From Law to Property: 5 Key Lessons with Alaskan Investor Rolland Wimberley

Dylan Silver (00:00.534)
Hey folks, welcome back to the show. I’m your host Dylan Silver. And on today’s episode, we have Rolland Wimberley. Rolland is a Alaskan attorney and currently at 48 doors on a personal as a real estate investor. Rolland , welcome to the show.

Rolland Wimberley (00:19.974)
Thank you for having me on, Dylan. Yeah.

Dylan Silver (00:23.404)
Let’s start at the top. How did you get into the real estate space?

Rolland Wimberley (00:23.879)
So.

Rolland Wimberley (00:29.682)
So my journey started back when I was just 19. I bought my first house after a year in college and that was just basically as kind of a house hacking. So I bought a hundred year old farmhouse in Missouri where I was going to college and rented out rooms to a couple buddies of mine and it’s kind of grown from there.

Dylan Silver (00:58.296)
So, house hacking is an interesting one because I think people think about needing lots and lots of money to get into the real estate space. But in actuality, if you are going to be purchasing real estate for yourself and then you realize, well, let me have some roommates, let me have some housemates, they end up coming with you. You eventually get a nest egg, you find the renter to replace yourself and then you kind of rinse and repeat. I’ve heard people doing this multiple times, scaling it up.

to the point where they’re like, wow, know, I wasn’t thinking that I was gonna be a landlord, but here I am with three of these deals, now I’m a landlord, and now I have two rental properties in my homestead. Was it a similar deal for you, or was it after the first couple roommates, you were like, there’s something here?

Rolland Wimberley (01:44.274)
No, well, I’m a pretty social person to begin with and so when I and you’re right It does take a little bit of a nest egg a little bit of you know, some some barrier to entry to get that deposit down first Luckily for me I was doing it a little over a decade ago So right in the Midwest too, so where where prices are a little less expensive Especially back in you know, 2010

But I was, yes, right? Perfect timing for me to actually like jump in, that being purely out of luck. But deciding that I was gonna go to school for, you know, four years at least at this school. so I needed somewhere to live and I might as well be putting it toward a mortgage instead of just paying off somebody else’s mortgage rent, especially when I can get a

Dylan Silver (02:22.936)
Really? Yeah, it was.

Rolland Wimberley (02:43.757)
a decent size bigger place and you know had a couple of rooms and so some buddies of mine could you know rent in and cut down on costs you know for me personally as well as you know as I was also going to school and doing sports and in a fraternity and everything else so I had you know a friend base and stuff that I could get people to join me on but also I was doing a bunch of other things so I couldn’t

necessarily work after school, so it was a way for me to pay out of state tuition while also, you know, not coming up completely short or taking out a bunch of student loans.

Dylan Silver (03:27.406)
So at this point in time, you’re house hacking, you’re going through school. Were you acutely aware, hey, there’s a future here for me as a real estate investor in addition to any career path that I may go down? I don’t know if at that point in time you had it hard set in your head, I’m gonna be an attorney. Or are you thinking, well, this is cool, I’m able to kind of offset my overhead here by having roommates and let’s see where this goes.

Rolland Wimberley (03:50.744)
It was definitely the sec the latter of the two I was just doing it to cut down on housing expenses and Everything else while paying tuition You know, we all split the bills. We all do everything just as you would in an apartment or anything else But it was at least paying paying on my mortgage So was cutting it down and I knew you know if if I just gave up on it afterwards I could always you know, sell the house after I graduate and put that money toward

my future forever home or whatever, but it kind of, so I didn’t go into it planning on multiplying and building up, but that is certainly what happened after I graduated and everything. So it’s kind of from there, but I’ve always been pretty minimalistic on my own needs and wants for housing. So I’ve always basically been fine having a roommate, having,

somebody to split bills with, know, buying something and then renting out another room to somebody. And then that way you get to pick your roommate. You get to pick your tenant, your person living with you as well.

Dylan Silver (05:01.966)
Did you go straight from college to law school?

Rolland Wimberley (05:05.233)
I did take a year off. came back to Alaska and was working. My parents own a small family business and everything, which is what brought me back here. I’m a big component of traveling and everything. So most of me being a lawyer has actually been in Guam. I was an attorney and a prosecutor out there. being out on a tropical island,

Dylan Silver (05:19.17)
Okay.

Dylan Silver (05:22.819)
Yeah.

Dylan Silver (05:28.856)
Mmm.

