A few months before my 16th birthday, my mom wrote the below letter to Rick Reilly. I found it in my parents’ basement this past weekend alongside a One Headlight CD single from The Wallflowers. It’s a quick read:

If you don't ask, you don't get. Thoughtful.

Before Deadspin, before Grantland, there was the back page of Sports Illustrated. Rick Reilly wrote that back page in the late ’90s. In high school and college, my friends and I would rip those Reilly articles out, tape them to our walls, and get our sports commentary fix. Our brains were still forming, we appreciated puns, quick wit, and pop culture references- Reilly had a flair for the aforementioned trio.

Fast forward twenty years, we’ve got our Chrome bookmarks and Twitter favorites, and don’t much need scissors and Scotch tape to preserve our favorite articles. Now, HBO’s Bill Simmons is the sports journalist du jour, combining pop culture references with commentary on the games that to many of us, are embarrassingly more than just a game. But before Simmons, it was Reilly. He ruled the sportswriting scene.

My mom secretly wrote to Reilly, asking him to send me a few words of advice. I was interested at the time in becoming a sports journalist or a sports agent. How thoughtful of her:

“Yeah, he’d be happy with tickets to see the Metrostars, or a gift certificate to the Gap, but I just kept thinking how much your words on the back page of Sports Illustrated meant to him. And it hit me. What if I could get Rick Reilly to email him some words of advice about looking ahead, pursuing his dream?”

A few months later, Reilly wrote back. Well, he didn’t write back to her. He wrote to me. In the meantime, I probably did get that gift card to the Gap, but you can imagine the surprise when I received the letter below:


To me, that’s Reilly’s best ever work.

It’s not Mother’s Day today but why wait for Mother’s Day to expose such a hidden gem from my parents’ basement.

I’m really glad I found those two letters this weekend. My mom’s – a reminder of such a thoughtful move, and Reilly’s, a positive reaction to said thoughtfulness. It’s something that makes sense. If you’re thoughtful, and sincere, you can often make others happy, and use that thoughtfulness and sincerity for good.

Sometimes it’s nice to take a step back, take a deep breath, and realize that these are the types of people you want to surround yourself with. In business and in life.

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