There is No Magic Pill

October 28, 2023

If there is one thing I’ve learned over the years, it’s that when it comes to money, people crave answers.

They desperately want someone to come along and give them the hidden key that will unlock a treasure trove of riches and set them on the path to financial freedom once and for all.

But despite what the gurus might say, the sadly unsatisfying answer is that there is no one-size-fits-all solution.

In my fighter pilot days, we had a running joke that when you asked a Top Gun instructor a question, the answer would always be, “It depends.”

The fact is: investing, wealth building, and personal finance are nuanced. What works for one is often completely inappropriate for someone else – everything is situational and no two journeys are alike.

Because we have a natural tendency to believe others must have it figured out, most people end up chasing the hot new flavor of the month. This fueled-by-FOMO approach results in a never-ending cycle of throwing spaghetti against the wall to see what sticks.

I call this the “Spray and Pray” strategy.

I can’t tell you how many high earners I see whose portfolio resembles a dartboard of micro-investments – $50k here, $100k there – with no method to the madness other than hoping one of them will eventually hit it big.

I know because I used to spray and pray.

And the irony is that it doesn’t need to be that hard. I spent years chasing deals, doing due diligence, dealing with attorneys, negotiating, mentoring, tracking down K-1s… and the list goes on. Exhausting.

So what is the solution?

In this case, all you need is a plan. Nowadays, I know where every dollar is going before it hits my bank account.

I have one, five, and ten year goals for my portfolio. Quarterly, I look at how I’m tracking against those goals and adjust if necessary.

My current goal? Increasing my liquidity until it accounts for 33% of my net worth.

After years of investing millions in real estate and venture deals, and given the fact that my wife and I each own fairly illiquid businesses, my portfolio was seriously imbalanced.

So that’s it.

Every time we have excess capital, it goes toward rebalancing for more liquidity.

Boring. Systematized. Easy.

And here’s the best part. I don’t spend a single solitary second on the siren song of random investment opportunities. When the inevitable email from my friend with the next deal of a lifetime hits my inbox, it’s an auto-no.

Like Steve Jobs’ famous black turtleneck, I’ve eliminated an entire category of decisions from my life and reclaimed countless hours – not to mention the associated stress.

And that’s where the true wealth is created – I reinvest that time into the things that matter to me: my family, my relationship, my health, and the various adrenaline-fueled activities that bring me joy.

After all, what’s the point of wealth if not to give us the freedom to spend our time on the things that we value?

Sometimes, it really is that simple.

Boring and balanced,


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