From Army to Investor

Brett McCollum (00:00.866)
Welcome back to the show, guys. I’m your host, Brett McCollum, and I’m here today with Sean Woodruff. And today we’re gonna be talking about how Sean was able to transition from the military to becoming a full-time real estate investor. Guys, at Investor Fuel, we help real estate investors, service providers, and real estate entrepreneurs to 5X their businesses to allow them to build the business they’ve always wanted and to allow them to live the life they’ve always dreamed of. Sean, without further ado, man, welcome to the show.

Sean Woodruff (00:29.656)
Thank you for having me on, Mr. Brett.

Brett McCollum (00:31.822)
Yeah, man, I’m excited to talk to you about, I know we’re gonna talk a lot, but we’re gonna really try to focus on, you went from being full, like you were in the military, what branch were you in? You were in the Army. Yeah, so you went from Army to becoming a full-time real estate investor, right? Dude, that’s super cool. Before we kind of get into all the meat and potatoes of everything, tell us a little bit about you. Who are you, where’d you come from? Catch us up to speed, man.

Sean Woodruff (00:47.96)
Yes, sir.

Sean Woodruff (00:59.524)
My name is Sean Woodruff. I’m from Ocala, Florida, representing. I’ve always wanted to join the military, so it was no surprise that this is where I found myself. I spent pretty much most of my young adult life there, eight years. I got married right before I was getting out, hence kind of the reason I got out. wife was like, I’m not getting married when I say get out kind of deal. And I was like, well, sounds like a plan.

She just kind of introduced me to a better way of thinking, better way of life. There’s more for me out there to become someone else other than just a soldier. I’ve done, you I made my my kid childhood dream come true. Now it’s time to make the adult dream come true and chase that. And, you know, so it would lead me to get out. It’s what led me to real estate investing in the first place.

That real mature day, Sean, is time to grow up into something different. And came from the wife. And I’ve been appreciative ever since.

Brett McCollum (02:03.522)
Yeah, love it, So did you join like right out of high school or what was that?

Sean Woodruff (02:10.788)
Yep, signed papers. My dad had to sign off for me at 17 at the time, right out of high school, right after I graduated within like two, maybe three weeks, straight off boot camp.

Brett McCollum (02:15.795)
wow.

Brett McCollum (02:23.266)
Wow, and where’d you go to boot camp?

Sean Woodruff (02:25.675)
I went to Fort Sill, Oklahoma.

Brett McCollum (02:28.002)
Wow, okay, that was fun. Did you have any deployments?

Sean Woodruff (02:29.474)
Home of the artillery.

Sean Woodruff (02:35.458)
No, no, jumped around on any deployments. think I guess that’s one of the things that, for, guess, too little too late, you know, if I have any sort of regret, it’s that, you know, the unit just never got called up for deployment. Anytime they got called up, got canceled, moved back, anything like that. you know, felt like I was kind of wasting away and not doing what it was I wanted. And I think that’s kind of what pushed me to like, okay, along with my wife, like this time to go do.

something else, whatever you’re chasing here is not meant for you. There’s something else out there.

Brett McCollum (03:07.992)
Yeah. Were you stationed at one and one base the whole time or what was that like?

Sean Woodruff (03:13.222)
no, I’ve definitely been around a few places. Fort Sill, Oklahoma, and that’s Fort Sill for basic. I was in Fort Huchuca, Arizona for quite a long time of my career. After that moved over to Camp Blaine and Joint Training Center. After spending some time there, I was a UAV mechanic and crew chief. I switched units. We had a special forces unit right next door to us. And I was like, you know, young.

Sean was like, oh my god, those guys were heroes. I want to be one of those guys Yeah, so, you know, I I asked the for a line item switch like hey, send me over there and got over there, know when got jump qualified like all cool stuff and After just a few years over there, you know, that’s kind of what I know I met the wife and decided there’s something else out there for me got out

Brett McCollum (03:44.94)
the social forces.

Brett McCollum (04:05.486)
You meet your wife, you met her at Fort Benning? Is that what you said?

Sean Woodruff (04:10.006)
No, I actually I met here in Gainesville, Florida. She was going to the University of Florida. We kind of had some mutual friends kind of deal. And that’s how I met her.

Brett McCollum (04:21.73)
Very cool, so you were on leave or something or what?

Sean Woodruff (04:25.476)
Yes, I was just kind of down, know, chilling around in Gainesville, Florida at the time. And just instant click. We never really, she’s from Brazil. I guess we didn’t really plan on falling in love. Yeah, Bungie. Yeah, definitely. Some of the first words I learned in Portuguese. Yeah, never planned on it. I think that just happened very organically. I was like, oh, I’m going show you the US before you have to go back to Brazil.

