Cherif Medawar

Commercial Real Estate DealPRO Mastermind #24

October 11th, 2025

In this DealPRO Mastermind, Cherif tackles investor questions on Airbnb near national parks, converting automotive properties, managing occupancy in multifamily, and the basics of condo conversions. He also shares insights on leadership, creating a positive work culture, the four reasons people don’t perform, and the key financial principles every investor must master. Cherif ends with practical advice on mindset, networking, and preparing for the challenges ahead.

Lynel O., NM and NV 

I have been reading how national parks are drawing a surge of investor interest, but not all are created equal. It seems like some of these markets are overrun with rentals and red tape, while others offer low costs, light restrictions, and steady visitor demand. What key factors should I consider for factors if I decide to buy a few studios or small houses for Airbnb? Do you feel Airbnb or rent-by-room are a good strategies now or would you go for leases?

Kres, Toronto 

How common is it for a vacant automotive use property to be converted to a different use? Or would it be better to search for another automotive national tenant?

Michelle, FL 

I am new to multi units. I am working with an operator to learn the ropes. Their philosophy is on optimizing economic occupancy. He lowered rents and tenant standards to maximize physical occupancy. What challenges do you see with this strategy? I am starting to see turnover. I’m close to closing on a 50% vacant 40 unit community.  

Do you think I should go the route of filling the units quickly? Please advise. 

I also watched a few of your clips on condo conversion. Can you walk me through that general process? I’m in Denton County outside Dallas.

Gabriel., TX 

  1. Can you talk about how we can generate a positive working environment among our staff and trust with managers? I have a property management business and a brokerage in Rochester, NY and TX. More and more my staff is getting frustrated with a few negative team members. I need guidance. 
  2. What is your superpower and why? 

Eddie R., CA 

What are the best and the worst words in business? And how do you work that into your daily business goals and long-term?  Profit & Debt 

Tom T., IL 

(New RE Fund Manager) 

  1. What are the 4 ways to make money?
  1. When you speak of the “language of Business vs Money” please explain.

CHERIF’s FINAL TOPIC IN CLOSING:  

People analyze life inaccurately. 

Are you prepared for a catastrophe? 

What is the most important aspect of communication?  Respect There are 2 types of people: Those who focus on their goals, and those who focus on their obstacles. Focus on both and keep working incrementally to overcome whatever is in the way to your success. It is important that as you head into next year, you choose your network of people very carefully. This will be the most crucial part of your success. Make the changes that are necessary even if it is painful to regain control and then start growing again and contributing more. But don’t forget to take a vacation every now and then to regain your sanity, your energy and your enthusiasm about the potential of whatever you are doing. 

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