Why New Investors Fail by Overthinking Deals (And How to Win Anyway)

Jesse Walters (00:00)

Nine times out of 10, they’re over analyzing the deal. If, you’re putting a really big buffer on that flip,

Even if everything goes wrong, you’re not gonna lose money on it. one of the first slips I ever did,

my $40,000 budget turned into an $85,000

I still made $800 I don’t overthink it.

be extremely conservative in your renovation budgets and just do it.

Michelle Kesil (01:53)

Hey everybody, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil. Today I’m joined by someone that I’m looking forward to chatting with, Jesse Walters, who is a full-time investor. So really excited to have you here on the show today, Jesse.

Jesse Walters (02:11)

Thank you for having me. I appreciate it.

Michelle Kesil (02:14)

Absolutely, I think our listeners are really going to take something away from how you’re approaching flipping the market and networking and everything that you’re focusing on. So lots to dive into.

Jesse Walters (02:29)

Definitely.

Michelle Kesil (02:30)

First off, for those who are not familiar with you and your work yet, can you share what your main focus is these days?

Jesse Walters (02:37)

Yeah, so I’m full time investing now. We started in 2021 and we’ve slowly built our rental portfolio. It’s like buying one deal a year from the traditional side and then we slowly ramped up to last year. We purchased…

about 15 properties in 2025. That’s about half were rentals we kept and other half were flips. And yeah, that’s my full time gig now I have roughly, I think 18 doors in our portfolio with a few more pending under contract that should put me closer to 30, I would say in the next few months.

Michelle Kesil (03:18)

Amazing and what markets are you operating this in?

Jesse Walters (03:22)

Yeah, I’m in central, Missouri. ⁓ I live in Columbia, which is home of University of Missouri college town We have a few other smaller colleges too It’s pretty active area a lot of people moving in and out for the schools with a few hospitals things like that so that really keeps our economy growing and then there’s some smaller towns outside of Columbia that I operate into that Have really good rent potentials and I’ve kind of fallen into that it works out pretty well for us,

Michelle Kesil (03:52)

Awesome. How did you get started as an investor?

Jesse Walters (03:56)

It was kind of an accident. ⁓ So what really sparked it I think in the beginning… ⁓ Well let me back up. I actually flipped the house when I was 18 years old. ⁓ It was kind of like one and done. ⁓

I graduated high school in 2008, so it was like right when everything was crashing And you know with first year in college 2009. It’s like the economy’s going down and here. I’m getting a college degree ⁓ I actually came across a house that I bought it for fourteen thousand dollars in 2009 and

I didn’t do anything to it. I just put it on the market. We sold it for 25 grand. So I just made a few thousand dollars on it and just kind of went on my way and I went back to college and didn’t think about it anymore. It was kind of like why they didn’t light bulb and go off at that time. I like maybe I should just keep doing this. I didn’t. I just went to college and kept going. But fast forward to 2017 my wife got licensed in real estate. I was working in a different job and

she was growing a real estate business in that way and she got really successful with it over the years and so in 2021 when rates were super low things like that we were helping she was helping other investors buy properties things like that.

We started doing the math on it. like, this kind of makes sense. Maybe we should be doing this too. And so we bought our first rental in 2021. ⁓ It was nothing fancy. It was on the market. We put 20 % down, like 30 year fixed mortgage. Like it was, we didn’t, nothing creative about it. ⁓

And it cash flowed, it’s like a three point something interest rate for 30 years. And we just kind of went with it. And then after that, I got the bug. I was like, maybe we should keep doing this. So we bought another rental in 2022 and we bought a fourplex in 2023. And then in 2023, we bought another like condo and…

It turned into it was supposed to be a place for my wife’s grandmother to live and because she was getting some health issues things like that and then she ended up not moving in there. So I was like, what do we do with this thing? I’m like, I can I can rent it but it’s not going to be great. So I ended up flipping it. It was like an accidental flip. I was like, I just I put a little money into it made a nice and we sold it and I put 17 grand into it and then we made 23,000 on it profit at the end. So it’s like

And then it all came back like, wait a minute, I did this back when I was 18 years old. Like, hang on, I can keep doing this and keep going. So, and that’s what sparked it from there. That was 2023, 2024, I think I did three flips, four flips. And then yeah, 2025, I did seven or eight, but I also purchased six or seven rentals in that process too, that we’re all not turnkey. You know, we’ve renovated all 15 of those houses last year and kept going that way. And the rest is history.

