Escaping the "Messy Middle" of Investing w/ DeAnna Lee episode artwork

EPISODE · Feb 10, 2026 · 31 MIN

Escaping the "Messy Middle" of Investing w/ DeAnna Lee

from The Real Estate Woman

Did you build a business, or did you just buy yourself a 2 AM job? Today, we breakdown how to stop working for your properties and start building a portfolio that offers true freedom.   DeAnna Lee is the founder of Collective Destinations and a real estate entrepreneur with 20+ years of experience. Her portfolio spans 11 luxury lifestyle properties across 7 countries, ranging from lake houses to boutique hotels to a glamping retreat in Southern Utah. She teaches investors how to escape the "messy middle" and build real freedom through experiential hospitality.   04:10 The "Golden Pause" That Changes Everything 07:37 Business Owner vs. Self-Employed (The Kiyosaki Test) 12:08 Time Traveling: Buying at the "End of the Path of Progress" 14:46 Why Smart Money is Moving to Boutique Hotels 20:18 Surviving the "Holidays in Hospitality" 29:41 The "Golden Triangle" Glamping Project in Utah 🔗 Connect with Us: Monter Coaching: montercoaching.comFollow Debbie: @montercoaching Website: collectivedestinations.com Instagram: @collective.destinations Want to scale your business? https://montercoaching.com/contact/ Want more insights like this? Don't miss an episode. https://montercoaching.com/real-estate-leadership-podcast/

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Escaping the "Messy Middle" of Investing w/ DeAnna Lee

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