From Corporate Finance to Real Estate Success | Alan Sestito’s Journey

Alan Sestito (00:00)
I remember we were touring apartments and I came home super excited because I thought we found the one I told my mom I was like hey like I’m probably gonna sign this lease and she put her foot down she said are you dumb like what are you doing the only way you’re moving out of this house is if you go buy something don’t throw your money away on rent or you know just because you want to live with your best friend and this that like I know you’re saving

Dylan Silver (00:30)
Yeah.

Alan Sestito (00:54)
money, you can do this, you can put a 3 % down payment on a house, which isn’t much at this time, and now you can own your own property. Like, what do you think about that? And that really just got the wheels turning. You know, obviously, mom was right. So yeah, I have to give her credit to, you know, me going down this path and thinking about real estate in a different light.

Dylan Silver (01:32)
Hey, folks, welcome back to the show. Today’s guest is a North Carolina based real estate investor and broker with a finance background and has worked in the Build for Rent project space as well as single family home space. Please welcome Alan Sestito. Alan, welcome to the show.

Alan Sestito (01:50)
Thank you so much Dylan, happy to be here.

Dylan Silver (01:52)
It’s great to have you and I think you’ve got an interesting background. We were talking before the show here and what really piqued my interest was you made a pivot. You made a pivot. You decided, you know, after going down one career path in the finance space that you decided I want to do something different.

Alan Sestito (02:08)
Yeah, you know, kind of like we spoke, my main goal professionally was to climb the corporate ladder. Like after college, you know, that’s what I was.

told to do, that’s what I wanted to do. So 2019 is a pivotal year for me because that’s the year where I thought that I landed my dream job in finance. The company, the role, the pay, the benefits, everything, I felt like as a 27-year-old, I made it. This is it. This is the company I’m going to retire at. I would say about two or three months into that role, I knew I made just a terrible mistake.

I was miserable every day. I dreaded going to work. I was working 80, 90 hours a week for something I did not care at all about. And it was just, it was just draining to me. ⁓ Draining, absolutely draining. So I quit without a plan. I wasn’t applying for jobs or anything. I just got to the point where, you know, just parted ways with the company. took some time to kind of self reflect, you know, look at myself in the mirror. And I told myself, you know, the next job that I,

Dylan Silver (02:55)
training.

Alan Sestito (03:12)
I’m

gonna get, I’m gonna truly be passionate about. I didn’t care about the pay, I didn’t care about anything. I’m gonna wake up and enjoy what I do. So that’s really, I’ve always been interested in real estate. I was kinda doing real estate on the side in terms of kinda buying rental properties and house hacking and different little things. And I didn’t realize I can turn that into a full-time job. So I always kinda gravitated towards that. And I had all this time on my hands, so I just went head first into real estate, started reaching out.

to people, kind of growing my network, having coffee with people, shadowing different people in different sectors of real estate, and that’s kind of what led me to the start of my real estate journey.

Dylan Silver (03:52)
I think it’s

an interesting story. And I think a lot of people who are guests on this show and other people who are listening have probably either gone through or thought about doing something. It can be scary, but also people know what’s the risk if I don’t make the move, right? I also want to pivot a bit here and talk about, you mentioned earlier before the podcast that your mom was basically an inspiration telling you, you got to get into the investing side of things. And I’d sometimes say that, you know, it’s not necessarily that

Alan Sestito (04:13)
Yeah.

Yeah.

Dylan Silver (04:20)
the case that people have parents or family or friends that are directly involved in the real estate space. But sometimes people have friends or family that might have like an entrepreneurial bone in their body. It sounds like maybe your mom was an inspiration for you in that regard.

Alan Sestito (05:22)
Yeah, no, shout out to my mom. She’s, you know, she’s always been just unconditional and has supported me for every dumb or good idea that I’ve had. And I have to give her credit.

