Insurance, the Army & Michelle Obama with Jennifer Allain

On this week’s show, I talk to Army combat veteran and small business owner Jennifer Allain about the Affordable Care Act, what it was like to be a woman in the Army in the late ’90s, and how it feels when you get to represent your community at a Michelle Obama event. All that and more, here on Women Conquer Business.

Hello, and welcome to the Women Conquer Business podcast, featuring discussions with your host, Jen McFarland. Every week, I discuss a different aspect of building a business while balancing it with an incredibly busy life. I share experiences, successes, and failures, and answer questions submitted by you, the listener. Thanks for tuning in. Let’s get started.

Today’s episode consists of excerpts from a two and a half hour conversation between Jennifer and I. I picked out a few of my favorite moments as well as moments that will help you move your business forward, not only in terms of insurance but also how to get out in your community and reach your clients. Here’s a little more about Jennifer.

Jennifer Allain was born and raised in Florida and is currently a Wilsonville, Oregon resident. She’s a decorated combat veteran who served in Bosnia and Iraq, where she performed in positions related to her military police title. Prior to self-employment, she attended Florida Atlantic University in Boca Raton, where she majored in interdisciplinary studies with double minors in psychology and sociology. Florida is truly beautiful, but she loves the Pacific Northwest. Jennifer’s business, Insurance Coach, LLC, is a veteran- and women-owned small business and independent insurance broker that represents multiple Medicare, health insurance, and medical insurance providers in Oregon and Washington State. Jennifer is dedicated to pairing people with the right Medicare, health insurance, and medical insurance solution based on people’s needs. She strongly believes in gathering detailed information from each client before conducting research so she can present the best insurance options for each individual, family, or small business. The coaching aspect of the business includes insurance coverage education, motivation, and honest support in helping people find the best possible solutions for each client’s specific needs. Please welcome Jennifer Allain to the show.

So how does somebody who’s super funny, first of all, survive basic training without blowing your arms out from doing 7 billion push-ups from popping off to a sergeant–

I totally did. I totally did.

I can totally see that. How do you go from the Army to insurance?

So first off, I want to rewind a little bit and go back to high school, which is not something I say often. When I was I want to say a junior in high school, we switched from slow-pitch softball to fast-pitch softball.

Oh, God. That would have been terrible for me.

And it pretty much ended me in softball. To be fair, I was never that great at slow-pitch. I don’t even know if I would have gotten a college scholarship. Probably not. But it was what I was looking for. So when we switched to fast-pitch, I thought, “There’s absolutely no way I can survive this. So I’m going to go over, and I’m going to be on the weight-lifting team. And I’m just going to hang out with my buddies for my senior year and party.” And so I ended up being like 117 pounds, and I was able to do a little bit of lifting. So when I joined the Army, and I realized that I could do push-ups and those around me couldn’t, it actually became a culture, like a class system in our little basic training. Because if you piss me off, I can say some things, and we can do some push-ups. And it’s not going to hurt me. And I’ll just look at you the whole time and smile. And then when they say, “Recover,” and I yell, “Never!” And they turn around and go, “Okay, keep pushing.” I’ma look at you, and I’ma smile as we push. Right? And then when they left they’d come over, and threaten to beat me up, and things like this. And I’d never really been in a fight. So I was like, “Well, maybe. I don’t know.” I ended up actually in four altercations in basic training. It was fun. It was very eye-opening. You take 40 females of all different ages from all across the country, and put them in one room together, and tell them that that’s where they live, we gonna fight. We gonna fight.

That’s funny because we didn’t fight at the sorority.

Oh, really? Yeah.

Well, nothing with fists. Just lots of disagreements.

Well, the problem is, the disagreements, you couldn’t go to your corner. I would see you sitting right there talking shit. There’s no space. We’re all open. This is one big room. We’re all in it. So we’re over here at our thing and you’re over there with your thing. And the beauty of it, and I don’t know if this is something that other people experienced, is that towards the end of our training cycle– so we were not together for just 8 weeks, we were together 18 weeks.

Oh, my God.

