Military Grit, Entrepreneur Spirit: Kassie Kennaugh’s Story of Fear, Freedom & Financial Breakthrough

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Speaker 2 I came from nothing. We had to do some crazy things to be able to pay bills.
You don't get paid worth a damn in the military.

Speaker 2 I got a call for an insurance company and I was like, I don't want to do insurance. It was the only interview that I got back out of all the submissions.
Kim and I had a two-hour interview.

Speaker 2 I had originally went in for a sales job. By the time I left, I was office manager and I had negotiated a significant pay increase from what was posted.
And I started running the business.

Speaker 2 We went from a 60% retention to a 90% in less than six months. And he came to me and he goes, What are you doing? What do you mean? What are you doing? Stop making me money.
Make yourself money.

Speaker 2 And I laughed at him. He's like, No, I'm serious.
What's holding you back? Fear. I'm not good enough.
I don't know what I'm doing.

Speaker 2 And he goes, When are you going to stop letting fear dictate your future?

Speaker 1 Guys, welcome back to the level up podcast. This is Paul Alex.
We're currently ranked number one in categories, in all categories, and number one in business because of you guys.

Speaker 1 Thank you for the 4 million downloads last month. This month we are shooting to 5 million.
All right, Amelia, we're going to make it happen, right?

Speaker 1 That's right. All right, with that being said, we have another phenomenal guest at the level up where we're going to be talking about growth, okay? Growth is the key needle mover for this story.

Speaker 1 And you guys are going to love this. She's a president and owner of an insurance company for the past 14 years.
This insurance company is massive, by the way. Okay.

Speaker 1 So you guys are going to love this for all my insurance gurus out there. You guys are probably tuning in like, who's this? All right.
But we're going to educate you and entertain you guys.

Speaker 1 She also has a phenomenal podcast where she talks about growth overcoming critical incidents. And also, she's from the military.
We loved military folks. Okay.
Thank you for your service.

Speaker 1 Air Force for 12 years. But she's also going to be talking about bad relationships, motherhood, and how you guys can overcome this with your limiting beliefs.
That's what it's about.

Speaker 1 It's about leveling up. Welcome to the show.

Speaker 2 Thank you for having me. I'm so excited.

Speaker 1 I'm excited too. It's going to be good.

Speaker 2 It is. It's going to be fantastic.

Speaker 1 So, for the people that don't know you,

Speaker 1 who are you?

Speaker 2 And give us a little bit of a preview and your background uh my name is cassie kenna and i am prior military like you said uh 12 and a half years cop i was also a firefighter um i'm a mother of four beautiful children and um now i and i had an insurance company that i actually grew i sold and now i'm the president of an insurance company so um It's it's been quite a quite a journey for me.

Speaker 1 Quite a journey. Yeah.
So let's talk about it.

Speaker 1 right now you've been in the insurance game for 14 years on and off yep on and off and we'll start off we'll start off with that because everybody knows insurance right so what would you say would make somebody

Speaker 1 be great in insurance

Speaker 2 you have to so here's where we're going to talk a little bit about changing the insurance game. Okay.
You can be a great salesman all day long. Yeah.
Right. And you can sell cars.

Speaker 2 You can sell ice to an Eskimo.

Speaker 2 Any great salesman can. The point for insurance is teaching people and having a relationship.
That's a good insurance salesman, right? Because really, you're not selling anything.

Speaker 2 You're just creating relationships. That's how I built my agency.

Speaker 2 You teach people that they matter and not their money.

Speaker 2 That's the difference.

Speaker 2 So if you really, you know, if you're in insurance right now and you're trying to figure out how to change your game,

Speaker 2 how to grow, how to scale, change your outlook on what insurance is. That's what I would tell people.
I tell my team that right now.

Speaker 2 Every little guy counts, right? Every little guy counts. And so you're helping that person.
Are you helping them put money back into their pocket?

Speaker 2 Are you helping them actually have like that education piece of, hey, I know I'm insured. Now we have confidence.
You're building confidence. You're building that relationship.

Speaker 2 And now they're going to go talk to other people and be like, who's your insurance person? Do you talk to them? Do you know their name?

Speaker 2 Did they know your name? Like, that's a huge thing. Do they know your kids? Yeah.

Speaker 2 In my old business, I had 2,723 clients. Wow.
Wow. And I knew them all.
Yeah.

Speaker 1 I mean, that's the way it's supposed to be. I feel like, you know, as I start hiring younger and younger folks coming into sales.

Speaker 2 You're just saying that we're old. Come on.

Speaker 1 We're old school millennials.

Speaker 2 That's right. Yeah.

Speaker 1 We're old school millennials. We're the best.
Okay.

Speaker 1 But when it comes down to it,

Speaker 1 we're so used to talking to people in person like this.

Speaker 2 Yeah. Right.
Being relatable. They don't know how to do it anymore.

Speaker 1 Being able to go ahead and extract information. Yeah.
Right. Getting to really get to know someone.
I think that's key behind sales, soft skills, right?

Speaker 2 It is. Yeah.

Speaker 1 Yeah. So

Speaker 1 I resonate with everything that you said, but Do you believe that

Speaker 1 your background in the military actually helped you become a successful entrepreneur?

Speaker 2 Oh my gosh. I am so glad you asked.
Yes, because it taught me perseverance.

Speaker 2 You know, entrepreneurship is not easy.

Speaker 1 No, it's not.

Speaker 2 It is like, I mean, you have gray hair. We all know why.
You're an entrepreneur, right?

Speaker 1 Well, I got it when I was a cop.

Speaker 1 Let's be real.

Speaker 2 Mine's from the kids. But no, being an entrepreneur, you have to be able to persevere.
You got to adapt and overcome. You have to think outside of the box, right?

Speaker 2 There, you know, you do have to follow orders, but what is that order and who's making those orders?

Speaker 2 Are you now giving them?

