Episode summary
In this episode of The Roots Podcast, Max Moore and Tyler Lingle dive deep into Trent Kiester’s inspiring story, how he went from working as a barback at a golf course to buying his first investment property with just $10,000, all while becoming one of Indy’s top-producing agents. From overcoming fears and leveraging house hacking to building long-term wealth and adapting along the way, Trent shares the exact steps and mindset shifts that made it all possible. Our mission is to help you plant roots, build wealth, and grow in every area of your life, and this episode is no exception.
Ready to take the next step? Follow the plan below:
1. Stay in the Loop
📩 Newsletter: Join the Roots Newsletter
📺 YouTube: Subscribe to Roots Realty Co.
🎟️ Live Events: See Our Upcoming Schedule
2. Get Expert Advice
Ready to talk strategy? Book a free intro call with us:
Book with Max: Schedule Here
Book with Tyler: Schedule Here
3. Get Matched with an Agent
Looking to buy or invest? Let’s find the right partner for you:
Disclaimer: This video is for educational and informational purposes only. Nothing in this video should be construed as legal, tax, or financial advice. Always consult with licensed professionals before making any real estate investment decisions.
#IndianapolisRealEstate #IndyEntrepreneurs #RootsRealtyCo #TheRootsPodcast #CommunityOverEverything #RelationalEquity #FaithAndWork #IndyInvestors #MidwestLiving
Chapters
- 0:00Intro and Trent’s transition from barback to investor and top selling new agent
- 1:50Trent’s biggest fear before buying his first investment property
- 3:50Trent’s strategy and journey to purchase his first real estate investment
- 8:15Breaking into real estate investing requires a hunger for learning
- 9:45Tyler’s agent perspective on Trent’s first deal
- 12:19The importance of decision making and leveraging relationships
- 17:35Tyler’s three steps to building $1M net worth before you’re 30
- 18:36The differences between being a real estate agent and wholesaling
- 26:16The philosophy behind Trent's first house hack
- 35:52Life lessons that changed Trent's his day-to-day
- 41:43Finding tenants while under contract
- 43:33The Reality of Cash Flow and the Pitfalls of Short-Term Rentals
- 47:15Subsidized Housing & Section 8, Cash Flow Strategies, and Turnkey Deal Management
- 52:12Trent's go-to Indy food spot
- 52:55Trent's #1 habit that changed his life
- 55:44Where Trent is currently trying to grow in his life
- 58:00Wrap Up
Full transcript
Auto-generated from the episode audio. May contain minor errors.
i didn't have money at the time i remember looking at my bank account i had finally managed to save up $10,000 through barbacking and serving you can get in all the forums you can talk to all the people find all the mentors but you have to do the thing to actually learn what it's all about house hacking as being the most powerful vehicle in real estate investing but frankly I wasn't confident in my ability to make that payment on a monthly basis welcome back to another Roots podcast i'm here with my co-host Max Moore i'm Tyler Lingo we are the founders of Roots Realy Co and we're here to dive deep into real estate Indianapolis and building wealth i'm here with Trent Kester trent and I go back to his early days in real estate which weren't too long ago not too long ago yeah so Trent joined the team in early 2024 so about a year ago just over a year ago and he has done over 40 deals as a real estate agent eclipsing 7. 5 million in transaction volume which for reference puts him in the top 2% probably of new agents top 1% top. 5% of new agents like he's just dominating the real estate agent scene focuses primarily on investors but actually Trent and I go back to before you were an agent uh your agent was me uh for better or worse and we actually met i remember you were working at Back N golf course managing serving tables uh not at all in real estate and then you called me up and you had a very specific need you had this little triangle you wanted to buy a home in and I was like "This guy has done his homework but like is that little triangle in that buy box like really the right one?" I kind of poked and prodded at it and we got out and saw homes and you ended up buying a home which we'll get into that story but the question I want to start off is before you had purchased your first investment property what was the biggest fear in that process like what was the like thing about like oh I might I might go and mess this all up like what was it what was the fear you had to overcome in that yeah I'm I'm sure at that time there were quite a few um and I think it it all stemmed from a lack of knowledge I think at the time um and so uh being in college I wasn't necessarily exposed to a lot of the information that I probably needed at the time to be able to to do that successfully and so I think the first hump for me was number one deciding that it was something that I was going to do um not something that I wanted to do or something that I fantasized about doing um but deciding that that was the goal and I was going to accomplish it no matter what it took to get it done um for better or for worse like you said um and so that was kind of the first thing the second thing was was getting the information um and I had to find it somewhere so I think I actually found you through Bigger Pockets funny enough um we do a lot of our marketing through Bigger Pockets now um and so I started doing research on there getting into forums watching YouTube videos doing the thing um and uh that was all super helpful um and what I learned and we talk to clients about this all the time um which is you can get in all the forums you can talk to all the people find all the mentors but you have to do the thing to actually learn what it's all about uh and how to do it the right way and so um I think you know beyond um trying to learn one specific thing or trying to meet one certain person uh to try and accomplish the goal it was more about just doing it uh and so that's why I called you that day because I had taken in all the information that I possibly could at least all the information I thought I could possibly take in uh and it was like I just need to go make the move so let me let me call Tyler you were the first person that popped up like on the investor agents so you were the only person that got a phone call you answered the phone and and you were the guy I went with so Well I love that cuz you just gave the blueprint which is uh surround yourself with other people who are doing it like you started with the right network and the right people around you which led you to that next step of find a trusted guide and agent so surround yourself with the right people uh immerse yourself in like the culture of real estate find the trusted guide and jump off and trust the process right you could have easily sat behind dozens of spreadsheets and YouTube videos and never made a move and in fact many of the people we talk to or don't talk to sit behind in that trap of fear um so I love that what were you kind of break down what you um what your strategy was with that first home i think this is interesting a lot of people who are either going to house hack um buy their first investment property what was your strategy what did you uh actually end up doing and what did you learn i know it's a big question but No it's it's a great question uh we talk about house hacking as being the most powerful vehicle uh in real estate investing for both young individuals and super experienced people alike anybody can utilize that um gateway uh into into real estate um and that's exactly what what the plan was um I didn't have money at the time i remember looking at my bank account uh I had finally managed to save up $10,000 through barbacking and serving and and managing and doing whatever else I did at back n um but frankly I wasn't confident in my ability to make that payment on a monthly basis and it's funny I I remember I called Rocket Mortgage cuz I I c I tried to like get pre-approved before I talked to you which was a crazy bad idea but anyways I remember being on the phone well you wouldn't have known like you didn't know the process only the agent refers the mortgage lender right so anyways I remember being on the phone with the lady on Rocket Mortgage that night it was probably like 6:00 or 7:00 p. m i I don't know if they like were answering the phones later or whatever but anyways she was uh she was like "Yeah I can get you preapproved but like are you sure you want to do this cuz like I'm looking at your