Michelle Kesil (07:50)

Awesome. What are maybe some challenges that you’ve experienced as an investor that now looking back in hindsight, you have the lesson?

Jesse Walters (08:01)

Yeah I would say one contractors like I I think a lot of investors have issues with this but like they always come and go I’m I used to rely a lot on like those and now it’s like I used to have a guy I’m like hey he’s really cheap at doing this like like you know if it’s like painting a house like I can get it done for half the price of the normal guy with this person over here but

then all of sudden he just gone. Like I can’t get a hold of him, no phone call, anything. But when I bought this house, I underwrote it with that cheap paint labor. And now I gotta go pay full price to someone else. And so now ⁓ that was a challenge in the beginning. And now I’ve gotten to where like, I just underwrite it of like, if I’m paying full price for everything, and then if I get a cheaper, great, you know, I go that route. ⁓ But another obstacle I keep running into is

There’s a lot of people out there trying to I see a lot in wholesaling, but they’re trying to Get these deals make a quick sale and quick profit on them And they’re not really looking at the entire situation like what? One the biggest ones the families that are living there either tenants or their owners things like that if you know They’re just trying to get to the next chapter they might be in a financial situation or I’ve had divorces or like it’s a death in the family things like that and Wholesalers don’t

I don’t want to blink at all. There’s good wholesalers out there, like I’ve ran into a few more than not. I’ll say that more than not in the last few years that they’re just trying to sell it.

the owner of the property doesn’t actually know what’s going on and then it actually ends up killing the deal and no one gets it and they get up end up in a more worse financial situation and it’s just a bad deal and I’ve kind of made a point in last couple years where like I’m just trying to get ahead of the wholesalers just so I can get there and talk to them. A lot what I can do ⁓

a lot of those people. I’m a licensed agent now. So between my wife and I either I go to them. I never just flat out say I’m buying your house. This is what I can do. Like I’m always offering to list it as well. I’m like hey I can list it for XYZ or I can buy it at this price. I give them two different options and a lot of times they still let me buy it anyway because they’re in a financial situation. So it’s I never really lose out on an opportunity there from an investor standpoint but it’s it at least gives them options and I try to see it through and things like that. And the biggest

challenge is yeah those wholesalers get to it first and I can never get to the seller to like negotiate with them and try and the best path for them and it just ends up killing the deal and we lose it all anyway

Michelle Kesil (11:14)

Right? Yeah, that makes sense. So what do you feel are some main keys that have made the biggest difference in allowing your business to be able to grow and scale and run smoothly?

Jesse Walters (11:31)

I think the biggest thing is networking. ⁓ Not just like social networking, but also ⁓ like face-to-face networking, like in our community. That has been huge for us. So like the 15 deals we bought last year, seven or eight of them were not from like paid advertising. Like I did mailers, we did like, know, pay-per-click, like the Google search, things like that. But like,

I’ve had a lot of like even other real estate agents come to me with deals. ⁓ Just people online send me houses like, like my neighbor’s house is vacant. I’ve talked to them a little bit, but they’re wanting to sell it. Things like that. And like it’s all free advertising. like, and those tend to up being like the best deals. Cause like you can get in of the seller, things like that. But like we put a lot of emphasis on getting to know high performing real estate agents in our area.

And then also social networking so Facebook Instagram things like that. I’m kind of a hypocrite to it I’m not the best at it. My wife is really good at it, and it’s proven itself in that way and You know I think it’s preached a lot in this industry of like you know you have to put a lot of money in advertising You know with mailers things like that, and you have to kind of weed through all the crap to get there, but like we’ve

of found a way around that in a sense like so we’re not in a huge huge town it’s not like a new york or things like that like columbia is like a town of 150 000 people not small but it’s not huge either so you can get to know a lot of people pretty quick that do most of the deals in our area and

Once you kind of get in that and really focus on that like people to start sending you stuff that’s quality leads and that has been a huge part of our success over the years is like it I mean they’ll they’ll call me before it even goes on the market like hey I’ve got this house like it needs some work. I know this is something you do. I want to offer to you. They want a quick sale and I’m going to put on the market next week but if you want it it’s yours. So like I literally beat everyone to it before and you know before it gets in a bidding war or anything like that. So it’s and that’s it’s been pretty

to see that come through.