Speaker 2 And so

Speaker 2 for me, being in the military taught me how to not take things personal, how to adapt and overcome, how to push, how to grow. The outlook is completely different.

Speaker 2 Prior to the military, I was

Speaker 2 very meek.

Speaker 2 I was destroyed emotionally and mentally, you know, and the military brought that confident woman out. Yeah.

Speaker 2 And there's a friend that we were talking to last night, and they said, you know, you have this huge barrier. You have this wall.
You have this shield. Part of that was built in the military.
Yeah.

Speaker 2 You know, I'm shielding myself and I'm protecting myself. And as an entrepreneur, that's what you're doing.
You're protecting what's yours because you're proud. Right.
Right.

Speaker 2 And you have to be able to take that shield and let it down at times when you're an entrepreneur to be able to to grab those people and bring them in right um but it's hard yeah you know military the military teaches you to be tough

Speaker 1 yeah but but you know what in the military it shows you how to be disciplined be a leader yeah you know be able to build relationships why

Speaker 1 Because it's needed. It's the fundamentals when it comes to life, right? To actually being an active human being in this organization or in this world, productive.

Speaker 2 Productive human being. Yes.
Yeah.

Speaker 1 So when did you start? When did you actually get into the military?

Speaker 2 So I went in the military at age 19. Oh, wow, right off the gate.
Well, kind of. So

Speaker 2 I traveled. I was an exchange student.
So my senior year of high school, I graduated in another country. I came back.
Whereabouts? Brazil.

Speaker 1 Why, Brazil?

Speaker 2 That's where they sent me. I'm so glad they did.

Speaker 1 You were basically voluntold.

Speaker 2 Yeah. Yes.

Speaker 2 exactly. Yeah.
So again,

Speaker 2 I loved it though. So part of that actually helped the military because I had to learn how to adapt and overcome at the age of 17.
Yeah.

Speaker 2 Because I didn't speak the language, I didn't know the people, and I had to learn how to trust unconditionally because I'm walking into somebody else's home and they are raising me for a year.

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Speaker 1 Imagine a credit card with rewards that can grow in value. With a Gemini credit card, you can earn Bitcoin or one of over 50 other cryptos instantly with no annual fee.

Speaker 1 Every swipe at the store or gas pump earns you instant rewards deposited straight to your account. Plus, sign up now for a $200 Bitcoin bonus to kickstart your rewards.

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Speaker 1 That's pipe drive.com forward slash level up, and you can be up and running within minutes. No, absolutely.
And then you probably stand out like

Speaker 1 no other. Oh, probably like, wait a minute.

Speaker 2 One thousand. Yeah, who is this? Yeah.
You know? Sorry, blonde hair, blue eyes in Brazil. Yeah, yeah.

Speaker 2 So that happens.

Speaker 1 Yep. And then how do you get into the military?

Speaker 2 So I came back. My brother and I actually tried to enlist at the same time together.
So my younger brother, and we were going to go Marines. Okay.

Speaker 2 The Marine recruiter, I know. Give me the look now.
I chose better. Okay.
Love it. No.

Speaker 2 But the Marine recruiter looked at me and he laughed.

Speaker 2 And he said,

Speaker 2 I think it's great that you want to do this,

Speaker 2 but physically you're never going to be able to because I was 300 pounds. Wow.
So when I went to Brazil, I gained 150 pounds. Good food.
Oh, my gosh. That and alcohol was biggest thing.

Speaker 2 Told them that last night at dinner. I was like, guys.
So,

Speaker 2 and they can drink at 18. Yeah.
Yeah. Yeah.

Speaker 2 So I came back and I'm like, what am I going to do? I want to join the military. This is, this is my way out.
Right. Right.
I don't want to be here anymore.

Speaker 2 I, and that's because of past trauma, right?

Speaker 1 And where, and where was here?

Speaker 2 Michigan. Michigan.
Yep. Yep.
So my hometown.

Speaker 2 And so the Marine was like, yeah, sorry. The Air Force recruiter, and this is part of the reason I joined the Air Force, he looked at me and he said, do you really want to join?

Speaker 2 Yeah, I do.

Speaker 2 Then go do it. Yeah.
Why not? So I did. So at 18, from the age of 18 to 19, I lost 150 pounds.

Speaker 1 How'd you do it? What's the secret?

Speaker 2 Chicken.

Speaker 1 Most people are very like, what?

Speaker 2 I eat chicken all day, every day.

Speaker 1 But guys, here's the thing

Speaker 1 that she's not telling you. It has to be portions, okay? That's where I made the mistake.

Speaker 2 Well, portions and then the job that I had, I had to, you can choice. And you'll hear me talk about that a lot in my podcasts and just speaking.
It's choice. You had an elevator and you got steps.

Speaker 2 Which one are you going to choose? I chose steps because that was one way, along with my chicken, that was going to help get rid of the weight. And so that's what I did.

Speaker 2 I ate a ton of chicken, took out all sugars, stopped drinking sodas, and I pushed forward. And yeah, and so I did.
I lost 150 pounds. I joined.

Speaker 2 And then, yeah, I was number one. I graduated number one.

Speaker 2 academically.

Speaker 2 I don't know what you guys call it, but it was dorm chief. So we, you know, number one there.
And then physically,

Speaker 2 I was literally number one.

Speaker 2 And no one,

Speaker 2 not even my parents, believed that that was something that was capable.

Speaker 1 Wow. And why do you think that?

Speaker 2 So my parents didn't know what happened to me, right? So I was raped in school. I was drugged and raped.
Wow. And as a joke.
And

Speaker 2 they didn't know. I held a lot of that from them.
So I had. a lot of pain.
It is a lot of pain. Yeah.
And so I held that from them. I held my eating disorder.
Yeah.

Speaker 2 I, there's a lot of depression, a lot of anxiety. The drinking, I drank a lot.
Right.

