Financing, Marketing, and Growth: Insights from Mortgage Expert Jeff Chisum

Summary and Highlights

1. Financing Your Short-Term Rental Property

Understanding Financing Options
A big misconception in the STR world is that you need to put 20% down when buying a vacation home or rental property. Jeff explains that’s not always true, especially if you’re buying a second home or investment property. There are special financing options that can help you buy with as little as 10% down.

Tip for New Hosts:
Before buying your property, talk to a mortgage expert who understands STR-specific loans. This can help you find better financing options and save money.

2. Mindset Matters: Overcoming Challenges

Facing Challenges with a Positive Mindset
One of the most important things Jeff emphasizes is having the right mindset. In the STR business, you’ll face obstacles—whether it’s managing your property, dealing with guest issues, or handling market changes. Jeff believes these challenges should be seen as opportunities to grow, not as roadblocks.

Tip for Hosts:
When you hit a bump in the road, instead of getting discouraged, think about how you can solve the problem. This mindset will help you move forward and get stronger as a host.

3. Building Relationships with Guests

Keep Guests Coming Back
Jeff shared how important it is to build strong relationships with your guests. When he bought a golf course cabin, the previous owners had loyal guests who returned year after year. By honoring these relationships, Jeff kept those guests coming back.

Tip for Hosts:
Even if you’re new, you can start by getting to know your guests. Small gestures, like remembering their preferences or offering special deals for repeat visits, can build loyalty and keep people coming back.

4. Using Social Media to Get More Guests

Targeted Marketing on Social Media
Jeff talks about how he uses Facebook and Instagram ads to target the right guests for his properties. Social media allows you to reach specific audiences—whether it’s golfers, families, or pet owners. By running targeted ads, you can attract guests who are most likely to book your property.

Tip for Hosts:
Start experimenting with social media ads to attract guests. You can run small, targeted ads without spending a lot of money. It’s all about reaching the right people with the right message.

5. Building an Email List for Direct Bookings

The Power of Email Marketing
One of Jeff’s top tips is to collect guest emails and build a database. This gives you a way to connect with past guestsand encourage repeat bookings. Jeff also recommends creating lookalike audiences in Facebook ads, which helps you find new guests who are similar to your best customers.

Tip for Hosts:
Start building your email list from day one. Use it to send booking reminders, special offers, and updates about your property. And don’t forget to upload those emails to Facebook to target similar guests.

6. Consistency is Key to Success

Stay Consistent in Your Efforts
One thing Jeff learned from his own experience is that consistency is crucial. Whether you’re marketing, responding to guest inquiries, or keeping your property in great shape, consistency leads to steady growth. It’s not about doing everything perfectly, but about doing the right things regularly.

Tip for Hosts:
Pick a few important tasks (like marketing or guest communication) and do them consistently. Even small, regular actions add up over time and help you grow your business.

7. Podcasting as a Tool for Networking and Learning

Sharing Knowledge Through Podcasting
While Jeff is primarily a mortgage expert and STR host, he also runs a podcast. He shares that podcasting or guesting in podcasts is a great way to learn from others and connect with experts in the industry. Plus, it helps you build a personal brand and stay visible to potential guests or collaborators.

Tip for Hosts:
If you enjoy sharing your experiences, consider appearing in podcast. It can help you build relationships, share useful tips, and even attract new guests.

---

Key Takeaways for Hosts:

• Don’t be afraid of challenges—use them as learning opportunities.
• Consistency is the key to long-term success in STR.
• Build and maintain your email list to encourage repeat guests and stay in touch with them.
• Use social media ads and online communities to target the right guests and grow your audience.
• Stay focused on the tasks that move your business forward, like marketing and guest communication.

By applying these key takeaways , you can set yourself up for long-term success in the STR industry. Whether you’re just starting or you’re already managing multiple properties, Jeff’s advice will help you stay on the path to growth.

Transcription

Jeff: And then there was the other issue of we really felt like Airbnb, Vrbo, the OTAs were killing the industry to an extent because of the fees and their rules and their regulations and the way they treated hosts, the way they treated guests, and we really wanted to take control and take some power back from the OTAs and The way to do that was direct bookings to help people save money to increase our profitability.

Also go out and market those sites to those people that were interested in those activities. And then the golf course cabin had a 10 year history as a Airbnb. And that’s really the main reason why we bought that. So we bought that property after the lake house about. Six or seven months after we closed on the lake house.

