Taylor sits down with Jacob — a Bay Area tech professional turned short-term rental investor — to unpack the real story behind taking a “big swing” on a remote, high-risk property… and having it pay off.

Jacob shares how growing up in San Francisco made real estate feel impossible, why a single long-distance rental accidentally sparked his investing journey, and what finally pushed him from long-term rentals into STRs.

Then it gets real: an $800K lakefront property in Northern Michigan, a massive footprint (with an indoor pool), limited comps, sky-high interest rates, and the kind of renovation logistics that make most investors freeze. Jacob walks through the stress, the surprises, the launch chaos, and the unexpected part of the business he thought would be hardest… but wasn’t.

In this episode, you’ll learn:

• Why Jacob believes long-term rentals rarely deliver “real” cash flow (and what surprises most first-time landlords)
• How he chose a Midwest market before the data was obvious
• What underwriting looks like when you don’t have clean comps — and how to build guardrails anyway
• The behind-the-scenes reality of renovating and furnishing from across the country
• The launch lessons you only learn when guests are arriving tomorrow
• Why self-managing wasn’t nearly as hard as he expected
• How one deal can change your investing path faster than you think

If you’ve been stuck in analysis paralysis, this one is a reminder that you don’t need perfect certainty — you need the right protections, a real plan, and the willingness to get in the game.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com