#451 How To Stretch Your Dollar To Be A Cash Money Records Baller w/ Marshall Darr, CEO of StretchDollar
Marshall Darr is the CEO of Stretch Dollar - making health insurance simpler and more affordable for small businesses. Sweat Equity Podcast® hosts' Law Smith and Eric Readinger discuss entrepreneurship challenges, opportunities in the healthcare industry, and how StretchDollar.com is disrupting the status quo through a new HRA funding model. The conversation also touches on comedy, sports rivalries, and personal anecdotes. For small business owners seeking affordable benefits options, this episode provides valuable insights on healthcare reform.
Health insurance for small businesses. (4:08)
Entrepreneurship, startups, and branding challenges. (11:15)
Stretch dollar health benefits for small businesses. (14:51)
Episode sponsored
by ZUPYAK - The first search optimized AI writer. Zupyak.com → promo code → SWEAT
by SQUARESPACE website builder → https://squarespacecircleus.pxf.io/sweatequity
by CALL RAIL call tracking → https://bit.ly/sweatequitycallrail
by LINKEDIN PREMIUM - 2 months free! → https://bit.ly/sweatequity-linkedin-premium
by BLOOM.io → https://bloom.cello.so/aZBXRYS22rB
by OTTER.ai → https://otter.ai/referrals/AVPIT85N
---
Sweat Equity 🔗s
Hosts’ Eric Readinger & Law Smith 🔗s
---
#HealthInsurance #SmallBusiness #Entrepreneurship #HealthcareReform #AffordableCare #StretchDollar #HealthBenefits #ComedyPodcast #SweatEquityPodcast #HealthInsuranceForSmallBusiness #EmployeeBenefits #HRA #DisruptingHealthcare #StartupLife #ComedianInterview #PhiladelphiaComedy #SportsRivalry #PersonalFinance #InsuranceOptions #LowerMedicalCosts #HealthCareCosts #HealthCareStartup #EntrepreneurInterview
Health insurance, Small business, Entrepreneurship, Healthcare reform, Affordable care, Stretch dollar, Health benefits, Comedy podcast, Sweat equity podcast, Employee benefits, HRA, Disrupting healthcare, Startup life, Comedian interview, Philadelphia, Comedy, Sports rivalry, Personal finance, Insurance options, Lower medical costs, Healthcare costs, Healthcare startup, Entrepreneur interview, Dick pic, Spirit animal, God, French kiss, Hot dog, Sandwich, Cilantro
Law Smith Comedian Fractional CMO 0:00
Are we going?
Eric Readinger, Fractional CMO, Producer and Head Of Media 0:02
No?
Law Smith Comedian Fractional CMO 0:04
Well, this is a little bit of a different episode. I'm kind of barbecued at the moment. So that'll be fun for listeners to listen to. This is sweat equity podcast sponsored by his up Yahtzee up why a k.com promo code sweat for that AI content writer and I don't feel like doing the rest of the day. Oh it's called sweat
are listening to the sweat equity podcast? We were trying to do thing on the show with a little intro that Eric loves a couple lightning round question. Do you want you got the first one?
Eric Readinger, Fractional CMO, Producer and Head Of Media 1:15
What's your least favorite food?
Marshall Darr, CEO of StretchDollar 1:17
Least? I I got the soap cilantro thing? Which Oh, okay. Yeah. Which is not great. my fiance's Afro Latina and so it causes a lot.
Eric Readinger, Fractional CMO, Producer and Head Of Media 1:29
You're missing out?
Law Smith Comedian Fractional CMO 1:32
Is a hot dog of sandwich.
Unknown Speaker 1:33
I hate this one. I think it's a taco.
Eric Readinger, Fractional CMO, Producer and Head Of Media 1:38
All right. What do you got? Okay. Are we doing more than one? Yeah. Okay. What's the spirit animal?
Speaker 1 1:48
gibbon. You guys ever seen it? The monkeys with the real long arms? Oh, yeah. Yeah.
