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Travis
You'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 travis.
What is happening everybody? Welcome back to the Travis Makes Money podcast where it's our mission to help you make more money. Today on the show, I have a new friend or old friend of mine. Excuse me, somebody for quite some time. Evan Holiday. He's an experienced real estate developer and investor known for his work in developing over $694 million in projects and over 2,600 affordable multifamily 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 affordable develop mastery, a 12 month mastermind and mentorship program that he of course is the head of the master of. Evan, what's up man? Welcome to the show.
Evan Holiday
Hey man, thanks for having me on. And good to, good to catch up.
Travis
Okay, so you're 14 years old. Your teacher comes to you in school, points at 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?
Evan Holiday
That is a good question. I thought, I want 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'd have multiple surgeries. I had mrsa. It 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.
Travis
Like, yeah, MRSA is no joke, bro.
Evan Holiday
Yeah, yeah, yeah, it was really bad. And so actually, I mean, my, 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 chem class in college, freshman year. And I was like, man, this shit sucks. What am I doing? I was like, I am not. I don't care about like covalent bonds and like all these other like random things. I was like, I can't do this for another 10 or 12 years, dude.
Travis
You know what 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, 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. It's like the first two years you're there, it's basically just a waste. It's like, yeah, hey, retake grammar class. It's like, wait, but I already took that. That was like, I have to pass high school first. Now I'm in college, I just start studying the thing that I want to study. You know what I mean? It's just like, it's, that's like one of the, one of the, one of the things that I look at to point to and go like, yeah, I mean that's just as scammy as any online course I've ever seen. Except for it's way more expensive.
Evan Holiday
Except for you sign up for four years plus residential, plus food plans and
Travis
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. 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. Yeah, they won't even give you 500 bucks on a credit card when you're 18. They'll give you 250 grand to go get a degree that you'll never use.
Evan Holiday
Imagine if people use that 250 grand to buy a house and we're taught how to, you know, invest in real estate at 18 years, but they wouldn't
Travis
be able to buy the house because they couldn't qualify for the that, you know what I'm saying? Like, that's so crazy skewed about it. This, how is this not viewed as predatory? 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
Evan Holiday
rest of your life. Get off.
Travis
You know what I'm saying? Anyway, I know. Took us on a tangent.
Evan Holiday
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. But I immediately came into school as soon as I realized 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. 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 mean, total coincidence.
Travis
Wow.
Evan Holiday
And 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 to this groundbreaking. And still I had to keep calling him, keep calling him, you know, until he finally was like, all right, fine, you're hired. He hired me as a leasing agent or leasing assistant, basically pre leased all the units. 355 beds in 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 he'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.
Travis
Yeah.
Evan Holiday
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. I was 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 the foundation.
Travis
Yeah.
Evan Holiday
And that just blew my mind. I was like, all right, I want to help 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 I. 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 retooled it and retooled the facility to build it on a foundation. And we ended up winning some competitions. We were like, man, I think, you know, we. 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 in Louisville. And I was lucky enough to get a job there, but also, like, put myself in the right room with the right people. I knew they were going to be at a golf outing. So while I was also applying for a job, I figured out a way to get in invited to the golf outing and somehow made it into the foursome with the owner and 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. Nice. They literally said the last part of the day, they're like, hey, if you make this 40 foot putt, you get a job. And I was like. I was like, it's a 40 foot putt. It's like curving, you know, sloping green. And I. No joke, I nailed the putt. And I was like, what? And we're all like, high fiving and hugging. I just met these guys this morning. And then by the end of it, they're like, all right, fine, we'll give you a job.
Travis
No shit.
Evan Holiday
And 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.
Travis
Moved to that part of Texas.
Evan Holiday
No, I was, I was always traveling.
Travis
Oh, okay, gotcha. Yeah. I thought you're saying you were there for six years. I was like, damn.
Evan Holiday
Put in the work.
Travis
Yeah. Dude, 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. This has been constant question that I've asked a ton of people now at this point, which is who is who you know or what you know more important and why? And I initially engineered that question because the show is called Build, you'd network.
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Travis
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Travis
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Travis
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Travis
when I started it, and so it was like everybody said, like, I heard that phrase all the time, you know, who you know is more important than what you know. So I figured by asking that everybody would just say who you know, and then I'd go, great. That's what I think too. And then we talk about relationships for the next 20 minutes.
