Right About Now with Ryan Alford - No One Is Coming to Save You: How Jamil Damji Took Control of His Life & Built a Real Estate Empire

Episode Date: April 3, 2026

In this episode of Right About Now, Ryan Alford sits down with real estate investor and entrepreneur Jamil Damji to unpack a story that starts with rejection—and turns into full ownership of life, business, and purpose. After being denied entry into medical school despite doing everything “right,” Jamil made a decision that changed everything: no one else would control his future again. From his first wholesale deal—turning a $50K opportunity into a life-changing moment—to losing everything during the 2008 financial collapse and rebuilding from the ground up, Jamil breaks down what it really takes to create success on your own terms. The conversation goes deeper than business, touching on addiction, self-discovery, and the internal work required to evolve as a leader, father, and human. Jamil also shares how he’s now using his platform to solve real-world problems—from housing affordability to helping people experiencing homelessness build new opportunities through real estate. This is more than a business story—it’s a blueprint for taking control, making different choices, and building a life you’re proud of. 🎯 Topics Covered Why Jamil rejected the traditional path after medical school denial The first wholesale real estate deal that changed everything Lessons learned from losing everything in the 2008 financial crisis Why success is an “inside job” (mindset, habits, and identity) Addiction, recovery, and rebuilding from within Building a scalable real estate business through relationships (not cold leads) The power of personal branding and TV (Triple Digit Flip) Why real estate investors must take responsibility for housing challenges Co-living, affordability, and solving real-world housing issues  🤝 Connect with Host & Guest Ryan Alford (Host) Instagram: https://www.instagram.com/ryanalford Website: https://ryanisright.com Jamil Damji YouTube: https://www.youtube.com/@JamilDamji Instagram: https://www.instagram.com/jdamji

When you're in a survival mode, you do what you've got to do to survive. And that means you're clutching and grasping and filling holes of worthiness and filling holes in yourself with whatever you can. And even though it's temporary and even though the chemical lasts its half-life and then you got need more of it or you crash and you're on this hamster wheel of trying to maintain. Eventually you fall. You fall on your ass and you see that you've got to make a real pivot, a real change, something from the inside out. That's why I really believe success is an inside job. This is Right About Now with Ryan Alford, a radcast network production. We are the number one business show on the planet with over one million downloads a month.

Taking the BS out of business for over six years and over 400 episodes. You ready to start snapping next and cash in checks? Well, it starts right about now. Hey guys, what's up? Welcome to Right About Now. We're taking the BS out of business, baby. That's the tagline. but it's the truth. And you know what? There's no one better than my good friend. Jamil Damje. What's up, Jamil?

What's cracking, brother? Good to see you, man. Hey, man. It's good to see you. I always think TV when I see you and I talk to pace and you're best known for probably with the masses. You're best known in our circles with just being a badass real estate investor, but best known probably to the masses from triple digit flip. How's life, brother? Life is great, man. I'm really figuring out how to have this life where I get to do the things that I've been working so hard to do, which is, is continue to grow professionally, be there consistently for my family and myself. Yeah, it's a delicate balance, isn't it? It's like juggling the balls, but I respect the hell out of you for trying to get it done because that's what it's all about at the end of the day. Yeah, we all got to juggle balls, no ditty. Jamil, let's set the table for everyone.

People probably heard of A&E show, the triple digit flip. They know you're a badass real estate guy. What got you in real estate? Where does the passion and the energy come from? It exudes from you. Where'd all that jazz come from? I accidentally found myself in real estate. I'm East Indian, culturally, heritage-wise.

My family had eyes for me to be a doctor or an engineer, but doctor was where I was being groomed to have my life. I didn't get into medical school, which was at the time one of the most disappointing and heartbreaking things that ever happened to me. I had worked so hard in college to get a near 4.0 GPA. I killed the medical school interest exam. I did all the things you need to do to pat a resume with volunteering

and extracurricular activities that I didn't have time for, but did anyways because I needed it for my application and the interview process. And then some dude saw me and said, no, you know, just not today. I saw that as a sign, really, because I had done all of the things that you should do. In fact, I can say it now, but in the medical school entrance exam, the guy who sat behind me cheated off me on the test. I know him really well. He's my cousin and he had partied the night before and needed help on the exam and I let him cheat off me. He got into medical school.