Rolland Wimberley (05:35.054)
and being working for the local government out there. But I’ve had to put kind of long. Yep, nope, nope, it is. It’s one of one of our five U.S. territories. out there in the South Pacific, you know, kind of twice as far from from us as Hawaii down there by the Philippines and by, you know, Bali and Thailand, that that area.

Dylan Silver (05:40.556)
Is that a US territory? I’m ignorant of this.

Okay.

Dylan Silver (06:04.322)
Okay, so let me see if I’ve got them. We’ve got Puerto Rico, US Virgin Islands, Guam. That’s all I’ve got. What are the other two?

Rolland Wimberley (06:11.697)
You got American Samoa and you’ve got the Northern Marianas Islands.

Dylan Silver (06:17.682)
Okay. Okay, I don’t even know about the Northern Mariana Islands, so I got to look this up later on. I’m a big traveler as well. I love to go abroad. I lived in Australia for a better part of a year in Melbourne. I’ve been to the Dominican Republic, Santo Domingo, quite often in the last year. That’s how I picked up Spanish. But…

Rolland Wimberley (06:19.737)
Yep. So those are.

Rolland Wimberley (06:41.979)
Nice.

Dylan Silver (06:43.502)
What I what I’m curious about is you have this the year of time right at this point you’re probably thinking what’s the future going to look like I have my degree family business. I’m in Alaska right. Where am I going with this. So I’m imagining there was a point where you’re like OK I’m going to go be an attorney at this point to probably real estate wasn’t in the forefront of your mind or am I wrong. Were you thinking I’m going to go do real estate and I’m to go be an attorney and let’s let’s do both.

Rolland Wimberley (07:11.921)
Kind of a bit of both. didn’t, I picked up some rentals and stuff. I started an LLC doing some expansion from my family business with my parents. We invested and got a small office building here in Alaska. So doing more commercial real estate. We’ve had some single family home rentals here in Alaska.

But actually my journey in fully diving in didn’t start until the pandemic happened. I was out in Guam during the pandemic when everything shut down. And I decided, you know, especially to jump into learning about a lot of this, you know, trying to, because I had a lot more time and there are certainly worse places to be, you know, stuck in quarantine than a tropical island. But

reading a lot more, doing a lot of pod, like listening to a lot of podcasts, learning a bunch. And then from there, I started expanding out my properties because because I was stuck on an island, I had to do a lot more in building a team and learning the development of long distance real estate. So having a contractor, an agent, a property manager and being able to do all that while still holding down.

your nine to five government job.

Dylan Silver (08:43.886)
So at this point in time, prosecutor and Guam have processes in place and people in place to oversee these properties remotely. Are you day to day checking in on these properties and heavily involved or do you have people on the ground there and it’s more of a every, let’s call it once a week type touch base to see how things are going?

Rolland Wimberley (09:07.873)
It’s more that second. I don’t have near the time to do day to day. And pretty much all of my properties are long term rentals. So I’ve got people there to handle if the toilet breaks or something like that. That’s what everybody says is their number one concern at 2 in the morning. I don’t have to go out with a plunger or deal with

you know, water heater breaking or anything like that, we’ve got processes and people in place that if those phone calls come out, they don’t call me because even if they call me, I’m thousands of miles away, I can’t do anything about it. So I’ve got to have people who can and people that I trust who can and we’ll pick up the phone.

Dylan Silver (10:00.472)
You know this is an interesting discussion I said this before on another podcast that I’ve had a remote real estate rights of my ambition is I’d love to live in an area outside the US right I would love to be in a place maybe speak another language but I’ve had mixed feedback from people a full disclosure you know I don’t have any deeds in my name yet or a company that I own but one day I’d like to hopefully here soon and.

The feedback that I get is two categories. Number one is if you’re doing everything yourself and that’s what you’ve been doing, you can’t just move abroad, put someone else in place and figure it out because the systems and the people are everything. And so if you if you’re going to do that, you really have to have the system down while you’re here. Make sure that everything is going going well. Then you can go abroad and still things might might might break. I’ve also had other people tell me, you know, I don’t really see

most people being able to do it. It’s kind of an outlier, but you’re doing it and you were doing it. And so what is your general rule of thumb and feedback for people who are wanting to do real estate and manage real estate remotely, whether it’s long term rental, short term, even fix and flip. What’s your feedback?

Rolland Wimberley (11:16.805)
would say, I mean, the best thing to do would be to get involved. mean, even if you’re, you need to know the area. So you need to have some connection to it. I’m sure there’s some people who can just, I’ve never stepped foot in, you know, Ohio or something, and I’m gonna buy a bunch of houses there and rent them out and flip them or, you know, anything. That’s not really for me.

