40 Private Lenders in One Room – The Golden Nuggets That Will Transform Your Lending Business (Charleston Mastermind Recap)

Travel, Connection & Mastermind Format

These might be some of my favorite podcast episodes because I get to share everything I learned at the HMB Mastermind I attended in Charleston last week. It was like drinking from a fire hydrant—complete information overload in the private lending space. They put you in a room with 40 or 50 other private lenders, and everyone gets a chance to talk and share. It’s powerful. I was trying to grasp all the insights and tidbits of wisdom. It’s definitely overwhelming.

So, to back up a bit—I first went to the HMB Mastermind in Tampa six months ago, in November. That event was incredible. I couldn’t wait to go back. They host these every six months or so, and being in a room with such driven, like-minded people is seriously energizing.

Traveling to this one, though, was a bit tricky. As you may know from past episodes, my wife and I recently moved to Arizona from Idaho. We don’t have family or babysitters nearby. So, when both of us travel, it’s a bit of a juggling act.

A good friend of mine was celebrating his birthday with a Vegas trip. My wife wanted to come, and of course, things are always more fun with your spouse. But again—no babysitters. So here’s what we did: she booked a one-way flight from Arizona to Idaho to drop the kids off with her parents. Then she flew from Idaho to Vegas. I flew directly from Arizona to Vegas.

We spent about three or four days in Vegas, just relaxing—caught a couple shows, hung out, had fun. I was even up $1,200 in blackjack, so no complaints there! After that, I flew straight from Vegas to Charleston for the mastermind. The only issue was weather delays. There were connection problems, so I got rerouted to D.C. and had to spend the night.

Eventually, I made it to Charleston, but travel takes a toll on me. I’m not sure if it’s the pressure or just the motion, but I prefer arriving a day early to settle in, shake off the travel fog, and get centered. This time, I felt a bit frazzled when I arrived. Not ideal.

This time around, my business partner Quin came to the event too, which was awesome. It was great for him to meet everyone and experience the vibe firsthand.

The first night, there’s typically a happy hour at a rooftop bar right across from the hotel. Some people arrive late and miss it, but most are there. It’s a relaxed setting—good food, drinks, conversation. It’s less about lending and more about connection. Just getting to know people, rubbing shoulders, and building camaraderie.

It was cool reconnecting with people I’d met in Tampa and introducing them to Quin. Then, on Wednesday, things officially kicked off—9 a.m. to 5 p.m., straight content. Both Wednesday and Thursday are jam-packed.

Each mastermind member gets a ~30-minute time slot to talk about their business. Most follow the “Brag, Share, Ask” format. The people in that room are doing some amazing things. Some come from construction, others from investment banking or totally unrelated industries before private lending. They’re shaping their businesses in such unique ways.

Most follow the “Brag, Share, Ask” format. The people in that room are doing some amazing things.

During the brag portion, you talk about recent wins or innovations in your business. Then comes the share, where you can discuss what’s working, a great software, or something that’s helped improve efficiency. Finally, the ask—your chance to get advice or input from the group.

At my first mastermind, I asked about software frustrations. This time, I didn’t have much of an ask. Honestly, most of my questions were answered in the first day and a half. By day two, a lot of the key topics have already been covered. That’s usually when interaction slows down a bit—people are more tired, and the big ideas are already out there.

Still, the first day was phenomenal. I didn’t present until Thursday, which I’ll talk about later. On Friday, most attendees head home. There’s usually a golf day, too, if you’re into that. I enjoy it, even though I’m not great.

This time, though, golf didn’t happen. There were weather issues and scheduling problems. It was frustrating, especially since I hauled my clubs from Arizona to Vegas, to D.C., to Charleston, and then back—without playing a single round. But hey, it is what it is.

Metrics, Insurance & Risk Mitigation

The format of this mastermind is what makes it so special. It’s not a conference. There’s no selling. No one’s talking down to you. No one’s positioning themselves as the “expert.” It’s just pure collaboration. The entire goal is to learn, grow, and share openly.

I took tons of notes—organized by speaker—and want to share the ones that stood out the most. The first major one came from Chris Davis of Approach Lending. He’s incredible. What stood out the most was how deeply he tracks his data. He’s a master of metrics.

For instance, he breaks down loan duration by quarter, tracks credit score by borrower, and even compares credit score to loan payoff behavior. He also tracks estimated vs. actual LTV and ARLTV—from origination to payoff. That level of detail blew my mind.