Speaker 2 And so

Speaker 2 they had no idea. Yeah.
And so

Speaker 2 they see a girl who is their only daughter who is required by statue to

Speaker 2 prove herself. Like you have to get good grades.
You have to be great at softball. You have to be great at at hockey.
Like, there's no option. Right.

Speaker 2 Well, for me, that's a lot of pressure on a child to be perfect. Like, let me hold you on this pedestal.
I don't want to be on that pedestal.

Speaker 2 That's where the eating came in and the drinking and so on. And so, when I went into the military, I was leaving for MEPS, and I love my parents.
We have an amazing relationship.

Speaker 2 My parents looked at me and they're like, We really hope that you make it, but if not, we'll see in a few weeks.

Speaker 2 So, it was already

Speaker 2 the doubt of you're not gonna make it, yeah,

Speaker 2 destroyed me.

Speaker 2 So, what happened for eight weeks?

Speaker 2 I was focused. Like, I got yelled and screamed at, I got talked down to.
I mean, I don't know how many times my face hit that pavement, yeah, and I just pushed through.

Speaker 2 And

Speaker 2 they didn't make it for my graduation,

Speaker 2 And

Speaker 2 that for me was a sign of

Speaker 2 I'm alone.

Speaker 2 I'm going to have to push through this world by myself. Yeah.

Speaker 2 And as an entrepreneur, I still kind of have that mindset of like, this is me. This is, this is my baby.
This is my livelihood. This is

Speaker 2 nobody is going to take away my entrepreneurship. Right.

Speaker 2 So,

Speaker 2 yeah, it, there's a lot, you know.

Speaker 1 Yeah, that's um, that's that's hard. I feel like you know, a lot of people they get into situations, specific situations in life, and they just let it consume them for years.

Speaker 1 You had a situation happen to you, and you essentially took that pain and you made it productive, right?

Speaker 1 Even your parents not believing in you, right?

Speaker 1 I always tell people this: this is like, if you have people around you that don't believe in you, extract yourself away from that environment so I think what had happened for you

Speaker 1 God put you on the path of hey I'm gonna take you out of this environment because there's no one there supporting you

Speaker 1 and they put you in a supportive environment like the military right it's a military uh it's built on more teamwork yeah you know getting it done together yep right we have a one of my nutrition fitness guys out here in the hallway amazing by the way planning mike big mike he's a big teddy bear big mike is great guys yeah he's great and but but he's big on team yeah huge on team he's just like dude i just want to be there i was just like all right you know let's do it yeah

Speaker 1 so so i uh i've worked with a lot of military folks you know being my time in law enforcement and i think it's great i think that uh it's

Speaker 1 big needle mover the fact that you've expressed that on this podcast because there's gonna be a lot of people that listen to this and they've been in bad situations and they just do not have a support system.

Speaker 1 And I think it's very important. I think it's very important to talk about it.
You know, towards the last two years of my law enforcement journey, I fell into deep depression

Speaker 1 over some BS now that I think about it. But still, it just, it piles up, right?

Speaker 1 And then on top of that, you could go to my mom, who, you know, I always consider my best friend, even though we bump heads all the time.

Speaker 2 That's a best friend. Yeah, that's a best friend.

Speaker 2 Best friend. They're going to tell you what you don't want to hear.

Speaker 1 Exactly. And she tells me that.
She's like, you know,

Speaker 1 you might get mad at me, but it's because i tell you the truth yep no one else will tell you the truth paul yeah everybody always wants to kiss your butt and i'm like yeah sure mom

Speaker 2 but

Speaker 1 when i went to her back when i felt in deep depression i told mom i'm depressed like this is not cool like i don't want to get out of bed i don't want to do anything she goes

Speaker 1 you'll get over it depressed about what

Speaker 2 That's just the way it is.

Speaker 1 That's the way my mom is. You know, she was a single mother, raised me since I was two.

Speaker 2 I love her already. Oh, yeah.

Speaker 1 She's a G, she's, yeah, she's everything. You know, she did it all, right?

Speaker 1 So, so the fact that she raised me to be the way I am, I mean, kudos to her. Um, but no, I completely understand.

Speaker 1 And sometimes you have to separate yourself from that environment, you got to go somewhere where you're inspired, yep, where you start being around people that want to essentially help you level up.

Speaker 1 And it's, I think, a big cheat code. It is.
So, I think you going to the military actually builds you up to be successful in life.

Speaker 2 So, 1,000%.

Speaker 2 And here's what I tell everybody. God doesn't do things

Speaker 2 by happenstance. Right.

Speaker 2 He prepared me

Speaker 2 for my journey now with everything that I went through. Yeah.
Right. And so I'm able to sit here and talk and, and, and be here and go through the things that I did and grow

Speaker 2 because of all the stuff that I had to go through.

Speaker 1 Absolutely. Right.

Speaker 2 And you look at it and in that moment, you know, when you're depressed and you're anxious and you're just miserable and suicidal, you're like, life sucks. I'm never getting out of this.

Speaker 2 And now hindsight 2020, you're like, what was I really depressed about? And, you know, your mom said it about what? But in that moment, you don't know.

Speaker 1 You don't know.

Speaker 2 You don't know.

Speaker 2 And so

Speaker 2 it's okay.

Speaker 2 You know, if you, if, if you could understand at that moment that it was okay to be depressed, that it was okay to be in that point because God has a bigger plan. He does.

Speaker 2 What's his goal for you? You don't know, but you just better ride it out because it's going to be great.

Speaker 1 It's going to be great. And eventually, I always say this, number one, it could always be worse.
Yeah. It could always be worse in life.
Right.

Speaker 1 But then number two, when you guys ever go through critical incidents, you know, and this is for any listeners and for us too, we always have to reflect.

Speaker 1 Okay. We always have to reflect and remind ourselves that, hey,

Speaker 1 this is just happening now. Yeah.
It doesn't mean that's going to stick with us for the rest of our

Speaker 1 time here on earth, guys. And if we do,

Speaker 1 it's because we are going ahead and we're just absorbing that negativity or that bad moment in our life.

