The Roots Podcast

He Fasted 297 Days to Close One Real Estate Deal | Aaron Laster’s Story

Aaron LasterApril 22, 2025

Aaron Laster shares how he wholesaled 11 deals in college, used seller financing, and is building 1,000 doors with a focus on affordable housing in Indianapolis.

Episode summary

In this episode of the Roots Podcast, Max Moore and Tyler Lingle sit down with real estate investor and affordable housing advocate Aaron Laster. From vending machines in his dad’s barber shop to seller-financed deals and tax sale bidding wars, Aaron’s journey is packed with hustle, creativity, and long-term vision. He opens up about wholesaling 11 deals in college, transitioning into affordable housing development, and his mission to create 1,000 doors, with at least half focused on community impact. Connect w/ Aaron:  

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Mentioned in this episode
Merchants Affordable HousingRenew IndianapolisBHB RealtyIndiana Housing ConferenceVolunteers of AmericaDamian Center

Chapters

  1. 00:00From Barber Shop to Business Hustler
  2. 03:50Breaking In: Tax Sales, Seller Financing & Wholesaling
  3. 12:15Pivoting to Purpose: Mentorship & Affordable Housing
  4. 18:30Losing Money, Finding Clarity
  5. 25:40Holding over Flipping: How He Built Long-Term Wealth
  6. 33:10Why He’s Betting Big on Indy’s Near West Side
  7. 41:57Rest, Fasting & Building a Life That Lasts

Full transcript

Auto-generated from the episode audio. May contain minor errors.