Evan Holiday
And I found that there was like
Travis
a very large mixture of people where some people would say what, some people would say who. And I still am on the who side for several reasons. But that's not the point of this conversation. However, there's. 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 with the people that you know. However, like when you're first getting started, the who to me is more important because of the things that you just mentioned.
Evan Holiday
Right?
Travis
So this whole thing started with just you knowing somebody who made an introduction to the guy who owned the development project so you could get your foot in the door, right? And then you get paired with these people at a golf outing and they give you this opportunity to come work for them and learn the business. It's like your. Your what will exponentially increase if you get around the right hoop. And that's. 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. Now, obviously that's sort of nuanced because if you get really good at something like creating content and you have 10 million followers, then, like, you're going to meet a lot of people that way.
Right?
So it's not a one size fits all type of thing. But my point is just to say that, like, the, the volume of learning that you were able to do at 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, you know, thoughts of, of being afraid of rejection.
Evan Holiday
Right?
Travis
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, you know, now sort of the rest is history.
Sponsor/Ad Voice
Where.
Travis
Where would you place the value of the relationships that you've had in your life in Regards to how successful you've been able to become.
Evan Holiday
Yeah, I would say I would. I would not be anywhere to where I am today without the relationships along the way and the mentors and the conn 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, I was not afraid. I mean, let me rephrase that. I was afraid of rejection, but I was willing to overcome that, you know, being afraid because, you know, it sounds easy to say in hindsight, but I mean, you know, if I, if I'm being honest, I think I was, I was always scared of rejection and I was always, you know, scared of the unknown and scared of the next step. And, and also, like, am I being too pushy? Like, if I'm calling this guy constant, I'm like, am I calling him too much? Like, am I going to ruin the relationship? You know, And I'm constantly having that back and forth conversation in my head of like, am I doing too much or too little?
Travis
Yeah.
Evan Holiday
And you know, always trying to figure out how to put myself in the right room, but also not, you know, be too, 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, 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.
Travis
Yeah. And there's a big difference too, 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, the competence piece too, though, is like, how many other people would have been more qualified on paper, had more experience, maybe a better degree, etc. Etc. 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 thing. Like they're the ones, they're the ones that are just sending out a thousand applications on Indeed and ziprecruiter and then crossing their fingers and then going, the job markets stinks, you know? Yeah, 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. Now once you get your foot in the door, you must perform.
Evan Holiday
Yeah. Right.
Travis
Like, you can't just be the person who gets your foot in the door, because then if you suck, you're gone
Evan Holiday
as soon as you can't be out of the door. Just.
Travis
But the nice thing I found about
Evan Holiday
that, and I love for you.
Travis
Speaking of this, the nice thing that I found about that is, like, it's not necessarily competence at the. 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. That attitude of just being willing to figure it the f out.
Evan Holiday
Yeah.
Travis
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, man, I get this opportunity. You know, I'm not qualified for that opportunity yet. You know what I mean? Like, I had somebody tell me that probably, like, seven, eight years ago, we're talking about meeting some, you know, I think it was Gary Vee. And she was like, I just haven't reached out to Gary Vee yet because I want to have something really good want to 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 Vee. You know what I mean? Like, sooner or later, you got to just take the. Take the swing and try to hit the home run. You know what I mean?
Evan Holiday
Yeah, Yeah. I think every. 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 development 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 great relationships, 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 a brand, to add value to your community and to connect with amazing guests throughout 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 start my own business. And so I also met this amazing venture capitalist at 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.
Travis
That's right.
Evan Holiday
And 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 him. Maybe I throw out the idea of the podcast. She's like, yeah, do it. Why not? And 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. He's like, sure, here's my card. Here's my personal cell phone number. Let's. Let's catch up, and let's do it. And literally, 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 it was like the next 30 days was, like a crash course. I was taking, like, John Lee Dumas's, you know, podcast paradise, 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, I was like, hey, I'm not gonna 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. Like, yeah, one of those things.
Travis
You jump off the cliff and build the plane on the way down sometimes. Yeah, yeah, that. That is one of the biggest reasons I encourage people to podcast. It's just the excuse. Yeah, sometimes 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 podcast conversation is a much better excuse than, say, a sales call. You know, like, people. How many. How many LinkedIn DMS do you get on a monthly basis of somebody?
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Travis
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Travis
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 got to create content. If you're an entrepreneur, right, you need more authority and credibility. If you're an entrepreneur, you want more SEO and backlinks. If you're an entrepreneur, like all 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 are building similar businesses, maybe you live in similar places or you may be in the same state or something. You know what I mean? Like, it's just the, it's the springboard to be able to have the excuse to continue, you know, having conversations with people who are up to really cool things in the world, which I think is one of the most underrated parts of actually having the podc.