Speaker 2 Well, I'm going to tell you, keep it. Yeah.
Let it stick with you. Yeah.
Because how are you going to take what has happened and make it better for you?

Speaker 2 Don't ever,

Speaker 2 and this goes for a lot of entrepreneurs and this goes for a lot of people who have been through a lot of things, right?

Speaker 2 Don't ignore, don't forget what you went through.

Speaker 2 Pull out of the

Speaker 2 situation what you need to

Speaker 2 to grow, to get better, to get over, don't let it happen again. Yeah.
So

Speaker 2 I hear what you're saying, but don't don't ever forget it. And I think that for me and a lot of people that go through trauma,

Speaker 2 that's what we want to do. Yeah, like, hey,

Speaker 2 we've succeeded, right? We've gotten past it. Yeah, I'm good.
I'm never gonna think about it again.

Speaker 2 Okay, well, if you don't think about it again, and a situation pops up where it may be something similar, and then you go, Oh my gosh, I'm in this all over again, and then it pops up, and then you don't know how to prepare yourself.

Speaker 2 You're not prepared, yeah, because you're like, Oh, I just forgot about it, and I forgot what I did, and I moved on, I left it, I'm good. Yeah, no,

Speaker 2 Pull out of it what you can.

Speaker 2 Keep it.

Speaker 2 Don't make that same mistake twice.

Speaker 1 Yeah. The experience.
Yeah. The experience.
No, I believe experience is key, especially in entrepreneurship, because I don't see as any failures, there's lessons. Yeah.
Right.

Speaker 1 So at the end of the day, what makes some of the best entrepreneurs and also people in the military is that they take action. Yeah.

Speaker 1 And then there's some saying that we say in law enforcement is just, hey, dude, guess what? Just do it.

Speaker 1 And then if you mess up, just go back and and fix it yeah and that's what i that's that that's my go-to in life i'm like hey i'm just gonna go ahead ask for forgiveness later you know it is what it is right you break down the door just go back and fix it

Speaker 1 just say sorry wrong door right

Speaker 1 so let's talk about your transition now from the military you were in the military for about 12 years correct yep 12 and a half yeah okay and what what type of uh duties did you actually do in the military You want to laugh at me?

Speaker 2 Sure. I was a cop.
Really? I love that. I knew I liked her.
See that?

Speaker 2 I say that though, and it's two totally different things, the civilian side.

Speaker 2 But yes. So I was cop in the military, but the main focus for me in there was I guarded missile sites and the security.

Speaker 2 And then I turned around and I actually became the deployment manager for a maintenance group. Wow.
So, yeah. Pretty good.
I mean, it's kind of badass. It's all right.
It is. It is.

Speaker 1 I got to see those photos.

Speaker 1 All right. so how did you transition into from the military did you go straight into insurance or did you already had started your family at this time

Speaker 2 i started out

Speaker 2 i started out as a young mom okay a young mom at 19 at 19.

Speaker 1 you know

Speaker 1 back in the day

Speaker 2 All right.

Speaker 2 I'm aging ourselves, guys.

Speaker 2 It's normal. It is.
It's normal. It was.

Speaker 1 I don't know this idea of how people nowadays, especially on socials, right? They're like, oh, I don't want to have kids. So I'm like 40 or 50.
I'm like, dude, right now I'm like 37.

Speaker 1 I'm about to have my first kid. I'm man.
My energy levels are not there.

Speaker 2 I'm older than you. Damn.
Yeah.

Speaker 2 Yeah. All right.
I mean, that's a good thing. You look great.
Same. You look great.

Speaker 1 Then, you know, it says something, right? It does, yeah.

Speaker 2 Yeah. But no, you're 100% correct.
You know, because now you look at it, and I'm not that much older than you.

Speaker 2 At 38,

Speaker 2 I have two kids graduating this year.

Speaker 2 I have another one that says, he's a freshman. And then I started over.
She's three.

Speaker 2 But literally, like, I can retire. And now I'm starting another career.
And I have lived my best life.

Speaker 2 And now I get to watch at a young age, because I am young. Yes.
At a young age, I get to watch my kids. Grow, have kids of their own and still be that happy, energetic nana,

Speaker 2 you know, at that point, or travel with my kids, or I'm not old. Yeah.
I don't know if I could ever think, I mean, when I had my daughter at 35,

Speaker 1 game changer, bro.

Speaker 2 You know how old I felt? Yeah. It was hard.
I'm like, man, I totally wish I would have had another kid in my 20s. Yeah.
So much easier. Right.
But I digress. But yes, it's, I love being a mom.

Speaker 2 But I was a mom at 19.

Speaker 2 And so I started early and uh married military as well so we went through a lot of deployments um and then i went from active duty to a reserve because with my ex-husband he was gone so we were together for a total of 12 years married less but in that time

Speaker 2 He was gone 80% of the time. Wow.
So not only did I have to be a single mom, I still had a career. Right.
And then I had the military. Right.
And I ended up going AGR too.

Speaker 2 And so, but I'm trying to handle all of this and moving on my own.

Speaker 2 Like,

Speaker 2 so it, it sucked. Yeah.
You know, and so

Speaker 2 it never kind of, it never stopped. So when I went Garden Reserve and then my husband, who was older than me, he retired.

Speaker 2 And we moved back to Michigan. And that's when, I met

Speaker 2 a mentor for insurance who taught me insurance the right way. And so that's kind of how I got into insurance is because we moved back.
I was still guard at that point.

Speaker 2 And so I realized that, and then I became a firefighter. So in between that transition,

Speaker 2 I mean, I try. I like to know everything.
I can build a house and I can put out the fire that burnt it. It's fine.

Speaker 2 But for me, it was, I hated,

Speaker 2 okay. Let me ask you a question.
Sure.