And that was the big attraction is it had that 10 year history. So when we purchased the property, we got a check written to us for those bookings, those bookings transferred, the database transferred. We had all the emails. And so we really started pushing those people to our direct booking site.

Gil: Hey folks, welcome back to direct booking simplified. We break down the strategies and tactics to win in direct bookings. And on today’s show, I have Jeff. Jeff, welcome to the show.

Jeff: Hey, thanks for having me Gil.

Gil: Yeah, you, uh, you’re familiar with the podcast game. You have a podcast yourself. Um, maybe it’s kind of kick things off. Uh, do you mind giving an introduction on who you are?

Jeff: Yeah. So, um, by vocation, I’m a lender have been since 2008. So about 16 years, uh, been a top 1 percent loan originator in the United States since 2018. Um, so, Don’t say that to brag, just that, you know, we operate at a level where, you know, we highly value the client experience, you know, what we bring to the game, but really since 2020, we’ve pivoted to where a hundred percent of our business is, uh, STR financing.

So, uh, yeah, we’ve, we’ve found a huge opportunity to educate people. Uh, about the financing options. And, uh, that’s been through, you know, Facebook groups, um, with the podcast. So we’ve been doing that for about a year and a half now, 50 something episodes, but they’re micro podcast, all designed to give people bite sized information and, you know, move on to the next subject.

But yeah, I found a, a really big opportunity to educate people on the 10 percent downside at home occupancy loan.

Gil: Nice. Nice. Um, and you’re also an operator yourself. Is that right?

Jeff: Yeah, you know, really before I found this niche, uh, as far as the lending goes, I was an owner first. Um, so, you know, we bought our first property and then, you know, as I got connected with different groups found, uh, the, a lot of people didn’t know about the 10 percent down financing. So, uh, yeah, own, own two.

Properties in north central Arkansas, the Ozarks, it’s about a hour north of Little Rock, Arkansas.

Gil: Nice. I’m in a very similar market. We’re also on the Ozark lakes as well, too. I’m my, my, my lodges in France. And so we’re not that far apart from each other. Yeah.

Jeff: Yeah, same type of terrain, you know, the Ozarks are beautiful, um, you know, nice change in terrain, lots of trees, wildlife, hiking, you know, just all the outdoor stuff. So, yeah, it’s a, it’s a great place to, you know, To go and visit. And, you know, a lot of people ask me, you know, what market should I invest in?

And I tell people, find a lake, you know, find a place that families like to go and, and, you know, be outside and do outdoor activities. So yeah, those areas, um, check, check a lot of boxes.

Gil: Yeah, from prior conversations that we’ve had together, it seems like there’s also a couple of niches that, uh, you’re able to spot kind of within, within your property and the folks that visited your property. Is that right?

Jeff: Yeah. You know, we’ve found, you know, since this, these areas or this area in particular, I won’t speak for your area, uh, Cause I don’t know as much about it, of course, as where we’ve invested, but, uh, it’s a lot of families that are coming together from different parts of the country. So, yeah, we’ve really found that the, the properties that we have, because they, Sleep at least 12.

We’re seeing a lot of multi generational stays.

Gil: Yeah. Yeah. And, um, you’re alongside, uh, a golf course too, right?

Jeff: Yeah. One of the properties is in between two holes on a golf course. So, uh, just to, you know, really, really beautiful golf course with, you know, of course, a lot of trees and, uh, changes in terrain, but it’s, yeah, it’s just absolutely beautiful.

Gil: Yeah. How have you seen, uh, that landscape change kind of throughout the years? Um, coming into COVID and coming out of it, you, you’re one of the hosts that were, I was considering like almost an OG where you had been investing before investing was, uh, investing in short term rentals before it was like really the hot thing right now.

Um, but what, what was it like back then when you first got into it versus what is now?

Jeff: Yeah, it’s, you know, we got in before the COVID wave. We didn’t know, you know, what, what was to come. Uh, just knew that we wanted a place where our family could go and enjoy it. And, you know, we were hoping that it would at least pay for itself. So, you know, once we got the property up and going, you know, we were really having, uh, People that, you know, kids weren’t in school and, uh, people were working remotely.

So they were looking to get out of the house and yeah, definitely took advantage of that. Um, on the other side, you know, we really didn’t see a let down too much. It, you know, uh, we, we definitely didn’t see the upward trajectory that we had seen, but we certainly didn’t see a decrease.

Gil: Yeah, that’s interesting because I, I’ve heard many markets now more recently, maybe in the last eight months or so started to see a compression and a lot of that had to do with some of these big markets really getting a lot of influx of new supply or basically new short term rentals on the market that people are competing against.