Chris even monitors whether borrowers consistently over- or under-estimate their numbers. I’d never thought about that before. Most of my borrowers are overly optimistic—they want more leverage and higher loan amounts. But tracking whether someone consistently overestimates could be a huge risk indicator.

Say you’ve got a borrower like John Smith, and he’s always 10% off. You can start adjusting your expectations and risk models accordingly. That insight alone is incredibly valuable.

… a borrower like John Smith, and he’s always 10% off. You can start adjusting your expectations and risk models accordingly.

Of course, external factors matter—like market conditions. A conservative borrower might still miss timelines if the market shifts. But even with variables, Chris’s tracking offers huge advantages.

He also monitors appraised value vs. final payoff, which is smart. There’s not always full control over that due to appraisers and fluctuations, but it’s still useful data.

Lastly, and this one wasn’t directly from Chris, but it came up during his presentation—someone said there’s a direct correlation between credit score and aggravation index.

And I loved that.

It’s so true. Borrowers with higher credit scores tend to be far less of a headache than those with 550s or 600s. That comment stuck with me.

So yeah—Chris Davis was a highlight.

The next insight came from a presentation by David and Jeremy, who are based in Texas and represent Crown Capital. They brought up several new ideas I hadn’t encountered before. One topic—new construction loans—was especially compelling. But I’m going to save that for a future episode because I have a lot more thoughts to organize around it.

The other major topic they addressed was insurance and data protection. When we talked about errors and omissions insurance, Jason and Chris mentioned paying around $20,000 a year. That number shocked me. First, because I don’t currently carry that kind of insurance. And second, because they admitted they aren’t confident the policy would even pay out if they ever had to file a claim.

…errors and omissions insurance, Jason and Chris mentioned paying around $20,000 a year. That number shocked me.

That brought up a quote I once heard—probably butchering it here—but the idea was this: the likelihood of an insurance policy paying out is inversely related to its premium. Take life insurance, for example. You can pay $20/month for a $500,000 policy. That’s not protection—that’s just math. These companies are calculating statistical probabilities and pricing accordingly.

Same goes for renter’s insurance, which can cost less than a pizza. You might get a $30,000 policy for $15/month—because it rarely pays out. That kind of realization really opened my eyes. I’ve now made it a priority to dive deeper into insurance structures, understand premium logic, and assess what’s truly covered in order to improve my business.

We also covered cybersecurity and wire fraud prevention. One tool mentioned was Funding Shield, a wire verification service. I’d never thought about using something like that, mainly because we already verify every wire transfer by calling the title company or attorney directly. Still, it’s not a foolproof system. Someone could create a fake title company, after all.

Funding Shield might come with a guarantee or insurance in case of error, which is something I’ll be researching more. I don’t have all the details yet, but it’s definitely on my radar now.

Another big topic was background checks for employees. It struck me because I hadn’t considered doing them internally. We always run checks on borrowers—looking for felonies or serious misdemeanors—but rarely on team members. Most of our hires are people we already know well. But folks at the mastermind emphasized: you just never know.

They also said you should update those background checks annually. Someone may pass your screening when hired, but two years later, their record could look very different. Some lenders even make job offers contingent on clean results.

That segued into the idea of pulling credit checks on employees—another thing I hadn’t thought about. I wasn’t too concerned since none of my team handles bank access or money, but even so, the risk is still there. The general idea was to elevate your screening processes—whether borrower or employee—and I totally agree.

The general idea was to elevate your screening processes—whether borrower or employee.

There was also a topic I didn’t fully grasp but still found interesting. If you have an IRA inside of a fund, and you then take leveraged debt, it might trigger something called UBTI (Unrelated Business Taxable Income). I’d never heard of it before. A possible workaround was creating a sub-REIT structure, though it costs about $45,000 to $50,000 to set up.

Most of my podcast listeners don’t operate a fund, so this might not apply. In fact, I’d say around 80% of the people I work with follow a co-lending trustee model. But for those running a fund or considering one, this kind of niche financial detail is absolutely worth exploring.

They also talked about the Qualified Business Income Deduction (QBID). You need to meet certain criteria to qualify and receive those benefits. I don’t know a lot about it yet, but it’s another item on my list to dig into.

Alongside that, they introduced the 5/50 Rule. Essentially, it states that no more than five relationships can make up more than 50% of your fund. Again, something I’d never heard before. These are the kinds of small but critical insights that make the mastermind so incredibly valuable.

… the 5/50 Rule. Essentially, it states that no more than five relationships can make up more than 50% of your fund.

