In this episode of That Real Estate Tech Guy, Jordan Samuel Fleming sits down with Caleb Christopher of Creative TC, DOS Guard, and Creative Title Company for a deep, practical conversation on creative finance and where it actually works in real-world investing.

Caleb breaks down subject-to deals in plain English, explains why creative finance is more about the seller’s story than the buy box, and shares real examples of how these strategies can help investors and homeowners win without cutting corners. The conversation also dives into why traditional title and underwriting models often struggle with creative deals, and how Caleb is building investor-friendly title solutions to close that gap.

You’ll also hear a forward-looking discussion on technology, AI, and automation in real estate, including how smarter systems will change investing, deal evaluation, and long-term investor relationships.

This episode is a must-listen for investors who want to understand creative finance the right way and use technology to scale ethically and intelligently.

About Caleb Christopher

Caleb Christopher is a builder — of businesses, of systems, and of people. Known for his ability to take complex problems and break them into practical, repeatable solutions, he has become a trusted voice in the real estate investor industry. His companies — Creative TC, DOS Guard, and Creative Title Company — are known for their practical application of deep expertise. At the center of the companies is Caleb’s personal vision: raising the standard in real estate by making it safe, legal, and ethical.

Caleb learned to stop jumping from idea to idea, and builds with purpose. His ventures aren’t side hustles — they’re infrastructure. Each company he launches fills a critical gap in real estate, whether that’s risk management, transaction clarity, or title operations. His background in cybersecurity gives him a mindset that values systems, risk management, and foresight, while his faith and family values ground him in stewardship, service, and truth.

As a podcast guest, Caleb is both a practitioner and a teacher. He has closed thousands of creative finance deals, built multiple remote-first companies, and managed international teams. He speaks candidly about successes and failures, weaving personal stories with actionable takeaways. Guests often comment that they got multiple golden nuggets after listening to Caleb.

Important Links

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• Creative TC
• smrtPhone – The only phone system built for real estate investors (5,000 free minutes)
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I can tell you one thing: technology is the single most important aspect of every business that has successfully scaled. It’s time for That Real Estate Tech Guy, your weekly chance to explore how technology can help your real estate business explode. Each week, you’ll hear from real estate investors who have been there and done that, and you’ll find out their favorite technology tips.

Listen in as Jordan speaks with tech companies and learns about new technologies and new ideas that will help you scale your business. And now, join your host, Jordan Samuel Fleming, CEO of SmrtPhone, for this week’s episode.

Hey, and welcome to this week’s episode of That Real Estate Tech Guy. I’m your host, Jordan Samuel Fleming, Chairman of SmrtPhone, the only phone system built for real estate investors, and author of Click, Call, Close: The Real Estate Investor’s Ultimate Phone System Playbook. Today’s episode is super fun, with Caleb Christopher from Creative TC, DOS Guard, and Creative Title Company.

This was a really interesting conversation. Caleb gave one of the most illustrative explanations of creative finance and where it’s applicable that I’ve ever heard. A lot of the time when people talk about it, you’re still left with questions. Caleb really zeroed in on where it works, why it works, and what it actually does.

We also got into the longer-term relationship side of these deals, because creative finance isn’t just a transaction. Caleb’s a guy with multiple businesses. Not only does he run Creative TC, which supports creative finance transactions, he’s also building creative finance-friendly title companies, because it really is a different kind of game.

We dive into why it’s different, and why some traditional underwriting and title company models don’t work as well here, mostly because they don’t understand it. This episode is both a great look into when you should start thinking about creative finance and why it’s applicable, and also how you can get started and scale using it.

I’m really grateful for Caleb coming on. I think we’re going to do a lot of things together, and I think you’re really going to enjoy this episode. So without any delay, let’s dive into my conversation with Caleb Christopher from Creative TC, DOS Guard, and Creative Title Company.

I’m here live with Caleb Christopher. Caleb, welcome to the podcast. It’s great to meet you. Why don’t you give everyone a sense of who you are and what you’re focused on?

Absolutely. Thank you. I live in a basement in Kansas, and I work remote jobs. I started a couple of companies to fill what wasn’t there for me when I got into real estate.

I built my niche around creative finance. The first company is Creative TC. We consult on creative finance deals: subject-to, seller finance, wraparound mortgages, really complex stuff. That’s where I like to live every day.

