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The Short-Term Shop

Mastering the Art of Wholesaling Real Estate with Jamil Damji

Mastering the Art of Wholesaling Real Estate with Jamil Damji

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Mastering the Art of Wholesaling Real Estate with Jamil Damji

In this interview, real estate expert Jamil Damji shares his incredible journey from self-taught wholesaler to industry leader. With over 20 years of experience, Jamil talks about how he approaches the business differently, his first deal in Calgary, and the importance of ethics in the real estate world. Whether you’re a seasoned investor or just starting out, Jamil’s insights on connecting with agents, sellers, and flippers will give you a fresh perspective on how to succeed in wholesaling while maintaining integrity.

Avery: Super excited to interview you today, Jamil! To start things off, could you tell us a little bit about yourself?
 
Jamil: Well, thanks, Avery! I imagine most of your listeners are probably aware of me. I’ve been around for a while, online and even on TV. But yeah, let me share a bit about myself. I’m a real estate wholesaler, and I’ve been in the business for over 20 years now. I’m self-taught, so it wasn’t always easy.
 

Avery: Wow, 20 years! That’s impressive. Self-taught, you say? What was that journey like for you?

Jamil: Honestly, I wish I had a bit of help starting out, but I had to figure things out myself. I had my own ideas on how to operate the wholesale business model, and it pushed me to innovate.

Avery: That’s really cool. So, would you say your approach to wholesaling is different from the traditional way most people are taught?

Jamil: Absolutely. I think that’s what sets me apart. I approach things a bit differently than the typical wholesaler. You know, when I first started, my very first deal was in Calgary, Alberta, Canada. Even though I was born in the U.S., I grew up in Canada. That background shaped a lot of how I operate today.

Avery: That’s quite the journey! Tell me more about that first deal. What was it like?

Jamil: So, there was this rental house that hadn’t been sold, or actually, it hadn’t even been rented for a few months. I had overheard a conversation between some builders. They were talking about needing a property like that so they could bulldoze it and build a luxury duplex.

Avery: Interesting! So, what did you do next?

Jamil: Well, I called the homeowner directly and asked if they’d be interested in selling it instead of renting, since they hadn’t had any luck with that. Surprisingly, they were very clear—they were ready to sell. The homeowner said she’d take $350,000 for the house.

Avery: Wow, and how did you make that work?

Jamil: I immediately went to my developer friends and asked them what they’d pay for it. They said $400,000! So now I’ve got this $50,000 problem to solve, because I don’t have the $350,000 to make this deal happen.

Avery: So what did you do?

Jamil: Well, first, I tried what most people would think of—I went to family. I asked if anyone could lend me the money, telling them it would just be for a matter of weeks.

Jamil: Yeah, I had one of those agents once, and I didn’t even realize it until we were deep into negotiating the inspection. I was like, “Whoa, wait a minute,” and I ended up terminating the deal because I got so uncomfortable with being in a state that I wasn’t licensed in.

Avery: That must have been a tough decision!

Jamil: It was, but I just knew it was going to end up being a bad situation if I went forward with it. I think it’s really important, whether you’re a wholesaler, agent, or whatever, to bring ethics back to the forefront. We need to ensure we’re helping clients, not using the old-school, car-salesman-type approach.

Avery: Absolutely. So, what would you say are your core principles when it comes to wholesaling and working with others in the industry?

Jamil: For me, it’s all about connecting with the right people—being that go-to person for agents, sellers, or even fix-and-flippers. You need to establish trust and be reliable, and that’s where ethics really come into play.

Avery Carl

Avery Carl

Avery Carl was named one of Wall Street Journal’s Top 100 and Newsweek’s Top 500 agents in 2020. She and her team at The Short Term Shop focus exclusively on Vacation Rental and Short Term Rental Clients, having closed well over 1 billion dollars in real estate sales. Avery has sold over $300 million in Short Term/Vacation Rentals since 2017. An investor herself, with a portfolio of over 100 Doors, Avery specializes in connecting investors with short term rentals with the highest ROI potential, and then training them to manage their short term rental from their smart phone from anywhere in the world.

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