Law Smith Comedian Fractional CMO 1:54
Does God exist?
Unknown Speaker 1:57
Ah. I think probably.
Law Smith Comedian Fractional CMO 2:02
You got that one. You can read that. They're punching. Okay,
Eric Readinger, Fractional CMO, Producer and Head Of Media 2:04
read it at all. What? What's the first time you French kiss someone?
Speaker 1 2:12
I was, I think very teen. Okay. All right.
Law Smith Comedian Fractional CMO 2:17
All right. You got any other ones? No, I think we're good. go to karaoke song.
Speaker 1 2:26
And used to be remixed ignition. But we live in more complicated times these days.
Eric Readinger, Fractional CMO, Producer and Head Of Media 2:33
Yeah, probably a dance associated with
Law Smith Comedian Fractional CMO 2:35
lets you do a Flash Dance with P. You know,
Unknown Speaker 2:38
I have one. G two. What's your least favorite color?
Law Smith Comedian Fractional CMO 2:47
Do you do Brown? Probably? Well, I
Eric Readinger, Fractional CMO, Producer and Head Of Media 2:49
was gonna say more like oranges. Brown. Oh,
Law Smith Comedian Fractional CMO 2:53
forest green only to forest green. Doesn't go with anything. Yeah, kind of ruins green. Yeah. Green. We got two other questions for you. Did you listen to the show? Before coming?
Eric Readinger, Fractional CMO, Producer and Head Of Media 3:05
These are not lightning round. You can take your time on these. Thanks. I did. You did? I wrote them dad?
Law Smith Comedian Fractional CMO 3:11
And then what advice would you give your 13 year old self?
Speaker 1 3:17
Um, I would. I was thinking about this one. Because I listened to the show. It's a good question. I would give advice to my 13 year old self and just let him know that like, everybody feels a little anxious. Sometimes. I spent a lot of time as a pretty anxious kid. And like, for whatever reason, it was very frightening to me to even acknowledge that. And like as soon as like, you get a little older, you start going to therapy. Like, all of a sudden you can acknowledge like negative emotions you have as like, not all that, like frightening are consuming and then you just place them where they are and keep doing dope stuff.
Law Smith Comedian Fractional CMO 4:00
Well, you've earned yourself a plug, where can people find you? As they're listening? Or after the show? What? Stretch dollar.com Stretch
Speaker 1 4:11
dollar.com we simply say easiest way for anybody to handle health insurance and benefits.
Law Smith Comedian Fractional CMO 4:18
And tell us about stretch. dollar.com.
Marshall Darr, CEO of StretchDollar 4:22
Yeah. Well, I've spent the last decade working in trying to figure out how to get small businesses set up with health insurance, and it sets. The options out there are terrible, very expensive and complicated. And I think there's a better way to do it. What we built is effectively a funding tool. Instead, we're small employers can offer their employees tax free cash that the employees can then use to pay for health insurance plans they pick and we have brokers to help match people but it takes things from like 100 Our long process down to about 10 minutes. And it's effectively as simple as being like, hey, everybody gets $300 a month if you sign up through stretch jolly. We handle the rest.
Law Smith Comedian Fractional CMO 5:10
So not but it's not an FSA, right?
Speaker 1 5:14
It's a new type of HRA. Okay, which is like,
Eric Readinger, Fractional CMO, Producer and Head Of Media 5:21
which everybody stands for is at all time, all three of us. Health. recovery resources, restitution
Law Smith Comedian Fractional CMO 5:31
and renal. That's a medical word. Yeah. Okay. Yeah. Moving
Eric Readinger, Fractional CMO, Producer and Head Of Media 5:37
on now, because we all know it. Yeah, we don't move right on.
