The Hotel Investor Playbook How to Replace a Six-Figure Job with Boutique Hotel Investing | Tim Ensmann E55
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Oct 28, 2025 Tim Ensmann, founder of Boutique Hotel Fund, left a lucrative tech sales career to build a multi-million-dollar portfolio of boutique hotels. He shares pivotal moments that led to his transition and how he used short-term rentals as a stepping stone. Tim reveals valuable insights on identifying the right first project, the financial markers to consider before quitting, and the unexpected success from group bookings that skyrocketed revenue. He also emphasizes the importance of education, strategic partnerships, and hands-on involvement in the renovation process.
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Leaving A Six-Figure Job To Protect Investors
- Tim Ensmann left his high-tech W-2 after getting a hotel asset under contract and needing full focus.
- He transitioned gradually, using short-term rental management (Second Home Stays) as a revenue bridge and safety net.
Use Short-Term Rentals As A Bridge
- Use short-term rentals to gain control over cashflow and tax advantages before quitting a W-2.
- Partner or manage rentals for others to gain experience without fully funding acquisitions yourself.
Hotels Buy Operational Freedom
- A large dispersed short-term rental portfolio can become a full-time job without operational scale.
- Boutique hotels enable scale by consolidating amenities and supporting dedicated permanent roles.