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INTERVIEW | Make Money Building Affordable Housing with Evan Holladay

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Evan Holladay is an experienced real estate developer and investor who has developed over $694 million in projects and more than 2,600 affordable multifamily units. As the Founder and CEO of Holiday Ventures, Evan specializes in intentionally designed, sustainability-focused affordable and mixed-income communities. He also teaches other aspiring developers through his 12-month mentorship program, Affordable Development Mastery. In this episode, Evan shares the scrappy, relationship-driven journey that took him from pre-med student to nationally recognized affordable housing developer. On this episode we talk about: Why relationships often create more opportunity than credentials How Evan leveraged mentorship and persistence to break into real estate development The mindset shift from “being qualified” to becoming resourceful Using podcasting as a networking accelerator and personal MBA Building 1,200+ affordable housing units in seven years — and scaling with impact Top 3 Takeaways Opportunity comes from proximity. Getting in the right rooms — even before you feel ready — can change the trajectory of your career. Professional persistence beats passive applications. Evan didn’t just apply for jobs — he engineered access to decision-makers. Impact and profit aren’t mutually exclusive. Thoughtful affordable housing can create strong investor returns while transforming communities. Notable Quotes “Opportunity comes from people. Value comes from competence.” “Every major pivot happened when I wasn’t 100% ready — but I took action anyway.” “You jump off the cliff and build the plane on the way down.” Connect with Evan Holladay: Instagram / LinkedIn / YouTube: @evanholladay Holladay Ventures Affordable Development Mastery  Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.  Capture leads, nurture them, and close more deals—all from one powerful platform.  Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices

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INTERVIEW | Make Money Building Affordable Housing with Evan Holladay

Travis Makes Money

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Travis Makes MoneyINTERVIEW | Make Money Building Affordable Housing with Evan Holladay. Machine-transcribed; use the interactive transcript above to jump the player to any line.

Baseball is back, and the first pitch is on Netflix. The New York Yankees, led by seven-time all-star Aaron Judge, head to the San Francisco Bay to take on Rafael Devar's San Francisco Giants. This season kicks off with one exclusive opening night game. Watch MLB opening night, the New York Yankees versus the San Francisco Giants live on Netflix. Tonight at 8 p.m. Eastern, 5 p.m. Pacific. We're listening to the Travis Makes Money Podcast, presented by GoHighLevel.com. For a free 30-day trial of the best, all-in-one digital marketing software tool on the planet, just go to GoHighLevel.com slash Travis. What is happening, everybody? Welcome back to the Travis Makes Money Podcast. We're trying to help you make more money today on the show. I have a new friend, or old friend of mine, excuse me, something I've known for quite some time, Evan Holiday. He's an experienced, real estate developer, an investor known for his work in developing over $694 million in projects, and over 2,600 affordable multi-family units.

He's the founder and CEO of Holiday Ventures, where he and his team specialize in creating and investing in affordable and mixed-income communities, guided by intentional design, sustainability, and thoughtful place making. Evan teaches others how to develop affordable housing through a affordable, developed mastery at 12-month mastermind and mentorship program that he, of course, is the head of the master of Evan with something, and welcome to the show. Hey, man. Thanks for having me on, and good to catch up. Okay. So, you're 14 years old. Your teacher comes to you in school, points out you and goes, Evan, what do you want to be when you grow up? What did you say at that time, and why is it not real estate development? That is a good question. I thought I wanted to be a doctor, specifically an anesthesiologist. So I was, I think, 13, and I had a pretty nasty, soccer injury. My knee, basically, I had multiple surgeries, I had MRSA, I was pretty bad infection, and

