This is me.

When I was in my 20s, I got really lucky.

I started a business with some buddies. We were in the right place, at the right time, with the right product.

It changed my life.

We built that business to about $10 million in revenue. We paid ourselves real salaries. And we went through everything that comes with it – mistakes, losses, firings, resignations, lawsuits. The whole deal.

I won’t bore you with all of it, but three things happened during that stretch:

  • I learned a hell of a lot
  • My wife got pregnant with our first daughter (we now have two)
  • And somewhere in there, I fell in love with golf

Around that time, my wife suggested we move from Austin back to Pennsylvania, where we both grew up, and where most of our family still lives.

I didn’t want to go.

But sometimes, when you’re married, you disagree and commit anyway. That’s what being a good teammate looks like.

Take notes, fellas.

Anyway, we moved back in 2022, and she was right – it was the best decision we could’ve made for our family. There’s nothing better than raising your kids around people who love them.

If you’re reading this, please send it to my wife so she knows I publicly admitted she was right and I was wrong. Thank you for your time.

I’d love to say that was the only time I’ve been wrong, but I made a few more mistakes in that stretch – and somehow, they all led to Caddyshanks.

Where I Got It Wrong

Moving wasn’t the only major life event happening at that time.

Within a pretty short window, I:

  • Walked away from the business I had spent most of my 20s building
  • Sold our house in Austin (after a failed Airbnb attempt)
  • Had our first child
  • Bought two small golf businesses with my brother Jesse and my friend Jon

If you take nothing else from this article, take this:

Do not stack every major life decision on top of each other.

Because I did.

And I wildly overestimated myself.

The two businesses we bought were easiergolfing.com and bodyforgolf.com.

Easier Golfing sold a swing trainer called The PowerFlex. Body For Golf sold a few fitness E-books, which we still sell today.

At the time of purchase, the two businesses combined for about $25,000 per month in revenue – most of it coming from the PowerFlex.

There were thousands of positive reviews. We were working on bringing shipping in-house to improve margins. Everything looked stable.

I felt like a genius.

I had analyzed search volume, spotted a trend, and thought I was skating to where the puck was going.

Then reality hit.

Within a few months, Amazon released an Amazon Basics version of the PowerFlex.

Same concept. Lower price. Infinite distribution.

Overnight, our sales cratered.

We couldn’t compete and I was reeling.

I had walked away from a comfortable salary. I was living off buyout money. We had a newborn at home.

And the business I had just convinced my brother and one of my best friends to buy with me… got crushed almost immediately. (By the way, we still have about 1,000 swing trainers sitting in Jon’s garage if you want one.)

The Pivot

But there was one piece of the business that didn’t break.

The newsletter.

When we bought the sites, they came with a small email list – a few thousand subscribers. Over time, we had learned how to sell ads to brands trying to reach a golf audience.

It wasn’t much. A few hundred bucks a month, but it was profitable.

And more importantly, it was ours, and not something that Amazon, or others, could easily replicate.

So we leaned into it and slowly, it started to grow.

Not enough to pay a salary. Not even close. But some advertising dollars were rolling in. Enough to cover its costs. Enough to keep going.

For a long time, I wrote and sent the newsletter 3x per week to almost no one.

There was just one problem – I couldn’t work on something that made no money forever, no matter how much I enjoyed it.

So we did what a lot of people in that situation do.

We started something else.

We launched a marketing agency. We started another newsletter. We pieced things together.

It wasn’t glamorous, and it wasn’t clean, but things were starting to work.

Where We’re At Now

Fast forward to today.

We run a marketing agency called That’s Crisp. We help clients – mostly in sports – create content, grow their audiences, and build their brands.

Last week, we were credentialed media at the JM Eagle LA Championship, an LPGA event, with one of our clients.

That was a bit of a “holy sh*t” moment for our small team. We got to meet great people, shoot content, and be inside the ropes at a professional golf tournament – not something I saw coming a few years ago.

We also own two media brands:

Caddyshanks, for golf, and Dad Day, for dads.

You can check out our deck for the two media brands here, if you’re interested.

I’ve written Caddyshanks three times a week, every week, for over three years now. I love it – it doesn’t feel like work. I get to talk about golf, make picks, tell stories, and try to figure out how to deliver as much value as possible to people who care about the game as much as I do.

On the other side, Adam Kunes has been the driving force behind Dad Day. We’re really proud of what that’s become – a private Slack community for dads, real-world run clubs and events, and now a YouTube channel focused on telling the stories of great dads.

In a few weeks, we’ll be launching a Caddyshanks YouTube channel as well, with some crossover episodes highlighting dads in the golf world.

It’s funny – a couple years ago, I thought the big win was buying those golf businesses. Now, the best parts of what we do are the things that don’t feel like work at all, and through a series of happy accidents, we’ve ended up with with a real business.

And for the first time since all of this started a few years ago, it looks like I might even be able to take a small salary this year.

If you made it this far, I appreciate you reading. If you ever want to connect, shoot me a note – josey@caddyshanks.co