Um, that doesn’t seem like it may apply specifically in your area. Maybe are you in maybe a less saturated area than some of the other ones?

Jeff: Yeah, I would say so. And, you know, it didn’t take a lot to stand out in the crowd, but with that, you know, I, I really, uh, came across a lot of, of good, uh, instruction and coaching on how to set yourself apart, how to showcase your property. So, you know, you could stand out in the crowd. So, you know, our, our lakefront property is in the top 1 percent in that market.

And I really attribute. You know, all the things that I’ve learned along the way as far as, um, showcasing your property, making sure that you have the right amenities.

Gil: Yeah. Yeah. Yeah. And what have you seen kind of on the lending side? So I, I suspect probably in the past, like 12 months, it was a lot slower and things are starting to pick up now that the interest rates are, are dropping quite a bit. What, what, what’s, uh, what’s the magnitude of changes that you’re seeing?

Jeff: Yeah. So my, my business in 2023 was up about 30%. Um, so, you know, where everybody else was dropping 60 to 70%, uh, because, you know, typical loan officers just doing deals for people that are looking to buy primary residence. So we saw that business, um, you know, decrease quite a bit, which, uh, was, I was still.

Uh, experiencing the blessing in disguise that, you know, I transitioned to this niche, so people were still buying properties. It was still, you know, high demand this year, combination of the higher interest rates, uh, people, you know, with the uncertainty around the economy and the upcoming election, we’ve definitely seen a decrease in activity, but yeah, you know, Kind of ironic.

We’re, um, recording this today where the feds announced a rate cut for the first time since 2020, uh, mortgage rates are going to follow. So, yeah, I, I really anticipate we’re going to see, uh, a lot more activity in the market.

Gil: Yeah, yeah, yeah, yeah, it’s going to be interesting. I think a lot of folks were almost holding out for a little while to see kind of where things were, were, were landing. Um, and I think people are on the sidelines just waiting to bounce back, back into the game as. At least what we’ve seen is like the housing prices have gone down quite a bit over the last few months, actually probably even the last year or so.

And if the rent interest rates are, are, are going down, um, and the prices haven’t readjusted back then, it’s a great way to, it’s a great time to start bouncing.

Jeff: Yeah, I agree. Um, you, you don’t want to wait until everyone has jumped off the bench because they feel like rates have dropped, um, as much as they’re going to. Um, so I, I, I really think in six months or so we’ll see rates drop at least a percent. Uh, and there’ll be a lot more people that, you know, that were on the edge of the bench or now off the bench.

So, you know, really, even though you may not catch rates as low as they’re going to be, uh, you definitely don’t want to be in that market where it’s multiple offers and, you know, You know, you’re back to doing kind of some of the ridiculous stuff, in my opinion, that you have to do to get into a deal, you know, waiving inspections and option periods and offering, you know, excessive amounts over list price.

So I think today is, is, and over the next few months will be a good balance between fairly decent interest rates, but. You know, not, not a lot of, um, you know, multiple offer situations.

Gil: Yeah. Yeah. Yeah. Kind of going back to it, you were, you started off as being a lender, maybe in like the, the long term or even primary space there. What drove you to now almost pivot a hundred percent into the short term rental space? What did you see early on?

Jeff: Yeah, it really was just the opportunity. Um, it was one of those things that once I bought my property and this kind of goes back, you know, uh, five years or so before 2020, where Fannie Mae and Freddie Mac changed their policy around the second home occupancy loan that really made it more friendly towards.

People that were going to buy these properties and then rent them out on a short term basis. So I’d stuck that information in my pocket and then as we, you know, we’re deciding where we want to invest, uh, and landed on short term rentals, you know, I, I got the information back out and, uh, you know, it was just a, a great opportunity to, you know, Uh, acquire one of these properties, uh, with the 10 percent down loan.

And so, you know, that’s really where I started to get connected with different groups because I, I knew there was a lot to learn, um, about the space and the asset class. So, you know, as, as. Um, I became more and more involved with these different communities and the different conversations that were going along and, you know, uh, pivoted to, uh, working with clients that were interested in buying short term rentals.

I was getting told over and over again, and really, to this day, I’m still told. Jeff, I, I didn’t know that you only had to put down 10%. You know, I talked to my loan officer, told him I wanted to buy a investment property and they were telling me I had to put down 20%. So yeah, really it was, you know, just having that knowledge, you know, having executed on that knowledge and then just being able to share it with other people that didn’t know about it,

Gil: Yeah, that’s, that’s amazing. I wasn’t familiar with it prior to the change five years ago. What was the structure like for Fannie and Freddie back then prior to the change?

