When most people think about real estate investing, they picture owning rentals or flipping houses.

Very few realize there’s another lane where you don’t swing a hammer, you don’t manage tenants, and in many cases, you never even see the property.

That lane is private lending.

In this Private Lender Interview Series, I sit down with real people who have put their own capital to work as private lenders. We talk about how they got started, what they were scared of, what’s gone right, what almost went wrong, and the lessons they’d give someone who’s just now hearing about this world.

In this conversation, I’m interviewing Tom, a longtime real estate investor who’s quietly done 20+ private loans over the years, several of them with my team.

We get into:

• Why it took him years of due diligence before wiring his first $100K+
• The simple risk controls he uses (like lending at 75–80% of purchase and requiring skin in the game)
• How mentorship, legal docs, and “trust but verify” have kept his portfolio out of trouble
• Why he believes one bad early deal might have scared him out of private lending altogether

If you’re curious about private lending but also cautious that’s a good thing. This interview will give you a real-world look at how someone else navigated those same questions and fears.

Private Lender Interview with Tom

(Lightly edited for clarity and flow.)

Brant:
All right, my friends, we are live. Hey, everybody. I’m here for another video in our Private Lender Interview Series, where I bring on a private lender so they can share their experiences and what they’ve learned through their private lending journey.

So without further ado, I’d like to introduce everyone here to Tom. Tom, how you doing?

Tom:
Doing great, Brant. Thank you.

Brant:
Great. Thank you for taking the time to come on and share your insights. We’ll just get right into this thing.

Tell everyone a little bit about yourself and what led you to private lending. How did you hear about it? Where did all this come from? Because truth be told, a lot of people don’t even know about this. So I’m curious for you to share how you learned about this opportunity.

Tom:
So I got into the rental business probably… I think my oldest daughter was five, so over 20 years ago. I had some rental properties.

Fast forward a few years, I played in this charity golf event for several years, and one of the main sponsors was Lifestyles.

So Lifestyles had other sponsors and, of course, if anybody’s familiar with golf tournaments, at every hole there’s usually a sponsor that’s doing something. At a number of those holes there were hard money lenders. And they’d say, “Hey, are you in the rental business?” And I was at the time.

They said, “Yeah, you know, if you ever need money…” and that’s how I found out about hard money lending—what they charged and whatnot. I was thinking to myself, because my rental properties were, other than my house (which I ended up renting). I paid cash for them. I didn’t need any lending.

But I listened to them and I was like, “I can’t figure out how somebody could pay three points and 12%,” you know, because I could have never made a profit doing that on the properties that I owned.

So I kind of learned about it that way. Then I found out about the private side. Then I started going to events—one of which you and Jason used to sponsor back in the day. Y’all would have those events, and there were events all over town. Slowly, I learned about it and certainly didn’t jump in overnight.

Brant:
Yeah, that’s how we met—at that event. Jason and I only did that once or twice. We only did that a couple of times.

Tom:
I was at both of them, then. It seemed like y’all did a few more, and then you did some on your own.

Brant:
We did a big one. Then we did one or two at Quest.

For people watching this—Lifestyles is a very large and local real estate investment club called Lifestyles Unlimited. Someone remarked one time, “That sounds like a swinger club.” I’m like, “No, it’s not.” It’s about creating the lifestyle that you desire through real estate. Just to clarify that because it does sound like “Lifestyles”—like, “What’s this all about?”

Anyway… so you were in real estate, and I would say that’s a good portion of the lenders I work with: they have a real estate background of some sort. They learn about real estate investing, then they learn about private lending.

And then some people are just clueless to the world of hard money. Hard money lending is a foreign term to them. They don’t know about these things that we do.

So that brings us up to: you’re in the business a little bit, investing, and then you learned about private lending.

Tell them a little bit more about what intrigued you, and what steps you took when you said, “Hey, I’m interested in this. I want to go down that path.” Because it’s a little bit scary: “Hey, I’m going to wire this person 100, 200, 300 thousand dollars.” It’s a little bit scary.

Tell them what you did to kind of overcome that fear you had.

Tom:
One of the people that would also attend this golf event with me—a longtime friend of mine—he was going to Lifestyles and ended up meeting somebody that you actually mentored.

His name was Allan. So Allan said, “Hey, you need to meet this guy Chris, because he’s looking at getting into fixing and flipping.” He put me and Chris together, and that’s where it all started.

Again, it had been probably two years of me doing some due diligence and thinking about it. Allan made the move first. He dipped his toes in the water and told me about his experience, and then I jumped in.

Brant:
Okay. And did you meet with an attorney? Did you have a call with anybody to figure out, “What are the requirements here? What do I need to have?”

Tom:
Allan was instrumental in getting me going with the legal information and all the documents and whatnot. Then, of course, we used a title company and moved forward.

On the first deal, they fixed it and flipped it, and then right after that we got into another one.

Brant:
Okay. So that’s really important information, because essentially you had a mentor, right? You had someone looking over your shoulder who had done it before.

If I was going to throw out one piece of advice—like, “What’s the most important thing for people that are new, just getting started?”—it’s this:

Don’t go at this on your own.