financials i know how much you make like are you sure this is the right thing for you to be doing?" Uh and I was like of course I told her you know yes you know it's good you know I'm fine um but in the back of my mind I knew I'm like I have to find a way to rent out some of these bedrooms uh and the interesting thing about it was I had to have my dad co-sign on the loan um and when you start digging into FHA and and what they allow if you have a co-signer on an FHA loan and I don't know if this has changed so I encourage everybody to go talk to their lender about this but at that time um I had my dad co-signing and if you want to buy multifamily with an FHA loan you absolutely can do that you can buy up to four units um but if you have a co-signer the co-signer has to live in that house as well if it's more than one unit uh and so I went into this uh you know house hack journey under the assumption that I'd be able to buy a duplex and live in one side and then rent out the other side to you know cool if it was a friend but if it needed to be someone that I didn't know awesome um I came to find out that I could not do that because my dad was not going to be living in the duplex with me uh so I had to buy a single family home which kind of changed things a little bit because I don't want you know a random person living in my house with me it's not ideal um so anyways I say all of that to say um I had to buy a single family home and so the conversation then became well who do I rent this bedroom to uh and so I remember going back to work and kind of just like sharing with everybody hey this is my story this is what I'm doing i'm getting ready to buy this house uh here and I'm going to be looking for a roommate uh and I was you know working alongside um one of my friends at the time Evan who's still a friend to this day um so Evan if you're watching thank you for being a part of my journey and helping me but anyways uh Evan was like yeah Evan was like "Yeah my my lease is getting ready to uh you know to run out i'm looking for a space to live like I' I'd love to live with you." Uh and so I was able to like kind of make that work but I should point out that um I am very fortunate and very lucky that I was able to do that um because if I couldn't find somebody to like live in that extra space that I had in the house I would have been having to make the entirety of that payment uh alongside the slew of u you know renovations that I chose to to do which we can also talk about cuz I know it's important um but that was kind of like the thing for me it's like I got to find someone and I did so um I want to bring it all back a little bit to make it more digestible for the person that's sitting here right now going I want to buy i have no idea how to buy and looking for like the the first launching off point so it became an obsession about houses and investing through the people that you were surrounding yourself with as well as bigger pockets getting more information deeper you got in the forums the more you're like I want to be doing what that's guy's doing and then it became an independent journey of research going to the lender going out going "Oh here's one objection let's get over that wall here's the next objection let's break through that wall." It wasn't Tyler saying "Come on buddy brick wall smash you through it it actually was you going out to the lender like Tyler probably just learned for the first time the FHA co-signer if you have to go single family and he was the agent on the deal because Trent embodied something that uh the people who do transact all have one common uh trait and that is that they are hungry to close the deal it is not the agent's responsibility to get you to the finish line it's our responsibility to get you to the finish line with a discernable um uh inspection process and a smooth appraisal process in one piece to get you there in one piece peace of mind and to get you an investment that you can do what you did so you were 19 at the time just turned 20 I think yeah just turned 20 just turned 20 working as a barback/manager at a golf range essentially range uh should probably shouldn't have done that i remember thinking I want to give a little bit of agent perspective that as it relates to people i remember that seeing your pre-approval which was like 130,000 or something it was like rocks it I literally was like I would give him a 5% chance of closing but maybe in 5 years he'll come back to me and actually close on like a Brownsburg house in 250 right but his eagerness and his what he did he showed that he was doing the work even if he was doing the he hired the wrong mortgage lender um you know was looking in a tiny pocket that had two homes for sale that were both distressed so he showed that like he was willing to put in the work and put himself out there and you were also open to evolving like you switched from the the duplex to the single family home you opened up to other parts um like we started looking in that third what international marketplace neighborhood what's the name of that um Eagleale eagle yeah we and we're like this is not you don't want to be surrounded by um you know all this like crazy stuff happening in this neighborhood so ended up like expanding outwards and figuring out Riverside was actually your your real target and I think you kind of retargeted towards Riverside i did yeah so you iterated along the way which I appreciated even though you know when we were looking there was literally on our search like at one time three homes that actually were like livable yep that's where we're going to see him right that's the show that we're booking it was obvious choice the adaptability of a first-time home buyer is huge because you don't get your dream home you get the home that provides you solace it provides you a place to lay your head so that you can grow with the home right and why do we not rent well it's to own our own space and it's to grow for you why did not rent well you didn't want to pay the landlord you want to be the landlord you want to be the guy that was becoming uh unlocking the ability to build wealth which is everybody in our network that wants to house hack and they all just have that one trait that they are able to go run through every brick wall that and and be that like flexible adaptable person mhm i think that's like the misconception house hackers the people that don't get to the finish line are the ones that call me and they have the same exact problems that you do they've got 10 15K and they're like I don't want to go rent somewhere and I need out of mom and dad's bedroom or mom and dad's bedroom mom and dad's basement hopefully not their bedroom right and to get there they have to do some work right you're buying a house you're not you it's not a olive cart service I think is is the the biggest sentiment that I'd love people to hear yeah and this is what I think is the the great tragedy I think in our space uh and in many entrepreneurial spaces just in general is that a lot of people um have this assumption that things will just happen for them and that they're easy you can go watch a YouTube video you can go watch a house hacking YouTube video and someone will break down the whole process for you in 5 minutes and you'll leave out of there so galvanized and ready to go you're like "Oh this is great like let me just go do this." Uh what people need to understand is that you are making a big decision and you have to be the principal decision maker uh when you're like you have the full liability% water heater brakes it's on you brakes it's on you 100% so you have to get understanding what that cost looks like well yeah and I think the one thing that separates you from many others that didn't get that first deal done that are still renting cuz I know many of them um there's dozens of friends even that know real estate is you got in the car with the people who were uh drivers as in like you got you knew some indie car drivers people that had done wholesales flips apartments and you approached them and they were willing to help they were like "Yo you want to learn how to do this i'll help you." In Indianapolis you can actually do that because we're the most relationally accessible city in the nation in some cities you can't but also with me you had enough trust to know okay I you know I'm not going to be sold a property for showing like I can actually have a conversation with this guy leverage some of his experience cuz I house hacked with veterans as well and that eb and flow of the conversation it's the ones that actually do