It's All the Dumbass Things I Did That Taught Me the Most

I’ve spent most of this year in Palm Beach, where it is not unusual to meet new people and hear them boast of their accomplishments, riches and social contacts. I don’t mind so much. Many of them are very nice people, and it’s just part of the local culture. Besides, I find people’s life experiences interesting and always enjoy meeting new people.

However, I think it is much more entertaining to talk about all the dumbass things we have done, and I have a whole sack full, all of which cannot possibly be listed in this 1,227-word article.

Where to even start?

When I was in my late 20s, I was right much of a gunslinger. There was a huge 1,300-acre piece of property on the south side of the James River, right smack in the way of future development. People had been trying to buy it for years.

I called the corporate office just minutes after they had decided to sell it. I grabbed my buddy, who had a single-engine airplane, wrote the contract while we were on board, and within about an hour, I had the property under contract in my name.

By the time I got back to Richmond, word had gotten out. A fat cat from Washington offered me $1 million, to be delivered that afternoon, if I merely assigned my contract to him.

But you see, I was a cocky little snit who had done spreadsheets.

Yes, SPREADSHEETS!

The spreadsheets told me I was going to make a gazillion dollars developing the property over the next 15 years. And we all know how accurate spreadsheets are!

I turned him down.

That was a DUMBASS thing to do.

Then there was the time my buddy Doug Dorsey and I were approached by some kid with the great idea to rent a kiosk at the mall and make instant websites for shoppers. I’m sure we cranked up SPREADSHEETS that showed us having these kiosks in every mall in the country and eventually buying Bill Gates out of Microsoft.

I can’t remember exactly what happened, but I think the guy took all the money and equipment we had given him, bought a VW van and followed the Grateful Dead around for several years.

Giving that guy money was a DUMBASS thing to do.

I once refinanced a shopping center I owned just so my banker could meet his loan quota and earn a few atta boys from his Too Big to Fail Big Bank employer.

I got absolutely nothing out of it. The closing costs were ginormous. The bank got all the fees. I could’ve just called the bank president and told him what a good guy my loan officer was.

Refinancing that shopping center was a DUMBASS thing to do.

My friend Sammy is a handyman. I had him over at my house for months and months making renovations. Sammy had a big truck, and one day we needed a small load of lumber. He was about to run out to Lowe’s to fetch it.

I said, I’LL GET IT!

I was paying Sammy $45 an hour and didn’t want to take him off the job site. There was only one problem: I didn’t have a truck.

So I loaded a bunch of 10- to 12-foot 2x4s into my Mercedes S-500, extending from the back seat through the sunroof about eight feet into the air.

A few days later, I had to replace the struts, shocks, sway bars, tie rods and God knows what else because I had pretty much destroyed the undercarriage of my Mercedes.

I did all that to save $45.

Boy, that was a DUMBASS thing to do.

As oxymoronic as it may sound, sometimes DUMBASSERY is actually the result of being too smart. Better terminology might be getting "too cute."

Back when I was a young buck, I was really good at using my creative abilities to put deals together. It allowed me to buy assets on extraordinarily good terms. The problem was that once one closes on a good deal, a reasonably prudent person would then turn his attention to managing that asset.

I was not a reasonably prudent person.

I had an unhealthy addiction.

I was a DEAL ADDICT!

I’d always turn my attention to the next deal instead of being a good steward of the deal I had just bought.

I once used my country-boy charm to get a lady who never wanted to sell her property to finally sell it to me. I got it zoned for 185 townhouses and had the engineering and architectural plans drawn up. I was ready to close.

But I had gotten too cute.

My purchase documents gave me the right to pay for the property with a note that was subordinated to a construction loan, with the seller being paid out of cash flow rather than through a release price for each unit sold. I called this a “cash flow note.”

I was quite proud of my cleverness.

I was too clever.

Despite being bound by a contract that her lawyer had helped draft—and yes, I had used my aw-shucks country-boy charm on him too—a family member got to her, and she refused to convey the deed.

Litigation ensued. Everything became a mess.

I got too cute.

That was a DUMBASS thing to do.

Before writing this article, I contacted a couple of guys who used to run companies of mine and suggested they give me some ideas for DUMBASS things I’ve done.

They both said it would take too long to list them all.

Needless to say, my dumbassery has not been confined to business. I’ve done plenty of DUMBASS things involving cars, alcohol, girls, parenting, having a smart mouth and numerous other subjects that are probably best left for another article.

The 2008 financial crisis was an ugly time for me.

I remember strolling up to the zinc bar at my local French bistro almost every night after working until 10 p.m. There were a number of other guys there just like me.

We hated the banks. We hated the Fed. We hated the politicians.

But we also knew something else.

We were partly to blame for the predicament we were in.

We were all deal addicts.

And for perhaps the first time, a bunch of guys who had spent years talking about their successes were talking about their mistakes. Guys who had been somewhat supercilious and arrogant when they were on top of the world were suddenly vulnerable and approachable. We laughed at ourselves for being wired the way we were wired.

Discussing our dumbassery was therapeutic. And frankly, we had a hell of a lot of laughs.

So I’ll offer a little advice to those who feel the need to stand 10 feet tall and bulletproof, whether buying, selling or just trying to impress the guy sitting next to you at the bar. I really don’t care to hear how great you are or about all the important people you know, etc. If I’m doing business with you, I want to hear what a DUMBASS you are.

The way we learn is by being a DUMBASS. Admitting and laughing about dumbassery is a great way to gauge one’s honesty and competency. Besides, laughing at our foibles is downright fun.