Diary of an Apartment Investor

Why a Bad First Deal Can End Everything with Keith Heckman

• Brian Briscoe • Episode 582

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One bad first deal can damage trust so badly that you never get a second chance.

Many investors focus on finding deals without fully appreciating the long-term consequences of getting the first one wrong. In this conversation, the discussion centers on why early decisions carry disproportionate weight — not just financially, but relationally.

If you’re serious about building a multifamily investing business instead of chasing one-off wins, this is exactly the type of thinking we go deeper on inside the Tribe of Titans multifamily investing community, where investors work through real decisions together and pressure-test them before mistakes happen.

What You’ll Learn:

  • Why protecting investor trust matters more than speed
  • The real risk of scaling the wrong asset type early
  • How capital raising fits different life constraints
  • Why mindset shifts determine long-term success
  • What most new investors misunderstand about their first deal

The conversation walks through how experience, mentorship, and intentional partnerships shortened the learning curve and reduced downside risk — while still allowing forward momentum.

Inside the Tribe of Titans, these discussions continue with live interaction, real-world context, and direct feedback from operators actively doing deals. If you’re ready to move past theory and build with intention, that’s where the next step happens.


About the Guest:

 Keith Heckman is the owner of KTAH Properties LLC, and has been investing in real estate since 2018. He began with single-family and small multifamily rentals, fix-and-flips, and private lending before transitioning into commercial multifamily in 2022. Keith is currently a general partner on 148 units valued at $18.2M and a limited partner in apartment and resort properties across Texas, Michigan, and North Carolina. 

Learn more about him at: https://www.ktahproperties.com/, or Email ktahpropertiesllc@gmail.com


About the Host:


Brian Briscoe is an apartment operator and founder of Streamline Capital, focused on acquiring and operating multifamily properties in the greater Salt Lake City metro. He hosts the Diary of an Apartment Investor podcast, where he shares real-world operator insights and decision frameworks for aspiring multifamily investors.

If this conversation resonated, there’s more happening inside the Tribe of Titans. It’s where serious investors move beyond surface-level content and into real discussions that drive action. Visit https://www.thetribeoftitans.com/ to learn more.

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Brian Briscoe:

Welcome to the Diary even apartment investor podcast, a show where we cut through the noise and talk about what it actually takes to build a real multifamily investing business. I'm Brian Briscoe, apartment investor, operator, and founder of Streamline Capital. And this podcast is built for the aspiring apartment investor who wants more than just theory. We talk about raising capital, closing deals, managing assets, and making the decisions that separate dabbling from building something that lasts. Now, if you're serious about taking the next step, this conversation continues inside of the Tribe of Titans multifamily investing community where investors work through real deals together with live discussions and direct support. So let's get into today's episode. Welcome to the Diary of an Apartment Investor Podcast. I'm your host, Brian Briscoe at Streamline Capital. Really excited for today's show. We've got none other than Keith Heckman on the line with us today. So, Keith, what's up? How are you doing?

Keith Heckman:

Things are good, Brian. Um, just enjoying the cold weather in Michigan. How about for you?

Brian Briscoe:

Yeah, yeah. Well, I think you guys got a real cold snap going through right now. You know, we're actually sitting in the 40s today in Idaho, so uh that's not terrible for December.

Keith Heckman:

No, that isn't bad. Yes, we're in the mid-20s and we did get a good amount of snow last week, but that's all right, it makes it nice for deer hunting.

Brian Briscoe:

Yeah, and round here, you know, snow makes it nice for you know, skiing, snow. I mean, any any one of those winter sports that you know combine mountains and snow. So yeah, the resorts closest to me are not open yet. So hoping for a couple of you know snowstorms here coming up. But uh that said, let's talk a little bit about you today. And when I say a little bit, you know, it's gonna be mostly you talking, but tell us a little bit about yourself, your background, and how you got into real estate.