that with us that end up buying 10 versus the ones that sit on the sideline cuz they're closed in yeah and they're isolating themselves and they only have this much knowledge in Acorn which is their own because they're not opening themselves up yeah and we need to stick on that for a second because what you just said is very powerful uh and that was a big piece of my story so I think um what I got in the habit of doing was I became that guy that went and watched the YouTube videos and thought that I knew everything um and that's probably part of the reason why I didn't go to a real estate agent first i was actually planning on doing something similar to what I think you did with your you bought your first house by Right you're like "Yeah let me just go do it." Let's start yeah yeah um and so Bank of Meridian Title Company baby no home inspection no appraisal either it's not crazy chase that's crazy not for them but anyways I became that person that thought by digesting the material that I found on Bigger Pockets and YouTube I could do everything myself uh and I quickly learned that that was not going to be the case and the reason I said I want to stick on that topic for a second is because um like you mentioned I was working at Back N at the time um and I didn't start working at Back N because I enjoyed golfing i had never swung a golf club before I started working at Back N uh I didn't really even want to work in Indie frankly i I lived on the west side still i probably could have gotten a job closer to home the reason that I got that job is because I knew that I needed to meet someone in the space who was much better at doing what I wanted to do than I was um and so I told myself I said "What's the best way I can do that?" Uh well I think a lot of rich people like to golf uh I'm sure some of those rich people probably own a lot of real estate uh and if I can get behind a bar and overhear conversations maybe I can find myself in one of those conversations and meet someone and make a friendship uh and that's exactly what happened um I remember being behind the bar one day cleaning the little glass polishing the little glass whatever uh and uh two two mentors I still have to this day came and sat down at the bar and I overheard one of them talking about um a flip that he was doing in Fountain Square and he was talking about doing a carriage house and this and that i didn't know what any of that meant at the time uh but I I literally just budge I went straight into their conversation i'm like "Hey like I've been trying to wholesale a deal in Fountain Square for like a year now like "Can I listen in your on your conversation like I'm super interested in this." Uh and they were more than happy to talk to me and they were excited that I wanted to listen um and so that was like that it was like that moment i'm like "Holy crap it worked i met somebody." Uh and from that day I learned the power uh of being in rooms uh with like-minded individuals that you strive to be more like uh that is extremely powerful uh and it took me doing it to to really learn that lesson but um that's why I love like when you said that um cuz that resonates with me i I I did that well I think if you put uh one person in a room with 10 people that own more than two doors that person inevitably like within six months will own a house like put a renter in a room with two people that or 10 people that have a portfolio there's no there's no doubt in my mind which kind of is like what happened because you became obsessed with the shiny object but then actually putting like some tactful nature to okay I'm gonna go pursue a relationship it's I've said it on this podcast and I'll continue to say it until I'm in my grave the greatest wealth that you can have especially in this city is to go have coffee with somebody tomorrow morning ask them who they should have coffee with next go have coffee on Thursday on Friday on S and have 10 coffees a week and the wealth of knowledge that'll pour out from that double degree that's the first step like of my three steps to building to $1 million net worth before you're 30 which I'm coining uh for everyone here uh is one networking tree do 50 coffee meetings at the end of every coffee meeting ask who else do you know that I should meet two house hack buy your primary residence do it two or three times if you can before you're married and have kids um or after and then three is learn how to leverage other people's money and you'll that's my story right that's how I found a million dollars net worth similar for you um and how you get connected to Tyler to go on that journey is step number one you book a call step number two you come to an event and step number three you call him back with a freaking pre-approval and you go buy the follow yeah you got to just stay half the battle is staying in the game and not giving up and making relationships that keep you motivated to stay in the game cuz you can't do this alone right it can't be just like we say it can't be just numbers spreadsheets and random listings that you're just not going to have the juice um you mentioned something which was you were trying don't worry I'm not going to talk go down this rabbit hole of wholesaling but you mentioned that you're trying to wholesale i do want your perspective now as a re a real estate agent a young 22 year are you 22 22-y old real estate agent who is having a good amount of success in a tough market in a very u low transaction count market what is the difference in your brain uh what are the key differences between being a wholesaler and trying to like cuz you see all these armies of people trying to wholesale to break in it's like stop number one on the train like I want to get in real estate oh I'll wholesale had an call on Monday hey I'm moving to Indie i want to start wholesaling before I get there in October i said that's great don't want to discourage you i have nothing for you i have absolutely nothing we're building equity but when you do in October when you arrive here in October whenever come to our next event that's what I can bribe yeah so where I'm going with that I want your perspective on being an agent versus wholesaling key differences and are you happy with your path going down the real estate agent route yeah um I'll answer the the first question first um the reason wholesaling is so popular is because it's the lowest barrier to entry into our space right you don't need a scent to get into wholesaling um you can go knock on doors and find someone that wants to sell their house for less than it's worth tomorrow if you want to and you spend enough time doing it uh and so I don't think that um that's a bad idea per se for some people um if you're super interested in that and you like the idea of really getting in the dirt and looking at lots of deals and analyzing lots of deals and that's just the way that your brain works and you're good with talking with people um and you're solutionsoriented and you like helping people find solutions uh when they're in difficult times which is pretty much what that space is all about um I don't think that there's merit in totally writing that off like I think that there's um there's value in that um maybe not to the extent that people draw it up to be um but there's certainly value in that and I don't think it's a bad thing i'm not traditionally wired that way and I think I quickly found that out when I tried doing that um I like making an impact with people who I can create true relationships with and I think that's what being a real estate agent allows me to do a little bit better uh than maybe h you know how wholesaling would have allowed me to to accomplish that goal if that makes if that makes sense i think it becomes a little bit more transactional is I guess what I'm trying to say it does and we had Evan Manship on here and he defined wholesaling as the pawn shop and he said the pawn shop's dirty the pawn shop yeah i'm not going to meet my best friend at the pawn shop right right no I'm going to the pawn shop because I'm in dire need and we're like the steakhouse you go to the pawn shop or you go roots realy agents we're like going to the steakhouse yeah we're like the cruise ship yeah we're the cruise ship jump on board and we'll take care of you right um analogy but I'll just leave it i'll drop it but I want to go from uh this house on Mansfield that you bought and compare it to if you would have gone down wholesaling so in that first home what month did you close on that in 2023 right june or July yeah okay so June or July in September you call me