Brett McCollum (04:38.594)
Bon dia.

Yeah

Brett McCollum (04:45.806)
That’s it.

Sean Woodruff (04:55.108)
ended up catching COVID together and then when we like right, when it started off and caught it ended up, you know, kind of sheltering in place together. Didn’t want to get anyone else sick and just didn’t love. Took care of me, took care of her and yeah, all said and done after that brother. All said and done.

Brett McCollum (05:06.798)
And then you track her. There you go.

That’s it. Or she trapped you rapidly, right? Yeah. All right. That’s it. There you go. I take the wild out of you, right? All right. How did you get in? So you’re in the military eight years. How did get into real estate?

Sean Woodruff (05:14.264)
Yeah, domesticated instantly.

you

Sean Woodruff (05:24.324)
Mm-hmm.

Sean Woodruff (05:29.648)
Um, just got, you know, got tired of, you know, like the, the base housing, um, even one of those like off base housing. I was renting someplace, just, just got tired of that. You know, like I said, I was already kind of mentally gearing up to get out, excuse me, um, a little stuffy today. Um, his wife was like, Oh, a bit of VA loan or something like that. I was telling her about it and she was like, how come you haven’t used it yet? The, the buy a property, invest, you know what I mean? And so that’s exactly what we did. Um, we bought it.

I turned one of the rooms into an Airbnb, standalone Airbnb. It was a little awkward, but got used to it. And then I realized like, oh man, this one room more than pays my mortgage. Like how much good could this do if I did the other two rooms? Airbnb’d out the whole thing. Learned a lot about Airbnb on the way and being a host and how to do down to the decor. And it was phenomenal.

to the point that when I was getting ready to get out, I didn’t worry about not being able to pay my bills at the bare minimum, which allowed me to completely focus down on being a real estate investor. Not that I mean, it was really tough, you had to drive Uber for a while on the sides and during the weekends, I’ll do that. But all in all, went from full-time military to just full-time real estate investor had to get a little side gig. And, but after I realized I was wasting my time,

Brett McCollum (06:56.152)
Like, in.

Sean Woodruff (06:58.286)
Yep, straight in, dive head first.

Brett McCollum (07:01.112)
Yeah, that’s a very military thing for you to do though. Sounds to that track, does that make sense? Yeah, so you start Airbnb-ing, it was your personal home and you turned that into an Airbnb. Where was that at at the time?

Sean Woodruff (07:03.908)
Yeah, if you’re do it, it well.

Sean Woodruff (07:15.644)
That was actually right there in Gainesville, Florida. We were looking around because the idea was that we wanted to turn this into a rental. And it was getting crazy, you we were losing homes for a week and even put an offer in. And we found this one. It was a perfect 3-3. All the bedrooms were like an in-suite bed and bathroom. And it was perfect. Perfect, perfect, perfect. It just, it seemed like God was smacking us in the face, like, is the one for you.

Brett McCollum (07:18.134)
in Gainesville.

Brett McCollum (07:35.266)
Mm-hmm.

Sean Woodruff (07:42.596)
We put in the offer and they immediately accepted it and we kind of had it little strategic like it was right near the interstate but really close to one of the major hospitals that get a lot of traveling nurses. So was definitely a semi-strategic buy when we got it. We we didn’t just predict it that it would do better than we even expected. You know that’s that’s kind of been our bread and butter ever since. Just that one.

Brett McCollum (08:06.06)
Yeah, then, so you said, so you jumped right into that, that’s pretty cool that like a lot of people get, they progress toward Airbnb eventually, right? Like you just jumped right into that, which is cool. And then you made a comment that you were managing Airbnbs. So am I reading that right? That’s for other people?

Sean Woodruff (08:15.257)
Mm-hmm.

Sean Woodruff (08:24.452)
Yes, we started to do co-host managing for a few other people’s Airbnbs. Some people up in Jacksonville that were good friends of mine from the military. They would go on deployment and I’d be like, yeah, man, I got you. Manage theirs, manage some. It was really just a lot of veterans, honestly, that I committed with because it’s just an easy connection we have. After a while, a lot of temporary managing.

Brett McCollum (08:46.798)
Cool. Yeah.

Sean Woodruff (08:54.02)
I got away from managing other people’s Airbnbs realized that there’s a certain level of control I need to make things perfect and to solve issues as quickly as possible that I just can’t get if I’m not the owner of the property. And then made me realize, OK, hey, there’s a million other facets of real estate investing in different ways to do this. OK, how do I get my money up? How do I do this? How do I do this? I want to quadruple my money this year.