I at least know the area of Missouri that I’ve invested in because I went to college there, I’ve lived there, I know the, at least the area I connected with people while I was there. So I have connections and a base and friends and a team that I trust and can connect with that they can handle that. And so I know that if I’m in Guam or if I’m traveling or I’m even

just home in Alaska that if there’s a real problem, they can contact me and everything. But they are able to handle anything below a six type of thing on the scale. And then let me know about it after the fact. Hey, this came up. This is how we dealt with it. And then are you OK with that? If this kind of thing happens again, was that all right? Or how should we proceed?

proceed differently, but really being able to trust the people that you have in place. And whether that’s you just hire a third party company that you’ve not dealt with, but you at least, or haven’t dealt with personally or met personally, but can back, look into their background, check up on things and be like, okay, well, we’ll see if this is a fit, but really needing to know how you fit together and can trust them so that you can.

go out and explore or have a day job or not be there on site, you know, even once a week. I mean, there are several properties down in Missouri that I’ve bought sight unseen. And for better or worse, some have popped up with a couple of different things that we didn’t notice at the time. But I have a contractor that walks through the property beforehand before I buy it. I’ve got an agent that, you know,

Rolland Wimberley (13:42.13)
I trust and can, you know, that’ll look through things and she’ll send me different listings or ideas and, you know, are we looking at this? What are we going for? And just kind of like that. So it’s really building those relationships and building that team and then being able to expand from that so that you’re not working day in and day out because I have two jobs now.

My parents have a grocery store, but my dad is 76 years old and was set to retire. So I put law on the back burner at the moment and I came up here to help him retire and run the family business. And then since then, we bought a bar restaurant.

because my brother, who moved up here a couple years after I did, is a professional chef. So he runs the restaurant side of things, I run the bar side of things, and we’ve kind of grown into that in our small little island town. But I’m a man of many hats at this point.

Dylan Silver (14:54.03)
This is so interesting. I hope you don’t mind me interrupting for a moment. Yeah, because one of the things, and I’ve said this now several times, and I’ll say it again here, real estate investors, high level operators like yourself, Rolland, tend to have what I call a fair degree of neuroplasticity in what they do day to day. Like a lot of people, if you just take them out of their routine, it’s like a shock to your system. Like you can’t…

I’ve seen this many, many times, like just a lack of structure in a sense, go from one thing to something totally unrelated. There could even be a structure, but just different. And it throws people off. And like, I can’t do this. And what I’ve seen with real estate entrepreneurs is they will adapt based on the market. In my purview, I’ve seen or my field of view, I’ve seen

Wholesalers go to fix and flipping go to short-term midterm long-term rental go to commercial and I’ve even seen people and I’ve had them on the show build hospitals, which is amazing right that you could start from Cold-call and you know for foreclosures for lack of a better term to then something of that grand scale or or nearly there And in hearing your story, it’s different but it’s still talking about Change and adapting to the change and then seizing that change

And so when I think of like what really, and I’ve been doing these interviews now for a couple weeks, what really makes a good real estate entrepreneur is ability to adapt mentally to changes in markets and then also changes in lifestyle and problem solving, right? So like talking about, you know, don’t bring these issues to me unless they’re a six, then I’ll adjust, I’ll be able to talk about this, but having those people in place. And so you’re talking about restaurants.

grocery store, know, brother is a chef, so managing the family business, pivoting out from being an attorney, like, you’re a prime example of this.

Rolland Wimberley (16:55.281)
Well, and thank you. Yeah, that’s that’s absolutely it. mean and you talked about it depending on the problem and everything I mean, that’s that’s all our jobs are anybody’s job is like what problem do you solve and the bigger the problem or anything else, you know the more potential for for money to be made or anything else is you know, we’re all solving problems whether it’s food whether it’s lawyers whether it’s you know housing as a

an entrepreneur or real estate investor, you know, and the more difficult the problem, whether it’s, you know, construction or, you know, buying a house with a bad roof for a bad foundation, you know, there’s more potential for money to be made or anything if you’re willing to solve those problems that nobody else really wants to take on or do. But the problems are just opportunities waiting. You just got to have to roll up your sleeves a little bit to dig them out.

Dylan Silver (17:55.822)
100 % I completely agree with you. Pivoting a bit here, Rolland, going from what you were doing before, attorney, prosecutor, now we’re talking grocery store, restaurant, right? So huge change, huge change. But you knew about the grocery because of course this is your family business, right? So you’d seen this for a while. There’s some overlap between produce, right, grocery, and then also owning a restaurant.

