

Commercial Real Estate DealPRO Mastermind #21
July 14th, 2025
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.
Brian B., AZ (JV Partner)
- Cherif-I hope you’re doing good. I’m thinking of putting a land parcel in escrow to then find a ground lease tenant and then hoping to JV with you. Any key points you would like to see in LOI and/or purchase contract? Escrow period in days? Ability to extend escrow? Owner is willing to provide.
San G., GA
I am considering the equity stripping structure. However, I had a question, with the new FinCENBOI, can we still truly maintain anonymous status. Id appreciate your insight as I weigh the package to sign up for. I want to stay anonymous as I own 5 rental properties and feel at risk from lawsuits. What are my options.
Edwin R.,
1- When under contract and having a strong lead but the tenant is having issues making the numbers make sense, can the numbers be adjusted? You have mentioned before that we may under certain circumstances offer up to an 8 cap on a purchase price. What would be the criteria to make an 8 cap offer? Can this be done on a Ground Lease as well or is it more likely a building that is fairly new and needs less work. I understand that maybe a longer term lease may be in play if we go this route.
2-I haven’t been able to grasp a cost to build in today’s market and what I do come across are such vague numbers. Some models say the cost may be between $300- $800 per sf. What is a good way to find a closer number to reverse engineer and get an approximate cost that I can use for comp data?
Ray S., TX
- What is the sandwich lease compared to the sublease?
- What are easy ways to make money in CRE without owning the building.
- How does Discount Roth Conversion Strategy work for those investing in real estate syndications and private companies?
Edgar A., FL (RE Fund Manager)
I was contacted this past Monday directly by the Managing Director of a $24b company and scheduled for a video call this Monday 16. On the call will be the Managing Director, Regional Head of Logistics and Services, Head of Airfreight Latin America and CAC Head of Admin & EA.
What should I expect from this call?
Should I ask for an NDA/NCA prior to the call as I have four property owners under an agreement or keep the information brief and request NDA/NCA on a follow up meeting?
Peter L., Santa Clarita, CA
I have a small portfolio of rentals I have had tenant issues with. I decided last month it’s time to sell and move on with my life instead of managing the stress and fighting with the City. CA has become impossible to work with for residential rentals.
- Would you suggest selling as a package or individually?
- Do you believe in Seasonality Effects? Should I list now or at the beginning of the year?
- Should I list with a Broker or on my own? What are the pros and cons in your experience?
- What do I need to disclose to a potential buyer as it relates to the non payments, maintenance and ongoing nightmares in the eviction process?
- Are their any pros that a NEW BUYER gets or power to get these people out?
Clearly there’s a flurry of activity happening to get deals done before year-end, but is that being driven primarily by the sellers, or the buyers? I can think of arguments for both. But I want to make sure now is the time to get out and make the most money.
What creative structures can a promote when I go to market in QT4 or QT1 2026?
I will not be on the call because I have to work on a unit that was destroyed by a tenant I can’t even evict. I have to eat it, leave my ego at the door, and fix what they destroyed while they sit and watch tv. Please pray for me.
Thuc D., GA
(New JV & CRE DealPRO)
- I see a lot of commercial Lot land that is listed around my area. One just have a new development of an Autozone that just started 2 months ago and it’s almost complete. The other lot is available for sale right across from the autozone. There’s a lot of new house building up in the area of 1 mile radius from the Autozone and the lot that’s for sale. Should we get this land then offer a build to suit? or just don’t let this distract me and focus on vacant commercial building only?
Macy J., NY
- I am in a syndication for an apartment in NV. It’s 6% with an equity position when complete and flipped. What are the signs I should look for that the deal is going to go off the rails? I’ve been reading on rents declining. Do you have an opinion on this? It was a 3 year commitment. We are about 2.5 years in. Should I exit? What can I do?
Cherif, I found this article. https://www.redfin.com/news/rental-tracker-may-2025/
- What will happen if Trump takes Fannie Mae and Freddy Mac public? How will that effect investors and home buyers?
- Do you suggest investing outside the US. Seems like there are some good development portfolios looking exciting in Mexico and Costa Rico. Thoughts?
- As a passive investor what safe but exciting opportunities should I be looking out for today?
Cherif, I found this video: https://www.cnbc.com/video/2025/05/30/were-seeing-a-bifurcation-of-commercial-real-estate-says-fortress-investment-group-vice-chairman.html
Michael R., NY
- You’ve always looked at existing buildings. What feedback or pitfalls should I watch for in developing flex space and storage in TX?
- I met you in San Diego in the early 2000s. I took a class at the Sheraton.
It was great to find you again on my linked in page.
I am running into many issues with my deals lately. Brokers are not returning my calls. Sellers are reneging on terms we agreed upon over the past 3 months. I had to suit a partner. What advice do you have to share? I have been at this for 13 years and I’m starting to feel it’s time to go back to my J.O.B. This is a uncertain cycle that I’m not sure I can recover from. I’m getting old to keep starting over.
Looking for a little Cherif wisdom here.
(Cherif, you talked a lot about your philosophies that save you from yourself. Maybe talk about that.)
FINAL TOPIC IN CLOSING:
Cherif, I thought you could conclude with talking about your daughter graduating and the knowledge bombs you have been sharing with your kids as they start new chapters in life.
Why do you play the game?
SO you can win.
You can’t win if you don’t play.