Law Smith Comedian Fractional CMO 5:43
So we're not good on the health insurance stuff. So explain. Oh, I thought that was obvious. These are the barriers. These, you know, there's large barriers, I feel like it's like your taxes. Words on, it's purposely confusing nowadays. Like it just became this, this Rubik's cube of swords, that it's like, yeah, you can navigate your way through it if you're professional and understand it. But most people don't have that kind of time to put to health insurance, which is something that should be simple, simple, or
Eric Readinger, Fractional CMO, Producer and Head Of Media 6:17
at least, where you're going to have a guy. What
Law Smith Comedian Fractional CMO 6:20
So explain why it sounds like you want to be disrupter in this business, you see an opportunity, because it is so convoluted. Is that fair to say? Do you see this as an opportunity as a business? Well, yeah,
Speaker 1 6:34
and first of all, there's a very normal way to feel about it. I, the reason why I work in health insurance is because I hate it. It's too complicated and too expensive and too boring. Actually, like, what, when I realized I had ADHD, it was when I was initially studying for my health insurance broker exam, just because it's so dense, of materials. And I think that sort of like, robs people of a lot of ways to take care of themselves. Because like, if you have health insurance theory, things that just come with it, like, most of the time, you can see a dietitian three times a year for free. But almost no one knows that. So no one does that. Like in my perfect world, we can match everybody with a health insurance plan that actually pays more for their health care when they pay their health insurance company. Like I want. I want people to get things out of this expense that has just been like, so boring and annoying that people like refuse to engage with it at all. justifiably.
Eric Readinger, Fractional CMO, Producer and Head Of Media 7:41
It's like the worst savings account ever. But you're saying maybe throw some massages in there? Yeah, well, therapy, you know, whoa. Therapy first, was no right to the massage. I was the first one. Maybe it's the same person is that notice I didn't say man or woman? Does this
Law Smith Comedian Fractional CMO 8:00
FSA have a jack shack premium on it? Or what? Right?
Unknown Speaker 8:06
Out of that question? Record.
Law Smith Comedian Fractional CMO 8:09
We'll fix that in post. Well, AI, then. We vary a lot of post production on this show. What, you know, Eric's grossness aside. Well, I mean, why what's the biggest struggle to get a lot of small businesses to get on board with this? Just they don't even know about this existing? Yeah, it is a better example of the dietitian. Yeah,
Speaker 1 8:39
so like, like, legally, this only became an option back in 2020. And so
Law Smith Comedian Fractional CMO 8:45
it's Trump, Trump, Trump or Trump family here?
Speaker 1 8:49
Yeah, well, honestly. And like, and then, ironically, Biden went through and actually ratified it. So it's one of the few things that seems like we all agree on.
Law Smith Comedian Fractional CMO 9:02
Is all confused now. No, no, Biden, is Trump's great idea made it made it work. You know, he had to.
Speaker 1 9:10
Yeah. And so it's new, a lot of small businesses don't know about this. A million fewer small businesses in the US right now offer health benefits than did in 2010. And so a lot of people right now are just confused about how to get started. I don't think it's because people don't want to take care of their employees, I think because it's, it's because it's too expensive and too complicated. And like, we're here to try and provide a real simple way for everybody who wants to to get started.
Law Smith Comedian Fractional CMO 9:43
Yeah, I mean, it's when when you don't have benefits, it's never, that part's always it's never like set by the employer. Hey, here's what's going on. Right. It's just seen as we're not giving benefits, and then thus you don't care. are on the employee level. You know, it's like, I,
Eric Readinger, Fractional CMO, Producer and Head Of Media 10:06
I this is the overarching, like pain in the ass problem stuff where it's like, you can go, you can go into like, oh, well, if you don't have insurance, it's gonna cost you $10,000 Oh, well then no. And there's a problem there. Why is it costing $10,000 and just go down that rabbit hole, or
Law Smith Comedian Fractional CMO 10:22
you get even like a supplemental thing like good RX, and you're like, cool. How's that? We have taken that. Okay, cool.
