Commercial Real Estate Mastermind With Cherif

In this October 2025 Commercial DealPRO Mastermind call, Cherif Medawar answers real investor questions on some of the most profitable — and misunderstood — strategies in today's real estate market.

This session dives deep into:

✔️ Airbnb & Short-Term Rentals Near National Parks

– Visitor trends, seasonality, saturation, and STR regulations – How to choose the right markets (2–5M+ visitors, multi-day stays, ADR metrics) – Whether Airbnb, furnished rentals, or room-by-room is the better strategy today

✔️ Automotive Properties & Re-Tenanting

– Converting auto-use buildings – How national tenants negotiate (and when they pay premiums) – Real examples of lease-ups with Starbucks, Jiffy Lube, and more

✔️ Multi-Family Strategy: Physical vs Economic Occupancy

– Why lowering rents & standards leads to turnover chaos – How to stabilize a 50%-vacant building the right way – The formula Cherif uses to maximize value instead of chasing occupancy

✔️ Condo Conversions Explained Step-by-Step

– When the strategy works – Legal process, land-use attorneys, utilities, HOA setup, timelines – Real deals Cherif completed that created millions in profit

✔️ Leadership, Management & Team Performance

– The 4 reasons people don't perform (and how to fix each one) – How to create a high-trust, high-productivity work environment – The FACTS framework for culture (Friendly, Accurate, Complete, Timely, Strategic)

✔️ The 4 Income Types & How Wealth Is Actually Built

– Earned, business, investment, and passive income – How to transition from working for money → to money working for you – How Cherif structures debt funds, JV deals, and long-term wealth vehicles

Plus: Cherif reveals his personal "superpower": the formula mindset — a repeatable system for analyzing deals, truth, people, and markets so you can make smarter decisions faster.

This mastermind replay is packed with strategic insights, real-world examples, and powerful frameworks you can apply immediately to your investing, operations, and leadership.

Ready to scale your real estate business? Join Cherif's next live Commercial DealPRO Mastermind and get your questions answered in real time. 👉 Register here: https://www.cherifmedawar.com/cre-dealpro

#CommercialRealEstate #RealEstateInvesting #CREInvesting #RealEstateMastermind #RealEstateEducation #PassiveIncome #RealEstateStrategy #RealEstateFunds #CapitalRaising #ShortTermRentals #ApartmentInvesting #MultiFamilyInvesting #CondoConversion #AirbnbInvesting #JVPartnerships #WealthBuilding #FinancialFreedom #InvestingTips #EntrepreneurMindset #BusinessLeadership

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this episode, Cherif Medawar dives deep into real estate deal structuring and investor strategies every savvy operator needs to know.

You'll learn:

• How to protect yourself when sellers want to stay after closing (leasebacks & holdover clauses).

• Why long-term leases with corporate tenants are powerful—and how to negotiate them.

• Smart due diligence steps before bidding on auction properties.

• How to structure deals with escrow holdbacks, corporate guarantees, and tenant improvements.

• The investor evolution: from doing it all yourself to delegating, de-risking, and scaling with a team.

Whether you're a JV partner, fund manager, or aspiring investor, this episode gives you actionable frameworks to minimize risk, maximize returns, and think like a pro.

👉 Subscribe for weekly insights on raising capital, structuring deals, and building wealth through real estate.

#RealEstateInvesting #CommercialRealEstate #PassiveIncome #PropertyInvesting #RealEstateDeals #RaisingCapital #RealEstateContracts #JointVenture #RealEstateFund #Syndication #CapitalRaising #InvestorTips #WealthBuilding #Leaseback #TripleNetLease #AuctionDeals #CorporateGuarantee #RiskManagement #DueDiligence #FinancialFreedom #Investing101 #BusinessStrategy #EntrepreneurMindset #SmartInvesting

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this episode, Cherif Medawar tackles real-world questions from CRE DealPRO members, sharing his insights on joint ventures, creative financing, and the latest market trends. From navigating the complexities of escrow and ground leases to understanding the impact of the new FinCENBOI regulations, Cherif provides actionable advice for real estate investors at every stage. Whether you're a seasoned investor or just getting started, this episode is packed with tips to help you close smarter deals and build lasting partnerships.

