The RTO Show "Let's talk Rent to Own"

Health Benefits That Actually Fit Small Teams

Pete Shau Season 6 Episode 12

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Health benefits shouldn’t feel like a second job. We sat down with Marshall Darr, CEO of StretchDollar, to unpack a simpler model for small teams: employers set a monthly budget and employees pick and own the plans that fit their lives. Instead of wrestling with group plans built for big HR departments, you move funding to the individual ACA market where coverage is guaranteed, networks are local, and the choices actually match real needs.

Marshall explains why small-group plans have become so pricey—healthy companies leaving the risk pool, fewer carriers in the space—and how ICHRA (Individual Coverage HRA) flips the script. The result is practical: a team in different cities can each choose the right plan from carriers like Blue Cross, Aetna, or Kaiser while the owner controls cost with pre-tax dollars. With licensed brokers acting as fiduciaries, employees aren’t left to fend for themselves; they get clear, human guidance to avoid pitfalls like ultra-high deductibles or uncovered medications.

We share tangible wins, including a type 1 diabetic whose weekly insulin costs dropped from $1,300 out of pocket to a $30 copay by switching to an individual plan that actually covered her meds. We also dig into the nuts and bolts—how setup takes minutes, why admin time can shrink by 100 hours a year, and when it makes sense to stick with a good group renewal. If you’re growing toward 50 employees, we cover options for transitioning without losing momentum.

If you’re a one to fifty-employee business in the rent-to-own world or beyond, and you’ve felt stuck between “too expensive” and “not enough,” this conversation offers a clear path forward: cash, choice, and coverage that works. Subscribe, share with a fellow owner, and leave a review to help more small teams find a better way to do benefits.

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SPEAKER_01:

Hello and welcome to the RTO show. I'm your host, Pete Shao, and listen, we're gonna talk about something that I I am not good with, but I know that we need it and rent own. Listen, I got Marshall Darr here. He's the CEO of Stretch Dollar. Now, if you've guys been at some of the places that we have in the A Pro uh conventions and all that, you've probably seen them. But here we're gonna talk about why and why we need it. Now, a lot of the RTO space, Marshall, really great to have you on here. You know, you know that a lot of our guys are one, two, three, four, five store owners. There's an average of five to seven people per store. They're short, but it's really hard to provide medical coverage for the people that we have because, well, you know what? We live in America, and although that's a great thing, it also becomes pricey on certain things, and medical care in the last few years has gone up, which is where you guys come from. So, Marshall, how are you doing? Welcome to the show. What's going on?

SPEAKER_03:

I'm good, I'm good. Thank you so much for having me. Uh, really excited to be here. Um, some of our first um companies ever using stretch all are a rent-to-own uh company. So it feels like going back to you know our roots a little bit to dig in and talk about it.

SPEAKER_01:

So do me a favor, Marshall, tell me your tell me your origin story. So your journey, what was the moment that led you to this? And you said, you know what, I I need to do this. I need there's something there that I have to fill, like like the Picasso to the page. What happened that you said, this is it, baby. I I got it.

SPEAKER_03:

Well, yeah, no, it's a good question because I don't think anybody wakes up as a six-year-old thinking they want to one day be a health insurance salesman, you know? And so life as a stunt man. I wanted to be a stunt man at like eight, and I I don't know why, but yeah, I think uh mine was a bulldozer, you know. It took me a while to get more grounded. But uh it's funny how life sort of unfolds. I uh wound up um trying to start a company when I was 25, went terribly. Uh as most 25-year-olds starting a business tend to. And I kind of crash landed at a company called Gusto, a small business payroll platform. About 10 years ago, I was rejected immediately when I applied, but the hiring manager thought my cover letter was funny. Um so I wound up getting uh foot in the door, and they brought me on. Um, and I did a lot of things there, but uh one of the most um formative moments was I worked on the team that was rolling out health benefits. At the time, Gesso had about 40,000 small businesses on their payroll platform, and they were looking to make it easier for these businesses to offer health benefits. And the kind of traditional way businesses offer benefits are these group plans, um, things called fully insured small group plans. And so we launched a program offering these businesses the only plans available, and it just didn't go well. It was uh these business owners found the plans to be expensive, complicated, found it hard to run. Uh, it's a lot of admin work you sign up for. So I thought that was weird. And I went from there to a company called Decent, which was a regional health insurance carriers, where I ran sales and marketing. And almost universally, when I was talking to these small businesses, we'd be saving them a lot on their health benefits. And still, when it became time to decide what hospitals were in a network or decide what pharmaceuticals were covered, they were like, I don't feel like this should be my call. I wish I could just give people cash and let them decide for themselves. Okay. And ultimately, that's what we set out to build with stretch dollar with some new IRS legislation.

SPEAKER_01:

Well, I I well, I'm gonna go I'm just gonna go back one second. Guys, if you don't think that your cover letter it matters, there's so many young people out there. We're talking to the CEO of Stretch Dollar, and I can say I I've I've seen it. It's almost like one of those things we were just, you know, one of the couple episodes ago, we were talking about the ads and how you can stop to scroll. Make sure that they stop and read what it is you have to offer because at the end you could be running your own business, and it's really important to do that. So I it's it's good to hear. Yeah, it's good to hear that there's somebody actually, you know, stopping and reading them going, you know what, this one's just a little bit different. So it puts you in the driver's seat, but why small business? I mean, you have that focus, and there's a there's a lot of different things. You said 40,000 companies, or was it you did say 40,000 companies that they had?

SPEAKER_02:

Yeah.

SPEAKER_01:

I mean, that's a lot. You know, stretch out is focusing on the smaller companies, and I know that it's it's it's expensive and and they've got these plans to build. What about that? You said this is gonna be the ripe area for for Marshall Darr to make his stance and make it happen.

SPEAKER_03:

Yeah, no, it's it's a good question. I think I've just always been pretty fascinated with small businesses because in a lot of ways it feels like it it really is the American dream itself being embodied. It's somebody setting out to uh make a positive impact on you know their community, their world through creating a business to help push uh the world a little bit in that direction. Now I can say that as a small business you know owner myself, there's 15 employees at stretch dollar. Um it just I think in America there are a lot of interesting ways you can make uh large scale difference. And I do think these small businesses can make very strong and outsized differences in a way that like I didn't imagine I could at working at a larger company. Yeah.

