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Solving Complex Seller Situations with Creative Strategies | Daniel Burke-Aguero Interview

By September 30, 2025Real Estate Pros Show

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Show Summary

In this episode of the Real Estate Pros podcast, Kristen interviews Daniel Burke-Aguero, founder of Trailhead Investment Group. Daniel shares his journey into real estate investing, emphasizing the importance of integrity and transparency in the industry. He discusses the unique challenges of navigating multiple markets and the innovative novation model that allows sellers to achieve better outcomes. The conversation highlights the company’s commitment to helping sellers in difficult situations while building a culture of honesty and support within the team.

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    Investor Fuel Show Transcript:

    Daniel Burke-Aguero (00:00)
    because it’s unregulated, because there’s a lot of bad actors, because there’s a lot of people who aren’t transparent in what they’re doing, well, what if we just operate with integrity, honesty, transparency? What if we just do the right thing for the right reasons? Man, what a cool opportunity to help a lot of people and to build something impactful.

    Kristen (01:54)
    Welcome back to the Real Estate Pros podcast. I’m Kristen and I’m here with Daniel Burke-Aguero, who’s the founder of Trailhead Investment Group. They are a nationwide real estate investing firm that solves complex seller solutions that don’t fit into the traditional retail sales model. So we’re going to get into a lot of great stuff here. Thank you for being here, Daniel.

    Daniel Burke-Aguero (02:12)
    Thank

    you. Thank you for having me.

    Kristen (02:14)
    Yeah, you’ve

    been able to scale Trailhead to a really impressive level in a short amount of time. So I’d love to kind of go back and talk about what got you into the real estate industry.

    Daniel Burke-Aguero (02:27)
    yeah. It’s been kind of a crazy journey, but if I can summarize it as simply as I can, I’ve done a lot of other things over the years. I’ve always been adjacent to the real estate space. So there’s a period of time where I’ve worked in mortgage, I’ve worked in business development, I’ve had the privilege of helping coach and pull apart businesses both in real estate and title and…

    I’ve always been around it. ⁓ And a little over two years ago an opportunity came around where

    first time I got to see inside of a virtual organization. So every group I’d ever worked with before, ⁓ I worked with some really big real estate teams, but they are always local to their backyard market. They were always the king of their hometown kind of thing. And as much as I love the idea of that, I live in Columbia, Missouri, and I love Columbia, Missouri, but it’s a town of 120,000 in the middle of the state. It’s a college town surrounded by cornfields.

    of

    a much smaller market footprint than the major cities, right? And so it had never really clicked for me to scale something like this, because I just didn’t think the opportunity was where I lived. So I got to see inside of a virtual organization and it really started shifting some things for me around not only the opportunity to build something virtual, but also seeing into the real estate investing space specifically and seeing an opportunity

    where

    because it’s unregulated, because there’s a lot of bad actors, because there’s a lot of people who aren’t transparent in what they’re doing, well, what if we just operate with integrity, honesty, transparency? What if we just do the right thing for the right reasons? Man, what a cool opportunity to help a lot of people and to build something

    ⁓ yeah, kind of fell into it, really. ⁓

    series of events but here we are and it’s been about a year and a half and we’re having a lot of fun. It’s been cool so far.

    Kristen (04:32)
    Yeah, I mean that’s a really

    good point. think that, you know, in real estate you do feel chained to your location and chained to the market that you live in. And I think that’s a really interesting point that you found a way to be, you know, national and not necessarily have to be, you know, the backyard expert like you said.

    Daniel Burke-Aguero (04:52)
    Yeah.

    Kristen (04:53)
    Yeah, so how did you even go about setting this up? And I imagine working nationally, it’s probably very challenging to navigate multiple markets at once.

