Twenty years in real estate. One operating principle.

I started in real estate in 2005, while I was still working in risk and compliance for some of the largest financial institutions in the country — Bank of America, Merrill Lynch, Wells Fargo. The day job taught me how to see risk where most people don't, and how to underwrite a decision before betting capital on it. The real estate work, slowly at first, taught me what I actually wanted to spend my career doing.

For seventeen years I worked at the intersection of those two worlds: a corporate operator by day, a real estate investor by night and weekend. I learned what scale looks like inside the most rigorous organizations on earth. I also learned what bored me, and what didn't.

In 2019, I made the pivot fully into hospitality real estate. The thesis was simple: short-term rentals were no longer a hobby — they were becoming an institutional asset class, and the operators who treated them with the discipline of institutional investors would be the ones who won. Most operators didn't, and most still don't. That gap is the opportunity.

What I actually do

Today I own and operate a portfolio of premium short-term rental properties across North and South Carolina, including the flagship Hemingway Estates in Banner Elk, NC — a property I bought tired and dated, and have grown from $275,000 in annual revenue to a projected $415,000 over two years. The work isn't passive, and it isn't pretty. It's a relentless commitment to excellence over average.

I run three brands, each playing a distinct role:

Pacilio Capital is the investment vehicle. We acquire and reposition hospitality real estate assets — primarily short-term rentals today, expanding toward boutique hotels and resort properties as the firm scales. Capital comes from accredited investors and family office relationships, deal by deal, with a clear path toward a fund structure over time.

Blue Pineapple Rental Group is the operating company — the team that actually runs the properties day to day. It's how I hold operational excellence as the moat. Big-box property managers can't match what we do, because they're optimizing for scale; we're optimizing for outcomes.

Short Term Dojo is the coaching and mastermind program. A small group of serious operators, working directly with me to build top-performing properties and operations. Selective on purpose. Application-based. Not a course.

What I believe

I believe the short-term rental industry has bifurcated. The bottom 80% — operators with average properties, thin investment thesis, and a hope that "passive income" is still a thing — are getting destroyed. The top 20%, the operators willing to deploy real capital, energy, and obsession into building distinctive assets, are thriving. There is no middle ground anymore.

"I only play to win. Not just compete."

I believe operators who own equity, run their own assets, and write checks alongside their investors will outperform pure managers who don't. I've spent twenty years watching that play out across every cycle. It will play out again here.

I believe in honesty over hype. The hospitality real estate space is full of gurus selling fairy tales to people who can't actually do the work. I'm not interested in that audience, and they're not interested in me. I write for the operators and investors who want the truth — even when it's harder than the pitch.

What I'm working on

Right now, the focus is twofold: continuing to grow Pacilio Capital toward institutional scale, and building this writing platform as the place I share what I'm learning along the way. The essays here are a real-time record of how I think about hospitality real estate — what works, what doesn't, and what's coming next.

If any of that resonates, there are three doors: read the writing, work with me directly, or invest alongside. Whichever fits — I'm glad you're here.

— Jonathan