As I was telling you, when I graduated from college, I moved back in with my parents for about a year. I was fortunate enough to have very little expenses at that time. I had minimal student loans that I paid off very quickly. My parents obviously weren’t charging me rent and they were feeding me. I had a pretty good job out of college at an investment bank. I was just, I was saving up a lot of money. And my goal was to move out as quick as possible.

for my parents house because I was like no I graduated college like I need to start my life so my best friend and I I remember we were touring apartments and I came home super excited because I thought we found the one I told my mom I was like hey like I’m probably gonna sign this lease and she put her foot down she said are you dumb like what are you doing the only way you’re moving out of this house is if you go buy something don’t throw your money away on rent or you know just because you want to live with your best friend and this that like I know you’re saving

Dylan Silver (06:05)
Yeah.

Alan Sestito (06:29)
money, you can do this, you can put a 3 % down payment on a house, which isn’t much at this time, and now you can own your own property. Like, what do you think about that? And that really just got the wheels turning. You know, obviously, mom was right. So yeah, I have to give her credit to, you know, me going down this path and thinking about real estate in a different light.

Dylan Silver (06:49)
Was that

first deal, was it single family? Was it a duplex, triplex? What was that first deal like?

Alan Sestito (06:53)
No.

It was just a town home. was a three bedroom town home. so this was back in 2013 and I had a bunch of buddies that graduated from college that moved to Raleigh and like they were looking for places too. So as I was kind of going through the process, I was also kind of prospecting potential roommates cause I didn’t want to pay, you know, a full mortgage on my own, on my entry level salary. So I immediately got to my good buddies to say, like if you buy this house, like I’ll move in with you and like we can split rent.

So essentially I was still living rent free and doing the whole house hacking before that kind of got commercialized and people just kind of caught on to that method of real estate.

Dylan Silver (07:32)
So did you have

any kind of mentorship at this point in time? Was your mom in your ear telling you, hey, do this, do this? Were you reading? Were you listening to shows online? Where was the guidance coming from at that point?

Alan Sestito (07:43)
So, you know, the first shove was mom, so I’ll give her the credit. And from there, just like something just kind of clicked. And I was like, wait, I need to do more research on this. you know, like everybody else went to YouTube University, started Googling different things, started looking at, you know, different financial models and like how to analyze a single family rental home and you know, what it takes to

you know, get qualified for loans and different financial products that are specifically for real estate investment. So that was just, that was just so eye, eye opening. And from there, like, like I said, you know, just really tried to grow my network of people who were doing it. I was obviously very green to it, very new to it. So I started reaching out to people who I knew owned multiple properties or are developing real estate or anything in real estate, just to kind of be a sponge and just soak in.

as much knowledge as possible. Yeah, I I just turned 23 years old. ⁓

Dylan Silver (08:34)
How old were you when you got that first deal? That first pound home?

Wow.

Alan Sestito (08:42)
So yeah, my realtor at the time was like when we first met, she was shocked because I had such a baby face. My closing attorney was just like, man, you’re ahead of the game. Like you have no idea. I didn’t know what I was doing. I was just super pumped to not live with my parents anymore. like, I wish I can tell you I had it planned out, but I didn’t.

Dylan Silver (09:36)
You

know, I think it’s an interesting story because it could have been I started renting, right? And then I didn’t even think about the townhome. Then now that was the sort of spark that lit the fire. I want to pivot a bit here and talk about what it’s like as a real estate guy or someone who’s passionate about real estate on some level in the finance space. Was that very common? Were there a lot of people?

in the workplaces that you’d been in who were chopping it up about real estate and talking about different deals that they might be looking at? Or was that really a separate world?

Alan Sestito (10:04)
Yeah, no, is very, it is very mangled. You know, as somebody who’s interested in finance and a numbers guy.

like real estate is that language. You know, it’s a very numbers based, you you back into a cap rate or you back into evaluation of a home to see what your cash flow is or what your ROI is. So it’s the same language as finance. So I had a lot of colleagues who were doing something similar to what I was doing. They were, you know, they’re buying properties on the side and they’re like, hey, you know, if I can buy one property a year, you know, one property every two years and rent them out, you know, by the time I’m ready to retire,

hire at 60, I might have 10 or 15 rental properties and that’s my retirement plan. So that was always our mindset. It’s work this nine to five, climb this corporate ladder, take some of your savings, throw it into this real estate investment. Pray it works. Pray you know that you’re, you think that you know what you’re doing. and then maybe, you know, after 35 years of service, you might have a nice little nest egg in terms of, of real estate, but, it was really just, you know, throwing mud out, mud at a wall and seeing if it sticks.