Speaker 2 When you were a cop and you were dealing with that critical incident and you're dealing with that death, you're dealing with that horrible car accident or kidnapping or whatever it was, yeah,

Speaker 2 and then you had to go home

Speaker 2 and you don't know what ended up afterwards. Yeah, how'd that stick with you?

Speaker 1 Yeah, I would think about it, I would think about it until the next day, and then I would find out what happened.

Speaker 2 But again, you there was nothing that you could do, you'd find out what happened, but if it's

Speaker 2 meaningful to you,

Speaker 2 right, and you couldn't do anything past that yeah that drove me nuts i know my purpose in life is to serve yeah right to serve people

Speaker 1 and as a cop as a firefighter the only time that you can help that person is in that moment yeah and that's it yeah so and that's hard and the reason why i say it's hard is because you know what what i had to find out especially working for the city of oakland california in that place in itself i mean i've worked with so many marines

Speaker 1 Navy, Army.

Speaker 1 I even had an active commander that ran like special forces for the Marines during that time when I was working there. And I would always talk to him, I'll be like, hey, so what is it?

Speaker 1 Is it worse when you get deployed or is it worse here? And he goes, hands down,

Speaker 1 you guys are living it every day.

Speaker 1 When you get deployed, you get deployed for probably a couple months, couple years, and then you're done. But here, I mean, you got people working 15, 20, 30, 50 years, whatever it is.

Speaker 1 But what I finally came to realize is that, number one, you're one person.

Speaker 1 So it sort of sucks because when you go with the intentions of being a first responder,

Speaker 1 you want to help the world, right? You want to help people. You want to give them the shirt on your back.

Speaker 2 Make a difference. Make a difference, right?

Speaker 1 Yeah.

Speaker 1 You find out very quick how... Number one, the government works, the chain of command works.
I like to call it Game of Thrones because you get very political.

Speaker 2 I literally, yep. Yeah.

Speaker 1 It's just the way it is. It doesn't change.
The military is the same thing. Same thing.
So you can, you're very limited to what you can do.

Speaker 1 And I think, to be honest, it's the last two years, that's the reason why my fulfillment wasn't there. Like initially, when I first got into the job.
When I first got into the job,

Speaker 1 I was working under the sheriffs, but I was an Oakland police officer detective working under the sheriff. And it was different rules.

Speaker 2 Yeah.

Speaker 1 It was different rules. And when I got back to the department, it was just like more to like CYA, cover your butt,

Speaker 1 more of a political, you had to watch what you had to say. You had a lot of people that are very insecure that were commanders.
Yep.

Speaker 1 And they didn't let you police. And what do I mean by that, guys? What I mean is, you know, with the media going against first responders, cops,

Speaker 1 with the rules that were, especially not to get political, but in California, I was very strict with cops. They were letting criminals just run wild.
Yep.

Speaker 1 You know, and they knew they could get away with it. Yeah.

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Speaker 1 My mind came to what is the point of policing if they don't allow us to keep these criminals in jail.

Speaker 1 And they're just going to keep doing it.

Speaker 1 And that's why crime rose. Yep.

Speaker 1 And more people were moving out more than ever, including myself. I was basically pushed out to move out of California, even though California is beautiful, best weather.

Speaker 2 But at the end of the day, i mean it just really depends on what you want in life right yeah to me i was more to serve yeah like i love serve yeah yeah enjoyed the job it's a it's a mindset right to be willing to serve um and again it's a great personality trait to have as an entrepreneur serving people right yeah um for me insurance i get to serve people yeah from the time of disaster until the day that they say hey cassie i have a kid that is going on the insurance and, you know, here we go.

Speaker 2 Yeah. Okay, great.
I literally get to be there through the whole process and after they're put whole again. Yeah.

Speaker 2 Like,

Speaker 2 how, I mean, to me, it's so weird. Nobody looks at insurance and like, man, that's sexy.
No, that's not how it works, right? Nobody likes to talk insurance. Right.

Speaker 2 But when you take the insurance aspect and the business transaction out of insurance, what do you have? Yeah. You have a a relationship.

Speaker 1 You do.

Speaker 2 You have a purpose. And your purpose is to serve your clients.
Yeah.

Speaker 2 And so that's where I had this amazing boss who taught me, you know, A, do things right the first time, and then the underwriters will love you and they'll never question you ever again. Okay, great.

Speaker 2 But then two, insure the person's house correctly. Yeah.
Insure their cars correctly.

Speaker 2 Because when, and every state's different, you know, but, you know, when they get in that accident and they're not at fault,

Speaker 2 what are you going to do? What are they going to do? What's their first thought process? Right.

Speaker 2 I want to change that. Yeah.
I want to change that process. Right.
And then that's where the fire came in of like, yeah, I love this. Teach me more.
Teach me more. Teach me more.

Speaker 2 And so I was a lonely old,

Speaker 2 you know,

Speaker 2 CSR customer service rep helping, you know, yeah, we had to be licensed, but I mean, that's all I was doing. And I was just helping, you know, the farmers put tractor equipment on their policies.

Speaker 2 And, you know, that was it.

Speaker 2 That, it was nothing fantastic, it was nothing spectacular, but I learned and I learned how people ticked, and I learned what they really wanted because I would be that front line

Speaker 2 as soon as they walked in, and they're just fired up. And you're like, Okay, so this is what people get upset about.
This is what they want to know. Okay, how can I prevent that in the future?

Speaker 2 Yeah, so again, you take all of my training and okay, that's great.

Speaker 2 Then I left yeah and I moved

Speaker 2 and

Speaker 2 I was working for a company during COVID not ideal God's plan though because I was able to be at home schooling my children which they needed right

Speaker 2 and I had enough it was corporate political BS just not not my game and I quit if if if you ever go to a job and I say job because that's what it is and your leadership tears you down,

Speaker 2 and entrepreneurs take note of this because this is what you want to know for your team. If you make your team feel worthless, overworked,

Speaker 2 you're a constant tyrant, nobody's going to want to work for you.

