The short-term vacation rental market hit $134.51 billion in 2024. By 2026, it will redefine how high-net-worth investors think about capital deployment. I’m watching the binary choice die in real time. For decades, affluent investors faced a false trade-off: buy a vacation property that bleeds cash or invest in real estate you never touch. Traditional […]
I’ve watched too many property owners sign management agreements based on slick presentations and impressive websites, only to realize six months later that their investment is bleeding money through hidden fees and misaligned priorities. The difference between properties that cash flow consistently and those that become financial headaches comes down to asking the right questions […]
A presidential tweet could move the market five points in minutes. One tariff announcement in April sent shockwaves through portfolios across the country. Meanwhile, the beachfront property I own in Costa Rica? Still there. Still appreciating. Still generating income. Land doesn’t care about tweets. The Volatility Problem Nobody Talks About Here’s what keeps me up at night […]
You can own a beautiful $3M home in Detroit. It won’t make you money. Meanwhile, a $1.5M property on a Maui beach will have guests fighting to book it. The difference? Most investors buy vacation homes they’d want to live in. I buy homes that groups want to vacation in. That distinction changes everything. Location […]
Big bold promises are the first thing that makes me suspicious. When I’m reviewing a Private Placement Memorandum for a real estate syndication, unrealistic IRR projections in markets that historically don’t produce those numbers tell me everything I need to know about the operator. You see a lot of people who talk about deals but […]
I see a future where the best travel experiences require reservations 12–18 months in advance. Not because they’re expensive. Because AI made them discoverable. AI tourism technology is projected to reach a market value of $1.2 billion by 2026. Everyone focuses on the convenience angle. I’m watching something different emerge. How I Predict AI Will Create […]