Keith Heckman:

So I'll skip into where I got into real estate. Uh back in about 2016, I decided to get my builder's license as well as my real estate license because I thought I would do some flips. My dad was a builder, so I had that knowledge and expertise getting at from him. So I just decided why not buy my own places, fix them up, keep them as buying holds, or just fix them up and flip them and just keep everything in-house and kind of vertically integrate on a small scale. That started out okay, uh, but I actually got busier just working for other investors and just uh regular everyday customers for remodels and um found it difficult to get into real estate. But in 2018, I finally pulled the trigger and bought my first single family home for a long-term buy and hold. Uh that went well. Then I realized how I could use my retirement funds to actually leverage quicker and buying more real estate or using other people's money. So then I started buying a few more duplexes and some single family homes. And then during that time, I if I found a good deal for um a flip, I would buy that, fix it up, flip it, and then sell it. And then also learned about private money lending from some other mentors. So I used my I started using my retirement account to lend money to other real estate investors and become the bank. And I realized um that was really nice too, to be able to spread out, not only have different streams of revenue between the buy and holds, the flips, and then that long-term longevity of being the bank, that's gone really well. So that's what I did initially, and still have all but one of the original single family homes and duplexes. And I didn't buy a ton. I actually only I had four at the time, and now I have three because I decided to scale a little quicker going into some larger real estate.

Brian Briscoe:

Yeah. So when you say that, you mean you you sold one of the multifamilies to help you jumpstart the multifamily part? Did I say that right? Sell a single family to jumpstart the multifamily.

Keith Heckman:

Is that what I understand? From the standpoint of getting into the GP world, yes. I actually used my retirement funds to buy into some other deals as a limited partner first.

Brian Briscoe:

Okay.

Keith Heckman:

Um, because I realized that I wanted to scale faster. And the reason that happened is about five years ago, my wife and I started a five-year plan of how do we partially, if not fully, retire her within five years. And so I started doing math after talking to other real estate investors and mentors, and it was either buy more single family doors or jump into commercial real estate with multifamily, and I realized that there was way more work involved in those single family homes and all those extra roofs. And when a tenant moves out, you got a vacant property, and that's it. There's nobody to soften the blow of vacancies. And so I did some research on multifamily investing, and that would have been in 2021. Did some investigating and then ultimately ended up buying a uh Michael, I'll give him a little plug, Michael Block's book. Yep. Um, the little yellow book, like a lot of people have read, and uh just really decided to dive in with his mentorship program. And I'm glad I did it. I'm glad I did it because it was helpful for multiple reasons. It gave me access to other investors throughout the country. You may not, I don't know if you remember or not, but that's actually the first time I met you at his Deal Maker Live when I went there in 2022, I believe, or 2023.

Brian Briscoe:

I think that's the last one I attended. Yeah.

Keith Heckman:

So you grew up on stage speaking.

Brian Briscoe:

Yeah, yep, yep. I was also a Michael Blunt coaching student, which uh, you know, most coaching programs, when they have these conferences, they put their successful students on stage to help the people in the crowd and, you know, make a determination to, you know, throw some more money towards the program. And, you know, I was all about that. But I did well in that program. That program did well for me too. And I think it's an important part of everybody's journey is getting that coaching.

Keith Heckman:

I felt having the mentor and that coaching was more beneficial to me not making mistakes in this space because I knew if I made a mistake in the single family sale or even a duplex or a quad, I wasn't gonna break the bank with my wife and I. But I knew if I made a mistake jumping into multifamily and getting a 96 unit building under contract, that was not a good deal. Not only could it ruin us financially, more importantly, it would probably have stopped even start because people that might have invested in that deal would have just been burned by it and maybe never invested again with me. So it could have, you know, stopped my journey before it even started. So that was even almost more important to me than the relationships I was able to get across the country with access to his program.

Brian Briscoe:

Yeah, absolutely. That's part of the reason why I did it myself was I didn't want to have a bad first deal. I I kind of wanted to fast forward the success, you know, instead of spending two, three years of figuring it out, get a coach and kind of take that two to three year time frame and cut it down to maybe a year or so. But uh anyway, yeah, lots of good stuff to say about coaching in general. And you know, Michael Blanc, he's uh somebody I've always I've considered a mentor ever since. But anyway, so you got into the coaching program, you did a couple of passive investments. Let's talk about some of your GP spots and you know I'm excited about this part. So for everybody else, Keith uh partnered with us on one of our deals that we recently closed on to. So anyway, let's talk about uh what you've done so far on the multifamily side.

