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What if a single design change to your Airbnb could generate $400,000 in additional projected revenue? That's exactly what happened for commercial real estate investor and fund manager Cherif Medawar — after one conversation about aesthetics changed how he saw his entire portfolio.
About This Episode:
In this episode of the ROI Masterclass, Liat Siegel sits down with Cherif Medawar, commercial real estate investor, fund manager, author, educator, and the largest owner of historic properties in Old San Juan, Puerto Rico, with over 30 years of experience building, acquiring, and transforming real estate across residential, retail, mixed-use, hospitality, and commercial asset classes.
Cherif shares the defining philosophy behind his career: the money isn't in the property, it's in the structure. From his early days working at the Century Plaza Hotel in Los Angeles to becoming the right-hand man to a billionaire at just 21 years old, to building a $100M real estate fund, Cherif breaks down the exact frameworks he uses to assess risk, structure deals, and scale businesses without losing himself in the process.
Key Topics Covered:
The 6-part risk mitigation framework Cherif uses on every investment (safety, cash flow vs. cash out, liquidity, reserves, plan B/C/D, and diversification)
How a $70,000 aesthetic investment in Puerto Rico Airbnb units is projected to generate $400,000 in additional annual revenue
The three stages of wealth: working for money, working the money, and letting the money work for you
How to buy vacant single-tenant commercial buildings and convert them into cash-flowing or cash-out plays
The strategy-structure-system-automation-scale-sustainability framework for building a business you can sell or pass on
Why your guest reviews are your best punch list — and how Cherif used complaints to 10x his 14-room hotel's revenue before selling it
The Airbnb algorithm insight most operators don't know: higher-pixel cameras result in immediate higher ranking
Connect with Cherif Medawar:
🌐 cmrei.com
📺 YouTube: Search "Cherif Medawar" (3,500+ videos)
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The operators we interview every week are in this room. Come join us. Link in bio.
#RealEstateInvesting #CommercialRealEstate #AirbnbStrategy #RealEstateFund #STRoperator #BoutiqueHotel #ROI #WealthBuilding #Entrepreneurship #RealEstatePodcast #CherifMedawar #ROIMasterclassWhat if a single design change to your Airbnb could generate $400,000 in additional projected revenue? That's exactly what happened for commercial real estate investor and fund manager Cherif Medawar — after one conversation about aesthetics changed how he saw his entire portfolio.
About This Episode:
In this episode of the ROI Masterclass, Liat Siegel sits down with Cherif Medawar, commercial real estate investor, fund manager, author, educator, and the largest owner of historic properties in Old San Juan, Puerto Rico, with over 30 years of experience building, acquiring, and transforming real estate across residential, retail, mixed-use, hospitality, and commercial asset classes.
Cherif shares the defining philosophy behind his career: the money isn't in the property, it's in the structure. From his early days working at the Century Plaza Hotel in Los Angeles to becoming the right-hand man to a billionaire at just 21 years old, to building a $100M real estate fund, Cherif breaks down the exact frameworks he uses to assess risk, structure deals, and scale businesses without losing himself in the process.
Key Topics Covered:
The 6-part risk mitigation framework Cherif uses on every investment (safety, cash flow vs. cash out, liquidity, reserves, plan B/C/D, and diversification)
How a $70,000 aesthetic investment in Puerto Rico Airbnb units is projected to generate $400,000 in additional annual revenue
The three stages of wealth: working for money, working the money, and letting the money work for you
How to buy vacant single-tenant commercial buildings and convert them into cash-flowing or cash-out plays
The strategy-structure-system-automation-scale-sustainability framework for building a business you can sell or pass on
Why your guest reviews are your best punch list — and how Cherif used complaints to 10x his 14-room hotel's revenue before selling it
The Airbnb algorithm insight most operators don't know: higher-pixel cameras result in immediate higher ranking
Connect with Cherif Medawar:
🌐 cmrei.com
📺 YouTube: Search "Cherif Medawar" (3,500+ videos)
--------
The operators we interview every week are in this room. Come join us. Link in bio.
#RealEstateInvesting #CommercialRealEstate #AirbnbStrategy #RealEstateFund #STRoperator #BoutiqueHotel #ROI #WealthBuilding #Entrepreneurship #RealEstatePodcast #CherifMedawar #ROIMasterclass
