The Flip Talk Podcast | Jake Henderson | Real Estate Empire


Jake Henderson, a realtor, was not happy working a dead-end job. Stuck in a rut, he craved a life of freedom and purpose. Fueled by the desire for early retirement, he discovered the power of real estate investment. In today’s episode, Jake Henderson chronicles his dream of creating a business empire that provides financial security and imparts valuable lessons of hard work and entrepreneurship to his future children. His story is an inspiration to anyone seeking a more fulfilling career path. It’s a story of hard work, smart strategies, and the power of believing in yourself. Tune in and be ignited to write your own real estate success story!

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Jake Henderson’s Journey To Financial Freedom And Entrepreneurship

Welcome to the show. Go to FlipTalk.com for everything coming up in the Flip Talk world. I am honored to have Jake Henderson from At Home Wichita Real Estate.


The Flip Talk Podcast | Jake Henderson | Real Estate Empire


Welcome, Jake.

Thanks for having me here.

I’m so happy to have you. You and I know each other. We’ve attended some events together with the Inner Circle Elite community of Don Costa’s.

They have amazing events. I always love going there.

We’ve known each other for a couple of years. I know you’re doing some big things. I interviewed Ely who is a client of yours from there in your town. Ely speaks very highly of you and what you’ve done for his business. I’m excited to get you on, especially with everything that’s going on with the changes with NAR and how the real estate agency world is changing.

With the NAR stuff, I don’t think I am personally as concerned as some other agents I’ve been talking to, but with the way I do business, I don’t think I’ll be as affected.

We’ll get more into that. Tell me how you started in this journey of real estate.

The Journey To Real Estate

I started in real estate about a couple of years ago. I was working a 9:00 to 5:00 job. I was working on a QuikTrip, which is a gas station, but it’s one of the nicer gas stations around. I was working my way up the ladder there, getting promoted, and all that, and I kept looking around thinking, “I do not want to do this until I’m 65. I do not want to do this until the age of retirement.”

I got on Google and searched, “How do I retire early?” Real estate investing popped up again and again. I found BiggerPockets and started reading stuff. I was 23 at the time and had not much money. I pursued the house hack strategy and bought a duplex with an FHA. I didn’t know anything at the time. I was driving around, looking at houses with signs in the front yard, and then getting on Zillow and clicking Contact Agent. I didn’t know that when you click Contact Agent, it’s not the agent listed in the house. It’s somebody paying for a lead.

One of the owners of the brokerage of At Home Wichita was paying for leads for a six-month period during that time. I was the only lead that converted into a sale. I connected really well with him. He was an investor. That was my criteria. Are you an investor? One of my other criteria is, are you younger? My parents used realtors who were all second-career realtors, so they were older people. I wanted someone young, hungry, and an investor. He met those criteria.

We were about halfway through that transaction and he had said, “Let’s go grab breakfast.” We go grab breakfast and he starts talking to me like, “Do you want to sell real estate? You do really well here.” I said, “I always thought about that, but don’t you have to be old? I’m 23. Don’t you have to be old to do that or at least to do well at it?” He was 27 at the time and a part owner in a brokerage. He was like, “No. You don’t have to be old at all.” He held my hand. He said, “You could also get your license to represent your own deals, waive your commission, etc.” I jumped in with both feet. That’s how I got my start with a house hack and then into real estate as a realtor.

You were able to complete that deal with that first house hack. Do you still own that?

I do. That is the best deal I’ve ever done. At the time, I felt like I was overpaying. This is pre-COVID and pre-pandemic prices. Here in Wichita at that time, I picked up a duplex and I lived on one side for $78,000. My cashflow is insane on that thing.

That’s great. You are an investor-minded real estate agent. I know you represent other clients, but how heavily do you deal with other investors?

If I was on a percentage basis, off the top of my head, I’m about 50/50. It’s 50% investors and 50% retail clients buying their first home or move-up buyers. The investor portion of this has grown over the years and has begun to increase more.

You not only list homes for those agents, but you help them find deals that are either on the market or otherwise.