and you had you had something to wholesale you called me with a deal to wholesaler you said "I need you to help me run comps on this how much can I sell it for and do I have to do anything to it?" And I got on there and I was like "Uh Trent I don't know if this is a house like anymore." And you like you're like "I'm standing in front of it it's a structure i can sell it." And like I feel like the number was under 20,000 that you could have gotten this house for and I could be wildly wrong but it was like I was like you you'd be better off getting dirt at this rate that you can't sell that anybody it might be negative to have you yeah that's what I was saying it's going to be He's got he's got a demo on it and everything yeah it 100% was going to be and so he calls me on like a Monday i kind of throw him off on a Tuesday he calls me back and he's like "No seriously i want to buy these can we buy these together and flip them and you're wholesale?" I'm like I'm like "Just go get your real estate license what are you doing?" I'm like "This deal is not it it's not what you want to do." I think you did end up putting an offer in and lost because of how like a month later you were in your class yeah literally you were like "All right I'm going to go get a real estate." the people that I meet that are like trying to one day they want to be an apartment owner they want to be the flip you know killer whatnot and they're trying to do this crap you know they're trying to resell homes on Zillow and I say "Dude just go get your your license and be an agent if I can tell they want to bring value to people authentically they're enrolled the next week that's why we have way too many real estate agents in our market." But that was the phone call right the phone call wasn't "Max I want you to buy this dilapidated house with It was like "Hey I know I saw you at Back N a month ago after closing on this house with Tyler cuz Tyler was like "Hey had this first- time home buyer i think he was you know really cool really led the journey himself i want you to come meet him." I like pulled up to Back Nine and we golfed together with your friend with your mentors that you had met there and a couple months go by and you call me saying "I remember you saying you want to flip here's this." And I think I might have been the only person on that list of like potential that could buy the house from you in the wholesale scenario list which was admirable right and like the value that he was pitching i there uh something came over me that said this guy should just be a real estate agent and I just said it and then you did you took action and just showed up on our team like by January and now building block of the business it's crazy the there's an important thing there that I want to hit on a little bit further which is in our space and once again I'll use the entrepreneurial space as a whole it is very hard to fake it uh in what we do uh and you will get exposed quickly if you don't know what you're talking about and so um I think that shows itself to be true in the wholesaling space so for example you talk to guys like Evan or maybe you'll talk to Ben uh someday um or you know some of these other big wholesalers whatever uh they do what they do at a very high level and they're able to provide a lot of value because of it and because of the amount of value that they're able to provide to the number of people that they're able to provide that value to they make a killing uh doing what they do there's no in between frankly I'm just going to be honest there's no in between you either crush it or you don't lightly push back i don't think they know that much about their actual properties they're selling i think they know emoticum i think they know a whole lot about operational success in lead generation and now hiring and firing people they do know that [ __ ] pretty well about hey are the utilities on at this property don't even ask they don't know yeah they don't know the address they don't That's not the million dollar answers they need to provide right it's how do you keep a guy cold calling on your team here's the question I go back to to you who is like "Hey I want to go wholesale and I want to go do this how are you going to compete with a behemoth of that caliber right and they not already have reached them right ben's already talked to him ben's talked to him four times in fact they should just if they really really want to they should just go work for him or work for an entity like a real estate developer or Roots Realy we we've had positions open a guy that wants to get some real estate is going to be our admin right like work for one of them until you have the runway after you house hack to get that first investment but the runway in real estate we could have a whole podcast about how to break how to get runway in real estate it's right especially how to become an agent million different ways how to become an agent how to make money i want to go back to that first house though to talk about wealth which is a much deeper rooted conversation and really break down the wealth and one that house hack that was kind of an accidental right not really 10k in the checking account is what you said i have no idea how I'm going to pay this mortgage fund so I have to identify a tenant before closing um you also mentioned some repairs there we don't have to get into like crazy it was a piece of crap it was $125,000 property like it didn't have central air you learned what central air was when I met you I had to explain to you what the different type of heat sources could be in a house yeah i remember and I was like who is your agent you're like Tyler that's how I met you i'm like well this guy even even worse it's a $100,000 house i I remember walking the house with you and you you pointed out the furnace in the basement saying something the effect of like this looks pretty old i would plan on replacing this at some point i didn't know what a furnace was i didn't know that that's the component that helped keep my house warm in the winter um so that's where like that was the level I was at at that time it's not that it wasn't there you did your job you you did your job very well had no idea yeah i had no idea well yeah and in hindsight you probably would have negotiated right and this is even I was I'm probably on year two of being an agent so by the way I probably would have handled it differently now than I did back then and you would have too and we possibly would have walked away from the deal frankly maybe not but we we would have tried harder we did get 7,000 in concessions or something crazy he needed a new roof like it could have been much more the seller was actually very stubborn he walked for He was like one of those guys that would let it sit mhm that's wild he was an old you know old beater home but like oh Gooman House new groups coming in all these develments i'm I need this price or I'm not going to sell it right kick rocks and and the more important part there was like when I started to dig back the layers of this house cuz very quickly after you become an agent you're like should I go out of you like got your first commission check and you're like I'm going to put it in the house and I was like why i already had by the way I had already spent the money yeah i was kind of asking for forgiveness after going so what do I do what do I do with this like how do I build value here and you're like I'm need to replace the furnace should I go this direction should I do this and actually he kept saying heat pump to me i'm like what are you talking about a heat there's no way there's a heat pump in this tiny little house it is a there has to be an HVAC and a furnace and a condenser and he's like pointing at the thing outside which was a condenser and he knows that now but at the time I was like trying to help coach through how to make this house what it was and what we just sold which is a property that was turnkey ready that could rent out for uh 1,900 a month is that what we ended up renting it out for no well when like just recently yeah no it was like 2,000 like 2,000 a month crazy and it's a house that you bought in 2023 for how much 115 120 120 put some value ad along the way call it 30 35,000 along the way to fix it up for an asset that could rent for 2,000 bucks you sold for 175 yes crazy yeah i I And I know you're about to say something i think the biggest regret you'll have is selling it oh he knows 10 years and you know that and we've talked we've we've talked about that thousands of times yeah but but listen here's here's