house hack or the the wholesale. What do you recommend there? You did both, right? Wholesaling. A lot of people do make it look easy on social media. Like they just say it's so easy. I didn't come from a wealthy family and I didn't have the credit to go out and get a mortgage on my own, so I needed to build up cash. Last year, I fasted for 297 days until I uh executed the contract for the 13. Welcome back to the Roots podcast. Today we have on Aaron Ler. Aaron Ler is a new friend for Max and I. Um I met him for coffee about three or four months ago and his story just blew me away. So Aaron Ler is primarily a real estate investor. He owns a small to mediumsiz portfolio of now some apartment buildings, single family homes, um some industrial real estate. Um but he has a crazy background. Um just a hustler from day one. Had vending machines, helping with a barber shop. So, I'm really excited to get into it. Thanks for coming on, Aaron. Absolutely. Appreciate you guys having me. Absolutely. Yeah. So, I want to go back to before real estate with uh where we began with in your family. It looks like you were kind of a hustler. I'm not sure if you had siblings doing that, but it says in your background that I was kind of going over, you started with vending machines. Um, how did that come about? Like, how old were you and where did that desire to get that going come from? For sure. So, elementary age, um, I can't really say it was my idea. It was my dad's idea for the most part. Um, just having his sons doing something and being busy. Um, so yeah, that was just my introduction to business. Both my parents are entrepreneurs. Um, that experience alone let me know early on that, you know, I wanted to choose my own path and, uh, yeah, so it wasn't my idea. I can't I can't take credit for that. So, what was the flow? Where where were the vending machines located? How many? I'm I'm curious. This is awesome. Yeah. Yeah. So, it was just two two vending machines, a pop machine and a snack machine. Um, both in my dad's barber shop. Oh, sweet. Yep. So, Tyler and I, this small plug for a high school household, volunteer for a program that's helping kids in high school, you know, get into like see that entrepreneurship can happen and that, you know, college doesn't have to be the path. You can start with a couple of vending machines and build rental portfolio from income. Um or like we got kids pressure washing, cleaning windows, whatever. That's super cool. I think that hits on, you know, having a role model young 100%. What was the through line from starting doing that with your dad's barber shop to real estate like connect the dots for me on on that transition. That could be a long story. So give me the brief version there. That goes from elementary all the way to college. So um so elementary of course started with the vending machines with my brothers. [Music] um continued to do that through middle school. Kind of fell off from that in high school as I was getting more involved in athletics. Um in high school, I actually started working very early also. So, I started working at McDonald's at 14. Unfortunately, I spent most of that money on sneakers, uh like like most 14 year olds probably are. Um but so yeah, did that unfortunately spent too much money on things that I didn't need. um went to IU for college. Um met one of my fraternity brothers who was not my fraternity brother at the time. He was using his refund checks to go to city auctions and buy properties. And I tried to replicate his model as much as I could. But of course, I kind of got boxed out of that because out of state investors from New York, California, Chicago, they kept coming to these auctions and outbidding me. So, um, I I didn't have enough liquidity to be able to continue to do that long term. So, I did a couple properties, uh, bought a couple properties from the tax sale and then I moved more into seller financing deals. So, the house I actually live in now is the very first rental property that I bought. Um, and I bought that from a church across the street. Just made a down payment, acted as if they were the mortgage company, and paid them monthly. Um, thankfully I had 0% interest on that. And, uh, yeah, from there I I had a little bit of trouble continuing to buy rentals, so I kind of shifted to wholesaling real estate. Um, I did 11 wholesale deals while I was in college. My very first wholesale deal was actually to Mark Mark Noddingham. Uh, so about connection. Yeah, absolutely. The owner of our our brokerage. Yep. Yep. Wow. Mark on the pod. Yeah, you should do that for sure. So, he was my very first wholesale deal and it opened my eyes to And how did you get connected with Mark? I'm I'm sorry. No, no, you're just curious how that happened. So, it was just cold calling. Um, I did a lot of cold calling. Um, sending out mailers. So, I would just use the city GIS, the geographic information system to find out who owns the property and then skip trace their number. Yep. Very cool. So, I did that. So, what year was the tax sale? What years? Um, so I went from 2016 to 2019 I believe and then 2020 COVID happened and then after that they really moved online. So all the auctions are online now. I haven't really been attending those. It was even like 16 was one of the Jeremy Tolman. We had him on the podcast just released his episode. He that's how he built his whole portfolio is tax sales. And he says like 16 is where he's really 2012 2013 is where he started getting beat constantly at tax sales cuz the large funds like you're talking about. Yep. And he got demotivated from it really in 16. He's like, "Oh, I can just go find something on the market at this point because everybody's bidding up the prices." Um, so what was the the first deal becomes a wholesale deal with Mark? Um what how did that parlay into the other 11 to the other 11 doors that I have now? Um so dang. So that was quite a bit of time since it's been quite a bit of time since then. So I think my next deal was actually a duplex um seller financing. I think that was next. But around that same time is where I met Mike Petri at um an awards ceremony and he actually like we connected really uh organically I'll say so we just had a conversation about IU quite a bit. He went to IU um and he just I don't know he he essentially became a mentor of mine. So we grab grabbed breakfast several times. he introduced me to his CEO of his nonprofit, Merchants Affordable Housing, Janine Betsy. Um, and that got me into um the affordable housing space. So, I started dealing with more LITC deals, low-inccome housing tax credits and home funds, other funings mechanisms for um affordable housing. So, I kind of pivoted from, you know, just buying vacant lots, single family homes, duplexes into more of trying to get my first tax credit deal done or my first, um, apartment acquisition done. So, um, did that, ended up getting hired as a fellow at Merchants Affordable Housing. So, I did that for about a year and nine months, learned quite a bit from them about the space. And after my fellowship with them, I actually kind of pivoted. I did uh three flips with some fraternity brothers and got burned on those by our contractor. Each of us each of us lost quite a bit of money and I was probably 24 25 at the time. So took a major hit. Um kind of felt myself getting burnt out on real estate but didn't want to I knew this is what I wanted to do long term. So kind of took a step back and went back down to Bloomington, did a internship at a venture capital firm where I was in investing in startups and um alongside that I tried to build my own prop tech platform which was essentially a platform for real estate syndication. Um but you know that didn't go as planned. Struggle to to raise capital for that. I found that it was easier to raise capital for actual properties than a tech startup. Uh so a little more tried and true. Absolutely. It's absolutely it's more stable for sure. Um so after that internship in Bloomington um the then CEO of Merchants Affordable Housing reached out to me because they took over a nonprofit that had went under. Um they took over the board and they had a six-unit apartment building in my neighborhood that they were looking to sell. it just didn't make sense for them to hold on to it. The ne the next largest property that they had was I believe 30 30 units. So, bought that 30 units and yeah, that