I do both. I don’t discriminate. I’ll help buyers, and I’ll help sellers. In the past few years, I’ve gotten a lot of out-of-state investor clients looking to buy here in the Midwest. In Wichita, Kansas, we’re insulated from the super high gains or the very low lows. We’re protected from depreciation in that way, but we also can cashflow here. There are out-of-state investors that will contact me and then I’ll start going to different houses, whether that’s on-market and I’m doing video tours or I’m connecting them with other wholesalers in the market so that they can get a look at those off-market deals.

The Flip Talk Podcast | Jake Henderson | Real Estate Empire

Real Estate Empire: Jake Henderson does not discriminate. He helps buyers and sellers.


That’s a great plug for you. For those of you investors who are looking to be a little more passive and maybe don’t have the marketing stream or those systems set up, if you’re looking for some rentals that will cashflow, you can always reach out to Jake or agents like Jake who can help you identify those deals. I own a real estate firm. I am primarily an investor. In the 4 years that I’ve been in business, I’ve only bought 1 property off-market. We have access to four MLS’ and CoStar. We look at deals all the time. I’m direct-to-seller, so maybe it’s easier for me to do things that way. You seem to find these deals all the time. How are you identifying these deals?

I wouldn’t say all the time, but to always be looking is the main thing. I talked to other realtors in our market and they don’t want to work for investors because they think they have to work harder to get a deal or whatever. I’m still able to find on-market deals for investors. We use different strategies like long days on-market, and then also not being afraid to at least call the listing agent on behalf of my client and go, “I see this isn’t selling. What does the seller really need?” It’s not always the price. They might need something else. We can come up with something creative and get a good deal for both sides that way.

What the seller needs is not always the price. They might need something else. Come up with something creative and get a good deal for both sides. Click To Tweet

I love that. Money is not always the motivator. People have to realize that. They think, “How in the world can you buy a home with 70% of its value or 80% of its value?” Sometimes, people have other things on their minds other than the bottom dollar. Investors help people solve problems, and you connect those investors with those people. That’s incredible.

You worked at the QuikTrip. I’m very familiar with what the QuikTrip is. We have some up closer to Charlotte. If I’m ever there late at night, they’re a 24-hour store. What a transition. That should give folks hope as well. I want to dig into your mindset of grabbing your first deal and deciding to get your real estate license. Let’s put you in six months past that when everything starts to come together and you realize that this is attainable. Where was your mind at that point?

At that point in my life, my mind was going in a bunch of different directions. Part of that was, “When can I quit QuikTrip?” I demoted myself back to part-time and leaned into the real estate sales more. The other part I was thinking about was, “How am I going to get my next deal?” House hacking is great in that time of my life. I was single. I could save a lot of money. I wasn’t paying rent. My tenants were paying the full mortgage. All I had was an internet and electric bill. It was awesome. I was able to stack cash very quickly.

In month eleven of owning that property, I start calling lenders. I was like, “When can I get the next one?” I got a traditional loan. I used an FHA. They want me to live in it for a year after I own it. I was like, “As soon as that year is up, I’m out of here. I’m going to go buy another duplex.” I was doing that, finishing my degree online, and still working part-time at QuikTrip.

Somewhere in there, the girl I was dating at the time, who is my wife now, pushed me hard like, “You need to quit QuikTrip. You need to lean in.” There was this barrier or this fear of the unknown, “What if I don’t make a sale?” I didn’t have a full rental portfolio to sustain frequent income, so I was like, “What’s going to happen?” I was full of fear, and then she finally said, “You’re quitting QuikTrip or I’m out of here.” It was like, “You’re grumpy. You’re doing too much. Quit QuickTrip and focus on real estate sales.” She helped with that mindset to go, “I’m going to jump on both feet.” I’m so glad I did. I wish I had done it sooner.