I’ll explain that in a second. But towards the end of our 18 weeks, every single one of us, if I remember correctly, every single one of us that had beef, or issues, or didn’t like her because of this, or whatever, we did end up being close. We did recognize that it is us three or four basically females in this whole big man’s army that we’re about to go out into. And so by the end of the whole thing, we were kind of a united front. We were friends. We were not fighting at the end and things like this. So we did take that time to fight, and learn our place, and learn how to live together. But towards the end of our time together we did figure that out. And we did end up respecting each other. So I do remember that. When I got out of the military, I moved back to Florida. I went to south Florida to go to college. And while I was there I was lucky enough to get a job as a private investigator.

Oh, cool.

Yes. Absolutely. It was cool. It was something I never thought I’d be able to do. It was something my father told me that I would never be able to do. And as it turns out, I was pretty all right at it. I made some things happen. And I got some results that weren’t always expected. So I had a lot of fun doing that. And it wasn’t like, “Is he cheating on her?” It was a different echelon. It was people filing lawsuits. I can no longer do gardening. I can no longer maintain my yard. I’ll bet you right now. I’m going to pull up in front of your house with my large coffee, my foot-long sub, and back then my cigarettes. And I guarantee you I’m going to get a videotape of this son of a bitch gardening. That’s exactly what he’s going to be doing today. He’s not going to be watching TV. He’s not going to be nailing a nail into a piece of wood. He’s not working on his car. That exact same thing he said he could not do is exactly what I’m going to give you video of him doing if he’s lying.

I’ll tell you, people don’t realize how much insurance is PI work for the most part. My husband is also in insurance. Are you sure you’re not my husband? Oh, okay. Yeah. Good talk. Okay. Yeah. No, you’re not. All right. Okay. But he does all kinds of investigatory work when it comes to lawsuits and insurance.

There is not just one thing that I need to be good at. I need to be good at a lot of things. And the fact of the matter is I’m not I’m really good at just a few things, but I have a lot of resources. And people are resources. And the interwebs is resources. And that damn tree out front is a resource. Another thing I learned in the army is being a good leader is not about knowing everything it’s about knowing where to find it, and being an actual human being to somebody. Definitely not the definition of leadership that I was taught, [laughter] but that’s what I learned and what I took with me per se. But yeah, so moving up here, I was marketing myself as a private investigator. Hey, insurance company, hire me. I’ll go do the thing and I’ll work just for you. And here’s my track record and here’s how much I cost. And every person I saw was like, “Yeah. No, we need more agents, but I don’t know– we don’t really need this in this state. We don’t really have that much.” I said, “Okay. Well, what’s an agent do?” And they said “Oh, we sell insurance” and I said, “Sales. Bye [laughter].” No.

No.

Law enforcement investigations. That’s it. I was an MP in the army. I said, “Absolutely not.” Call somebody else.” And there was this one girl that I spoke with, well, she was a young lady and she said, “Listen, you got to come talk to Jim. Jim’s just like you. He’s funny and you’re going to love what he has to say. And what we do is really different and I think you’ll like it. It’s worked for a lot of people, bobbitty shmackity [laughter].” And so I said, “I need a job interview. It’s been a minute. Let me go talk to Jim.” And come to find– end of story. I got sold on the idea of working for yourself and the unlimited income potential and make all the money in the world and set your own hours and all those things. And I thought oh, I never really thought I could run my own business and come to find out I couldn’t [laughter].

But you do.

Yeah. At the time, I became a captive agent which means you work for somebody else–

Oh, okay.

–and you sell what they tell you to sell, and that was not a good mesh-up for me. And so I spent a couple of years like a ping-pong ball kind of moving from here to there, falling underneath others’ businesses and finally decided I just wanted to set up my own and that’s what I did in 2013 or ’14, something like that. And what I do now is I’m able to set my schedule and I’m able to control who I talk to and what I do for them and things like that, and it’s a big blessing. Yeah.

So you like it?

Oh my God. It’s amazing. It’s not the end-all-be-all for me. There’s definitely another chapter or two for me [laughter]. I’ve built a thing that I think is beautiful and it does not have my name on it for a reason. I want it to be like a Menudo, not a soup, but the group.

Not the soup. The group.

Indeed.

Yeah. A trademark.