Keith Heckman:

Absolutely. Because of those relationships that I was able to create through that program, well, I met Kyle McCune at the DMILACA Live as well, but he and I stayed in touch. So my connection with him led me to connect with a couple of other operators in Charlotte because he was on a deal as a KP. And just from connecting with them through that program and getting to know them and you know, vetting them as operators and us getting to know each other when they had a deal available. Uh, they had offered me an opportunity to help them raise capital as well as invest. Uh, so I was able to get on my first deal in 2024 with them on an apartment deal in Charlotte, a 56 unit deal, and helped raise capital for that and part of the GP team. So now, you know, I'm able to learn, which is one of the most important things I wanted to do, is not, like you said, uh shrink that gap of getting in a deal and the learning curve, just decrease it. So I've been able to stay in touch with them as being an asset manager on that deal and part of the active management. Once it closed, there's lots of things I've learned that it would have potentially taken years to get to that point had I not partnered up with people. So that was our first deal. And then we also uh that same group ended up getting another deal under contract in North Carolina, and that one closed in 2025. So that was, I want to say first September, October time frame. That was a 96 unit deal. Um, so that one I raised, you know, continue to help with raising capital, and that's been my main role is raising capital as a partner for the GP team alongside investing some of my own money in those deals and then being part of those weekly asset management calls just to start learning the behind-the-scene things, uh, and then eventually be able to become more involved, uh, whether it's through risk or you know, someday, you know, be a KP once I get to that point, and just then at some point in time being part of the asset management team day to day. Those are the two with that group, which then led me to connecting with you for the Westmont deal that closed and helping to raise capital on that one as well as investing alongside. And so that one I'm you know excited to be part of those weekly calls that we have as the team to as we're stabilizing and getting those units turned and everything to a stable asset that goes into value add properties.

Brian Briscoe:

Yeah, and it's eye-opening, you know, when I started out, maybe it's not eye-opening for everyone else, but it was eye-opening for me when I bought my first value add property, you know, how much work it actually took, you know. Uh I think uh up front I thought it was simple. Hire a property manager, hire a general contractor and go, you know, and then we could sit back and watch. But yeah, very eye-opening, how much work is involved. Something else I'll say about, you know, the way you decided to do things, you know, raise capital for a couple deals first, get some experience, and then, you know, potentially add to your skill set while you're doing that. I think that's probably the best way. If I if I could come up with a one size fits all for everybody, that would be it, to be honest with you. And so just curious, why did you decide to raise capital? You know, there's lots of different ways you can get into multifamily. Why did you decide on the route that you went?

Keith Heckman:

It's interesting because I remember sitting in that deal maker live and that you know, someone got on stage and talked about there's multiple things. You could either be the person who wants to network and raise money, you could be the hands-on asset manager, or you could just be the person that's doing the construction. You know, if you want to get in there as a part of the manager side of things. And I remember sitting with a group of guys that I got to meet there and got to know, I said, Oh, that was a capital raising. No, I'm all day long gonna underwrite deals. I'm gonna be the guy that's gonna be behind the scenes. And that's what I started with. I started, you know, reviewing all the deals, talking to brokers, and I enjoyed it. But what was challenging is around that time I decided for many reasons that I was gonna get back into medical sales. So I was gonna leave working for myself as a remodeler, contractor, realtor, and go back into medical sales because I had about 17 years of experience in it prior to getting my uh builder's license. And there's just an opportunity that presented itself from a past buddy that I worked with. So I got back into it and I realized, wow, when you're in a W-2, you do spend a lot more time on the stuff that they require since they're, you know, paying your bills, so to speak, or giving you a paycheck. And I realized really quickly it was going to be very difficult to be so much hands-on with underwriting talking to brokers. I just thought, you know, I felt it was a better avenue for me because there was more things I could set up on autopilot with capital raising to stay in touch with people that would then allow me to have more of those one-on-one conversations as I started to develop relationships with possible investors. So it really came down to a what was going to be the best avenue for me to get involved. And I realized it was capital raising, which is ironic because now I enjoy it, even though initially I said I really don't want to, because like a lot of people that are probably going to hear this, you feel like when you're capital raising, you're asking people for money and you are almost trying to convince them that they should get in this deal. And after I've been doing this for a little over a year, I realize when I talk to people now, it's different. It's actually, hey, I have a opportunity for you to invest in this. If you want to, great. If you don't, no big deal, I'll move on to the next one. So I feel like we have an opportunity for them to invest in a deal, and I'm not asking them for money, so it doesn't feel weird. It's just so my mind shift has changed.