That’s amazing. To have somebody in our lives who believes in us and pushes us is so important. I’ve heard some things about your wife that are great things. That’s a great story. There’s the theory of limiting beliefs. Sometimes, you can’t read the writing on the barrel from the inside of the barrel. It’s when somebody sees what you have and what you’re able to do. It’s somebody who sees you every day, lives with you, and knows your potential to stand by you and push you to do something bigger. She’s the real star here, isn’t she?

The Flip Talk Podcast | Jake Henderson | Real Estate Empire

Real Estate Empire: It is important to have someone who believes and pushes us.


She’s awesome. I love her. She’s great.

That’s awesome. You did finish your degree. You have a degree in business administration. Is that right?

Yes, but I finished online, which was way more convenient than trying to go to class, sell houses, buy houses, and all that.

Has that come in handy?

Not in a traditional sense. It has come in handy with understanding business to a better degree than if I didn’t have it, but I wouldn’t say that I would need that to do what I’m doing.

We’re dealing with some of this with my son who is turning seventeen. There’s this big discussion of whether or not to go to school and what to do. He has an idea of where he wants to go in his life, but that could change pretty easily. My take on education is it shows perseverance that you finished that degree. You certainly built something and built some integrity by doing so. It brought value to you in that sense of the word. As far as your rentals, you’re doing some short-term, some medium-term, and some long-term rentals. Is that correct?

Mid And Long Term Rentals

I was doing short-term rentals very briefly. That was not my bread and butter. I didn’t like the amount of work put into that, so I switched those to midterm. Midterm and long-term are my strategies.

What does the midterm look like?

Midterm is looking great. I converted each of those duplexes that I own. The one-bedroom side is great. 1 and 2 bedrooms for midterm have been great in our market. I started those in November of ‘23 and I’ve had 1 week of vacancy since. To compare some rent, those were renting long-term for $625. Now, they’re renting $1,295. I’m paying utilities and still paying a professional cleaner when they leave, but I’m still at $1,000 after utility. It’s a much better cashflow.

What type of client are you renting those to?

Most of the tenants I’ve had are traveling nurses. I got hit up by a pastor who’s trying to bring someone who’s going to be here for nine weeks that is training. It varies a lot. I’ve talked to other people owning midterms. Here, Boeing is a big deal, so there are Boeing employees who are contractors who don’t really want to lock in a long-term lease but who are good with midterm.

How are you acquiring those tenants?

On Furnished Finder. On Furnished Finder, I’ve had really good success. It’s a great website. They’re working on making it better, but it’s like Craigslist was back in the day. It’s a place to put your stuff up there and then other people hit you up. They’re not like Airbnb or VRBO where they control what happens, the booking, and all that. You take all that off of the platform in order to handle that.

That’s great. I’m going to switch gears here a little bit. I want to talk to you about some of the real estate agent aspects of what you do. I was listening to Jim Rohn. He said, “Many of us don’t get paid for our time. We get paid for the value we bring.” I want to hear you talk a little bit about the value that you bring investors other than helping them find deals. I know there are some different aspects. You’re helping them not to overpay. You’re helping to advertise the product. You’re helping to advise them there. There are all sorts of aspects to being an investment-minded real estate agent, and you’re really good at that. I want you to tell our audience what value a good real estate agent brings.

Many of us don't get paid for our time. We get paid for the value we bring. Click To Tweet

Thanks. Let’s talk about the buy side, and then we can talk about the listing side. That might be an easy way for my brain to separate this. On the buy side, finding deals is huge. That’s a huge value. There are little things that an agent could do to bring more value to you as you’re looking for properties. One is they should be pulling comps every time before you write an offer.

You’re going, “What’s a realistic and conservative after-repair value for this property?” Whether you’re buying it to buy and hold, flip it, BRRRR it, or whatever you’re doing with it, you need to know what it’s worth after you do what you’re doing to it. I always do that. Another thing is connecting you to other local contractors that are investor-friendly. What I mean by that is they’re good at what they do, but they’re not charging huge premiums.

Recommending Contractors To Clients

I want to stop you there. That’s a whole point on its own. You have those contacts. This contractor game is interesting. I made a joke that I wouldn’t refer a handyman to my best friend because I hold my word so dearly. Folks are always recommending contractors. They may recommend them after they’ve done a very small job for them and they may have had a good experience.