Jeff: Yeah, it was just really more restrictive, uh, when it came to, you know, not being able to rent it out on a short term basis, having to stay in at a certain amount of days, mileage requirements, um, as far as how far it had to be from your, uh, primary residence. So, you know, they knew that people were, uh, utilizing these properties as short term rentals.

So they weren’t, you know, just staying in them and then they were vacant. Um, so really it eliminated the gray area around people renting them out on a short term basis. So, you know, they didn’t feel like, you know, potentially they were committing mortgage fraud anymore. And it only makes sense that if you are going with a product where you have to fully qualify.

So you’re not going to be able to use potential income to qualify, uh, that Fannie Mae would say. Well, you know what you can qualify on your own, but if you have this ability to supplement your own ability, uh, to, to pay the mortgage on a monthly basis, why wouldn’t we make our policy that’s friendly towards that?

So that was really the big differences. People are no longer having to operate in this gray area because it wasn’t defined and how you could utilize it as a short term rental.

Gil: Got it. Some, it sounds like also some of those regulations are still in place. So like we still have. The distance from your primaries is still one of the criteria is that still exists today, right?

Jeff: It does not. No. Yeah. So there, no. Yeah. And if, if you hear that, it may be, you know, that entity or that originators overlay. Um, so they add on to the Fannie Mae policy where they put some type of mileage restriction in place. And so that could be, so there’s kind of a dis, uh, Designed, uh, policy, uh, where, you know, they can say conclusively, all right, well, it’s, you know, more than 50 miles from your primary residence, it meets our requirement.

But when it comes to Fannie and Freddie, there’s absolutely no distance requirement. It just has to make sense.

Gil: Interesting. I’ve always heard this 50 mile range. Um, pretty much with every lender that I talked to, I always thought that that was a pretty fanny, um, stipulation or, or, or rule that they, that you must kind of comply to.

Jeff: And so everything that I share, um, with people have, has all been vetted with Feeney and Freddie because initially when we got into the space and we started doing deals and we were submitting things to underwriting, we would get feedback from underwriters like that. You know, it’s, you know, well, this property is only, you know, 40 miles away or, You know, the contract says that they’re going to have bookings that are going to, uh, transfer to the, the buyer.

Um, All of that, we vetted out with Fannie Mae directly because, you know, the underwriter understood the new policy, or they only, they only understood the old policy or knew the old policy. So there was definitely a period of time where we had to educate the underwriters, uh, that the policies have changed.

Gil: Is there still a regulation on how many days within the year that you need to stay there?

Jeff: No, no. Um, kind of a summary of the policy is, is that you just can’t, you can’t You can’t lose the ability to occupy the property when you want to. So even though it says that, you know, you have to utilize it for your own enjoyment for at least half of the year. Um, if you’ve got bookings on, you know, Airbnb, the OTAs, you have your own direct bookings.

Those are not legal lease agreements, you know, they’re, they’re bookings. So you, as the owner effectively go in and cancel booking anytime you want to, if you decided to go and stay in it. Um, so that is one of the areas where underwriters would push back on us. And we would actually show the fine print from Airbnb, Verbo, where it said they’re not facilitating a legal lease agreement.

Um, so that, that’s, you know, where we’ve been able to educate. Not only underwriters, but our clients that, you know, as long as you don’t put yourself in a position where you have a legal lease agreement in place, which is typically going to be those stays that are 30 days or more, you know, definitely not, you know, a six month lease or a one year lease, that would be a huge issue.

But as long as there’s not a legal lease agreement in place, then you’re fine to have as many bookings as you want to. And really, you know, that is one of the policy changes in their verbiage. Uh, the number one piece of criteria right out on the gate for a second home occupancy loan is that your intention is that you’re going to go and stay in the property at some point during that first year.

So no longer does it say, you know, you’ve got to stay in at a minimum of two weeks. That’s the other thing that we hear is, well, I’ve got to stay in at least 14 days. That’s where the IRS lane gets kind of crossed into the mortgage lane. And people get that information confused with tax policy and, you know, the people that are wanting to take advantage of the tax benefits, that’s all in the tax code when it comes to the amount of days that you can stay on a property, but has nothing to do with the mortgage qualifying or the

Gil: Yeah, yeah, yeah. I see, I see a lot of folks when they start getting into it. They are doing a lot of. Do diligence on their side, but they’re trying to learn how to operate, how to, how to close on the loan itself. But then also on the backend side, when it comes tax season, how to navigate that and the complexities around cost segregations and such.