Eric Readinger, Fractional CMO, Producer and Head Of Media 10:31
Well, are they do the flip side over there? Like you have a good RX card? No. Okay. Well, we'll just use the one that we have sitting on the counter here all the time. We get a lot of points for that. Okay, new I guess I don't know why you just don't
Law Smith Comedian Fractional CMO 10:41
know. Yeah. 711 employees do that too. They're like, you
Eric Readinger, Fractional CMO, Producer and Head Of Media 10:45
know, they're putting their own phone number. I
Law Smith Comedian Fractional CMO 10:46
know shit. I know. The racking up. It's like they're getting all the camel, camel. Camel cash? The. So how did you find your way into this? You were? You know, it looks like you were at gussto, which I thought as far as I could tell, it was a very good kind of idea for small businesses to kind of simplify it and a Turbo Tax gonna lay. Yeah. So tell us how you got to where you are right now with all of this? Yeah,
Speaker 1 11:14
it's funny. I kind of crash landed at gussto because I tried to start a company when I was 25. That didn't work for all the reasons 25 year olds starting companies tend to not be able to wait,
Law Smith Comedian Fractional CMO 11:27
don't don't gloss over that. What was the what was?
Speaker 1 11:33
Um, well, so I found these investors that really wanted to invest in a particular type of company and just kept pitching them until they give me some money. But then I had to build the company. And it was like a real estate agent, Assistant application, I didn't know anything about real estate or building a company or doing anything. So we got a few clients, but like, it was just us running around behind the scenes, there wasn't any technology. And so it was really hard to scale out but spent like a year working on that. Splitting a studio four ways in San Francisco with a few buds. And I like my co founder and a lead investor, one of having a falling out on Cinco de Mayo. I think over a few drinks and amateur Oh, yeah. So all of the sudden our funding was pulled. And I had I think $500 Total at that point. So I just started applying everywhere, and then wound up getting a job at gusto. Because the hiring manager thought my cover letter was funny. I started cool. Yeah, I kicked it off with Dear Mr. And Mrs. gusto. And
Law Smith Comedian Fractional CMO 12:54
that's pretty good. But you know, yeah. And you wrote one, I feel like you have to tip like, I never I didn't know people read them. Yeah, I thought they just wanted to see if you did it.
Speaker 1 13:10
Yeah, yeah. I wanna be epic. So great payroll platform for small businesses. From there, I met somebody who started a company called decent, which was trying to be an in health insurance company, a startup out of Austin. That didn't quite work. They still working on it, but bad name and people there and left decent HR. So everything's kind of connected.
Law Smith Comedian Fractional CMO 13:34
Yeah, yeah. Well, every every entrepreneur has kind of a windy road to where they get to. And, you know, decent though. That's a just a horrendous name for it. I don't want I don't want health insurance. anything close to be decent? Yeah. I don't want to think about that. If I get a rabies shot, I don't want to think you know, I got the decent rabies shot. Yeah. Yeah,
Speaker 1 14:01
I mean, it was that was not the easiest brand name to work with. Back in the day. I ran sales. It's
Law Smith Comedian Fractional CMO 14:08
like low self esteem in the name stesen Yeah, decent. Like you just got that's a c minus like, he just got through. I think decent was it
Eric Readinger, Fractional CMO, Producer and Head Of Media 14:19
was like a play on words.
Speaker 1 14:21
I do sat decent.com Yeah, decent advice.
Eric Readinger, Fractional CMO, Producer and Head Of Media 14:28
I don't know. And synth is part of her that's money.
Speaker 1 14:32
can be can be for some reason. People would always pronounce it like descent. Like going down that's even worse.
Law Smith Comedian Fractional CMO 14:41
We regret Yeah.
Unknown Speaker 14:45
But stretch I that's memorable. That's
Eric Readinger, Fractional CMO, Producer and Head Of Media 14:47
that scissor. That's a positive image.
Law Smith Comedian Fractional CMO 14:51
Yeah. So what's Where are you at with stretch dollar now? How long has it been around? We're where are you? As far as You know, you're coming on here for a purpose to promote stretch dollar. What Yeah. What do we need to know? What do people need to know out there?
