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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 hospitality in mind will always beat chasing trends.
If you’re a host, property manager, or just curious how smart tech can transform customer experience, this one’s for you.
What You’ll Learn:
👉 Why managing guests shouldn’t feel like babysitting
👉 How STR hosts can automate check-ins, house rules, and upsells
👉 The difference between good UX and good hospitality
👉 Why Happy Guest is focusing on trust and frictionless experiences
👉 How to scale without relying on VC money
👉 The hidden revenue opportunities most hosts miss
Watch/listen now!
Stay tuned for more episodes!
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