What the fuck? That guy's prescribing you guys all the things and is giving you, everything you need right now to survive. He gets into medical school. I don't get in a medical school. That just showed me the disparity in this whole process. Some guy, depending on how he woke up today or who I remind him of or something about me made this guy say, no. It wasn't my testing scores because they were better than my cousins.

It wasn't my GPA. It was also better than my cousins. What about me made that person say no? When I saw that, I realized that another human being had control of my destiny. And an arbitrary decision could change the trajectory of my. my life. And I decided then never again. I was never going to let another human make my choices. I was never going to let a human being say yes or no to me. No, I'm going to pave my own path. I'm going to do it myself. And so that's where the passion came from was a general looking at life

and looking at the way the system is kind of set up and just rejecting it. It was a full rejection of what was paved out in front of me as a way to succeed. I knew I had to take control of it. Now, I find myself in an entrepreneurial situation, which wasn't really lucrative at the time. but it put me in proximity to a guy who was investing in real estate, and I got an opportunity to do my first wholesale transaction, which at the time I didn't even know existed. There was no online education. I thought I invented wholesaling because of the deal, but I hadn't.

I thought I did because I hear from these developers that they're looking for these old bungalows in Calgary, Alberta, where I grew up, that they could demolish. They just needed to have 50-foot frontage, 10-plus feet in depth. They needed to be zoned R2, and they needed to be in specific neighborhoods in the city. Now, I lived in one of those neighborhoods in a rental, and I had tried to rent one of these houses a few months earlier, but I couldn't because it was $200 out of my budget. But it was still available when I was walking my dog the next day.

And I called the for rent sign and I asked a homeowner if they would consider selling it instead of renting it because they had been unsuccessful renting the spot. Her answer was, yeah, for the right price. And I inquired what that would be. She says $350,000. And this decision that I make next is what changed everything for me. I didn't go to the people who were looking for that house and say, I can get you this house for $350, which most people would have done. I went and I asked the question, how much would you pay? And they said 400,000. So now I have a $50,000 problem to solve because I can buy it for 350. I can sell for 400. I have no money. I have no credit. I have no way of acquiring this. What do I do? I start talking to my family members. I start asking for a loan. I start seeing who could give me 350 grand for a week or two. And nobody wanted to give me any money. I'm the kid who didn't get into medical school. Why would he give him anything? Then I start calling real estate attorneys. And I get all the way through to the letter S, a guy named David Steed, answers my. call he's so fresh out of law school he had no secretary and i tell him my problem and he's like oh that's easy

that's called a skip transfer and i'm like explain he's like you take two contracts one where you're the buyer and you pay 350,000 on that contract and then you take a second contract with everything else lining up except you're now the seller on that contract and the new buyer is going to be who the buyer line is and the price is going to differ because you're buying for 350 you're selling for 400 everything else has to be the same so the conveying attorney the condition dates all of that have to line up for this to work But once you've got these things signed, bring these contracts to me. And then I asked what happens then. He said, takes me a couple of weeks to do some research, look at liens, make sure that I can

convey title, pay off on the mortgage, all of the documents have to be prepared. And once that's done, I'll have a check waiting for you. It happened. I get a $47,000 cashier check. And coming from a situation where my parents hadn't made close to that in a year in either of their lives. For me, that was the game changer. That's where the scales fell from my eyes. And I saw what is possible in life.