Evan Holiday
Yeah, I could not agree more. That's what I preach too, 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 holiday ventures.
Travis
Yeah. So tell me about holiday ventures. When did you launch this? What has been the run rate so far? You know, what are you proud about? What is. What's been scary to you?
Evan Holiday
Yeah, we. I say we. My wife and I started the business seven years ago. It was literally just us bootstrapping 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 1200 units in the last seven years.
Travis
And is it like a similar model with like manufactured homes type of a thing or what? Tell me what.
Evan Holiday
No, no, we build stick frame construction. So on site we'd like to get into modular. 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 developed affordably priced communities where we incorporate sustainability placemaking such as like retail or community centers. 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 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 1200 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 and creating long term legacy and impact.
Travis
Have you heard of boxabl? Yeah, Maybe I should make an intro sometime. They're out here in Vegas. Juliano is a friend of mine, but they are. It's crazy. When you go to their manufacturing facility, it's like, I don't know, 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. That's amazing one bedroom homes. I've toured a couple of them. I was like, this is actually. This is actually pretty nice.
Evan Holiday
I see why Elon lived out of this for a while.
Travis
Yeah, exactly, exactly. Well, listen, dude, I appreciate you taking the time to come on the show and share a little bit. I love, love the story, love the scrappiness at each part of the story. From getting the initial, how do I get my foot in the door? I don't even know. Like, 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 got a great opportunity to go work for 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 to have it turn into what it's turned into today. Plus the podcast, everything else you're working on, man, just, just love everything that you're doing. I appreciate you for taking the time. I know you're a busy guy, so where can people go to get more from Evan and Holiday Ventures?
Evan Holiday
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
Travis
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. Like holla and day. Go check out some of the stuff that he's working on. You'll not regret that. Everybody else listening. 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 Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.
Episode: Interview | Make Money Building Affordable Housing with Evan Holladay
Date: March 3, 2026
Host: Travis Chappell
Guest: Evan Holladay, CEO, Holiday Ventures
This episode features an in-depth conversation with Evan Holladay, a real estate developer and investor specializing in affordable and mixed-income multifamily communities. Evan shares his journey from aspiring doctor to founder of Holiday Ventures, discusses the unique challenges and importance of affordable housing, and breaks down the practical strategies and mindset shifts that guided his career. The episode focuses on the intersection of purpose, opportunity, learning, and relationship-building as driving forces behind financial and social success.
"I took my first Bio and my first chem class in college, freshman year. And I was like, man, this shit sucks. What am I doing?...I can't do this for another 10 or 12 years, dude." – Evan (01:18–02:17)
"A bank will actually loan you a quarter of a million dollars as an 18 year old with zero credit history. Blows my mind..." – Travis (03:27–03:57)
"Imagine if people used that $250 grand to buy a house and were taught how to invest in real estate at 18..." – Evan (03:57)
"You're changing that whole family trajectory through housing as the foundation." – Evan (06:59)
"No joke, I nailed the putt. And I was like, what? ...by the end of it, they're like, all right, fine, we'll give you a job." – Evan (08:24–08:55)
"Opportunity comes from people, value comes from competence." – Travis (09:26) "Your what will exponentially increase if you get around the right who." – Travis (14:15)
"...Combining that not being afraid of rejection plus persistence and not being willing to give up until you get what you want or you get a yes." – Evan (16:42)
"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 anyway..." – Evan (19:30)
“I consider that...my personal MBA and my personal network-building stage and helped us really be successful in launching Holiday Ventures.” – Evan (26:27)
"I want to help people and I want to build stuff that I can do that through affordable housing. And I just dove all in..." – Evan (06:59)
"Professional persistence and pushy persistence. One of them people respect, the other one annoys the hell out of people." – Travis (17:10)
"Opportunity comes from people, value comes from competence." – Travis (09:26) "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..." – Evan (19:30)
"You're changing that whole family trajectory through housing as the foundation." – Evan (06:59)
"Sometimes you just need an excuse to keep the conversation going. And podcast conversation is a much better excuse than, say, a sales call." – Travis (21:56)
Evan’s journey illustrates how willingness to pivot, persistence, relationship-building, and using platforms like podcasting can accelerate career advancement and impact—especially in mission-driven entrepreneurship. The stories and lessons are both inspirational and practical for anyone looking to both make money and make a difference.