No [laughter]. I want to hand it over to somebody and I want them to make it awesome in the time that it will serve them and then I want them to hand it off to somebody else, maybe to be a different kind of insurance. Maybe it’ll have a different focus. I don’t know. I don’t care. You send me a couple of bucks every month and go run this business and then when you’re done with it, pass it onto the next maybe veteran who needs a hand or whatever because I wasn’t getting hired. Nobody was going to hire me out here.

Really? Yeah. Now I [inaudible]

So I started my own business. You don’t want me, I’ll find my own house [laughter]. But it’s changed a lot now that Affordable Care Act. The Affordable Care Act, a huge reason that I’m still around and I’m still in the business. Absolutely. Prior to the Affordable Care Act, it was hard to be– almost impossible to set up one’s own shingle as an insurance broker. The Affordable Care Act encouraged insurance companies to give appointments to individual agents. By appointment, that means that there’s a contract between myself and insurance company that says, “I’m allowed to represent you in the following terms with the following training and the following certifications and insurance. We have an agreement that if someone talks to me or I talk to someone about your product, they sign up for your product, you will pay me X amount of dollars.” Not every insurance company wants every insurance agent representing them.

Okay, fair. Right?

Fair, but that makes it hard as a new insurance agent coming up, right? If I can only talk to you about one company, what good to you am I as a broker?

Okay, that makes sense.

And how could I even call myself a broker? Yeah, so it takes a while to go to every single carrier and say, “May I do this? May I do that?” and it’s not easy. And there’s other avenues out there that one can take but I wanted to go direct because I’d kissed some frogs and I just wanted to go direct with these carriers and learn from them what to do instead of having a middleman. So that’s what I did and over time, it’s been great. But the Affordable Care Act enabled me to set up a business that is not sales. I’m a liaison. I’m an educator. Some say edutainment and I’ll take that but, until recently, “You had to have health insurance, why would I sell you something you have to have?”

Right.

“You came to me, I didn’t come to you. You called me, I did not call you. But you called me, I put you on the calendar, you come in, I explain the Affordable Care Act as it pertains to you and answer any questions you have. I help you enroll in a plan, right? And then throughout the year, your questions, comments, concerns, moans, gripes, complaints, you call my cellphone number instead of 1-800 Peggy in Russia.” You know what I’m saying? And so I can help over the phone, or whatever, from there. So that’s the service that I’m able to provide to people and being able to explain things and say, “Listen, I grew up on a dirt road. I went to public school. Let me grab a crayon. I promise it’s not too complicated to understand. I promise that it’s going to take me five minutes to explain this to you and you’re going to feel like a genius. You’re going to forget what I have to say in three hours because we’re humans and that’s the way it works. But I’m going to make you dangerous enough in this time, here and now, to make an educated decision about your life. I don’t live your life. I don’t have to answer to your consequences, you do. So I want you to do right for you and that’s what we’re going to do. And I’m going to help you be smart enough to do right for you and hopefully, you’ll respect that enough to call me next year and we’ll do the same thing then too.”

That sounds cool.

But it pays well. The insurance company pays me but my clients never pay me. I get paid in handshakes and hugs.

Well, that’s awesome.

Yeah. There’s one couple that brings me a box of covered cherries– chocolate-covered cherries every year.

Yeah. That sound pretty awesome too.

There’s thank you cards all over my computer screens. I have two, so they’re [inaudible].

Yeah. So it sounds like you’ve found, definitely, a niche, right?

Absolutely. Absolutely. The work I do for individuals does not take as long as it might take for you to do on your own.

Right.

The work I do is minimal. Let’s be honest, I did Army work. I dug holes and slept in them. It takes me a couple minutes to do some Google searches and find out some things on the Interweb for you. That’s all I’m dong, right? As long as I get to the right resources, which I do, it’s fun. And I don’t always have the answers and sometimes, it is complicated. And I have people I can call. When it comes to other lines of business, I have people I can depend on for every single carrier. I sit on the shoulders of giants and I’m just twiddling my thumbs, having a great time. I’m a lucky girl.

Yeah, you are.

It’s like proof that nice people get good stuff.

Oh, dude. Absolutely. It’s out there. There is this duality in my head, all the bad things I’ve seen overseas and things I’ve experienced, and but then you come to Portland and you see people beaming with joy just because the sun’s out. Right? And being so kind to each other and all the merging, all the merging today. Listen there’s a lot of traffic but people are happy out there.

