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

Summary

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The Level Up Podcast w/ Paul Alex

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

Date: November 15, 2025
Guest: Kassie Kenna
Host: Paul Alex Espinoza

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Episode Overview

In this inspiring episode, Paul Alex welcomes Kassie Kenna—a military veteran, mother of four, and successful insurance agency owner—to share her extraordinary journey from overcoming deep personal challenges to building, scaling, and later selling a thriving insurance business. The conversation unpacks Kassie’s story of resilience, her transition from the military to entrepreneurship, and the practical steps she took to turn fear into financial and personal success. This episode is a masterclass in mindset, perseverance, and service-driven leadership, especially for vets and underdogs looking to "level up" in life and business.

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Key Discussion Points & Insights

1. Kassie’s Early Life and Military Background

[03:02 - 07:00]

• Came from a challenging background in Michigan, facing both trauma and family pressure.
• Joined the Air Force at 19 after losing 150 lbs out of determination ("chicken and stairs" diet).
• Military service was transformative: “Entrepreneurship is not easy...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.” (06:00 - Kassie)

2. Adversity, Trauma, and Perseverance

[13:01 - 16:26]

• Shared candidly about surviving trauma and how that shaped her work ethic and resilience.
• Described lack of external support even from family: “My parents looked at me and they're like, we really hope that you make it, but if not, we'll see you in a few weeks. So it was already the doubt of, you're not going to make it. Destroyed me. So what happened? For eight weeks, I was focused.” (15:03 - Kassie)
• Developed a solo, “I must push through alone” mindset which later translated to entrepreneurship.

3. Teamwork, Growth, and Mission

[17:01 - 18:15]

• The military and entrepreneurial journey both focus on team and mission mentality.
• Paul and Kassie agree: find support environments and extract yourself from unsupportive ones.
• “God doesn't do things by happenstance. He prepared me for my journey now with everything that I went through.” (19:28 - Kassie)

4. Embracing and Learning from Hard Experiences

[20:49 - 22:29]

• Kassie emphasizes not forgetting one’s pain, but instead using it as fuel and wisdom:
  • “Don't ignore. Don't forget what you went through. Pull out of the situation what you need to grow, to get better, to get over. Don't let it happen again.” (21:39 - Kassie)
• Reflecting allows entrepreneurs to turn “mess-ups” into lessons, not lasting trauma.

5. Transitioning from Military Service to Business

[23:24 - 24:26]

• Kassie served as a cop and firefighter, managed deployments, juggled single motherhood, and moved frequently.
• Military service imbued her with discipline, leadership, adaptability, and an indomitable growth mindset.

6. Insurance: More than Sales—It’s Service

[03:48 - 05:15, 32:20 - 33:43]

• Kassie disrupted conventional insurance sales by focusing on relationships:
  • ”You teach people that they matter and not their money. That's the difference… In my old business, I had 2,723 clients. And I knew them all.” (04:23, 05:13 - Kassie)
• Insurance is an ongoing service, and purpose is to be there through clients’ life changes.

7. Overcoming Workforce Challenges & Finding Mentorship

[35:20 - 39:49]

• Left a toxic corporate culture; describes vital need for leaders to support—not belittle—their teams.
  • Quote: “If you make your team feel worthless, overworked, you're a constant tyrant. Nobody's going to want to work for you.” (35:20 - Kassie)
• By luck and grit, found a mentor who believed in her, coached her to “stop making him money; make yourself money.” (37:42)
• With mentor’s help, purchased agency, juggled IVF, pregnancy, and grew the agency by 400%.

8. From Ownership to Exit & New Ventures

[41:08 - 42:18]

• Successfully sold her agency just shy of three years for significant profit.
• Her reputation and results led to offers for leadership and consulting roles.

9. Practical Advice for Aspiring Insurance Entrepreneurs

[42:29 - 46:39]

• Find an agency and mentor that matches your values.
• Be clear about your personal and business mission.
• Learn the mechanics: acquisitions, finance, valuation, and industry KPIs.
• "You need to write out, here's where I'm at. 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?" (44:00 - Kassie)
• For direct mentorship, Kassie encourages DMs via Instagram (handles at the end).

10. Veteran Transition & Purpose After Service

[47:36 - 52:14]

• Veterans often struggle with purpose post-military; seek out Veteran Employment Reps who help translate military skills for civilian jobs.
• Serving a new purpose—passion-led vs. “just a job.”
• “A job should not be a job, it should be a passion.” (48:00 - Kassie)

11. Words of Wisdom for Leveling Up in 2025

[53:07 - 54:00]

• Embrace your failures and unique story; don’t let anyone diminish your experience or ambition.
• “Embrace your mess ups. Embrace your, who you are as a person. Right. Your story is unique. And don't ever think, don't ever sell yourself short..." (53:07 - Kassie)

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Memorable Quotes & Moments

“When are you going to stop letting fear and what happened in the past take over and dictate your future?”
— Kassie Kenna [37:43]

“God doesn't do things by happenstance. He prepared me for my journey now with everything that I went through.”
— Kassie Kenna [19:28]

"You teach people that they matter and not their money. That’s the difference.”
— Kassie Kenna [04:23]

"If you make your team feel worthless, overworked, you're a constant tyrant. Nobody's going to want to work for you."
— Kassie Kenna [35:20]

"Embrace your mess ups. Embrace your, who you are as a person. Right. Your story is unique."
— Kassie Kenna [53:07]

---

Key Timestamps for Reference

• [03:02] Kassie shares her military background and family/motherhood story.
• [06:00] Military’s role in entrepreneurial mindset and confidence.
• [15:03] Parental doubt and Kassie’s focus during basic training.
• [19:28] Faith and preparation for the journey.
• [21:39] Turning trauma into empowerment, not forgetting the lessons.
• [37:43] Mentor calls Kassie to stop letting fear dictate her future.
• [40:40] Scaling her agency by 400%.
• [44:00] Step-by-step advice for starting and excelling in insurance.
• [48:00] Advice to veterans on finding purpose and meaningful work.
• [53:07] Kassie’s closing message on embracing your story and leveling up.