Speaker 1 Absolutely right.

Speaker 2 And what are they going to do? They're sitting there like, and me personally, I always try and prove like I'm amazing at what I do. I always put 110% in.

Speaker 2 No, the day I walked in there, I was,

Speaker 2 you made me cry. I don't cry.

Speaker 2 I'm out.

Speaker 2 And so I went home. And I told my husband at the time, I was like, I quit.
And he goes, what? Like, I quit. I couldn't do it anymore.
I, like, I can't. I can't keep going.

Speaker 2 So I got on and I filled out stupid indeed applications, right? I was in that moment of anger and I was just like, I don't care what I do. I'll go work at McDonald's.

Speaker 2 Yeah, I'll go work at McDonald's. I don't care.
I just need to provide for my family, right? Survival. And I got a call for an insurance company, and I was like, I don't want to do insurance.

Speaker 2 I'm in a new state.

Speaker 2 Like, I didn't want to do it. But I was like, you know what?

Speaker 2 Fine. It was the only interview that I got back out of all the submissions, which I thought was crazy because I have an amazing background.
I have, you know, I have a degree in business.

Speaker 2 Like, come on.

Speaker 2 So I did.

Speaker 2 And that guy that hired me ended up being one of the most amazing mentors

Speaker 2 and one of the most fantastic and fabulous people that I've ever met in my entire life. I love that.
And I worked for him. He was silent.

Speaker 2 So he said, listen, I'm hiring you as my office manager. Him and I had a two-hour interview, right? And he, I had originally went in for a sales job.

Speaker 2 By the time I left, I was office manager and I had negotiated a significant pay increase from what was originally posted. And

Speaker 2 I started running the business.

Speaker 2 We scaled it to where the retention went from 60%.

Speaker 2 And people who are in insurance know retention is huge.

Speaker 2 That's your bread and butter. And so we went from a 60% retention to a 90% retention in less than six months.
Wow.

Speaker 2 We grew and we were hitting, we were consistently hitting the numbers that we needed to. And he came to me and he said, what are you doing?

Speaker 2 What do you mean? What am I doing?

Speaker 2 And he goes, what are you doing?

Speaker 2 Stop making me money. Make yourself money.

Speaker 2 And I laughed at him. I remember laughing at him.
And I'm like,

Speaker 2 you're funny. You're cute.
He's like, no, I'm serious. What's holding you back?

Speaker 2 Fear.

Speaker 2 I'm not good enough. I don't know what I'm doing.

Speaker 2 And he goes, when are you going to stop letting fear and what happened in the past take over and dictate your future? When are you going to stop?

Speaker 2 And I went,

Speaker 2 oh, man, that was, that's hard. That's deep.
I don't know. And he goes, just think about it.

Speaker 2 And I'm like, where am I going to get six figures?

Speaker 2 I am, I came from nothing.

Speaker 2 Absolutely nothing. Where, you know,

Speaker 2 we had to do some crazy things to be able to pay bills. Right.

Speaker 2 And I was living paycheck to paycheck, and you don't get paid worth a damn in the military. Everybody knows that, right? Single mom.
I live, I had zero money to my name.

Speaker 2 I don't even know how to finance anything that's not a car or a house. Come on.

Speaker 2 Where am I going to get this money from? And he was like, listen, I'm going to help you.

Speaker 2 Here's the number.

Speaker 2 to be able to get the loan because you already know the business is worth it. He goes, I'll front you the money to start.

Speaker 2 I needed one person to take a chance on me. One person.

Speaker 2 And he did.

Speaker 2 And I purchased it.

Speaker 2 So we started this process of purchasing the agency. And I was pregnant.
I was going through IVF. Wow.
Okay.

Speaker 2 Like I just told Big Mike outside, that screws with a woman's hormones. So I'm like, am I making an emotional decision? Am I irrational? Like, I'm all over the dang place, right?

Speaker 2 I delivered my daughter in the hospital on 127.22.

Speaker 2 I was in class for the agency takeover the very next day. Wow.

Speaker 2 I never took maternity leave, and I purchased the agency officially in my name, March 1st. Wow.

Speaker 2 So all my clients knew my daughter. Yeah.
Right. So here I am with this six-figure debt, a new baby, a new venture.

Speaker 1 New life.

Speaker 2 Scared as hell. It was crazy.

Speaker 2 But I took that

Speaker 2 and I changed the way that people saw me

Speaker 2 and insurance.

Speaker 1 Absolutely.

Speaker 2 And once I figured out, and again, paying attention, right? The people that come in, what are they complaining about? What's the problem? What are they, you just have to listen.

Speaker 2 You have to listen to people and they will tell you what they need. They will tell you what they want.

Speaker 2 That's, that's the key to life. Just listen.

Speaker 2 And so I did. And I scaled it 400%.

Speaker 2 I love that.

Speaker 2 And

Speaker 2 I ascend. I mean, I look back now.
It was the greatest,

Speaker 2 greatest adventure, the hardest, the most stressful because you're the boss. You have bills to pay.
You have

Speaker 1 overhead expenses. You have the liability.

Speaker 2 Yeah, well, and for me, it was the team. Like, I have mouths to feed in my office.

Speaker 2 I can't let them down. Correct.
And so

Speaker 2 I was able and blessed to be able to sell it 30 days prior to the three-year mark for a whole hell of a lot more than what I bought it for. Oh, I love that.
Yeah. You were able to exit.

Speaker 2 I did. I did.
So I exited.

Speaker 2 And my boss now

Speaker 2 was like, I need you because we want to shape like your mindset your drive what you stand for

Speaker 1 I that's what I want I want that woman and I'm like okay I think it's I think it's very inspiring because you were able to go ahead and have the social proof of a startup insurance company build it up exit and now you know you have other people that want to come and insert you as a consultant essentially yeah you know you should consider doing a consulting agency if you're not already well that's how I started.

