🥒🟢 The Night I Stepped Onto the Court (And Into Something Bigger)

It was snowing. I had no paddle. But this one night in Michigan changed everything.

I didn’t plan on becoming a pickleball guy.
It wasn’t some fitness goal.
It wasn’t part of a content strategy.

It was just a snowy night in Michigan, and I needed to move. To breathe. To get out of my own head.

I showed up at Borden Park in Rochester Hills for RARA Pickleball 101 with zero expectations and even less coordination.

But Blair and Morn💚 - who run the show here in Rochester Hills and founded the Michigan Pickleball Association (click to join the community) - welcomed me like I already belonged.

If it weren’t for them, it probably would’ve taken me months to fall in love with the game.

Instead, it happened that night.

I left with my heart racing, my paddle hand numb, and a weird sense that something had shifted.

🏡 I’ve been helping people navigate real estate for over two decades - turns out, it’s a lot like learning pickleball: it’s easier when someone shows you the court, the rules, and where to stand.

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It wasn’t just the game - it was the energy.

The people. The laughter between points. The connection.

I couldn’t explain it then, but I knew I was going to keep coming back.

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So that’s what this newsletter is.

Not pickleball tips.
Not real estate market noise.

Just real stories from the court and the closing table - and the stuff nobody talks about but everybody feels.

I’ve been in real estate for over 20 years, but I’ve never had a space like this to share what I actually think about business, life, relationships, mindset - and now, this game that’s somehow become part of all of it.

They say top 1% agents don’t play games — but clearly, I do 😉
If you ever need help making a move, I’m your guy.

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If you’re into that - hit subscribe.

If not, no hard feelings.

But don’t be surprised if you circle back later when you’re nosy and want to know how this all started 😉

Big thanks to Blair and Morn. This Drop wouldn’t exist without you.

– Dylan

p.s. If we’ve played together, you’re part of this story too.