And I can totally see that we start to blend some of the worlds together, which is two different entities. There’s two different regulations that almost have very little crossover, uh, at all.

Jeff: Yeah, I know. And that that’s a great point. You know, you definitely want to consult with the CPA that specializes in short term rentals. Um, you know, they, they may be even well versed in long term rentals and working with investors there. But if they don’t know the specific tax code around short term rentals, you’re gonna miss the boat on the tax benefits because they’re distinctly different.

They’re significantly different. Uh, and that’s why people have been attracted to the short term rental from a tax savings perspective is it’s much easier to qualify. And take advantage of those than it is on a long term rental.

Gil: Yeah. Is it still true or is it true that you’re only able to receive a second home loan, one per market? Um, is, is that, is that, is that one a true one?

Jeff: It is not, no, um, and, and we’ve executed on our understanding of, of what that looks like as well. So I kind of, a few years ago coined this phrase, the bigger and better rule, which it’s not a stated rule. It’s just kind of this idea that, um, You know, you can own or you can use that product in the same market area, as long as it makes sense.

So an example of that would be, you know, you bought one a year ago, use the 10 percent down, second home occupancy loan. It was a three bedroom, two bath, you know, you, you and your family went and stayed there from time to time, but you just found that you weren’t being able to. You know, bring additional guests with you, or you couldn’t bring the grandparents with you just cause the house wasn’t big enough.

So a year later you come back and say, you know, love the area, but this, this property just isn’t fitting our family’s needs. We want something bigger. We want something better. So if you can, you know, Explain that. So pretty, pretty easy. You know, we have a three bedroom, two bath. Now we want a five bedroom, three bath.

Uh, and this one that we’re interested in has this amazing view. Uh, our others just kind of sits down in a valley or whatever the case may be. That’s kind of an idea of the bigger and better role. Um, I even had a case of accessibility. So I had a client that they had bought a property in the Smokies. Uh, it was one of those, um, properties where you get out and it was kind of a height to get up to the house and she, she, uh, unrelated to the property, blew out her knee, had to have surgery, and she really could no longer get up to the house.

So now she was trying to find something in that same area that was more accessible, uh, and that made sense to the underwriter why they would be using that 10 percent down second home occupancy loan to Smokies. So they found something where you get out. You can walk right in it’s easy to get into the house.

So, uh, yeah, the bigger and better rule.

Gil: Have you seen anyone, uh, downgrade to this? Their second home to the 10 percent down and get a smaller property.

Jeff: Haven’t, haven’t really seen that as much. Um, so that, that one would be a little bit harder to to an underwriter. Uh, it’s not out of the question though. You know, it could be the case where, Hey, we found that the kids, you know, now that they’ve moved out, they’re not going with this as much. We really want something that’s more in it.

You know, it was the five bedroom, three bath, you know, big cabin. Now we just want something for the two of us. So that, you know, you, you, you could pass that through. Uh, to where it, it makes sense, but you know, again, the attention has to be that during that first year, you’re going to occupy that property at some point, uh, during that first, uh, year.

And that’s the other thing after the first year, you’re, you are released from any occupancy requirements. So, you know, if you want to turn it into a long term rental or, uh, you know, a full time short term rental, uh, then, you know, you’re, you’re released from that after the first year.

Gil: have you worked with anyone that, from my understanding, with these loans, you can only do, um, under your personal name. You can’t do it under an LLC. Um, I’ve heard folks kind of transition to an LLC. What’s your, what’s your thoughts on that?

Jeff: Yeah. So we’ve, we’ve had some recent clarification around that with the 10 percent down second home occupancy loan to where you do have to close in your personal name, but you can turn around after closing, uh, right after closing and transfer that title into an LLC. As long as the borrower is, uh, equal or majority owner.

In the LLC. So our typical scenario is, you know, it’s, it’s a husband and wife, or maybe it’s two different family members and their LLC is set up 50 50. So yeah, that’s, that’s not an issue. Now the DSCR loan, the debt service coverage ratio loan, which is where you’re not using personal income to qualify at all.

It’s. The, the approval really is all based on the property, uh, showing, uh, through different means that the gross income is going to equal the principal interest taxes and insurance payment. Uh, you can do that loan in the name of the LLC. You can hold title, uh, initially right off the bat in the name of the LLC.