    Daniel Burke-Aguero (05:52)
    I mean, yeah, there’s definitely, there are inherent challenges to going wide versus going deep. I was really lucky. ⁓ Part of me getting into this space, I had the privilege of working with a mentor of mine, Nick Perry. ⁓ Nick is pretty well known in the industry for the nationwide approach. And ⁓ he taught me so much. ⁓

    you know, some of the basics around just the marketing side and how to actually get in front of the opportunities. ⁓ But really, Nick is so good about teaching some of the frameworks on the system behind underwriting deals virtually, how to leverage ⁓ local people in all these different markets to provide feedback, to build a repeatable system. ⁓ And so yeah, once you really start assembling the team and assembling the pieces and figuring out

    Essentially the systems right it actually becomes pretty straightforward ⁓ We we look at a lot of deals. I think we get somewhere around 20 to 30 inbound leads a day the team Processes, I think this month we have 14 closing so it’s it’s moving in the right direction But of the 14, I think only two are in the state that I even live in Everything else is just all across the country and we’re moving a lot of pieces around but it’s it’s definitely it’s working

    So.

    Kristen (07:16)
    Yeah, yeah,

    and you’ve been able to hire some team members to, I’m sure that helps tremendously as you’re navigating all these leads. Yeah, amazing. And so tell us more about these seller situations that you help with with Trailhead.

    Daniel Burke-Aguero (07:32)
    Yeah,

    so I’m a big believer that if a seller is able to list their property on the market, if they’ve got the time, the flexibility, they’re probably gonna make more money than selling it to an investor like us. ⁓

    That’s just 99 % of situations. If you can list it, you probably should. But there’s a lot of people who reach out to us from our ads, from our campaigns, who are in situations. And that’s why they’re looking for a cash offer. Sometimes it’s the normal things. They inherited the property. They don’t know what to do with it. Maybe there’s a medical situation, or the bills are piling up, or something.

    There’s just a lot going on in their life and they’re just looking for simplicity. Sometimes they’re looking for speed. Sometimes they’re looking for just security of saying, I don’t want to deal with the unknowns and the hypotheticals of listing it myself. And so a lot of times when we dig into it, what we’re really looking for is, is the situation big enough?

    Kristen (08:36)
    Great.

    Daniel Burke-Aguero (08:44)
    that our solution and really the discount of their equity that we need to be able to perform, is the situation big enough that our solution actually makes sense or are they just better served by just listing? And if they are, we tell them that. say, listen, we’re just not the right fit. Here’s what you should do instead. We wish you the best of luck. ⁓

    But yeah, when there are situations that we can help people with, and I’m sure we can talk about some of those, it’s so cool to be able to get those texts from sellers and those calls and those emails of saying, hey, without you guys, wouldn’t have been able to do this. Like, thank you so much. I think that’s just, it’s so gratifying. It’s so cool.

    Kristen (09:28)
    Yeah.

    my god, yeah. I’m

    sure that’s one of the best parts of the job. Can you talk about, you know, maybe a specific example of that?

    Daniel Burke-Aguero (09:39)
    Yeah,

    yeah, so we were talking about this a little bit before. Our primary exit are what are called novations, right? So a lot of…

    sellers who reach out looking for a cash offer either it’s a true cash offer and the investors actually to buy it or it’s a wholesaler and they’re just going to flip the contract to another investor

    and again generally that’s that’s fine if that’s the only solution that’s fine but you really do have to be 70 75 percent of the ARV minus the expenses minus the assignments you really do have to be in a situation where you’re giving up a lot

    for that speed. ⁓

    A lot of the sellers that reach out to us, maybe their debt is too high or maybe they’re just unwilling to accept such a high discount or maybe they want to sell fast, but they don’t have to. Like they’re not pre-foreclosure. just, they just prefer speed. Right. So it’s not like the normal situation. So those are the sellers that we can, we can really, think, serve by doing innovation. So in innovation, what we are really doing is we’re

    replacing our A to B contract with a A to C contract. ⁓ At the core of it, we work with lot of sellers who have really decent houses, but again, something in their situation is preventing them from going the normal, just listing on their own route. So a good example of this, we were working with a seller in Kansas.

