Navigating the Affordable Housing Landscape
Jake & Gino: Real Estate Investing & Multifamily
Jake & Gino
4.9 • 842 Ratings
🗓️ 2 March 2026
⏱️ 43 minutes
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| 0:00.0 | Hello, everybody. It's Jake Sanzano. I'm hosting Jake Dino podcast here with my co-host, the multi-family mentor, the coach, Chef, Father Stakes the best line off there. Hey, Jino Barber, how's it going? Jake, I'm doing good, brother. How are you doing this morning? Come on, man. Talk some shit. Not yet. Let me get a little warmed up. Let the engine get revved up a little bit. Then we'll start flinging the arrows. Been a little cold. Fair enough. |
| 0:26.7 | All right. |
| 0:27.9 | We have a very special guest. |
| 0:33.7 | Today's guest is a real estate developer, an investor who has led over 694 million in projects and 2,600 multifamily units. As founder and CEO of Holiday Ventures, |
| 0:40.7 | he specializes in workforce, affordable, and mixed income housing. That's the new one. |
| 0:45.1 | Gene. I don't even know what mixed income housing is. I think I'm about to find out. |
| 0:48.6 | He also mentors developers through affordable development mastery and real estate developer academy. So without further ado, Evan Holiday, welcome the show. Yes, thank you for having me, guys, and good to see you again. It's our pleasure. Dude, I feel like it's been like 20 years. It's been a long time, man. Like 10 years, maybe. Probably about 10 years. So what are you working on these days? Yeah, we're growing the company and growing the deals we're doing |
| 1:11.7 | and also teaching other people how to do it like you mentioned with ADM. |
| 1:15.8 | But yeah, life is good, man. |
| 1:17.0 | We're working on affordable developments across Nashville. |
| 1:20.4 | We're expanding to new markets throughout the southeast and up in Ohio and Columbus. |
| 1:24.9 | And yeah, just trying to chip away at the apple of solving the housing crisis. |
| 1:28.9 | So Evan, you know, when people are born, they grow up, they aspire to become police officers, |
| 1:34.7 | firefighters, Jake wanted to work at Radio Shack. He became a pharmaceutical rep. |
| 1:38.5 | How did you decide and say to yourself, I want to get into the affordable housing and deal with the cities and build this housing. This is what I really want to do. And all this stuff, right? It's like, which is worse? The cities are HUD? Man, yeah, don't get me started. So many war stories of just massive brain damage trying to get deals done. But yeah, what made you want to get into it, though? Like, what made you want to get into it though like what made you |
| 2:00.9 | want to get into the space well if you solve these problems you can probably do pretty well because |
| 2:04.3 | no one wants to deal with this stuff right because we started we started coming up around the same time |
| 2:09.8 | like jake and i started buying multifamily and i think you were starting to buy it but then you made |
| 2:13.6 | the pivot and i was thinking to myself wow this guy's got to be courageous to do this. He's got balls, man. Yeah, it's a long time horizon. There's a lot of, there's a lot of detail to it. There's a lot of risk because the timeline is so much longer, especially when you're newer, you don't have any kind of experience. What made you go down that road? Yeah. Yeah, great question. Yeah, I mean, when I went to school, I thought I wanted to be a doctor. And so, you know, you got to look like the shirt and not quite as glamorous as Radio Shack, but, you know, but no, I really wanted to be a doctor and I wanted to help people and I wanted, I thought medicine was my path. And then I went down and took a chemistry class and realized, I hate this shit, and I don't want to do anything like this. |
| 2:55.0 | But I figured out, I was like, I wanted to help people through my work, and I wanted to make good money. |
| 2:59.2 | How could I do both of those together? |
| 3:01.1 | And at the same time, I saw the student housing development. |
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