got me up to the 11. Interesting. How is the uh how did wholesaling play into that? Yeah, so that was while I was in college. Thankfully, I mean, I was young, willing to pivot. Uh I was able to be nimble and move into I would just call myself a real estate entrepreneur, honestly. like that done a lot in a short amount of time. My question to you is when someone's trying to start, a lot of people want to start wholesaling because it requires no money down, right? That's why I was hitting on it so much. I'm like, so do you recommend that? Let me finish the question. Let me do you recommend that or like the owner, you did a rental, too, which was the owner uh financing. Yep. You know, it's kind of like the house hack or the the wholesale. What do you recommend there? you did both, right? What do you think is the best place to start? That's a great qu. I think it really depends on the person, like uh what you're willing to do. Um wholesaling, a lot of people do make it look easy on social media. Like they just say it's so easy. Just no cash. Of course, they're going to try to entice people to to get into that space, but it requires a lot of cold calling, a lot of mailing. You got to reach out to a lot of people. You got to get a lot of nos. A lot of people can't take so many nos. So, um, but for me, it was just, um, a way to build up capital. Like, I didn't I didn't come from a a wealthy family and I didn't have the credit to go out and get a mortgage on my own, so I needed to build up cash. And at the time, it was it was quite a few wholesalers. Um, I would say it was less popular than it is now. Um, but, um, to answer your question, personally, I prefer rentals. I prefer to buy. And a lot of people say you make your money when you buy, not when you sell. I think you make your money the most from buying. I mean, from waiting more than you do from buying or selling. So, you know, just holding on to those assets long term is where you make the most money. But I think it's really it really just comes down to, you know, that person individually what they're willing to do. Well, you make your you fix your mistakes when you hold. Yeah. Yeah. The the most time held. We were talking with Tyler before we jumped on about his purchases this year and he's like, I need to turn these two two single families that are having turnover and vacancy and I'm I'm getting hit with expenses each year. You're like, I need to get rid of them. But we've unpacked multiple times those two single families have been absolute killers for you because of the time that you've held it. Oh, yeah. And we were we were talking I didn't understand until very recently the power of leverage. Mh. Because you can buy a property for 40k and that will appreciate in about 3 to 5 years. 40k, 2. 5% a year, whatever it is in Indianapolis, you're going to double your money. I mean, leverage makes it so easy to double that capital and build from there. It's the liquidity events that really, I guess, make it go hockey stick, either refi or selling. So, it's tricky to know how long do you hold. And I've seen more and more people that I'm friends with say holding for life maybe isn't always it. Because when you're young and you sell and you have capital to to reuse, not to pocket and go buy a Lamborghini, that can be a huge event, too. Mhm. How have you Have you sold anything? I'm just curious. Oh, yeah. So, sold some wholesale. Well, the whole uh duplexes. So, I only have one single family home now. Um and the same one that owner financing. Yeah, same one that I bought owner financing. Yeah. And you 2016? You paid that off. Yeah. Yeah. Yeah. Talk to me about how you structured that owner financing deal. I'm really curious. Yeah. So, my dad, he's a pastor locally um on the I guess that's the near east side. Um so, he has a very close relationship with a lot of pastors and churches. Um and there was a church that was looking to to sell a house. They just didn't want to deal with the headaches of being a landlord. So, um I presented an offer that I guess they just couldn't refuse at the time. Um, and yeah, it just worked out perfectly. And you knew about seller financing at this time. Apparently, you had studied it up a little bit. Yeah, from primarily from like Bigger Pockets. So, in college, I was doing a lot of research on Bigger Pockets. Um, and my mentor that is my fraternity brother now, but wasn't then. He had did a couple of seller financing deals, but yeah, that's where I learned about it from. I love that. And I think that the best deals are usually when someone has a need they have to sell and they're not on the market. So you can have those discussions with them about like, hey, are you open to getting some of that equity later, maybe with interest? In your case, it was without interest. Um, which is crazy to me. Um, but the the purchase price probably was like a huge win for them. Or maybe not. Uh, I mean, look at How much was it? Yeah, it was only $15,000. So different different time era but a different time looking and it was uh it was rent ready at the time. So I was able to move renters in um I had a property management company BHB realy um they're Larry. Yeah. You love you know Larry. Yeah absolutely. So uh he's in the neighborhood and was able to lease it probably like a month after executing the contract on that. Um, wow. So, I didn't have to I still had to come out of pocket monthly to pay the church, but uh a good portion of it came from the actual renters being in the property. That's wild. How So, how long was the owner financing note? Uh, 10 months. Oh, yep. So, yeah, I put $5,000 down and paid them $1,000 per month for 10 months, right? It's like that's like a a 0% interest car loan almost for 15 grand. I mean, that's that's really cool. And you were were you still in IU at that time? Yeah, I was still in IU. So that yeah, that's that's why I actually brought in Larry because I didn't want to keep coming back and forth every single time. Of course, I came up on the weekends when I needed to, but um having that peace of mind, having um someone that specializes in property management that's actually local there uh was extremely beneficial for me. Yeah, having the PM is is crucial in my opinion. You got to have somebody that's not yourself looking at properties. Yep. So, walk me through. You buy that one, 15 grand. Uh, what's the next purchase from there? Uh, another duplex from that church, two doors down. So, it was a it was actually a blighted duplex that um I ended up selling probably 3 or 4 months after to Intend Indiana. It was Renew Indianapolis at the time. um through their blight elimination program, they demolished the property and while I was working at merchants, I was able to buy that property back from them um through their affordable housing addendum. So, I'm holding on to it to develop some affordable housing. Yeah. Talk to me about the affordable housing. You seem really passionate about that. Yeah. Yeah. So, I think you know doing well and doing good are not mutually exclusive. Like you can do both. A lot of people just always think they got to make money and be a bad person. Um, but for me, I think affordable housing is is a way for me to meaningfully impact as many people as I can. So, by 2033, my plan is to have a thousand doors. Um, and if I continue to stack every year, I'll probably likely surpass that. Um, but yeah, affordable housing, I absolutely love it. It can be a headache because bureaucracy and entrepreneurship do not mix well at all. And then there's so much going on with the with the government and HUD and stuff right now and lo local housing agencies that you know everyone's getting hit. Yeah. I don't think there's a single agency doing well right now. Right. Right. A lot of agencies confused. Yeah. I I have quite a few of my tenants come through some sort of agency. Volunteers of America who I like to work through with HUDVASH. Um, but I have like Damian Center, they're just completely no funding. You had to pay the rest of the lease out. Like we don't know. There's three months left and we'll see, I guess, what happens. It's sad how much is is going down. Um, I want to see where the course correct is, right? I feel like there's got to be something down the line that has a bigger cause, but has to be. Yeah. Yeah. And now, so the LITC is fascinating. Um, tax incremental financing, right? Uh so now that would be like a tiff tiff fund. So uh litec is lowincome housing tax credits. Okay. Yeah. So that is funding through tax dollars to purchase apartments, right? So it's it can get a little complicated. So there are investors that receive the tax benefit from investing in the project. So they'll, so if it's a $10 million development, they'll uh say for instance an an investor, you reach out to a syndicator like Senire and they'll bring in investors for you or Korea and they'll give you like 89 cents on a dollar. So you you'll be able to get, you know, 8. 