yeah, they're like, hey, if this doesn't get, like, if we didn't catch this today, then we may have had to, like, take off your entire leg, like, am I MRSA or no joke, bro? Yeah, yeah. Yeah, I was really bad, and so actually, I mean, my uncle was the orthopedic surgeon who did the surgery, but I really got to know the anesthesiologist, and I was like, wow, like, I had some doctors in my family, like, my uncle, my dad was not, but I just had a phenomenal experience with that, and I was like, man, I want to be like a doctor. These guys are cool, and they get paid a lot of money, and they help people. And so I went down the pre-med route, and it wasn't until, I mean, I was like shadowing doctors, I was volunteering at the hospital. I was doing everything you could do to get into med school, and then I took my first bio and my first kin class in college, freshman year, and I was like, man, this shit sucks. I've been doing, like, I'm not, I don't care about like, covalent bonds, and like, all these other random things, I was like, I can't do this for another 10 or 12 years.

Dude, you know, it would be a crazy study would be to see how many people didn't do something that was actually somewhat meaningful to them because of all of the bullshit that college makes you jump through, like all the hoops that they set up that work, they require you to jump through, even though it doesn't have anything to do with like the field that you want to study. Like, the first two years are there, and it's basically just a waste, it's like, hey, it's like retake grammar class, and it's like, wait, but I already took that, that was just like, I have to pass high school first, now I'm in college, and I just start studying the thing that I want to study, you know what I mean, it's just like, that's like one of the things that I look at the point to and go like, yeah, I mean, that's just as scammy as any online course I've ever seen, except for as way more expensive. It's a pretty set up for four years plus, plus food plans. And a bank will actually loan you a quarter of a million dollars as an 18 year old with zero credit history blows my mind. You can't go get a credit card. Yeah, like you have to get a coast, your mom or dad have to co-sign to get a credit card

or you have to have a secured credit card, like you actually have $500, and that's the limit on that card now. They won't even give you 500 bucks on a credit card when you're 18, when you don't give you 250 grand to go get a degree, they won't ever use it. Imagine if people were using that 250 grand to buy a house, and we're taught how to, you know, that's the most stated 18 years ago, but they wouldn't be able to buy the house because they couldn't qualify for the, you know what I'm saying, like that's so crazy excuse that. How is this not viewed as predatory lending? This is like, to me, the very definition of predatory lending because that person, like you can't even file bankruptcy to get out of that debt. It's going to follow you for the rest of your life, you know what I'm saying, anyway, I don't know. Took us on a tangent. Yeah. You're preaching to the choir. I mean, I was fortunate I had a scholarship, and I didn't have that debt burden, but I immediately came into school as soon as I realized that I did not want to be a doctor. I was like, all right, what else, what else can I do that I would love to do?

I took an economics class, I fell in love with economics, I was like, I already think like this, and I'm just taking classes that align with the way my mind already thinks. And then at the same time, there was a student housing development announced on campus. And I was like, man, something about that, like that is calling my name. It was just pulling me in, and I basically mentioned to one of my mentors, I was like, hey, that sounds really cool what he's working on. And he's like, really? He's like, I know the developer. Let me introduce you. I'm a total coincidence. And you know, just putting it out there, what I wanted, and that helped me get my foot in the door. Now, he didn't hire me right away. I had to call him constantly, and he's like, all right, prove yourself. Show me that you can bring some value. He's like, bring people out to my groundbreaking. So I got my buddies, I got them pizza, and in return, they passed out flyers for the groundbreaking. And we had over 200 people show up for this groundbreaking. And still I had to keep calling them, keep calling them, you know, until he finally was

like, all right, find your hired. He hired me as a leasing agent, or a leasing assistant, basically pre-least all the units, 355 beds, and five months, amazing experience, taught me so much in a short amount of time. But I also realized I was like, this isn't what I want to be doing. I want to be doing what she's doing. I want to put the deal together. I want to like see the vision to reality. And I want to see things come out of the ground that I helped formulate. And that got me really excited. And then at the same time, I was part of a program in school where they pair you with nonprofit to volunteer with. And I was just randomly paired with a nonprofit that provided affordable housing for single parents, usually single mothers going back and getting their college degree. And you know, I was mentoring some kids that were going through the program with their parents. And it was just such an eye-opener to me as like, holy crap. Like these kids, their whole lives are going to be changed by their parents going through this program and them having the community and support for their parents to go off and

