My Happy Place (and why every founder needs one)

About five years ago, when my son turned five, a big-time CEO mentor of mine gave me some advice: "Get your family skiing, Jesse, because it’s the one trip your kids will take with you until they are 30!"

The reason? It’s expensive.

About a year later, I took the kids skiing at a local hill here in St. Louis (with a 300-foot elevation), and it was MY first time skiing. 

I thought it was cool, but BOTH of them, at ages six and four, fell in love. Later that year, we went to Deer Valley in Utah, and the whole family thought it was magical.

It's become one of my happy places.

About a year later, we bought a condo there so we could commit to really spending time out there. It's been one of the best purchases I've ever made.

And the biggest surprise? It's just as fun in the summer as it is in the winter!

A few weeks ago, we took a trip there for the summer. Here is the rundown:

On Sunday, we arrived and got settled in. We brought a close family friend from St. Louis with us, which was a huge treat. 

Everyone got along, which is rare. We checked out downtown Park City, went on a brief hike and played some video games.

On Monday, the kids went horseback riding. Serena was pumped because she got the same horse as last summer, Stuart. 

I relaxed, worked out, and then everyone went to the pool. We ended the night with an adults-only dinner at Yuki Yama!

On Tuesday, we went on a big family bike ride in the morning. Mila (almost two now) biked with me and fell asleep. 

In the afternoon, we went up to the top of the mountain. It was absolutely breathtaking.

Ricky insisted on hiking down, and so we did a two-to-three-mile hike descending 2,000 feet!

On Wednesday, we took a boat and Jet Ski out on the Jordanelle Reservoir. It was STUNNING. I taught Ricky how to drive a Jet Ski, and we formed a core memory.

On Thursday, we went to the Olympic Park, which was super fun — tons of ziplines, alpine slides and ropes courses. 

Everyone had a blast. The highlight was watching people practice ski jumps into a huge pool in the middle of summer!!

On Friday, we headed back to St. Louis, where my last remaining childhood friend got married.

It was such a fun time, as the whole band got back together, and we all goofed around the whole weekend. I also gave a roast-y speech about him with my older brother, which was a hoot!

So, why am I telling you all of this?

1. What you think I rap for?

There's a famous Kanye line: "What you think I rap for, to push a f****** RAV4?"

I find myself repeating this to a lot of founders. There are lots of reasons to be an entrepreneur, but one of them is to have both freedom and money to ENJOY life! 

Almost everyone starts that way, but sometimes along the way, they forget–or think THEY MUST GRIND to have success.

Don't get me wrong, grinding is important. But so is relaxing, enjoying life and connecting with family and friends.

2. Find a happy place

I think there's huge value in a place outside your home city or area where you can make memories. Yes, I love visiting new places. I love the adventure and figuring it all out. 

But let's face it, there's also some nervousness and discomfort there.

Having a place you frequent allows everyone to be together in a focused way, feel comfortable and enjoy instant connection.

It's been a game-changer for our family.

3. Breaks make you more productive

In the first 12-18 months, yes, every new company is a GRIND. 

But after that, the decisions you make—where to spend time or money, which strategy to pursue or what culture to create—have much higher impact than constantly grinding. 

Better decisions happen when you give yourself space to think and just be.

Give it a shot and tell me what you think.

jesse