SPEAKER_01:

Well, I mean no small business is the backbone of what we really do, and I never really understood that until I like you, my first business, it tanked. Okay, it went down. As a matter of fact, it's on my shelves back in at my other uh studio, and it's you know, it's there. It was my first uh receipt of of you know being able to say, I opened it, you know, I had my operations tag there, and it was like, I can do this, right? I have I I can I can get it done. It it crashed and burned. But I always held on to it because it it opened my eyes to so many more things that I didn't know. And so I give so many kudos to the people that are have these small businesses and they're trying every single day to get from point A to point B, especially my rent-owned industry, because it's not easy. This is a cash-intensive industry, and you can make a living out of it. But you also want to take care of the people that work for you. You want to make sure that they stay healthy, right? Nobody wants to have a business where it's like, yeah, I want to work you to death, and then you know what, you don't get to you have a day off, you can't go see the doctor, something happens to you, sorry, you're kind of you're kind of uh SOL. You really want to take care of them. And and so health is health is it's almost one of those words that you're like, oh my God, healthcare. Because it's always in the news and it's always going on. But you found a way to make it easier for these smaller companies, the people who are the backbone of our of our industries and our country to make it a little easier. Where did this idea like well? Let's go back to your team. Let's let's start there and then we'll we'll kind of branch out. You have and and I hope I'm saying this right, Kaisa Molina? Kaisa Molina.

SPEAKER_03:

That's your COO.

SPEAKER_01:

Yeah. So she saw your vision too.

SPEAKER_03:

Yeah, I mean she helped me make it. Um I I think in any good partnership, uh, you know, the ideas are refined through collaboration within it. And so I like what stretch all is didn't just jump out of my head, you know. It uh took a lot of conversations, a lot of thinking, and a lot of learning. And Kaisa was there every step of the way. Uh I've I've been working with Kaiser for the last 10 years. Um, she was my first direct report ever, uh, back at Gusel in Brilliant Mind, uh, like Crazy Executor. And I think another one of those people who's like um just believes they can change the world.

SPEAKER_01:

That's a good vision. It's it's not an easy one, but it's one of those that if you feel like you can make a difference, you can really kind of put yourself out there. You don't mind being out on a limb, which is sometimes what we do when we have small businesses, right? And we're trying to take care of our people. So let's talk about the product here. Let's talk about what it is that you actually do. What is the ICHRA? Can you explain that to me? Because I have listen, I saw so many acronyms and things going to your website, just kind of researching this a little bit. I have, I am way out of my league. Now, if you want to rent something, you want to sell something, want to deliver something, I'm your guy all day long. You want to get health insurance? Here's Marshall Darr. Can you explain that to me?

SPEAKER_03:

Yeah, I uh so I can, and it can it can get complicated, but it can also be held simple. Um, basically, the traditional way businesses offer health benefits was really designed for much larger businesses, uh, people with big HR firms, brokers, uh, and ways to sort of create a binding entity. Um, the business itself owns the policy, all the employees are members of the policy, the business pays um and ultimately decides what carrier people use, what plans they can get, the rates they're charge, everything. But it's a very centralized kind of approach. And historically, health insurance companies have always looked at small businesses as basically tiny versions of enterprise businesses, which I don't think is correct because you don't have all that infrastructure, you don't have all those people, you know. But the expectation is still that you're gonna go get that group policy, pick the carrier, manage all the enrollments, all of that. What ICRA does, uh legislation passed in 2020, and functionally it for the first time ever, it allows for uncapped pre-tax employer funding to employee-owned health plan premiums. So instead of picking a group plan and managing all of that, instead you can just provide monthly funding that employees use to pay for policies they pick and own themselves. That's what we do at stretch off.

SPEAKER_01:

So so help me out with that, because when you say policies, I'm thinking the big four or five, right? The Cygnas, the Atnas, the Humanas, the Blue Cross, Blue Shield, you know, and stuff like that. Yeah. Is that what you're talking about? Or is this a little bit different?

SPEAKER_03:

Yeah, that is um what I'm talking about. And so historically, like um if you wanted to offer health insurance to your employees, you'd have to pick three blue cross plans, maybe three if you're lucky. They could pick from that. What this does differently is instead you're like, here's a couple hundred dollars a month. Uh, you can pick your own, uh, whether that's Cygna, whether that's Aetna, whether that's Blue Cross, Blue Shield. Uh, and the employees can move to plans that fit them a little better and typically save a lot of money in the process.

SPEAKER_01:

So what's what saves that money? So it I guess my big question is because a lot of guys are gonna ask me, if I have stretch dollar and I do this, right, and I'm putting money into it, wouldn't I be putting that same money into the insurance you know, programs that I already have and then just offer them Humana or Blue Cross Blue Shield? What makes this one not only a save a saving grace for some of the people that own the small businesses, but the people that are a part of the small businesses?

SPEAKER_03:

So it's a good question. Um, and one of the unfortunate undercurrents in insurance over the last 10, 15 years is the fact that the traditional plans that small businesses can offer their employees, these plans called fully insured small group plans, they are twice as expensive as they were in 2010. And on top of that, many carriers are actually leaving the space. And so it's not good.

SPEAKER_01:

But you know, why is that? Why why what what is causing the last 15 years? I mean, I can only imagine COVID probably played a small part in that. But like, what what is the reason from 2010 to now? And and maybe we just leave out COVID. I know it might be a hard thing to do, but like why is it so much more now? I mean, actually, you know, I would think that the birth rate's actually going down. We're not having as many kids as we should. We are living a little longer though, yeah. So maybe that's what it is. Like, what it what is it?

SPEAKER_03:

So uh the fully insured small group plans, in my opinion, have been disproportionately affected by larger trends in the market. And this isn't to get too wonky on anyone, but effectively we're talking about you guys. Uh effectively, like um there's been a rise in like the medium to large business side of something called self-funding or level funding, where the companies actually hold a bit of their risk. They have a pool of money they set aside, they uh essentially get their employees underwritten and priced to their health profile. Fully insured small group plans don't work like that. It's basically everybody who joins is offered it at a flat rate. And the issue there is that more and more of these healthy larger companies are exiting the fully insured small group risk pool, which means that as healthy companies leave, you're left with less healthy companies, which means those insurance rates have to go up to compensate for it. So, in in a way, it's the victim of you know, it's the big sack bully. It's the rich get richer, it's the the little guy is left without the options that these very large companies have. And so, in a lot of ways, these small businesses wind up subsidizing the cost of larger businesses who don't want to do that.

