One year ago I owned 3 businesses:
- Boutique hotel in downtown St. Louis
- 7-figure ecommerce business
- 150+ person agency
Fast forward to today and I've sold all 3.
1. Somewhere.com – May of this year, I sold a controlling stake in Somewhere (formerly Shepherd) at a $52m valuation. I stepped down as CEO and took a $26m payday. I still own ~13% and have a seat on the board as an advisor. I’m pretty open about it because terms of the deal were shared publicly by everyone involved. More here.
2. Peel – September of last year I sold Peel, the e-commerce brand I’ve owned with my buddy Jon since 2013. It was a very modest acquisition. Side note: Jon is now a famous on TikTok and Instagram for hand making leather soccer balls. View his amazing videos here.
3. The Ludwig – In June of this year I sold The Ludwig building, our boutique hotel / mixed use building. We started it in 2017.
Now what?
After divesting of my main 3 businesses, I’m taking time off.
I’m “retired” which means I’m spending more time with my wife and 2 kids, investing more time in forgotten (and new) hobbies, playing with my cars, and tinkering on projects. I’ve always loved writing and sharing lessons learned, so here we are.
It’s been about 3 months since I had my big exit. I’ve bought a few cars, took a bunch of vacations, had a lot of nice dinners and cocktails.. and now life is back to normal again.
What am I doing with the money?
For me entrepreneurship is the “risk” bucket of my investment portfolio. Now that I’ve made money, I’m taking the boring conservative approach and putting it all into index funds and bonds. If I can grow my investments at an average of 8% for the rest of my life, I’ll be very happy.
I've made some small real estate and PE investments as well.
What I did to celebrate
I absolutely love cars. Always have. So I indulged and bought a few I’ve had on my list:
1. 993 Generation 911 Carrera S. blue interior with the hardback sport seats.
2. 911 GT3 in PTS British Racing Green with buckets, 6 speed manual, and carbon ceramic brakes. This was my dream color find. It nearly matches Somewhere’s colors.
3. AMG G 63 for Jaimie... but who are we kidding, I drive it a ton too.
4. I also bought my parents a new car as a THANK YOU.
I took a bunch of trips
- Cabo with my old college roommate
- Colorado Springs iwth my wife and kids
- North Carolina for 2 weeks (city, mountains, ocean)
- Booked a 2 week trip to Europe with my wife and parents to celebrate my mom's retirement
Today
I had a lot of fun in the aftermath of the acquisition (I still am!) but it’s time to focus on my health. In my opinion, if you’re rich and have a lot of time on your hands, there’s absolutely no excuse for being unhealthy.
We did a lot of indulging but now I’m going hardcore.
- I’ve been working out with heavy weights 3 days a week in our home gym and eating a much more strict diet. The goal? Get ripped.
- I’m trying to go from 16% body fat to under 13% while packing on more muscle.
- I’m headed to get my blood drawn to get a baseline for a lot of health markers, but mainly checking my testosterone levels. I’m 34 and aiming to increase my T levels naturally.
- I just signed up for a stem cell treatment for my hair. I’m not balding, but my hairline has receded. Apparently stem cells have been proven to reinvigorate dying hair follicles. I’ll report back in 6-12 months with how that worked.
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