And I never looked back. I went ham after that and I started wholesaling full time. I do really well in it until the financial collapse in 08 where I lose everything because of leverage and just inexperience and doing too much, which is essentially how I got caught up in that. But it was a beautiful education and it taught me so much. That's where I get started. That's where the passion comes from. Because quite honestly, Ryan, I look at life as a series of choices. You see everybody gets a chance to choose something different. something that's outside of your regular patterns and your life is pregnant with these possibilities of making different choices but too many of us get stuck in patterns that are familiar and comfortable now if you continue to choose the same thing you chose yesterday then your tomorrow will look like it does today and if today looks like a job you hate a relationship that doesn't serve you and just general discontent with where you've gone then you're doing what I learned from Andrew Huberman how they treat rats who they're testing for depression it's this

theory of hopelessness at what point does a rat that you put in water stop swimming? When does he give up? And they look at that time, and then they give these rats drugs to see if they can extend how long the rat will swim. And then they say that's the drug that's going to cure depression or at least solve some symptoms. Well, what about not putting that rat in that situation? Or how about helping the rat out of that situation rather than just extending how long he'll swim? What about figuring out how to put that rat in another medium? And that's what we're doing to each other in life. We're putting ourselves and we're putting each other in these glasses of water and these tanks of water and we're like swim.

And this is like people that are in relationships that are terrible. These are people who go to their nine to five job that they hate. They work for somebody they don't admire or don't trust or wouldn't trade places with based on character. And they give up. At some point, they say life happened to me. And now I'm just going to do what I do until I have to retire. The passion comes from being able to get in front of that person, making the choice to quit, making the choice to give up and saying, hey, I know about it.

another glass. I know about another way that you can get out of this spot where you're no longer hopeless and you can maybe do something with your life that would make you proud. Damn, man, we say taking the BS out of business. That's how you take the BS out of business. That's real shit right there. They say the best and greatest growth happens in discomfort. I firmly believe that. When you didn't get into medical school, when you've been working for that, that's the expectation. You were highly uncomfortable, I would have to guess. The greatest gifts. sometimes come in these surprises and this discomfort. I joke all the time. I have balloons and clowns at my pity parties, but they only last an hour. They're one hour. You may have had a pity party for a

little while. I'm sure we all do, but you've flipped the fucking switch, dude, and you turned it into greatness. Not only going into real estate, but uncovering and unlocking the whole selling aspect and the ability to do something that a lot of people around you that didn't know how to do. That's what I call grit and resourcefulness. The two greatest attributes on earth. And you exude it, man. I love shit that grit and resourcefulness got you through that now you're passionate about sharing it with others and turning them around that's the greatest gift we all have because i remember growing up my 20s i was early successful but it was me me me me me me me me me me me me when you start sharing those gifts and you start spreading it around that's what really unlocks not only greater gifts but it's amazing what starts

the doors that start opening and we had some other doors to start opening when did it all change what was round two and three of this journey the building of keegli my wholesale business was a beautiful dream come true. Unlike what people may believe the perfect entrepreneur looks like, I definitely wasn't in the beginning. I was struggling with alcoholism and addiction to pain medication from a motor vehicle accident. As I'm building this company, I'm still struggling to just maintain life and maintain my head above water. My relationship is good as it can be with a man in that state. I did well. I tried. I was doing okay, but it wasn't until I took a good look inside and I said, what am I doing? Who?

am I? Why am I here? Why am I giving up? Why am I getting my energy and my fuel source from this false light? From these false sources? How do I change this? That took me down a path of self-discovery. And I was reintroduced to Maslow's hierarchy of needs, which I had been originally introduced to in elementary school by a person who didn't understand it themselves. There I was looking at the pyramid and seeing I've been living in survival. And of course, when you're in a survival mode, you do what you've got to do to survive and that means you're clutching and grasping and filling holes of worthiness and filling holes in yourself with whatever you can. And even though it's temporary and even though the chemical lasts, it's half-life and then you got need more of it or you crash and you're on