    ⁓ rural Kansas, I think this was in Clay Center. So it’s a town of like 4,000 people in middle of Kansas. And she was either one or two months behind on her mortgage. She had fallen into a really tough spot where she was unable to catch up. But the house was in pretty decent condition and ⁓

    we knew that if we did list it, we would be able to get it sold pretty quickly. So what we did was we structured an offer with the seller where we were actually able to step in, we covered some of those mortgage payments to bring it current, right? So we deployed some capital. We then were able to list it with time because again, now we’re not fighting the clock on the pre-foreclosure for it to be sold out from under her. We were able to list it. We were able to find a buyer who…

    was so excited about the house and ultimately since they were going to live in it they offered significantly more. ⁓

    then we would have been able to offer buying it ourselves. And so between the two of those, we were able to offer more than what we would have had to if we were buying it. The seller was able to have her solution. She avoided foreclosure. She got more money than she would have otherwise. We have a happy buyer moving into their new forever home. And in that process, the sewer line busted. So in that process, the sewer line busted, I think it was a 2000 or a $3,000 bill to get it

    reconnected and across the finish line. But that’s another situation where because we were involved, we were able to. But the seller, if she had tried to list by herself without getting caught up on her mortgage, she would have been dealing with that pressure from, I hope I can get this done before the bank takes it from me. And she also didn’t have the money. And so if that had happened, if the sewer line had busted mid transaction, no one would have been able to help her.

    and it probably would have been taken from her. And so again, it’s situations like that where I’m really grateful for the opportunity to find places where we can help, right? Again, where it’s like it just doesn’t fit the normal retail model of just listing it and dealing with all this stuff. ⁓

    Yeah, I mean, I can tell a lot of those, but it’s ⁓ really cool when we find the right people we can help. ⁓

    Kristen (14:18)
    Yeah.

    Absolutely, and how did you even kind of land on this model? Did you try other types of models before you landed on this one? Because I think it’s really unique in the win-win, you know, aspect of it.

    Daniel Burke-Aguero (14:34)
    Yeah, and again, I do think that ⁓ wholesale or the cash buyer route can still be a true win-win in specific situations. But again,

    What I saw from because again, we’re we’re still pretty new in this in this world, right? But when I first started I was just doing assignments. It was just me. building it out

    And it’s great. We’ve developed some really awesome long-term relationships with some of these investors and you know We’re able to help them and it’s cool but I kept running into what I felt like was this catch-22 spot where I Want to serve the seller and offer them as much as possible

    Because again for some of these sellers, this is the only thing they have left. This is it and Some of them are my parents age or like some of them are my age some of them have kids the same age as my kids and it just It breaks your heart to see people in these situations. So I want to help them as much as I can But then also on the inverse side if we’re assigning it or if we’re buying it as a cash buyer It’s just math. We have to be below a certain threshold. Otherwise

    it’s not a good, like the risk isn’t, it’s just not a good move. And so we start getting squeezed, I felt like from both ends, where I’m trying to serve the seller and offer them as much as possible. I’m also trying to get a good deal for my buyers, right, or my investors. And also, I’ve got to make some money in the middle, because otherwise the money that we’re spending on marketing, if we don’t have a certain amount coming back to the company, we’re going to go under.

    And so I felt like we kept getting squeezed in that process. ⁓ I was introduced to the model of Novations. There’s some other mentors and it just really clicked where I said, man, there’s for sure situations where a cash offer is the best solution, hands down. But eight out of 10 of these ones that we get in our ecosystem, our inbound leads, they’re just not best served by a cash offer.

    And if we can serve them, offer more, we actually technically make more as well. Why not? And it’s a little longer, it’s a little more complex, there’s more stuff to deal with. But at the end of the day, if we can systemize that process, even though it’s a little more complex, ⁓ it’s awesome. So that’s what we’re working on right now.

    Kristen (17:48)
    Yeah, I mean

    that’s amazing and what really stands out to me is, you know, the priorities of transparency, communication, honesty. I’m sure a lot of people really appreciate that and you probably lose some business but what you gain is a lot more, yeah.

    Daniel Burke-Aguero (18:03)
    sure. Yeah,

    yeah for sure and I mean I think that comes back to what we were talking about earlier about ⁓ some of the challenges right now is is that there’s a lot of people starting to do novations who hadn’t before.

