EP 222: Short-Term Rental Investing: What I'd Do Differently Now

If I were starting over in short-term rentals today, I wouldn't rush into the first deal just to say I owned one — and I definitely wouldn't invest where everyone else is telling you to. In this episode, I'm walking you through our real journey: buying our first STR, building a six-figure co-hosting business, and realizing pretty quickly what wasn't the right long-term play for us. We talk about market selection, cash flow vs. equity, why I'd avoid certain oversaturated markets now, and what I wish I had understood sooner about renovations, contracts, and boundaries. If you're in the "should we buy?" or "what's our next move?" phase — or you're thinking bigger than single-family STRs — this episode will help you slow down and make smarter, more intentional decisions. We cover: The investing choices I'd change if I started over Why market selection matters more than ever Cash flow vs. long-term equity (and how I think about it now) What co-hosting actually looks like behind the scenes Why we're focused on micro resorts and boutique hotels moving forward Connect with me: 📸 @theweberco 🌐 theweberco.com