get a better job, get a better education, and then get a better job. And you're changing that whole family trajectory through housing as a foundation. Yeah. And that just blew my mind. I was like, all right. People and I want to build stuff that I can do that through affordable housing. And I just dove all in. As part of a class, we were in an entrepreneurship program and we had to start a business. And I convinced my team, I was like, we're doing something with affordable housing. So we came up with this game plan of doing modular affordable housing and using houseboat manufacturing plants that had laid off 1100 skilled workers with the housing market crash. So we took a same foundation, the same box that would go on water. We just re-tooled it and re-tooled the facility to build it on a foundation. And we ended up winning some competitions and we're like, man, I think we have something here. But I also knew I was like, we are so green, I need to learn from somebody who has done this before. And so I applied for a group that was the biggest affordable developer around and Louisville.

And I was lucky enough to get a job there. But also like put myself on the right room with the right people. I knew they were going to be at a golf outing. So while I was also planning for a job, I figured out a way to get invited to the golf outing and somehow made it into the for some with the owner in his buddies. They had a guy that like got sick. So their fourth guy got sick and I just said, hi, I applied for this job, would love to talk more. They're like, really? They're like, well, we got an extra spot. Why don't you join us? So I spent a whole day golfing with the owners. I'm terrible at golf, but I played the best round of golf of my life. They literally said the last putt of the day, they're like, hey, if you make this 40 foot putt, you get a job. And I was like, what? I was like, it's a 40 foot putt. It's like curving, you know, sloping green. And I know joke. I nailed the putt. And I was like, what? And we're all like high five and it hugged in. I just met these guys this morning. And then by the end of the day, I find we'll give you a job.

And then we got in two weeks later, I was on a plane to Brownsville, Texas. You know, I had no idea where that was, but I was like, we're going to Brownsville. They're like, we need some affordable sites tied up in South Texas. So I was on a plane that next week and was looking for deals and worked there for six years and really cut my teeth and figured out like, hey, this is how you put deals together. To that part of Texas. No, I was, I was always traveling. Oh, okay. Got you. Yeah. Yeah. There's so many parts of that story. I love. First of all, let me say opportunity comes from people. Value comes from competence. I want to throw that out there because there's just been a constant question that I've asked a ton of people now at this point, which is who you know or what you know, more important and why. And I initially engineered that question because the show is called Building Network. This episode of the show is brought to you by Mars Men. So look, as I don't know if everybody listening knows this, but a couple years ago, I was diagnosed

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That's mengo2mars.com. This episode is brought to you by Indeed. Stop waiting around for the perfect candidate. Instead, use Indeed sponsor jobs to find the right people with the right skills fast. It's a simple way to make sure your listing is the first candidate to see. According to Indeed data, sponsor jobs have four times more applicants than non-sponsored jobs. So go build your dream team today. With Indeed, get a $75 sponsor job credit at Indeed.com slash podcast, Terms and Conditions Apply. I started it in sales like everybody said, that phrase all the time, who you know is more important than what you know. I figured by asking that, everybody would just say, who you know, and then I'd go, great. That's what I think too. Then we talk about relationships for the next 20 minutes. I found out there was a very large mixture of people, where some people would say what some people would say who. I still am on the who side for several reasons, but that's not the point of this conversation. However, it's clear that you need both of them, that it's not just a matter of who

you know, but you also have to deliver them with the people they know. However, when you're first getting started, the who to me is more important because of the things that you just mentioned. This whole thing started with just you knowing somebody who made an introduction to the guy who owned the development project, so you can get your foot in the door, and then you get paired with these people at a golf outing. They give you this opportunity to come work for them and learn the business. It's like, you're what will exponentially increase if you get around the right who. That's why that's one of the reasons why I always value who more than what is that it's not always true the other way around. If you get really good at what you do, it's not necessarily guaranteed that you're going to automatically increase the number of people who know you. Obviously, that's sort of nuanced because if you get really good at something like