And as we grew, I saw a need for title companies that understood the complexity of investor transactions. We just finished raising $320,000 as a seed fund to start a title company in Colorado, and we’ll expand later.

That’s going to be interesting, because with so many investors I speak to, that’s definitely my customer base. The vast majority are wholesalers, flippers, that kind of thing. And I’ve always seen creative finance as a minority of the day-to-day conversations.

That’s one reason I had Chris Prefontaine on a while back. His coaching company is very focused on creative, and it’s great to keep bringing this to the foreground.

Can you give a little dive in? Why did you focus on creative finance? Let’s talk about that first, before we go into title. Why this? What does it do for you?

Creative finance scratches an itch for me, an intellectual itch. I like variety. In my IT background, every day brought something new.

Creative finance is the same way. You come to me and say, “Hey, I’ve got this seller in this situation. They’re in pre-foreclosure. Here are all the moving parts.” And I’m like, “Thank you. More variables. Please.” Let’s lay it all out. Everything cascades. If you do this, then seven things change. I love that stuff.

So creative finance scratches that itch for me.

Should I define “subject-to”? Okay. “Subject-to” is the primary way we do creative finance. There are lots of other ways and components, but a lot of times I’m buying your house and I’m taking over your payments. I get the deed, I make your payments, and your loan stays in place.

So if your neighbor has to sell, or they’re in pre-foreclosure, you might say, “How about I give you $10,000 and take over your payments?” I’m oversimplifying just to show how you even get into one of these deals.

But here’s the thing: every piece of real estate you’ve ever bought is “subject to” something. If the utility company comes and digs up your yard, can you do anything about it? Probably not, as long as they’re in their right-of-way or easement. You bought the property subject to an easement, or an HOA, or a city requirement, or whatever.

So every piece of real estate bought and sold today is subject to something. The only difference with creative finance is we add the mortgage to the list of things that the property is taken subject to.

So if the bank has a problem with it and wants to accelerate the loan, or whatever the loan terms allow, those can be applied against the house, and you really don’t have a claim against title insurance for that specific issue.

That’s “subject-to” in a box.

Can I ask something in that? As someone who doesn’t do these kinds of deals, I never have a good answer when people ask me this.

When I talk to traditional wholesalers and flippers, they’re looking for buy boxes: death, divorce, all the typical ones. Are the buy boxes the same for creative? Or is there something different you look for, something outside the typical investor box where you’d say, “Because of these circumstances, creative is a really good option”?

That’s a really good question and a great way to look at it.

What I always tell people is: cash, Realtor, keeping it. Rule out those three things before you go creative. Creative finance is weird. It’s not normal. So if there’s a cash offer that works, do that. If the MLS works, do that. If they can keep it, great.

Creative finance is an entanglement. You’re stuck with multiple people you may or may not want to be stuck with for a while.

So, cash first. If the MLS works, do that. If it didn’t sell, or they don’t like Realtors, or they can’t show it, or it won’t pass inspection, there are plenty of reasons, but you want to talk to the seller and find out why cash doesn’t work, why MLS doesn’t work, and why they don’t want to keep it.

If they can give you those reasons, you have a viable conversation for a creative finance deal.

It’s more about the story than it is about equity position. That’s top of the food chain. There’s a story behind every deal, or there’s not a deal.

After that, I’m looking at low equity or high equity. Those are the two big ones. Somewhere in the middle, there’s probably a cash offer that would work, and it’s hard to make up the difference when someone has, say, $100,000 of equity. They’re not going to take a $5,000 down payment and $80 a month.

If there’s an opportunity to treat the existing loan like a bridge loan, that can work: “Hey, I’m going to repair the property, make it premium, sell it for top dollar. I’ll make your payments in the meantime, pay you to move out, you give me the deed, and I’ll get it sold within six to eight months.”

I want to be careful with wording here, but in short, you can structure something where both sides benefit. The paperwork is much more specific than just saying, “We’ll split profits.” Don’t do that phrasing.

Let me ask a follow-up. Is this a good scenario where creative would work?

Scenario one: traditional situation, husband got sick, medical bills are mounting, they need cash and out. That seems like where a traditional cash offer is king, because they need to move quickly.

Scenario two: one where immediate cash isn’t as needed. What’s the kind of story you’d hear that points you toward creative?