You are required to be a personal guarantor. Um, so, uh, there, there still is the aspect where your, your personal name is tied to the loan, but it can be done in the name of the LLC.

Gil: Yeah. Yeah. Makes sense. Uh, switching, switching, uh, topics, just, just back on a, back to your operator, uh, mindset or your, your SCR operator, um, one of the things we talked about, uh, Previously, it was kind of what you’ve done in the direct booking side of things as well, too. And that’s kind of why we got connected.

Um, can you give listeners a kind of a sense of what you, what you’re doing to help you kind of diversify your revenues away from the big LTAs?

Jeff: Yeah. So the, the lake house, um, which is, you know, lakefront property, we have two boat slips attached to it had never been a short term rental. Um, so, you know, naturally right off the gate, You know, we put the properties on Airbnb, Vrbo, uh, and, and, you know, the, uh, being on a lake, the summer was the busiest time of the year.

So that very first year, June, July, and August, we had a hundred percent occupancy. Now part of the issue, uh, or The one thing that we identified was, is we need to back off our personal use because three of those weeks were our family going and staying in it. Um, so we kind of went around, you know, that first year we’re booking slow down, October, November, December.

January and February pick back up around spring break into, you know, uh, April, May is the weather got warmer and then, you know, did the same thing the second year, but what we identified that second year is. We really needed to maximize our opportunity in those shoulder seasons. And we identified, we really needed to target people that were, um, interested in the activities that that area supported.

So, you know, we really are very close to four season area because of the activities that, uh, go on in that area. So the late. Uh, front home is in a community with two golf courses. Um, so separate from, you know, our golf course cabin, that’s in a whole kind of different, uh, on a whole different golf course in a different area, but we identified, you know, golf, you know, and then we started thinking the other things that people are doing hiking.

Uh, you can do that, you know, pretty much all year. Uh, there’s a tennis center. People are playing pickleball, uh, high off road. So there’s in this community, there’s 90 miles of off road trails. So, uh, the community that we’re in Fairfield Bay was the very first timeshare community and then. The United States back in the sixties, uh, which is crazy that it all kind of started in Arkansas.

And then people figured out, uh, we can take this concept and go to, you know, more, uh, popular areas in the United States. So when they, when they designed this community, it was a master plan community, they, they cut all the roads in. But they only paved about 25 percent of those roads. So as the years went on here within probably the past six or seven years, uh, the community found an opportunity to bring in revenue by developing these off road trails.

So now there’s 90 miles of off road trails. So, you know, your side by side, um, your four wheelers where you can go and just ride all day long. So. You know, we, um, uh, you know, it was just a matter of identifying and targeting and finding ways that we could reach people that were interested in those activities.

And then, you know, there was the other issue of, we really felt like Airbnb, Vrbo, the OTAs were, were killing the industry to an extent because of the fees and their rules and their regulations and, you know, the way they treated hosts, uh, the way they treated guests. And so. We really wanted to take control and take, you know, some power back from the OTAs.

And, you know, the way to do that was direct bookings, um, you know, to help people save money, to increase our profitability, uh, but we could go, also go out and market those sites, uh, to, to those people that were interested in those activities and then the golf course cabin had a. 10 year history as a, uh, Airbnb.

And that’s really the main reason why we bought that. So we bought that property after the lake house about six or seven months after we closed on the lake house. And that was the big attraction is it had that 10 year history. So when we purchased the property, we got a check written to us for those bookings.

Um, Those bookings transfer, the database transferred, we had all the emails. And so we really started pushing those people to our direct booking site. Um, and you know, they, they love that, you know, they were able to save those fees because historically they had been just going directly through Airbnb, you know, year over year.

And, you know, we had people that they had a 10 year history of, of coming back year, year over year to the golf course cabin.

Gil: yeah. Did you have to negotiate that as part of the purchase agreement or did they pretty much kind of give that up to you?

Jeff: Well, they’ve, they felt a responsibility to their guests, um, to, you know, make sure that that, that was a good handoff to the next owner and the owner knew why we were buying the property. So, you know, it, it, they knew that we weren’t going to go stay there. Uh, which I will say as much as I’ve said about the 10 percent down, second home occupancy and your intention to occupy the property, we use whole, whole different financing to buy the golf course cabin.

But, uh, Uh, you know, because we were buying that as a true investment property, that was definitely, you know, an attraction to buy that property is because of that short term rental history.

Gil: Got it. Got it. So, okay. So, so the owner wanted to make sure that whoever stayed there in the past had the opportunity to stay there again. Were they a kind of a solo operator just like you and myself, or were they a bigger. Okay.