Speaker 1 15:09
Yeah, absolutely. So we launched, we became our own face customer. And back in October of this year, we sort of incorporated the company in April, launched for everybody really in November. We're up to around 50 companies on the platform and growing pretty quickly. And yeah, I think if you've been thinking about giving your team some sort of health benefits, there's a good chance it'll be less annoying and cheaper if you get stretched taller than anywhere else. So we'd love to talk to you.
Law Smith Comedian Fractional CMO 15:44
Well, employee size, what are we talking about? Who's who
Eric Readinger, Fractional CMO, Producer and Head Of Media 15:49
should be paying attention right now.
Speaker 1 15:51
So we exclusively work with people with fewer than 50 employees. Most of our employees have. Most of our employees have fewer than 10. So really, like the small businesses out there, and we get we got a whole range. We have some tech startups. We got a horse farm out of Dallas Fort Worth. Shower, Dorian Soller, and like real estate investment funds. It's really anyone. Okay.
Law Smith Comedian Fractional CMO 16:16
You got anything else?
Eric Readinger, Fractional CMO, Producer and Head Of Media 16:17
We have this our door guy? Yeah, my shower door. Keith. Yeah. Oh, you remember Keith Dobbin? Yeah. Oh, wow,
Law Smith Comedian Fractional CMO 16:26
I send them sexy pictures. Different behind shower doors. Of course the
Eric Readinger, Fractional CMO, Producer and Head Of Media 16:31
same guy, right? Yeah.
Law Smith Comedian Fractional CMO 16:34
This is a comedy show. Allegedly. I do that. You know, I was on stage last night. How'd that go? And I talked about never sending a dick pic in my life. And a lady in the audience, I guess follows my Instagram was like, I've seen it. And I was like, what? Let it she's a regular at this show. And I was just like, No, you haven't. I've never done it. I swear. I've never set one I don't want above anybody
Eric Readinger, Fractional CMO, Producer and Head Of Media 16:59
talking about the angle you take on all your Facebook posts when you're walking. Oh,
Law Smith Comedian Fractional CMO 17:03
that's just hot smoke. That's fine.
Eric Readinger, Fractional CMO, Producer and Head Of Media 17:06
As I was talking about?
Law Smith Comedian Fractional CMO 17:08
I don't know. Yeah, I think so. But I was just like, well, now it sounds like I'm a complete liar if you blurt it out. Yeah. Yes, I
Eric Readinger, Fractional CMO, Producer and Head Of Media 17:16
see it. I would have second it down.
Law Smith Comedian Fractional CMO 17:20
On the Download with your guy right next to you. It was weird. Anyway, I just wanted to tell that story. Oh, that Oh, that was that.
Eric Readinger, Fractional CMO, Producer and Head Of Media 17:27
I thought that you were in terrible. Oh, cut that out and post the joke though.
Law Smith Comedian Fractional CMO 17:31
I don't even remember. Oh, I'm dating a girl that has touched the tissue addict. Now she's got to touch it the tourism. And I said jokingly, I'm no for real. I believe you. Yeah. And I'm gonna go as a joke. I said, I'm gonna send you a dick pic. I've never sent one. But I'm going to send them one to you kind of just like that. And then she goes, you send me a gig. I send you one right back, like, laser fast. And I was like, Oh, my God. I hope a train comes by and she gets distracted. I'll send it. Anyway, back to this. I don't know. I don't have any more questions.
Speaker 1 18:12
Yeah, I mean, it's a pretty, pretty simple, simple thing. Big pink sands stretch dollar easy. Yeah.
Law Smith Comedian Fractional CMO 18:20
Well, yeah.
Eric Readinger, Fractional CMO, Producer and Head Of Media 18:21
We'll separate that for the SEO and whatnot. Yeah, we'll make sure
Law Smith Comedian Fractional CMO 18:24
we hook you up with the video of this. Yeah.
Unknown Speaker 18:30
That sound bite, I'll get in trouble.