Only people who are deep in the trenches, managing active funds, would even think to bring this up. I would’ve never found this information on my own.

Another topic David and Jeremy covered was force-placed insurance. When a borrower’s policy lapses and they don’t renew, you’re forced to step in. Traditionally, we’ve either secured our own replacement policy or paid their existing provider to keep coverage in place—then charged the borrower.

We also tack on a service fee, because it’s a hassle and something we shouldn’t have to do. Chris and Jason recommended a service called mortgagehazard.com, which I’m definitely checking out.

Here’s what’s cool: if you only need coverage for 15 days, you only pay for 15 days. Most other policies are six-month or annual plans. With this one, it’s flexible, and you only get charged for what you use. It’s slick. I’m absolutely signing up, just in case we encounter lapsed coverage again.

They also shared a simple yet effective script they use with borrowers. When someone refuses to update their insurance, they just say: “Hey, this forced coverage is more expensive, and we charge you a fee for managing it. So you’re going to pay more unless you get your own policy reinstated.”

It’s such a straightforward message: Do you want to pay more or pay less? If less, get your insurance in place. I loved that. Super clean and direct.

AI, Local Networking & Online Visibility

Okay, last thing I’ll share in this episode—because honestly, there’s so much more and I don’t want this to turn into a 90-minute deep dive. These were just the main takeaways that stood out the most.

The last thing I’ll share came from a good friend of mine, Daniel Paloscio, who’s based in Florida. He talked about a service he’s piloting called Nova Echo. It’s a conversational AI company focused on handling outbound cold calls entirely through AI.

Daniel mentioned he had tested multiple products, and this one felt the most human-like. It didn’t come across as robotic. There were natural pauses, authentic speech patterns—it just sounded real. He said it’s not perfect yet, but it’s getting close. Within the next year or two, he believes it’ll be very solid.

He plans to use it both for inbound calls to his private lending company and outbound lead qualification. What really stood out was the live transfer feature. If a call hits a certain qualification point, it can automatically send the lead to a real person. But if the lead isn’t qualified? Let the AI handle it and save your team’s time.

Right now, our business doesn’t deal with a huge volume of inbound or outbound phone leads, so we’re not quite there yet. But as we grow, this is absolutely something I want to implement. It was still incredibly insightful regardless.

Daniel also shared something called the City BNI Association. I don’t remember what the “I” stands for, but basically, it’s a local business networking group with an approved vendor list. So, you might have a go-to plumber, electrician, handyman—and you can position yourself as the default mortgage lender in that network.

He paid a couple hundred bucks per year, plus some monthly dues, and said it’s been very cost-effective. The catch is, you have to attend meetings—usually once a quarter—to represent your business. That helps maintain visibility and credibility in the group.

For us, that’s a bit tricky. We lend in Idaho but live in Arizona, so I wouldn’t be able to make those in-person meetings. But for most listeners, especially if you’re local to your lending area, this is a low-cost, high-exposure strategy. And being listed as the go-to lender on a popular business site can drive a ton of leads.

… being listed as the go-to lender on a popular business site can drive a ton of leads.

One more highlight—there was a guy named Shane at the event. Much of what he said was way over my head, but he shared deep knowledge about local SEO, Google Search Console, and pay-per-click (PPC) optimization.

He talked about getting into the Google Map Pack, optimizing ads, improving your online presence, and how all of this ties into generating more leads. It was technical, but I definitely want to bring him on the podcast at some point. He could explain common mistakes people make and how to correctly run ads and boost online visibility.

Social Media Capital Raising & Wrap-Up

Finally, we gave our own presentation about halfway through the second day. I didn’t feel like I had a ton of groundbreaking stuff to share, but I did go over how we’ve successfully raised capital using social media. I think it was valuable for the group. A lot of people still aren’t tapping into that channel, even though it’s been our secret weapon.

People assume it’s hard, time-consuming, or super complex. But I’ve built out systems and workflows that make it pretty manageable—20 to 30 minutes a day, max.

That deserves its own episode. So I’m planning to go deep on that next week. I’ll walk through the full slide deck I shared at the mastermind and break it all down. It’ll likely be a longer episode—maybe closer to an hour—because I want to include all the granular details.

Overall, this event was unbelievable. Every single time I go, I walk away blown away. I learn so much more than I expected. There’s another one in six months, and I’ll be there—no question.

I don’t know where it’ll be yet, but you better believe I’ll do another recap episode when the time comes.

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