📌 Topics Covered:

• Key points to include in a JV LOI and purchase contract

• Creative ways to structure ground leases and cap rate offers

• Understanding the new FinCENBOI regulations for anonymous investing

• Tips for navigating tenant issues and lease negotiations

• The importance of market trends and using comps to guide your decisions

#CREInvesting #JointVenture #CreativeFinancing #RealEstateMastermind #RealEstateDeals #CapRate #GroundLease #FinCENBOI #PropertyAnalysis #RealEstateTips #InvestingInRealEstate #MarketTrends #RealEstatePartnerships #CommercialRealEstate #RealEstateInvesting #RealEstateGrowth

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this episode, Cherif Medawar dives into the world of creative financing and strategic deal-making, revealing how to unlock lucrative real estate opportunities. Whether you're a seasoned investor or just starting out, Cherif's insights on structuring deals, raising capital, and analyzing properties will help you make smarter, more profitable investments. Learn actionable strategies that can take your real estate game to the next level!

📌 Topics Covered:

• Creative financing techniques to close more deals

• How to analyze multifamily properties for profitability

• Key questions to ask sellers for successful negotiations

• Strategies for raising capital from family offices

• How to structure deals that add value to your portfolio

#CreativeFinancing #RealEstateInvesting #DealMaking #PropertyInvestment #RealEstateTips #CapitalRaising #MultifamilyInvesting #RealEstateStrategies #RealEstateOpportunities #CherifMedawar #InvestmentSuccess #RealEstateMasterclass #SmartInvesting #RealEstateEducation #RealEstateDeals #RealEstateCommunity

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this powerful April 26th investor Q&A session, Cherif Medawar shares hard-hitting strategies for navigating 2025's real estate market. Discover how to protect your short-term rental business from fraud, evaluate triple net lease investments, and creatively reposition vacant buildings with national tenants. Learn when co-living makes sense, how to secure debt funding, and why now is the time to set up your real estate fund.

Ideal for fund managers, syndicators, and serious investors looking for control, cash flow, and creative deal structures.

📌 Topics Covered:

• Solving fraud issues in short-term rentals (Booking.com tactics)

• Airbnb vs. Co-living: Risks, profits & management tips

• Triple Net Lease Strategies: Franchise vs. Corporate Tenants

• Cap rate expectations in California vs. Midwest markets

• Walgreens, Burger King, Dutch Bros—tenant deal evaluations

• Debt coverage ratios & funding vacant properties

• Lease structuring & tenant improvement strategies

• Hotel investing cycles (Microtel vs. Hilton/Marriott)

• JV deal contracts, backup offer positioning & broker follow-up tips

• Why 2025 is not another 2008—and how to capitalize on it

• Setting up a Reg D 506(c) fund to raise capital legally

• The difference between syndication & fund structure

• How Cherif scaled from $10M to $50M net worth with this method

#RealEstateInvesting #TripleNetLease #AirbnbTips #CoLivingStrategy #RealEstateFund #CherifMedawar #CreativeFinancing #CommercialRealEstate #PassiveIncome #RegD506c #RealEstatePodcast #DebtCoverageRatio #RealEstateDeals #InvestorEducation #WealthBuilding #RealEstateSyndication #ShortTermRentals #CREInvesting #FundManager #RealEstateTips

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this power-packed episode, Cherif Medawar answers live investor questions on BOI filings, market slowdowns, distressed property solutions, hotel conversions, co-tenancy clauses, and how to tap into municipal grants. Whether you're holding, selling, or raising capital—this episode delivers real-world strategies for today's market.

Topics Covered:

• BOI (Beneficial Ownership Information) Filings & Compliance Updates

• Navigating Holding Costs in a Slow Market

• Creative Solutions for Distressed Property Sales

• Chapter 11 Bankruptcy as a Real Estate Strategy

• Hotel Investing: Conversion, Due Diligence & STAR Reports

• How to Secure Municipal & Government Grants for Real Estate

• Co-Tenancy Clauses & Force Majeure in Commercial Leases

• Lease-to-Own & Build-to-Suit Deal Structures

• Setting Up Your Own Real Estate Fund (506(c))

• Key Metrics for Residential & Commercial Deal Evaluation

#RealEstateInvesting #CherifMedawar #CapitalRaising #DistressedProperties #BOIFiling #HotelConversion #CreativeFinancing #RealEstateFund #BuildToSuit #PassiveIncome #CommercialRealEstate #MultifamilyInvesting #RealEstateTips #InvestorEducation

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

Facebook LinkedIn Twitter Instagram Youtube

Join us for an insightful mastermind session with real estate expert Cherif Medawar as he tackles commercial real estate investing strategies, lease options, 1031 exchanges, build-to-suit opportunities, and navigating market shifts in 2025.