A lot of times we see pre-foreclosure, where someone is behind on payments and they don’t have enough time to sell the house. They’re going to lose it at auction. If the house is worth this much, it’ll auction for this much. Period.

And if their equity is this much, they don’t get anything. If it sells for less than what’s owed, they might also get hit with a deficiency judgment. So they’re in a pretty bad situation.

Meanwhile I can say, “Listen, I’ll catch up your payments.” If they’re 18 months behind at $2,000 a month, that’s a lot of money to come out of pocket.

But zoom out: it’s basically the same thing as me giving you that money and you making the mortgage payment. You need to anchor that with sellers. Because when you say, “I’m giving you $4,000,” you’re not just giving them $4,000. You’re paying a big chunk to the mortgage company on their behalf, plus whatever they walk away with.

And then sellers ask, “Well, what if you don’t make the payments?” What incentive do I have not to make payments after I drop $40,000 plus repairs and holding costs? I’ve got skin in the game. If it goes to foreclosure, it hits their credit, and I lose the asset. I’m in the business of making money, renting properties, whatever the business model is.

You don’t need to be shady with people. That’s why I say disqualify cash, Realtor, and keeping it first. Now you’re working together on a solution.

Here’s what I can do for you. Here’s my incentive. Here’s your incentive. Your credit gets saved. A performing mortgage helps your credit. Payment history matters. Account age matters. The sooner we catch up and resume, the better.

I’ll tell you a story: I picked up a property in Pueblo, Colorado, at about a 3.65% interest rate.

They already tried cash and the MLS. It didn’t work. They had it listed and it expired. Keeping it didn’t work because they moved 45+ minutes away, had their first child, and had jobs not in the area. They didn’t want to be landlords. They didn’t want to fix toilets. I didn’t impose that; I had to get the story from them.

So I said, “If cash doesn’t work, the Realtor route failed, and keeping it doesn’t work, here’s what I can do. I can take over your payments and turn it into a rental.”

They had already bought another house and were making two payments. The deal didn’t cash flow. I showed them my spreadsheet. It loses about $200 a month, so it wasn’t a deal.

Here’s what made it a deal: they paid me $200 a month for two years to cover that gap so I could run it as a rental. They assigned a $6,000 insurance check to me for flooring repairs. They let me take over payments with zero out of pocket to them, and they paid me $200 a month for two years.

I didn’t take advantage of anybody. It simply wasn’t a deal otherwise. It still hasn’t netted me cash positive over the last two-plus years, but it’s a 3.65% interest rate with 27 years left. That becomes a great deal over time, and I was able to help people. That’s why I love creative finance.

Now, I’m sorry to interrupt this amazing conversation, but I wanted to make sure you knew that SmrtPhone, the only phone system built for real estate investors, connects to best-in-class real estate investor CRMs. And because it’s my show and I’m the co-founder and chairman of SmrtPhone, I’ve got some great deals for you.

Click the link and take advantage of 5,000 minutes of free calling with SmrtPhone, the only phone system built for real estate investors. Click, call, close more leads. Back to the show.

That’s fantastic.

I’m in a weird situation where I spend most of my days talking to real estate investment companies, but I’m not an investor myself. At some point, once I sell SmrtPhone, I’m going to have to become an investor, because at this point I’ve got contacts in every state.

But one thing I really like about what you’re saying is the win-win side. There’s a seedy side of investing, and there’s a good side. There are people who will do anything to get a deal across the line. And they’re the ones posing on Instagram with a Ferrari or a private plane they rented for the photo.

What resonates with me is that I’ve been in business for myself for 20 years. I like partnerships. I like building opportunities where I win and you win. I like building things up, not tearing things down. And I love that story, because it’s a win for everyone. Everyone gets what they wanted. No one goes home feeling taken advantage of. It may not be “I sold my house for X,” but it fits their needs and yours.

You illustrated that better than I’ve heard it illustrated in a long time.

Thank you. And that’s my real story, not a third-party story. I own that property. That’s me and those people.

They called me two years into the deal and asked, “When will this be off our credit?” And I said, “We talked about this. I bought the interest rate. It’s not even a deal for five years. That’s when I start cash flowing. Everything else is break-even. I’m currently negative, and that’s fine.”

If I bought an investment property with 20% down, 20% of $200,000 is $40,000. How long does it take to earn back $40,000 in rental income? So if I think of this as a financed down payment, I’m okay with it.

