Master Off-Market Property Deals: 7 Secrets to Boost Your Income
Show summary
In this conversation, John Harcar interviews Ben Bolingbroke about his journey in real estate, focusing on off-market acquisitions and the skills necessary for success in the industry. Ben shares his unique path from aspiring doctor to real estate investor, detailing his experiences with door-to-door sales, his first property purchase, and the lessons learned along the way. He discusses his current business structure, strategies for acquiring off-market properties, and the importance of consistency and relationship-building in real estate. The conversation concludes with Ben’s future plans in land development and advice for aspiring investors.
Key takeaways
- Ben bought his first property, a duplex near the University of Utah, in January 2020 with only 5% down; by house-hacking it with roommates he went from paying $600/month rent to earning $400/month while living for free.
- He now owns 12 rental units (duplexes, a triplex, a fourplex, single families) across Utah, Idaho (Pocatello), and Florida.
- His off-market acquisition process for land: pull lists from PropStream or directly from county records, run the list through texting software (Launch Control), cold call non-responders, then mail whoever is left — hitting the same list from three different angles.
- Marketing response varies by age: older landowners respond better to direct mail letters, younger owners respond better to texting and calls.
- He pivoted from wholesaling houses to land because land sellers typically have no loan and no emotional attachment (no house on it), making deals more numbers-driven and easier to negotiate at volume.
- His land sourcing model is to find builders and developers first, learn what they want, then run marketing campaigns to find that specific land for them — effectively acting as an outsourced acquisitions team for builders.
- The biggest mistake new investors make is inconsistency — trying a strategy (cold calling, mailing, door knocking) for only a month before switching; deals often close 6-12 months after first contact, so continuous follow-up (including remembering personal details about sellers) is essential.
- His early tenant mistake: renting the basement unit of his first duplex to a tenant without running a background or credit check — the tenant turned out to be a felon who trashed the unit and never paid rent.
In this episode
- 00:01Intro: Off-Market Acquisitions with Ben Bolingbroke
- 01:00From Pre-Med to Door-to-Door Sales
- 03:03Alarm Systems and Solar Sales: Skills That Transferred
- 05:22First Deal: House-Hacking a Duplex Near University of Utah
- 06:27First Landlord Lessons: The Felon Tenant Mistake
- 07:45Current Portfolio: 12 Rentals Across Utah, Idaho, Florida
- 09:31Pivoting from Wholesaling Houses to Land Deals
- 11:43Off-Market Land Acquisition Process: Lists, Texting, Calling, Mailing
- 14:06Finding Builders and Developers as Land Buyers
- 16:03Keys to Success: Relationships and Consistent Follow-Up
- 18:14Future: Land Development and Subdivision Deals in Pensacola
About the guest
Ben Bolingbroke started college intending to become a doctor but instead spent years doing door-to-door sales (alarm systems for three years, then solar for two to three years) while buying his first rental properties during college. He now owns 12 rental units across Utah, Idaho, and Florida, has done wholesaling, and has transitioned his business primarily to off-market land acquisition, working with builders and developers and pursuing land development/subdivision deals out of Pensacola. His company is Elevate Equity Group.
Listen to the audio
“You never lose a deal because you followed up too much. It's always good to follow up.”
Ben Bolingbroke
“People will do business with people who they like and trust. So if you can get people to like and trust you, they're more likely to sell to you, even if you're not the highest offer.”
Ben Bolingbroke
“When you surround yourself with people that are doing cool things, you'll eventually do cool things.”
Ben Bolingbroke
Questions answered in this episode
How do you find off-market land deals?
Ben pulls lists from PropStream or directly from county records (county lists tend to be more up to date since PropStream sources from them). He and his VA then attack the list from multiple angles: first texting through software like Launch Control, then cold calling anyone who doesn't respond, and finally mailing the remaining non-responders.
What's the difference between how older and younger landowners respond to marketing?
Ben found that older demographics respond better to direct mail letters, while younger demographics respond better to texting and cold calling.
Why focus on land instead of houses?
Ben says land is easier to get people to sell because owners usually don't live there and don't have a loan on it, so there's less emotional attachment. It's also more numbers-driven since there's no house to negotiate over, which lets him make a high volume of offers.
How do you find buyers for land deals?
Ben identifies builders and developers first, finds out what they're looking for, and then runs marketing campaigns to source that specific land for them. He describes his business as essentially an extension of a building company's acquisition arm, using tools like PropStream or Google to find builders and developers to call.