SPEAKER_01:

Well, you know, I I've always been a fan of the more people you have doing something, the more of it. And I want to I don't want to say it's a race at the bottom, but it's always what's gonna differentiate me. And I can say a whole lot of things, but you know, in the end of the day, a lot of people are looking at the price tag. And I am a firm believer in service. That's what we do in rent to own. Our service kind of puts us ahead because the value of what we give them. Yeah, but also as you're looking at it, when you have, let's say, 10 different carriers, they're trying to figure out, okay, how do I beat this guy? Well, I can offer this and this, but maybe just giving a lower premium. When you have less people, right, and you cut down to two or three, and they all kind of all agree this is the price range we're gonna be in. Well, who's gonna fight it? Nobody's gonna offset it. You're not gonna have that one company go in and be like, hey, I'm gonna be like$50,$100 less every month, and then they're gonna have to, oh god, but now we have to change our pricing. So I totally understand that, you know, but when we talk about small to medium to large, what does a company size look like? What's a small company look like as far as employees, medium, and then what does a large company look like as far as the employee count so that we kind of understand where we're we're going with that?

SPEAKER_03:

Yeah, absolutely. So stretch are specifically works with uh one employee to 50 employee companies. Once you get above 50 employees, some federal requirements kick in and you kind of fall into a different bucket. And so when we think about like medium-sized employers, that's typically are 50 to 500 employee companies. And then 500 plus, thousand plus companies, those are all very, very often self-insuring to some degree. They again have those like large HR departments and the the brokers and the TPAs that can manage that for them. But that to expect, you know, the medium-sized businesses and the smaller size businesses to be able to do execute something as complex and cost prohibitive to get going isn't quite realistic. And to put kind of like a finer point on some of the benefits of the system, like we can take stretch dollars' example ourselves. We were our own first client. Kaiser lived in San Francisco. I know it works because we did it first. We did it first, you know. We did it first. Yeah, we're not gonna ask anybody else to wear the first bulletproof vest, you know?

SPEAKER_00:

Right, there you go.

SPEAKER_03:

And so you want to try this out? No. But Kaiser lived in San Francisco, she wanted a Kaiser policy. At the time I was living in Philadelphia, there's no Kaiser in Philadelphia. And instead of us having to compromise, like pick some group plan that might not work, I was like, okay, everybody gets$500 a month. I was able to find a great Heimark policy, she was able to get a Kaiser policy, and past that I was able to not really think about this functionally ever again. Every year I think about it for 20 minutes with a renewal where I might re-adjust the amounts we offer. Uh, but functionally, each employee at stretch dollar can pick a local policy that really works for them. And we've seen that have a huge impact on the kind of uh ability of employees to match their health needs to their policy. We had a company in in sorry to get on a soapbox. No, no, go ahead, go ahead. But we had a company in South Florida, actually not far from you, but that was on a Florida Blue Home territory. Look at that. Uh they were on a Florida blue group plan and they had a type one diabetic uh that was an employee. Her insulin wasn't covered, so she was paying thirteen hundred dollars a week out of pocket. We were able to find her an individual policy out of pocket? Out of pocket. We could find her That's like what$75,000 a year or some ridiculous number,$70,000? And so naturally, she was rationing, she was making these very hard decisions just to try and get access to her medicine. We were able to find an individual policy where her medicine had a$30 copay. And that's kind of what you can do when you can match people to 100 policies instead of three.

SPEAKER_01:

Hi, I'm Pete Chao. You may know me from the RTO Show podcast, but today I'm doing something a little bit different. April and Wow Brands have launched a special project to bring the story of our industry to life like never before. They've asked me to sit down with some of the true legends of Rent to Own, capturing their stories, their impact, and their vision for the future. And now I get to share those conversations with you straight from the legends themselves. All of this leads to something groundbreaking, though. A new book, The Rent to Own Revolution, a Definitive History of Advocacy and Consumer Access, written by April's CEO Charles Winterman and Wildbrand's CEO Brian Kraft. The book explores the grassroots of RTO, the advocacy that has defined it, and the future that we're building together. Here's where you come in. We're giving away free copies once the book is released. Just head over to the rtorevolution.com and sign up for a chance to receive a copy in early 2026. Don't miss the chance to be among the first to hold this piece of RTO history. That's rtorevolution.com. Check it out and become a part of RTO History. So let's talk about a let's say a company that we have 10 people. Okay. So, and and I'm just I'm trying to lay this out there so that I understand it, but I also want the listeners to understand too. So let's say I have 10 employees. Now, is the idea that I will be spending the same amount of money on insurance, but they will get better coverage, or is it that I will save money on the insurance and then they can go pick their own?

SPEAKER_03:

Uh so on average, we'll save you a hundred hours of admin work a year by not having to do the group plan work. And you can set your own budget. Most group plans you get quoted, and they're like, this is how much it is. With stretch dollar, there's no minimum contribution and no minimum participation. Meaning if you can afford$300 a month, we can work with your employees to figure out what they can do with$300 a month. We don't require you to pay, you know, the full policy and then try and cost them back from your employees. It's it's a truly flexible budgeting tool.

SPEAKER_01:

Now I know that open enrollment is every year. And again, I'm going for layman's terms here, but uh when you when you sign with an insurance company every single year, that is a contracted amount, right? So we say we're going to do this, we have one year of this, and it means that if I'm if I'm stuck at five or six hundred dollars a month for those employees, that's what I'm stuck on for the next 12 months. All right, is that is that how it works?

SPEAKER_03:

Yeah, uh yeah. That that was that was right right enough.

SPEAKER_01:

So with stretch, right? I know, right? So with stretch dollar, like the point of stretch dollar is saying, okay, now I have this budget. Let's say I can't do$550, that was killing me, but I can do$500. Okay, so I can do$500 per employee. It's been a rough year. We do$500. Where does stretch dollar come into all this? I've got the 10 employees, I can do$500. I call you up, Marshall, or or or you know, your COO, Ms. Molina, or Mrs. Molina, I'm sorry. And uh, you know, kind of go over where do you guys step in and what happens at that point in time after I make that phone call? Where do you guys shine as far as this service?

SPEAKER_03:

Yeah. So basically, we uh on our platform, you can create your own ICRA policy within about 10 minutes. You can invite your employees, we integrate between your bank account and your employees' bank account. So once they have verified coverage, we'll move the funds for you each month, tax-free. And we also work with your employees to match them to policies. We have health insurance brokers. We're licensed in all 50 states. And we can sit down with your employee and be like, okay, look, you have this$500. There are 100 health plans you can pick from. We should look at these four because they match your health needs.

SPEAKER_01:

All right, so I got a question because this is standing out to me. Yes. I know I know people are saying, you know, they're looking at the grocery bill and they're like, holy cow, they're looking at the gas bill and they're like, holy cow. So let's say, and I'm just we're gonna stick with that$500 number, right? So I I have 10 employees, it's$500 a month that on top of whatever I normally cover for them. And I say, All right, guys, we're gonna go with the stretch dollar thing. I'm gonna give you$500 a month, they're gonna do this, you know, thing where we connect the banks and it's gonna go straight to your bank. What stops somebody from going, you know what? I don't want insurance. I'm getting$500 more a month. That's a huge raise. I mean,$6,000 a year, yeah. You know, from doing that, or going, you know, this, and and and I'm only saying this because some of the people that we have, they they live life. Yeah, they're just you know, blue-collar regular people. They live life. You know, things happen. I got a flat this week, you know, uh daycare is twice as expensive for whatever reason this week, you know, I I've my groceries are low. How do you get it so that that money is always consistently there for their insurance needs and it doesn't kind of fall into another bucket?

SPEAKER_03:

Yeah, it's a very good question. The employees purchase their health plans through our platform. And as such, we become broker of record on the policy so we get visibility into their health insurance status. And you know, they there are always like concerns about fraud. Uh we've been lucky we haven't seen any yet. Uh, we have had a few employees though switch their credit card and forget uh about their payments, and we've been able to reach out and get that fixed for them. And so the service doesn't stop just because they bought a policy. Like we're we're there to help them throughout the year on uh how they engage with their healthcare. And sometimes, you know, that's as simple as reminding them that, hey, you gotta switch your credit card here.

SPEAKER_01:

Yeah, well, I mean, just I'm just and I've seen a lot of things happen in my day. I've been doing this industry for 20 plus years, and I've seen that uh sometimes when you give a dollar, you might think that it went to something, but they have different plans only because needs change, people change, and everybody's different. So the choice, the choice and the simplicity of it. Is there choice versus simplicity? Is it choice and simplicity? Is it what is walk me through this? I'm I'm here, right? So I'm I'm on Joe's rent to own. Joe says, hey, we're gonna try out the stretch dollar thing. Joe, I like my blue cross blue shield. Joe's like, well, I like it too, but I can, you know, I can't afford that. Okay, so what are we doing? We're gonna go to stretch dollar. I'm gonna give you$500 a month. I get you all set up. What does that look like to me then as somebody who is now looking at what what you're doing? Um, what can I say? I know you said you you you set up a little bit portal and you kind of walk them through. What does it look like for me as the person trying to get this insurance?

SPEAKER_03:

Yeah, it's a good question. So you receive an invite from stretch dollar, basically being like, hey, Joe's rent to own shop is offering you$500 a month for your insurance.

SPEAKER_01:

I love how you said that too, man. You'd really like, yeah, Joe's. I like Joe's okay.

SPEAKER_03:

I was just saying, I'm just saying. Uh but Joe's rent to own shop is offering you$500 a month for your insurance if you get it through stretch dolly. Uh you log in, we integrate with your bank account, and then we take you through a shopping flow. You can request to sit with a broker and basically look through all the policies together, or you can pick your own on the platform. Either way, we take care of you, and then you essentially submit that proof of coverage, we watch the policy, we make sure you get the money each month.

SPEAKER_01:

So, a couple things that I want to know. Is this region specific? So because it's a because you're doing like the 500 and it's not a big plan that I'm getting from you know Aetna or whatever, you know, if if I'm in Florida, is it more tailored to Florida or is it still an overall plan? Like if I'm visiting mom in Missouri, I can if I happen to break my leg, I'm not in trouble.

SPEAKER_03:

Yeah. Uh that is an awesome question. So it's both, basically. Um, the health plans available are gonna be regional health plans. Uh, in terms of, you know, if you live in Houston, you'll see Houston hospitals, you'll see a Houston-based network for your specialists and for basically uh health care you can schedule. But if you're traveling, you break your leg, you have to go to the hospital, any hospitals build as in network near you. Um these plans are something called ACA compliant, which means they cover the 10 essential health benefits. Uh there's no lifetime cap on coverage, meaning you can't overspend and get stuck with any sort of a bill. Um they cover the 10 essential health benefits. And most importantly, in my opinion, they're guaranteed issue. Uh, the plans are guaranteed price, guaranteed issue. No one is ever denied access to these health plans due to a health condition or charge differently if they come with one.

SPEAKER_01:

So basically, you know, with urgent care and emergency rooms, no matter where I go, I'm still good. I might not be able to get my, you know, my prescription filled in the middle of nowhere, but if if anything happens to me, they will cover me.

SPEAKER_03:

Yeah. Okay. You you might not be able to go to like your favorite podiatrist in Milwaukee if you live in Orlando, but Right, right.

SPEAKER_01:

If sorry, guys in Orlando, you're at your SOL. Yeah. But okay, so then the other thing is, so I'm looking at that, and we've gone through this whole thing. Joe is trying to take care of me, right? And we're sitting there. So when that list comes up, when stretched daughter comes to me and we kind of open up that portal, you know, just for the sake of everybody in the RTO industry understanding this, and for the entrepreneurs that we have out there trying to open it up, what is their selection like? And and then just, you know, I just want to know like, is it two or three? Or is there a whole lot of things out there that I just don't know about? Listen, my favorite chips comes with one flavor uh that I like, but listen, there's usually like five or ten others that make the same original lay's chip, right? They don't make that that chip. So when I open this up, is it like is there quite a few names in there, or is it these are probably the basic two or three that you're going to see, regardless of the region you're in? You're you you know, you're not gonna have as many choices as you would the other way around. You tell me.

SPEAKER_03:

So if you live in any sort of a major metro, typically you have between 60 and 110 plans to pick between. Uh if you're way out there, like there are areas of like West Texas, for example, where Blue Cross Blue Sheel of Texas might be the only option. But if you you live near any sort of like uh population center, you typically have at least three health insurance carriers to pick from, and each of those carriers typically have 12 to 16 different plans you can pick between.

SPEAKER_01:

Well, you know, it's funny you say West Texas. I actually do have a friend who's out there in West Texas. He's got three stores now. It's called Rent Buy. His name is Leroy Steen, and I was going to pitch that to him. Leroy, I'm just letting you know I'm thinking about you because you know he's got he's a small business owner. And you know, I'm gonna tell you right now, the guy is sharp as attack and he does everything he can. He's he's got his eyes on growth. But right now, I mean, he's still at three stores. It's gonna take a while to hit that fifty or that 49 mark. I don't know if it's 49 or 50, but he's it's gonna take a minute to get there. So it's like, how do it how does he take care of his employees the best way that he can, but also doing best to make sure that he saves enough to grow more, you know, stores to have more forest people. Yeah, and so that's always uh, you know, in in important. Um, you know, you said something about uh the benefits and and you know, I'm sure you guys are licensed and all that stuff. What role do you p play and and the employees that you have play in making you know all of these listen? I have no idea. I'm telling you, my wife is like is like my caretaker when it when it comes to open enrollment, she's gotta read it to me like I like I don't know what this is. Just tell me that I'm covered and I go in there with a card, right? But there are so many things, there's so many definitions, there's so many, you know, new ways, and hey, this law passed and this is happening. How do you guys work that out with these people that are literally, I just want a job and I want to know that if I have a car accident, I'm gonna not not like Morgan and Morgan in a car accident, but like, you know, something happens to me and my back hurts, whatever, and I need it. How do you help them out? Like what first off, what kind of licensing does it take to be a stretch dollar to help them and and how how much do you help these people in this decision making?

SPEAKER_03:

Yeah. Uh so all of our all of our sales reps are health and life licensed, which means they've passed their state-based health and life exam. Most of them are licensed in all 50 states, uh, meaning that wherever you are, they can sit down and they can help you legally as your broker of record, which means um they carry fudiciary responsibility to the person they're working with, even more so than they do the stretch dollar. It's their um legal obligation to take as good of care as you as possible when it comes to picking your health plan. And I'm a very firm believer that you shouldn't have to be an expert in the conceptual ins and outs of health insurance to get great health care. And as such, I love that line, by the way.

SPEAKER_01:

I just want you to know that. I love that line because I I don't, but I want to make sure that if I some, if I get sick, I'm okay.

SPEAKER_02:

Yeah.

SPEAKER_01:

So and I and I know a lot of people who feel that same way. I mean, honestly, like you just we have so much going on. I don't know how to pick a plan. I don't know all these wordings in the Icra that you're talking about. Yeah, you know, I don't I'm telling you, I have no idea. I see, you know, somebody in urgent care, and I just want to know that if I go there because I feel like absolute dog, that you know, somebody's gonna take care of me and whatever insurance I have is good. So to know that they're covered in the 50 states and they have a legal responsibility makes me feel better. Yeah, you know, I like that.

SPEAKER_03:

And the and the other thing too is you don't have to use our brokers. If you know somebody um with a health and life license, um if you've been working with someone, you can use them. You can still use the funding mechanism of stretch dollar. We're here to be an asset, there's no requirement to go to us for the advice. Uh the general um thinking though is like I do want my team to be opinionated about this. I think there are certain coverages that are better for people and certain coverages that are worse for people. Obviously, there are going to be exceptions to the rule, but personally, I don't love super high deductible health plans. I know some people have the HSA set up and they got all these mechanisms funding retirement and all of that from it. But when you think about the average person, like we really want you to be able to have a copay to go to the doctor, have a copay to pick up some of your medicine, have a copay if you have to go to urgent care. And there are plans out there, and oftentimes the difference is like three dollars between whether or not you have to cover the first$7,000 or if you uh can get$25 copies on doctor visits from day one. And so I I think it's kind of it's it's in my opinion unethical to pretend like all of these are the same.

unknown:

Right.

SPEAKER_01:

Well, so I got a question. Um because you were talking about$3 difference, and you know, the first thing I thought with$3 was like good RX. You know, did stretch dollar work with that as well?

SPEAKER_03:

Uh so we don't specifically work with good RX, but we do have a partnership with a company that does medical bill negotiation, where if you get a uh high-ticket bill, anything over$5,000, they'll negotiate it down with you. And on average, they get it reduced by 60%. So we have um resources there if you get any big bill, and we are just talking with a firm to hopefully get everybody, uh every stretch dollar related employee access to discounted GLP ones.

SPEAKER_01:

So I gotta ask, as you're going through this, right? You even made the comment yourself. Some of the first people that came on were rent-owned people. Thank you guys for doing so. But as that happens, you know, I I would imagine, because whenever this started, you said that there was a change. 2010, 2015, 2020, 2025, it's going up. Did you guys start with like a hey guys, this might be the best recommendation I have for Joe's rent owned and all of a sudden next year is like uh you know, just so you're aware, you don't have to, but this is my new recommendation because healthcare is going up. I mean, have you had to evolve with that as far as what's going on and what you tell people, hey, listen, I want to save you money, but at the same time, if you give them fifty dollars a month, it's not gonna work as well as it used to, or 150, it's not, you know, you're gonna have to ante that up a little bit more too. I mean, how does that how does that work? How does that you know go with your daily practices?

SPEAKER_03:

It's a I really appreciate that question because I feel like when you start a business, you sort of have to predict what the future is gonna look like. You kind of have to take a bet because it's gonna take you a few years to build to be what you need to be to take advantage of the future you imagine is going to happen. And three yeah, and so three, four years ago, I was I was looking at the group health insurance market and getting pretty dejected. I mean, I've been a licensed health insurance broker for about ten years now, and rates are going up all the time, the market was getting squeezed, we were seeing carriers pull out, and I think there are a subset of people who believe that there's a better than not chance that ICRA becomes kind of like the end state of how we all get benefits, uh, where we all get employer funding and then we all get our health plan through the ACA exchange. And the intention behind how it was designed by the people in Washington who put it together was as sort of a counterweight to these employer plans um that isolate the risk of good and healthy people. Because the the basic idea behind insurance is if we all get in a big pot and we all put money into the big pot and we have to take some money out when we get sick, there'll be enough money for everyone. And that idea kind of breaks if you let people with a lot of money who don't have a lot of health issues make their own little pots everywhere. And so the idea behind ICRA is like, how can we get everybody into the same broad risk pool, whoever you are, you know, you can be a million billionaire, you still pick from the same plans as um Joe down the street. And if in that concept, from an economic standpoint, that should make it affordable for everyone. And so, in some ways, we started stretch all our with an uh with a bet on where this all was gonna end up, which in my opinion should be with your employer less involved in your healthcare decisions, it should be in them acting as a financial enabler for you to make your own healthcare decisions. And I think the version of the world where we all get our coverage through ICRA is going to be a better version of the world than the version where we don't. You sound like a futurist.