9 million essentially from the investor and then you got to go get, you know, a permanent loan or more grants from the city to actually fund the project. So, it's not coming directly from, you know, taxpayers dollars, but um the the investors are the ones receiving the tax benefit. My understanding with those is developers, it's kind of a fee game for them, right? Yeah. Because there's not a lot of profit for the developers is my understanding through the Yeah. Not over time lower this or that. It's mostly um the win is providing affordable housing and the tax credit. Is that right? Yeah. Yeah. I mean, kind of goes back to the meaningful impact thing, right? Like being a I think everyone deserves nice clean sanitary housing, you know, and if there were not public public private partnerships, we probably would not have much affordable housing because there were no there would be no dollars to subsidize the development costs and the developer would just charge market rate rents. So, um, but yeah, it can be a fee game. Um, you do make a developer fee, but I mean the risk to that is if there's anything that comes up, the developer fee is the first thing to get hit. Um, so if you're experienced and you've done several deals, it it can really be a great way to generate some some cash with not much of your own. So, who identifies like the zone to where that housing can be built? Is there any I'm I'm a complete idiot when it comes You mean affordable housing? Yeah. I I don't know uh the development lens and how that process works at all. And I feel like probably a lot of people that watch have no idea, too. Yeah. Yeah. I mean, you you you may have to go through the city to get a property reszone. Um you may get some push back from the neighborhood that it's going in. There's a lot of people that are what they call nimi nimi people. Not in my backyard. Uh but uh outside of that, you can if the site if there's a feasible site that you can actually develop on and there's no environmental issues, you can go through the process to get the property resed if it makes sense, the neighborhood is okay with it. Um you could definitely get it's extremely competitive though, so I will say that. So, like you have to submit an application and if your site doesn't score as well as others, then you're not going to get awarded and you could potentially lose the money that you that you use to actually get the application submitted. Interesting. I have I'm listing a property for a client right now that I'm like trying to figure out something for it because it's like not a flip. It's not really that great as a long-term rental, but it comes with a vacant lot next to it. Like, there's got to be somebody that wants their hands on it. It's a nice area, too. I mean, it would be a great area to develop affordable housing, I think. Um, and is the timeline on orchestrating those deals a long time because you're working with the city and the government? Yeah, I imagine a lot of hoops to jump through. What does that look like? Absolutely. Uh, yeah, it could it could be, you know, two, you can submit the application and it could be two years before you up to two years before you break ground. Um there's a lot that goes into it as you mentioned like just working with the government alone can be a headache. Um I think there the city of Indianapolis in itself they have a lot of issues with turnover. Unfortunately they're in my opinion they're not paying the people there enough money to stay and retain those people. So there's a lot of turnover and then you always got to go through dealing with a new person that may not have any idea what's going on for your particular project trying to learn their own job while trying to identify the something you've been working on for six months. Yeah, it's got to be a huge struggle. Yeah, it's something that's been you know I think it's been the same since the LITC program was even brought into existence. So um it's not new to new developers. What's your uh big goal for the affordable housing and development side of things? Yeah, so um I mentioned that I would like to have a thousand doors by 2033. Of that probably half will be affordable housing. So um a combination of uh small and mediumsiz multif family properties. Um I kind of want to stay away from the large ones. I don't want to compete with institutions. I don't have any desire to do that. I'm already doing enough uh competing. Well, not really not really competing, but just going back and forth with the government on on these affordable deals. I don't want to do the same with large deals with, you know, actual sharks that are the institutional investors. But, right. Yeah. 500 doors of affordable housing and then the rest could be a mix of um commercial, light industrial. Um yeah, that's awesome. I I would love to understand how much it combats the housing crisis just within our own city. Um and how much of an impact because that has to be a huge ripple. I can imagine I I read somewhere I'm gonna butcher this stat so I'm not going to say a percentage but just the large majority of single family homes in Indianapolis are rentals owned by out ofstate investors. Um and the curve that that has on the ability to do what you're wanting to do. Um it definitely goes the wrong way and puts a huge negative outlook on like you're saying you have to combat with the government. It's like I'm local. I'm in the city. I care about the city a lot. I'm not just a hedge fund sitting. I live here. Yeah. Right. I live in the neighborhood likely and and I'm trying to build in my own backyard. Um No, that's that's really cool. I'm I want to watch that as it unfolds. Yeah. I'm excited to see that journey take place and I think you're going to do it. Absolutely. Yeah. There's no doubt in my mind. You have a lot of momentum there. Um how much of those will be new development ground up versus just buying existing? That's that's another great question. Um, so personally I I like acquisition rehab a lot more than new construction. So can you go through that process with what acquisition rehab is? So acquisition rehab is just acquiring an existing property. It may need some some minor rehab. Um there are are typically there already are some some residents in the building. So you have some income coming in which is something that I love. also the banks love. Um but yeah, so it may need, you know, minor minor rehab. There may be a couple units that need major rehab, but to me, um it just makes a lot more sense to go about it that route than to go through the whole process of, you know, getting permits, getting things reszoned if necessary, you know, dealing with several contractors to um actually build a groundup development. So, for someone that's like, "Awesome. I want to do what what you're doing." Maybe they're based locally here. They have a heart for affordable housing. Uh they've identified a property, maybe even what's like the first step to converting that to affordable housing? That's a good question. So, I think if if you're talking about low-inccome housing tax credits, um you you may want to find a partner, an experienced partner. um it is a very very tough program to go through. But if you're talking about home funds or CDBG funds that go through the city, um those are also affordable housing dollars that you can use to um but yeah, I would say start with, you know, going to city meetings and reading the documents that are on indie. gov if you want to go the home or CDBG route. Um, and if you want to go the LITC route, which is more difficult, you definitely want to, you know, probably go to the Indiana housing conference and get to know people that are actually doing this and build rapport with somebody that could potentially be a partner for you. Um, but yeah, if you're going either one of those routes, it it'll