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Where to Find Kassie Kenna

• Instagram: @cassie_712020 OR @thehotmessexpress (with two T’s)
• Facebook: Cassie Kenna

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Recap & Takeaways

• Resilience and the ability to adapt are the foundation of Kassie’s success—skills forged in adversity and the Air Force.
• Service-first mentality wins in entrepreneurship, especially in industries built on trust like insurance.
• Mentorship and community are vital for personal and business growth; don’t be afraid to seek help or advice.
• Translation of skills for veterans and those changing careers is possible and rewarding—seek the right support.
• Your story and setbacks are unique assets; growth comes from embracing, not erasing, your hardships.

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Closing Words

This episode delivers both actionable advice and emotional resonance for anyone who’s ever felt fear, faced obstacles, or doubted what’s possible. Kassie epitomizes the "level up" mindset: overcome, adapt, and win—and then help others do the same.

For more similar episodes and to connect with Paul Alex, visit OfficialPaulAlex.com or follow Paul on Instagram @PaulAlex.

Transcript

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[Cassie Kenna]

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. 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. Him and I had a two hour interview. I had originally went in for a sales job. By the time I left, I was office manager and I had negotiated significant pay increase from what was posted and I started running the business. 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? Stop making me money. Make yourself money. 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. And he goes, when are you going to stop letting fear dictate your future?

[Paul Alex]

Guys, welcome back to Level Podcast.

[Co-host (possibly Paul’s co-host)]

This is Paul, Alex.

[Paul Alex]

We're currently ranked number one in categories.

[Co-host (possibly Paul’s co-host)]

In all categories and number one in.

[Paul Alex]

Business because of you guys. Thank you for the 4 million downloads last month. This month we are shooting to 5 million.

[Co-host (possibly Paul’s co-host)]

All right, Amelia, we're gonna make it happen, right? That's right.

[Paul Alex]

All right. With that being said, we have another phenomenal guest at the Level up where we're gonna be talking about growth.

[Co-host (possibly Paul’s co-host)]

Okay?

[Paul Alex]

Growth is the key needle mover for this story, and you guys are gonna love this. She's president and owner of an insurance company for the past 14 years.

[Co-host (possibly Paul’s co-host)]

This insurance company is massive, by the way. Okay. So you guys are gonna love this. For all my insurance gurus out there, you guys are probably tuning in.

[Paul Alex]

Like, who's this?

[Co-host (possibly Paul’s co-host)]

All right.

[Paul Alex]

But we're gonna educate you and entertain you guys. She also has a phenomenal podcast where she talks about growth overcoming critical incidents. And also she's from the military. We love military folks.

[Co-host (possibly Paul’s co-host)]

Okay, thank you for your service.

[Paul Alex]

Air Force for 12 years. But she's also gonna be talking about bad relationships, motherhood, and how you guys can overcome this with your limiting beliefs.

[Co-host (possibly Paul’s co-host)]

That's what it's about. It's about leveling up. Welcome to the show.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

I'm excited, too. It's gonna be good.

[Cassie Kenna]

It is. It's gonna be fantastic.

[Co-host (possibly Paul’s co-host)]

So for the people that don't know you, who are you? And give us a little bit of a preview on your background.

[Cassie Kenna]

My name is Cassie Kenna, and I am prior military, like you said, 12 and a half years. Cop. I was also a firefighter. I'm a mother of four beautiful children. And. And 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 it's been quite a. Quite a journey for me.

[Co-host (possibly Paul’s co-host)]

Quite a journey.

[Cassie Kenna]

Yeah.

[Paul Alex]

So let's talk about it right now.

[Co-host (possibly Paul’s co-host)]

You've been in the insurance game for 14 years.

[Cassie Kenna]

On and off.

[Co-host (possibly Paul’s co-host)]

Yep, on and off.

[Paul Alex]

And we'll start off. We'll start off with that, because everybody knows insurance, right? So what would you say would make.

[Co-host (possibly Paul’s co-host)]

Somebody be great in insurance?

[Cassie Kenna]

You have to. So here's where we're gonna 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. You can sell ice to an Eskimo. 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. You're just creating relationships. That's how I built my agency. You. You teach people that they matter and not their money. That's the difference.

[Gemini Credit Card Advertiser]

Yeah.

[Cassie Kenna]

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, how to. How to grow, how to scale. Change your outlook on what insurance is. Yeah, that's what I would tell people. I tell my team that right now, 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. 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. 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? Do they. Did they know your name? Like, that's a huge thing. Do they know your kids?

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

In my old business, I had 2,723 clients.

[Co-host (possibly Paul’s co-host)]

Wow. Wow.

[Cassie Kenna]

And I knew them all.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Paul Alex]

I mean, that's the way it's supposed to be. I. I feel like, you know, as.

[Co-host (possibly Paul’s co-host)]

I start hiring younger and younger folks coming into sales.

[Cassie Kenna]

You're just saying that. We're old. Come on.

[Paul Alex]

We're old school millennials.

[Cassie Kenna]

That's right.

[Paul Alex]

Yeah, we're old school, Millen. We're the best.

[Co-host (possibly Paul’s co-host)]

Okay.

[Paul Alex]

But when it comes down to it, we're so used to talking to people.

[Co-host (possibly Paul’s co-host)]

In person like this.

[Cassie Kenna]

Yeah, Right.

[Co-host (possibly Paul’s co-host)]

Being relatable.

[Cassie Kenna]

They don't know how to do it anymore.

[Paul Alex]

Being able to go ahead and extract information.

[Cassie Kenna]

Yeah, Right.

[Co-host (possibly Paul’s co-host)]

Getting to really get to know someone.

[Paul Alex]

I think that's key.

[Gemini Credit Card Advertiser]

Behind sales.

[Co-host (possibly Paul’s co-host)]

Soft skills, right?

[Cassie Kenna]

It is, yeah. Yeah.