Jeff: Yeah. Joe’s Joe, Joe’s golf course cabin. It was Joe and his wife. Yeah. And, and yeah, they, they finally got to a point where they were ready to move on to something else. You

Gil: folks have had folks come back year after year. Um, and kind of see that go away instantly.

That, that, that’s not a good feeling even if you’re not fiscally. Yeah.

Jeff: Yeah, they had built, you know, relationships with those people. They knew him by name, you know, it was year after year. They were booking the same, you know, week or weekend and, you know, it had become, um, you know, a part of, of their lives and, and, uh, their traditions. And, and, uh, yeah, Joe, Jeff, Joe definitely want an owner that, you know, That, uh, wanted to, you know, facilitate those, those people still being able to come back year after year.

Gil: Yeah. That’s, that’s amazing. Can you talk to me a little bit about Um, you’re now doing also additional marking above and beyond kind of the initial list that you got it in there. Um, can you kind of let us know what are some of the marketing tactics that you’re using to drive a new leads to your direct booking site?

Jeff: Yeah. So, you know, with the way that social media, uh, is, is geared or, you know, meta is interested in paid ads, you know, they can be very targeted. So, you know, back to those interests, it’s very easy to set up ads, you Based on certain interests based on certain age ranges. So, um, you know, when, when, um, we’re looking at the, our target audience, we can really pinpoint those ads to reach those people.

So, you know, we’re seeing a lot of people that are coming together from different parts of the country and they’re all meeting in this one place. So. Multigenerational stays where the 20 something couples are being invited by their parents to all go and get together. Uh, you know, we definitely can target those people.

And so, you know, the golfers, the tennis players, the pickleball players, uh, and then, you know, also just becoming a part of those different groups where, uh, people, those groups on Facebook or are. Set up to, uh, bring those different communities together and then, you know, just monitoring those posts on, uh, and finding those opportunities where we can share our properties and in turn, share our direct booking sites.

Gil: Yeah, how much energy do you put into it on like a weekly basis or maybe even a daily basis on just monitoring those feeds?

Jeff: Yeah, I mean, it’s easy because you know, one, once you kind of tap into them, then, you know, Facebook wants you to, to be a part of those. So, you know, it’s very easy, uh, and fits in with my business because, you know, I’m constantly monitoring. Activity when it comes to people asking questions about loans. So it’s hard to, you know, say how many hours a day, but I spend a lot of time just because, you know, there’s a lot of opportunities there, easy ways to connect with people.

Gil: Yeah, it sounds like you’re probably, your feed has now been, I don’t know, manipulated. It’s the right word, but it’s been, uh, put together by Facebook to, to show you the groups that you’re a part of for your lending side, but also the groups that you, um, post on for your short term rental side too. So you’re not having to go into the groups individually and find find the right pose.

You’re just naturally scrolling as you normally do. Probably.

Jeff: yeah, that’s exactly right. Yeah. They, they’re, they’re gearing my feed towards my interest and my activity. So when my interest and activities are around lending and, you know, those people that we want to target, it just, yeah, it just shows up.

Gil: Yeah. One question. I’m interested in hearing whether or not you do any lookalike audiences. Um, and if you’re not, then I would love to kind of tease you with a little bit of it too.

 Do you do any lookalike audiences within Meta or Facebook?

Jeff: Uh, no, no, I’d love to hear about it.

Gil: Yeah. So I learned this a little while ago, but if you have a large database of emails, what you can do is upload it to Facebook and create a lookalike audience. And what Facebook will do is they’ll go through match those emails back up to the profiles that they are associated with and figure out if there’s.

Any trends and locations, hobbies, interests, friends, and those sorts. And they’ll create a lookalike audience for you and you’re running ads rather than doing it off of purely location or interest groups, you can do it against the lookalike audience and you can still narrow it down by location, but it just gives you a much sharper spear to run those ads against.

Jeff: Ah, so, uh, an, an either an even deeper level of why you want to make sure that, that you have a database.

Gil: Yeah. So we do this for our Staphy emails. So we collect emails for every guest that stays with us. And, and we put that in a database and every so often we’ll go in and we’ll upload that list. And I don’t, I haven’t figured out a way to do it automatically, but almost like every quarter we’ll update the list on Facebook.

We’ll download the entire list. We’ll segmented by different properties or markets. Um, because we don’t want to blend the list that we get from, for instance, our Branson property and our Smoky’s properties. And put them in the list into the same lookalike audience because they’re different avatars. So we’ll segment the list by by folks, and then we’ll then create the lookalike audience and then run our ads against that.