why I don't regret buying that house it's for two reasons uh number one that house became a great store of value uh because what I noticed as a young individual even now um is like the second money hits your account uh your mind starts thinking about ways to spend it whether or not it's through good ways like investing or saving and and or giving or whatever or spending it on things that just don't matter things like that which are very fun uh your mind immediately goes to where do I need to move this money maybe is a better way to say it um and so what that house did was number one it forced me to make renovations because I was living in it so spending the money on the bathroom the kitchen the roof the HVAC it was like I I needed to do that stuff keep going yeah um so anyways it became a very good store of value because what I knew is that every penny I put into that house because of the area I bought it in uh and the kind of renovations that I was doing my money was going to sit there and it was going to appreciate and I wasn't going to lose it and as a young individual that is extremely powerful um so that was the first thing that it did for me um the second thing was is that it taught me the road map i did the thing right like I I'm going back to what I said when we started this podcast i was able to learn and do it in a way that wasn't going to completely uh annihilate uh the the rest of my life right like I didn't I didn't lose my uh I didn't lose my pants on the deal which is great uh and it allowed me to get my hands on the project and do it myself all three of us did everything the same which is we bought a house with no reserves no no plan we just bought the house and then we figured it out i have a client right now he's going through the same thing bought the duplex it's a 100-y old duplex we had plenty of conversations to coach him up on that he's not calling me saying "Why'd you let me buy this house?" He's calling me saying "I'm not sure what to do here because I normally would just call the 1800 line and the landlord would be there to fix it i have a sewer issue what do I do m and cuz I I kept catching myself going "Well you have a sewer issue because we got the the electoral or we got this fixed during the cuz I was feeling bad some type of way." I'm like "We got the stuff fixed and we negotiated." He's like "I know that i don't know where to go and if I should be adding money." And he's like "I didn't really have that piggy bank built to go in." Neither did any of us we all just went buck wild when I moved in and laid my head on my pillow for the first time in my first home I had like 500 bucks left after it 500 bucks i over 30 grand walking in but I spent it all on renovating it the mortgage was 900 and it was due in two weeks right what happens you go figure it out and you make it happen and by figuring out and making it happen I walked away with a six figure gain on that home in three years yeah that's the power and the wealth just getting started and running through the brick wall right and I think there's two if I can underscore this for the audience there's two big You buy the house you have no money there's two big things you gain in a nonmonetary way one of which is an ownership mentality you just said it when you replace the the furnace you're like "That's a large chunk of money." But this is your infrastructure your asset all this is hopefully increasing the store store value i love that phrase and the second is long-term wealth anyone who's getting in this has stopped the one month six month one-year cycle like I have a I have a cousin he's not going to listen to this don't worry he can't get off seeing finances in one month integ so he it makes sense his rent payment at 1,800 because he can still like have some margin save yeah he's like I make 3,600 and the car is four and that rent is going to go from 1,800 to 2,000 to 2500 and you're not going to you're treadmill forever yep i was like I have all these investments and that payment is a lot i have I don't know $10,000 of mortgages a month I have to pay it kind of sucks actually month doesn't look pretty but I look in 30 years where where that's going to be versus you renting it's the store of wealth and value over time right it's complete upside down right flip it on its head on it and a percentage of that i love to calculate how much is actually going to the principal okay it's less than I always want it to be way less but it's still like let's just say out of the 10,000 a,000 of it it's about one/10enth that actually now some of these are early mortgages and they'll they'll become 9/10en towards principal that it's like 99 bucks a month going to the principal yeah i have it's hundred dollars a month it kind but it's still that will be significant over a long enough time horizon and at such a scale right right and we've talked about this with Jeremy let's just say you sell one of your investment properties you put 100K down and recast it into a 20-year or a 15-year mortgage now you're paying a lot more in principle yep so there's ways to you say this a lot there's ways to stack equity and real equity it gets complicated even for me to theorize and see it all it's it's hazy it's like I'm just taking it one one day at a time right now with investing myself but it's where I'm going to is you inherit one an ownership mentality uh which is huge i'm not calling the boss the tenant or the the landlord anymore and it's empowering by the way is another very important yeah and then the long-term mindset of I'm going to have assets that work for me when I'm sleeping mentality the great news about it though is that we're all better landlords of our properties because we were the landlord in our properties if that makes sense right the first property we lived in we took care of we were the ones calling the 1-800 number and guess who was answering your phone was buzzing yeah yeah my my phone was buzzing i was calling calling and and I had to go replace the thing and get creative and actually get preventative and start replacing things that had foresight that I could see coming ahead guess what I do on all my properties now i hire off lease construction to do PMR reports every by annually they come in clean out the gutters change the furnace filters take the pictures of how the tenants are treating the place and I get to make a decision as a property owner how I want to be preventative in my maintenance and they'll give suggestions mhm best $400 you can ever spend on a on your asset is that right there the quarterly PMR um I I I would not know that if I didn't live in the first one right and didn't have the freaking roof start leaking and uh everything in between i want to switch gears and start stack stacking on uh the true equity in relationships you hinted at it a little bit earlier um I think it's valuable something that's driven your life and and kind of helped you get to where you are at a young age which like Tyler at the beginning said 40 deals closed in the past year and a half 40 transactions there are agents who won't even eclipse that they'll leave the business before they get to that they average agent has done two deals this year yeah i mean to be in the top uh 5% you had to sell eight homes last year so just for reference for everybody listening everyone on our team is I want% right I want to think of how that scale unlocks through the relational equity that you've been able to build um what is for somebody listening who is Trent a few years ago what's the number one habit that they can implement in their life to start stacking towards um just to get better I don't even know if two years ago you knew where you that you'd be like where you're at today i don't even know if you want to be a realator to be honest i still question that every week i'm like did this guy want to be an agent i think he want to be in real estate i don't know if he want to be an agent so what's what's the number one habit was that the question i think yeah yeah yeah i could take that in so many different directions um here here's the thing um I as a young individual growing up I remember being in middle school and high school um being a procrastinator through and through you couldn't get me to do anything regarding school i mean I mean literally I remember uh I remember showing up before school the only reason I would get to school early is because I wanted to have enough time to go to the library to copy the homework from someone else in my class before we had to get to first period that's why I showed up early to school um and what I