What's the biggest mistake people make when starting in wholesaling or land investing?
Lack of consistency. Ben says people will cold call for a month, stop, try mailing for a month, stop, try door knocking for a month, stop. All the strategies work, but only if you stick with them long enough and in volume.
How long does it take to close an off-market land deal after first contact?
Ben says deals often come six months to a year after initial contact, which is why consistent monthly follow-up (calls, texts, remembering personal details about the seller) is critical to eventually winning the deal.
Resources and links
Full transcript
John Harcar (00:01.558)
All right, hey guys, welcome back to our show. I’m your host, John Harcar, and I’m here today with Ben Bolingbroke. And what we’re gonna talk about, besides his journey in real estate and business, we’re gonna talk about off-market acquisitions, finding them and maybe tools and tricks to find the better deals. Guys, remember here at Investor Fuel, we help real estate investors, service providers, really all real estate entrepreneurs, two to five X their business.
by providing tools and resources to grow that business they want to grow, which in turn helps them live the life they’ve dreamed of. Ben, man, welcome to our show.
Ben Bolingbroke (00:38.117)
Yeah, thanks for having me. It’s exciting to be on here.
John Harcar (00:41.506)
Yeah, I look forward to talking about how you’re doing your off-market acquisitions. I do off-market stuff, so I’m definitely eager to find out what you’re doing. But before we get into all that kind of stuff, why don’t you tell our audience a little bit more about you, kind of your background in business and in real estate, and what got you to today?
Ben Bolingbroke (01:00.707)
Yeah, so I kind of have an interesting story. I definitely didn’t take a traditional path into real estate. I started college wanting to be a doctor. And obviously that didn’t work out. I got good grades and everything,
During my time at college, started doing door-to-door sales and that gave me some good money to then start investing in real estate. know, and I got around a few people that I worked with that were buying properties. So I bought a few rentals during college and I just, you know, kind of fell in love with real estate. I…
I started wholesaling and trying to look for other ways to make money within real estate and go into different meetups. I eventually did graduate. I graduated with a degree in biomedical engineering, but I don’t really use that degree. I just chose to kind of go full on into real estate since graduating.
John Harcar (01:50.126)
Okay.
John Harcar (01:58.67)
That’s awesome. If you watch any of my podcasts, I like to talk about the journey and how it all started because there’s a lot of a lot of knowledge and good information that was there anybody in the in your past? Anybody that was maybe a real estate agent, a landlord, some type of influence in your life in the real estate space?
Ben Bolingbroke (02:19.033)
Yeah, I’d say mainly it was those door-to-door guys that I worked with, you know, like before doing door-to-door, I had never even thought that it was like possible to buy a property at 22 years old, you know, it just something that hadn’t crossed my mind. I thought it was something you do like in your thirties. And I had got around other young guys that were buying real estate and had rentals and creating cashflow. And it really just opened my mind up into the world of business and real estate.
And I think it does teach a good lesson that when you surround yourself with people that are doing cool things, you’ll eventually do cool things.
John Harcar (03:01.134)
May you want to do those cool things. What were you selling door to door?
Ben Bolingbroke (03:03.343)
Yeah, yeah. So I sold alarm systems for three years and then I sold solar for another two to three years after that.
John Harcar (03:17.346)
What do you think are the main traits, skills, things you picked up from the door-to-door sales that helped you in your real estate journey?
Ben Bolingbroke (03:28.271)
Yeah, think probably one of the biggest things is just the ability to handle rejection. mean, doing door-to-door sales is like, you get 50 no’s in one day, but if you get one yes, that’s a super successful day. So just the ability to kind of turn through all the no’s and not take it personally. And, you know, also the sales skills that came with doing door-to-door is super valuable in real estate.
John Harcar (03:56.504)
What do you think are some of the most important skills that you learned?
Ben Bolingbroke (04:01.563)
Yeah, I I definitely learned how to talk to people and how to negotiate and how to listen to people. And that’s been invaluable in real estate. But yeah, that’s definitely the biggest thing.
John Harcar (04:17.73)
Okay, so you saw some of these other door-to-door guys and they did they have they already bought rentals were they in the process of buying them where you did they just talking about it like how did this all start to where you made that first purchase?