But your brother is, you know, the professional chef. So what’s your day to day like today and how much of your time is spent between grocery being the running the restaurant and then also looking at real estate deals?

Rolland Wimberley (18:41.737)
so I, I take care of a bit of everything, but, really, I mean, you kind of alluded to it a little bit. I mean, I grew up in a family business and the rest are in the, you know, grocery store industry, grocery store, hardware store. so in shipping things up to Alaska, dealing with all that. but my biggest thing is, you know, I have no problem.

not being the smartest person in the room. In fact, I don’t need to be. I don’t want to be. You know, yeah, I didn’t know how to exactly run a restaurant. I mean, I’ve done some of the back end stuff, the accounting, the books, you know, some of that, you you’re working on profits and loss, just like you are analyzing a deal for real estate. So I’m good at the math side of that and analyzing.

but on the running the day-to-day stuff. mean, we do have a manager at the grocery store that has 20, 30 years of experience in grocery store management. I’ve got my brother who at least has worked in the restaurant industry for almost 15 years now. And then with my team in Missouri and property managers and everything, I

I may not be the best person capable of doing all these little jobs, I, just like when you get yourself a lawyer, you are hiring them for their expertise. I got my brother of his expertise, I’ve got managers because of their expertise, I’ve got property managers because of their expertise. As far as my day-to-day stuff, I’m typically at the grocery store during the day, because we live on an island up here, so we get

one barge line a week. So we have to look out two weeks in advance, know what we’re gonna be shipping up from the Pacific Northwest. And if we get our freight on Monday, if we run out of eggs or milk on Friday, then you just have to wait till Monday. There’s no eggs or milk through the weekend. So we have to really…

Dylan Silver (20:59.896)
Yeah.

Rolland Wimberley (21:01.125)
be combating that, and the same goes for fresh produce or anything else. So we’re really looking into our crystal ball and trying to do that. Same thing with ordering stuff for the bar, for the restaurant, everything. You’re in a real balancing act of how much to have without being too bloated, because you can’t just call the bread truck and have it arrive in two days and drop more stuff off. So it’s tricky there.

But I think growing up with that mentality and that kind of looking ahead, planning ahead and, you know, really busting out the crystal ball that nobody has, but you can do your best case guesses based on experience has really helped in the real estate aspect as well. You know, we’re going through interesting times right now and nobody’s got a crystal ball to see what’s going to happen in the next six weeks, six months or anything else. But.

Dylan Silver (21:41.827)
Yeah.

Rolland Wimberley (22:00.006)
You we’re plugging along and nobody is just pulling their money out and sitting on the sidelines and waiting for it all to happen. I mean, you could, but that’s not… You always could. There’s always that, you know, aspect of you don’t have to play the game. You don’t have to get involved, but nothing is going to happen if you just sit…

Dylan Silver (22:13.678)
Good.

Dylan Silver (22:24.014)
I don’t know. It’s a disaster.

Rolland Wimberley (22:29.179)
court-side and don’t get involved.

Dylan Silver (22:34.094)
pivoting a bit here Rolland, I imagine as a prosecutor you were in court all the time, So going from that to this lifestyle, different lifestyle, know, I’m assuming not having to wear a suit all day, right, not sitting in front of judges. So I’ve spoken with a couple attorneys who were like, yeah, these are on the podcast, yeah, we are rarely in court, if ever, and most attorneys are not in court.

Rolland Wimberley (22:41.595)
yeah. yeah.

Dylan Silver (23:02.446)
And it takes a very specific skill set to be in court. It’s very stressful. And you have to be suited to that. And on top of that, it’s not like you just leave law school and are ready to be in front of a courtroom all day. And there was a gentleman who said, know, frankly, I think that if I was to go in a courtroom right now, I would be at a loss in a sense, because I have been so many years since I’ve been in a courtroom. So I’m curious. Now that you’re in a new lifestyle.

Do you miss being in the courtroom? Is it thrill of game day? You kind of feel like, well, I got to get back in there. Or are you like, you know what? I don’t miss it at all.

