• Brett Calhoun

Interview with ClosingCostHelp Co-Founder & CEO

If you are an investor and want to learn more about the Scale portfolio companies, please reach out to Brett Calhoun at or shoot a DM on Twitter @brettcalhounn.

We are officially halfway through the first Scale cohort, with Demo Day around the corner in early January. Also, prior to this week, we have publicly released Friday drops on 4 of our 8 cohort companies (CapGains, Erly, Design with FRANK, and Goodhouse). For the second week in a row, we dig into another Missouri-based company, ClosingCostHelp.

What is ClosingCostHelp?

ClosingCostHelp offers creative financing solutions that align with the needs of all stakeholders within the home-owning value chain. The Company accelerates the home buying experience and access to liquidity. Starting with ClosingCostHelp, the Company is creating more Veteran homeowners and helping set up our nation’s heroes for long-term financial success.

The Problem

TLDR: VA loans were created to offer 100% financing to veterans to lower the barrier to becoming a homeowner. Although the mortgage is 100% financed the closing costs are not, which are typically 3–6% of the mortgage. Today, the average VA mortgage is $300k+, meaning closing costs on average would be $9k to $18k. That means 70% of Americans can’t afford closing costs or would completely deplete their savings to do so. In the current competitive market, sellers aren’t paying closing costs (veterans are less competitive buyers) and it is expensive to ask for a lender credit to pay for closing costs.

The Team

ClosingCostHelp was founded by folks who have experienced first-hand the barrier veterans face with closing on a VA loan (Josh Kaplan, Brett Calhoun, Jake Vehige). The team is on a mission to lower the barriers to homeownership, increase wealth for the veteran community, and create a better home buying experience for all stakeholders. More information on the team is below:

Verbatim transcript of the interview below:

Brett Calhoun: Good morning, Josh. Thanks for joining me on this fifth Friday Drop. This is a company that’s definitely near and dear to my heart because I was actually involved in this before, prior to scale.

Just so everybody knows, it’s watching this video. My name is Brett Calhoun. I am a director at scale and I run operations, portfolio management, and I am part of the investment committee. And I’m here with Josh Kaplan.

Josh Kaplan: My name is Josh. I am the CEO and one of the co-founders along with Brett of ClosingCostHelp, a new FinTech company in the market.

Brett Calhoun: Yep and so this is definitely something I’ve been a part of for about 12 months now. And we’re very excited about the mission of this company and how we’re actually helping put veterans into homes. Josh has a very interesting story, just kind of his way into entrepreneurship and some of the different things he started.

He’s seen some of the entrepreneurial struggle himself as an entrepreneur and as an entrepreneur in the Midwest and so Josh would just love to kind of dig into really, just learn a little bit more about yourself and tell us your journey as an entrepreneur and becoming the founder of ClosingCostHelp.

Josh Kaplan: I mean, I’ve always enjoyed problem-solving, always been a hard worker. I got my first official job when I was in third grade working for the Tribune and delivering papers, but I’ve always had side hustles and kind of enjoyed starting businesses as well. I remember in elementary school, we went to this thing called it was a field trip called exchange city, and everyone got to set up businesses and people had fake money and you just tried to create like a profitable business.

And that was in like fourth grade, I think. I just thought that was really cool and so I always worked since I started that job in third grade, had a job at McDonald’s when I was 15, they the only hire somebody as young as me, and then over the years, I’ve tried to start companies.

So before ClosingCostHelp, I had started a couple of other companies that didn’t really pan out. One we thought there was a large need for, but never really tested the market before going to market.

So the need wasn’t thought the second business is actually becoming more and more profitable month after month, but. Founders had a falling out. So we ended up just scrapping that. And the third was an app that was really never taken to the market, just due to developmental issues and never really having a working MVP.

And I stumbled across, but not really stumbled at, I kind of hit me in the face. This opportunity with ClosingCostHelp, looking back at all the experiences I had with previous startups, I realized that I could avoid all of those pitfalls with this opportunity and they will use that and you can get this to market and prove out the concept.

Brett Calhoun: Yeah, that’s awesome. Obviously, you know, this is a problem that you’ve seen firsthand. You got to see with your veteran home buyers every single day. And so I think it’s pretty cool that you’re not only solving a problem that improves the efficiency of your job, but also the lives of your clients.

And so that kind of goes into, you know, you’re obviously solving a problem. This is a need, but in preparing you to solve this problem that, you know what are some of the biggest challenges you’ve faced and in life, and how has that prepared you to be an


Josh Kaplan: I would say the biggest problem would probably be managing stress.