Speaker 2 Yeah. I mean, and I told him, because he tried, and I was like, I don't know.
Like, I don't know. Right.

Speaker 2 What is my future? I don't want to make the wrong decision. Yeah.

Speaker 2 So, yeah, I consulted. I'll help you.
And I told him, I said, I'll help you. I'll help you structure it.
Yeah. I'll help you get going.
Right. And then he was like, no, I don't want that.
I want you.

Speaker 2 Right.

Speaker 2 Oh, okay.

Speaker 2 That's good. I'll take it.

Speaker 1 So what would you say to someone who is looking to break into insurance right now?

Speaker 1 Basically take your footsteps and try to eventually be able to have enough to buy an insurance agency or company and then scale that.

Speaker 1 What would be the initial steps that you would say you would give your old self coming outside the military and brand new, brand new boop? Yeah. Going into insurance.

Speaker 1 What would be three big needle movers that you would give them as advice?

Speaker 2 Well, so first off, you need to,

Speaker 2 I mean, social media is huge nowadays, right? And just about every insurance agency has a TikTok, has a Instagram, has a Facebook something.

Speaker 2 You need to look. And I mean, shoot me a DM, right? Because I'll get you who, what, when, where, how, and why.

Speaker 2 You need to find an agent that fits in your core values, right?

Speaker 2 As soon as you find that person that you can.

Speaker 2 that can be your mentor and that you can believe in and stand behind and has the same values. And that's going to be your first and foremost, like biggest goal to achieve.

Speaker 2 Because, again, like I said, insurance agents are not well-liked individuals. And especially if you're a female wanting to be in the insurance industry, I mean, that's a male-dominated role.

Speaker 2 And it's hard.

Speaker 2 But nobody likes insurance agents. They're money hungry.
If that's what you want to be and that's the type of agent you want to be, again,

Speaker 2 find that one, right?

Speaker 2 And then set yourself a list,

Speaker 2 right? You need to write out,

Speaker 2 here's where I'm at,

Speaker 2 here's where I want to be, here's the type of agency that I want to own, here's my values, here's my core, what's your mission? Once you have all of those

Speaker 2 and you have your the person that you're looking for, right? You're like, man, I'm going to follow that person because what they say, what they do is great. But you have to find your own unique

Speaker 2 message.

Speaker 2 How are you going to be different than the Joe Schmo that you're watching as a mentor, right?

Speaker 2 And so as soon as you have those,

Speaker 2 okay, now you need to find a consultant. Now you need to find somebody that has the inner workings of this is how you get a loan.
This is where you go.

Speaker 2 This is how you determine if you were going to purchase an agency or you're going to start one by yourself. Those are two very different things.

Speaker 2 One's very expensive and one's really expensive and really stressful. Yeah.
Right.

Speaker 2 Because purchasing an agency is actually easier than you think. Wow.
Because they're for sale all over. Yeah.
Right.

Speaker 2 And then once you find that book, if you're going to purchase one, you really need, there are certain things that you're going to need to know. You're going to need to know, is it profitable?

Speaker 2 What's their ROI? What's their turnaround? What's their profit and loss?

Speaker 2 I mean, there's a lot of different things when it comes to a book of business for insurance that people are like clueless about. Yeah.

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Speaker 2 Introducing the new sleep score on Apple Watch, iPhone 11 or later required. So I would say, I mean, DM me, obviously.

Speaker 2 Right? Where can they DM you?

Speaker 2 DM me, Cassie underscore 712020 or the Hot Mess Express, two T's on instagram um but that's what i would tell them because you're gonna want to find that person that's willing to educate you and help you with your goals yeah

Speaker 1 you have to so those would be my those would be my three i love that i love that it has a lot to do with my core values of self-education yep number one yep number two finding a mentor yep because as old school millennials yeah we never really use the word mentor no it was usually a parent a friend a coworker grandparent Grandparent.

Speaker 1 Someone who gave you advice and you never really processed it as they're mentoring me. Right.

Speaker 1 I feel like mentoring really is being used or was really put into place the last five years and it's because social media.

Speaker 1 Find a mentor, find a mentor, right? You got all these business gurus saying, mentor, mentor. And I never thought of it.
Like reflection.

Speaker 1 Again, I was just like, dude. The reason why I was able to do all this cool stuff in law enforcement, because I had mentors.

Speaker 2 I was just like, aha moment, right? Yes. But that's later in life.

Speaker 1 What would you say

Speaker 1 is the biggest needle mover

Speaker 1 for people currently right now in the military? They're trying to find number one, purpose.

Speaker 1 And number two,

Speaker 1 what would you recommend that they do to find that purpose?

Speaker 2 Let's go deep. Ooh, this is deep.
I love it. Okay, so.

Speaker 2 People in the military have a really hard time when they exit into the civilian world of finding their purpose. Because while you're in the military, you're given your purpose.

Speaker 2 We have a purpose, and I have goosebumps because this is so, like,

Speaker 2 this is deep. So,

Speaker 2 in the military, you are, your purpose is to save America. It is to, you've dedicated your life, whether

Speaker 2 you go on a combat zone or not, you have dedicated your life to keeping America safe. Yeah, I truly 100% believe in that.

Speaker 2 When you get out

Speaker 2 and you go, okay, like, what's next?

Speaker 2 There's actually a transition in the military. Before you go to get out, there's classes and stuff that they used to, I don't know anymore, they required you to take because it is a mental

Speaker 2 debilitator to go from being needed,

Speaker 2 having a purpose, to going out and going,

Speaker 2 do I go sell shoes? Like, what do I do?

Speaker 2 And then the jargon in between, so military jargon is, you know, it's fun because it doesn't translate in the civilian world.