Dylan Silver (10:56)
you

Let’s do it,

snakes. Once you got licensed, you mentioned the career pivot that you made 2019. What was that first year, year and a half like? Was it an easy transition? Were you kind of very gung-ho, hey, I’m going to sell a bunch of homes? Were you really focused? You mentioned coffee networking. What was that first year like for you?

Alan Sestito (11:09)
Yeah.

⁓ that first year was a roller coaster. but it was, it was such an impactful year for me cause I had this fire back. had this hunger back. Like I had just gone through, you know, it’s similar to going through a breakup. You’re just like, man, I was almost, I was down in the dumps. didn’t know. Like, like, did I do something wrong? Like what’s going on? So I was questioning myself. My confidence was low. but then like it really snapped. It’s like, all right, Alan, if you’re going to do this real estate thing,

Dylan Silver (11:40)
Yeah.

Alan Sestito (11:53)
you’re gonna go all in. like as somebody who played sports growing up, I was such a competitor and that really just got my juices flowing. Obviously there’s a big learning curve for me because I had never professionally worked in real estate. You know, I knew I had the knowledge but there’s still such a learning curve in order to get sped up and really, you know, be viewed as somebody who understands real estate and a professional in real estate.

Dylan Silver (12:19)
I want to ask

you a couple of granular questions about North Carolina and then also your business out there. So when you were scaling and getting your first deals, was there an asset class or a type of buyer that you and seller you wanted to work with? Were you looking at all different types of deals or were you thinking, hey, I’m going to start with, let’s say, single family homes and then maybe look for working with investors and so on and so forth?

Alan Sestito (12:22)
Yeah. Yeah.

Yeah, no, that’s a great question. I…

I had always had an interest in residential real estate. I understood it. had some experience in investing in it. So I was fortunate enough when I moved to Charlotte, ⁓ I linked up with a mentor of mine who had just launched his own brokerage company here in Charlotte. And it was a very specialized brokerage. ⁓ It focused on the sale of single family rental portfolios. So think of somebody like me or somebody who a mom and pop investor who’s a

10, 15, 20, 30 homes, rental homes, and they’re looking to sell it off. We would broker that to institutional funds. So equity groups, large SFR operators who are raising hundreds of millions of dollars to buy homes in bulk for rental purposes. So that was one vertical. And then just a natural spin-off from single-family rentals, those same institutional buyers were now buying

Dylan Silver (13:24)
Yeah.

Alan Sestito (13:41)
I

what they were doing to my own personal investments and development. So I have to give a lot of credit to, know, Strata SFRs is where I started and where I really got into the residential real estate game ⁓ from an investment standpoint.
Alan Sestito (00:00)
so the brokerage firm that I linked up with here in Charlotte, North Carolina was a very specialized

brokerage firm. So they ⁓ specialized in the sale of bill to rent communities and single family rental portfolios. So for the majority of my time there, I was representing sellers and kind of navigating them through the process because not a lot of people, you know, understand the process of institutional buyers and institutional funds and kind of what they’re looking for and their underwriting criteria. So that was that was a great time for me. Spent four and a half years there, you know, transacted on hundreds of millions of dollars there.

big transaction so really got my confidence in the real estate investing board there.

Dylan Silver (00:40)
I want

to pivot a bit here and ask you about your perspective on investing regionally in North Carolina specifically where you’re based out of.

talking about how great it is for families, how there’s lots of different emerging markets out there that there’s some areas which are going to be more cost effective and then there’s other areas which are

maybe a little bit less cost effective, but such great areas that they’re great investments nonetheless. I’m curious to get your perspective on investing out there in North Carolina.

Alan Sestito (01:08)
Yeah, think, and what confirmed this for me, I’m obviously pro-Carolinas in terms of residential investing. And I think what really solidified that for me was listening to these institutional funds and seeing what their buy box was. them saying, hey, we raised $50 million to deploy strictly in the Carolinas, strictly in Charlotte, strictly in the Raleigh-Durham area.

