the Boat Shop bar.

The Boat Man was quite humble. After the day’s peer group meeting, we sat around a pool with drinks in hand and discussed life. Towards the end of the evening, he started opening up about his own origin story.

He told us about the business his family had built, and how it serviced a client company owned by Berkshire Hathaway i.e. the Oracle of Omaha. At some point the client company approached them and said, “We want to buy your business, or we plan to start our own.”

They received the proverbial offer they could not refuse. They sold their business and did very well financially.

However, over ten years had passed and the Boat Man still lamented that a portion of his identity was missing, like a member of the family had passed. He missed who he used to ‘be’ and how it defined himself and his larger family.

It seemed that selling his business was a happy/sad moment.

What can you learn from a billionaire? Find out here: Share on X

Day 2: Meet the Car Man

The next day we held our meeting at the Car Man’s office. His office and conference room were on the grounds of his pristine private 18 hole golf course.

lessons from a billionaire: This conference table redefines “big” money.

This conference table redefines “big” money.

Below his office was a drive-out basement with a 200+ car garage and restoration mechanic shop filled with Chevy’s. Ninety-five per cent of them were Chevy convertibles (Vettes, Impalas, Chevelles, etc.) going from the 70’s all the way back to the beginning of the brand.

His most expensive car was a hard top million-dollar Yenko Camaro. He had four of them.

lessons from a billionaire: The Car Man loves everything Chevy.

The Car Man loves everything Chevy.

Where does your happiness come from?

  • The Car Man runs a multi-generation business with his daughter that is very cash flow positive, and this down-to-earth owner is very happy.
  • The Boat Man has cashed out, has all the free time and money he could ever want, but misses the glory days.

Your Challenge – Plan ahead for your happiness; it won’t be automatic.

There is so much money sloshing around and many businesses are being sold for big dollars.

But once you sell then what do you do?

If you don’t have an “entrance plan” for the kind of life you want and for the kind of person you want to become, then your exit plan may leave you stranded by the side of the road.

Money doesn’t buy happiness; it just buys you free time to be the person you want to become.

So have a plan with a purpose.