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The #1 Reason Small STR Hosts Struggle to Grow | Blendi Muriqi & Mike O'Connell

If you’ve ever stayed up chasing a signature before check-in—or worse, bounced between five apps just to welcome one guest—you’re not alone.

In this episode of Sip & Scale, I sat down with Michael O’Connell, founder of Happy Guest, to talk about the real headaches behind guest management—and how short-term rental hosts can stop doing everything manually and actually scale their operations without burning out.

We go deep into what a seamless guest experience actually looks like (spoiler: it’s not just clean towels), how small hosts can finally start upselling like hotels, and why building with…

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