Ben Bolingbroke (04:30.115)
No, yeah, a lot of them had already bought rentals and they were my age, maybe a few years older than me. And like I said, before that point in my life, I don’t think I’d ever met 20 something year old kids that had rental properties. It just kind of blew my mind that you could be that young and buy rental properties. And yeah, I was really blessed to be around.
young dudes who are making good money and then also smart with their money and investing it into properties. Because there are a lot of door to door guys that make good money but aren’t smart with their money, as you can imagine.
John Harcar (05:09.742)
They’re driving that nice car and they’re dumping all their money into toys and all.
Ben Bolingbroke (05:14.627)
Yeah, super nice shoes, stuff like that.
John Harcar (05:17.236)
Yeah, got it. Okay. So what was your first purchase?
Ben Bolingbroke (05:22.479)
Yeah, my first purchase was a duplex right by the University of Utah. And I actually bought it in January of 2020. So there couldn’t have been a better time to buy a duplex because I think over the next year, year and half, it actually doubled in value just because of COVID and everything like that. So.
I was, I remember, you know, I going to school, obviously, I was looking to rent a place for like $600 a month. Instead, I bought a duplex. I only put 5 % down and I rented rooms to all my buddies and I went from, you know, spending $600 a month to now making $400 a month and living for free. And that also just kind of blew my mind that I could even do that.
John Harcar (06:03.64)
There, yeah, house hack.
Ben Bolingbroke (06:08.763)
So yeah, was a really good experience for me and that also just kind of got me the real estate bug.
John Harcar (06:15.874)
What were the struggles? You know, your first landlord, right? Pretty much, right? What were the struggles that you were dealing with when that was having you luckily had friends, but you know, what were some of the things you came up
Ben Bolingbroke (06:27.92)
Yeah.
Yeah, no, I-
I nothing about how to do repairs on a house. I knew nothing about how a house works. I also didn’t know anything about how to find tenants. So it was a duplex. So I lived in the top part with my buddies, but the bottom part was like a separate mother-in-law basement. And the very first guy that I rented to, I didn’t do a background check or credit check or anything. I just was like, yeah, sure. If you want the place, you can have it. But he was actually a felon and he told he trashed the place. He never paid
John Harcar (06:48.501)
Okay.
John Harcar (07:00.878)
Mmm.
Ben Bolingbroke (07:01.731)
rent. If I would have Google searched his name I could have found that out that he was a felon but I just didn’t even do that. So yeah I learned some of those lessons the hard way about how to find good tenants unfortunately.
John Harcar (07:13.26)
Yeah. OK. And then how did you find this duplex? Was it listed or was it an off-market deal?
Ben Bolingbroke (07:27.111)
No, that one was on market. I think right before the pandemic, things were kind of slow and it was just a great deal. It was sitting on the market. We got super lucky. I got super lucky.
John Harcar (07:39.886)
Okay. Awesome. So how many properties have you bought since?
Ben Bolingbroke (07:45.179)
So right now I have 12 rentals and that’s spread across duplexes, triplex, have a fourplex, some single families. I have Utah, Idaho, and Florida right now. So three different states.
John Harcar (08:01.208)
Nice. Okay. What does your business look like? Is it just yourself? Do you have a team?
Ben Bolingbroke (08:06.895)
very small team so i have a b a and i have someone that helps with property management so two different property managers and then you know in the acquisition side i have a partner that i work really closely with and and that’s about it that’s some you know maybe four people total
John Harcar (08:32.184)
Okay. Okay. Where are you guys mainly doing? said you’re in Utah, Florida and where else?
Ben Bolingbroke (08:38.179)
and Idaho. So the properties that I own, most of the rentals that I own are in Utah and then I have three in Idaho and then I live and do a lot of business in Florida.
John Harcar (08:41.269)
Idaho.
John Harcar (08:53.772)
Where here? I’m in Boise. So where in Idaho? Here in Boise?
Ben Bolingbroke (08:57.805)
No, it’s actually in Pocatello. Yeah, I think Pocatello’s a great market. I love Pocatello. It’s kind of hidden.
John Harcar (09:00.686)
Pocatello, nice. Yeah. It is. It is definitely very cool. Well, it is. And I think that that’s growing too. I mean, just kind of like how Boise is growing. I think that’s growing almost as much, maybe not as huge, but it’s it’s growing from the numbers I’ve been looking at. So where is your focus? And in a minute, we’ll start talking about the off market stuff. But where is the focus in your business? Like if I talk to you 12 months from now, where do you want to be?
Ben Bolingbroke (09:19.685)
Yeah.
