This year was full of big life changes! Here's just a few...

• I sold my business for $52,000,000
• We decided to leave Texas and move to North Carolina
• We bought land / designed a custom home
• I got super fit
• We experienced a home invasion in Spain

I wanted to take some time to reflect on what went well, what didn’t, and everything that happened in between. I also share some of my goals for 2025.

The Highlights - What Went Well

This year I turned 34 (my birthday is January 1… so I’m now 35 as I write this in the first few days of 2025), my wife and I celebrated 7 years of marriage, my son turned 4 and our daughter turned 1. Below are the highlights of some good things that happened in business and my personal life.

Business Highlights

A big theme for me this year was “deloading”. I sold all 3 of my businesses. I had an offer to sell Somewhere for life changing money, so I took it. I also decided to sell the other 2: Peel and our boutique building in downtown St. Louis called The Ludwig. I did this purposefully to give myself a break after 15 years of starting / running my own businesses. I called it “retirement”, but it’s really been a sabbatical. My wife jokingly thought I wouldn’t last 6 months before I’d start another business. It’s been 8 months since I sold and I’m making plans to start another business (hah!).

I sold Somewhere.com (formerly Shepherd) at a $52m valuation to Nick Huber and a group of investors. Terms of the deal are public so I'll save you the search: My package was $26m as a mix of cash and a seller note. I also kept 13.5% of the business to continue receiving profit distributions. Fun fact: it was exactly 4 years from 1st revenue (April 2020) to the acquisition (April 2024).

We hit 150+ employees at Shepherd just before selling with a full management team in place.

I stepped down as CEO and handed off the reigns to a new majority owner and CEO. I no longer have a daily role. I sit on the board and wil advise the business.

We spent $400,000 buying the domain Somewhere.com and rebranded Shepherd to Somewhere. I’m a sucker for premium domains but this is by far the most I’ve ever paid for a domain. The seller agreed to allow us to pay for it over 18 months, so the impact of the cost is nicely spread out.

I sold The Ludwig, the boutique historic building I've owned in downtown St. Louis since 2016. A lot of memories owning this building -- I got married in it, I lived in it, I had the original Need/Want office in it, we built 14 short-term rentals in it, and more. I’ll share more about that deal in a future article. We closed the deal June 10th.

I sold Peel to a private equity group. I had owned it for 10+ years. Technically that deal closed at the end of 2023, however for various reasons it dragged into 2024. I’m still dealing with some final post sale items.

My rental property in St. Louis continued to cash flow well with little inputs from me.

​Somewhere continued to grow and be profitable. It’s been nice not needing to touch the sale proceeds. My minority stake in Somewhere’s profit distributions continues to fund our living expenses after selling the business.

My stock portfolio did great in the S&P500 after moving the sale proceeds into a mix of high yield bonds and index funds.

I was on 2 great podcasts:

• Money Wise from Sam Parr [Spotify Link | YouTube Link]
• Andrew Wilkinson's Never Enough podcast [Spotify Link | YouTube Link]

​I invested in 4 real estate private equity deals across self storage, retail, and industrial storage. I decided to stop angel investing. I’m going to be boring and only invest in stocks, real estate, and a little bit of bitcoin. Any startup investing will now only be in stuff I’m going to be involved in directly as a founder or buyer.

‍I started my personal newsletter again and hit 14k subscribers. I cover business lessons learned and what’s interesting to me.​

Personal Highlights

‍I “retired” after selling Somewhere. We’ll now call it a sabbatical. I used my extra time to do a lot of traveling, working out, designing a house, and quality time with family. I’ve also picked up writing like this again. Subsequently my Twitter follower count grew a lot this year from posting more content.

‍I put on 10 - 12 pounds of muscle by lifting and getting my vitals dialed in. I started seeing a Functional Medicine Doctor. This basically means getting blood work every 2-3 months to test a full panel of markers. We then tweak with lifestyle, supplements, hormones, etc based on those findings. It’s been a game changer for energy, mood, and my ability to build muscle.

I bought a bunch of cars – Porsche 911 GT3 in "british racing green", a vintage 993 generation Porsche 911 Carrera S, bought my wife a "G wagon" (AMG G 63) and sold our Tesla Model X. I also sold my Lotus Exige S 260.

We got a dog. Margaux is a 50lb English teddybear twoodle (schnoodle and English goldendoodle mix). She's so sweet and great with our kids. Even though she has long hair, she doesn’t shed!

Our 2 kids are thriving and healthy. They’re both so smart and talk extremely well for their ages. I love both of their unique personalities. Our daughter is a daddy’s girl with a sassy personality. Our son is so sweet and goofy. As his teacher tells us, “He’s sweet but with the right amount of naughty”.

I bought my mom & dad a new car.

Took my parents to Europe for my mom’s retirement (and to celebrate mine). We hit Paris, Barcelona, then 7 days on a cruise through the mediterranean, and then 2 days in Monaco before flying home.

I setup a Donor Advised Fund to continue our charitable giving with 10% of our income.

‍In September I took 1 month off of drinking.

Benjamin Surman became a close friend (He's COO of Shepherd / Somewhere.com). He lives near me and we have a ton of in common. Looking forward to continuing that friendship. We will start something together in the future.

‍My wife and I decided we’re done living in Texas and went on a hunt for a place that’s right for us. Q1 we explored many options and ultimately chose Raleigh, North Carolina.

‍We bought 1.5 acres of land in Raleigh, NC with the intentions of building a custom home.