[Paul Alex]

So I.

[Co-host (possibly Paul’s co-host)]

So I resonate with everything that you.

[Paul Alex]

Said, but do you believe that your.

[Co-host (possibly Paul’s co-host)]

Background in the military actually helped you become a successful entrepreneur?

[Cassie Kenna]

Oh, my gosh. I am so glad she asked. Yes. Because it taught me perseverance. You know, entrepreneurship is not easy.

[Co-host (possibly Paul’s co-host)]

No, it's not.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

Well, I got it when I was a cop. Let's be real.

[Cassie Kenna]

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 there. You know, you do have to follow orders. But what is that order? And who's making those orders?

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

Are you now giving them?

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Right. And so 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. You know, prior to the military, I was very meek. I was destroyed emotionally and mentally. You know, and the military brought that confident woman out.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Right?

[Cassie Kenna]

Right. 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.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

But it's hard.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You know, the military teaches you to be tough.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Paul Alex]

But you know what? In the military, it shows you how.

[Co-host (possibly Paul’s co-host)]

To be discipline, be a leader.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

You know, be able to build relationships.

[Pipedrive Advertiser]

Why?

[Paul Alex]

Because it's needed. It's the fundamentals when it comes to life.

[Co-host (possibly Paul’s co-host)]

Right.

[Paul Alex]

To actually being an active human being.

[Co-host (possibly Paul’s co-host)]

In this organization or productive world.

[Cassie Kenna]

Productive, right. Yes. Yeah.

[Paul Alex]

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

[Cassie Kenna]

So I went in the military age 19. So.

[Audience Reaction / Minor Speaker]

Wow.

[Co-host (possibly Paul’s co-host)]

Right off the gate.

[Cassie Kenna]

Well, so kind of. So I traveled. I was an exchange student. So my senior year of high school, I graduated in another country. I came back.

[Co-host (possibly Paul’s co-host)]

Whereabouts?

[Cassie Kenna]

Brazil.

[Co-host (possibly Paul’s co-host)]

Why Brazil?

[Cassie Kenna]

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

[Paul Alex]

You were basically voluntold.

[Cassie Kenna]

Yes, exactly. Yeah. So again, it. I loved it, though. So part of that actually helped the military because you. I had to learn how to adapt and overcome at the age of 17.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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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[Paul Alex]

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[Co-host (possibly Paul’s co-host)]

No, absolutely. And then you probably stand out like, oh, yeah. No other probably, like, wait a minute, 1,000? Yeah.

[Pipedrive Advertiser]

Who is this?

[Cassie Kenna]

You know, I'm sorry, Blonde hair, blue eyes. In Brazil. Yeah.

[Paul Alex]

So that happens.

[Cassie Kenna]

Yep.

[Paul Alex]

And then how do you get into the military?

[Cassie Kenna]

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, the marine recruiter. Now give me the look. Now, I chose better. Okay. No, but the marine recruiter looked at me and he laughed and he said, I think it's great that you want to do this, but physically you're never going to be able to because I was £300.

[Gemini Credit Card Advertiser]

Wow.

[Cassie Kenna]

So when I went to Brazil, I gained £150.

[Co-host (possibly Paul’s co-host)]

Good food.

[Cassie Kenna]

Oh, my gosh, that and alcohol was amazing. Told them that last night at dinner, I was like, guys, so. And they can drink at 18.

[Co-host (possibly Paul’s co-host)]

Yeah, yeah, yeah.

[Cassie Kenna]

So I came back and I'm like, what am I gonna do? I want to join the military. This is. This is my way out.

[Co-host (possibly Paul’s co-host)]

Right?

[Cassie Kenna]

Right. I don't want to be here anymore. And that's because of Past trauma. Right.

[Co-host (possibly Paul’s co-host)]

And where. And where was here?

[Cassie Kenna]

Michigan.

[Gemini Credit Card Advertiser]

Michigan.

[Cassie Kenna]

Yep. Yep. So my hometown. 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? Yeah, I do. Then go do it.

[Co-host (possibly Paul’s co-host)]

Yeah, why not?

[Cassie Kenna]

So I did. So at 18, from the age of 18 to 19, I lost 150 pounds.

[Co-host (possibly Paul’s co-host)]

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

[Cassie Kenna]

Chicken.

[Paul Alex]

Most people are probably like, what? I eat chicken all day every day.

[Cassie Kenna]

But.

[Paul Alex]

But, guys, here's the thing that she.

[Co-host (possibly Paul’s co-host)]

That she's not telling you. It has to be portions.

[Pipedrive Advertiser]

Okay.

[Co-host (possibly Paul’s co-host)]

That's where I made the mistake.

[Cassie Kenna]

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 podcast. And just speaking it's choice. And you had an elevator and you got steps. 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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And so that's what I did. A ton of chicken. Took out all sugars, stopped drinking sodas, and I. I pushed forward. And. Yeah. And so I did. I lost 150 pounds. I joined. And then. Yeah, I was number one. I graduated number one academically. I don't know what you guys call it, but it was dorm chief, so we, you know, number one there. And then physically, I was literally number one. And no one, not even my parents, believe that that was something that was capable.

[Co-host (possibly Paul’s co-host)]

Wow. And why do you think that?

[Cassie Kenna]

So my parents didn't know what happened to me. Right. So I was raped in school. I was drugged and raped.

[Gemini Credit Card Advertiser]

Wow.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

I. There's a lot of depression, a lot of anxiety. The drinking. I drank a lot. Right. And so they had no idea.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And so they see a girl who is their only daughter who is required by statue to prove herself. Like, you have to get good grades. You have to be great at softball, you have to be great at hockey. Like, there's no option.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

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. 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. 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. So it was already. The doubt of, you're not going to make it.

[Gemini Credit Card Advertiser]

Yeah.

[Cassie Kenna]

Destroyed me. So what happened? For eight weeks, 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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And I just pushed through, and they didn't make it for my graduation. And that, for me, was a sign of. I'm. I'm alone. I'm gonna have to push through this world by myself.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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. Nobody is going to take away my entrepreneurship.