be a little bit different. Yeah, I think that's what I was asking if the the LIT can be some of those that already have income. It's a established house that you're going to convert or rehab and and revitalize. It's very interesting. I'm like there's so many different ways in real estate to one break in two make an impact and three stay sustainable and every day I'm learning something new that's like oh I've never even thought about going through that process where looking at it. I buy the single family home and and put a tenant in it and take care of the tenant. Um, but I haven't thought about like, oh, what impact can I make to change the community around? Um, what's the what's the neighborhood that has your biggest like spotlight in our city? I'm going to give you guys my secret. No, I'm just kidding. So, I like the Near West neighborhood the most. Um, so I started investing Hallville was the very first neighborhood that I bought into while I was in college and so many people were telling me that I was crazy just for buying over there. It was different than what it is now. There is quite a quite a bit of development going on a little bit further west and then up closer to the river. But um once I started investing in the neighborhood, I started going to the neighborhood meetings and reading the actual plans that were that the city was putting together and Lisk was putting together. So I knew what was coming to the area before um you know my peers did or you know even people that are older than me they they didn't know what was going on. So there has been a like almost there's been a huge cosmic shift over there. Um that I've noticed even just in the last 3 years as far as public buildings go. Uh like the library that's over I'm like that thing is nice. Yeah. Brand new. It's a nice library. Yeah. Absolutely. then there's, you know, $300,000 homes that are across the street from it. So, um, yeah, it's early there, you know, and I think that a lot of the investors we work with and even us overlook it. It's not even on their search. It's not even which is crazy in my opinion. Like, I mean, you're you're very close. I think they're scared of of um, you know, low lower income um, what that looks like because it it's still pretty rough. Um especially in Hallville. Um I've toured some properties there and it was on u I can't remember the name of some of the streets. Um but it was different, you know. And even me, I'm like, "All right, would this be a good investment? Who are we going to place here?" Um so I think you have to be ready to kind of roll up your sleeves a little bit and be pretty active with that investment. Would you agree? Or Yeah, absolutely. I mean, of course, there's pockets within Hallville that are better to invest in. Um, oddly, I've actually done quite a few deals in Hawville. On in Hallville. Nice. Um, I have two right now that are under contract. One's on Belleview, which is on the nicer side, closer to Hawthorne. Yep. West side. Um, but right on Parishing, a midterm rental for traveling nurses, and it performs so well. um two right on there that I've done with clients. Then I have a listing coming up uh on Traymont that's going to be a duplex. So you need to add a property to your portfolio. It's right next to Long Donuts. But but my understanding of the west side is it's actually not uh super bad with crime. The east side's actually much worse. If you look at like the crime heat maps, the east side and the far east side is um still a lot of gang violence over there still. Um the west side's a lot of just like families trying to make it for sure. You know, I would agree. A lot of Yeah, I mean we do we do have some violence. Um a lot of gangs tagging properties and stuff like that like just spray painting on properties. Um kind of I guess what they would say marking their ter territory that that they don't even own. Um but yeah, it's so I grew up on the far east side. I went to Lauren Central and it's definitely still worse out there in my opinion than over in the near west neighborhood. But um Max actually said something um that brought this to you mentioned traveling nurses like that neighborhood is so close to all the hospitals that are downtown so close to IU Indie Purdue Purdue Indie downtown is right there. You know it's probably 11 to 13 miles away from the airport. It's very close to a lot of things. So, um I don't know why people keep overlooking it, but I hope they do so I can keep buying. Right. Yeah. I live on the west side in Danville Southwest. So, I do go to the city. I have to drive right through every single day down 10th or Rockville, whichever. Uh just awful situ all the way from 36, take 36 from downtown Indie to downtown Danville. And it's like you see the same thing just constantly for miles. Yeah. What feels like it, but you can still buy a house there for about 100K that's totally livable and rent it out for the 1% rule. Yep. And it's just crazy to me that not many people are focused on that. I heard yesterday at our happy hour there was a guy he owns um I can't remember what street it is, but he's right in the middle of Hallville. 2100 a month for a midterm rental. Like what? Yes. 2100 a month. He's had no vacancy. It's been like two days. Nurse moves out. The accessibility is just like you said, you go right over the bridge. Literally right there. Right there. Yep. Yeah. I mean, the amount of jobs right there, you have to have jobs for, you know, people to pay rent. And like you said, both sides, I mean, there's just so much there. Um, I know that our mentor Rex, uh, he always has this like triangle that he shares, which is really interesting. Um, he's like, "This is the opportunity zone. This is just he's like it will not he was like you will not recognize it in 5 years which is from IU Health down to the new headquarters of Valeno right on the the west bank of the Right River. Yep. To the uh IMS the Motor Speedway which has new ownership um with Pensky. Yeah. Uh it's putting probably millions if not billions into that. So you draw a triangle there and the the the thoroughare is 16th Street. Mhm. So, um, you know, when I've been looking at commercial buildings, there's been ones on the market for 100 grand. Yeah. That could be 3 to 5 unit commercial buildings and cash flow very well and completely overlooked. Yep. It's just crazy to me. Yeah. It's it's the properties that cash flow the most typically don't look the best, right? Um, so people overlook them. Fair. People overlook them. They want they want to do what is sexy and not what really makes money. Well, I think Riverside gets the most noise when people talk west. Yeah. And like the triangle you just drew is actually cuts Riverside off. Mhm. When you come back towards Indie, which I always find that interesting. I feel like what gets the most noise gets the worst cash flow, gets the worst outcome in a lot of ways. Yeah. Um that's something something to keep an eye on for sure. Absolutely. Maybe I we'll move out of Christian Park and mobilize. I'll let you have your territory. But come on, man. Before we were um recording, you were sharing a little bit about you personally. Mhm. And the thing that struck me the most was you said I think AJ, our producer, was like, "What are you up to these days?" And you're like, "Rest." And I was like, "It's the end of February. No, I don't know anyone who's telling me they're focused on rest right now." Yeah. I don't I don't know a single other person because it's the it's like the middle of prime grind season for most people in real estate. Like they got big hairy audacious goals they're working on. We do. I mean, um how why? Yeah. I mean, so I I have very big goals also, but I do think it's very important that we don't get burnt out, you know, like there's no no need. We're young. There's no need to kill ourselves right now. Um, of course we're hungry, but um I can count on one hand how many times I've traveled since I started investing in real estate. Just been stuck in the grind. So for me um last year actually while while we were meeting I'm pretty sure I was still fasting at that time. Last year I fasted for 297 days until I uh executed the contract for the 13 unit. Um I didn't expect it to be that long at all. Uh but you know a 15-day contract 239 days. Yeah. Crazy. But um so I did that uh within the intent to acquire a 13 unit. Um of course this 13 unit has