Commercial Real Estate Investment Outlook 2023 - US Economy Is Not Driven By Market, But By Policy
Commercial Real Estate Mastermind
Release Date: 01/18/2023
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_outlineCommercial 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_outlineCommercial 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_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...
info_outlineCommercial 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_outlineCommercial 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_outlineCommercial 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_outlineCommercial 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_outlineCommercial 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_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_outlineJaneen M., DE
1:01 pm EST
I have the property under contract! Yeah!!! I am responsible for finding the title company. They want me to select one today. With the last couple of properties, I had under contract, the broker hired the title company. This required very little input on my end.
- What do you think I should ask the title company?
- Should I expect to make some type of upfront payment?
- My EMD is in an escrow account with Keller Williams Realty Centre, but they are not a title company. Is that ok?
1:06 PM EST Cherif talks about how important insurance is
Tom T., IL
(New JV Partner)
1:10 PM EST
Up to this point, when contracting properties, I have had the Seller’s Agent provide a contract and I would request revisions as necessary. This time, the Seller’s Agents insisted that I submit a contract. Since they accepted all my terms, I did not want to be totally inflexible.
I have been looking at the contract you provide for the JV Partners, and I am confident that it is very thorough! However, it is a bit challenging for me, partially because it is much longer and in-depth than any contract I have worked with up to this point. I will need to submit a contract next asap. Should I get a lawyer?
1:11 Cherif talks about talking about “money” and how you should NOT be uncomfortable
1:12 PM EST Fernando has a question in the chat about insurance rates
Garrett T., FL
1:13 PM EST
1) Do you see another real estate downturn similar to 2008-2009 and if so how could we benefit from it?
Cherif answers with the 3 categories of people who will be affected by the market
He shows calculation.com
CHERIF TALKS ABOUT A TRAINING ON WRAP-AROUND MORTGAGES, SUBLEASE, OPTION TO BUY, ARBITRAGE
1:21 PM EST Cherif references Tiffany/Brian’s Fund (use for possible Cracking the Code promo)
1:22 PM EST Cherif talks about the Notes Business
Cherif talks about what he has been talking about. He reviews/reminds us what he discussed would happen in the market in 2023.
1:27 PM EST Solvency- you need cash flow to sustain
1:27 PM EST What is the trifecta of disaster?
1:30 PM EST Most of your problems in life come from liquor and leverage
You have to be very creative…
(When there is problem is LIQUIDITY)
1:31 PM EST Cherif compares 2009, to how and why he started a RE Fund
1:32 PM EST Residual value in your life
1:33 PM EST RECAP
1:33 PME ST Raising capital is two-fold
1:35 PM EST Garrett’s QA2- Cherif talks about the earnest money ALTERNATIVES
2)Whether someone is a JV Partner or not, do you have strategies and alternatives for EM when submitting a contract? What are alternatives to raising capital or negotiating out of putting earnest money down if the individual doesn’t have the money? This could be for any type of commercial asset.
1:38 PM EST Cherif talks about how the US economy is not driven by MARKET, but by POLICY
VOID ANALYSIS
1:41 PM EST
Anthony L., OH
I know Cherif has many years of experience in hotels. I have an opportunity to develop a Microtel hotel from the ground up with a team at Wyndham and other potential developers that I can bring in. My question is with Cherif’s experience how would a micro-tel hold up in a cyclical cycle? Or should an investor stick to higher-end brands such as Marriott or Hilton?
I would like to ask Cherif a question live to get his feedback. I would like him to give me a presentation for me to share with my Network of Investors who want to set up a Fund, like me.
- What is Cracking the Code on RE Funds vs. syndicating?
- What is the benefit of working with Cherif vs an attorney only?
- Why is the timing right to Crack the Code on RE Funds?
- Why are you helping people set up a RE Fund like you? Aren’t you creating competition?
- What is the benefit of launching a RE Fund in 2023?
- What advice do you give to new RE Fund Managers to launch in 2023?
