Ever find yourself spending hours on work you know someone else could do—yet you still do it anyway? I’ve been there, and so has my guest, Ben Coleman.
In this episode of Sip & Scale, Ben opens up about how he went from doing everything himself—marketing, guest messaging, operations—to finally realizing that delegation wasn’t optional if he wanted to grow. We dig into how he built a system that allowed him to step out of the weeds, how hiring offshore talent completely transformed his workflow, and why trusting your team (especially your VAs) is the key to long-term success.
We also dive into the realities of running a short-term rental business in today’s market—automation, guest experience, burnout, and why most property managers underestimate the real cost of “doing it all.”
Whether you’re a property manager, entrepreneur, or just tired of feeling like your business runs you, this episode will help you rethink what “letting go” actually looks like.
What You’ll Learn:
👉 Why doing everything yourself is the fastest way to stall your business growth
👉 How to delegate with confidence (and stop micromanaging)
👉 The real ROI of hiring virtual assistants for your STR business
👉 How to use automation and offshore talent to scale sustainably
👉 Why trusting your team gives you more time to focus on strategy
👉 The mindset shift that separates hustlers from true business owners
Tune in now and learn how to stop working harder and start scaling smarter.
Follow Ben and check out his work here:
💻 Happy Guest: https://www.happyguestofficial.com/
📊 Rev and Research: https://www.revandresearch.com/
🔗 LinkedIn: https://www.linkedin.com/in/benjamin-coleman-6256b156/
📸 Instagram: https://www.instagram.com/professorbencoleman/

Stay tuned for more episodes!
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