The Hotel Investor Playbook What It Really Takes to Buy Your First Hotel in 90 Days | Jacobo Hernandez E53
Oct 14, 2025
Jacobo Hernandez, founder and CEO of FreedomVest Capital, shares his bold journey of trading a $10M short-term rental portfolio for a 90-day road trip to acquire a boutique hotel. He discusses uncovering a hidden gem in Eureka Springs for just $1.2M, driven by hands-on market visits and data analysis. Jacobo outlines his unique approach to storytelling for fundraising, which raised over $2.5M. His focus on creating wellness-focused experiences highlights the importance of innovative asset strategies in the hospitality industry.
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From STR Exit To Hotel Hunt
- Jacobo sold his $10M short-term rental portfolio, learned boutique hotels via courses, and hired a remote acquisitions analyst to underwrite thousands of deals.
- He used his marketing and scaling experience to pivot from STRs to hotels and built underwriting processes before touring properties.
Disqualify Deals Fast With Simple Unit Math
- Disqualify quickly using unit economics: compare price per door to market ADR and occupancy to estimate revenue and NOI.
- Use conservative margins (e.g., 40%) and cap rates to model exit potential before visiting in person.
Touring Florida And California Deals
- Jacobo toured Florida and California extensively but found limited land and high costs prevented experiential hotel builds.
- In California he nearly contracted a Palm Springs deal that stalled over environmental and seller issues.
