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