Rolland Wimberley (23:37.618)
I definitely do miss, it’s with everything, there are pros and cons, I definitely do miss aspects of it. I tell people, mean running businesses, being an entrepreneur, especially customer service and stuff like that, it’s a little bit performative. So the skill set kind of sets me the same. Guam was great for that because as a…

As a prosecutor working with that in a smaller attorney general’s office, you really got trial by fire and thrown in rather quickly. So I mean, I was in court at least three days a week. And that’s not to say like trials or anything, but just courtroom appearances, being in front of a judge. mean, all of being a lawyer, you

is research and paperwork and a lot of other things, but we were a lot more hands-on, involved, know, trying cases and because it’s a small office, I got thrown in a lot more, which, you know, works for my personality. I relish being a trial attorney and maybe I will get back to that someday. Just…

I’ve set roots down in Alaska, especially with my parents and my family and everything. So I’m kind of doing that for now. But I would like to get back into it. I mean, I don’t know if that option will be always available. Because there’s, yeah, they really want you on site and a full time.

Dylan Silver (25:30.326)
Yeah, it’s a full gig there. Yeah, it’s hard to run a restaurant and be a trial attorney. I don’t know if you know this name. There was a ASAP Rocky, which is famous. This case happened right now. And it was all over the internet. I think the guy’s name was Joe. I’m probably butchering the last name, but it was Joe T. I’ll call him Joe T, the attorney. Talking about how being in court…

Rolland Wimberley (25:33.401)
a full time job.

And that’s the thing. There’s not too many.

Dylan Silver (25:58.274)
He’s like, don’t know any other way other than to go 100%. I wouldn’t be able to sleep at night if I knew that I wasn’t defending my clients. They were my brother, my son. And I was thinking about that. And of course, I know nothing about this. When I was thinking about that, I was going, yeah, that makes sense. If you’re representing, you were on the other side. But both sides are going at it trying to win. And so I can only imagine that there’s a lot of

like game day, maybe probably less as the years go on, but still a lot of, a lot of that, that is just, you, to be something that you miss.

Rolland Wimberley (26:36.963)
Yeah, well, I mean, yeah, there’s not too many and especially for trial attorneys, you can’t, it’s hard to do any of that part time. So just the same as, mean, I used to be a wrestler in high school and college, and then I got into MMA doing the cage fighting. And I had to really cut back on that because going into law school and training and everything, I was like,

It’s really almost impossible to do that part time when, especially when the person on the other, the other side of the courtroom, on the other side of the cage from you, that’s their life. They’re doing it 100 % all the time and you can’t really just be like, oh, this is a side gig for me. Like this is my part time thing while I figure out other things in my life. So I think if I was to certainly get back into it, it would be once.

Dylan Silver (27:07.992)
Yeah.

Dylan Silver (27:30.126)
Yeah.

Rolland Wimberley (27:34.703)
the businesses and everything settle down and are managed and you know I would really have to you know have everything covered for me to go back and pick back up the suit and get back in the courtroom doing it full time.

Dylan Silver (27:50.168)
That’s right. That’s right. Get back in the go from Clark Kent to Superman, right? It’s a different way. But we’ll have to have another, we’ll have to have you back on the show to talk about mixed martial arts. I was a Jiu Jitsu guy and boy, boy do I love mixed martial arts. And I think as far as like health wise, people will say this is crazy. I’ve never been healthier and happier than when I was getting, you know, mauled daily. Like that was my favorite, you know,

participating in controlled combat sports was the happiest that I’ve ever been. But I always say this to people, when you’re growing a brand in a business or when you’re studying in law school, it’s kind of hard to be waking up at 5.30 in the morning and getting kicked in the head. And then it’s a little bit incompatible. But God bless, there’s certainly people who are able to do both. But we are coming up on time here.

Rolland, can folks go to get a hold of you?

Rolland Wimberley (28:52.081)
So pretty much my my biggest way for people to reach out to me is either on on Facebook or Instagram My Instagram is REI underscore whimper So WIMBER and then just on Facebook if you’re reaching out under my name Rolland Wimberley So I I you know, I’m currently

Doing my own thing, I don’t have a company or anything. I’ve done some private lending and some other stuff that I’ve kind of dipped my toe in the water, but haven’t really gone out to, I guess, deal search or do some of the other stuff that people are. But I welcome anybody who has any questions, whether it be about Alaska, about real estate, about kind of the journey and different adventures and different stuff.

So, absolutely.

Dylan Silver (29:49.71)
What’s the name of the restaurant in Alaska?

Rolland Wimberley (29:52.145)
So we are a bar Pizzeria It’s called the Hungry Beaver Hungry Beaver pizza and the Marine bar

Dylan Silver (30:03.256)
Hungry Beaver Pizza and Marine Bar. you’re in Alaska, go check it out. Rolland, thank you so much for coming on the show.

Rolland Wimberley (30:06.673)
Thank

Rolland Wimberley (30:10.693)
Hey, thank you for having me Dylan.