Cherif Medawar

Commercial Real Estate DealPRO Mastermind #19

April 26, 2025

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.

John M., NJ 

I’m located on the NJ NY line. I have done well over the past 7 years with Airbnb, but over the past 10 months I have lost a lot of money on cleaning, HOA issues, new City regs and now refunds on credit card scams and games. I have been reading up on this Co Living concept.  

  1. I know you have short term rentals and nightly stays in PR. Have you run into these issues? 10:02 am
  2. How did you resolve?
    3. And what do you think about Co-living rental scenarios? What type of lease terms should I consider?

https://www.biggerpockets.com/blog/the-end-of-the-airbnb-era-coliving-is-next?utm_campaign=04.22.2025%20REINewsletter&utm_medium=email&utm_source=Iterable&utm_channel=28425&utm_content=Marketing 

Daniel T, MD 

Cherif, you have talked about a period of heightened volatility and uncertainty for a few years and when we should expect it. You predicted 2025, since 2023. I see you have been correct. In some cases, we are seeing prices start to reflect that and it can create opportunities for us to invest if we have money. I set up a fund with you a few years ago and I have had success. I have money to deploy and would like to look at turnkey NNN opportunities.  

  1. What do you think I should ask the broker or current seller to make a good deal?
  1. upfront payment? 
  1. Do you feel Walgreens is a good bet? 
  1. In today’s environment what cap should I consider in CA vs Midwest. 10:16am (Cherif gives 2 extra ways to make money with STB) 
  1. What do you think about this Deal? 
  1. 500 SFRetail BuildingRedding, CA 96002$2,157,303 ($4,314.61/SF)4.45% Cap Rate 

https://www.commercialsearch.com/commercial-property/us/ca/redding/dutch-bros-coffee-long-term-abs-nnn-lease-high-visibility/ 

Cherif gives perspective on money and life. 

 

 

 

 

 

 

 

 

 

 

 

Tim T., IL 

(New JV Partner) 

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 by Wednesday.  Should I get a lawyer?

 Cherif recommends The Terrible Truth About Lawyers. He discussing thinking and action. He tells them the focus to get things done. 

Garrett T., FL 

1) Do you see another real estate downturn similar to 2008-2009 and if so how could we benefit from it? 10:42am GREAT EXPERT FEEDBACK ABOUT THE CURRENT MARKET TODAY! 

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.  

10:51am (All investing starts with… know thy self. Know your market and assess the risk. 

Edwin R., FL 

(JV Partner in Orlando) 

While making offers and sending LOIs I have been confronted with other parties making offers and sellers asking for more money as an earnest deposit or raising the price. I have declined such requests by stating the following… ” We have seen this before and respectfully rescind our offer. Should anything change please feel free to contact us and maybe we can do business in the near future” I am just wondering if this is the right response, or should I be more aggressive with my negotiations?

“You probably think I’m a jerk…”

Jake N., Toronto 

  1. I know Cherif has many years’ experiences 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 more higher end brands such as Marriott or Hilton? 
  2. I just finished the training yesterday 

Can I set this up in Canada and take money from Canadians- do they need to have a high net worth? 

What is Cracking the Code on RE Funds vs. syndicating with a template?

What is the benefit of working with Cherif vs an attorney only?

Why is the timing right to Crack the Code on a RE Funds?

Why are you helping people set up a RE Fund like you? Aren’t you creating competition?

Cooperation vs competition, exchange of value… Open your network. 

What is the benefit of launching a RE Fund in 2025 when investor fear is at a high level? 
The universe  

Laura 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 end of the year)? 

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? 

Nat R., GA 

  1. I am starting a full rehab on a 4-plex in Jacksonville . I have narrowed it down to 2 designers and 2 contractors. What factors should I consider in making my decision?  

What kills a RE deals? Time. All these delas start with an assessment of risk. CREATE INCENTIVES. 

  1. I’m subbing a lot out; do I need a contractor, or can I hire myself? 
  2. How would you suggest I contract with each job? What advise do you have with you experience? 

Jay W., Toronto 

  1. 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? 
  1. 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? 
  2. Do you suggest development? 

Miles M., NC 

  1. Would you buy a strip mall building on seller finance or master lease?  Will I be expected to pay more if I’m buying it on seller finance terms or as a master lease option?
  2. Some tenants I spoke to want to buy the building vs lease, how do you approach that? How much would you charge to the tenant? Do you have a sample agreement?  
  3. I’ve noticed in my area that tenants tear the whole building down to add new building concept instead of doing renovation. ex: a Vacant Payless with bigger sq. ft and lot was tore down and turned into a Dunkin Donut . So, does it really matter if the building is bigger or it being a 2nd gen restaurant if some tenants are more interested in the lot size vs building size? 

Todd M., CT 

(Can’t make the call) 

With so much news on TV about Policy shifts do you think these controversies create opportunity? With  new administration policies, such as tariffs, are investors likely to benefit with  real estate values over the near term? Do you have any predictions? 

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