this hamster wheel of trying to maintain. Eventually, you fall. You fall on your ass and you see that you've got to make a real pivot, a real change, something from the inside out. That's why I really believe success is an inside job. We can kick in as many doors as we want. And we can do this the Newtonian way where every cause has an effect and every action has an equal and opposite reaction. And I can look at the laws of physics and say, okay, I need to have a force and that means I need to have some mass and an acceleration behind me so that I can actually move this obstacle. Or I can work with my spirit. I can work with the creator, the thing that binds all of this together and I can part red seas. I can build universes. I can tap in the divine qualities within me and not have to do this the hard way. And that is where things really started to change. That's where second part. and the third part of this story come from was me getting in and having a real honest look at who I was and how I was showing up in the world and making adjustments and changing my patterns and deciding that I wasn't going to be the same Jamil Damjeet as I was today. I'm going to be a new one. I'm going to make a new choice. And I don't, I can't say you make all the changes and choices all on one day. You'll burn out

and you won't be able to sustain that either. But it was small microchange after small microchange after small microchange slowly. But surely I started to evolve. I evolved spiritually and then I evolved. all emotionally. And then the last drop was physically. I recently dropped 80 pounds. You know, I was a heavier guy and unhealthy at that. I had to make that final adjustment in my lifestyle. And I feel completely different guy today. I'm healthier. I'm more fulfilled. I've made more money with those attributes still there and intact. And I'm continuously learning. I'm still finding myself in hard situations. I recently just went through a separation with my wife, who is a beautiful human and one of the greatest women I've ever met, and it's a friendship that I'll carry on in for

the rest of my life. I learned so much in how that happened. What I can do differently in my life to show up better as a father and as a husband in the future. I'm making those adjustments, and I'm going to continue pushing forward and growing. That brings me to today. I'm ecstatic with what's around the corner. I know that because I'm not living in fear, I don't have anxiety about what's coming. I live in faith, and so I have excitement. You look great. You do look good. I be surprised a little handsome devil lots of doors might be opening for you when i'm ready i guess you know i still got a lot of healing and things to go i know you got the physical but it's all tied together and i love what you said about strength and success hap starts within there's never been a truer

statement everything starts internally and it manifests in the mind or so it starts in the mind and manifests in the body if you don't have your head right in the right head space and that could be spiritually that can be meditation whatever your outlet is but have that being centered and focused and it's just so important. And I know that's had an impact for you. I'm sure the audience would love to hear probably some A&E fans out there, some triple digit flip fans out there. Talk about that experience a little bit. It was wonderful while we did it. Pace and I, my sister and Laura Morby, we got to spend hours and hours and hours on set, hanging out, doing what we do, enjoy each other's company and flip real estate. It was really a blessing and I have a tremendous amount of respect and love. for our friends at A&E for the opportunity that we had. They originally signed us to a six-season deal. And as you guys are probably aware, we only have produced two of them. They did have an order for us of 30 episodes, which Pace and I humbly declined.

The reason for it is just, at the end of the day, we are principles in the real estate business. Our daily job is not choosing tile and picking paint colors, which unfortunately in a visual medium like TV is something that people want to see. and the general public doesn't realize that real estate investors don't do those things during the day. I've got people that pick tile. I've got people that choose the paint color. I have staff that handles those things. I'm not the guy doing that. I'm looking for new opportunities. You're doing the boring. Not the boring stuff, but the boring as far as TV goes stuff, the roll up your sleeves and deals and hunting and networking and all that shit. They want me to demo a wall. It's just not authentic to the experience that I have on a daily basis. And when you look at it from the perspective of how long it takes to shoot an episode,

they're looking at 80 to 100 hours of footage for a 42-minute episode, which is oppressively long. And it takes us out of our day-to-day responsibilities. It removes us from being able to show up better for our communities, which I'm 100% committed to. And it takes us away from being able to be there for our staff. I've got over 300 people that rely on Jamil Damjeet being the best version of himself every single day. and to be there to answer questions, to motivate, to lead. And if I'm on a TV set pointing at tiles and choosing paint color, I'm not doing that. Unfortunately, that's just not a show we want to continue making.

