Why We Sold Live Oak Lake

One of the most common questions I get is, “Why did you sell? Couldn’t it have been a long-term cash cow?”

Fair question, and I want to answer it in brief today.

When we built Live Oak Lake, we didn’t intend to sell right away. It was born of great sacrifice, and after the Airbnb suspension scare, it felt like riding a rocket ship.

But as some of you undoubtably know, running a hospitality business is a huge and heavy weight, no matter how much you automate or delegate. Every guest message, every maintenance issue—even the weather forecast becomes part of your mental load. When you’re prone to obsess over the tiniest things, it’s all but impossible to ever fully let go.

As my dad wisely put it to me at one point: “When everything is going right, that’s a reason to at least consider selling.”

Everything was going right—great press, astonishing social growth, and stellar guest feedback. They loved it, and so did I.

I’d always entertained the idea of selling if the right number came along, and eventually, I decided to test the waters.

the selling process

Six months after opening, we listed Live Oak Lake at what seemed like a staggering price—$6.3M.

But the timing just wasn’t ideal—six months of operating history is far less appealing to buyers than a full year. Plus, our broker didn’t specialize in unique hospitality assets, and while we did get some interest (including from a notable PE firm), no offers felt right. After a few months, we pulled the listing.

At the start of 2023, ​David du Menil​ from ​The Intrepid Group​ reached out. He specializes in outdoor hospitality and happened to live just down the road. We re-listed—this time at $7.3M. Soon after, we were under contract at $6.5M.

Here’s where my inexperience taught me a hard lesson: the nonrefundable portion of the earnest money was only $15,000. Due diligence went smoothly (having the local broker was a life-saver for the amount of trips onsite and coordination required for this process).

Two days before we were scheduled to close, the buyers set up a last minute, last steps / congratulatory call (I should’ve known).

I get on, and the sellers’ attorney tells us there’s been a delay with funding and they’re not able to close on time. They asked for two extra weeks. We reluctantly agreed.

Next day, they informed us they were out. Their lender had actually backed out weeks prior without us knowing it. They’d been unsuccessfully scrambling to find an alternative.

The $15,000 barely even covered my attorney’s fees.

Lesson learned, but I was pretty disappointed. (As a seller, always secure 1-3% of the contract price in earnest money to protect your position).

Just days later, we received another offer—$7M with $200,000 in earnest money. ​This buyer​ was much more prepared.

But a few days before closing, we get on another call: one of their investors had backed out. Now we had to decide: walk away with $200,000, or give them more time.

We gave them six weeks, and to their credit, though it almost all fell apart a third time, they came through.

what i learned

Running Live Oak Lake was deeply fulfilling and exhilarating, but it was also relentless.

Great hospitality is always relentless, and you have to love something about that to succeed at it. But there are builders and there are operators. I’ve realized I’m more of the former and a lot less of the latter:)

Selling was bittersweet. But the combination of all these things coming together felt right. Timing was right. Price was right.

The takeaway? Don’t force things. If it’s meant to be, it’ll be.

“Birds fly, fish swim, and deals fall through.” —Paul Graham

Hope this was helpful to any of you considering selling.

something personal

Early Christmas Eve morning, we welcomed our second son, Ezra Daniel. He was born at home, a day early, and we couldn’t be more elated. Mommy and baby are both doing wonderfully.

Lucas’ affection for Ezra has to be tamed at times (good problem to have I suppose 😊)

We are so extraordinarily blessed (though still a tad sleep-deprived).

Life is a miracle, and this is what it’s all about. I sincerely hope all of you who can get to experience being a parent one day. Nothing else like it.