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Jake & Gino: Real Estate Investing & Multifamily

From Zero to $694M in Real Estate Development | Evan Holladay

Jake & Gino: Real Estate Investing & Multifamily

Jake & Gino

Smartinvesting, Buyingrealestate, Investing, Multifamilyrealestateinvesting, Business, Investingsmart, Apartmentinvesting, Management, Makingmoney, Realestateinvesting, Cashflow, Jakeandgino, Realestateinvestment, Commercialrealestateinvesting, Buyingapartmentbuildings, Entrepreneurship

4.9842 Ratings

🗓️ 9 March 2026

⏱️ 49 minutes

🧾️ Download transcript

Summary

How Evan Holladay Built $694M in Real Estate Development In this episode of the Jake & Gino Podcast, hosts Jake Stenziano and Gino Barbaro sit down with real estate developer and investor Evan Holladay. Evan has led over $694 million in real estate development projects and more than 2,600 multifamily units. As the Founder and CEO of Holladay Ventures, he focuses on workforce, affordable, and mixed-income housing developments across the United States. In this conversation, Evan shares his journey into real estate development, the challenges of breaking into the industry, and the key lessons he learned while scaling large projects. He also explains how aspiring developers can get started, what it really takes to succeed in this space, and how real estate development can become a powerful path to building long-term wealth. Beyond development, Evan is passionate about mentorship and education. Through programs like Affordable Development Mastery, he helps guide the next generation of real estate developers looking to enter the affordable housing space.

Transcript

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0:00.0

Hi everybody. It's Jake Sanzano. I'm hosting Jake Dino podcast here with my co-host,

0:02.9

the multi-family mentor, the coach, Chef, Father Six, the best line off there. The Giddi! Gino 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, okay, brother.

0:19.0

I've been a little cold, fair enough.

0:27.6

All right, we have a very special guest.

0:34.1

Today's guest is a real estate developer, an investor who has led over 694 million in projects and 2,600 multifamily units.

0:38.5

As founder and CEO of Holiday Ventures,

0:40.9

he specializes in workforce, affordable,

0:43.5

and mixed income housing.

0:44.9

That's the new engine.

0:45.4

I don't even know what mixed income housing is.

0:47.7

I think I'm about to find out.

0:49.0

He also mentors developers through affordable development mastery

0:53.0

and real estate developer academy. So without further ado,

0:57.2

Evan Holiday, welcome the show. Yes. Thank you for having me, guys, and good to see you again.

1:01.8

It's our pleasure. Dude, I feel like it's been like 20 years. It's been a long time, like 10 years maybe,

1:07.3

probably about 10 years. So what are you working on these days? Yeah, we're we're growing the company and growing the deals we're doing and and also teaching other people how to do it like you mentioned with with ADM. But yeah, life is good, man. We're working on affordable developments across Nashville. We're expanding to new markets throughout the southeast and up in Ohio and Columbus. And yeah, just trying to, you know, chip away at the apple of solving the housing crisis.

1:32.2

So, Evan, you know, when people are born, they grow up, they aspire to become police officers,

1:38.8

firefighters, Jake wanted to work at Radio Shack, he became a pharmaceutical rep.

1:43.2

How did you decide and say to yourself,

1:45.4

I want to get into the affordable housing and deal with the cities and build this housing.

1:51.2

This is what I really want to do. And all this stuff, right? It's like, which is worse? The cities are

1:55.0

HUD. Oh, 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 the space? Well, if you could all these problems, you can probably do pretty well because no one wants to deal with this stuff. Yeah, because we started coming up around the same time. Like, Jake and I started buying multifamily. and I think you were starting to buy it, but then you made the pivot.

...

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