learned through adulting and learning and becoming the human being that I am today is that that wasn't because I'm a lazy person yeah how's the negotiation look like to get that person to the library right no yeah uh but it wasn't because I was a lazy person it's because I had absolutely no um desire or um I don't know what the word I'm looking for i had no interest in anything that I was doing at that time um and so the biggest lesson for me was is that it was less about like changing something in my mind or changing a specific system or process in my life it was about finding something that I was truly passionate about because when I unlocked that it became easier to want to go do it every day and wake up early to go do it every day and so once you have found the thing that you genuinely say to yourself like I love doing this and I want to go get as good at it as I possibly can it becomes that much easier to implement the systems and the processes so then you find out how to use a calendar then you start time blocking and having a mission really is what I'm hearing yeah which is still something I'm crafting every day right like I I plan on doing that for the rest of my life you usually don't know how to verbalize it you experience it and then verbalize it later right you arrive at it right you or I had it every time that something changes for me it's because I went through something hard and then went to the people in my life alex Wento was on here he talked about five uh the five boards his episodes down below but uh people having people being a board of adviserss going to them you have a major thing happening in your life you call up one 2 3 four and five and you see how they react to it and you get their judgments and their tidbits and then you can grow from there i just came from a coaching session from a strategic coach that I pay in my life to help me discover there and guess what i feel like I just unlocked a new level coming out of a really hard two months mhm and it takes like what you're saying the vulnerability to be curious i think it's like a way to frame it up and to know the why and to not forget your mission yeah and and the interesting thing is is the habits become a side effect right i am interested in what I am doing and so because of that I find it it's normal for me to be involved sending deals to clients because I want to see them win and I'm super excited about doing that so the act of sending deals and making time to interact with clients becomes a habit but that's a side effect uh of me genuinely enjoying and being excited about what I'm doing uh and that that doesn't I'm not saying you don't need you shouldn't be intentional about uh you know the system and the way in which you do things obviously you should um but those things start to come naturally is what I'm trying to say and what I love is the full circle here this really just connects to you were you were crafted and birthed in um I'm struggling with words here you Yeah a creator created you for a purpose and when you find that purpose that you're meant to do and have the impact with other people it becomes easier to click the habits in place but when you're just like homework for a grade and right a class that doesn't matter you why would you try right but when it's your god-given purpose to get other elevate others it clicks into place it's the same thing for even this podcast why would I show up and be fired up about this it's because I actually think there's one person that's going to go on Bigger Pockets tonight and start researching things and make a call to one of us because of this podcast right and will and it'll cause that ripple effect you you hit the nail on the head though like you go back to high school and who are the people that were actually engaging it's people that want to be doctors it's people that wanted to go somewhere that they had to get a higher education to do the trade and skill that they want to do right i knew I wasn't going to be a surgeon so why do I give a [ __ ] right i knew I wanted to do something in business and and what am I going to do i'm going to start selling crap like while I'm at school and make relationships and play that game uh I think we would do a disservice if we didn't talk about you said something so insightful in the beginning i had to identify the tenant while I was under contract for my first house to make it you and I have found and unlocked the ability to find tenants while under contract to make a cash on cash return for investors that uh quite frankly is pretty difficult to find indianapolis like number two right now for the most desirable market or whatever the stat is on Zillow um or Red Fend whoever gave it but we are at a cool place where I'm now getting I had somebody combative yesterday on an intro call talked to the guy I'm like hey uh what are you looking for cash return I about said appreciation he said I don't care about appreciation and I said well you can't ignore appreciation he goes I know but I own property and I know that they're going to appreciate in value and I know where Indy's headed that's why I'm calling I want to know if I can hit a return a rate of return i go that's a much more mature way to frame it up and I go in fact maybe um highlight on the like what we see every day and some of the duplexes that we've sold recently um and that that light of the tenant first in a sense yeah so what I think you and I both uh have found is that being able to not only provide a client with an asset that is what we would consider to be turnkey ready to go first day you buy it um it's even cooler when you can provide someone with a turnkey house that also has great paying tenants in it day one because they completely are able to negate any sort of bakedin vacancy into their spreadsheet year one um and a property manager is able to get in there and do what they do best and manage tenants effectively and that takes a lot of the pressure off of a newer investor and so Max and I I think have found a lot of value in doing that for our clients uh to to sort of talk a little bit more about the first point you made um I I think a lot of people are naturally very uh they get very uh focused on that cash on cash year one number right what everyone's concerned about because it's hard to see the ethereal growth the equity stack like Tyler said he even has like I start going on and on and it just becomes a lot comforting factor I think too seeing a 7% cash on cash it gives you comfort like it's going to have grease on the wheels the reality is even if a I want to know how many people actually go and recalculate once they own it they're not they're thinking about monthly cash flow burn they're thinking about their liquidity on hand they're thinking about other things they're not even calculating it well they go to the five profit centers at that rate yeah correct right and then it's like what can I get out of this if I refinance or sell it like those are the things that matter how do I unlock it it's funny how little correlation or reflecting back on that original cash on cash there is you know as an aside but yeah which is okay i used to that used to kind of frustrate me a little bit but I have a better frame of reference now to understand why that's what people's minds go to as the first sort of uh benchmark if you will anyways I say all of that to say uh there there's only really one solution there that I I shouldn't say one solution there's a couple of solutions there's one that I really like and others that I don't like um so you have to find a way to inflate rents and I think you do that through a couple of different ways number one you can utilize a different strategy so you can go buy an Airbnb and do a short-term rental you can go you know do a midterm rental and get traveling nurses and you can bump up rates that way what I tell clients all the time is is that unless you consider yourself to be an expert in that field for the love of God don't do it it's hospitality it's hospitality you are no longer operating a rental you are now operating every house is its own business investment not passive if you don't want to be the bellhop the front desk person the freaking remote control battery expert on what goes where don't do it the password provider the one caveat I will and I know you haven't finished your full thing is if the property is cash flowing at a certain clip and you can afford to have someone operating it who is the bellhop um you know operator touch hands-on person then that could still work but you you're probably buying a more expensive asset such as my $ 1. 