    And whether it’s intentional duplicity or if it’s just they just don’t know what they’re doing or they haven’t learned the right way to do it. ⁓ Some of our biggest challenge right now is that we’re talking to sellers who are getting what they think are true cash offers higher than where an actual cash offer can be. And what we’re navigating is we’re super blunt. We’ll say, listen, if I have to buy this, I’m here. But if we can work together on this,

    and you give us time, essentially allow us to novate it instead of buying it, I can offer you this much, right? And offer you more. ⁓

    But the challenge is that the seller isn’t getting the same level of transparency from everybody. And so they’re getting these offers from other companies where they think they’re getting a true cash offer that the person on the other end of the phone is actually going to buy the property. And it’s this really interesting space we’re in right now where

    You we do lose business because we are so transparent and we’re saying that’s not real. There’s literally no way an investor could offer 85 % of the value of your property. There’s literally no way for them to do that. The only way this works is by bringing in a retail buyer. Did they tell you they were going to list it? And they’re like, no, and all this stuff. But ⁓ ultimately, I think, like you said, you do the right thing for the right reasons and it all works out.

    Kristen (19:50)
    Yeah. And

    as you’re building out your team and hiring more people, how do you reinforce that culture in the company? And how do you make sure that keeps running through?

    Daniel Burke-Aguero (20:02)
    I think part of that, we’ve got seven team members right now. We’re gonna hire our eighth tomorrow. I think part of it is just in trying to hire slow, fire, fast, maybe is the best way I’ve learned this over the years, is I’m…

    I try to be hyper vigilant of the culture that we’re building of the right people for the right reasons who prioritize doing the right thing. And I think it is. It’s also just telling stories of all these different situations. Actually, here’s an example of that. The one I was talking about earlier in Kansas, the example story we were talking about before, the seller was going to make, I forget how much, a certain amount. We were going to make a certain amount.

    making a little bit more than she was gonna make at the end of the day. ⁓ because of the timing of things, at the closing table, she was set to make, it was like three or four grand less than what she thought she was gonna make. Because at the very last minute, the mortgage company threw in some fees and stuff like that, right? We were making enough on that deal that…

    It was just the right thing to do to reduce our fee and give it to her. Not like a lot, but we’ve reduced the difference from where the mortgage company just randomly threw on some fees at the last minute. Because at the end of the day, like I’m not the one losing my house. I’m not the one having to start over. I’m not the one stuck in this terrible situation that yes, now I’m out of, but now I have to rebuild from like every dollar matter.

    to us as a company and just to who much is given, much can be asked or however you want to phrase it, right? Like we have the opportunity to help people in a really big way that no one else can. And again, it’s exciting. And so again, talking about that kind of stuff because there are other companies that I know, people that I’ve met with, people I’ve learned from who think the exact opposite. And they would say, hey, we’re three days out from the closing table. ⁓

    as part of our standard process, we’re gonna do a reduction call because we wanna make an extra five grand because they have no other option because we’re right here at the finish line. So turn the knife for as much as he can, squeeze it for as much juice as he can. I just disagree with that approach.

    Kristen (22:39)
    Yeah,

    absolutely. Well, it definitely sets you guys apart. I mean, you’ve shared so much good stuff today about building your business and how you guys are different in the market and how you’re building with integrity, which is so awesome. Tell people how to find you and where to find Trailhead.

    Daniel Burke-Aguero (22:56)
    Yeah, on the internet. I’m Daniel Burke-Aguero. There’s only one of me. If you Google me, you will find me. It’s not the most common name, Instagram, Facebook, our website, all that. can send me a text, send me email, send me a DM. I actually respond, so.

    Kristen (23:15)
    Well, I really encourage everyone to check out Daniel and thank you so much for being here today. Awesome. And thank you everybody for listening. Hope you learned a lot, got some inspiration and we’ll see you back next time. Bye.

    Daniel Burke-Aguero (23:21)
    Yeah, thank you for having me. Appreciate it.

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