creating content and you have 10 million followers, then you're going to meet a lot of people that way. It's not a one-size-fits-all type of thing, but my point is just to say that the volume of learning that you are able to do, that early on in your career, to that high of a level with those types of people, was directly related to your ability to just say, hey, screw the fonds of being afraid of rejection, go for it, and I'm going to put myself out there and see what happens, and you met the right people, said the right things, got the right opportunities, and then now sort of the rest of the history. Where would you place the value of the relationships that you've had in your life in regards to how successfully you've been able to come? Yeah, I would say I would not be anywhere to wear in today without the relationships along the way and the mentors and the connections in my network. But I do agree. I think it's definitely a mix of both because I think I was, like you said, I was not afraid.

Let me rephrase that. I was afraid of rejection, but I was willing to overcome that being afraid because it sounds easy to say in hindsight, but if I'm being honest, I think I was always scared of rejection, and I was always scared of the unknown and scared of the next step. And also, am I being too pushy? If I'm calling this guy constantly, am I calling him too much? Am I going to ruin the relationship? And I'm constantly having that back and forth conversation in my head of am I doing too much or too little and always trying to figure out how to put myself in the right room, but also not be too over the top about it either. And so I think everybody listening, knowing that like it's okay to have those conversations, it's completely normal to have those in your head thoughts. But I do think it's like combining that not being afraid of rejection plus like persistence and not being willing to give up until you get what you want or you get a yes.

Yeah. And there's a big difference to between professional persistence and pushy persistence. One of them people respect the other one annoys the hell out of people and it sounds like you were more on the professional side than the pushy side. And then the competence piece to those like how many other people would have been more qualified on paper, had more experience, maybe a better degree, et cetera, et cetera, to get the position that you ended up getting. But just weren't willing to put themselves in that position to be able to get the thing. Like they're the ones, they're the ones that are just sending out a thousand applications on, indeed, and zippoprooter and then crossing their fingers and then going to go. The job market stinks, you know, it's like, no, no, it just means that you stink at getting the opportunities that you want because you're not willing to go out, put yourself in positions to meet people who can provide those opportunities to you. Yeah. You're foot in the door. You must perform. Yeah. Like you can't just be the person who gets your foot in the door because then if you suck,

you're gone. I see. You can't be out of the door. I see. But the nice thing I found about that, and I love for you to speak into this. The nice thing that I found about that is like, it's not necessarily competence in the field, it's competence with your ability to learn and confidence in your ability to figure it out. Like you can put me in the situation. I may not know what I'm doing day one, but by day 30, I will be your best person or like, you know, that attitude of just being willing to figure it, that f out, that by itself is enough competence to be able to get you the opportunities and then to be able to, on the back end, perform well. And I think that that prevents a lot of people from trying to get their foot in the door because they're not confident in that. They're like, oh, I get this opportunity, you know, I'm not qualified for that opportunity yet. You know what I mean? Like somebody told me that probably like seven, eight years ago, we're talking about meeting some, you know, I think it was Gary B and she was like, I just, I've reached out to Gary B yet because I want to have something really good when I reach out to him,

you know, well, the punchline is that was almost a decade ago and still no reason to reach out to Gary B. You know what I mean? Like sooner or later, you got to just take the swing and try to hit the home run, you know what I mean? Yeah. Yeah. I think every major pivot or area of growth for me happened in those moments of like, I'm not 100% prepared. I'm not 100% ready, but I took action anyways and persisted through that, you know, uncertainty, you know, and speaking of podcasts, that's how you and I originally connected was being a guest on my monumental podcast. I mean, that, that is another story where I was like, you know, I'd been working at this developing company and I'd been constantly learning like you mentioned, like I'm always learning about how I can better myself personally and professionally. How can I market myself? How can I find a great relationship? How can I add value to other people? And I learned about podcasting and how it's an amazing tool, you know, to grow a network,

