The night before these things, I never sleep well. No matter how early I try to get to bed or how dialed-in my nightly routine is, the breath work, the wind-down, all of it, I still don’t sleep before a big event or a big interview. I think that’s pretty common. I’m not outside the norm on that.

In this case, I’ve flown to Atlanta to interview and hang out with someone I’ve modeled myself after for a while: Jesse Itzler.

If you don’t know Jesse, he’s the billionaire founder/partner in companies like Marquis Jet, Zico Coconut Water, the All Day Running Club, 29029, the Big Ass Calendar company and more. He’s also a part-owner of the Atlanta Hawks, a multiple New York Times bestselling author, ultra-endurance athlete, speaker, husband, and father of four. 

He’s our kind of guy. A doer. An adventurer. The kind of guy we can all learn from. And the kind of guy who when you meet, you never know exactly what you’ll get into.

That’s why I packed three outfits and a bunch of gear. I brought a bathing suit. I brought goggles. I figured we’d get in the sauna, the cold plunge, maybe go for a walk and talk. I packed shorts and running shoes. I had no idea and I wanted to be ready for anything, so I packed a big bag.

As for the interview, I had one outfit I thought would work for that part of our day, but I debated the beanie. 

Do I wear it, do I not wear it, do I go super casual, do I try to dress like him, do I just dress like me? 

Ultimately, I always dress like me. I did wear a beanie at first, but when he walked in wearing one too, I thought, there’s no way I’m doing an interview with two guys in beanies. So the beanie came off. I felt better instantly.

I got to the house super early. I was supposed to be there at noon, and I did not want to screw this up. I also know from following him for a while that Jesse doesn’t eat anything but fruit until noon, so I ate a huge breakfast wondering if we’re going to eat during the day at all and now that big morning meal is all swirling around in my stomach along with my nerves.

I’d also heard he doesn’t eat or drink much the rest of the day either, so I’m planning ahead because I’m the opposite. I’m always starving. I eat every hour. 

So I stuffed beef jerky in my bag, power bars, bananas, anything I could grab quickly.

Around 11:30, I’m sitting in front of the house, thirty minutes early, because you never want to be late for something like this. 

And to be clear, this is more than a house. It’s like a full-on compound on a corner lot with three different entrances: a service entrance, a main entrance, and another entrance with signs pointing you around. 

There are probably thirty cars in the driveways and along the road. 

I’m thinking, “Holy crap, this is a major operation.”

I text Alex, the CEO of The Big Ass Calendar Company, right at noon: I’m here. 

He comes out, grabs me, and we walk in. We pass the main house; we’re not going in there. That’s where they live. Makes sense. We walk past the football field, past the tires on the hill you can flip, past the garden I’ve seen in all the videos where Jesse pulls his fruits and vegetables.

Workers are in the driveway cutting wood, building shelves, doing something - no idea what exactly. Then we pass the garage. He’s got a nice lineup:

Rivian. Range Rover. A vintage Mustang.

I say, “Nice car.”

Alex says, “I’ve never seen him drive it.” 

Point taken.

We walk up a big flight of stairs to what I guess is the pool house, where Sara Blakely’s office is upstairs (if you don’t know, Jesse’s wife is the billionaire founder of Spanx). 

The pool itself is massive. Starting blocks, lanes, the whole deal (our Editor-in-Chief and resident swimmer, Jon, would be very jealous). 

Behind the pool is a basketball court and a pickleball court. The pool house sits between them, all glass on both sides so you can see everything. Inside, there are two hyperbaric chambers. The whole place is stunning.

They’ve got the setup ready for our shoot. Bathrooms, kitchen, everything you need. This place is awesome.

I get settled. I meet Bryan, the videographer. Alex and I talk shop for a bit. Jesse’s supposed to show at 12:30 and rolls in closer to one. He’s working on this big show in New York, so he had a meeting beforehand. He comes in smiles, and…

Read PART TWO, including what we discussed, how we hopped in the sauna and a full video of our conversation, on Sunday! Subscribe here to get it delivered to your inbox.

You know what the easiest way to plan a big ass 2026 is? Simple. Use Jesse Itzler’s Big Ass Calendar or Planner. It’s what we use at Midlife Male because it allows you to put EVERYTHING you want to accomplish, achieve and do next year in one big spot. 

Forget calendar apps you never check. Forget those old flip calendars you get at the grocery story with barely enough room in each square to write a birthday.

Use the BIG ASS CALENDAR to write down your Big Ass Goals and Events.

Order it here with a Midlife Male discount

BONUS: We’re going to be coming out with a set of MLM printable stickers that you can use to mark the Midlife Male events you’ll be able to attend, along with how to use the color-coded stickers the calendar comes with for each of our 6Fs.

In health,

Midlife Male
52. Husband. Father. Entrepreneur. Coach. Mediocrity happens by default. Maximization happens by design.

PS: Want to set the tone for the best year of your life?

Let’s talk. I have a few openings left for 1:1 coaching and my private adventure group. It’s not about resolutions, it’s about resolve. Book your call with me to see if we’re a good fit here.

At 52, I’ve learned what I wish I knew in my late 20s and 30s, that fertility isn’t just a women’s issue. Men struggle too, often silently. I did and I didn’t know it. We assume our virility and vitality will always be there until they’re not. Fertility is about more than making babies. It’s about hormone balance, energy, and long-term health.

I’m done having kids. Mine are already in their 20s. Ironically, you spend a lot of years as a parent hoping your sons don’t get anyone pregnant, and then in your 50s, you start envisioning becoming young grandparents. I want my boys to be educated.

That’s why SwimClub matters. It’s science-backed, built for men, and focuses on the key drivers of male fertility: sperm health, testosterone support, and reducing oxidative stress. It helps you feel better, perform better, and preserve what matters most.

If I’d known then what I know now, I would have started taking care of this part of my health much earlier.