The Anonymous and VERY happy $500 Million Man

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Last week, I met someone with a net worth of $100m+ in cash.

He has 0 social media, and you wouldn’t recognize him on the streets.

He asked to stay anonymous, so for this post, let’s say his name is “John”.

(He did drive up in a $250k sports car but inside the restaurant, he looked just like anyone else.)

That’s the fascinating part about wealth, most of our stories and judgments about it are wrong.

We think rich people wear Rolexes, drive Ferraris, and have flashy gold chains. But that’s really the fake influencers talking.

John worked insanely hard for 15 years to earn 100s of millions at the expense of his family. It was a grind - but now, he prioritizes his family above all else.

But even if you work hard, there’s no guarantee the money will come. So be mindful of sacrificing your family at the expense of wealth. Ideally, if you do make sacrifices, do it before you have a family.

Here are 5 key lessons that stuck with me after our lunch:

1) Flying Private (or not)

My dream is to fly private by the time I’m 50.

When I asked John if he flies private, he said it depends. He’ll fly private if (1) he’s with his kids and grandkids, (2) the time of the commercial flight isn’t great, or (3) there are layovers. 

One time he was taking his kids + grandkids to Aspen, the charter was ~$25k each way. No problem. But on the way back one of his kids and their family decided to fly back commercial. John’s son said he didn’t want his own son (who was 2) to think it was normal to always have these experiences.

That’s an amazing example to show the values John taught his son about respecting money - and how it’s being passed down from generation to generation.

2) Budget your fun

Unless you’re doing a ton of work-related flights, it’s difficult to justify flying private.

“But that’s okay,” John said. “If flying private is what you want to do, then budget it. If you budget it, you will commit and do it.”

Now, where do you get that budgeted money?

John kept repeating a line over and over:

“Spend the yield, keep the principal”

“Spend the yield, keep the principal”

“Spend the yield, keep the principal”

What he meant was this: Budget the output from your investments and allocate it towards fun. 

For example, if you have say $100k, his point is to leave that part alone to grow. But spend the output of it on extravagant things like flying private. ($5,000 can get you a small private plane!!)

Something I found fascinating…

John has a full-time person who helps him manage his wealth. It made me realize what works in business also works in your personal life.

At AppSumo, we have a team to budget, account, model, and forecast our finances. But in my personal finances, I often wing it. Fixing soon.

3) Happiness Inside

My main thought and discussion the entire lunch was about happiness.

I’ve worked with and interviewed many rich people. But I’m not sure if all of them are happy.

Oftentimes, we get trapped in this mindset of thinking it has to be one or the other. Family or wealth. Working hard or being happy. Once I’m rich, I’ll be happy.

But one of my favorite phrases is “You can do both!” They’re not exclusive things. You can work a reasonable amount, make good money, and live the life you want.

Fortunately, there is nothing external required to make you happy. We have all the tools we need to feel good about ourselves. (Yes, money makes it easier at times). But really, it’s about being clear on who we are. Happiness comes from self-awareness and acting in alignment with who we are.

John’s wife wanted him to give away 100% of the money they earned after he sold his company. They didn’t do that but did dedicate themselves to giving away most of it in their lifetime and all of it anonymously.

He truly seems happy, being with his grandchildren, supporting his non-profits, and racing cars.

I do wish I could have met him during the thick of it. He said over the 15 years, the business that eventually sold didn’t work 2 times and the 3rd time it finally worked (Persistence beats resistance).

4) Seek out inspiration 

If you feel uninspired… Go find, meet, and observe others who seem to be inspired.

I asked John to lunch after meeting him last year and it was well worth the $40 salads we ate.

If you don’t have a network, ask your neighbor for someone inspiring they know. Ask someone you see online. Ask your dentist. Ask!

Most people would be surprised how many interesting people are just 1 ask away.

5) Everything changes and nothing changes

So what's different after John had $100m+ in his bank account?

He said everything and nothing. There are more numbers in the bank account which requires more work. But he has the opportunity to be more present with his family than before.

He gets nicer toys and more of them. He has 2 houses. I love that he spends on activities with his family like flying private. But for his wealth, it doesn’t seem excessive. He said he still has to use a toilet, no magical poop vacuum yet… 😂

Overall, the main lesson I took away from John was this:

Money solves money problems. But only YOU can solve your internal problems: like happiness, fulfillment, and meaning.

Rooting for you,

Noah 🌮

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