The Latest Episodes of INSIGHT with Chris Van Vliet
May 10, 2022

From Failed Stand-Up Comedian To Real Estate Mogul: Jamil Damji From A&E's 'Triple Digit Flip'

From Failed Stand-Up Comedian To Real Estate Mogul: Jamil Damji From A&E's 'Triple Digit Flip'

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Jamil Damji (@jdamji) is a real estate entrepreneur and one of the hosts of the A&E show "Triple Digit Flip". He sits down with Chris Van Vliet at his beach house in Marina Del Rey, CA to talk about how a failed career as a comedian led to him getting started in real estate, what someone needs to know when they are flipping their first property, what he looks for when he wholesales a property, how he started his company KeyGlee, the best advice he has ever received, his TV show "Triple Digit Flip" with his co-host Pace Morby, his advice on the current housing market and much more!


To learn more about Jamil Damji visit:


On his show “Triple Digit Flip”:

“It’s been an incredible journey for us. Four of us are the main cast members, my sister who is project manager and my best friend Pace. We run around doing life together and Pace’s wife is the real estate mogul. We run around, flip homes and make them beautiful and have a great time. Second season is in production at the moment, which is great, because not many shows get a second season.”

On the appeal of the show:

“We all live in a place, the home is a necessary place for all of us. Also, everybody has a range in respect to their design and their ideas, what makes a home a home. I think because everyone has such broad tastes and there is so much scope for business, we can make substantial profits in buying, fixing and selling homes. For the most part people just like thinking about things they can do. We can learn about anything on the internet, and if there is an opportunity to make 6 figures on house flipping, then why not? If all it takes is some courage and investment and grit, then why not?”

On how to make something from nothing:

“So when you buy a house that is distressed, you can get a pretty decent deal. If you are brand new and don’t have a lot of money to participate in the real estate market, you can do something called wholesaling. This is where you identify a good opportunity, put it under contract and then sell your position in the contract to another investor. You are literally flipping paper. That’s how I did my first deal in Canada, which they called a skip transfer. I was in a media company in the early 2000’s, where my job was cold calling, moving their advertising from the yellow pages to the internet. Businesses were reluctant because they didn’t think that the internet would stick, but haha it did! We sold the websites for $600, but they cost $700 to make, so every one was a loss! I then overheard a conversation about demolishing houses and then building duplexes, and would make $160,000 per project. They didn’t have enough to demolish, so I asked if I could find any. The next day I see a house for rent in the neighbourhood, so I called this lady and asked if she couldn’t find a renter, would she sell? She told me that for the right price she would, I asked for a price that turned out to be $350,000. I then went to my housing partners and they asked how much would they pay and they said $400,000. Most people would say ‘Oh she is willing to sell for $350,000 so just give me something.’ The way my mind worked was I need to get myself in this transaction. I started cold calling attorneys starting with a and getting through to s. This one lawyer explained to me that I need 2 contracts, one as me as the buyer and one as me as the seller. Bring both contracts back and you can be on the conveyance. After the real estate fees I made $47,000, that was my first deal.”

On trying to be a stand up comedian:

“Well it didn’t work out, which is why we are here talking about real estate and not stand up comedy [laughs]. I came to the US to do stand up comedy and got a bit of traction. I did the open mics and posted some videos on Funny or Die, they were great. So I was writing and producing but real estate just kept calling me. I was living in LA but looking at Phoenix, you could buy a condo that sold before the financial crisis for $400,000, but now it’s $25,000. It rents for $800 a month, tell me where else you can do that. I saw the opportunity, so I packed up and said that stand up is not for me anymore. I did some wholesale deals and flipped contracts, I made $17,000 in 8 minutes on Craigslist. Seeing how easy it was to spot value, I knew it was time to pack things up. It was my birthday, December 12th 2012, 12/12/12. I drove through this life threatening dust storm, made it through and here I am.”

On spotting a deal:

“So you ever see those houses that have tin foil in the windows, lawn is overgrown and the mail is piling up? Those are called zombie houses and they are all over. There is a way to contact the owner of that house and let them know that the tenant has moved out and the house is destroyed and looks like it does. You call those people and tell them about the condition and then offer to buy it. Do a cash deal and offer to handle the tennant, that is one way to find these houses. Also look at code violations, there are breadcrumbs left by the property as to there being a problem. These lists are all on public records, you can download the records, get the numbers and start calling them.”

On the future:

“One of my investment strategies, and I have a couple, for me if you have looked at the state of service, it’s not good. If you go out to eat, a lot of places are understaffed, there is a vacuum of shortages. I think also with Airbnb I think we are bullish as a world, we are all enjoying looking at other people’s species as opposed to sterile hotels. So I am looking at adding luxury spaces for people to rent. Secondly, there is an opportunity in small family homes to wholesale. I built a 6 plex, fully modelled, and the landlord had just started renting. He was renting the 2 bed and 1 bath for $1,200 a unit, rented 5 out of 6, so had 1 left over. When I negotiated, he was like ‘I’m not giving you a deal, I know who you are. I want top dollar for these, $1.2 million.’ I’m like ok I’ll take it for that. In actuality, the rent gap means that they go for $1,700, not $1,200. That last vacant unit, we rented it for $1,700 on Craigslist. We posted the lease and closed on $1.2 million, a person moved in. Now I have the rent gap of $500, times that by 5 more units available, and these people will be on a month to month contract, so you can raise rent. I made $450,000 in one transaction by raising the rent in one unit.”

On the biggest thing he has learned:

“I have realized that we are so impatient wanting to get to a destination. You can see me saying I want the car, the house and all the friendships, but they all came from pain. AT this moment in life, you are meant to be where you are. There is always an opportunity out there, but I don’t get there without the lessons or the valleys. I failed as a comedian but A & e saw something in me and let me be who I am. Nothing in life is easy, but there is God in all of the tough situations.”

On how the show came to be:

“They came and found us. We skipped the usual Hollywood b.s. Of the teaser to the pilot, then the half season and the full season. Pace’s YouTube posts a video and the casting director thinks it is hilarious. They reach out to us and A & E wanted to do a Zoom call, but I thought it was all a scam so I ignored them, you know? Nobody wants me at that time. But Pace doesn’t ignore it and we do the 30 minute Zoom call. I am looking at the names on Zoom and Googling them, and it’s all legitimate. We get an email a week later where they say they love us, so we are skipping the pilot and we got a show! Season 1 was gruelling, there was a lot of work. The show is 43 minutes long, but we shoot like 100 hours of footage.”

On advice for someone who is in a rut:

“Go inside you. Nothing that you want is outside of you, I can’t stress that enough. I have found so much peace and opportunity by just being in my own heart. If you can live where you are present in it, you know when you go on autopilot, you do that a lot each day. So a lot of us are checked out, and then nothing we do has power. But if you are in a rut, try to get as clear as possible about where you are. Take one step in being present and see the doors that open. There are doors everywhere, I have walked through some that are chance, but they are not. There is love there and opportunity.”

On what he is grateful for: 

"Breath, family and for me."