Can a career filled with wild turns—from pro skateboarding and MMA fighting to podcasting and stand-up comedy—offer lessons about resilience, reinvention, and the unexpected intersections with insurance?

In this episode of the I Hate Insurance Podcast, Rick and Parker Lindsey talk with Jason Ellis, a legendary former athlete and current podcaster and comedian, about his fascinating life journey and how it’s shaped his views on risk, sobriety, and authenticity. From humble beginnings in Australia to major success in radio and now stand-up comedy, Jason opens up about his personal evolution and the ongoing effort to stay grounded and help others.

The conversation shifts into the world of insurance with Rick sharing stories and insights from decades of working with high-risk clients. Together, they dive into the real-world consequences of bad insurance decisions, the problems with unnecessary settlements, and how the industry needs to change to better protect individuals and businesses alike.

Want to hear what a pro skateboarder-turned-fighter has to say about authenticity, bullshit detectors, and why insurance still gets it wrong? Tune in to this episode with Jason Ellis—it's bold, raw, and surprisingly insightful.

If you've enjoyed this episode of the I Hate Insurance podcast, be sure to leave a review and subscribe today!

Enjoy!

Key takeaways:

• How Jason transitioned from skateboarding to radio, MMA, and now stand-up comedy

• Why Jason believes showing up authentically is key to personal growth

• The consequences of settling claims unnecessarily

• How the legal system and aggressive lawsuits influence insurance decisions

• Why understanding the fine print of health insurance is crucial

• The impact of natural disasters on insurance and the failures of government programs

• And much more…

  
  

Guest Bio:

Jason Ellis is a retired professional skateboarder and MMA fighter turned podcaster and stand-up comedian. He hosted The Jason Ellis Show on SiriusXM for 15 years and now entertains fans through Hawk vs. Wolf, Awesome World, and live comedy. A New York Times bestselling author of I’m Awesome and I’m Still Awesome, Jason is also the founder of the wild MMA-meets-music festival, Ellismania.

Resources

XINSURANCE

Jason Ellis

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of I Hate Insurance podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this special Chopper Chat episode of the I Hate Insurance Podcast, Rick J. Lindsey takes to the skies once again—this time with Austin Freeman, co-founder of Freedom Golf Retreat. After a powerful exchange with Austin’s business partner Nafe Latu, Rick continues the journey to explore the mission, mindset, and momentum behind their growing vision.

The aerial conversation touches on what it really means to build something with heart, from retreats and community to legacy and leadership. While the chopper cruises above Utah’s dramatic landscapes, Rick also reflects on his experiences with local golf courses and real estate developments, including Victory Ranch, Red Ledges, and Wolf Creek.

From taxes and wildfires to Tiger Woods’ nearby course and the unique lifestyle of out-of-state property owners, the dialogue weaves in personal stories, entrepreneurial insight, and a no-nonsense take on the realities of high-altitude development.

If you've enjoyed this episode of the I Hate Insurance podcast, be sure to leave a review and subscribe today!

Enjoy!

Key takeaways:

• Why Rick believes integrity and action matter more than titles or credentials

• What makes Freedom Golf Retreat more than just a luxury escape

• Why flying a helicopter isn't just a thrill—it’s a powerful metaphor for trust and risk

• How Rick sees a deeper purpose in his podcast mission

• The value of building relationships that go beyond business

• Why it's worth taking time to reflect—even if you have to do it midair

• And much more…

Guest Bio:

Austin Freeman is an entrepreneur, connector, and dream builder with a passion for innovation, community, and personal growth. As the co-founder of Freedom Golf Retreat, Austin plays a key role in crafting experiences that unite high-performing professionals through purpose-driven events.

Resources

XINSURANCE

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of I Hate Insurance podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In this Chopper Chat edition of the I Hate Insurance Podcast, Rick J. Lindsey takes to the skies with Nafe Latu, co-founder and owner of Freedom Golf Retreat. As they fly over the Utah mountains, they share a candid, unscripted conversation about trust, character, and why business—especially in the insurance world—needs more face-to-face relationships and fewer scripted policies.

Rick reflects on why he prefers to work with people he's played golf with, how leadership shows up in everyday actions, and why the traditional insurance model has lost its soul. Through admiration for Nafe’s consistency, personality, and integrity, Rick delivers a powerful message about doing business with people who show you who they are—on the golf course and beyond.

If you’ve ever sat through a soul-sucking insurance meeting, share this with someone who gets it. This episode pulls back the curtain on today’s broken insurance model—and why restoring trust and relationships is the future of underwriting.

If you've enjoyed this episode of the I Hate Insurance podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

• What most people get wrong about the insurance industry

• How personal branding can lead to real impact and influence

• Why insurance should be about relationships, not fine print

• The value of going "outside the box" in business and risk management

• How Rick’s approach challenges conventional industry norms

• And much more…

Guest Bio:

Nafe Latu is a serial entrepreneur and connector with a passion for personal branding and authentic leadership. He is the founder of The Unbroken Community and co-founder of Freedom Golf Retreat, Fresh Fade Away Barbershop, Carve Construction, and The Beauty University. Known for his dynamic energy and visionary thinking, Nafe brings together top-tier professionals and thought leaders to create meaningful growth experiences. At the helm of Freedom Golf Retreat, he fosters a culture of innovation and community that inspires transformation in both personal and professional spheres.

Resources:

XINSURANCE

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of I Hate Insurance podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.