It’s time to take the next big leap forward.

Brett McCollum (09:26.382)
Yeah. All right. So how long did that run go for? Like, give or take?

Sean Woodruff (09:32.1)
That run, I think that ran for just over a year. I was managing some of the other companies, AirVees. And when I had enough of those, that’s when I stopped doing the Ubering on my side. Just because that was a killer. I that was a whole bunch of my time that I could realize I I like, I know this time could be spent productively somewhere else. And so about a year and then I kind of, stopped taking those on. I started trying to focus down on other things.

Brett McCollum (09:39.405)
Right.

Brett McCollum (09:47.128)
Mm-hmm.

Brett McCollum (10:01.794)
Yeah, yeah, so we talked a little bit off camera, just kind of like some of the things you got in yourself. So you started that, looked like after like the Airbnb’s going and probably during I would imagine you started really thinking about what else is possible for me. What was next? Like what were you starting to get into? Like what happened next?

Sean Woodruff (10:26.148)
So this next part, guess, like a massive learning curve issue. We started looking at taking classes for tax liens and tax liens investing, know, buying properties at auction for tax deeds and spent a lot of money taking courses there, realized that even with those courses, you we made some mistakes, realized we some money, but it was a money grab. A lot of it was good information.

but we were left wanting at the end of it. And we started going looking at the options, account websites and realized that we don’t have capital to really be bidding. So we went out, talked to a few buddies of mine, created a little company that we got pooled some money together to start investing. Even the money that we could pool together just wasn’t enough for us to win any of these properties at auction. And we were like, okay, well, there’s gotta be a better way.

and we got some piece of advice, that like, go join your local real estate investor. Go look on Facebook, we’ll look on Instagram, type in your city type in real estate investor. And yeah, something popped up, showed up to the morning meetings, after a few times in the morning meetings, talk to some, definitely some very knowledgeable groups that kind of really had their stuff together. And, you know, they helped point us in the right direction and kind of hold the hand a little bit and.

We ended up buying the first flip property. There’s nothing about flipping. It was me managing it for also my two friends who were part of the company at the time. The band split up after that, so it’s just a solo driver here now. yeah, with all of that, the real difficulty came that some family stuff was happening back in Brazil. My wife and I actually had to go to Brazil.

that almost that entire next following year back and forth from US, Brazil, US, Brazil, US, Brazil. So we were kind of really on the fire of how are we going to manage this split and manage the work and get the next deal for back and forth to here in Brazil, here in Brazil. It was a crazy ride on that first one. Even the second one right after that, same thing, still going back and forth between here and Brazil.

Brett McCollum (12:49.762)
Yeah, let me back up a little bit, because I think people need to hear what that was. So you’re managing these Airbnbs, and then something happens, and you’re looking at tax auctions and tax detail. this taking courses, taking lessons, and it just, I imagine that that faucet that you mentioned earlier was just wide open, just trying to consume as much information as you could.

Sean Woodruff (12:51.949)
Yeah.

Sean Woodruff (13:14.468)
you.

Brett McCollum (13:20.038)
What was, because I mean, you were focused heavily on the auction side of things. Was that always the goal to buy the auction to inevitably flip or was it inevitably, what was the, to have another Airbnb? What was the, at the time when you first started looking at that, what was the intention?

Sean Woodruff (13:36.196)
The full intention was to buy that auction, to flip it. was the absolute full intention on me and the other investors. We obviously wanted to get our money back within a certain time frame. So it was to buy the flip. And then we realized that our access to capital was not viable to go do this auction.

That’s just money you have to have in your pocket at all times. So we ran into a very, very common problem. How do I get money for this? I don’t have enough money for this.

Brett McCollum (14:14.848)
Okay, yeah, all right. That’s it. Yeah, so I was just wondering like, okay, so now that we were caught up this feed now, Sean, you know, you got your first house to flip, you know, you probably knocked it out of the park, made a million dollars on it. You know, you were a pro right out of the gate, right?

Sean Woodruff (14:33.444)
Not even in the slightest. not even in the slightest, man. You learn a lot through your failures more than you learn through your wins. I will definitely say that it was not a knock out of the park. It was definitely a big chop down at the knees on that first one. It’s funny that I got the second flip. I bought rehabbed

Brett McCollum (14:35.022)
What it’s almost like I set you up for that.

Sean Woodruff (15:03.172)
sold the second flip long before I even got done with the first one. The first one was just a big hang up. Yeah. I held on that learning lesson for a very long time. I think the Lord just said, hey, Sean, there’s still some more you need to learn here before this fire is done on me.

