Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries,” where we ask interesting people to open up about the role money has played in their lives.

I was 9 or 10 years old when I got my first job, delivering the Houston Chronicle. Here was the problem: I was good at delivering newspapers, but I was terrible at collecting money from my customers. When I did my collection rounds, a lot of people would be like, “Hey, can you come back tomorrow?” And I’d say, “Sure, no problem. Sorry to bother you.” But day after day they always had an excuse or they’d pretend not to be home, and as a little kid, my collection efforts had no real teeth.

The way it worked, I’d buy the newspapers in bulk from the publisher as an independent contractor, and once the customers paid me, I’d turn a small profit. But despite all my hard work delivering papers, with my ineffective collection efforts I’d usually have a net loss. I’d hoped to make a little spending money, but I didn’t make money — I lost it. Sometimes in life, the middleman gets squeezed. On the other hand, that paper route sure got me a lot of exercise. I always try to find the silver lining.

The least expensive things can be the most personally rewarding. My wedding, for example. The whole event cost a total of $500.

In my early 20s, I was living in New York City, and I’d take just about any job I could get. I waited tables mostly, but I also did all kinds of weird side gigs. One time a friend of mine started working at a cheap local gym that happened to have some famous members, like Madonna and the guys from Kool & the Gang—this was 1983, and their song “Celebration” was all over the airwaves. The owner of the gym wanted to do some grassroots advertising and hired my friend and me to ask other neighborhood businesses — bars, coffee shops, laundromats — if we could place ads for the gym inside their store windows. The lure for them was that if they let us put up a poster, they’d get a free membership to the gym and might catch a glimpse of Madonna or Kool & the Gang. For us, we got a couple bucks for every poster a business owner agreed to hang. It was a lot of door-to-door hustling. Fortunately, my people skills had improved since I was a kid with a paper route. But the posters didn’t seem to make a difference: Even with Madonna, “Celebration,” and all our grassroots energy, the gym didn’t survive. That said, I met a lot of interesting people around the neighborhood, and the money in my pocket helped me get by, so I don’t count any of it as a wasted effort.

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Over the years my relationship with money has shifted in some ways, but in other respects, it has stayed the same. These days, when I go into the grocery store, I’m not calculating the cost of each item. I don’t need to be as penny conscious as I used to be — I just grab and go. But I was raised to be conservative in my spending habits, so I always seek a balance: I don’t want to be a spendthrift, but I also don’t want to be needlessly lavish.

Every once in a while I treat myself with a special purchase. The most extravagant I’ve been is when I bought a Tesla not too long ago. I like the way it drives, and I really like the idea of reducing my carbon footprint. But often, I’ve found, the least expensive things can be the most personally rewarding. Take my wedding, for example. The whole event cost a total of $500.

Our wedding rings were only about $300 each. I’m really conscious about where gold is sourced—this was panned naturally from a river in Northern California.

I got married about 10 years ago to my wife, Laura, although we’ve been together for 30 years. We met on the set of Cheers. I was on that show for many years, and there were always visitors to the set — college classes and that kind of thing — but I never met any of them. One day a media workshop from UCLA was visiting, and someone suggested I go and say hi during a break. Laura was 22, and she wasn’t even supposed to go on the visit. Someone had gotten sick, so she took their place. Think about the serendipity: She wasn’t supposed to be there, and it was the first and only time I ever greeted random visitors. Very lucky for me!

Wedding rings can be extremely expensive, but ours were only about $300 each. Mine is one of my most meaningful possessions. I helped design the simple gold bands dotted with tiny, sparkling, colorful gems in various shades of orange, pink, and purple. The gold I already had. I’m really conscious about where gold is sourced, so I wanted to provide the gold and be sure of its origins. It’s gold that was panned naturally from a river in Northern California. All in all they’re pretty distinctive rings.

For the wedding itself, we didn’t feel the need to shell out a ton of cash and do anything over the top. It was basically just a bunch of good friends getting together in Maui. I paid for some food and drinks, a few hundred bucks, and that was about it. At the end of the day, it ain’t about how much it costs — it’s about having great people in a beautiful place and just…celebrating. Kool & the Gang would’ve been proud.

As told to Davy Rothbart exclusively for Wealthsimple. Illustration by Jenny Mörtsell. We make smart investing simple and affordable.

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