SPEAKER_01:

You sound like somebody who's saying, you know what, I'm gonna be the Amazon of healthcare pretty soon, and it just has to catch up. You are on the front side of that curve. Yeah, I love the idea. You know, ICRA has been available since the federal legislation enabled it, but you know, the adoption wasn't 100% universal. What are the some of the barriers that you encountered when educating your employers uh that have this insurance or or to go through you with it? Like what what you tell people about the options that you provide and why you know you're ahead of the curve and they should go with you.

SPEAKER_03:

So I think that there are a lot of great ICRA admin platforms that have emerged recently. We're one of the only ones exclusively focused on small businesses. So there are certain situations where we can even work with employees to waive what the employer is offering and get government subsidies instead. Uh that's something unique to focusing on the sub-50 employee space. My general sentiment is that like anyone who says that they're gonna be the perfect fit for you in every situation is probably lying to you. And so there are situations where you shouldn't go with stretch dollar. You shouldn't go with stretch dollar if you're on your a group plan and your renewal was low, you're very happy, there's no reason to move in that situation. You shouldn't go with stretch dollar if you would like to get real complicated with it, if you would like different reimbursements for different medical costs outside of the core uh health insurance premium. And you shouldn't go with stretch dollar if you can't afford to offer benefits. Legally, it's not required for small businesses to offer benefits. I know emotionally we all want to, and we all want to take the best care we can of our people, but I've had small business owners reach out who thought that like if they didn't offer something they couldn't afford to offer, they were gonna get some crazy tax penalty, and it's not true. This is designed to be an option for you when you're ready for it, and it's designed to be the most accessible kind.

SPEAKER_01:

It sounds, I mean, how long have you been doing this now? Uh coming up on three years. Yeah, I'm gonna I'm gonna step outside the box for a minute. We'll get back into it. I just want to know where did the uh name stretch dollar come from? I mean, it's right on the nose, right? I you gotta love that. But like, where did it come from? What made you guys think that you know what? Hey, this is you know, because I have no idea where Aetna came from. I have no idea where Blue Cross and Blue Shield came from. Yeah, but it is just is what it is, right? Like, I don't think Amazon would have been the name I picked, but then you know it's a household name. What made you guys decide, you know, stretch dollar is where we're going with this?

SPEAKER_03:

So we had decided we wanted to start this company. We knew of the concept before we knew of the name. And I was asleep and I just woke up one day and I was like, Stretch dollar, I wonder if that domain's available. I looked it up and I saw it was three thousand dollars. And so I let people there you go. We were just talking about that. Yeah, I let the team know I was like, here are like my my like six ideas for a name. Uh they all like stretch dollar, and I was actually trying to convince them to go with other objectively worse names because I could get them for like five bucks instead of the three thousand.

SPEAKER_00:

So literally just talking about that. Like I got mine for five dollars. I guess it was a crap name. But you guys got charged a whole lot more.

SPEAKER_01:

And somebody must have thought that it was a good idea. I mean,$3,000. It must have been like something that was unique and stood out.

SPEAKER_03:

Yeah. I mean, it is really nice that we're not some zanally spelled.ai, whatever. It's just stretchdollar.com. You just go there, we'll take care of you, you know. And so I think they charged us more because it's two words stretch and dollar, and it's a concept, you know, it's make your money go further. It all works. We do have a jingle on our uh about page. Uh, I don't know if you saw that.

SPEAKER_00:

Oh, wait a minute, wait a minute, Anthony.

SPEAKER_01:

We could get a singer on here pretty soon. What's it come on? What's the jingle?

SPEAKER_03:

Oh, I'll have I'll drop a link. It's I can't do it justice. We we found an incredible artist out there.

SPEAKER_00:

I know, right?

SPEAKER_01:

Let's just hear it. Well, listen, you go you drop me the jingle. Hey everyone, it's Pete Chao here from the RTO Show podcast, and I want to tell you about a company that's making a real difference in the rent owned space. WoW Brands. I've seen firsthand how they approach marketing. Let me tell you, it's not just about ads. While brands build complete digital ecosystems designed specifically for the rent-to-owned industry, their e-commerce and lead generation strategies are built to bring qualified leads. And did I mention that they are actively working with the rent-town industry while also being members of April and Trib? Listen, these folks are passionate problem solvers. They don't just slap something together, they design, build, and scale the kind of digital retail tools your business needs and your customers actually want. So if you're serious about growing, reach out to WoWBrands at WoWBrands.com. I trust them, and I think you will too. You went from a uh$1.6 million present round in 2023 to launch a$6 million seed round led by uh is it FICA Adventures? FICA in Oscar Health? FICA, okay. So uh as a founder who's been through multiple fundraising rounds, you know, rounds, what was that journey like? What was that to just go out? I mean, like essentially asking for money, right? I mean in a very you know uncharismatic sentence that I'm saying there, but I mean it's you know, you got to get people behind this idea. How did you present it in a way that you got these people to say, you know what, this is where I want to be. I want to back this, I want to do this. How how are you doing that?

SPEAKER_03:

Um not well at first, you know. Uh we had a bunch of people say no. Um, but we knew we weren't on to something and we kept um kind of our nose down and kept going. And, you know, in a lot of ways, I think I think a lot of the stories that come out about fundraising are about like the real clean, real easy, real fast rounds. And I don't think those always yield the most interesting companies because like if you if everybody agrees that what you're gonna do is obviously the future course, there's gonna be a lot of competition, there's gonna be a lot of noise, and who knows? I feel like the interesting companies are the contrarian ones, the ones that people are split on, the ones that like maybe a lot of people think aren't gonna work, and a lot of people didn't see the future of ICRA quite like we did when we launched it. At the time, like level funded plans were very popular, PEOs were popular, and like the concept of an ICRA hadn't really like caught on yet. And so uh it's funny. Um FICA actually passed on our pre-seed because they were like, This seems wild. I don't know if it's gonna work. And then they heard we were going out for the seed, got back in touch, and wound up leading the round. And so I I think we've been lucky in that like the future we thought we were building the company for is looking more and more like the future we're coming into, and that makes it easier and easier to put together a fundraising pitch. But it was my first time ever fundraising, it was it was not easy, but you just gotta like I I spent a couple summers like fundraising going door to door uh as like a door-to-door uh charity collections sort of thing, and I think in a lot of ways you gotta treat fundraising the same way where you're especially in the early stages when you just need some money to prove that you're on to something, you gotta just keep knocking on the doors.