[Pipedrive Advertiser]

Right.

[Cassie Kenna]

So, yeah, it. There's a lot, you know.

[Co-host (possibly Paul’s co-host)]

Yeah, that's. That's.

[Pipedrive Advertiser]

That's hard.

[Paul Alex]

I feel like, you know, a lot of people, they get into situations, specific.

[Co-host (possibly Paul’s co-host)]

Situations in life, and they just let it consume them. For years, you had a situation happen to you, and you essentially took that pain and you made it productive. Right. Even your parents not believing in you. Right.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

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.

[Paul Alex]

So I think what had happened for.

[Co-host (possibly Paul’s co-host)]

You, 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, and they put you in a supportive environment. Like the military. Right. It's a military. It's built on more teamwork.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

You know, getting it done together.

[Pipedrive Advertiser]

Yep.

[Co-host (possibly Paul’s co-host)]

Right. We have one of my nutrition fitness guys out here in the hallway.

[Cassie Kenna]

Amazing. By the way, Clown.

[Co-host (possibly Paul’s co-host)]

And Mike. Big Mike, He's a big teddy bear.

[Cassie Kenna]

Big Mike is great, guys.

[Co-host (possibly Paul’s co-host)]

Yeah, he's great.

[Paul Alex]

And. But. But he's big on team.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

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.

[Cassie Kenna]

Yeah.

[Paul Alex]

So. So I. I've worked with a lot.

[Co-host (possibly Paul’s co-host)]

Of military folks, you know, being my time in law enforcement, and I think it's great. I think that it's big needle mover. The fact that you've expressed that on this podcast, because there's going to be.

[Paul Alex]

A lot of people that listen to.

[Co-host (possibly Paul’s co-host)]

This, and they've been in bad situations, and they just do not Have a support system.

[Paul Alex]

And I think it's very important. I think it's very important to talk about it. You know, towards the last two years.

[Co-host (possibly Paul’s co-host)]

Of my law enforcement journey, I felt into deep depression over some bs, now that I think about it. But still, it just. It piles up. Right.

[Paul Alex]

And then on top of that, you.

[Co-host (possibly Paul’s co-host)]

Could go to my mom, who, you know, I always consider my best friend.

[Paul Alex]

Even though we bump heads all the time.

[Cassie Kenna]

And I go, that's the best friend. That's the best friend.

[Paul Alex]

Best friend.

[Cassie Kenna]

They're gonna tell you what you don't want to hear.

[Paul Alex]

Exactly. And she tells me that. She's like, you know, listen, you might get mad at me, but it's because.

[Co-host (possibly Paul’s co-host)]

I tell you the truth.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

No one else will tell you the truth, Paul. Everybody always wants to kiss your butt. And I'm like, yeah, sure, Mom.

[Paul Alex]

But when I went to her back.

[Co-host (possibly Paul’s co-host)]

When I felt in deep depression, I told, mom, I'm depressed.

[Paul Alex]

Like, this is not cool. Like, I don't want to get out of bed. I don't want to do anything.

[Co-host (possibly Paul’s co-host)]

Goes. You'll get over it. Depressed about what?

[Paul Alex]

That's just the way it is. That's the way my mom is. You know, she was a single mother.

[Co-host (possibly Paul’s co-host)]

Raised me since I was 2.

[Cassie Kenna]

I love her already.

[Co-host (possibly Paul’s co-host)]

Oh, yeah, She's. She's a g. She's. Yeah, she's everything. You know, she did it all. Right.

[Paul Alex]

So. So the fact that she raised me.

[Co-host (possibly Paul’s co-host)]

To be the way I am, I mean, kudos to her.

[Paul Alex]

But no, I completely understand. And sometimes you have to separate yourself from that environment.

[Co-host (possibly Paul’s co-host)]

You gotta go somewhere where you're inspired.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

Where you start being around people that want to essentially help you level up.

[Paul Alex]

And it's, I think, a big cheat code.

[Cassie Kenna]

It is.

[Paul Alex]

So I think you going to the.

[Co-host (possibly Paul’s co-host)]

Military actually build you up to be successful in life.

[Cassie Kenna]

So 1000%. And here's what I tell everybody. God doesn't do things by happenstance. Right. He prepared me for my journey now with everything that I went through.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

Absolutely right.

[Cassie Kenna]

And you look at it in. In. 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. And now hindsight 20 20, you're like, what was I really depressed about? And, you know, Your mom said it perfect about what? But in that moment, you don't know.

[Co-host (possibly Paul’s co-host)]

You don't know.

[Cassie Kenna]

You don't know. And so it's. It's okay.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You know, if. If you. If. If you could understand at that moment that it was okay to be depressed.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

That it was okay to be in. In that point. Because God has a. A bigger plan. He does.

[Paul Alex]

Bigger plan.

[Cassie Kenna]

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

[Paul Alex]

It's going to be great. And eventually, I always say this.

[Co-host (possibly Paul’s co-host)]

Number one, it could always be worse.

[Cassie Kenna]

Yeah.

[Paul Alex]

It could always be worse in life.

[Co-host (possibly Paul’s co-host)]

Right.

[Paul Alex]

But then number two, when you guys.

[Co-host (possibly Paul’s co-host)]

Ever go through critical incidents, you know, and this is for any listeners and for us, too, we always have to reflect. Okay. We always have to reflect and remind ourselves that, hey, this is just happening now.

[Cassie Kenna]

Yeah.

[Paul Alex]

It doesn't mean that it's gonna stick.

[Co-host (possibly Paul’s co-host)]

With us for the rest of our time here on Earth, guys. And if we do, it's because we are going ahead and we're just absorbing that negativity or that bad moment in our life.