some uh government funds in it. So that made it a bit tricky. And I'll fast again for another property, but not for one that has government funds. It's like the majority of the year. That couldn't have been no food for two days. No, no, no. What type? It was more intermittent fasting. So, uh, for 188 days, I ate breakfast, fasted for 12 hours. Okay. Ate dinner, and then after from day 188 to 297, I did eight hours a day. That's awesome. Y, that's really cool. Not I don't know a single other investor who is fasting to get deals done, but it just speaks to the different impact you're trying to make and getting that spiritual energy even. Um, and you know, the Lord's blessing to get that done, I'm imagining. What What was the motivation there? I'm just guessing. But um, so I mean, I've always fasted. Um, I'm a spiritual person. Um, and I've know I've noticed the benefits of fasting early on and just, you know, staying staying focused, staying disciplined on what I'm trying to do. And when you're dealing with properties that have government funds, there's a lot of paperwork and stuff, compliance stuff that goes into it. So, you know, I I did it with the goal to just stay focused on what I was trying to accomplish. And last year, my goal was to, you know, execute the contract for that 13 unit. and was able to do that in December. That's awesome. Yep. Congrats. Appreciate it. Oh, but to answer your question though about resting. Um, how am I doing it? Um, you know, I have an automated email response set up for until December 31st. Um, I'm traveling more, getting more sleep. Um, listening to more books, you know, having more having more fun with friends. So um not necessarily just completely not doing anything just you know recalibrating I guess I would imagine your actual so the way I see productivity is there's a lot of um motion that doesn't always drive results and I'll see I'll pop open the laptop and be like all right I'm working it's 100 p. m. I got to do stuff and I just fart around full of people doing stuff. Yeah. I just you just end up doing motion and it's like I could have been fasting, catching up with a friend and still we're all pretty focused people. We're going to get stuff done probably regardless. Um it's funny. I just went on a 10-day trip to visit family in Florida and I my business improved while I was gone. I actually think I'd moved the needle more than the month before here working quote unquote more. But it's because a lot of what I I worked for like three hours a day. Yep. And did the only essential tasks and everything was the same if not better. That taught me a lot. Every time I leave actually it's the same thing. And when I go back there's stuff I have to catch up on. So like I couldn't do that forever, right? I do have to have some presence in Indianapolis. But I my goal I have like a vivid vision and it's to travel approximately a third of the year um by 5 years. Mh. Um and that's not to escape work. Um it's to maximize life, you know. I I really come alive when I travel and I'm more present with family, too. I just can relax um at 3 p. m. versus at home at 3 p. m. I really struggle to relax. I feel like I have to do something something. Yeah. And it's easier when you're out on the beach or something, right? Um so what you're saying like I totally resonate with right now. Yeah, man. You got to get your wrist, man. Yeah. Being around all the the high schoolers with High School Hustle is like reminded me of the grind and like the spark back in high school. I'm like, I got to make something out of anything, right? So, I'm just going to go mow like 10 lawns when I get out of school so I can make money to go buy what sneakers probably. Um, and I I'm reminded often of like I take uh try to take the entire month of October off. We have a friend who takes every Wednesday off. You're taking 2025 off. Like, you have to But you you move the the needle further when you're away always because you see all the problems. Yeah. You come back with more insight for sure. Absolutely. I don't want to say I'm completely taking 2025 off because I I I was mentioning earlier before we started recording that I I'm not only am I the owner, I'm the manager now. So once I moved back from Bloomington, I started managing all of my properties. So of course there's tasks and things that come up that I need to do, but for the most part I am trying to rest um as much as I can. Like I'm I'm okay with the slow burn. I don't need to grow extremely fast. I mentioned my goal by 2033 I won't even be 40 at that point. So I think a lot of people are in such a rush because possibly social media is you know kind of showing people in a light that's not really sustainable I guess. Um like there's a lot of people faking what they're doing on social media feel like they need to keep up with that you know. Um, but to your point about us being hustlers essentially and going to get things done. I think more more important something that's more important than you know the hours that you're awake. A lot of people always say I don't I don't get any sleep. I work so hard. I think what's more important is what you do while you're awake than the amount of time that you're awake. So yeah. Yeah. There's a good book on this that I have not read but has been mentioned many times to me is Essentialism by Greg something another that on my bookshelf. I haven't read that either. Yeah, maybe we need to open it up. I guess we'll have a book club. Yeah, it's behind me here somewhere. AJ just pointed it out. So, would you recommend it? Yeah, he's saying yes. So, okay. We'll we'll download Essentialism and get on the grind. Not the grind, the anti-grind. Um, we're the efficient or efficient grind. Yeah. Yeah. I've loved this conversation, man. Appreciate it. Absolutely. Me, too, man. Yeah. We have some rapid fire questions. They don't have to be answered rapidly. Mhm. Um, they're just predictable questions. Yeah. What is a um I'm trying to think of the way I want to frame this up. What is an underrated or um hidden gem place you like to eat in Indianapolis? M I don't even know if it's a hidden gem anymore, honestly. But Bodie. Yeah, the tie place. Yeah. Off. Just won a uh award I saw. Did it really? Yeah. You're not on social media. I can tell. It was all over the place. They posted on LinkedIn. Not on LinkedIn. I don't think restaurants are huge in LinkedIn. Yeah. Um the LinkedIn grind. You're on the LinkedIn grind right now. I've noticed only LinkedIn. That's the only social. What's the reason? I mean, I have other social media platforms. just don't use them. I've had them since uh undergrad, but I don't know. I just found myself getting more distracted on the other platforms than I do on LinkedIn. So, yeah, I try to stay as active as I can on LinkedIn. Yeah, I need to get on that. I'm like totally a ghost on there. I think I still had a high school picture when I logged in the other day to post something. Um, is a venture capitalism working there? Did that kind of spark the LinkedIn? Maybe it's cuz I didn't go to college. Maybe that's why I'm not on LinkedIn at No, you don't need to go to college, man. Um, but go ahead. I'm sorry. No, I want to hear what you're saying, but no, LinkedIn, I do think is there's more essential type of stuff going on there than maybe an Instagram or a Facebook. Yeah, Facebook, it's just like every time I go on, there's nothing productive business-wise that's going to happen there. Yeah. Nothing at all. So, what were what were you going to say? So I would I would say that I I was on LinkedIn prior to joining the venture capital firm, but I did get more active on LinkedIn. So what I do now is um a newsletter that I put out what I'm doing uh throughout the week. Um interact with, you know, people that are in real estate. Um yeah, I just try to be as present as I can be on the platform. you know, get uh get the benefits of the algorithm from, you know, responding to people's posts that, you know, resonate with me or are related to what I'm doing. And I get a lot of uh engagement from my newsletters. Yeah, I need we need to start posting our newsletters on there. What are we doing? So, you're posting an entire newsletter on LinkedIn? Yeah, just a link to it. Yeah. So they get the uh LinkedIn gives you the option to create your own newsletter and you can post like additions. You can do it daily, you can do it