Ben Bolingbroke (09:31.257)
Yeah, you know, kind of tell my story a little bit more. I started wholesaling houses. I liked that. Eventually I kind of accidentally did a land deal and it was like, it was a good deal, you know, on accident. So after I did that first land deal, I started looking into doing more land deals and just saw a good opportunity in land. I like it a little bit more because
A lot of people who own land don’t have plans for it, they just obviously they don’t live there, they don’t have a loan on it. it’s just a little bit easier in my mind to get people to sell their land because there’s not a house on it. And so I like that aspect of it. I also like that
It’s a lot more based off the numbers. You know, there’s not a, there’s really not a lot to negotiate about because there’s no property on it. So you can really talk to a lot of people and make a lot of offers and it works out. So that’s kind of what I’ve transitioned to over the last year is just doing completely land and not houses. And I’ve been working with a lot of builders and developers to find them land to build on and
I really, really like the…
the land development plays. So you go in, buy a piece of land, you know, maybe put in a road or subdivide it and sell all the different different plots. I haven’t done any of those projects yet, but I’ve sold land to people that, you know, do do those projects. And so it’s been cool to hear about the things that they’re doing. So to answer your question in a year, two years, that’s what I would like to be doing is kind of the smaller land development plays, you know, developing lots for builders and
John Harcar (11:12.782)
Mm-hmm.
Ben Bolingbroke (11:27.355)
doing subdivisions and things like that.
John Harcar (11:31.864)
Very cool. All right, awesome. So let’s talk about off-market acquisitions. Kind of what’s your process, tell me why it’s important, tell me kind of what you look for in properties, et cetera.
Ben Bolingbroke (11:43.897)
Yeah, me and my VA, basically we’ll get a list from either PropStream or the counties that we work in. The county lists are usually a little bit more up to date, more accurate, because that’s what PropStream does, is they get their list from the county.
So we’ll get a list and then we try to attack these lists from a bunch of different angles. So we’ll run one list through a texting software. We use launch control that’ll text them. And then if we don’t hear back, we’ll cold call them. So we cold call a list, you know, and then we’d mark off all the people that we’ve contacted on that list. And then our final strategy is just to mail those people. So it’s kind of funny because
different people will respond in different ways. We’ll get someone that will receive a letter and they’ll call us and we’ll do a deal with them. But we look back to our records and we have called them and we’ve texted them a few times but there’s no response. So it’s kind of interesting to reach out at different angles and to see what…
John Harcar (12:49.954)
Mm-hmm.
Ben Bolingbroke (12:57.423)
how people respond. know, and obviously I’ve kind of found out that the older demographic responds better to letters, whereas a younger demographic responds better to texting and calling. Yeah.
John Harcar (13:07.864)
Yeah.
Ben Bolingbroke (13:12.303)
Which would make sense,
John Harcar (13:12.686)
100 % right and it’s really yeah everybody everybody responds at different medians and that’s that’s really the main thing so is there a specific land that you’re looking so you pull these lists I mean you find an area is there specific you know proximity in a county like is it close to big city far from big city is it you know certain acreage things like that
Ben Bolingbroke (13:22.203)
Is there a specific land?
Ben Bolingbroke (13:38.821)
Yeah, mainly it’s we find the builders and the developers first, and then they tell us what they want, and then we go do their marketing for them, essentially. So that’s just kind of how I see myself and my business is. It’s like an extension of a building company. And we’re kind of just plugging in our marketing services to a bunch of builders and developers. So like, for example, there’s a-
John Harcar (14:03.02)
You just get a list of developers in the area.
Ben Bolingbroke (14:06.265)
Yeah, yeah, you can use PropStream to do that, or you can just Google different builders and developers, and you just call them and try to form a relationship and see what they’re looking for.
John Harcar (14:18.446)
What do you find as like some mistakes people are made when they’re trying to get into maybe the land business or the whole sale or just real estate as a whole?
Ben Bolingbroke (14:29.667)
Yeah, I mean, I feel like probably the biggest mistake is consistency. And I’ve even seen that in myself and my business is that…
people will like cold call for a month and then they won’t do anything and then maybe they’ll try to mail for another month and then they won’t do anything or maybe they’ll try to know door knock for a month and then they won’t do anything. I mean all the all the strategies to get deals are good you just have to like stick with it and do it a lot and that’s eventually how it works. You know you’ll get deals cold calling but if you only cold call for a day you won’t obviously you probably won’t get any deals.
