How To Diversify Your Commercial Real Estate Portfolio In This Economy - Creative Strategies
Commercial Real Estate Mastermind
Release Date: 12/29/2022
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...
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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...
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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...
info_outlineCommercial 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...
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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...
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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:...
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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...
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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...
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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_outlineCommercial 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_outline* Discussion Topics And Questions:
* Sara M., NC
- How would you suggest an investor diversify their portfolio for this economy? I have 2 rentals and one small piece of property, but I do not know if I should sell and get into something new. What are your thoughts?
- How can I increase my credit score?
* Leza B., CA
- I would like to know some dos and don’ts for purchasing commercial deals.
- Do you think banks will loan on commercial deals right now?
* Alan C., CO
- Has Cherif or anyone used the First Right of Refusal Contract to hold a property instead of a full Buy/Sell Purchase Agreement while Smiling and Dialing hunting for a National tenant?
- Zero to very little Earnest Money
- No proof of funds required
- We are more up-front with Brokers and Sellers
- Less commitment, less risk
- Much easier to obtain
- I was thinking of running an ad in Franchise Magazine. (Assuming the ad is effective, it increases my funnel dramatically) Thoughts? Any downsides that I’m not aware of?
* Matt G., FL
Can you give us general information on a few CREATIVE strategies to BUY residential deals in this market? No money-down ideas to get us started.
* Oshin B., CA
I am part of the JV and have been looking for properties in CA. Unfortunately, I have not come across any newer buildings. Everything is very old. Some of them have been remodeled or retrofitted as far back as 20 years. Will This work?
What about a building that is attached to another building but has its own individual deed?
I found a location in a downtown area, and it was originally built 120 years ago and titled as a historical building. However, the interior is built with a nice red brick, and the flooring is hardwood; located next to a lot that is covered with grass (what looks like a pet park) and across to the property, a 140-space parking lot is being built will finish by the end of this year. This building is one block away from the city hall and transit station. A couple of national tenants are located 1-1.7 miles away. However, there are local food businesses, ice cream, and coffee shops on this street within the next 2 blocks. 1) I would like to know your opinion about this type of property located in these locations. 2) Can we bring a national tenant that is not a QSR so doesn’t require a grease trap and kitchen (i.e., Dunkin Donut, Coffee Bean, and such tenants)?
In case of sale/leaseback, since we are becoming the building owner, do we have the power of setting the lease terms, or the listing broker will have the leasing terms as part of the sale price/package?
* Jeff K., CA
(NEW to CRE DealPRO but is a Broker and can’t be here on the call)
I broker land and want to start a Fund for Renewable Energy in CA, AZ, TX, and OR. Do you suggest a debt fund?
* Bill B., NM
- When managing apartments with 50+ units, what advice can you give on managing the Property Managers OR managing the property myself?
- Do you think you will bring back GBA for tax incentives in the future?
* Chad T., NY
- What are the pros/cons of Family Trusts, LLCs, and your structure for stripping equity?
- How can I protect my cash and trading account if I have the structure with you? Is that a UCC1?
- Did your kids start school? Are they happy to be back in the books? How do you manage all your deals and family life?
* Tamara C., FL
I see that you usually only invest in the US- why not internationally? Do you feel the legal side is too difficult to manage? Why are you so set on this?
* Jordan., IL
What are the biggest challenges you run into as a commercial real estate portfolio holder? Is it with the tenants, the buildings, or the people involved?
How can I explain to a broker that the “refundable” EM is a win for all? The past few deals have been nonrefundable EM, and it’s killing me.
* FINAL TOPIC IN CLOSING:
Please expand on your thoughts.
The great Multiplier. How does this work, and how can you keep focused on it with many business models?
The importance of “howling.”