5 million lake house that where it makes sense yeah um anyways and it has other things in it to provide the value because I know what you're saying there is a special client a special property and a special manager yeah but they're special and they want to go in that direction i've got one right now he crushes he does 100K topline a year on a property that he bought for 350,000 in Bates Hendricks but guess what the manager is an the literal expert in that space in Indie and it was a rare buy yeah yeah so once again I want I want to make this point you cannot fake it in our industry no it's the same thing in like this our that space in my opinion uh at least in our market is starting to get a little bit saturated because people saw the returns on paper that they thought they could make and so they went and purchased properties uh that maybe they shouldn't have in areas that maybe don't actually do as well as they would anticipate or they didn't hire the right manager or they bought the wrong furniture and they didn't actually use a theme and make it look cute so people don't want to actually like stay there whatever the case maybe we could talk about it all day long you cannot fake it and so if you are an expert in that field cool go do it you'll crush like you have a competitive advantage go do it right um I know it's something that you're kind of passionate about you like helping clients do that um but anyways I still have that to say um I don't think that that is the right solution for a lot of people what I have been helping people do a lot uh is subsidize housing um and whether that is through uh some of the big nonforprofits that operate in our city or through section 8 um we help uh you know people place those tenants um sometimes our sellers if they are savvy enough will do that um for those people and offer that as sort of like a piece of the purchase agreement to make it a little bit more enticing for someone maybe to pay them the number that they want um but that's the way that you inflate rents so for example um I can count you know on you know one hand I've probably done you know three four five section 8 deals just this year uh where literally buyers will end up with a 15 to 20% cash on cash day one out like off the rip uh which is insane like you can't get that through any other vehicle uh to my knowledge in terms of like a longer term hold other than doing something like Like we are closing on these at a clip of like every other week on these types of properties where they're turning and sometimes you buff up rents too by just providing a higher level of finish than the guy next door and I see plus neighborhood uh so like you go compete you you look at my portfolio that's what I do i I crush everybody i know I have the highest rents in the neighborhood but guess what i have the best product and I'm the best manager in the neighborhood mh and so I get the cash on cash return and so it's like that vehicle right you go to subsidize or you go to provide an excellent service mhm the other thing that I found though is through you're about to you may maybe were about to say this we've handed people 15% cash on cash properties now it depends on how they use the weapon because if you don't pick it up and fire it correctly it's going to backfire yep there's a big caution label on it right it's like hey this is juicy but it's hot right like it might bite yeah and what I mean by that is hire the professional manager to get in there before you close and get it off the ground right because these tenants cannot go without somebody facing right if they have somebody going along the journey with them it's excellent the ones that I'm thinking in my head that have they're killing it absolutely murdering the deals and the ones that haven't I'm like I question should we have sold that to them like was it were the tenants bad were this bad why did it work over here but it didn't work over here um and that's the one thing that Roots doesn't provide but what we do provide is people and professionals who can do it that are great in that arena um and it's something that you and I are pretty passionate about that we've been able to like we're still working on it still solving it but I know we have like probably 10 deals in inventory right now that all would be maybe not quite 20% but definitely over 12 and I'm using that as an example it's just kind of like on the high end but yeah and people who want these deals need to go to rootsreal. co So get on our deal bus because like I I know people are sitting on Zillow spinning their wheels right thinking is this a good deal or not get on our deal sheet you do a write up i just sent it out to 2,000 people this morning you can sign up to the newsletter in the link below it's a top link before you even subscribe i I want you to be on the newsletter before you subscribe to this YouTube channel the newsletter is the most powerful thing that we do tyler writes up beautiful things about Indianapolis you need to know if you're going to own here and if you already own here and you don't these deals that we're talking about that have the juicy cash and cash that they're waiting there and then someone's going to be like why can't I get that people ask more when we show when I I do sometimes on the newsletter I show the success stories hey this person bought this and they did that i was like can I get that why can't I get that like they respond to it and they click on the Zillow link me showing what just sold i'm like that went out two newsletters ago two newsletters ago had your head stuck too far up your butt and guess what it also was live on the market with all the same inscilary things right but here's the thing we we talk about those these kinds of deals like they're commonplace we provide a great service to our clients in hosting a lot of those deals off market and what people don't understand is like yeah you can go you know go on the MLS and you can find yourself a duplex that you can throw some section 8 tenants in absolutely we can do that but we're talking about providing a turnkey house with tenants in them already that are paying day one that is not you don't just go on Zillow and have you know 15 20 of those deals you can just pick from you do but there are people exiting the marketplace for a bunch of reasons right so people the one the one-off owners that still have a tenant that didn't hire the manager that are struggling yeah from history and it's a 16 $160,000 single family that's rented for 900 right like it that's what I'm saying that's precisely what I'm saying yeah to end up in the situation that we've talked about you can't just 30 3916 I think it is market Street 39 something Market Street is on the market right now it's a quad uh essentially rents for 4,000 bucks a month we have it listed at 350 mhm like come on it's crazy yeah billion people are going to scroll over that um let's wrap up with our rapid fire questions let's do it friday night I know you don't have a significant other yet with the boys what's a good place to grab the most delicious bite in Indie uh I really like Livery livery is a great spot um the empanadas are great the cocktail i was about to ask what's your favorite thing on the menu you would say empanadas the empanadas are great yeah they have a they have a red drum which they are super popular like their red drum fish dish whatever that's super popular too yeah I would say it is the best tm best margaritas in Indie does go to livery uh canado It's trash it's pre-made yeah livery is a totally different level yeah so you got to go hit up livery livery you got to ask for the Trent special they'll look at you funny because they have no idea who Trent is yeah uh what's the number one habit that changed your life uh being in God's word yeah uh in what way how has that expanded in the past like six months yeah it's uh it's given me uh a a better frame of reference uh of looking at what I do and having a purpose behind what I do um I think our lane can get very transactional and when you're able to back up and uh actually dive into your purpose like you were referring to earlier and you're able to use God's word to actually see that a little bit better uh it's very enlightening i heard something recently that was like be in scripture not out of fear of being around a table with people that know scripture better than you do uh kind of like this saying right you you start take it to a gym you walk into the gym you've not hit the gym in years so you don't even know how much the bar weighs anymore because you've