[Cassie Kenna]

I'm gonna tell you. Keep it.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Let it stick with you.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Because how are you gonna take what has happened and make it better for you? Mm. Don't ever. And. 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. Don't ignore. Don't forget what you went through.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Pull out of the. The situation, what you need to. To grow, to get better, to. To get over. Don't let it happen again.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

So I. I hear what you're saying, but don't ever forget it. I think that for me and a lot of people that go through trauma, that's what we want to do. Like, hey, we've succeeded. Right. We've gotten past it.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

I'm good. I'm never gonna think about it again. Okay, well, if you don't think about it again and 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. You're not prepared.

[Paul Alex]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

No, pull out of it. What? You can keep it. Don't make the same mistake twice.

[Co-host (possibly Paul’s co-host)]

Yeah, the experience. Yeah, the experience.

[Paul Alex]

Now, I believe experience is key, especially in entrepreneurship, because I don't. I don't see as any failures. There's lessons.

[Cassie Kenna]

Yeah. Right.

[Paul Alex]

So at the end of the day, what makes some of the best entrepreneurs and also people in the military is.

[Co-host (possibly Paul’s co-host)]

That they take action.

[Cassie Kenna]

Yeah.

[Paul Alex]

And then there's some saying that we say in law enforcement is just, hey, dude, guess what?

[Co-host (possibly Paul’s co-host)]

Just do it. And then if you mess up, just go back and fix it.

[Cassie Kenna]

Yeah.

[Paul Alex]

And that's what that. That's my go to in life. I'm like, hey, I'm just going to go ahead, ask for forgiveness later. You know, it is what it is, right?

[Cassie Kenna]

You break down the door, just go back and fix it. It's fine.

[Paul Alex]

Just say, sorry, wrong door. Right. So let's talk about your transition now from the military. You were in the military for about 12 years, correct?

[Cassie Kenna]

Yep. 12 and a half.

[Paul Alex]

Yeah. Okay. And what type of duties did you.

[Co-host (possibly Paul’s co-host)]

Actually do in the military?

[Cassie Kenna]

You want to laugh at me?

[Paul Alex]

Sure.

[Cassie Kenna]

I was a cop. Really?

[Paul Alex]

I love that. I knew I liked her.

[Pipedrive Advertiser]

See that?

[Cassie Kenna]

I see that though. And it, It's. It's two totally different things. The civilian side and. But yes. So I was. I was cop in the military, but the main focus for me in there was I guarded missile sites and. And the security. And then I turned around and I actually became the deployment manager for a maintenance group.

[Co-host (possibly Paul’s co-host)]

Wow.

[Cassie Kenna]

So, yeah, pretty good. I mean, it's kind of badass. It's all right.

[Co-host (possibly Paul’s co-host)]

It is, it is.

[Paul Alex]

I got, I got to see those photos. 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?

[Cassie Kenna]

I started out. I started out as a young mom. Okay.

[Paul Alex]

A young mom.

[Cassie Kenna]

At 19.

[Gemini Credit Card Advertiser]

At 19.

[Co-host (possibly Paul’s co-host)]

You know, back in the day, I'm aging ourselves, guys.

[Paul Alex]

It's normal.

[Cassie Kenna]

It is.

[Paul Alex]

It's normal. It was, 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. I'm about to have my first kid.

[Co-host (possibly Paul’s co-host)]

I'm.

[Paul Alex]

Man, my energy levels are not there.

[Cassie Kenna]

Wait, I'm older than you? Damn. Yeah. All right.

[Paul Alex]

I mean, that's good that you look great. You look great. You know, it's. It says something, right?

[Cassie Kenna]

It does. Yeah. But no, you. You're 100. Correct. You know, because now you look at it and. And I'm not that much older than you. At 38, I have two kids graduating this year.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

I have another one that says he's a freshman. And then I started over. She's three. But literally, like, I can retire. And now I'm starting another career. And I have lived my best life.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And now I get to watch at a young age. Because I am young.

[Co-host (possibly Paul’s co-host)]

Yes.

[Cassie Kenna]

At a young age, I get to watch my kids grow.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Have kids of their own and still be that happy, energetic Nana.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You know, at that point. Or travel with my kids or. I'm not old.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

I don't know if I could ever think. I mean, when I had my daughter at 35.

[Gemini Credit Card Advertiser]

Game changer, bro.

[Cassie Kenna]

You know, old. I felt, yeah, it was hard. I'm like, man, I totally wish I would had another kid in my 20s.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

So much easier.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

But I digress. But yes, it's. I love being a mom, but I was a mom at 19, and so I started early and married military as well. So we went through a lot of deployments, 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, he was gone 80% of the time.

[Co-host (possibly Paul’s co-host)]

Wow.

[Cassie Kenna]

So not only did I have to be a single mom, I still had a career. Right. And then I had the military.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

And I end up going egr, too. And so. But I'm trying to handle all of this and moving on my own, like, so it. It sucked.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You know, and so it never kind of. It never stopped. So when I went Garden reserve, and then my husband, who was older than me, he retired and we moved back to Michigan. And that's when I met my 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. And so I realized that. And then I became a firefighter. So in between that transition, you did it all. 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. But for me, it was. I hated. Okay, let me ask you a question.

[Co-host (possibly Paul’s co-host)]

Sure.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And then he had to go home, and you don't know what ended up afterwards.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

How'd that stick with you?

[Paul Alex]

Yeah. I would think about it. I would think about until the next.

[Co-host (possibly Paul’s co-host)]

Day, and then I would find out what will happen. Yeah.

[Cassie Kenna]

But again, you. There was nothing that you could do. You'd find out what happened, but if it's meaningful to you. Right. And you couldn't do anything past that.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

That drove me nuts.

[Co-host (possibly Paul’s co-host)]

I know.

[Cassie Kenna]

My purpose in life is to serve.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Right. To serve people. And as a cop, as a firefighter, the only time that you can help that person is in that moment.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And that's it.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

So.

[Co-host (possibly Paul’s co-host)]

And that's hard.

[Paul Alex]

And the reason why I say it's.

[Co-host (possibly Paul’s co-host)]

Hard is because, you know what, What I had to find out, especially working for the city of Oakland in California and that place in itself. I mean, I've worked with so many Marines, Navy, Army.