Michelle Kesil (13:42)

Definitely, are there specific networking strategies or it’s just being connected with people in your local area?

Jesse Walters (13:52)

Yeah, realtors are kind of a low hanging fruit there. Like they post their cell phone numbers everywhere. Like you can go find their cell phone number in five minutes. Like I would just call them, tell them what you’re doing. And ⁓ fortunately for us, we’re also agents. like, you know, we can kind of relate to them in that way, you know, things like that. We’ve might’ve worked with them on a different transaction in the past, things like that. So we’ve had that kind of warm introduction. So we kind of have that leg up for a lot of people, but same time, like a realtor.

They’re just trying to make a sale. you know, as long as they’re selling houses, they don’t care. Like if you tell them like you’re an active buyer, you’re wanting to buy multiple homes this year, like they’re going to keep you at the top of their list as long as you can prove it too. So like if they bring you a house and you pick up your phone, you answer your questions, even if you don’t buy it, tell them why you’re not buying it and XYZ, they’re going to keep calling you. And because like they know you’re reliable, you’re going to pick up your phone. And when one does come up, you’re going to buy it and go. And if once you get that rinse repeat, the realtor’s figure it out and they will just

keep calling you with other things.

Michelle Kesil (14:51)

Definitely makes sense. What are you most focusing on solving or scaling to next in your business?

Jesse Walters (15:40)

Yeah, I’m at a weird point in our ⁓ venture here. So we’ve been building it for five years. Yeah, we’re at 18 doors. We put a decent size deal under contract. It’s not huge, but it’s actually an old motel in our area. We’re gonna convert it into an apartment building. It’ll be a 10 unit apartment building when we’re done. And with that…

⁓ Once that gets completed and we get that stabilized, we’re going to have this our portfolio at a point where

It’s where I kind of wanted it to be like I wrote down my goals early on of like, you know I wanted XYZ things like that and like for me it was never really a number of doors It was always just like a rent roll like how much rents coming in per month and for me was like thirty thousand dollars like if I can get to thirty thousand dollars a rent roll then from there I can start working backwards and start like paying down debt and like because once that once I start paying off those loans the cash flow starts going way way up and then that is going to allow us to we’ll never retire but

It’ll allow us to work because we want to not because we have to that’s kind of our little slogan You know, we’re not relying on commission checks or you know things from the realtor side of things It’s like when we have the rent income coming in even when you take in, know vacancy maintenance things like that if I get a rent roll up to 30,000 and start paying things off that’s gonna help set us up for ⁓

a very healthy lifestyle afterwards. even with all the things coming up that you can never expect, even the things you can’t expect, putting a big roof on five of the properties, it’s not gonna be a big deal at end of the day. So we’re getting to that point in 2026. We will be very, very close to hitting it with that hotel deal. So.

What I’m trying to do is probably in, it’s working out pretty well, I think. In 2026, there’s gonna be, I think a lot more deals come online. Just the way the market’s going, it’s just a lot slower than it was in last five years. And I think there’s gonna be a lot more motivation to sell. You’re gonna be able to get more deals. I’m gonna be focusing more on the flip side. And the profits from those flips are gonna start going back into the rentals we already own and paying down debts and getting cash flow up to get really lean and mean. And then,

in the future if rates come down, things like that, and if I want to refinance, I just have that flexibility in the future. I can definitely do that and go for it.

Michelle Kesil (18:04)

Yeah, absolutely. Makes sense. That’s exciting to be in that place where you have the flexibility to do that.