weekly, monthly, how whatever. Yeah, we usually do weekly newsletters. I have like one that I send deals out on which I I think I'm going to throw that one in the trash. It's it's too hard to keep up on and people can run their own numbers. Uh the other one that I'm way more passionate about is like uh similar to a five bullet Friday. Um, it's just I think of I have a spreadsheet of 150 different topics. Yep. And I click a little random wheel and then I write about whichever topic it lands on. So it could be like what podcast did I listen to this week that I love and I'll just write a blurb about it. What book that am I reading right now? Yeah. That type of stuff. Um, and that nothing fires me up more. But having I have to have the structure or else I'm not creative at all. So that's why I sat down and chat GBTE 150 different topics that I could write about, right? put them in a spreadsheet, found a random spinner to hit. Um, got to utilize artificial intelligence. Yeah, everybody. Absolutely. Wow. We could have a whole another podcast now. Uh, real quick, what would you say is the, uh, top suggestions to have a thriving newsletter for people that want to have one. We are going to do a whole topic about this soon. Yeah. Consistency probably. M a lot of people I I guess I'm actually guilty of this now for 2025. I haven't been posting as much as I have before, but um yeah, just staying consistent and not ignoring those that actually interact with your with your content. Um don't just leave them out to dry. Um take some time to to respond to those people that are took time to actually respond to you. Um but yeah, consistency and staying up on the engagement. I would say those are the two things that you should do. Yeah, I that's huge. I think you have to make it a low barrier too to to complete the newsletter, right? Like if you're writing a book every week, like you're going to burn out from it for sure. Um which is why you got to you got to find some sort of rhythm that works and that's why I change mine up all the time. I said that that's my flow now. Next week it'll probably something different, but the same people engage and like it. But yeah, and I keep it I don't make it too long. So my my newsletter is called the development digest. I talk about what I do daily, whether that's from property management stuff, what I'm doing for my consulting role. Um, and I keep it, you know, under seven minutes. That's where I try to like a seven minute read. Try to keep it under that. Do you email it out? So, LinkedIn automatically emails it to the people that subscribe. We need to get on it. I'm The first thing I'm going to do after the podcast is find you on LinkedIn because I don't know if we're connected and get on this. Absolutely. I'm fascinated. I have probably four to five newsletters that I read consistently. Yep. And I learned so much. It's what I use for my own newsletter, which the newsletter that I have has been a game changer. I've been doing it for now three, four years. It's the domino to everything in both of our businesses, right? It's just like how do you keep that narrative and that commentary running always, right? You're not losing people and relationships. Um, I'll have people that, you know, have dropped off in the relationship and they'll resurface from the newsletter. And even if they're not reading it, typically they might be receiving it and scanning it. Yep. And then finally, they're like, "Oh, actually, I do want to get into real estate. Oh, Tyler, he had the newsletter." Yep. So, it helps people resurface back into your life. It's huge for anyone who's I think an entrepreneur in general. That consistency, man. Staying at the top of people's mind. Like if you weren't sending out the newsletter and you know or they weren't receiving notifications about it and you know they weren't reading it before, if they get an email about it, you're back at the top of their mind. Yeah. Yeah. I think AJ commented on mine today. Was that someone else? He probably did. It was AK. Yeah, it was someone who was named AK. I thought it was AJ. I was like, he changed his name to AK. Dang it. Well, now you guys have a challenge. You got three newsletters. Just subscribe to. There'll be a link below. Yeah. What's an area of your life that you're working on growing? What's an area of my life that I'm working on growing? I can be more transparently. I can be more present in relationships. Like, you know, relationships with family and friends instead of being [Music] so obsessed or committed to what I'm doing. um I I could have a healthier balance of um improving my relationships. I think that's a huge one that entrepreneurs always Yeah. always are growing in because we we think different. So I I had a I just listened to a podcast Chris Williamson the modern wisdom. He said he has three versions of Chris. Dopamine Chris, serotonin Chris, and um it was depressed Chris or something. He's like let's ignore that one. the I can't remember the last one, but he was like, I'm trying to maximize serotonin, Chris, who is present, happy. He's like, that's the take mad mushrooms and go play pickle ball with friends, Chris. And he was like, all my memorable experience in life, I'm in that mode. And he's like, the dopamine one, he's like, that's my natural. Yep. I like want to chug caffeine and crank out work. And for us driven people, that's what we think we have to be, right? But no, like that's not living life necessarily. Nope. There's a time and place for that. Absolutely. And that really hit me pretty hard. I was like, "Yeah, I can see that for myself." How much how much am I in serotonin, Tyler? Like 2% of the time. Like that's a problem. Yeah. I feel like So, yeah, we got to change that, man. What is a habit that has changed your life? Habit that has changed my life. Wow. These are some tough questions, man. Um, I don't even know if this is really a habit, but I'm just a naturally uh intellectually curious person. Like I always want to know everything. Like whenever I get involved in something, I want to know as much about it as possible. So I think you know by just me being inquisitive or my ability to um effectively do research that could lead to me actually taking action and that leading to results. I think that that's probably the I don't know if you would consider that an habit a habit but that's something that has changed my life. I think it's a huge character trait for sure. There is a habit of asking questions in engagements, right? I sit down with people all the time and they'll be like, I guess, what do you do? Like start going down the tracks, start going and then, you know, kind of ping ponging the question back to them. And it's like, yeah, I'm a mortgage broker. Mhm. Cool. Why do you why do you do that? You know, and asking those questions to actually create a re a relationship and a conversation. But it I'm like dumbfounded how often I sit down for coffee and people aren't curious and don't want to know more. They want to tell you something, but they don't want to learn. And the best conversations are two people showing up to converse. Yeah. Converse and explore. You know what I mean? And I think it's a it shows humility 100%. You know, you can learn something from anyone. Yeah. Like I don't treat anyone any different. You know, the CEO of a company or a homeless person. Like I can learn from anyone. especially if they're older than me. They've lived longer than I have. They they've have more life experience than I have. So, yeah, I'm not I'm always going to try to learn something from from anyone that I have conversations with. I love that. Before we wrap, I got to know what was the number one selling snack in the vending machine. Oh, that's a great question, too. Uh so, uh do you know, are you familiar with the Fruities? Like the candies? Yeah, that was the number one for all the high school hustlers out there. Yeah. So, that was in the snack machine and the pop machine I think uh uh Fanta maybe was the number one. I could see that. Oh, yeah. Fanta. Yep. Well, uh where can people reach out to you, connect with you? Uh LinkedIn, Aaron Ler on LinkedIn. Um Aaron Lergmail. Those are my two preferred methods of contact. I love it. Yep. Well, great. That's another Roots podcast. Uh, make sure to subscribe, rate the show. It helps us get this to more people. And come to our next investor master class. Please do.

