Developments vs. Flipping: What’s the Best Approach in Today’s Market?
Commercial Real Estate Mastermind
Release Date: 09/26/2024
How to Analyze Markets, Build Teams & Convert Apartments — Full Mastermind Session
Commercial Real Estate Mastermind
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...
info_outline
Protecting Yourself in Contracts & Scaling with Less Stress
Commercial Real Estate Mastermind
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...
info_outline
JV Secrets, Creative Deals & Market Insights: A Real Estate Mastermind with Cherif Medawar
Commercial Real Estate Mastermind
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...
info_outline
What Sellers Won’t Tell You: Key Questions to Ask Before You Buy
Commercial Real Estate Mastermind
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...
info_outline
Creative CRE Deals, Tenant Strategies & Fund Setup Explained
Commercial Real Estate Mastermind
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...
info_outline
Hotel Conversions Creative Deals and Holding Cost Relief
Commercial Real Estate Mastermind
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:...
info_outline
Smart Investing: Lease Options, 7-Eleven Expansion, and Commercial Property Strategies
Commercial Real Estate Mastermind
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...
info_outline
The 2025 Real Estate Playbook: Strategies for Success in a Changing Market
Commercial Real Estate Mastermind
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...
info_outline
How I Made $150,000 in Just 4 Months?
Commercial Real Estate Mastermind
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...
info_outline
Creative Real Estate Strategies: Unlocking Opportunities with Data Centers, Tenant Negotiations, and Sequential Thinking
Commercial Real Estate Mastermind
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...
info_outlineIn today’s episode, we’re diving deep into some of the most powerful strategies in real estate investing. First, we tackle an important question—are land leases worth it? Spoiler alert: not in my book! I break down why owning both the land and the building is crucial for long-term success and how avoiding land leases can save you future headaches. We’ll also explore the lucrative world of lease options, revealing how you can make money in three different ways on just one deal! From controlling properties with minimal upfront investment to flipping them for maximum profit, I walk you through the strategies step-by-step.
But that’s not all—protecting your assets is just as important as growing them. That’s why we’ll discuss how setting up a Wyoming LLC can help strip equity from your properties and shield your investments from potential lawsuits. I explain how this structure can provide bulletproof asset protection and why it’s one of the most effective ways to safeguard your wealth.
Whether you’re a seasoned real estate investor or just starting out, this episode is packed with actionable insights that will help you navigate joint ventures, secure single-tenant properties, and protect your financial future. Plus, I’ll share tips on how to find the best deals, line up tenants, and maximize your profits in today’s market.
Ready to make smarter real estate moves and secure your wealth? Tune in now and learn how to elevate your real estate strategy! Don’t forget to subscribe to the podcast for more expert tips and tricks, and leave a review to let us know how we’re doing. Your journey to financial freedom starts here!
ABOUT CHERIF
Cherif 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: