The Level Up Podcast w/ Paul Alex
Military Grit, Entrepreneur Spirit: Kassie Kennaugh’s Story of Fear, Freedom & Financial Breakthrough
15 Nov 2025
In this powerful episode of The Level Up Podcast w/ Paul Alex, we sit down with Kassie Kennaugh — Air Force veteran, mother of four, former firefighter, and the entrepreneur who built, scaled, and sold her own insurance agency before becoming President of a major insurance company. Kassie’s journey is a raw, emotional blueprint of resilience. From facing trauma, depression, and self-doubt… to losing 150 pounds, rising through the ranks, taking on six-figure debt, scaling her agency 400%, and exiting successfully — her story is the definition of grit, purpose, and transformation. Today, she breaks down: 🔥 How military discipline shaped her entrepreneurial mindset 🔥 The moment she stopped letting fear dictate her life 🔥 What it takes to scale an insurance agency the right way 🔥 The power of mentorship and finding your purpose after the military 🔥 How to turn pain, pressure, and past trauma into fuel for your future This episode is for anyone who’s ever been counted out, underestimated, or stuck in survival mode — Kassie’s story proves that your past doesn’t define you… but your choices do. Connect with Kassie: 📸 Instagram: @kassie_712020 🔗 https://www.instagram.com/kassie_712020/ If Kassie’s story inspires you, make sure to share the episode with someone who needs it. Your Network is your NETWORTH! Make sure to add me on all SOCIAL MEDIA PLATFORMS: Instagram: https://jo.my/paulalex2024 Facebook: https://jo.my/fbpaulalex2024 YouTube: https://www.youtube.com/channel/UCGhDAD1JyGGzSQUPD9lc9HQ LinkedIn: https://jo.my/inpaulalex2024 Looking for a secondary source of income or want to become an entrepreneur? Check out one of my companies below to see if we can help you: www.CashSwipe.com FREE Copy of my book “Blue to Digital Gold - The New American Dream”:www.officialPaulAlex.com Learn more about your ad choices. Visit megaphone.fm/adchoices
Full Episode
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. 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. 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 gonna stop letting fear dictate your future
Guys, welcome back to 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. 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?
Yes, sir.
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. And you guys are going to love this. She's president and owner of an insurance company for the past 14 years. This insurance company is massive, by the way. Okay. 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. 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. Okay. Thank you for your service. 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. It's about leveling up. Welcome to the show.
Thank you for having me. I'm so excited.
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