to grow brand, to add value to your community and to connect with amazing guests through the process. And so I knew I wanted to do my own thing and so I also was thinking about, well, I also want to build my own brand, you know, a little bit prior to me starting my own thing so I can have something to run with and some momentum by the time I started my own business. And so I also met this amazing venture capital and set this event, it was like kind of in passing and I was like, man, I want to keep talking to this guy, but I don't have a good reason why I've been toying with the idea of a podcast in my head. And so I went out of the event into the car with my wife and I was like, hey, I really want to keep talking to them. Maybe I throw out the idea of the podcast. She's like, yeah, do it. Why not? So with her little nudge, I was like, yeah, let's do it. I'm going to go back in there and I went back in and I said, hey, I have podcasts. I have a podcast where I interview successful entrepreneurs and leaders just like you. I'd love to have you on the show. And he's like, sure, here's my card. Here's my personal self a number. Let's let's catch up and let's do it.

And yeah, I was like, freaking out the whole time, but he said, yes. And I was like, oh, shit, I need to figure out how to do a podcast. So like the next 30 days was like a crash course. I was taken like John Lee Duma's, you know, podcast period, like, learning all about podcasting. And I was even like interviewing, practicing on my buddy. And yeah. And then after nailed the interview and then afterward I told him, like, hey, I'm not going to lie. Like this is my first interview. He's like, really? He's like, you crushed it. That was amazing. And it was like just an extra vote of confidence. I was like, yeah, he's right. I totally got this. Yeah, one of those things you jump off the cliff and build the plane on the way down sometimes. Yeah. That is one of the biggest reasons I encourage people to podcast. It's just the excuse. Yeah. It comes. You just need an excuse to keep the conversation going. You just need the excuse to have the initial connection to get your foot in the door. And that's conversation is a much better excuse than say sales call.

You know, like people, how many, how many LinkedIn DMs do you get on a month? One of the reasons of somebody. America leads the world in medicine development. It matters. We get new medicines first nearly three years faster. Five million Americans go to work because we make medicines here at home and not relying on other countries keeps us safe. But China is racing to overtake us. Will we let them or will we choose to stay ahead? When America leads, America cures. Let's tell Washington to keep us in the lead. And how at America cures.com paid for by Farma. As a chef, I know flavor does begin in the kitchen. It begins on the land. And West Homes Nature-led Australian Wagyu is a story written in the landscape of Northern Australia. Cooking is storytelling. And West Homes Wagyu carries a story of Northern Australia itself.

Raw, powerful, and deeply authentic. It's a testament to the passion and care raised in the rhythm of Northern Australia. I'm Chef Maylin from ADA Club in Los Angeles and I invite you to visit westhome.com slash Maylin to learn more. And taste a story. Only West Home Nature-led Australian Wagyu can tell. That's W-E-S-T-H-O-L-M-E.com slash M-E-I-L-I-N. That's trying to sell you something. And they all sound almost exactly the same. They all are the same generic pitch jargon that are trying to move you to a sales call. But if one of those is, hey Evan, will you be on our podcast? Probably going to respond to that. And you're probably going to say yes. Even if you don't know who that person is or what their show is about, probably going to say yes because it's objectively a good use of time. Like you've got to create content if you're an entrepreneur, right? You need more credibility if you're an entrepreneur. You want more SEO and backlinks if you're an entrepreneur. All of those things are really good. And regardless of the size of the show, it still provides all of those things for you.

