This is the third issue of my monthly newsletter, originally sent to subscribers on July 25, 2026.
Patience
This month has shown me the difference between a typical full-time job and investing as a full-time job.
As an employee (and especially as a business owner), you learn that success loves speed. The more you do, the faster you can turn the flywheel in your life. You take massive action to get massive results. However, as an investor, you have to be prepared to sit on your hands and do nothing for long stretches of time.
I feel like I have to de-program from the entrepreneur and corporate world to make this new chapter work. I would love to tell ya’ll about all the amazing deals I’m doing, but … I’m not.
In fact, in the last update I told you that I had just signed my second SMB investment (woo!). Yesterday on my call with the sponsor he told me that I won’t be able to invest (boo!). Turns out their debt stack changed, so they don’t need as much money, and their primary investor wouldn’t shrink their allocation to leave room for anyone else.
This means that I’m unlikely to have something investing-related worth sharing every month (or at least that’s my fear). So hopefully you like to hear all the stuff I do while waiting for the right deal, too! 😅
… and Focus
While it’s true that I have to wait for the right deals to come along, I can’t just wait around for the right deal to find me. I’m already plugged into a lot of business broker lists and SMB investor groups, so I receive a steady inbound opportunities. But the volume isn’t high enough for me to quickly develop intuition across such a broad range of businesses, or feel like I’m being selective enough in my due diligence.
If I’m going to be selective with what goes on my 20-slot punch card then I need to watch a lot of pitches go by. A common refrain I’ve heard from larger investors, funds, etc. is that they invest in less than 1% of the deals that cross their desk. That all starts with a large(r) top-of-funnel.
Here’s what my funnel looks like right now:
(I’ve blacked out business names, cash flow, locations and links.)
Ok, this is maybe 5% of what actually hits my inbox. But I’m only considering sponsored deals because I don’t want to be the CEO / operator myself for the next couple of years. Instead, I’m focused on minority investments brought to me by self-funded searchers. Sadly this is not the majority of my inbox.
One thing I’m starting to do is identify people that would be strong operators that I could buy a business with, especially if they’re willing to relocate for a new business. Although I have a couple friends that I’m casually looking for businesses with, I should be more intentional about this option. This would open up a world of opportunities versus just the existing sponsored deals.
To that end, I’m starting to take calls with people searching for a business before they have a business under contract (“pre-LOI”). If I can find a few partner operators to buy businesses together, that would be my ideal scenario.
P.S. if you’re interested in running your own business and want to buy one together (especially if you’re willing to relocate), let’s talk!
⚕️ Special: What about health insurance?
I’ve been asked what we’re doing for health insurance.
tl;dr - Our family is better off with COBRA for now, despite the price. Consulting a health insurance broker is a no-brainer. They get paid by the insurance carrier so, if you don’t use one, that’s just extra profit to the carrier. While most of them don’t technically have a fiduciary duty to you (so do your own homework too), it’s pretty easy to compare their plans against your COBRA and ACA options, at least.
Here’s a great talk discussing post-W2 health insurance options, and includes alternatives to the ACA marketplace, such as small group insurance and self-insured group health plans via unions or associations.
After this talk, I spoke directly with the speaker Amber Flanagan (brokerage). For my situation, she steered me to stay on COBRA. Obviously this doesn’t make her any money but she did it anyway, which builds my trust in her.
So why am I staying on COBRA? The ACA marketplace plans are all state-specific and sometimes region-within-state specific. This means that you can’t see any providers outside your state or home area, other than emergencies. As a nomadic family who spends significant time in Tennessee, Arkansas, Illinois, Colorado, and other states, this doesn’t work for us.
Amber told me about some small group plans with national carriers that would save a couple hundred dollars a month, but most of them have a significantly higher out-of-pocket max. Since we’re planning to have a baby in the next year (and using IVF), which will almost certainly max the deductible and out-of-pocket, it’s likely to be more cost effective for us to stay on COBRA for now.
That all said, Confluent’s transition into IBM is changing my COBRA options again, so we’re going to be re-evaluating soon. We’ll see if anything changes.
🚐 How was the road trip?
One of our favorite things about traveling is meeting up with family and friends in new (and favorite) spots!
Going clockwise, the top photos show me, my wife, and my parents after a Waffle House breakfast in Arkansas; my daughter and mother-in-law dancing outside the Dierks Bentley bar on Broadway in Nashville; KPOT Korean BBQ with our niece in Charlotte, NC; hiking the Spruce Flats Falls trail in the Smokies with friends we met at a Mr. Money Mustache meetup in 2016 (the only one we ever attended)!
One of our favorite things about living in Nashville (when we’re there) is Layla’s on Broadway. Layla’s always has the best new artists. Our favorite act this time was David Graham and Slick Joe Fick, accurately known as “the Energiser Bunny of slap bassists”. Together, they deliver a super high-energy rockabilly performance.
North Carolina gets a special callout for my favorite pro-education sign. And Georgia gets a callout because during one beach trip, we saw a man catch-and-release a 5-foot blacktip shark, took a bridge across a venomous snake nesting ground, and saw a sign for a restaurant claiming to have both “gators” and be “pet friendly” 🤨
The final stop on our road trip was the Wilderness Resort, our favorite waterpark in the Wisconsin Dells, with my “Chibundance” crew and their families (shamelessly modeled on Gobundance).
As fun as this all was, the potentially most-impactful takeaways from places that we added to our might-settle-down someday list:
- We absolutely loved Asheville. It has the charm of a mountain town, but it’s a real city with nice walkable pockets.
- But Serenbe, GA has so much that we want in a home town for our children and our family. I’ve spent so much time deep diving into everything, including its organic farm and CSA, the EarthCraft/geothermal/solar-ready homes, the diverse Serenbe Art Farm with its variety of performances, local schools, a variety of theaters, many kinds of museums, symphonies, great sports, and even a local Polish School.
That said, we have a full agenda for the rest of 2026 and 2027 … maybe 2028? 🤷♂️
✈️ My first flight!
The road trip helped me accept that our “living large” nomadic journey will eventually be replaced by a “living local” lifestyle. This caused me to reflect on how we can structure our lives at that point to build deep roots within a community, continue spending significant quality time with both families, and still get to travel to new places every year.
This led me to the decision to start training for my private pilots license (PPL) with the mission of supporting regular cross-country family flights. I suspect this will take 30+ months given our schedule, so better start sooner than later!
🌎 Where are we traveling next?
- 🇨🇷 We’ll be living in Costa Rica from August through the end of October. Fingers crossed that we come back with a bun in-the-oven if our Costa Rica IVF journey is successful!
- 🇺🇸 We’ll spend holidays with our families in Arkansas and Chicago.
- 🇯🇵 We’re going to worldschool our children in Japan in Q1 2027.
We are very “open itinerary”, so if you want to meet up with us or know someone we should meet along the way, reach out and let us know!