Again, no judgment for people who do and a tremendous amount of love and respect for our producers and friends at A&E. They are professionals. I have so much respect with A&E. We originally told them, hey, we're never going to do this fake drama stuff. I'm not going to throw a contractor under the bus or a vendor under the bus or a vendor under the bus and pretend like somebody screwed something up, they don't do that. Now, if something authentically happens and a mess up occurs and we catch it and we want to talk about it, I'm totally down, but I'm not going to make it up, but we're not going to lie. And there was only one instance

where a producer, a director had asked for us to do that. And I walked off set. I just left. I got in my car and said, no, not doing it. And then the executive producer got on the phone and told that director, what are you doing? He's like, I'm doing what I do. This is what we're supposed to do. He's like, not these guys, not this show. I was apologized to, got back to set. They said, you just do what you do. And I'm like, we do it by heart. We do this thing for real. And I'm never going to

dramatize and throw someone under the bus. Unfortunately, that's not the TV we make. They honored that. And they produced a television show that I am proud of, that I know my children will be proud of. And even though it will live in the ether somewhere on the internet, at some point, in 20 years, my kids

will look at it and say, wow, look how fat dad was. This is cool. But we want to do something that is meaningful on a societal level. And so Pace and I are self-producing a show where we're going to look at how we can help solve problems we have a hand in. Now, there's no doubt in my mind that real estate investors, wholesalers, fix and flippers have a hand in the inventory shortage and affordability going where it's gone in the United States. And if we want to pretend like we don't have a hand in it, then we're blindly diluting ourselves. That's not to say that I'm not going to participate in it because that's how I feed my family. It's the way that like,

is and that's just unfortunately how it's going. So houses are going to get more expensive. They're going to get harder to buy. But knowing that I have a hand in things getting more expensive, can I not find ways to help the people who are being negatively impacted by what's going on in real estate? And that's what Pace and I want to do. Moving forward, we're self-producing a show where we will go into Skid Row. We're going to go into tent cities and we're going to find vulnerable people who really want to affect some change in their life and we'll show them how to do this business. We'll show them how to get deals. We'll show them how to make money. And we'll do that with our own time, our own resources and prove that you can teach a man or a woman to fish and change their existence.

That's going to be how we can, A, at least begin helping solve the problem that we know is sweeping the country. And then change that model from people that are experiencing being unsheltered to single parents who are doing the best they can to other disenfranchised communities in the United States that would benefit tremendously from the non-sheltered. knowledge the pace and I have gained in this industry. I don't give a dang if anybody watches it or doesn't watch it for the fact that we'll be able to do it and do it authentically and it'll be a subject matter that we're very tied to, that we're very interested in and that we know will make a huge impact on society. And if you watch that and you see that we can help a person struggling with addiction or

struggling with other factors in their life and help them do the business, then what excuse to somebody who has everything going for them, except lack of priority and how they want to spend their downtime, whether that be watching Netflix or doing something that can help change their financial life, when we can show that and prove the concept of people that, hey, anyone can do what we do, then we'll have a tidal wave of people that will start taking responsibility for what they produce in this world and how they show up. I love that, man. I can't wait to watch it. I'm surprised, and you probably did, but maybe I didn't have it. discussion with A, you're pitching it there. We did, but they just said people aren't ready for it.

They want to still see house porn. And that's okay. That's totally okay. It's not until you break the mold that new molds are formed. And maybe we got to self-produce this and show how strong the appetite is from a internet basis. Because Pace and I have really good YouTube channels and our communities are super connected and they are engaged and they're all excited to see this come to fruition. Even if it's just self-produced. and watched by our communities, cool. If it catches on and others see utility and want to share it and do the same, amazing. And then if that then turns into a conversation with A&E again where they say,

thanks for proving this. Now we want to do this type of show. Awesome. And if not, awesome. There's not a day that goes by since not filming the TV show that I miss it. It's not sexy, brother. I know. I've been on both sides of the show business for quite a while,

creating ads for some of the biggest brands of the world, and sitting on some of those TV sets and everything else. And it's a lot more work than people realize. We talk a lot about marketing on this show and the power of branding. I happen to own the trademark on the phrase, it pays to be known. With that said, I don't want to gloss over too much. You did homage to A&E. But the power of television, even still today, it's diminished.