‍We spent 9 months designing our dream home. We have a great team for the house: Tony Frazier did our plans and exteriors, NOBLE on the interiors, and Loyd Builders for the construction. We can't wait to finish the house in 2025 and move in. I’ll be sharing the progress and photos on my Instagram.

​TraveI

I took a lot of trips this year!

• Nashville for New Years
• Raleigh in January
• Paris + Marbella for the month of February
• Raleigh again in March
• Cabo with Jaimie
• Cabo with my best friend Russell
• Colorado Springs
• Raleigh again in July
• Cabo in August
• Austin, TX in September
• Raleigh in October
• Paris, Barcelona, Mediterranean Cruise, Monaco (1 trip with parents)
• Our cabin in November and December

​What Didn't Go Well This Year

It wasn’t all celebratory champaign and adventures in 2024. There was some hardship along the way this year.

‍We experienced a home invasion. I rented a house for a month in Marbella, Spain that we intended to live in for all of February. On our 4th night there, at 3am someone broke into the home. We ended up hearing them and once we jumped out of bed, my wife came face to face with one of them at her bed side as she was closest to the doorway. She screamed at them, which startled them to run. It was a horrible experience I wouldn’t wish on anyone. The next day when we filed the police report, we learned there were multiple break-ins that night, with some of the guys tying up / assaulting victims in their homes.

If you want to read more of the details, I did a breakdown here on Twitter with photos -> ​

Dealt with awful sleep issues from the break-in. Both Jaimie and I dealt with nightmares and sleep issues for months. Being able to sleep well has always been my super power and I feel like I lost it this year. I’m working hard to get my sleep quality back. We now take personal safety very seriously and have enacted a lot of security measures in our lives.

‍Jaimie dislocated and broke her arm at the elbow playing tennis. She had to have an emergency surgery, adding a plate and 12 screws through her elbow. She’s finally recovering well after a ton of physical therapy. Due to her injury, she couldn’t do much with our kids so I had to basically be a full-time stay at home dad for 6 weeks.

Dealing with buyers of Peel has been a huge a big pain in the ass. I'm still dealing with it in 2025.

‍I had to cut a massive tax check from my sale proceeds. While I recognize this is a big privilege to write a big tax check from a sale, some businesses when sold allow you to not pay taxes on up to $20m in proceeds due to something called "QSBS". However, I wasn’t able to because of the structure and nature of my business. So I had to pay the government 7-figures in taxes *gulp*.

‍Our new dog had a slew of health issue (vomiting and diarrhea for MONTHS). I’m talking I would wake up at 5am to her sitting in a pool of her own diarrhea or vomit in her kennel. This would happen 2-3 days in a row for months. I was close to asking the breeder to take her back. I think we’ve finally turned a corner and got it all under control. Not after spending thousands on vet bills and tests. A simple daily low dosage antibiotic on her food is what finally did the trick.

‍All the new changes = a lot of work and stress. We’re looking forward to feeling settled in 2025. Searching where to move, designing a house, finding a builder, and the logistics of a cross country move were a lot this year.

Things I’ve Loved in 2024

• ​Oura Ring – I ditched my Apple Watch for nice mechanical watches. The Oura Ring tracking is so good, especially the sleep data. You forget you're wearing a tracking device.
• ​Money Wise podcast – a podcast about rich people stuff no one else talks about publicly. How much other wealthy people spend per month, the psychology of suddenly becoming wealthy, portfolio breakdowns, what it's like to have various things like a giant home, or what it costs to own a private jet. It's wildly fascinating to me.
• Seeing a Functional medicine doctor. I can't say enough good things about working with one.
• Working with a private bank and financial advisor. I'm so glad I found the one I'm working with. They're awesome. Shout out to Griffin 👋
• My vintage Porsche 911 is probably my favorite. That car has so much soul.
• Pickleball
• Some books I enjoyed:
  1. ​Never Enough by Andrew Wilkinson. I read a pre-release copy in 24hrs. It had me hooked from the start. I've been fortunate to call Andrew a friend for the last 10+ years. I still learned a ton from it and things I didn't know about him. He's very transparent in the book in both business numbers and psychologically.
  2. ​How to Live an Extraordinary Life by Anthony Pompliano. He wrote it as letters to his kids, sharing all the things he's learned and wants to pass down. I loved the format.
  3. ​The Algebra of Happiness by Scott Galloway. Lots of great nuggets of wisdom.

​What’s Next - What I’m Looking Forward To in 2025

While I have specific goals for 2025, the general themes are:

1. Make content consistently
2. Build a new business
3. Get super ripped

​For business, I plan to launch a new company with a good friend of mine in Q1. I have a profit goal in mind for that business. Additionally I’d like to do 25+ newsletter sends, hit 100k Twitter followers, and grow my net worth by a certain %. I might try my hand at short-form business video content. First I want to get consistent with writing regularly though.

‍For health and fitness, I want to see if I can hit 10% body fat while growing my lean mass. My last DEXA scan reported 13.5% body fat. I want to do a 7 day dopamine detox each quarter of 2025. I also plan to see how no sugar for 30 days affects me.

‍For life & family, I plan to move to Raleigh, finish our custom home, get good enough at tennis to play with my wife, go on 40 dates with her. I have some travel and adventures planned personally and with my family. There are some road trips I want to take with my car buddies, visit Europe again, and summer in Colorado. Finally, I’d like to spend less money this year than last (besides the house). Our spending is fine, but i’d like to see if we can spend less and still enjoy ourselves just the same. Looking to find the “sweet spot” of monthly spending for our family.​

Overall 2024 was life changing for me with the acquisition. I feel blessed and excited. Life is good. I have a lot to look forward to in 2025. Onward!

Thanks for following along.