[Pipedrive Advertiser]

Yeah.

[Co-host (possibly Paul’s co-host)]

I even had an active commander that ran like, Special Forces for the Marines during the time when I was working there.

[Paul Alex]

And I would always talk to them. I'll be like, hey, so what is it?

[Co-host (possibly Paul’s co-host)]

Is it worse when you get to plan deployed, or is it worse? Here he goes.

[Paul Alex]

Hands down. You guys are living it every day.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

When you get deployed, you get deployed for probably a couple months, a couple years.

[Cassie Kenna]

Yeah.

[Pipedrive Advertiser]

And then you're done.

[Paul Alex]

But here.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

I mean, you got people working 15, 20, 30, 50 years, whatever it is.

[Paul Alex]

But what, What I finally came to.

[Co-host (possibly Paul’s co-host)]

Realize is that, number one, you're one person.

[Paul Alex]

So it sort of sucks because when.

[Co-host (possibly Paul’s co-host)]

You go with the intentions of being a first responder.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

And you want to help the world. Right. You want to help people, you want to give them the shirt out of your back.

[Cassie Kenna]

Make a difference.

[Paul Alex]

Make a difference.

[Pipedrive Advertiser]

Right.

[Cassie Kenna]

Yeah.

[Paul Alex]

You, you, you, you find out very.

[Co-host (possibly Paul’s co-host)]

Quick how, number one, the government works. The chain of command works. I like to call it Game of Thrones because.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

Get very political.

[Cassie Kenna]

I live. Yep.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Paul Alex]

It's just the way it is. It doesn't change in the military. It's the same thing.

[Cassie Kenna]

Same thing.

[Pipedrive Advertiser]

So you can.

[Paul Alex]

You're very limited to what you can do.

[Co-host (possibly Paul’s co-host)]

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.

[Cassie Kenna]

Yeah.

[Paul Alex]

I first got into the job, I.

[Co-host (possibly Paul’s co-host)]

Was working under the sheriff's, but I was an Oakland police officer, detective working under the sheriff. And it was different rules.

[Cassie Kenna]

Yeah, it was different rules.

[Co-host (possibly Paul’s co-host)]

And when I got back, back to the department, it was just like more to like, cya. Cover your butt. More of political. You had to watch what you had to say. You had a lot of people that are very insecure. That were commanders. Yep.

[Gemini Credit Card Advertiser]

And.

[Paul Alex]

And they didn't let you police.

[Co-host (possibly Paul’s co-host)]

And what do I mean by that, guys? What I mean is, you know, with the media going against first responders cops with the rules that were especially not to get political, but in California, I was very strict with cops. They were having criminals just run wild.

[Pipedrive Advertiser]

Yep.

[Co-host (possibly Paul’s co-host)]

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

[Gemini Credit Card Advertiser]

Yeah.

[Pipedrive Advertiser]

So good.

[Co-host (possibly Paul’s co-host)]

So good.

[Cassie Kenna]

So good.

[Nordstrom Rack Advertiser]

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[Cassie Kenna]

Because there's always something new.

[Nordstrom Rack Advertiser]

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[FINRA Advertiser]

So you're about to make a trade based on a friend's text, but which u do you listen to? Is it we could buy a house in Tulum. Get optioning those options. We could lose everything. Or let's do a little research. Get your head in the trade and make the investment decision that's right for you. Learn [e-mail] TradeSmart My mind came to.

[Co-host (possibly Paul’s co-host)]

What is the point of policing if they don't allow us to keep these criminals in jail? And they're just gonna keep doing it.

[Paul Alex]

And that's why crime rose.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

And more people are moving out more than ever, including myself. I was basically pushed out to move out of California. Even though California is beautiful, best weather. But at the end of the day, I mean, it just really depends on what you want in life. Right?

[Cassie Kenna]

Yeah.

[Paul Alex]

To me, I was more to serve.

[Cassie Kenna]

Yeah.

[Paul Alex]

Like, I love.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

Yeah. I enjoyed the job.

[Cassie Kenna]

It's a. It's a mindset, Right. To be willing to serve. And again, it's a great personality trait to have as an entrepreneur. Serving people. Right?

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

For me, insurance, I get to serve people.

[Paul Alex]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Like 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.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

But when you take the insurance aspect and the business transaction out of insurance, what do you have?

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You have a relationship.

[Co-host (possibly Paul’s co-host)]

You do.

[Cassie Kenna]

You have a purpose, and your purpose is to serve your clients.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And so that's where I had this amazing boss who taught me, you know, a. Do things right the first time, and then underwriters will love you, and they'll never question you ever again. Okay, great. But then two, ensure the person's house correctly.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Ensure their cars correctly. Because when. And every state's different, you know, but, you know, when they get in that accident and they're not at fault, what are you going to do? What are they going to do? What's their first thought process? Right. I want to change that.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

And so I was a lonely old, you know, 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. And, you know, that was it. 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 frontline 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? Yeah. So again, you take all of my training and. Okay, that's great. Then I left and I moved, and 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. 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. 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, you're a constant tyrant. Nobody's going to want to work for you.

[Co-host (possibly Paul’s co-host)]

Absolutely.

[Cassie Kenna]

Right. And what. What are they going to do? They're sitting there like. And. And me personally, I always try and prove, like, I'm amazing at what I do. I always put 110 in. No. The day I walked in there, I was. I. You made me cry. I don't cry. Yeah, I'm out. 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. 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. Yeah, I'll go work 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. I'm in a new state. And like, I didn't want to do it, but I was like, you know what? 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. Like, come on. So I did. And that guy that hired me ended up being one of the most amazing mentors and one of the most fantastic and fabulous people that I've ever met in my entire life.

[Gemini Credit Card Advertiser]

I love that.

[Cassie Kenna]

And I worked for him. He was silent. 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. By the time I left, I was office manager. And I had negotiated a significant pay increase from what was originally, you know, posted. And I started running the business. We. We scaled it to where the retention went from 60%. And people who are in insurance know retention is huge. That's like, that's your bread and butter. And so we went from a 60% retention to a 90% retention in less than six months.