You guys did it for a reason, the show. It was good for them, good for you. I talk to people all the time. Don't get it twisted. If you get the opportunity to grow your reach and frequency and awareness on the power of the medium of television, as long as it's in line, like you said, with your morals, your beliefs, and it's not altered, you better take that ticket. It's still very powerful.

It absolutely is. And tremendous amount of love and respect for A&E and Six West, our production company that was a huge support and partner through the whole process. And Pace and I and the rest of the cast have just the utmost respect for all of them. it was a great opportunity and I'll always have the TV show under my belt. I'll always be able to lead a bio with A&E TV star and that's awesome. It'll never be stripped from me. It's not something that you can never take away, but I did my time.

If you have the opportunity, of course, take the opportunity. Will it be a lot of work? Yes. Will there be a tremendous financial return? No. Will you get credibility and unlock doors that you wouldn't have been able to unlock without it? Absolutely. And will those doors lead to?

a greater ROI's an opportunity, you better believe it. TV show is not just the eyeballs of the housewife or the house husband that's watching you on a Sunday at 11 a.m. while they're looking after the kids and doing DIY home project. That's not the guy who's going to stroke a check and join your mentorship or your coaching or do a deal with you and buy a wholesale property. That's not the person. The voyer isn't the avatar of my customer. But my customer respects that I'm on that medium. And it lends to my credibility. It lends to the visibility. And let's just be honest. It's cool for somebody to have a TV show. And it's even cooler for you to be friends with or know or learn from that guy. When I'm on my coaching calls with a few hundred people and they are having a lengthy discussion with me,

how many times do I hear? I just can't believe I'm talking to you. And I'm like, bro, I just farted. It's all good. Jamil, I'd love you even if you weren't on TV, man. Thank you. Talk about some of that. coaching stuff. You mentor, you coach teaching people to do what you do. You mentioned helping on the TV show, which will be amazing. But for the everyday person, how are you unlocking these opportunities? I built the nation's largest wholesale operation because I scaled and I created a replicatable business where people didn't think it was really possible. No one's ever sold a

wholesale business until we came in and franchised ours and built a replicatable model that has now been operating in over 118 different markets under the same brand. When you're able to do that, you can prove to folks that this is a replicatable business and this is a sellable company. That for me is really awesome. But in addition to that, I looked at this business from a relationship standpoint. And what most wholesalers were doing in the past and what people were teaching them to do was very difficult lead generation techniques like cold calling, door knocking, putting out banded signs and direct mail, and all of this is extremely expensive, time consuming, and the ROI is maybe, maybe not. Because for somebody that is working at W2 and doesn't have a lot of expendable resources

and disposable resources available, then asking that person to gamble $5,000, $7,000 on the possibility they may get a lead or get a contract is a hefty ask. I know we could talk forever, bro. Where can everybody keep up with all these projects, everything you got going on and where can everybody keep up with everything? My YouTube is the best place. It's just YouTube.com slash Jamil Damjee. J-A-M-I-L, D-A-M-J-I. Also, find me on Instagram at J-D-A-M-J-I, so at J-D-A-M-G.

Send me a DMG. I love hearing from folks. Subscribe to my YouTube, learn what I do for a business. I love cracking jokes. I like making people laugh. You'll be entertained. You'll be educated. If there's anything that I could do to help you with learning something that I have a skill at,

send me a DM and I'm happy to be a part of your world. Thank you so much for coming on, bro. Hey, guys. You know, you know, to find us Ryan isright.com. You can find links to all of Jamil's stuff, all of the highlight clips from today, all of our social media. You can find me at Ryan Alford, that blue check mark. But had it before you could buy it. We'll see you next time. We'll write about now. This has been right about now with Ryan Alford, a Radcast Network production.

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