Brian Briscoe:

Yeah, you know, when I first started raising capital for my first deal, you know, it was similar. I felt like I was asking people for money. Something that happened yesterday, you know, I talking with two brothers on the phone that are, you know, both investing in in one of our opportunities. At the end of the call, they said, Hey, Brian, I really appreciate this. Thanks for letting us in. And it was stuff like that very beginning when people thanked me for opportunities that I realized that I made that own mindset switch myself. And I realized I'm giving people something that they want. You know, I'm not ha I don't have to convince people to do something that I want them to do. And then uh about uh, you know, capital raising with a full-time job versus underwriting or even asset management, you know, if you've got a nine to five, it's really hard to do the underwriting. That's when brokers are, you know, working. It's really hard to do the asset management because that's when your property managers are working. But if you want to try to raise capital with a W-2, well, guess what? You're off when everyone else is off. You know, so there's lots of good reasons to raise capital up front. And it gets you into a lot of deals that you wouldn't be able to do by yourself, you know. So everybody's really, really happy to let the guy that can raise two, three, four hundred thousand, you know, up to a million dollars into the deals.

Keith Heckman:

So yeah. And the thing that I know you know this, yeah, and probably a lot of the people that are gonna listen know this. You know, I I want it to be clear, I didn't uh I didn't choose this route because I'm saying, oh, it's easy. You know, it's not you know, I'm always saying that because I replay what I said in my head, but I yeah, I don't want people thinking that I took that route because I thought it was gonna be easy. It just was, like you said, fit my needs better. And then the other thing that people may not know if they're new to this is you know, you can't just come in, raise money, and then walk away. You have to actively stay on that deal to stay compliant. And I want to anyway, to for all the reasons you said to continue to learn. And that is one of the reasons that I'm partnering up with people such as yourself that's been successful, the group out of Charlotte. If I'm new and I'm partnered up with some people with experience and success for turns and full cycle deals, that gives the credibility to the investors I talk to to say, yes, I'm newer, but here's who I'm partnering with. So look at them and look at their track record. Because one of the things I've started to do, I mean, you're a great example. I I wanted to stay focused on the group in North Carolina as an operator because it, you know, I got to know them and trust them. Now through them and through knowing you over the last few years, I know and trust you. And so now I'm moving into because you're in a whole different market. You're an operator I trust, and now I can partner with you on deals. And I'd love to find, you know, a couple more across the US in pockets where are good investments because they're boots on the ground. And then that gives me the comfort knowing any of those investors that trust me. I'm trusting the people I partner with. Trust is we're only so good as our last deal, and we've got to be able to protect people's capital. I know it's not perfect what we do, but if we partner with the right people, we're gonna have a better chance of protecting that capital and putting it to work.

Brian Briscoe:

Yeah, couldn't have said it better. Couldn't have said it better. Yeah. And then like I said, my one size fits all was raising capital first, but just reiterating what you just said is you know, if you're raising capital, you don't have to be where the deals are. You have to have trusted operators that are operating, but you know, you've got a lot more flexibility to invest in multiple areas. I raise capital, but my main role is putting the deals together and operating them, which I'd recommend that if if that's what you're doing, you draw a two or three hour circle around where you live. And that puts some limits on there as far as you know, where you can invest, because you have to be on the ground. You have to be able to get to the properties frequently, you have to be able to, you know, sit kneecap to kneecap with the brokers and a lot of time you're investors as well, but good stuff there. So, how about this? What were some of the challenges you had starting out capital raising and how have you progressed since that first capital raising?

Keith Heckman:

Fantastic question because one of the biggest challenges I think we are all going to face is when you get started. I mean, you really only have your circle of family and friends, most likely that you can go call upon. So there was limited opportunities. And so the challenge I first felt was anyone that expressed interest through conversation of, yeah, when you have a deal, give me a call. When a deal came up, I would send it to them and you know, they would say to me, Oh, this doesn't fit my criteria. And because I had limited investors, I was more focused on trying to fit that square into a round hole or whatever square peg into a round hole. I was just so focused, like a dog with a bone, trying to change that investor's mind. And that was one of the biggest things for me to realize, like I said a few minutes ago, you know, hey Brian, it's Keith. I got a got a deal in North Carolina. Here's what the parameters are. You know, what are your first thoughts? Oh, hey, Keith, it's not a great time right now. I just deployed a hundred thousand dollars. I'm I'm happy. Okay, no problem. I'll call you the next time I have a deal. That's what I've gotten to now is being able to just say, no big deal, I'll hit you next time. This one doesn't work for you. And it's a good feeling when you grow that investor base. So that was the biggest challenge, is getting over trying to convince someone this was a deal that was right for them. Second biggest challenge, it kind of goes hand in hand, is just not having a huge investor pool because you know, once you hit the family and friends, you can tap out your resources. And then, you know, someone comes to you and said, Well, I mean, this happened with you. You had reached out to me and asked about raise it for the deal. I'm like, you know, I don't think I can do it right now because of the deal we just got done. And then it worked out I actually could help you out um when you needed some help with a different deal. Because I think that was maybe a different deal you reached out. But having more people now is nice to open up opportunities. I mean, for me, another big thing was just getting out of my own way and overthinking things because it is, I don't care what you do for a living. We are building relationships with people. If we build relationships, get to know them, then know like and trust. I know it's a, you know, everybody in their brother says that, but it is the reality. If I get to know you, you get to know me. That doesn't happen over time. It but it's got to consistently happen where there's touches.

