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  • Writer's pictureCJ DiMaggio

Why investing is like writing a love letter

One of my favorite clients handed me a new project the other day, and it was like nothing I had ever seen before.

There was nothing unusual about the site. It was just seventy of the prettiest acres in Texas Hill Country you could imagine, with meadows of bluebonnets and tall pecan trees lining a lazy river.

But unlike most of my clients, who only want to know how quickly and how profitably they can develop a piece of property, Samuel had a very different motivation.

Samuel is a math and finance whiz. He routinely cuts multi-million dollar deals with investment groups all over the world. He has very high standards for his projects and for his expected returns.

But this time around, he didn’t really care about all that.

He had purchased the land a few months ago, and he loved it. He wanted me to write up a due diligence report not to come up with an entitlement strategy or to subdivide it or to prepare it for sale, but just to document what he thought about the land and how he felt about it.

“If I get hit by a bus tomorrow,” he said, “I want my wife to know what I was thinking about this piece of property, and what her options are.”

In other words, he wanted this report to be part of a love letter to his wife.

They had stumbled upon the property together and fallen in love with it. They imagined someday building a weekend retreat on a bluff overlooking the river. They envisioned their kids swinging from a rope swing tied to the tallest oak. Lazy afternoons fishing, and family reunions in the grassy meadow.

Their investment was a safe bet, in a sense. The land was on the edge of a fast-growing, vibrant metropolis, and there would always be a buyer for a piece of property like this.

But since nothing is ever certain in life, and since none of our dreams is ever guaranteed, Samuel wanted to make it easy for those he might leave behind.

My report would probably never be read or used by anyone but him, but it would be there for his loved ones just the same: twenty pages of boring maps and graphs and prose, bundled with a grant deed, buried in a safe deposit box. But it was a love letter, nonetheless, and in effect it would read:

“Here’s what you need to know. Here’s what you need to do. I wish I were still with you. But lean on my words and let them give you comfort. Because, in truth, I am still with you.”

I have often thought that an investment has to feel right, even if you never deploy capital without first calculating IRR and ROI. Sure, people want to profit from their investments. But first and foremost, you have to feel like you’re doing the right thing and for the right reasons. You don’t wade into the details and the pro formas until you have checked that box.

That’s what Samuel was doing: the right thing, for the right reasons.

There was a time and a place for making money.

But there was also a time and a place for doing the right thing, regardless of money.

Are you looking for opportunity in the right place?

Book a consultation with us at to make sure you’re making the most of your real estate opportunities.

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