Brett McCollum (15:08.43)
Yeah.

Brett McCollum (15:22.936)
Yeah, that’s interesting. You know, it’s because I say that to say like, for a lot of people that might be listening that they’re not, you know, they’re on their journey and they’re on, you know, whatever path they’re on. They don’t have anything yet or maybe they do. I don’t know. But the lessons of going through and making those mistakes, the things that you don’t know that you don’t know, know, stuff like that. Going through that is it’s kind of almost like a rite of passage almost, you know.

Sean Woodruff (15:37.657)
Maybe.

Sean Woodruff (15:46.596)
Thank

Sean Woodruff (15:51.811)
Yeah.

Brett McCollum (15:52.878)
But that’s super interesting. So you did that, you got you, and now, mean, what is like today? Like, Sean, what are you doing now? Like, so are you still managing your B &Bs? Are you still, like, what is that world?

Sean Woodruff (16:08.676)
So still, yeah, still doing the Airbnb’s. That’s kind of more of like a side project, like, that pays the bills, it’s the bread and butter. My focus turned to flips. And then it also turned into wholesales, learning how to, the wholesale because, hey, I might not always have capital or access to capital or capital to support my access to capital because money costs money.

How can I use my time efficiently to produce more income and learn how to be a better problem solver? At the end of the day, I started getting into wholesale, you know, realized that being specifically a wholesaler wasn’t quite my forte. But it definitely helped me learn how to talk to people where I was very weak, you know, not very social, grew up an only child, military, just very, everything was very direct. And I didn’t have the…

gift of the gap that slight touch away with people. And that’s something I had to force myself to learn the entire time. But now it’s looking at it. When I approach a subject now, I’m primarily looking to do fix and flips. It’s what I got very good at here recently. Wholesale was just a tool that I use to solve a situation. That’s kind of how I approach it. I got my toolbox together.

Fix and Flip is one of my main tools that I use to solve a problem for the seller. If the seller has a problem at beginning.

Brett McCollum (17:44.034)
Yeah, yeah, let me for again, let me said, there’s a lot that you said there that maybe somebody catch us back it up a little bit. You know, Airbnb pays the bills, the bread and butter, right? And then you said, and then you’ve got your fixed income. Now you’ve got the other tool with wholesaling. The most successful people I’ve talked to, the people that I’ve interviewed, they all have multiple, you know, rods in the fire. You know what mean? They have multiple things that they’ve got going.

Sean Woodruff (17:50.435)
Mm-hmm.

Sean Woodruff (17:56.696)
Yes, sir.

Brett McCollum (18:11.906)
But so everybody has something that’s consistent that they’ve got in the background that’s running. And it sounds like you’ve got some consistency, at least in the Airbnb thing, that allows you to be able to build what you’re building with your fix and flips. now you’ve got the other tool with the wholesale. People hear me say this a lot. When you’re wholesaling, you

cherry pick the best, sell the rest, right? And that’s been, now that you have that tool in your belt, you’ve got, so you’re on this path, man, right? And you can just see it just start, it’s taking its shape and you’ve got consistency in one place, you’re building on it with, you’re just building blocks to success on it. it’s, if you rewind it back and listen to what you said, like people have a path that they,

can watch this and listen to and go, wow, that’s something that speaks to me and I can follow. Maybe it’s not Airbnb or they can look at and say, you these are clear, tangible steps that Sean took and is taking to build, you know, you know, the success journey you’re on. So that’s super cool, man. I’m really proud of you. I think that’s a really a powerful thing that you’ve been able to do. So you’re doing now you’re.

Sean Woodruff (19:08.846)
Good to you.

Sean Woodruff (19:16.718)
Yeah.

Brett McCollum (19:37.518)
I mean, so you’ve got the Airbnb, you’re flipping houses. How are you, I’m curious how you’re doing it, because everybody has a little bit of a unique way that they like when it comes to sourcing their deals. What’s your preferred method today?

Sean Woodruff (19:44.804)
Mm-hmm.

Sean Woodruff (19:50.532)
I got two primary preferred methods, would say, realizing that auctions were not as great as they seem, so people get a little too competitive, start throwing the place out of the water kind of deal. I started looking up first source, that was my free source, was going looking at all the properties that are going to tax the auction or foreclosure auction or have liens on the properties.

And I will pull up those lists and then I will skip trace some numbers and some names. I’ll just get the cold calling. That’s a very effective form of free leads. Not necessarily norm. You run into a lot of issues trying to get a hold of people. Another very successful way is I think a very common one is our paper lead service. And there’s a lot of good paper lead services out there.