I’m currently about negative $37 a month after property management. My out-of-pocket over a two-year period, after rent and vacancies and everything, is less than $10,000. I’m okay with that, because I understood it coming into the deal.

But it’s still a low-equity deal.

How often do you get people down the line, because you’re essentially hopping into bed with people? This is more like a partnership than a transaction. A real estate transaction starts, ends, and you’re done. This is ongoing.

How often do you get those calls where their life has changed and they start questioning why they’re doing this?

It comes up consistently in subject-to deals.

To be clear, Creative TC helps other people get their deals done. I’ve done several myself, but my team helps 30 to 50 of these every month, so I see a lot.

I get calls six, 12, 18 months later: “Hey, my seller’s asking me X, Y, Z.” It’s pretty common.

Just like I dealt with my sellers: “When is our loan going to get paid off?” Well, I bought the rate. I told you it’s not a deal for five years. I’ll reiterate: as long as I can keep the rate, I will.

If you need to qualify for another loan, connect your lender to me. I’ll explain the situation. From an underwriting standpoint, it’s about debt-to-income and how they treat the obligation. I can speak to that.

The bigger point is: you have to manage people actively. That starts with setting expectations up front. You need good documents, good disclosures, and conversations about the “what ifs.”

I started my company to help make creative finance safe, legal, and ethical. That means people understand what they’re getting into. Good documentation. Good disclosures.

After closing, what happens? Am I actually taking care of you, or am I just taking the deal?

So yes, getting these calls is normal. And if you did it right in the beginning, it’s usually just a reminder: “Hey, remember what we set up. Remember you said you couldn’t do A, B, C, and D without this solution. Remember you were headed for foreclosure.”

If I didn’t bring this loan back into play, you’d have a foreclosure on your record for seven years. Now it’s only two years later and you’re qualifying again.

You do have to remind them of that.

Every once in a while you get someone who’s very difficult and they bring in an attorney. At that point it’s like, “Alright, if I have enough equity and I can get out of the situation by refinancing and getting back to break-even, it may be easier than dealing with a hostile seller.”

Let’s pivot to Creative TC, your company. I’m always trying to bring the SmrtPhone customer base resources that can help them. We’ve got about 2,500 real estate investors using us daily.

Tell me about Creative TC. How does it help the average investor who wants to do creative deals but doesn’t have the processes, documentation, or infrastructure?

I was you in the past. I built what wasn’t there for me.

Creative TC is consulting, with free 15-minute consults if you think you’ve got a creative deal. I’m here to raise the standard for safety across the industry.

So we offer free 15-minute walk-in appointments at Creative TC, because that’s not what was there for me, and I think it’s the right thing for the industry.

If you think you have a deal, if you’ve received an offer, if you’re an agent receiving subject-to offers, I can help you evaluate and understand them.

I have a trained team that works directly for me. I don’t use contractors.

Then there’s Creative Title Company, which we just launched. That’s Colorado-specific right now. But we can also help you understand liens and encumbrances.

I can pull an O&E report nationwide for about five bucks. I can host escrow-only services for private-sale transactions that don’t have title insurance.

I want to bring creative solutions to people’s real-life problems.

One thing I want to highlight about title: real estate is typically transactional, with a definite start and stop. Creative finance is not. When a title company does a creative finance closing, many treat it like: “You signed, I’m out.”

But I understand closing day is just the beginning of a long-term relationship. It’s a formalization of the relationship, and I’m there to help.

With the title company being Colorado right now, your plan is to expand. What’s your trajectory for expansion? I could imagine models like partnerships in different states, even franchise-like structures.

Title companies are part of the insurance industry. Insurance says no to risk. That’s their job.

A lot of people don’t realize title companies are insurance companies. They’re an agent for an insurance underwriter. So if they don’t understand something, it’s risky. Many title companies don’t understand creative finance, so they say no. That makes sense. It’s not their wheelhouse.

I’m trying to add capacity to the marketplace for these creative deals.

That said, I want to do all deals, not just creative. Bring everything to me.

My business model is to raise capital and be accountable to investors. As an entrepreneur, I’ll cheat on my own calendar if it’s just me. But when other people are relying on me, that calendar matters a lot more.

Part of me being a good business person is creating that back pressure: bringing in investors, casting a vision, and getting them behind me. I just got back from a conference trip, and I’m writing a trip report so people can see where their money’s going.