So I’d say that’s probably the number one thing is just choosing them, choosing a marketing strategy and sticking with it. I actually, I know a kid here in Pensacola that all he does is he just puts sticky notes on people’s houses saying, call me, you know, number. And he does a few deals a month, just putting sticky notes on people’s houses. Yeah.
John Harcar (15:34.254)
It’s gotta be proactive, man. You gotta take, be consistent. I love that she used launch control. I I knew the owner of launch control, Aaron, when it came out, he was part of our mastermind. And I ran my business on that thing for three years, doing 30 something deals a year. It’s a great process. But yeah, like you said, you really gotta hit all different angles. What do you figure as kinda your keys to success and as you’ve been growing and building your business?
Ben Bolingbroke (16:03.193)
Yeah, one thing has definitely been just the sales aspect of it. Trying to connect with people on things more than real estate. Because people will do business with people who they like and trust. So if you can get people to like and trust you, they’re more likely to sell to you, even if you’re not the highest offer. So that’s definitely been one important thing. I think another important thing would be
just the way in which we follow up with people. So, you know, cause we’ll get deals like a year to six months after initial contact. And we just keep following up with people month after month after month after month. And you know, I’ve, I heard this saying, but it’s like,
you never lose a deal because you like followed up too much. It’s always good to follow up.
John Harcar (17:00.972)
No, never. Yeah, mean, I, yeah. Do you have an automation? Do you have, are you doing it through the text or you have like automation in your CRM?
Ben Bolingbroke (17:12.025)
Yeah, both. So texting, follow-ups, and then we’ll just schedule calls. So I’ll call people personally and follow up. And people like it when you remember something about them. So like, hey, how’s your son doing? Who was in the hospital or whatever. People really connect that way.
John Harcar (17:31.586)
The human touch, People want to be felt and heard, and if you remember those specific things. What advice would you give to someone looking to get into the game?
Ben Bolingbroke (17:32.943)
Yeah.
Ben Bolingbroke (17:42.895)
Yeah, I would say to just keep it simple. Choose one thing, one marketing strategy and try to go deep into one marketing strategy and just make it your own. You know, whether that’s calling, texting, mailing, reaching out to on market properties, MLS listings, stuff like that. And just, yeah, choose one thing, go really deep into it and surround yourself with people that are doing that thing and you’ll have success for sure.
John Harcar (18:11.116)
Nice. Anything big on the horizon for you? Any big deals you’re working on? Any coaching programs that you’re building or anything like that?
Ben Bolingbroke (18:14.267)
I need big deals.
Ben Bolingbroke (18:20.409)
Yeah, there’s a few big land development deals we’re working on right now. I’m definitely not the expert when it comes to subdividing and doing all the wetlands mitigation and stuff like that, but I do know people who are good at that stuff, so I’m working to partner with people that are good at that stuff. yeah, I really like Pensacola where I live because
You kind of get all ranges of the market. Like if you go north, there’s really cheap land and you can buy and sell cheap land. But as you go closer to the coast, land gets really expensive and you can do really big deals. So, yeah, there was a deal that we were working on selling to DR Horton. I’m not 100 % sure if it will go through or not, but it’s been a fun experience to find the land and get the plat map drawn and get the wetland studies all done and the perk test.
John Harcar (19:00.12)
Yeah.
Ben Bolingbroke (19:16.713)
done and you know get it ready for a builder to buy and that value add process that we do has obviously taught me a lot but it’s been really fun and yeah a bad deal and a few other really big acreage deals are fun to work on.
John Harcar (19:37.326)
If there’s folks on here that are listening that may want to talk to you about, know, your journey, talk to you, maybe want to invest with you in some of these land deals or whatnot, how do they get in touch with you? What’s the best way for them to reach out?
Ben Bolingbroke (19:39.065)
So I’m here that I was.
Maybe you want to invest with you and…
Ben Bolingbroke (19:49.273)
Yeah, I’m on LinkedIn, Ben Bowenbrook, you can look me up. Our company is Elevate Equity Group, and if you go to elevatequitygroup.com, you can submit your info, and that’s an easy way to get in touch. I’m also on Instagram and Facebook, just at Ben Bowenbrook, very simple.
John Harcar (20:11.95)
Cool. Well, Ben, man, I appreciate you coming on here and sharing all that. You know, guys that are out there listening, I hope you got some value. If you have any interest, please reach out to Ben. Thank you again, Ben. And guys, we’ll see you on the next one. Cheers.
Ben Bolingbroke (20:24.281)
Yeah, thank you.