[Gemini Credit Card Advertiser]

Wow.

[Cassie Kenna]

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? What do you mean, what am I doing? And he goes, what are you doing? Stop making me money. Make yourself money.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And I laughed at him. I remember laughing at him. And I'm like, you're funny, you're cute. 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. 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, right? And I went, oh, man, that was. That's hard. That's deep. I don't know. And he goes, just think about it. And I'm like, where am I going to get six figures? I am. I came from nothing, absolutely nothing. Where, you know, we had to do some crazy things to be able to pay bills. Right? 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. Look, I had zero money to my name. I don't even know how to finance anything that's not a car or a house. Come on.

[Co-host (possibly Paul’s co-host)]

Right?

[Cassie Kenna]

Where am I going to get this money from? And he was like, listen, I'm going to help you. Here's the number 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. I needed one person to take a chance on me. One person. And he did, and I purchased it. So we started this process of purchasing the agency. And I was pregnant. I was going through ivf.

[Co-host (possibly Paul’s co-host)]

Wow.

[Cassie Kenna]

Okay. 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? I delivered my daughter in the hospital on 127 22. I was in class for the agency takeover the very next day.

[Paul Alex]

Wow.

[Cassie Kenna]

I never took maternity leave. And I purchased the agency officially in my name, March 1st.

[Co-host (possibly Paul’s co-host)]

Wow.

[Cassie Kenna]

So all my clients knew my daughter. Yeah. Right. So here I am with this six figure debt, A new baby, a new venture, new life. Scared as hell. It was crazy. But I took that. Mm. And I changed the way that people saw me. And insurance.

[Co-host (possibly Paul’s co-host)]

Absolutely.

[Cassie Kenna]

And once I figured out. And again, paying attention, right? People come in. What are they complaining about? What's the problem? What are they? You just have to listen. You have to listen to people. And they will tell you what they need. They will tell you what they want. That's. That's the key to life. Just listen. And so I did, and I scaled it 400%.

[Co-host (possibly Paul’s co-host)]

I love that.

[Cassie Kenna]

And I ascend. I mean, I look back now, it was the greatest, greatest adventure. The hardest, the most stressful. Because you're the boss. You have bills to pay, you have.

[Co-host (possibly Paul’s co-host)]

You have overhead expenses, you have the liability.

[Cassie Kenna]

Yeah. Well, and for me, it was the team. Like, I have mouths to feed in my office. I can't let them down.

[Co-host (possibly Paul’s co-host)]

Correct.

[Cassie Kenna]

And so 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.

[Paul Alex]

You were able to exit.

[Cassie Kenna]

I did, I did. So I exited. And my boss now was like, I need you because we want to shape like your mindset, your drive, what you stand for. That's what I want. I want that woman. And I'm like, okay.

[Paul Alex]

I think it's, I think it's very.

[Co-host (possibly Paul’s co-host)]

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.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

You know, you should consider doing a consulting agency if you're not already.

[Cassie Kenna]

Well, that's how I started. Yeah, I mean I, and I told him because he tried and I was like, I don't know, like I don't know. Right. What, what is my future? I don't want to make the wrong decision.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

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.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

And then he was like, and no, I don't want that. I want you.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

Oh, okay, that's good. I'll take it. That's good.

[Paul Alex]

So what would you say to someone.

[Co-host (possibly Paul’s co-host)]

Who is looking to break into insurance right now? Basically take your footsteps and try to eventually be able to have enough to buy an insurance agency or company and then scale that. 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 boot.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

Going into insurance, what would be three big needle movers that you would give them as advice?

[Cassie Kenna]

Well, so first off, you need to, I mean social media is huge nowadays. Right. And just about every insurance agency has a TikTok, has a Instagram, has a Facebook, something you need to look and I mean shoot me a dm.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Right. Because I'll get you. Who, what, when, where, how and why. You need to find an agent that fits in your core values. Right. As soon as you find that person that you can, 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. 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 and it's hard. 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, find that one, right? And then set yourself a list, right? You need to write out, here's where I'm at. 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 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 message. How are you going to be different than the Joe Schmo that you're watching as a mentor? Right? And so as soon as you have those, 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. This is how you determine if you're going to purchase an agency. You're going to start one by yourself. Those are two very different things. One's very expensive and one's really expensive and really stressful. Yeah, right. Because purchasing an agency is actually easier than you think.

[Co-host (possibly Paul’s co-host)]

Wow.

[Cassie Kenna]

Because they're for sale all over.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Right. And then once you find that, 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? What's their roi, what's their turnaround, what's their profit and loss. 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.

[Co-host (possibly Paul’s co-host)]

Yeah.

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Who knew?

[Cassie Kenna]

So I would say, I mean, DM me, obviously, right?

[Co-host (possibly Paul’s co-host)]

Where can they DM you?

[Cassie Kenna]

DM me? Cassie_712020 or the Hot Mess Express 2 Ts on Instagram. But that's what I would tell them because you're going to want to find that person that's willing to educate you and help you with your goals.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

You have to. So those would be my. Those maybe three.

[Paul Alex]

I love that.

[Co-host (possibly Paul’s co-host)]

I love that.

[Paul Alex]

It has a lot to do with.

[Co-host (possibly Paul’s co-host)]

My core values of self education.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

Number one. Number two, finding a mentor.

[Cassie Kenna]

Yep.

[Co-host (possibly Paul’s co-host)]

Because as old school millennials.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

We never really use the word mentor.

[Cassie Kenna]

No.

[Co-host (possibly Paul’s co-host)]

It was usually a parent, a friend.

[Cassie Kenna]

A co worker, grandparent.

[Co-host (possibly Paul’s co-host)]

Grandparent.

[Paul Alex]

Someone who gave you advice and you.

[Co-host (possibly Paul’s co-host)]

Never really processed it as they're mentoring me.

