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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
By Steph Weber4.9
6464 ratings
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

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