With entrepreneurship comes lots of challenges. There’s no playbook or training on how to do things correctly. There’s no right or wrong move. You realize after the fact whether or not that was the right move or wrong move or sometimes a month down the line. There are also long hours. So just learning how to manage stress and not have that spill over into every facet of your life, has made it very, I wouldn’t say easy, but, has definitely helped entrepreneurship.

Brett Calhoun: I feel that. And that’s, that’s literally part of our thesis at scale is that you know, we’re not just focusing on the company and helping you build that company and grow it, but it all starts with the entrepreneur and helping them with their own personal growth and so would love to hear just a little bit how.

You know, since you’ve been in scale for these last five weeks, how has that impacted your startup and what would you tell other founders thinking about joining?

Josh Kaplan: So that was, I, honestly, I knew I was in the right spot when Willy was giving his opening day kind of speech to all of the founders in Scale.

And it was explaining that a lot of other incubators are different. Similar programs have this mindset that you should just kill yourself for three months straight. And he thought he disagreed with that and thought it’s very important to have a good balance and still do the things that fill your cup and provide you happiness and fulfillment because that makes you more creative.

And the business side of things too. It’s all intertwined, and cohesive. So when I heard him say that it hit home for me, and I really appreciated hearing that. Like him and in terms of like joining something like Scale, you got some really successful people behind it. So just being around those types of people, I’ve always heard the saying that you are most like the five people you hang out with.

So if you surround yourself with extremely successful founders, that’s going to be your best chance.

Brett Calhoun: That’s a great point and yeah, I mean, it’s, it is pretty crazy. You know, being in the town of Columbia, Missouri, and how many successful entrepreneurs are here, like Willy and Jabbok Schlacks Brian Whorley, Wade Foster, and Brant Bukowski, in this town, not a city, so that is pretty cool.

It’s pretty awesome how they’ve all come together to be like this pillar company to help the community and build the ecosystem here. Now you’ve lightly touched on this, but we’d love to dig into the problem you’re solving and how you stumbled upon this. Or I guess, as you said, it just hit you in the face.

Josh Kaplan: Yeah. And you were mentioning before how many successful companies have come out of here? I mean, I think somebody, at some point, has to call Columbia, Missouri the Silicon Valley of the Midwest. Maybe one or two companies away from that. But, in terms of this problem, my background, or at least, for the past six years has been heavily in the VA mortgage space as a whole.

And not even in the VA specifically, it’s based the biggest barrier to entry for homeownership is the upfront costs at closing, whether it’s closing costs or down payments. But for veterans, it is that closing costs aspect of it. So on a daily basis, I was being asked or continue to be asked if the veteran could borrow money for closing costs.

So normally when you’re starting a startup. You want to go out and test the market and ask and try to find out if your product is actually needed. But that had already been done for me because year, after a year I kept being asked for this product to be there and I decided to stop telling people no and create this product myself.

So it was what veterans were asking for. It was the biggest problem myself, as a loan officer or realtors were running into having these closing costs. It was kind of this frustrating point that we fixed for all three parts.

Brett Calhoun: It just makes sense. It’s crazy how much it makes sense to people that the first five minutes in the conversation telling them about the problem and solution that we’re working on, kind of going into this question. So this goes straight into, because of this demand you’ve already seen.

Launching the products, like what, over the next 12 months, what is it that you really need to scale your business?

Josh Kaplan: So in terms of what we need to scale the business, it’s, we’re lending money. The more money we have to lend, the more we can scale. So one-word capital. Yep.

Brett Calhoun: It’s pretty crazy. You know, when we first launched this a few months ago, It was like, we had so much demand, but we were going to run out of capital.

And so if you, if you have a problem where you’re running out of money, because you have so much demand, you’re doing something right, but going into the next question, just kind of talk about the mission of the company and what excites you about this problem that you’re solving.

Josh Kaplan: We’re solving the problem of the biggest barrier to entry to homeownership, but there’s more to it.

And there’s a long-term effect of solving that problem too. We want to make as many veteran homeowners as possible. Homeownership, is the American dream and having something to call your own. I mean, it feels different when you go to home to a home that you own, as opposed to the home that you’re renting.

Then in addition to that homeownership is also. One of the best ways to build wealth for a long time. So for a lot of people, the equity in their home is the only retirement fund they have or their biggest asset. So the more homeowners we create, the better we’re building up the veteran community for long-term financial success as well.

Brett Calhoun: Yep. I think that’s fantastic. It’s such a strong mission. It’s pretty cool to be here too, just in the same town as the largest VA lender in the country. Well, this was fantastic. That’s all I’ve got Josh. This is really good.

So thanks for joining me and, stay tuned to hear more about ClosingCostHelp.

Josh Kaplan: Absolutely. Thank you.

If you are an investor and want to learn more about the Scale portfolio companies, please reach out to Brett Calhoun at or shoot a DM on Twitter @brettcalhounn.