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.

Think you’re covered by your umbrella policy? You might want to take a closer look. In this eye-opening episode of the I Hate Insurance podcast, Rick and Parker Lindsey expose how most insurance policies—especially personal and umbrella coverage—aren’t actually protecting buyers the way they think.

What starts as a breakdown of umbrella policies turns into a broader conversation about the dysfunction in today’s insurance industry. From shifting liability to carving out endless exclusions, most companies are designing products that leave individuals and business owners dangerously exposed. Rick and Parker don’t hold back—they challenge the system, call out weak policies, and explain how to build true protection by aligning interests, simplifying coverage, and taking full responsibility for your risk.

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 most umbrella policies today are misleading and insufficient

• How modern insurance policies are structured to avoid risk—not cover it

• What true umbrella coverage used to look like (and why it worked)

• The dangerous trend of shifting business risks back onto the individual

• Why separating every kind of liability into different policies is a trap

• The role of the buyer in feeding the broken insurance system

• How to align legal and insurance interests to avoid expensive litigation

• What buyers can do right now to stop wasting money on ineffective coverage

• Why the best defense is a comprehensive, no-excuses plan that actually works

• And much more…

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.

What happens when you ditch the studio and take the podcast to the skies?

In this episode of the I Hate Insurance Podcast, host Rick Lindsey takes flight—literally—for a candid, unscripted conversation with The Collector.

Set in a helicopter flying over the Utah mountains, the conversation weaves through a wide range of topics: the broken incentives in insurance, the hidden value in salvage, building shooting ranges, vetting firearms policies, and the frustrations of dealing with clueless lawyers and adjusters. With no pretense and no filter, Rick lays out his unapologetic views on why the system is broken and how common sense—not bureaucracy—should drive decision-making.

From ATV stories and elk hunting to policy loopholes and hurricane recovery, this episode is part rant, part wisdom, and part altitude-induced adrenaline. If you’re tired of insurance talk that dodges the truth, this one hits hard—with rotor blades whirring in the background.

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 salvage partnerships can save millions when handled with logic

• Why insurance policies are often designed to fail the insured

• The hidden problem with separating personal and business policies

• What firearm liability coverage should really include

• Why insurance companies keep feeding the legal system instead of fixing it

• The real reason catastrophe claims should be paid faster

• How common sense and real-world risk-taking beat outdated industry standards

• And much more…

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 the 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.

What happens when a seasoned insurance professional gets honest about everything wrong with the industry?

In this episode of I Hate Insurance, Rick and Parker Lindsey sit down with Steve Beultel for an honest conversation about why insurance is broken—from the convoluted process of underwriting to claims that make customers feel more like liabilities than partners.

Steve shares decades of front-line experience, breaking down how bad incentives, poor communication, and a culture of “saving money” over delivering value have led to widespread frustration on all sides of the table. But it’s not all doom and gloom—Steve and Rick explore what good insurance could and should look like, emphasizing transparency, partnership, and common sense over red tape.

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:

• Why trying to “save money” on insurance often leads to bigger problems

• What needs to happen to fix the broken broker–underwriter–carrier pipeline

• How to spot a bad deal (and what a win-win actually looks like)

• What agents should really be doing if they want to serve clients with integrity

• Why common sense beats industry jargon every single time

• The real danger behind sloppily sold policies

• How Steve’s approach to partnership changes the claims game

• What new insurance professionals need to know about educating themselves

• And much more…

Resources

XINSURANCE website

I Hate Insurance Podcast Youtube channel

Are waivers really worth the paper they’re written on? In this episode of the I Hate Insurance podcast, Rick and Parker Lindsey break down the real value of waivers, whether they actually protect businesses from lawsuits, and what makes a waiver legally enforceable.

Rick and Parker dive into common misconceptions about waivers, why early claim reporting is critical, and how the legal system can take advantage of businesses that lack strong defense strategies. They also discuss the difference between gross negligence and ordinary negligence, explaining how business owners can better protect themselves with strategic partnerships and well-written policies.

If you’ve ever wondered how to use waivers effectively or why traditional insurance often fails businesses, this episode will give you a brutally honest look at the industry and how to navigate its pitfalls. Enjoy!

In This Episode You'll Learn:

• What most business owners get wrong about waivers—and how it could cost them

• How the legal system really views waivers (it’s not what you think)

• The difference between ordinary negligence and gross negligence—and why it matters

• Why early claim reporting could be the most important decision you make

• How insurance companies protect themselves first—leaving businesses exposed

• What makes a waiver enforceable (and what makes it useless)

• Why traditional insurance isn’t built to truly defend policyholders

• How to structure risk management strategies that actually hold up in court

• And much more…

Sign up for emails and see exclusive content on the I Hate Insurance Podcast website: https://www.xinsurance.com/i-hate-insurance-podcast/

Resources

Seanz V Whitewater Voyages

What does it take to bet on yourself, defy expectations, and carve out your own path? In this episode of the I Hate Insurance podcast, hosts Rick and Parker Lindsay sit down with Trey Sprinkle, the man behind the popular Last American Outlaw YouTube channel and founder of Echo Mav Technologies.Trey’s journey is anything but ordinary. After experiencing bankruptcy during the 2008 housing crisis, he rebuilt his career in insurance claims and storm management, only to later walk away from it all in pursuit of something bigger. From working in insurance to training the military, traveling to Ukraine, and launching his own drone technology company, Trey’s story is one of risk, resilience, and relentless determination.In this episode, Trey opens up about the life-changing decision to spend his last dollars to attend SHOT Show, how he built his 900,000-subscriber YouTube channel, and how his military collaborations led to cutting-edge drone development for the U.S. Army.This conversation is about pushing past fear, making bold moves, and creating opportunities where none exist. Enjoy!In This Episode You'll Learn:Why setbacks like bankruptcy don’t define you—your response doesThe power of connections: How one event changed Trey’s entire trajectoryHow risk-taking separates high achievers from those who stay stagnantWhy Trey walked away from a successful insurance career to chase a bigger vision.The future of drone warfare and why Echo Mav Technologies is changing the gameHow embracing discomfort and challenges leads to personal and business growthAnd much more…

Resources

Last American Outlaw YouTube Channel

Connect with Trey on LinkedIn