So yeah, sure, let's go ahead and do it. And then all of a sudden, you're on an hour-long conversation with somebody. You find out you have a ton of things in common. You're building similar businesses. Maybe you live in similar places or maybe in the same state or something. You know what I mean? It's just the springboard to be able to have the excuse to continue having conversations with people who are up to really cool things in the world, which I think is one of most underrated parts of actually having the podcast now. Yeah. I could not agree more. That's what I preach to is encourage people to build their own platform because there's so much value in the network. And I consider that, I mean, we did like 200 episodes over four years and considered that like my personal MBA and my personal network building stage and helped us really be successful in launching hot adventures. Yes. So tell me about holiday dentures. When did you launch this? What has been the run rate so far? You know, what are you proud about? What has been scary to you? Yeah. I say, my wife and I started the business seven years ago.

It was literally just us food strapping it in our one bedroom, one bath apartment on the second floor of somebody else's house when we started. And today we have been able to build over 1,200 units in the last seven years. And is it like a similar model with like manufactured homes type of a thing or what? Tell me about it. No. Now we build stick frame construction. So on site, we'd like to get into module. I'd like to get back to that. I really do believe in modular long-term. But really what we build is intentionally designed and develop affordably priced communities where we incorporate sustainability, place making such as like retail or community centers. But we partner with nonprofits to help provide wraparound services for our residents. So really taking that kind of that initial model that I learned in in college that kind of really opened my eyes to affordable housing, we've taken that and made it into our own version of that and really trying to figure out how do we scale that. And so we've been able to accomplish 1,200 units here in Nashville to date.

And we're now looking in Columbus, Ohio and then throughout the southeast and looking for ways that we can really create impact driven housing while also creating great returns for our investors. Yeah, creating long-term legacy and impact. Have you heard of Voxable? Yeah. Maybe I should make an intro sometime. They're out here in Vegas, Juliana is a friend of mine, but they are, it's crazy when you go to their manufacturing facilities like a couple hundred thousand square foot industrial building. But it's, they're building these houses on just like an assembly line, like a car, you know. But they're all free. It's amazing. Maybe there's one bedroom all of them, so I fly a lot toward a couple of them. I was like, this is actually, this is actually pretty nice. Yeah. I could see my Elon lived out of this for a while. Exactly. Exactly. Well, listen, dude, I appreciate taking the time to come on the show and share a little bit. I love, love the story, love the scrappiness. And each part of the story, from getting the initial, how do I get my foot in the door?

I don't even know. It seems like this would be a cool path for me, no idea how to make it happen. And then to be able to learn while you earn, meaning like you've got a great opportunity to go work with somebody who's doing exactly what you want to do, they pay you money, and they teach you everything, you know, like great scenario. And then to launch out on your own, start something with just you and your wife in a one-bedroom apartment, have a turning to what it's turned into today plus the podcast and everything else you're working on, man. But I just love everything that you're doing. I appreciate it for taking the time. I know you're a busy guy. So what can people go to get more from Evan and Holiday Ventures? Yeah, I appreciate that. And thank you for having me on. All socials are Evan, Holiday, H-O-L-L-A-D-A-Y. We do put out content weekly on YouTube as well. And then for those interested in doing what we do, we also teach others through affordable development mastery. Perfect. Evan, Holiday, go check out some of the stuff that Evan's up to. That's H-O-L-L-A-D-A-Y, H-O-L-L-A-D-A-Y.

Make Hala and Day. Have a good day. Go check out some of the stuff that he's working on, and I know you'll not regret that. Everybody else doesn't even remember, money only solves your money problems, but a little bit easier to solve the rest of your problems when you have money in the bank. So let's start there. Here on the channel, it's going to be $25, thanks for tuning in. Catch you guys next time. Peace. Jackson, you had has a great tax prep deal, $149 or less. Missing out is like ignoring the check engine light in your car. You regret it. Seriously, the price is only $149 or less, no matter how complicated. But don't wait. Like when you get a password expires today alert or you're shopping online and there's only one item left, it's like your taxes are in the cart, just complete the purchase. Hurry, this deal for $149 or less is like your phone at 1%, it's about to power down. Limited time offer for new clients on federal returns, participating locations only, in terms of Jackson, you would dot com slash $149.

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