Because of the sun.

I think so.

Yeah.

You should have seen the line at Dutch Bros., It was around the corner.

Oh, I believe it.

It’s Monday. That’s crazy. So yeah, I’m reminded that there is an internal goodness in every single human. Every person is awesome. They’re just as awesome as they are poopy, and recognize that we see that.

Wow, poopy. I didn’t expect poopy.

You didn’t expect that?

No.

Yeah. I don’t think I did either.

I swear, I do too. I did a few minutes ago.

You did? Okay.

Yeah. Yeah. I don’t know. Maybe I thought it was colorful. Poopy.

I don’t know. That sounds like kind of like baby diaper.

Yeah. I’d say we’re half awesome and half baby diaper.

Yeah. That didn’t land as good for me. Yeah. I don’t know. That’s why poopy’s better than baby than baby diaper for sure.

Yeah.

Yeah.

You miss 100% of the shots you don’t take, so you got to take them.

Oh, God. That’s so true.

You got to take them [laughter].

So where else do you go to network? Do you really have to do any?

I don’t know if it’s unique to the industry. I don’t know if it’s unique to my business. But I am a one-person shop. I don’t advertise. I have a website but it’s Facebook, but I don’t have advertisements out there. A few clients have put me on this website called Next Door. Have you heard of the Next Door thing?

Yeah.

So there are pockets of Portland where I’m very popular amongst people that certain needs and I am very grateful for that.

I’m pretty proud of that actually. It started out with one person who just was like, “Yeah. I’m going to do this for you and see what comes up because I love you” and I was, “Oh, I love you too.” And one person calls and then another person calls and one person called me last week, she came into the office and I said, “How’d you hear about me?” because when she called me on the phone I said, “Who can I thank for having you call?” And she said, “Oh, a neighbor.” I said, “Okay. Great. Yeah. Okay.” I don’t push on the phone. No big deal. Came into the office, we chatted, towards the end and said, “By the way, I forgot to ask who sent you?” and she goes, “I found you on the Next Door website” and my heart just went pitter-patter, pitter-patter [laughter] because there’s a few people that I remember told me, “Hey, I’m going to say good things about you on there,” and so they must have. So there’s that. There is a place that I volunteer. There’s a neighborhood that I volunteer. I’m a driver for people that need someone to drive them to certain places. That organization has coffee once a week and I’m helping– I’m on the senior resource fair-planning committee so I’m going to help with that. Going to help get some resources and we’re going to have a senior resource fair. It’s going to be great. And yeah, I’m really excited about it. So I do a little bit of volunteering. People call me because they find me on the internet one of my favorite stories is this guy and his wife came in the office and– what happened? He said, “Oh, you ain’t going to believe this.” It’s towards the end. You know how guys say, “You’re not going to believe this.” [inaudible] stuck out his chest, you’re not going to believe this. I was talking to my neighbor the other day and we were kind of chatting over the fence there. And I said, “Hey, we’re going to go see somebody.” And he went in his house and came back out and handed him my business card. And he said, “Yeah, that’s the girl we’re going to go see.” So they both–

Which is awesome.

Right? Crazy town. So I was like, “Yes, yes, it’s working.”

It’s totally working. And it’s funny because I’ve had this contract– My big consulting contract right now is with the City of Portland. I’m helping women and people of color with small local businesses do their digital marketing. And the first few things that we talked to people about are; volunteer in your community, get on next door. I mean, all of the– almost to like to a tee, everything that you just described is like, the very first thing that you need to do in terms of reaching out to your community and getting business.

And you know, it’s unique because it’s probably about a half hour from my house.

Yeah, you’ve got like a circle and like–

Yeah, exactly. And this isn’t new. I knew when I first started in business, and when I was going to the classes, people say, “Go volunteer, go do this, go do that.” Yeah, whatever. You don’t have time for this, things like that. But it’s something that I enjoy. Don’t forget to do things that you love because if it sucks, you’re going to suck at it and nobody’s going to want your ass, and then you will be miserable because you suck.

I wouldn’t say go volunteer unless you want to volunteer.

Yeah, exactly.

You know what I mean?

Yeah, it’s finding something that you love. And for me, it took a while to find exactly where I fit in. I am 90% disabled, I can’t help the ex-president–

The peanut farmer.