And, you know, if Wall Street is betting their money on the Carolinas and the real estate.

something’s got to give, right? It’s definitely a great place. It’s cost effective, low cost to live. It’s very business friendly. So a lot of businesses are moving into the Carolinas. People from up north and out west where the prices are just through the roof are sick and tired of that. And they’re selling their two bedroom house for 2 million bucks. And you can get such a nice piece of land here in a nice,

Dylan Silver (01:40)
Right.

Alan Sestito (02:06)
nice house in a great community in a great area in the Carolinas. So I think we’re going to continue to see that. Prices have been going up, but if you take a step back from the macro level, they’re nowhere near, you know, the new world, the Chicago’s of the world, the LA’s of the world, the Miami’s of the world. So I think we’re trending in the right direction.

Dylan Silver (02:20)
some of these others.

I want to ask you a granular question about maybe some investment strategies that you’re looking at or that you have seen in the past that have been successful. Some of the things that I’ve participated in and I like are short-term rentals. also like land deals, storage facilities, RV parks, that type of thing. But then there’s risks with each of those. And with short-term rentals in particular, they could go away. You might not be able to do a less than 30-day stay.

I’m a big fan, you mentioned house hacking earlier, I’m a big fan especially for younger investors of that type of investing, know, quadplex, triplex, duplex. What have you seen that maybe works great, especially for someone who might just be starting out?

Alan Sestito (03:07)
Yeah, I think, kind of like you said,

My story was house hacking that got my foot into the real estate door. know, over time, people are paying your mortgage for you. And at that time, you know, equity should be building up in that house. So that’s a great foundation to have. I think one of the lowest barriers to entry in real estate would be wholesaling deals. You don’t license, you just need to have an ability

Dylan Silver (03:32)
Yeah.

Alan Sestito (03:36)
to understand and put deals under contract. You gotta be personal with people. You gotta find off-market deals and generate leads. So I think if you can kind of master those skills in wholesale, can eventually develop, or transition into maybe being a broker or being a principal in your own deals. But I think those are probably the two best ways to get your foot in the door in terms of real estate investment.

Dylan Silver (04:03)
I want to ask you about your brokerage and how that’s been going and then also what it’s been like really scaling your own business. How has creating a brokerage gone for you and is there a specific focus that you have day to day in your business?

Alan Sestito (04:17)
Yeah, so it’s been fun.

We launched this year, I’m kind of wearing a lot of hats in terms of getting brand recognition and operations, but at the same time, still managing deals. So we’re a land acquisition and brokerage firm. So we just launched our development arm of our business. So we’re acquiring land, partnering with builders and delivering new construction homes, either rental homes or for sale homes, just depending on the market.

And we’re really focused in high-growth neighborhoods of Charlotte, North Carolina right now I don’t want to stray too far away because this is the market I know this is the market I’ve been in for the past, you know five or six years So I understand it very well. So hopefully, you know kind of when we get a process down we can expand but right now focusing on developments in Charlotte and then the other side of our business is our land brokerage so sourcing anything from raw land

to entitled land, to finished lots, and brokering those to home builders, either large national home builders or regional home builders or build-to-rent home builders. So there’s a large pool of buyers who are looking to, you know, kind of increase their land position here in Charlotte. Yeah. You want a job?

Dylan Silver (05:32)
I’m a big fan of all of that, specifically the land deals. Primarily,

yeah, maybe let me look at them, primarily because being a former Texas resident, there’s so much of that. And it’s also addressing in a lot of ways the housing crisis really, because with some of the alternative housing, you’ve got RV parks, modular, know, offsite stick built homes, this type of thing, it’s going to become, I’d say increasingly more important with time.

But Alan, are coming up on time here. Where can folks go if they’d like to reach out to you? If maybe they have a deal in North Carolina that they’d like you to take a look at.

Alan Sestito (06:08)
Yeah, absolutely. So on Instagram, ses underscore residential. And then you can email me at Alan, A-L-A-N, at sesresidential.com. Feel free to look me up on LinkedIn as well. And yeah, looking forward to connecting, continuing to connect with as many people as possible, because that’s the name of the game, as we all know.

Dylan Silver (06:31)
Alan, thank you so much for coming on the show here today.

Alan Sestito (06:33)
Appreciate it, Thank you.