1:42 PM EST 2 Factors to consider
1:44 PM ET Cracking the Code Presentation
1:52 PM EST WHY NOW
!:56 PM EST Oshin’s QA1
Oshin B., CA
1) Does seasonality play a role when contacting tenants as far as their response time is concerned (i.e.: Holiday Season such as the end of the year)?
Tenants Representative
2) What about the geographical location of the property and seasonality as far as weather is concerned since the majority of the tenants would want to do improvements on the property?
1:58 PM EST Oshin QA2
1:59 PM EST
Nat R., CA
- I am starting a full rehab on a duplex in Modesto. I have narrowed it down to 2 designers and 2 contractors. What factors should I consider in making my decision?
- How would you suggest I contract with each job? What advice do you have with your experience?
At 1:59 PM EST Cherif answers the question and gives his LIST OF 10 CRITERIA for working with CONTRACTORS/DESIGNERS
At 2:09 PM EST, He RECAPS it
2:09 PM EST Jay’s QA1
Jay W., Toronto
- Hi Team, interested in your Joint Venture program. We are located in Canada, wondering if your boundaries extend this far, does this business model operate the same way in Canada as it does in the U.S.? If so, are you still taking on new partners?
- (2:11 PM EST) We have a carwash business in Toronto. I would like to bring it to the US. From a business standpoint, what do you suggest? How can we break into the market? Is now a good time? What are the steps to start?
- Do you suggest development?
2:13 PM EST Miles QA1
Miles M., NC
- Would you buy a 5-unit strip mall building on seller finance or a master lease? Will I be expected to pay more if I’m buying it on seller finance terms or as a master lease option?
Master lease, find the win-win. Cherif prefers the master lease with the option to buy.
2:20 PM EST Miles QA2
- What advice do you have for a broker outreach campaign to get pocket listing/off-market properties sent to us? What are the top 3 types of commercials I should focus on? I was thinking (of storage, apartments, and strip malls)
Seller financing and wrap-around mortgages. Cherif talks about how the banks react to this strategy.
2:23 PM EST TOP 3 TYPES OF CRE properties
Cherif likes small hotels
2:25 PM EST Position storage facilities against RETAIL
2:27 PM EST QA3
- Some tenants I spoke to want to buy the building vs lease, how do you approach that? How much would you charge the tenant? Do you have a sample agreement?
2:31 PM EST Miles QA4
- I’ve noticed in my area that tenants tear the whole building down to add new building concepts instead of doing a renovation. ex: a Vacant Payless with a bigger sq. ft and lot was torn down and turned into a Dunkin Donut. So, does it really matter if the building is bigger or it is a 2nd gen restaurant if some tenants are more interested in the lot size vs building size?
2:34 PM EST Miles QA5
- I’m a broker, how can I take advantage of using my license when buying CRE buildings for myself? How can I get paid multiple times in one transaction? (get paid a wholesale fee and broker commission (purchase & tenant fee)
2:35 PM EST Jean’s QA 1
2:37 PM EST Jean’s QA2
JeanL., FL
- I own multiple properties in an LLC. Can I put a lien on the LLC to strip the equity? I already have your KMAGB set up. I own most properties in my name, but these are new in an LLC. Please advise.
- Also, what makes your asset protection different than setting up a Family Trust?
2:41 PM EST Todd’s QA1
Todd M., CT
(Can’t make the call)
I have a property management company. My team is managing 200 doors. There is a lot of stress right now on all fronts. Do you have advice to energize the team and motivate them going into the New Year? I am going to expect them to give a little more and I don’t have much to offer as an incentive money-wise.
How should I kick off the New Year before they take off for Christmas?
2:49 PM EST Cherif talks about the best structures for people investing in DUPLEX
2:56 PM EST Todd asks about the motivation for his team and Cherif goes into a great case study and feedback with emotion
CHERIFISMS: Connect your plan to the execution of 2023 and create a climate….
There’s nothing like having a purpose…