A couple autumns ago, I was visiting family in Maine when one of our Experiential Hospitality community members, Eddie, invited me to tour a property he was working on - ten shabby cabins on a forested stretch of waterfront, forty minutes from Acadia. Built a century ago as an ironworkers' retreat, the place was half-collapsed, utilities pretty much nonexistent, a complete mess.

Eddie saw something else though, and went all in.

A couple months ago, that same property appraised at $2,000,000. And Eddie walked away from his refinance closing with every dollar of personal savings he'd put in - while keeping the property, the business, and the cash flow.

An “exit without exiting.”

Here's what it actually took.

First, the deal almost didn't happen. Eddie went under contract in 2022 and spent months in painful due diligence - only to have the sellers try to back out. He filed suit and spent $25,000 in legal fees forcing them to honor the contract.

After a year-long legal fight, he finally closed in December 2023 for $800k, with a $75k seller credit for the broken septic and water systems which essentially covered his $50k down payment and reimbursed his legal costs. He arrived at closing with effectively nothing out of pocket.

Then the real messy, fun work began.

The construction phase was brutal

After a lot of difficult “no’s,” he finally convinced a local bank to trust him with a commercial loan of $561k at 8.5% interest (ouch!), and a construction loan of $187k. The sellers carried a note of $189k.

Starting in early 2024, Eddie burned through that construction loan in short order repairing septic, water, and roads before touching a single cabin. What remained he stretched across maxed-out 0% business credit cards and a line of credit he’d built up.

By July 1st, he had fixed up five of the ten cabins. New bathrooms, interior walls, furnishings. Phase 1 hard costs: $280k.

This kind of white-knuckle bootstrapping makes me nod - the Live Oak Lake journey was full of the same thing. There’s a strange and comforting camaraderie in knowing you weren’t alone in your craziness.

The first summer was a great proof of concept - demand was real - but the property wasn’t designed to run at half capacity and he was losing money every month. Opportunity cost and speed to market, lesson complete.

At one point, sitting on the edge of opening for spring 2025 with hundreds of thousands in short-term debt and all his savings committed, he told me it was the most nerve-racking period of his life. He's 30, no dependents yet, and five years into taking calculated risks in real estate. Even still, this was his moment in the furnace.

He finished the remaining five cabins over the winter. Another $150k, with $100k of interest alone during construction and ramp-up.

Year 2 changed everything

With all ten units open, the property performed:

95%+ occupancy. ~$175 average daily rate. $330k in revenue. 35% operating expenses - a testament to the lean, tech-enabled model he'd built. $200k NOI. $100k net cash flow after debt service.

By November, he'd paid off every credit card and line of credit using the operating cash flow.

Then came the refinance.

The appraiser valued the property at $2,000,000 using a 10% cap rate. Eddie's bank was surprised - they'd committed to 80% LTV, then got cold feet. He pushed back, and they settled on 72.5% LTV: $1.2M at closing, plus a $250k line of credit for future projects (which he only pays interest on when he draws it - I think this structure is brilliant).

At closing, the funds landed like this:

$748k to pay off the bank (purchase + construction loan)
$189k to retire the seller note
$253k back to Eddie - essentially his entire personal investment returned

He created roughly $625k in equity. The property projects $60k/year in passive cash flow on a new 25-year note. And $250k sits available for whatever he builds next.

The cabins certainly aren’t “luxury.” They’re actually quite quirky. He did a lot of the work himself, on a shoestring budget. But they have loads of character. And this waterfront property - steps from the water, impossible to build today under current shoreline restrictions - will only become more valuable with time (follow the instagram here). Guests rave about the place.

A few keys

Eddie's story is a real life illustration of conviction. Of seeing something no one else wanted to touch, grinding through eighteen months of financial stress, and coming out the other side with something he’ll be proud to own, and reap the fruit of, for decades.

He wishes he'd moved faster on construction. He wishes he'd invested more in marketing. He wishes he'd documented more of the journey in public. I learned all the same lessons building Live Oak Lake, which is exactly why I’m sharing this story. If you’ve got a dream to do something similar, let our costly tuition count for something.

But, he did the thing.

And somewhere out there - maybe forty minutes from a national park, maybe along a forgotten river, maybe at the edge of a small town that used to be something - there are hundreds more of these properties waiting for someone with the eyes to see them.

You don't need hundreds of thousands in savings. You need a dream and a work ethic. And a high tolerance for pain.

Capital can be assembled, conviction cannot.