Jesse Walters (18:08)

Yeah,

yeah, I didn’t think we would be able to do it in five years. We got there a little quicker than I thought, but we really just put the put the pedal down in 2025. And that got us a huge influx in our portfolio and in flips to discuss a lot of experience. And it just goes to show like I think with that networking it

The deals were coming in, we were able to react and be able to buy them. We had a small local bank on board. I was able to get some family friends as private investors and we just started buying and it worked out.

Michelle Kesil (18:45)

Definitely. What’s some advice you have for maybe people that are just starting out and looking to also, you know, level up?

Jesse Walters (18:54)

Yeah, people starting out, I would just say, I’ve come across this a lot with people, they’ll call me and like ask me things to do.

Nine times out of 10, they’re over analyzing the deal. If, you know, there’s some deals they bring to me, I’m like, I probably wouldn’t do that, don’t do that. But like others are like, this is actually a good deal. Like they’re just overthinking it. I’m like, hey, like you’re doing everything. like, as long as you’re putting a really big buffer on that flip, like,

Even if everything goes wrong, you’re not gonna lose money on it. An example I always give, one of the first slips I ever did, it was a little bungalow house, it was built in early 1800s. I had a renovation budget of $40,000 on it.

When we started ripping the floors out, it turned into be like a lot of wood rot, termite damage, things like that. So we had to literally rebuild this thing from the dirt up on from the inside out. We had to build a deck inside this house because it was all dirt floors underneath it. There was no concrete foundation or anything. So my $40,000 budget turned into an $85,000 budget at the end of the day. And that deal, ended up…

keeping it for 11 months. I was only planning to keep it like four or five. I had 11 months. We went way over budget. I still made $800 on that deal because I just had a huge buffer on the thing. it’s like, so that being said, like as long as people are doing that, like I don’t overthink it. Like

be extremely conservative in your renovation budgets and just do it.

Once you get one, you get more comfortable, you keep going, you keep going. And that’s the biggest hurdle I see a lot of people getting started at. just, they’re worried they’re gonna lose money on it. I was like, well, then take another 20 grand off and just make the offer. And if you end up buying it and you spend extra 20 grand, you’re right back where you started anyway. So like, or they just say, no, you move on next deal. So like, I think you just gotta start making offers and go for it.

⁓ For people trying to scale, I think the biggest thing for me was the networking side. ⁓ If you can get in with some of those high performing agents in your area that just know a lot of deals, they’ll start calling you and you don’t have to put a ton of money into marketing. ⁓

I’ve had people tell me like yeah, you need me putting like 10 grand a month of marketing Well, like a lot of people don’t have 10 grand a month to go to marketing And so like if you can do this like it’s a slower play don’t worry It’s not gonna happen tomorrow But like if you can do this consistently just you know for the next few months and like and by this time next year you’re gonna have people calling you with deals and they’re absolutely free and Like if the realtor is getting paid on commissions when you buy it, you know if everyone’s getting paid in the day if everyone wins and You get a lean running machine that keeps feeding you

needs.

Michelle Kesil (21:44)

Yeah, absolutely, I think that’s some great advice and yeah, it’s important for people to just take that action and get started and yeah, see how things flow from there.

Awesome. So before we wrap up here, if someone wants to reach out, connect, learn more, where can people find you and connect with you?

Jesse Walters (22:10)

Yeah, I’m…

Most active on Instagram, so my handle is jesse.v. You might be able to search my name Jesse Walters. might pop up. don’t think there’s too many of us out there. Follow me on there. Shoot me a message. I’m happy to reach out or communicate with you. I’ve had a lot of people call or message me to ask me questions. I’m happy to do that. It’s fun to do.

I’m not going have all the answers but I’m happy to talk with you about it and just at give you my opinion what I would do and what I wouldn’t do or share you know mistakes I made anything like that so I’m happy to do it.

Michelle Kesil (22:53)

Perfect, appreciate your time, your story, your perspective. Thank you for being here.

Jesse Walters (22:57)

Yeah, thank you. I appreciate it.

Michelle Kesil (22:59)

Of course, and for the listeners tuning in, if you got value, make sure you’ve subscribed. We’ve got more conversations with operators like Jesse who are building real businesses. We’ll see you on our next episode.