The model is: we start with the existing investors. We grow investor relationships. For the next six to 12 months, we focus on investors as customers. Then we expand to agents and lenders. We’re not turning that away, but our marketing focus is investors first.

And as I build investor relationships, investors will say, “I do three deals a month in Colorado, but ten in Missouri. Can you open there?” Sure, if we can do it right and it makes sense.

So expansion will be organic, based on opportunities and deal flow, as long as it justifies it. My mission is to capture 1.5% of the Colorado market, so I don’t want to go off mission. But if expansion adds revenue with the right licensing and process, great.

Let’s pivot again for a second. I was reviewing your site earlier and saw things like contract write-ups. We’re now living in a world of AI. I live and breathe it every day.

SmrtPhone is launching an AI agent marketplace inside SmrtPhone, where you’ll be able to hire inbound and outbound voice agents, call coaching, scoring, and more.

I’m working with a property management company to build a leasing agent and a maintenance request agent. The maintenance request agent is trained to understand escalation: plumbing, HVAC, seasonal issues, and it can create work orders via webhook. In version two, it’ll be able to call vendors and schedule jobs.

Where are you seeing AI fit into your world?

Title has some assisted title search tools. Mostly it’s assistive. Consulting is very dependent on situational context and ideas generated by the person.

We use AI to help with that. We suggest things. A lot of it is: “Here’s what I want to do, here are my factors, attack it, break it down, see if you can break it.” Then we build solutions. “How could I defend against this situation while the homeowner might claim A, B, and C?”

We also remind it: “I don’t want to be one-sided. I want it safe, legal, and ethical.” But I also want the most protection for my client.

In title, AI can assist with searches and generating a list of title clearance items.

Phone systems, too: order entry, intake, and things like that.

That sounds right.

I was on a webinar earlier today and they asked me to do a live demo of our voice agent. Live demos are always fun because you’re thinking, “Oh man.”

But I did it. I screen-shared, clicked to dial, called an inbound acquisitions agent. First ring, it answered. It asked why I’m thinking of selling. I said it’s a medical emergency and I need to raise cash. The agent responded with empathy and referenced it again at the end of the call.

The best part is it’s not a one-to-one script. It’s a trained agent, adjusting to the factors at hand.

Over the next six to 12 months, and 18 months, we’re going to see agents that take actions: making calls, answering calls, updating systems, creating documents. It’s a massive opportunity for almost every application, and I imagine creative finance will move fast too.

Yeah, gathering variables and suggesting options, if it becomes more than querying language models, it could do a big portion of what human consultants do.

I also love the idea of evolving CRM automations. They’re very linear right now: “If this, then that.” But if you add an AI evaluator component, it becomes: “Here’s what we’re trying to do, and here are the boundaries.” If the sentiment is this, pursue that line.

But you also need boundaries, because otherwise you get a supportive agent agreeing to crazy prices. It’s like when you use ChatGPT and it comes back with, “What a great idea,” and you’re like, “Tone it down.”

I don’t want toxic positivity. I’d rather you be adversarial than overly agreeable.

Totally. And the “agentic” experience is going to revolutionize everything. CRM integration won’t just be data entry. It’ll be: “Find my best leads right now. Who should I call today?”

And we’ve built memory into our agents so they can recall conversations from months ago. So you can have an agent that says, “Last time we spoke, you were going to talk to your sister. How did that go?” That’s a brave new world.

Some people hear that and think it’s scary. I can’t wait. It’s better systems. And it frees up the best people to do their best work.

Well, Caleb, I genuinely enjoyed meeting you, and I’m grateful you came on.

How do people find you? What’s the best way so I can drop it in the show notes and descriptions?

My favorite thing is: go get my monthly newsletter. I’m anti-guru.

When I have a lazy month, I show my real financials. I’ve got multiple businesses and four rental units. Sometimes two units are vacant, and I’ll post that. Why is it vacant? Because I was focused on other projects instead of pushing to fill them. That’s my fault. That’s real life.

I’m also anti-toxic positivity. People who only talk about the good and never the negatives, that’s not real.

So grab my newsletter. You’ll get my phone number and email. You can reach out directly. And you can see all the businesses I own and connect with them directly from there.

Awesome. It was a genuine pleasure and privilege to have you here. I learned something, and I also really enjoyed the challenge. Thank you so much for joining me.

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