You come from a real point of context in that these contractors that you’re recommending, you’ve seen them perform time after time. In really good faith, you’re able to recommend those contractors to your clients, and they may otherwise have hired the ugly duckling 4 or 5 times. Finding the right guy who understands what it takes to work with an investor on the contracting side is not an easy thing to do. Talk a little bit about that and then we can finish up your point.

With contractors, my name’s attached to that. That makes me look bad. I might lose that client if that contractor does them wrong, doesn’t do it right, screws them over, or whatever happens. What I do is I am always plugged in with other investors who are doing a lot of volume in the community here to talk to them about who they are using. On my own projects, who do I like using?

Communication styles, when they get paid, and good work is a requirement no matter who I’m talking to. It’s these nitty-gritty details of, “Are they communicating what’s going on? Are they asking for payment before work is completed?” By me using them and then close friends of mine in our community here are also using these people, that’s the only way I’m going to recommend somebody. I will be honest. Sometimes, somebody’s great, and they’ve been great for three years. All of a sudden, their business changes. I don’t know what it is, but they start flaking, stop picking up the phone, or whatever. I’m always hunting for new contractors because it seems to be necessary.

I love that point. There have been guys in my past that something happens. Sometimes, life happens. Sometimes, you overextend yourself. We deal with that as well as in our businesses. That’s a great point. As far as deposits and communication, which were two points that you mentioned, that’s so important. You don’t want to get out there with a contractor and pay him for half the job and the material that he hasn’t completed. That could cost you a lot of money.

Learning lessons on my own as a newer investor, I’m not afraid to share those stories with people about, “This can happen even if you’re smart. If you think you’re so smart, this can happen to anybody, so pay attention.” Run your business like a business.

The Flip Talk Podcast | Jake Henderson | Real Estate Empire

Real Estate Empire: Pay attention and run your business like a business.


Communication is so important. It’s so tough sometimes with contractors. They have a lot going on and they’re from job site to job site, but an update is so comforting to know that your job is progressing. That’s important as well. Continue with your point.

There are other clients that if they’re out of state, be boots on the ground. There are some agents that are like, “I’m going to write the contract and negotiate that. That’s my job. You close and handle all that.” These people that I’ve built a relationship with, other investors, they’re either buying to hold or buying to flip. That entails progress updates.

If they’re out of state, they don’t know if their construction is going as well as it should be or as well as that contractor’s painting it. You can take a photo of the tile work. It might look good in photos, but in person, you can tell it’s not right. It’s being boots on the ground going and checking on properties. I’ve partnered with wholesalers not officially, but like, “When we flip stuff, we’ll use you to list it.”

Sometimes, I’m running lockboxed or meeting a seller because they don’t have an e-signature or whatever that is. I do those little errands that I can help alleviate some of their stress, especially for out-of-state folks, but even for our local people. They might be working a 9:00 to 5:00 job but don’t have time to go check, meet somebody to open the door, or whatever. That is huge on the buy side and also when looking at rents. I’ve run into this. The past 2 or 3 out-of-state investors that have hit me up are like, “What are rents?” It’s analyzing rents, not just after-repair value, but, “Is this going to cashflow?”

You have true experience with that because not only are you an investor yourself and you know what the market looks like from that perspective, but also, you’re dealing day-to-day with the other folks in your office. Those folks speak very highly of you. One of them tells me you are a stud at your job. There are softwares out there that gives you a general idea of what you might anticipate receiving for rent on a property, but you really know firsthand.

It’s the same with if you’re going to exit and you’re going to flip. It’s not just telling you, “It’s going to be worth this when you’re done,” but, “How long are you going to probably hold this thing? If we list it, what are the average days on market for that neighborhood?” That way, before they even know if they’re borrowing private money or whatever they have, they know their cost is going to be a little higher if it is going to take longer. It’s the details.