And it’s just, it’s nice, you know, I can focus in on a specific area if I wanted to, I can go broad. And they’re quality worn to hot needs. these people actively filled out and they are actively seeking to some degree to wanting to sell their property.

Brett McCollum (20:59.416)
So you say more direct to seller then. Yeah, okay, cool. Yeah, I mean that’s, in my opinion, direct to seller is always the best path, right? But that’s super cool to hear. So you’ve got your direct to seller, you’re doing deals right now, you’re taking this trajectory, steps are moving forward. I guess before we wrap things up, I wanna know,

Sean Woodruff (21:02.402)
Yeah, very direct.

Sean Woodruff (21:12.484)
that request.

Brett McCollum (21:28.974)
For the experience, I mean, you allow yourself, if you’re an experienced, somewhere in the middle, or a beginner, there’s always something that we can learn from each other, right? Maybe share one or two things that like, hey, this is something I went through and I learned that you think might be helpful for our audience.

Sean Woodruff (21:39.224)
Absolutely.

Sean Woodruff (21:47.116)
And.

That is a very loaded question because I’ve learned a thorough information and I know that I still have only scratched the surface of what there is to learn. think the biggest two biggest things. One, that whole mind killer of that all I need capital is absolutely wrong. It is false. And you’re lying to yourself and you don’t even know it.

There’s plenty of people out there. There’s hard money lenders. There’s always a way to get in. And you don’t need hundreds of thousands of millions of dollars to start something like this. That’s very common misconception. then two, so very loaded. It’s gonna be very scary at first because you might be taking on

a lot of death for a project that just seems really daunting. And you don’t know who to turn to, where to turn to. And then at the day, there’s people out there who’ve done this very same thing. They’re out there. And like I I went on Facebook, I found a whole group full of, like, to me, they were real estate geniuses. They knew everything and that they could help. And the last thing they want to see is somebody to fall on their feet when they get out there.

Don’t connect with those people, especially before you make a Like I said, if you don’t know what you don’t know, just that brief interaction of going to meet these people and talking to them might save you from making a very bad decision and also put yourself in a position to make really good decisions. Partner up, whatever it is, ask for coaching. Don’t be afraid to ask for help. Don’t be afraid to ask for advice. Yeah, community, always, always.

Brett McCollum (23:36.748)
Right.

Brett McCollum (23:41.646)
community.

Sean Woodruff (23:45.826)
Your network is directly related to your network. I’m pretty sure you heard that a million one times before. Start networking before you even make a new route if that’s necessary.

Brett McCollum (23:56.398)
Yeah, we’re not meant to do life in isolation, right? We need people around us and, know, especially if you can figure out a way to surround yourself with people that are like-minded like you, you know, that understand the journey you’re on, right? That’s really cool. Super powerful. Well, man, Sean, I appreciate you joining us today on the show. If there’s anything like, any way people wanna be able to maybe get in touch with you, you know, tell us about that. Or if there’s something you’re…

Sean Woodruff (24:00.644)
Not at all.

Sean Woodruff (24:09.124)
Mm-hmm.

Brett McCollum (24:25.378)
you know, something you’re working on you want to talk about or, you know, where should people go to check you out?

Sean Woodruff (24:30.82)
So this is actually a very recent thing. I’ve talked to my wife, Gabriella, about our social media presence. I got to put myself out there because there are people out there that might be trying to start the same journey or on the same journey that you want to connect, you want to talk, you want to ask for advice. I’m always free, I’m always open. That’s the best thing I could give. so right now we’re in the process of expanding.

our social media presence and you can look us up on Instagram, virtuousdeansllc. You can find me there. I can, believe I attached my personal Facebook link to the virtualsdeans slash my Sean Woodruff as well. That’s a good way to get a hold of Yeah. And I will be expanding. So not everything I’ve done so far will be on there, but it will be a good, easy way to reach out for me if someone is looking

Brett McCollum (25:15.118)
Perfect, yeah.

Sean Woodruff (25:26.807)
to make that connection.

Brett McCollum (25:28.686)
Dude, I love it, man. Well, you heard it here, guys. Reach out to Sean if you want to connect and talk with him. He’d be happy to, it sounds like he’s happy to have this conversation. yeah. All right, guys, well thanks again so much for joining us on today’s episode. Make sure to subscribe and learn more about Investor Fuel and we will talk to you guys later on. Take care, everybody.

Sean Woodruff (25:29.86)
Appreciate it.