been there for so long he's 45 by the way if you're curious and like you're going to lift but the ne the guy next to you is just freaking he's he's jacked right he just hit this he just was doing push-ups in the sauna that's how jacked he is and now he's lifting like seven of the plates and three bars at once because he knows it because he's been doing it and has the habit of it um it like super motivated me to to dive back in to God's word because that becomes a challenge right you like sit around a table and people go poundfor-pound they start throwing out these John 7534 and I'm like can't keep up like I get it the spiritual journey but like the scripture is huge so that's something that you Kyle Ian Tyler everybody on the team I've watched grow in it like all right I got to dust the boy off and open it up so it's key that unlocks right the vision and I was thinking of this like the vision is vision means there's there's different ways of looking into the world one way is a transactional lens which is I didn't get what I want or I'm just trying to go get mine and get what I want wo is me and it's a it's a lie from the enemy it's a lie from the devil right and I believe in spiritual warfare it's biblical it's and that's the frame of reference of which I base my truth but then there's a different vision of which is the word incarnate which is um uh putting others before yourself right is the way uh if we if we are eternal beings so and I'm not trying to get on a sermon here but it's a different vision in which you approach clients and deals and sellers and buyers if you believe it's a part of an actual uh ministry i don't know a better word to put it so I think that's awesome and I've seen that flourish in you i've seen your joy and uh happiness increase a lot from where you used to be frankly so I see the fruit of that all right Pastor Tyler is done talking next question i got to brush up on that uh no uh what is an area of your life that you're currently working on growing good question several um one for me right now I think is uh my close relationships with my friends and family i think that those have taken a beating over the last couple of years because of uh how involved I've been in work and in business and they those people understand that um but that's not an excuse to allow those things to suffer uh and so I think uh creating meaningful uh time and spaces uh to build relationships with those people uh is something I'm definitely trying to work on uh the other one that everyone has heard a million times is being more active and and uh and getting out there and working out and maybe running a marathon with Tyler or something um seeds are planted yeah so last time we talked you said I will never do that now you're talking about it right um just for the podcast so people think that u but but that's you can start being Ian's dog and chase the frisbee yeah right yeah i love that it sounds like in one word I'm going to just name it for you which is like having priorities and putting guard rails to protect those priorities because in a early real estate entrepreneur's career work it expands and takes over all the empty areas of your life until there's no areas left it's all real estate and that is not a good area that is not a good place to be in for a healthy mind body spirit you have to put guard rails on that and protect these other priorities right it's like Max and I have talked about every single podcast when we get home we put our phone in another room and are present for dinner time and the hour after dinner time and that h that's a habit it doesn't come natural like we could easily be on our phone the whole time and worrying about deals easily it's the 9010 right when your life is truly at balance which takes a lot of work um and I think putting the right people in place ironically bringing more relationships in to help find that balance is going to be huge in the in the life cycle um dude thanks for coming on i know that this is this is in general probably not your comfort zone having throat it's good yeah it's good for me to get out of my comfort zone we will be certainly having a round too with Trent and getting some of the other agents on our team every agent team has an amazing story yeah and has unique insights to share and people just need to work with roots agents yeah I think roots agent totally if you if you have not checked out the new rootsity. co website you are missing out the thing is beautiful tyler did an amazing job uh shout out Jared and all his hard work on that so go check out rootsre. com properties offmarket properties coming soon coming soon properties all over properties we're selling yep and you got to get plugged in to the newsletter and if you could do one thing for us we don't ask anything else besides this one thing please for the love of God share this to somebody who is like Trent in your life that you want to go and chase and and buy a house with right the only way you're going to do it is if you bet with the next guy next to you so if you're Peter go call John and say "John we're going to buy a house by the end of this year listen to this podcast let's get fired up and go after and do it."
Episode questions, answered
Quick answers from this guide.
How did Trent Kiester buy his first investment property with only $10,000?
Trent saved $10,000 working as a barback and server at Back Nine Golf Course. He used an FHA loan with his father as a co-signer to purchase a single-family home around $125,000 in the Riverside neighborhood of Indianapolis. To cover the mortgage, he rented a bedroom to a coworker named Evan before closing.
What is house hacking and why do Tyler and Max recommend it?
House hacking means buying a primary residence and renting out extra bedrooms or units to offset the mortgage payment. Tyler and Max call it the most powerful vehicle in real estate investing because it allows buyers with limited savings to enter the market using owner-occupant loan programs like FHA. It builds equity while reducing or eliminating your housing cost.
What FHA co-signer rule affected Trent's ability to buy a duplex?
Trent originally planned to buy a duplex with an FHA loan, living in one unit and renting the other. He learned that when a co-signer is on an FHA loan for a multi-unit property, the co-signer must also live in the property. Because his father would not be living there, Trent had to purchase a single-family home instead.
How did Trent find real estate mentors before becoming an agent?
Trent deliberately took a job at Back Nine Golf Course because he believed wealthy real estate investors would frequent the bar there. He overheard two men discussing a flip in Fountain Square, inserted himself into the conversation, and built relationships with mentors he still has today. He credits being in rooms with people who were further along as a key turning point in his journey.
Why did Trent choose to become a real estate agent instead of a wholesaler?
Trent tried wholesaling before getting his license but found it did not suit how he builds relationships. He values creating long-term connections with clients, which he feels the agent role supports better than the more transactional nature of wholesaling. After Max suggested he get his license during a conversation about a distressed property deal, Trent enrolled in classes within a month.
How quickly did Trent Kiester reach the top of new agent production?
Trent joined Roots Realty Co in early 2024 and within roughly one year completed over 40 transactions totaling more than $7.5 million in volume. Tyler and Max estimate that places him in the top 1 to 2 percent of new real estate agents. He focuses primarily on investor clients.
What is the three-step framework Tyler outlines for reaching $1 million net worth before 30?
Tyler's three steps are: first, build a networking tree by doing 50 coffee meetings and asking each person who else you should meet; second, house hack your primary residence two or three times before major life commitments; and third, learn to leverage other people's money. He says this is the path he followed himself and that Trent's story mirrors it closely.
What mindset shift did Trent say was most important before buying his first property?
Trent said the first hurdle was moving from wanting or fantasizing about buying a property to deciding he was going to do it no matter what. He also emphasized that consuming information through forums, YouTube, and mentors is not enough on its own. You have to take action and do the thing to actually learn how real estate investing works.