Have you sold any of your own properties? Have you done some flips? Have you let go of a rental or any of your own properties?

I did one flip. I was in my second year as an investor and as a realtor. Another realtor in my office, a good friend of mine at that time, hit me up and said, “Do you want to flip a house? I got this deal. I got this lead.” It was pre-market, but they had already signed a listing agreement with a listing agent. We walk through it and go, “Let’s do it.”

We were under contract and then the pandemic hit. We were newer to this flipping thing. I only have two duplexes. I’m thinking, “Should we bail on this contract?” Ultimately, we decided to move forward. We bought deep enough that we were like, “We’ll be fine either way.” We didn’t know. I don’t know if anyone knew that the market would shoot straight up. It was awesome.

Where I was going with that question was whether you listed your own property and whether you would list your own properties in the future. I know there’s a bit of a conflict of interest listing your own properties as a real estate agent. We have disclosures that let people know that the property is owned by an agent. That’s how it’s handled properly, at least in North Carolina. Did you and and would you list your own properties in the future?

We did. I would think we co-listed it. I let him take points. I was like, “You found the deal. You take a point. Get more MLS credit.” We did list it. Whether you’re an agent, a flipper, whatever, in my mind, it’s always integrity. If there’s something wrong and you know it’s wrong, disclose it. It’s going to cover you in the future. You’re not going to have crazy lawsuits coming back at you or whatever. Over-disclose. It also puts buyers at ease if you’re being detailed about your disclosures.

The Wedding Day

That’s so important. If you’re honest and straightforward about your properties to the best of your ability, that takes care of any liabilities that you might face or at least limits them. That’s great. I know you personally, and I know you’re that kind of person. That’s why I have you here. I have a couple of personal things here. Your wife had a little bit to do with this. We have mutual friends, Cassidy and Ely. Talk about your wedding day and how hot it was. There’s a funny story behind that. I’d love to hear that.

Did you contact my wife or did Cassidy?

Cassidy made some phone calls, so I don’t know. She reported it back to me. I’ve got sources. Let’s put it that way.

That’s great. She’s well-connected. We decided to have a summer wedding, but we thought, “Let’s be smart about this. Let’s do this in the morning. It’s going to be outdoors and a smaller ceremony.” The pandemic was still going on, so we wanted something a little smaller. There were up to 50 people. We’re at a local park and all that. Early in the morning, it was great. By 10:00 AM, it was hot. I don’t know the temperature. It was probably close to 100. Here in Wichita, our humidity was pretty high in the summertime.

During our ceremony itself, I’m standing up there and I’m full of emotion and all this other stuff but also wearing formal clothing. Me and Madeline’s back is to the audience. I can feel sweat forming on my butt. It’s forming and slowly dripping down my leg. I was thinking, “I hope I don’t have a swamp butt right now,” but there was no choice. What do you do? You stand there and let the ceremony finish. I asked a few people afterward, “Did something sweat or anything weird?” They were like, “No.” I’m like, “Good.” I didn’t know if I could have prepared for that better. Is that the story you’re poking at?

Absolutely. That’s funny. Speaking of being wet, I love that you brought up the Quiktrip thing. We’re here to motivate folks and to let them know if they’re in a job like that there’s nothing wrong with that. If you want something different or want something more, it’s possible. For some context here, I was told that you had an old car where the passengers would get wet every time they rode in it. What was going on with that?

Are we talking about the Dodge Neon? At that time when I bought the duplex, I was rocking a 2005 or 2007 Dodge Neon. It was a clunker. It probably would’ve qualified for cash for clunkers back in the day, but I didn’t have any need for anything fancier than that. I was going to and from work and to and from projects. I never found the source of the water, but anytime it would rain, I don’t know if it was getting to the doors or something, but the floor would feel wet.

I got great use of that car. I sold it for what I paid for it. I do remember thinking, “I probably need a better car,” so I upgraded by buying my dad’s vehicle, an old 2012 Ford Escape. I wonder if this is the one you’re talking about. If I run it through a certain car wash in town, I don’t know if it’s the angle that it was spraying at or what, but water would come through the sunroof. My passenger would get soaked.

