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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
This Level Up podcast episode features Brianna Mathiesen, who built Miami's number one health insurance office from the ground up, starting by training agents out of her apartment. Brianna shares her remarkable journey from a college graduate wanting a gap year to building a team that has closed over $60 million in sales. The conversation explores how she transformed personal tragedy—including losing her mother and several family members—into fuel for creating a purpose-driven business that prioritizes helping people over profits. (02:07)
Main themes:
Brianna is the leader of Miami's number one health insurance office and a powerhouse in the insurance industry. She started her entrepreneurship journey as a gap year after graduating from the University of Miami in May 2018, initially planning to attend law school. Despite having traditional parents who wanted her to become a doctor or lawyer, she discovered the concept of residual income and built her business from her apartment, training agents in her living room before establishing a formal office in March 2020.
Paul Alex is the host of the Level Up podcast, a former detective and police officer with the Oakland Police Department who transitioned into entrepreneurship. He overcame significant personal challenges including PTSD, depression, and health issues to build multiple businesses and become a business consultant, authoring a book about his transformation journey.
Brianna emphasizes that putting all your eggs in one basket—even a successful career—sets you up for emotional instability. (16:23) She tells her team members that they need to be good sons, boyfriends, friends, and maintain their spiritual and physical health. This way, if one area suffers, they still have multiple sources of identity and self-worth. The key insight is that when you're constantly working on every aspect of who you are, you never feel like a complete failure because you're still winning in other areas of life.
The biggest mistake beginners make in insurance is focusing on money instead of helping people. (31:03) Brianna explains that health insurance isn't a sale—it's a necessity, and people can sense when you're genuinely trying to help versus just making money. When you prioritize understanding client needs, listening to their conditions, and providing genuine care, especially during vulnerable moments like job loss or family illness, the financial success follows naturally and sustainably.
While motivation is temporary, discipline creates lasting success. (10:28) Brianna stresses that when motivation wears off, your habits must continue to be routine. The most successful people maintain the same productive habits on their worst days as they do on their best days. This emotional consistency means you control the outcome rather than waiting for good days to make money, because those good days may never come if you let emotions dictate your behavior.
The number one trait Brianna looks for in successful team members is coachability. (10:27) She provides a proven system, high-quality leads, scripts, and comprehensive training, but success depends entirely on following the guidance. She wants success for her team members more than they want it for themselves, but this only works when people are willing to listen and implement feedback. Coachability extends beyond work—she even monitors team members' gym attendance and eating habits as part of holistic development.
When facing doubt or difficult times, Brianna relies on prayer and consistent positive habits. (33:54) Having lost multiple family members including her mother, aunt, uncles, and grandparents, she's learned that adversity can either break you or build resilience. Her approach includes working out, reading, journaling, spending time in nature, and remembering the people who depend on her. The key is developing small, consistent habits that work for you rather than against you, especially during challenging periods.