📌 Topics Covered: ✅ Investing in standalone retail vs. gas stations ✅ How to negotiate lowball offers without burning bridges ✅ The power of lease options vs. subject-to deals ✅ Key questions to ask when buying an office building ✅ Tax incentives: Opportunity Zones, 1031 exchanges & historic tax credits ✅ How to structure a real estate fund and protect assets ✅ Evaluating post-disaster opportunities in California ✅ The booming net lease investment market & why it matters ✅ Build-to-suit strategies for high-profile tenants

Whether you're an active investor, syndicator, or new to commercial real estate, this episode is packed with actionable strategies to help you find, finance, and close the best deals.

🚀 Tune in now and take your real estate investing to the next level!

#CommercialRealEstate #RealEstateInvesting #CRE #1031Exchange #LeaseOptions #NetLease #RealEstateFund #InvestingStrategies #BuildToSuit #PassiveIncome #OpportunityZones #TaxIncentives #RealEstateSyndication #AssetProtection #MarketTrends #CREMastermind #WealthBuilding #CashFlow #RealEstateQandA #CherifMedawar #RealEstatePodcast

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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Strategic Leasing & Subleasing for Maximum ROI | 2025 Kickoff Call

Welcome back to the podcast! In this insightful episode, we kick off 2025 with high-level discussions on structuring lease agreements, subleasing to national tenants, and maximizing investment returns through smart real estate strategies.

What You'll Learn in This Episode:

✅ How to structure a lease-to-sublease agreement with national tenants while securing an option to buy. ✅ Key due diligence timeframes to ensure you don't get stuck in a lease. ✅ Negotiating Tenant Improvement (TI) allowances to reduce upfront costs. ✅ The power of corporate guarantees and how they impact property valuation. ✅ Strategies for converting vacant bank buildings into high-value Quick Service Restaurant (QSR) locations. ✅ How lease renewal options, kick-out clauses, and holdover penalties affect your investment. ✅ Market trends: The impact of rising interest rates on multifamily, office spaces, and QSR valuations. ✅ Build-to-suit strategies and leveraging construction financing for long-term gains. ✅ The profitability of combining real estate ownership with franchise opportunities.

This episode is packed with actionable insights to help you navigate commercial real estate deals with confidence in 2025. 🎧

🔗 Subscribe and stay tuned for more expert insights!

#RealEstateInvesting #JVPartnerships #CommercialRealEstate #PassiveIncome #CREDeals #LeasingStrategies #Subleasing

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

Facebook LinkedIn Twitter Instagram Youtube

In this episode, Cherif Medawar shares his incredible journey from having just $1,500 to making $150,000 in less than four months through his first real estate deal. Learn how Cherif transitioned from working in the hotel industry to becoming a millionaire investor, and how his creative strategies, timing, and risk-taking led to exponential wealth growth.

Cherif also dives into the power of real estate funds, revealing how setting one up in 2009 skyrocketed his success. Whether you're a seasoned investor or just starting out, this episode is packed with valuable insights, including how to leverage credit lines, creative financing, and real estate funds to build long-term wealth.

🎙️Tune in to hear Cherif's personal story, the lessons he learned along the way, and how anyone can replicate his success with the right mindset, strategies, and mentorship.

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

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In this episode, we dive into some exciting real estate opportunities, including the rise of data centers driven by AI demand, practical tips for tenant negotiations, and the power of sequential thinking for successful real estate deals. Whether you're just starting or looking to refine your strategy, this episode has something for everyone. Plus, discover key insights on how to make your deals stand out in a competitive market. Don't miss out on this deep dive into smart, creative investing!

🎙️ Tune in now to elevate your real estate game! If you found value, subscribe to our podcast for more real estate wisdom straight to your feed.

Learn from America's #1 CRE Deal Maker Listen to the Most Recent CRE Mastermind Episodes

ABOUT CHERIFCherif Medawar is a renowned figure in American real estate and fund management, with a focus on commercial real estate (CRE). He is the CEO and Founder of Medawar International Group Secured Income Fund (MIGSIF), and Secured Fixed Income (SFI Fund), managing assets worth over $100 million since July 9, 2009. His diverse portfolio includes investments in various property types, notably being the largest holder of historic properties in Old San Juan, Puerto Rico, benefiting from tax exemptions.

Cherif is also the creator of the CRE DealPRO Mastermind, an educational program aimed at transforming individuals into skilled commercial real estate investors. This monthly platform allows direct engagement with Cherif, offering comprehensive insights into commercial property investment and capital raising.

---------------------------------------------------------------------------------------------------------------- Also, join us on:

Facebook LinkedIn Twitter Instagram Youtube