Brian Briscoe:

Yeah. Yeah, absolutely. Absolutely. Over time, you learn things that work better. You learn how to preserve those relationships. You know, a lot of what you said, you know, took me back to my first couple of capital raises. Why, you know, it's the same thing. It's like, no, no, this is a really good deal for you, right? You know, it's uh trust me, this is a good deal for you. Uh, like a used car salesman, but when you focus on the relationship, and that's something we stress is relationship comes first, deal comes second, you know. And so we want to make sure that we walk away from every phone call with an investor with a better relationship. Sometimes that means telling them, you know, hey, this isn't the right deal for you. It's a strategy that'll work a lot better long term. You know, it sometimes you have to do a little bit more work in the short term, but we're in it for the long term. That's why we do real estate.

Keith Heckman:

Absolutely.

Brian Briscoe:

All right. So a couple of questions to finish things up. Question number one what's next for you?

Keith Heckman:

Big thing is we're we're finishing up uh, you know, capital raising for the Westmont deal. We're close. So that's priority number one is to get that fully funded. And then uh the other one uh just got another deal under contract yesterday. The ink was uh signed in in the north, well, it's just outside of North Carolina, and it's just outside of Charlotte, MSA and uh Shelby. So that one's gonna be coming live here in the next uh few weeks that we'll get some webinars put together and start uh presenting that to you. Investors, and that's uh you know, right now that's another one I'll be putting some of my own money in, which is what I like too about all the GPs I partner with is we put our own money in there. So people need to understand that because not every GP team will put money in a deal. So I look to partner with people that are gonna put their own money in, myself included, because that means they believe in that deal just as much as they're trying to sell an LT. That's what's next, and then just continuing to grow, uh just to continue to grow my investor pool by reaching out and connecting with more people and just developing relationships.

Brian Briscoe:

Awesome. So more of the same, just at a higher level.

Keith Heckman:

Yes.

Brian Briscoe:

Awesome. Well, next question. If you had to give advice to somebody who's just starting out, what would that advice be?

Keith Heckman:

Definitely education, but I would say don't do the analysis paralysis. I mean, education, find a mentor and then take some action because you will make mistakes. If you're good, you're gonna learn from those mistakes and not make the same ones. I can't stress it enough. Even when I started in single family, I still had mentors that I still lean on to this day, and it's made that learning curve shrink and it made me feel comfortable to not make mistakes that they already made. And the other thing is don't be afraid to put yourself out there because I have learned this is an industry that plenty of people want to help you succeed. And in this space that we're talking about multifamily, most people will fail if they try to do it all themselves. Ask for help.

Brian Briscoe:

Yes. Yes. Ask for help partner, you know, look for people where there's a value proposition there. I think that's wise. All right. Last question how can listeners learn more about you?

Keith Heckman:

So my website is ktahproperties.com. You can learn about what we've got going on there. You can book a call if you want to have a conversation. Uh, then my email is ktah properties lc at gmail.com.

Brian Briscoe:

Awesome. Awesome. And we'll we'll make sure that information is in the show notes for anybody interested. That's it. Keith, thanks for coming on the show today. You provided a ton of value.

Keith Heckman:

Yeah, I appreciate your time, Brian. Thanks for asking me.

Brian Briscoe:

Hey, I hope you got a lot from today's conversation. Uh, if you did, make sure to subscribe so you don't miss future episodes. We're on all major podcast platforms and YouTube as well. Now, if you're ready to move from listening to actually doing, check out the Tribe of Titans multifamily investing community. That's where investors go deeper with live discussions, real time QA, and practical support around capital raising, finding deals, asset management, all of it. All right, you'll find everything you need at thetriboftitans.com. That link's in the show notes, tap it, and we'll see you there.

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