Jimmy Carter.

Thank you.

You can’t do Habitat for Humanity.

I can’t help him build a house. I want to, but my life– it’ll hurt. So what can I do? And so I found this place where I can be a driver, and it’s this community that I love. And these people that I love, and I’m having a good time, and they like hanging out with me as much as I like hanging out with them. And, oh, by the way, I get to help with this insurance thing where you’re not paying me anything. I give you the same service that you would get from the internet, but better.

Because you don’t have to do all the work.

Exactly. I’m doing your insurance for you, but you don’t have to pay me, the company does. And that’s a great thing because I can help everybody. Doesn’t matter how much money you make. It’s the great equalizer. The idea behind the Affordable Care Act, and I don’t want to get too nerdy, but–

Too late.

The affordability in the Affordable Care Act was never meant to bring down the cost of health care in this country. Nobody was going to let “the black guy” do that. It wasn’t going to happen. So what he created, rather, what he knew was created on the East Coast was this thing where we could anticipate someone’s income tax return and then we can give them access to it. So basically, you can go to healthcare.gov and you can say, “I live here and make this much money. Here’s my kids. What do you think?” The system comes back and says, “Well, if everything you told us is true, we think that you’re going to qualify for X amount of dollars and income tax refund.” Now, you can do what you’ve been doing your whole life, which is pay for your health insurance, and maybe get that refund at the end of the year. Or you can be like Michael J. Fox, and reach into the future and access those projected income tax refund dollars on a monthly basis to help pay for your health insurance. So let’s say you qualify for a 1,200 dollar income tax refund. You take 1,200 dollars and you divided by 12 months in a year, it gives you $100 a month. So if the insurance policy you want is $400 a month, you can pay 300 and the IRS will pay the insurance company $100 a month in your name and then you have that awesome policy. You live throughout the year, you file your taxes, everything comes out in the wash.

I never knew it worked that way.

If the system comes down and says, ”You’re eligible for this much,” and you use it, but and so and so lives you 10 grand or you win a couple grand in a scratch-off card or whatever and you don’t report it, you don’t call your insurance agent, there’s a possibility that you wouldn’t qualify for that amount and you might have to pay some back at the end of the year. So that’s also something that I make sure people understand. This is a very beautiful thing but it can be very dangerous as well. Again, I don’t have to write that check at the end of the year. IRS ain’t coming after me, they’re coming after you. So you need to understand the decision you’re making here today, the pros and the cons. I have tissues, I have chocolate, I have a nerf gun. My office looks more like a therapist’s office than it does an insurance agent’s office.

Sound awesome.

It’s pretty fun. I like it. Yeah.

Yeah. Maybe I should do that around here. I don’t know.

I like this house. This place is cool.

Super fun, right?

Yeah. My office looks– we tried to make it look like a house. Like a living room, and we’ve got a proper kitchen in there and all our doors are open, and I’m a very lucky girl.

I try to keep all the doors open but we have to keep the dog out during the interview time.

He’s so cute, though.

Although, Booker has been known to show up during podcasts before [laughter].

He’s famous?

He’s kind of famous.

Puppy famous?

Puppy famous.

That’s cute. That’s cute.

So, yeah. I didn’t know– well, because we’re covered by my husband’s job. So I’ve never had to, knock on wood, I’ve never had to go through what you just described to really understand the IRS piece of it. That’s the part that’s always been the big mystery for me, is why any of it went to IRS in the first place.

That’s why.

But that’s why.

It’s intertwined with your taxes. So you can go there–

I knew it was but I didn’t know– the part you just described is the part that was the gap for me, was being able to go and estimate a refund and then use it to offset your health insurance cost. I didn’t know that was possible.
Yeah. Yeah. Now, it would not be possible– let’s say, in your situation, you’re covered by your husband’s employers. Let’s say you came to me and said, ”I don’t like my employer’s policy.” You would not have that option of looking at your income tax return and accessing those dollars. You may not. That’s law. Yeah. That’s something that a certain group of people who did not want to affordable care act to pass made sure happened.

Who could that be?