Eric Readinger, Fractional CMO, Producer and Head Of Media 18:33
How's the UX UI for stretch dollar? I would rate that. Oh, my
Law Smith Comedian Fractional CMO 18:37
God, you've run out of questions. How's the UX UI? You just said I'm out of questions. I am I got nothing. Some days ago, some days you don't help go doing the job for you. Most people listen to your audio. He's
Speaker 1 18:53
He's He's a cool thing about how it works. So employers give you money into your account to offset the cost of your health insurance premiums. So like for me, I live in Philly. I'm on a plan out here. It's around $400 a month. I pay for it on my credit card. The money from my employer, which is myself, but you know, it's
Law Smith Comedian Fractional CMO 19:15
you gotta be you gotta be a member. Yeah, yeah.
Speaker 1 19:18
goes right into my bank account. So I just get a couple of $100 of Free Credit Card Points a month. And like, stack it up. That's a vacation.
Law Smith Comedian Fractional CMO 19:27
Yeah. Philly. I was booed you were in Tampa as
Eric Readinger, Fractional CMO, Producer and Head Of Media 19:34
we you know, special sports. History.
Law Smith Comedian Fractional CMO 19:38
I hadn't still mad at Fat Joe Blanton in 2008 hitting a homerun in the World Series. That picture. Yeah.
Eric Readinger, Fractional CMO, Producer and Head Of Media 19:46
forgot about it. Yeah, I had made that out of there. I almost turn now it's back.
Law Smith Comedian Fractional CMO 19:51
I threw remote. nomos broke a huge big screen that was a mine.
Eric Readinger, Fractional CMO, Producer and Head Of Media 19:56
I think my most hatred was from the flyers lightning Eastern Conference Final the first year they won the cup you remember that? Oh fertile It was intense I just remember like I hate everything yeah if you feel it but Philly
Law Smith Comedian Fractional CMO 20:10
comedy scenes having a renaissance there's so many dudes coming out of there.
Speaker 1 20:16
Good to hear the whole whole city is filling is thriving. Except for like the back half of the eagle season. sacrament things again, which will play in the playoffs. I forgot
Law Smith Comedian Fractional CMO 20:34
I don't know. I got nothing. We don't have to make these longer than we got the point across. I think we're all tired.
Eric Readinger, Fractional CMO, Producer and Head Of Media 20:41
Yeah, I'm pretty tired. You don't understand. I had a long day of school that crazy energy with these kids and swear it was like everybody would fight each other. Eric runs a
Law Smith Comedian Fractional CMO 20:51
cult of part time of it's an A compound. It's not that P E.
Speaker 1 20:56
I hear those are tiring. So it's just
Eric Readinger, Fractional CMO, Producer and Head Of Media 21:03
energy suck. 9000
Law Smith Comedian Fractional CMO 21:07
What's that you actually lie like? That's when I know we're done. All right. Thanks for coming on. Appreciate it. Thanks. I'll just leave. So yeah, to see it. Sometimes they're good sometimes. You know,
Eric Readinger, Fractional CMO, Producer and Head Of Media 21:25
we're not good. No, I'm still recording. That's fine.
Law Smith Comedian Fractional CMO 21:29
That's how we close it out. A little button on the end of this one.
Eric Readinger, Fractional CMO, Producer and Head Of Media 21:34
We were both equally bad for the record. If that's what you're talking about.
Law Smith Comedian Fractional CMO 21:39
You're a lot worse. Oh, really?
Eric Readinger, Fractional CMO, Producer and Head Of Media 21:41
Let's we're gonna pull the scoreboard out.
Law Smith Comedian Fractional CMO 21:45
Bring it out, bro. I ain't scared. I'm gonna go read it. You're talking.
Eric Readinger, Fractional CMO, Producer and Head Of Media 21:48
I'm out of questions. Okay, well, I guess I'll come up with something on the fly. You're welcome. Yeah. Oh, oh. Am I'm just gonna stop recording whenever I want to. You don't get the last word.
