Chasing More

Happy Thanksgiving to all my American friends🍁. Since US markets are closed I am not sharing the usual weekly market recap.

Instead as the year winds down, I wanted to share something a thought with you - that ties back to one of the biggest motivations for learning about investing:

→ Financial security, independence, providing the best for your loved ones, and of course, fulfilling material dreams along the way😉

Now, imagine this: you’ve made it. You’ve got the $$$ in the bank. Financial goals met ✅ 

Would you risk that for another shot at business success?

The answer I imagine is going to vary from person to person.

But recently, I met someone who did just that. Their story taught me an eye-opening lesson—one that’s especially relevant for anyone building wealth or navigating the complexities of generational change with their parents.

life, after happily ever after

A couple of weeks ago I found myself following this Twitter/X wisdom during a get together with some people.

I spotted the older gentlemen sitting alone across the room. We'd met briefly before, which was lucky for me, since I'm not the type to approach strangers cold.

And quickly we were talking about his various business ventures and investments. You know those people that love to share their entire life story without much pushing haha.

It turns out this gentleman when he was younger inherited a family business along with his brother.

I won’t get into specifics. But it was one of those seemingly boring businesses that private equity firms love to buy these days.

This was back in the 1990s. And the brothers made a smart move.

They didn’t just sit on it.

They expanded, brought in top talent, and spent years preparing the business for acquisition, eventually selling it to a large multinational.

And that was it. Happily ever after….

For a while at least.

Over the next 10 to 15 years, this man enjoyed life.

From what I can piece together: he bought the dream home, a vacation home and a boat.

And spent real, meaningful time with his kids as they grew up.

But then at some point after all that he began feeling the need to do more. Probably around the time his children started leaving for college from the timing of his story.

He became restless.

The thought of being "done" – at the peak of his game – didn't sit right with him. It's a feeling that can hit anyone, whether you're 30 or 60, newly successful or long-established.

And that’s when things got interesting.

two big investments, little experience

Over the next couple of years, he made two big investments:

• Investment A: He and four friends started a small oil and gas company in a Latin American country—without him having any previous experience in the sector.

• Investment B: He opened a restaurant—again, with no experience in the food industry. (Unless you count being a picky eater at Michelin-starred restaurants.)

As someone who spent years in oil & gas, I was fascinated.

But as he went further into his story and adventures it quickly turned rather sobering.

Turns out, his company is in a tough spot right now. A recent accident at their production site caused them to halt operations, and they’ve been chewing through fixed costs with no production for months.

They’ve maxed out on the debt they can take.

And none of the partners, including himself, want to put more money into the business. So, they are looking to raise equity, just to get operations restarted and settle short term obligations.

After fifteen years and $20 million invested, these guys have barely taken out any profits!

And then he said something that really hit me:

“I believe in this business long-term, but I am 69 years old now. When am I going to see the benefits of the investment and actually be able to enjoy them?”

Ouch.

As for the restaurant, he was less interested in discussing that with me.

What he did say, however:

“I got myself into this food business alone, and I am going to get out of it myself alone too.”

Didn’t sound that promising either.

From his story and knowing the restaurant I am sure he’s sunk a couple of million dollars into that business too.

And I suspect he has not gotten much return out of it either.

I could sense a lot of regret as he spoke.

Although he does not seem like a cocky or arrogant guy, clearly at some point he thought these big, complex investments would pay off - above and beyond what a regular joe portfolio would have given him.

Later that night back at home, my wife and I stat there thinking about his situation:

Here was a man who, fifteen years ago, had at least $10 million in liquid assets. Not counting his properties, the boat, or anything else.

And he’d likely sunk at least half of that into these two businesses.

Those $5 million in a regular investment portfolio, earning an 8% return over fifteen years would be worth between $15 and $20 million today. Safe. Secure.

Instead, he's probably lost a significant chunk. Worse, he might need to keep pouring money in just to salvage some value.

My thoughts went beyond the obvious “invest in what you know” advice we’ve all heard before.

The question I asked myself was: What are we chasing in life?

This guy had it all—the wealth, the freedom, the time with family. But once he had crossed that finish line, he still felt the need to keep running, to chase after something more.

And in the process, he had risked a good amount of everything he had worked so hard to achieve.

And maybe deprived his family of receiving the kind of security and legacy that he had received from his parents.

Why???

I don’t have a great answer I guess. We all struggle with understanding our purpose in life. And attempting to live a meaningful experience.

What I do believe is a common mistake is the tendency for people fill empty spaces in their lives, emotional, ego, etc. with money. And the results can be pretty terrible. And that’s what this man’s story reminded me of.

Most of you reading this are pretty young, like myself, and we have many years ahead of us to convince ourselves that we have time to correct the many mistakes that we may have committed. Or achieve objectives that we haven’t yet fulfilled.

And my conversation with this gentlemen left me with his feeling - of the growing realization that time was no longer on his side.

As young investors we are now at an age where we can objectively analyze the actions and outcomes of our parents generation. Some never found success, some built wealth only to lose it, and a rare few managed to grow and preserve their wealth.

And how to be part of that last cohort my friends is what I hope we can keep exploring together week after week. Through the inevitable ups and downs that life and the markets will throw at us.

Takeaways

Define Your Purpose Beyond Work: We all face moments of crisis or restlessness. But trying to prove you've "still got it" can lead you down treacherous paths.

Recognize When You've Won: Sometimes, you only strike gold once. And that's okay - some people never strike shit. Even Bob Dylan admitted this:

Understand The Two Stages of Wealth: As Morgan Housel points out in one of my favorite segments he’s written: "Getting money and keeping money are two different skills."

Embrace Process Over Outcomes: When it comes to investing focus on making sound decisions based on a process, your knowledge and risk tolerance.

Surround Yourself with Wisdom: Have a network of trusted advisors, mentors and friends who can provide perspective when you're tempted to make drastic moves.

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