[Cassie Kenna]

Right.

[Co-host (possibly Paul’s co-host)]

I feel like mentoring really is being used or was really put into place the last five years. And it's because social media want a mentor.

[Paul Alex]

Find a mentor.

[Co-host (possibly Paul’s co-host)]

Right. You got business gurus saying mentor, mentor. And I never thought of it, like, reflection. Once 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.

[Paul Alex]

I was like, aha.

[Pipedrive Advertiser]

Moment. Right?

[Cassie Kenna]

Yes.

[Paul Alex]

But that's later in life. What would you say is the biggest.

[Co-host (possibly Paul’s co-host)]

Needle mover for people currently, right now in the military that are trying to find, number one, purpose, and number two, what would you recommend they do to find that purpose?

[Gemini Credit Card Advertiser]

Let's go deep.

[Cassie Kenna]

Oh, this is deep. I love it. Okay, so 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. We have a purpose. And I have goosebumps because this is so, like, this is deep. So in the military, you are. Your purpose is to save America. It is to. You've dedicated your life whether you go on a combat zone or not. You have dedicated your life to keeping America safe. I truly 100% believe in that. When you get out and you go, okay, like, what's next? 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 debilitator to go from being needed, having a purpose, to going out and going, do I go sell shoes? Like, what do I do? I? And then the jargon in between. So military jargon is, you know, it's fun because it doesn't translate in the civilian world. And so they have all of these amazing skills that we had talked about, right? Yeah, you have all these skills, but they. Normal civilians are like, what does that even mean? Like, what did you do? You. Okay, you built. I don't, 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. Find, find what makes you happy, right? When you get on the. A job should not be a job, it should be a passion. Right? And so many military members get out and they're like, I'm gonna go be a cop because there's a purpose.

[Paul Alex]

Very true.

[Cassie Kenna]

Right? There's 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. And, and then they get in and they are so, so mentally not okay. They're 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 gonna go work construction. Okay, Sit down there. In every single state, okay. In every single state there is a veteran employment representative that can sit down with you. And they have been trained to go, okay, this is what you did in the military.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

Here's how it translates into the civilian world, right. You don't think you have that skill, but didn't you do X, Y and Z then? Yeah, you have that skill.

[Pipedrive Advertiser]

Right.

[Cassie Kenna]

And believe it or not, and I actually work for the state of Michigan in this situation. That's how I know this exists. They literally come out of that meeting going, I have my confidence back.

[Co-host (possibly Paul’s co-host)]

Right?

[Cassie Kenna]

Like, I'm gonna find a purpose.

[Gemini Credit Card Advertiser]

Yeah.

[Cassie Kenna]

It's gonna be okay. 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, here's what I really enjoyed in the military. How does that translate? Like, what other jobs do you think? Because again, military, you're so, you're close minded. You don't, you don't want to be. It's not kind of by choice, but it's more by. That's who we are, right? We have one mission, we have one purpose.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And so you kind of get that goggle vision lost in the sauce because.

[Co-host (possibly Paul’s co-host)]

You'Re so mission driven.

[Cassie Kenna]

Yeah, yeah, yeah. And so these people, they're, they're amazing and they pull, they pull it out of you. I mean, they'll make you cry. That's their job. Right. And they're gonna 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.

[Gemini Credit Card Advertiser]

And that's great.

[Paul Alex]

We all need that.

[Cassie Kenna]

Yeah.

[Paul Alex]

You know, that in itself is mentorship.

[Cassie Kenna]

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. Who got out and has done it. Right.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And I will say that very large portion of military members are amazing entrepreneurs.

[Co-host (possibly Paul’s co-host)]

Right.

[Cassie Kenna]

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

[Co-host (possibly Paul’s co-host)]

Oh, yeah. Oh, yeah. Everybody got a story.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

You know, I always get asked, well, what makes you guys so special? Us. Our story.

[Cassie Kenna]

Yeah.

[Gemini Credit Card Advertiser]

Who we are.

[Cassie Kenna]

Yeah.

[Co-host (possibly Paul’s co-host)]

Can never take that away from us.

[Cassie Kenna]

No. And turn around, be like, you're special too. You just gotta figure it out.

[Co-host (possibly Paul’s co-host)]

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

[Cassie Kenna]

No.

[Co-host (possibly Paul’s co-host)]

I love that. So for the viewers and the listeners, what would be some words of encouragement to have them level up in 20, 20, 25.

[Cassie Kenna]

Oh, gosh, don't give up. Embrace your mess ups. Embrace your, who you are as a person. Right. Your story is unique. And don't ever think, don't ever sell yourself short for the fact that your story is. 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, hey, what you went through may not sound bad to me, but how did it affect you? So figure that out, you know, and don't stop, don't let anybody tell you that, 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. Don't let them. Because that's, that's where you're going to fall.

[Co-host (possibly Paul’s co-host)]

Yeah.

[Cassie Kenna]

And you're just gonna be stuck.

[Co-host (possibly Paul’s co-host)]

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

[Cassie Kenna]

Oh, I'm on Instagram. Cassie, underscore seven one or. Yeah, seven 21. 2020. And then the hot mess express two T's on Instagram. And then Cassie Kenna on Facebook.

[Co-host (possibly Paul’s co-host)]

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

[Cassie Kenna]

Thank you.

[Paul Alex]

With that being said, guys, leave a five star review on Spotify, Apple Podcasts and YouTube. Thank you for allowing us to be.

[Co-host (possibly Paul’s co-host)]

Number one in entrepreneurship, number one in all categories.

[Paul Alex]

And we're going to try.

[Co-host (possibly Paul’s co-host)]

Well, not I never say try. I say we will be doing 5.

[Paul Alex]

Million downloads in September, guys, because of you, we're trying to go ahead and.

[Co-host (possibly Paul’s co-host)]

Shoot for the stars.

[Paul Alex]

With that being said, guys, my name is Paul Alex. This is the Level podcast. We'll catch you on the next one.

[Cassie Kenna]

Peace.

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