May 18, 2026

From 20 Airbnbs to Boutique Resorts w/ Tim Ensmann

From 20 Airbnbs to Boutique Resorts w/ Tim Ensmann
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Tim Ensmann went from scaling 20+ Airbnbs to developing experiential boutique resorts across the U.S. In this episode, he breaks down how he transitioned from short-term rentals into boutique hotels, raised capital for multiple resort projects, and turned undervalued mom-and-pop properties into multi-million dollar hospitality assets.

We cover:

  • Why bigger deals are often easier than small ones
  • Turning a $1.5M property into a $4.7M resort
  • The future of boutique hospitality
  • Raising capital and structuring hotel deals
  • Why experiences outperform commodity real estate
  • How strategic partnerships accelerate growth
  • Lifestyle-first entrepreneurship and long-term wealth building

Curious as to how we’ve bought multiple businesses and built millions in equity?

Give this video a watch for a full breakdown:
https://www.youtube.com/watch?v=cviipnGtDWI&feature=youtu.be

If you are serious about building a life on your terms and want to surround yourself with people who are actually doing it, go to:
https://actionacademy.com?el=action_academy_podcast

If you want to leave corporate America in the next 6-18 months - you should check out our Action Academy Community 👔🏝️ with over $500M in deals done across small businesses and commercial real estate, and over 600 members - we help you SCALE to your freedom. Schedule A Free 40 Minute Coaching Call With Our Team Here To Get "Unstuck" and Learn More.

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IG @brianluebben
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