Speaker 2 And so they have all of these amazing skills that we had talked about, right? Yeah.

Speaker 2 You have all these skills, but they,

Speaker 2 normal civilians are like, what does that even mean? Like, what did you do? You, okay, you built.

Speaker 2 I don't get it. I can't tell you how many times that that's how a conversation went.
A sentence was never finished because they just don't understand.

Speaker 2 Find what makes you happy,

Speaker 2 right? When you get out of the military, a job should not be a job. It should be a passion.

Speaker 2 Right.

Speaker 2 And so many military members get out and they're like,

Speaker 2 I'm going to go be a cop because there's a purpose. Very true.
Right? There's a purpose. Like, I've got my team.
I've got my camaraderie. I've got my purpose.
Like, and I get to use my training.

Speaker 2 And, and then they get in and they are so mentally not okay.

Speaker 2 They are just like, this is not what I signed up for. This is not how it is.
Every man for themselves, you know what I mean? And so they struggle. Well, I'm going to go work construction.

Speaker 2 Okay,

Speaker 2 sit down. There, in every single state, okay.

Speaker 2 In every single state, there is a veteran employment representative that can sit down with you and they have been trained

Speaker 2 to go, okay, this is is what you did in the military. Yeah, here's how it translates into the civilian world.

Speaker 2 You don't think you have that skill, but didn't you do X, Y, and Z? Then, yeah, you have that skill.

Speaker 2 And believe it or not, and I actually worked for the state of Michigan in this situation. That's how I know this exists.

Speaker 2 They literally come out of that meeting going,

Speaker 2 I have my confidence back.

Speaker 2 Like, I'm going to find a purpose. Yeah, it's going to be okay.

Speaker 2 And so please, please, please, if you are a veteran and you are getting ready to get out or you're, or you've already transitioned and you're just working a meaningless job and you're depressed and you're just not happy, go find a veteran employment rep and just sit with them and say, okay, like, listen, here's what I did in the military.

Speaker 2 Here's what I really enjoyed in the military. How does that translate? Like, what other jobs do you think?

Speaker 2 Because again,

Speaker 2 military, you're so, you're close-minded. And you don't, you don't want to be.
It's not kind of by choice, but it's more by

Speaker 2 that's who we are, right? We have one mission. We have one purpose.
Yeah. And so you kind of get that goggle vision.

Speaker 1 Loss in the sauce because you're so mission-driven.

Speaker 2 Yeah. Yeah.
Yeah. And so

Speaker 2 these people, they're amazing and they pull, they pull it out of you.

Speaker 2 I mean, they'll make you cry.

Speaker 2 That's their job, right?

Speaker 2 And they're going to tell you, like, hey, here's what I think you're good at. Here's a list.
It's like going to MEPs all over again. Here's a list of jobs that you, you know, you qualify for.

Speaker 1 And that's great. We all need that.
Yeah. Yeah.
You know, that in itself is mentorship.

Speaker 2 Yeah. And so that's what I would tell veterans.
You know, you want that needle mover, go just go sit down with somebody that understands the civilian world. Maybe another veteran, right?

Speaker 2 Who got out and has done it, right? Yeah. And I will say that a a very large portion of military members are amazing entrepreneurs.
Right.

Speaker 2 They are amazing entrepreneurs and they need to find what they're good at and how can they capitalize on it. Oh yeah.

Speaker 1 Oh yeah. Everybody got a story.
Yeah. You know, I always get asked, well, what makes you guys so special? Us, our story, who we are.
Yeah. You can never take that away from us.
No.

Speaker 2 And turn around and be like, you're special too. You just got to figure it out.

Speaker 1 Exactly. They just don't know how to extract it yet.

Speaker 2 No. I love that.

Speaker 1 so

Speaker 1 for the viewers and the listeners what would be some words of encouragement to have them level up in 2025 oh gosh don't give up

Speaker 2 embrace your mess-ups embrace your who you are as a person right um your story is unique and don't ever think and don't ever sell yourself short for the fact that your story is

Speaker 2 well somebody always has somebody else has it worse right and mine wasn't that bad it's all about circumstance. It's all about, you know, that perception of,

Speaker 2 hey, what you went through may not sound bad to me, but how did it affect you?

Speaker 2 So figure that out, you know, and don't stop. Don't let anybody tell you that,

Speaker 2 hey, that's a great idea, but I'll see you in a couple of weeks. You know what I mean? Don't, don't do that.

Speaker 2 Don't let them because that's where you're going to fall. Yeah.
And you're just going to be stuck.

Speaker 1 I love that. And that's the level up, guys.
And where can they find you?

Speaker 2 Oh, I'm on Instagram, Cassie underscore 71, or yeah, 721, 2020.

Speaker 2 And then the Hot Musk Express, two T's on Instagram, and then Cassie Kenna on Facebook.

Speaker 1 There you guys have it. Cassie's remarkable story of growth, the military.
being the president and owner exiting an insurance company. Phenomenal story, Cassie.
Thank you.

Speaker 1 With that being said, guys, leave a five-star review on Spotify, Apple Podcasts, and YouTube. Thank you for allowing us to be number one in entrepreneurship, number one in all categories.

Speaker 1 And we're going to try.

Speaker 1 Well,

Speaker 1 I never say try. I say we will be doing five million downloads in September, guys, because of you.
We're trying to go ahead and shoot for the stars. With that being said, guys, my name is Paul Alex.

Speaker 1 This is the Level Podcast. We'll catch you on the next one.

Speaker 2 Peace.

Speaker 2 Next up is a little song from CarMax about selling a car your way. You wanna sell those wheels, you wanna get a CarMax instant offer so fast, wanna take a sec to think about it

Speaker 2 Wanna keep tabs on that instant offer with OfferWatch Wanna have CarMax pick it up from the driveway

Speaker 2 So wanna drive?

Speaker 4 CarMax pickup not available everywhere restrictions and fee may apply