Episode questions, answered

Quick answers from this guide.

How did Aaron Laster get started in real estate with no money or credit?

Aaron could not qualify for a traditional mortgage, so he focused on building cash through wholesaling and used seller financing to buy his first rental property. He bought that first house from a church across the street for $15,000, putting $5,000 down and paying $1,000 per month for 10 months at 0% interest. He learned about seller financing primarily through BiggerPockets and a fraternity brother who had done similar deals.

How many wholesale deals did Aaron do in college and how did he find them?

Aaron completed 11 wholesale deals while attending Indiana University. He found leads by using the city GIS system to identify property owners, then skip tracing their phone numbers and cold calling them. He also sent out mailers as part of his outreach strategy.

What is Aaron Laster's 1,000-door goal and what does it include?

Aaron's goal is to own 1,000 doors by 2033, with roughly half dedicated to affordable housing. The portfolio will include small and medium-sized multifamily properties, commercial space, and light industrial real estate. He intentionally wants to avoid large institutional-scale deals to stay out of direct competition with major investment funds.

How do Low-Income Housing Tax Credits (LIHTC) work for developers?

In a LIHTC deal, investors receive a tax benefit in exchange for funding a development project. A syndicator brings in those investors, who might pay around 89 cents on the dollar, effectively providing the bulk of the project's capital. The developer still needs to secure a permanent loan or additional city grants to cover the full cost, and the developer fee is the first thing reduced if unexpected costs arise.

Why does Aaron Laster prefer acquisition rehab over ground-up construction?

Aaron prefers acquiring and rehabbing existing properties because there are often already tenants in place, providing income from the start, which both he and lenders appreciate. Ground-up construction requires navigating permits, potential rezoning, and coordinating multiple contractors, which he views as a more complicated and risky process. Acquisition rehab lets him avoid much of that complexity while still improving housing quality.

What Indianapolis neighborhood does Aaron focus on and why?

Aaron focuses heavily on the Near West neighborhood, including Haughville, where he bought his first properties while still in college. He attended neighborhood meetings and read city and LISC development plans, which gave him early insight into upcoming public investment in the area. He points to new construction, a brand-new library, and rising home values as signs that the neighborhood has shifted significantly in just the past few years.

How did Aaron get involved with Merchants Affordable Housing?

Aaron met Mike Petri at an awards ceremony and they connected over a shared IU background. Petri became a mentor and introduced Aaron to Janine Betsy, the CEO of Merchants Affordable Housing. Aaron was later hired as a fellow there for about a year and nine months, where he learned the details of LIHTC deals, HOME funds, and other affordable housing financing mechanisms.

What advice does Aaron give to someone choosing between wholesaling and buying rentals as a starting strategy?

Aaron says the right choice depends on the individual, but he personally prefers buying and holding rentals because long-term ownership is where the most wealth is built. He cautions that wholesaling is harder than social media makes it look, requiring heavy cold calling, mailers, and the ability to handle a high volume of rejections. For him, wholesaling was a tool to build capital when he had no credit or family wealth to draw from, not a long-term strategy.

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