How To Be Good At Being Wealthy

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When I was in my early twenties, I spent a good percentage of my winter nights at the Crimson Grill in Harvard Square. There was only one thing special about that bar; the beer was OK, the food mediocre, the prices right in line with everything else in town. But they’d play all of my alma mater’s basketball games, and as I was living in a town where I hadn’t gone to college and didn’t know that many people, hanging out with other alumni became important to me.

So every few days between November and March, I would get to the bar about ten minutes before game time, score a seat, order a pitcher and some fried food, and watch sports with people who eventually became, if not friends, friendly acquaintances. I did this for two years, with nothing much interesting to report. We won some games, lost some games, drank some beer.

Then one day in early 2000 Kevin showed up. He was seven or eight years older than me, and I knew him both through college and high school – he had attended the same as I for both. He had founded a company called Student Advantage back in the mid-’90s, a kind of proto – dot com firm that made student ID cards that gave the holder a discount at various businesses. To know what businesses gave the discount, you would either see a sticker on the door or – wonder of wonders – you could check a website and see what was in your town. In these days of location-aware smartphones and instant discounts, that’s not that big a deal, but back in the ’90s, it was a revelation. I’d heard through the grapevine that he’d sold his company to another firm that year, and had done quite well.

When he walked up to us, he was dressed in business casual clothes, tall, slender, with a big smile and an engaging way about him. He met the usual crowd, didn’t drink any beer, ate a burger, cheered our team, and took off early when it became apparent that we were going to win the day.

After the game, the bar started to clear out – it was perhaps a Tuesday night – and our waitress didn’t come over with the bill as she usually did. My friend Ernest eventually walked up to her and asked for the check. She walked back over to our table with him.

“Guys,’ she said. “Don’t worry about it. Your skinny friend – the guy who was here – he paid for all your stuff.”

Such a small thing, but…we were all one or two years out of college, with intro jobs and grad school classes and loans that were only getting larger. Kevin was ahead of us in life and success and wealth, and…he put his money to work in a small, nice way.

Kevin died a couple of years ago, far too young. But I’ll always remember his lesson to me.

That, I think, is how to be a good rich dude. Writ large and writ small, know that others have less, and if you can help out, do.

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