You need somebody looking over your shoulder, whether it be an attorney, whether it be someone who’s done it before—ideally both. Make sure you have someone in your corner looking over your stuff.

I do consulting for private lenders getting started, so we’ve got some ways to help you out with that—just to look over things. You don’t want to go about this alone in the beginning, especially if you don’t have a real estate background.

That’s where I’ve seen and heard some horror stories come from. They were with an investor they maybe didn’t know so well—or even if they did, that person was not looking out for their best interest. They didn’t know how to safeguard their interest.

So, approximately, Tom—if you don’t mind sharing—how many deals have you done over the years, just ballpark?

Tom:
Well, I’ve done five, I think, with you. Over 20 for sure.

Brant:
You’ve done more than five with us, haven’t you?

Tom:
Five or six.

Brant:
Okay. It took a while for us to do a deal together. Have you ever had any go bad?

Tom:
No. No. Thank goodness. Knock on wood.

Brant:
It does happen. I have. Some of my loans have had issues.

So what do you look for? Because there are two main things: you’ve got to qualify the borrower and qualify the deal. I say “qualify the dude, qualify the deal.”

What are a couple of things that you look for when you’re looking at a loan?

Tom:
Again, starting out, we were dealing with people that were essentially total strangers. So you kind of get to know them a little bit, and once we did jump in, we watched the results of their work—how they were flipping and whatnot.

Another thing we did: we didn’t loan at 100%. I know a lot of people want to borrow 100%, but we did not loan that. We loaned closer to 75–80% of the purchase value, so they had to have skin in the game.

Initially, we would not loan for any of the rehab portion either. We wanted them to bring that money out of pocket or perhaps get a second—although we preferred the first option, which was them coming out of pocket.

So again, more skin. Every day, it’s less risk and more comfort that this deal was not going to go bad. Because if one of our early deals had gone bad, I wouldn’t be sitting here talking to you today. We would have gotten out and said, “No, this is not for us.”

But because the people we dealt with were honest and did everything they said they were going to do, and we did everything we said we were going to do, we just formed partnerships. And like I said, the repeat business with some of these people is what we like, because we’re like, “Okay, we already know these people. We already know their tendencies. We know how they work. We see the results of their rehabs,” and so on. So it was more comfort built over the course of the years.

Some of these people got out of the business, and then you have to start with someone new and kind of start over. And then some of those people decide, “This is not for me. I’m not going to do fix and flips anymore.” So you do some one-offs, unfortunately.

Brant:
Yeah, I think this is really good advice and wisdom.

I would say a lot of lenders, even when they have a good relationship and have been working with a particular borrower for a long period of time, you never want to get too comfortable.

I met with a guy yesterday. He was telling me he was doing deals with so-and-so, who had proven himself and had a track record—and then sometimes people get a little too comfortable, which I think is human nature.

But I will say, Tom, you’ve done a good job with this. You’ll typically always call me and ask a question:

“Hey, what about this? What about that?”

We’ve done a few deals that weren’t cookie-cutter, and you pick up the phone, you call, you ask, you clarify. I don’t think a lot of lenders do that once they get comfortable. A lot of mine don’t—my lenders don’t call and ask questions where, if I was the lender, I’d probably want to clarify that. I know what’s going on, but they don’t.

And I think a lot of them just trust me—which I appreciate—but trust, but verify. And I think you do a good job of that, for sure.

Anything else? If somebody’s just reading the book or maybe they clicked on something and they’re like, “I think I’m interested in that,” how would you direct them on their next steps to figure out if it’s right for them or not?

Tom:
Well, I kind of laugh. There’s another person that just got into the private lending portion. There’s another guy that we both know—I don’t want to use names—but I asked the guy that was lending, “Hey, you’re doing business with so-and-so?” He goes, “Yeah.”

I said, “So how’s it worked out?”

He goes, “Well, I got what he said he was going to give me.”

I’m like, “Okay… so were you in first lien position?”

He had no clue. He had no clue if he was in first lien position. And that just struck me as like, “Wow.” He just trusted this guy. And again, it worked out for him—but you’ve got to make sure you have all the right documents, and you’re in the position that you want to be in.

Brant:
Yeah. Yeah.

It’s a difficult time in real estate. There are some people I know and look up to who are struggling. So you just have to be careful. You’ve got to verify things.

Typically, my lenders who’ve worked with me—when they do it the right way—they love it and they keep coming back and back and back. You do it the wrong way, with the wrong borrower, the wrong deal, then it’s not a good investment. That’s the same with everything in life, really.

So just safeguard yourself.

I’ve laid it out pretty well in the Private Lender Playbook—giving you checklists, ways to analyze deals and borrowers, safeguard yourself, like Tom mentioned about being in first lien position, all those types of things.

I appreciate y’all watching this and taking the time. If you have any other questions, feel free to reach out and contact me.

Tom, thank you for coming on and sharing.

Tom:
Absolutely. Loved this, and I appreciate it. I’m sure people watching this will get a lot of value from it as well.

Brant:
I appreciate it. All right—have a great weekend.

Tom:
Thank you.

Brant:
Yep. Likewise. Take care.

 

All the best, 
Brant