SPEAKER_01:

So help me out with that then. So we where where do we where do we start? Where you know, what are something that you can see? We started here. Uh, you know, you and and Miss Melina were the first ones on board. Now you're at 15. Where are we going? Where are the metrics hop up at? What is the what does the business cycle look like? We're here. How how long did it take to get from U2 to the 15 and then where are you going from there? Where do you see this another five, 10 years?

SPEAKER_03:

Yeah, it's a it's a great question. I mean, we we sort of we've been very lucky, I think, in a lot of ways. We found some great distribution partners. Uh, we're up to a couple hundred companies using the platform currently. Next year, I think we'll be up over 10,000. Uh, and so I think it's gonna grow really, really quickly over the next couple of years. And I am just very focused on making sure the company deserves it, you know. Uh, we have to earn it by making sure that we take better care of people than their other options could have. Um, and I think there's the real potential in that in matching people to policies that work a little bit better and improving employees' relation with their healthcare. I don't think it's as simple as like ICRA is gonna be big, we're one of the ICRA companies, we deserve a big cut of that. Like, we we gotta earn the spot.

SPEAKER_01:

So, well, I can tell you right now nothing comes easy, right? It's gonna be a challenge as you as you walk through the valley, right? Um, you see a lot of things that are coming through. You've got to have some kind of leadership to make sure that your people are gonna stay with you to see that vision to come on and say, I've never heard of stretch dollar because it's brand new. I've got two people working here, I've got to get you on. Give me some of your leadership philosophies that have gotten you to where you are, that you that you embody through stretch dollar. That if I wanted to go to stretch dollar as an RTO guy and I I want to know who I'm working with, what are your some philosophies? What what what do you guys do? How do you believe and how do you lead your people?

SPEAKER_03:

Yeah, I think we really focus on the value of incremental progress, on getting just a little bit better every day. I think it's the most underrated aspect of life of just getting like that inch or two better every single day, and that progress really compounds. And so what we focus on is not even like the day-to-day results, it's the day-to-day improvement. And Kais and I have always been very aligned in that kind of philosophy, and it's led to us developing um a really strong team and being lucky that we attract some really talented people. And the whole goal is like, how can we create a situation where everybody can do some of the best work of their careers, knowing that we're not entitled to these employees staying if we're not living up to that standard as their employer?

SPEAKER_01:

You know, leadership is one of those things that we we probably sit there in all day. I can have a podcast on nothing but leadership because it's so important. But as you talk about, you know, to your people and and what you're doing and your business models and where you want to scale to, you know, there's always that idea that we're gonna hit some bumps in a road. You know, there's there's things that are gonna come and they're gonna happen, and maybe we didn't sell Joe's rent own as much as we'd love to. Talking about selling to people, uh, what is a number and is or is there a number? Let's say that I have one employee. Is that a number that I should come to you with, or is it like at 10? Is it at 15? Where's where where does that begin between the first and the 49th?

SPEAKER_03:

Yeah. Uh well, our our average size right now is eight. And there's a ton of noise. Um, because we have, you know, the 40, 50, well, 49 employee kind of companies. Um, we have the one employee companies, too. And I think health benefits are really like reflective of a business's personal journey. Uh, where and it's not day one, you know, this isn't like the first step on Maslow's hierarchy of business needs, you know. Like you gotta keep food on the table, you gotta keep people employed. But it does come, you know, and it might be an employee is experiencing a health issue, it might be you're trying to recruit someone, it might be, you know, you just feel like you're ready to take that next step and do your best to ensure that you can retain these people. You've spent so much time recruiting, training, onboarding, because employee turnover can be so expensive to an organization, not even just monetarily. It's um can be emotionally draining, it can be, you know, you can lose so much of that sort of institutional knowledge. And I think deep down, most every employee I've met has wanted to take care of their people. I think we're trying to put together a way to make that a little easier.

SPEAKER_01:

So as you grow, right? The idea is to grow. I'm curious. Sorry, let's say I'm I'm Joe's rent owner. I start with you. I've got 10 employees and then 15 employees and then 25 employees. You still use a stretch dollar, it's good. Now I'm at 45 employees. Yeah. Now I'm at 49 employees. Okay. Like when they hit 50, is it like, hey, buddy? Say Anara, you know, Joe, I'm sorry, it was good to meet you, but uh time to hit the road, or or how does that work when you have somebody who's trying to be the best they can be to all their employees and their communities and grow, you know, business-wise? And you, you know, they might have just taken that next step from let's say, yeah, you know, they open a store, there are 47 customers or employees now, they open a store, there are five to seven more that puts them at 52, 53. How does that work?

SPEAKER_03:

Yeah. Stretch dollar and what they're doing. So we we can facilitate a transition, and then in some ways it depends on what you want the next step to look like. If you are love and life offering ICRA policies, we do have ICRA admins that take on larger employers that we can put you in contact with. Sometimes it makes sense to explore kind of a group plan at that phase. Um I think everybody like imagines the moment when they hit those like 50, 60 employees, just like, you know, we're all, you know, eventually gonna be millionaires, you know. So it's like you're you're always like imagining crossing that line. But in our opinion, I I think um I think the industry itself has really done a disservice to some of these smaller size businesses that might not sort of suddenly have a massive amount, like your your plumbers, your schools, your laundromats, your barbers, your like like the people who make living your life work, most of those aren't ever gonna have more than 50 employees. And there's no one really specifically working to try and make things easier for them.

SPEAKER_01:

Well, I see an importance in your voice. You seem to to really care about that situation. You know, you stated your mission is to make small business the best place to work. That's uh that's ambitious. Is does health benefits really uh work into that mission?

