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.