Yeah. Yeah. When they make a move, I hope they call me. It was definitely the Republicans. I don’t remember the name but I remember it happening. And I remember learning about it and I remember being like, ”Why don’t they just put the whole wall underneath the affordable care act?” And then a couple months ago, they did and I was like, ”Oh, shit. I’m sorry I ever asked it’s [laughter] one hell of a telenovela. American healthcare is one hell of a telenovela, and I am enthralled with watching it. I am a huge fan, and I am lucky because I have the VA. I’m lucky because I get to be on the outside looking in.

Bigly. You are completely correct.

Bigly.

Bigly. You are so bigly correct.

I love using that word inappropriately. It makes me feel good.

I don’t think there’s an appropriate use for it.

Yeah, because it doesn’t exist.

It doesn’t exist.

Yeah.

Yeah.

Yeah. Hamburder.

Yeah. Covfefe.

So sad.

Sad.

Yeah. I get to go see Michelle Obama tomorrow night though.

Dammit.

I know, dude.

Super jealous.

I’m so stoked. I might’ve made a little diamond when I said that [laughter]. I’m pretty excited.

Did you find some buds to go with?

So here’s the jam. Like I said, awesome humans at the gym. One of them is a veteran wife, and she won two tickets in a raffle, right? Was going to go see her back, I think, in January. That went–

Snowed out.

Right, right. My friend is out of town right now and could not go. She said, “I want you to have the tickets.”

That’s awesome.

I know. And then she made a post about like, “I’m thinking about painting my house. Will anyone help?” And I’m like, “No one needs to help. I’ll paint the thing myself. Give me a toothbrush. I’ll do it. Let’s go [laughter].” Not a problem. You gave me Michelle Obama tickets. I’m going to paint your– I will paint the shit out of your house, girl. Painted. Boom. Paint it hard.

Oh my God [laughter]. I’m going to paint it hard.

Paint it so hard. So there’s another friend of mine from the gym who’s actually an instructor, and she told me, she said, “Jen, I know you want to go, and even if I can only get one ticket, I’m going to give it to you.” And she really was about it, and so when I was offered the tickets, I was like, “Yeah. It’s got to be Beth.” We’re going to go, and we’re going to have a good time, so I’m really stoked. And so another thing that’s exciting is that I get to, in theory, speak at the podium that Michelle Obama’s going to speak on before she speaks on it.

Wait, what? How?

Dude. For reals. So there’s going to be– so I guess what they do at these jams is they go out to the local community and they say, “Give us some of your people who fit into this category of military veteran, community service, whatever.” And give them the opportunity. What did she say on the phone? I was so excited when the lady called me. I was like, “No. I’m totally talking to Michelle Obama’s person. I’m fine. I’m totally listening.” I wasn’t [laughter]. So I guess the lights are going to go down and Michelle Obama’s voice is going to come out, and she’s going to say something like, “Hey, Portland. What are you becoming?” And the lights are going to come on down on the stage, and we’re just going to come out one by one, and I’m just going to say, “My name’s Jennifer Lane. I’m a disabled combat veteran. I’m also a member of the LGBT community. I’ve been helping Oregonians connect with insurance that they can use, understand, and afford for the past seven years, and I’m becoming an agent of change.” And then hopefully maybe some people’ll laugh. I mean, not laugh, but clap. And then I’ll walk off, and the next person’ll come on, “Hi. My name is so-and-so. I’m this, that, and the other thing, and I’m becoming yadda yadda.” And then they’ll walk off, and then the next person. And then Michelle Obama. Oh my God. I’m so excited. I don’t know if I’m going to sleep tonight.

I wouldn’t.

I’m definitely going to need to work out so that I can [laughter] maintain my level of composureness.

Composureness?

That’s right.

I mean, it sounds like you’ve been practicing.

Well, from being in those networking groups every week. From holding leadership positions. From being in the army. From having to give classes at the last minute that didn’t exist until I made them up [laughter]. I’m all right in bullshittery.
In the bullshit.

I think I can be. I think I can pull it off. For something that short, we’ll see. I don’t know. I might get nervous and be like, “Hi, my name is Domino. I like sticks.” I don’t know. Who knows?

It’s still Michelle Obama.

I know [laughter].

I mean, either way.

[music] I hope you enjoyed today’s show. If you want to know what happened four hours after this conversation with Jennifer, please be sure to tune in next week. If you loved today’s show, please share it with a friend. Thanks for listening