SPEAKER_03:

I so I think small businesses are the best place in the world to work. Um you tend to care about what you're doing, you tend to really like know your coworkers, you tend to be able to do interesting work that you couldn't in larger orgs that maybe are more defined or rigid with their roles, and hopefully you tend to be able to see the fruits of your labor when that works out. The rub is you do have to sacrifice a lot in order to work at a small business. Uh you don't get that big corporate HR team, you don't get, you know, on-site lunch, dinner, catered, whatever. Um, and a lot of times Brother Joe is doing all the work himself.

SPEAKER_00:

Yeah.

SPEAKER_03:

Yeah.

SPEAKER_00:

He's got to be the HR department, the hiring, the firing, he does all of it.

SPEAKER_03:

Yeah. And a lot of times you don't get the same healthcare options. And that can define whether or not you can work at a small business at all. We've helped small businesses recruit employees they've been working on getting at their business for years that they never had a shot at because they weren't able to take care of a chronic medical condition the employee had with the health benefits they were option offering. Like, I don't think health shouldn't constrain where somebody is able to work.

SPEAKER_01:

I am I agree with you 100%. For some of our small business owners right now listening who are frustrated with their current health benefits, what would you say that they should be thinking about or asking so that they can make a determination? Maybe this is a better idea to go to stretch dollar than who I'm with, or this is a really good deal and maybe I shouldn't leave. Like what information should they be gathering or saying or understanding that would set that line apart to say, you know what, stretch dollar is the right way to go, or you know what, guys, you're doing a really good job there. Don't, don't, don't let it go.

SPEAKER_00:

Hold on to that with two hands for right now.

SPEAKER_03:

Yeah. Well, I have yet to find somebody who was surprised they were offering health insurance their employees didn't like. Odds are you've heard about it. So there's a chance you know already if you're listening. But I think what's more interesting is those people who are like, maybe, maybe now's when I should try. Maybe now's when I can put something together, do an initial offering to the team and sort of see how it goes. And that's really our sweet spot. Um, talking with those people who are thinking about uh they might be ready to dip their toe in. And, you know, it's not always the right time. We can be very like transparent with people and be like, hey, you know, maybe this is something we revisit in a few months. There's we we sort of like to think it's more it's more of a when with stretch dollar than an if. Once you really understand how simple and easy it can be to do this, uh it's more of a timing question.

SPEAKER_01:

That's that's his pitch. Listen, I'm just letting you know, you you will be back. You will be back. So what what are the plans for the road ahead? I mean, you know, as we as we bring all this together, you know, and and kind of put our arms around it, and I really appreciate you being able to talk to us about that, you know, coming into the close, like you know, what yeah, and what honestly, like what have you learned too in the last couple years? Like, you know, every once in a while you get to get your butt kicked and go, I don't want to do that again. Yeah, but you know, as you've gone through this, I'm sure you there's been some growing cycles and some some things that you've learned, and now you're taking all that together. What do you see in the next few years? Where's stretched out are going? What do you what do you guys got?

SPEAKER_03:

Yeah, it's funny. Um a lot of times I think about this. Uh I saw this flag in like a machine shop once, and it says, it said, uh, we don't do this because it is easy, we do it because we thought it would be.

SPEAKER_00:

Um I like that.

SPEAKER_03:

And uh I'll be honest, I I thought we were gonna shoot out of a cannon, and then you know, it's funny. Uh I'm like, I can make this part of small business simpler, but I had to figure out payroll, I had to figure out hiring and all this stuff, and the first four hundred thousand dollars we spent was with lawyers to get planned documents drafted up, and it's been like it's uh we've definitely learned a ton. And I I think having come from the industry in some regards has been really helpful context as we design this because I've sold group policies, I've sold individual policies, I've I've helped hundreds, if not thousands, of people find health policies that work for them, and nothing's worked at this level, like nothing's been this easy to sell, nothing's been this easy to match people with. It's it's just different, and we're just really focused right now on helping as many people as we can understand that and try it out.

SPEAKER_01:

All right, so I'm gonna put you on the spot before we get out of here. It's your mic, it's your floor. What are you gonna tell the listeners that they need to do, how they need to do, what is the sales pitch for stretch dollar coming from the CEO, Marshall Darr?

SPEAKER_03:

Yeah, well, if you're beginning to think about your health benefits, I think we might have a simpler way to do it. Through StretchDollar, you can offer set pre-tax monthly funding that your employees use on policies they select and own themselves. Meaning you don't have to decide if you're offering Blue Cross, Blue Shield, or Cygna, or Oscar, or Ambetter. You only decide how much you can afford to offer. Our brokers will work with your employees to find the perfect policy, and it only costs you eight dollars per employee per month.

SPEAKER_01:

Wow, that's a pitch. All right, man, I like it. So if I wanted to do this and I wanted to reach out, how do we get a hold of Stretch Dollar?

SPEAKER_03:

Yeah, just go to stretchdollar.com. Uh, we'd love to chat. We'd love to help. If you're ready, you can go in and sign up within about 10 minutes right now.

SPEAKER_01:

Oh, what hey, listen, if you guys want to do it right now, we're gonna post up the the link at stretchdollar.com. That way you guys know where to go. Listen, I appreciate you guys listening. You know, we do everything rent to own here, and stretch dollar might actually stretch your dollar to give you guys some coverage and do some of the things that you need. I know one of my two three-store, five store owners, they just don't have that. And this is a great way to get your guys' coverage. So we appreciate you guys being here today. Make sure that you have any questions. You can also hit me up at the show, Pete at the rtoshowpodcast.com. Make sure you send me an email. Any questions, reach out to us. You can also go to the website at www.thertoshow podcast.com. You can go on there, see what the shenanigans I get into, and buy some swag, as we always love the swag. I got my man over here, Anthony, in the shirt. I love it, looks good. If you guys have any questions, please hit me up, but you can also follow us on Facebook, Instagram, LinkedIn, YouTube, where you're gonna see this. Hey man, Marshall Darr, CEO of Stretch Dollar. I really appreciate you taking out your time for us today. Cause I you know what? I have a lot of guys that ask me a lot of questions, and I'm gonna point them in your direction. We'll see if we can make this work. Thank you so much for being on today. Thank you, and and and tell Miss Melina I said hello. And hopefully you guys, uh, you know, the next time we talk, hopefully you guys are gonna be twice the size that you are now. Thank you. It was great. Great. I I wish you I wish you guys luck, and I would tell you guys as always, make sure you get your collections low to get your sales high. Have a great one.