And it’s much, much more effective.

Jeff: Nice. Nice. No, I, thanks for sharing that. I, uh, I will definitely do more research on how to take advantage of that for sure.

Gil: Yeah, especially since you have such a big list of folks that have already stayed with you in the past, and you’re already running ads like you’re. You’re one to really benefit from something like that.

Jeff: Yeah, absolutely.

Gil: Awesome. Jeff, any other tactics or strategies that you want to share with our listeners? It sounds like ads was a big one, having an existing list of emails that you can start to email against, um, and then really being active on some of these Facebook groups, um, that you’ve identified.

Um, was there anything else beyond those that you wanted to share with the, our listeners today?

Jeff: Well, yeah, it’s just maximizing your database. Um, you know, making sure that you’re following up with them, staying connected with them. Um, you know, if there are opportunities in slower seasons to offer discounts, to, you know, you know, Invite them back. So yeah, definitely maximizing your database, but it starts with creating one and maintaining one and adding to one, but yeah, stay fi is a really easy way to, you know, keep that going.

Gil: Absolutely. Absolutely. Absolutely. Well, Jeff, thanks for kind of walking me through many different parts of your business. Uh, both your STR side, you as an operator, how you grown, how your direct bookings grown, but also educated me on a lot of myths that I’ve now busted, uh, around the lending side and the second home, uh, loan there.

So I appreciate you sharing those with us. Um, I usually end the show with two questions. One’s a mindset question and one’s a kind of a takeaway tactical question on the mindset question. First, what’s that one piece of mindset advice that you would give to someone that’s starting something completely new?

Silence.

Jeff: in our short term rental business is, um, just having the mindset that obstacles are merely something to overcome, they, they shouldn’t be a situation where, uh, they defeat you. So just, just your overall mindset and how you.

Uh, react and respond to obstacles. Um, so yeah, understanding that they’re just opportunities to, uh, come up with solutions and sometimes on the other side, uh, you’re better off for that. Uh, sometimes it just means moving on in the same direction you were, but sometimes it means making you better than you were before.

Gil: Awesome. Awesome. That’s a good one. Uh, on the tactical side, you may have already said this just recently, but what’s that one tactical advice that you want folks to put into practice today?

Jeff: Um, I would say just consistency. So. You know, um, again with, with my own personal business, with the short term rental business, the more consistent that I can be in the activities that, uh, will grow the business, uh, will lead to, um, good results and when you’re inconsistent, it’s going to lead to kind of a roller coaster of, um, So yeah, that, that would be my tactical advice is just identify the activities that will lead to growth and be consistent in them.

Gil: I bet you, you apply that to the podcast that you run now that you’re, you’re 56 episodes in. That’s a, that’s quite a, quite a milestone that a lot of podcasters don’t get the opportunity to get to.

Jeff: Yeah, no, absolutely. And you know, it, it, uh, definitely have had to have a recommitment to consistency with coming out on a. weekly basis with a new episode, but also encouraged when I talked to someone, which was just a couple of days ago, uh, first time I had ever, ever talked to him and for them to share, they’ve been listening to the podcast since the very beginning and appreciate the information.

So, um, yeah, that’s been nice to get that kind of feedback and get it on a pretty regular basis.

Gil: Being a podcast host is definitely very, very rewarding. I bet you feel this yourself. It’s just you ever you try to every time you record, you try to find those nuggets of real valuable content and quality content that you can provide your listeners. And it’s always on the hunt to find the next guest that can help you deliver that, that value that back there to your listeners.

Jeff: Yeah, absolutely. Um, you know, it’s fairly easy formula, you know, how, how do I educate? How do I help people solve a problem? Help? How do I help people get to a place that, uh, they’ve been struggling to get to? So yeah, it’s, it’s 

pretty awesome.

Gil: Awesome. Well, Jeff, where can folks find out more about you? Where can they follow you?

Jeff: Yeah. So, uh, Instagram. Uh, Jeff Chisum mortgage pro best information around financing, uh, is on my website. So strhomefinancing. com got some good informational videos. And then of course the podcast. So Apple and Spotify STR home financing. Uh, those are three great ways to connect and everyone to get on a phone call with me.

We’ve got a scheduling link on the website.

Gil: Awesome. Jeff, it was great to have you on the show and, uh, thanks again for sharing your wealth of knowledge.

Jeff: Yeah. Thanks for having me.

Gil: Thanks. Bye.

Yeah.