It sounds like you’ve made a lot of sacrifices. That goes to show some agents. Some agents think they have to drive a Mercedes around to get deals. I bet you found a lot of deals during the time you were driving an old car. Here is another thing. I can remember during my first flip, I had very little money in the bank. There was a $12 Cubs hat that I wanted, but I wouldn’t even go buy that. It’s a delayed gratification thing. You seem like the type of person that makes sacrifices for your future. Am I right there? Did it take you a long time to upgrade the car to something nicer or newer?

Yes, even the Ford Escape. As a realtor, normally, I don’t have passengers, so I was fine with it. It looked all right from the outside. It was a car. My wife helped push me into that too. This past fall of 2023, I owned that car for seven years.

What did you buy?

I got a Honda CR-V Hybrid. At that time, I was thinking, “I want something flashy. I’ve earned this.” More thinking about that and then thinking and talking to my wife, I’m like, “Maybe I shouldn’t do that.” She was like, “Why don’t you get something nice, clean, and has good gas mileage?” I’m like, “You’re right.” I got a new Honda CR-V Hybrid and 40 miles a gallon. I’m really glad I got that. It saves me a lot of money on gas.

Jake’s Goals And Dreams

It took you many years to get to even that point. That’s important for new people to understand. Sometimes, we have to delay these things and put our money back into our business and our time. That’s so important. One of the keys to my success was not focusing on those material things at first and trying to dig in and put everything I had back into marketing. That’s how I built my business. With that said, what does your future look like? What are some goals and dreams that you have over the next few years and then in the long-term?

In the next few years, I want to continue to buy rental properties. I’m not focused on flips. I truly favor rental properties for the tax benefits. As a full-time real estate professional, being able to offset taxes for my active business as a realtor is a huge advantage. That’s my focus there. On the real estate sales side or the realtor side, I want to build a team. What my vision is is a smaller team of 4 to 5 agents but highly productive agents. It’s me and I have one team member who started in February 2024. She is killing it. She’s very coachable. She’s learning quickly. She’s already making a lot more sales more than I did when I was a new agent.

As a full-time real estate professional, offsetting taxes for your active business as a realtor is a huge advantage. Click To Tweet

In the long-term, do you have a goal or something that maybe drives you?

Being married with no kids, my goal has long-term changes all the time because I feel like I could do anything. What I’ve been thinking of for a long-term goal is to someday have a family, have kids, and then build something where I teach them work ethic, how business runs, and how to structure things. I like teaching, and I feel like I’m going to love teaching my own kids. I’ll be teaching them all that so that I can leave a legacy that they don’t squander. That’s a broad generalization. It’s weird to have motivation for kids that don’t exist yet, but that’s my dream.

You’re building this team. I’m sure you’re going to make a great dad. You may not give yourself credit for it, but you are a real estate coach and a motivator. I love to see your growth. You’re an incredible person. We hit it off the first time we met. I know more people in Wichita than I would like to know, but the people around you speak so highly of you. Your business is going to continue to flourish and so is your personal life. I’m so grateful to have you on. Tell everybody how they can get in touch with you so you can find them that deal of their dreams.

There are several different ways. If you’re on BiggerPockets, you can search my name, Jacob Henderson. I’m a featured agent here in the local area. Facebook is probably my second best way. Search Jake Henderson, Realtor. Once I have a team and it’s branded, I’ll update that, but this time, it’s Jake Henderson, Realtor on Facebook. Get on AtHomeWichita.com. You can find my profile there with my email, phone number, and all that jazz. You can text me anytime at (316) 650-0372. Don’t cold call me.

You know the man is hungry when he is giving you his personal mobile number on a nationwide podcast, so reach out to him directly. You can’t go wrong with Jake. He is one of the best realtors I know. He follows the rules. He works his butt off, and I’ve seen it firsthand. Thank you, guys, for joining the show. Go to FlipTalk.com for all our new episodes. We will see you next time.


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