One Hale of a Podcast

One Hale of a Podcast is hosted by Partner Patrick Hale and Partner Patrick Iyampillai of Hale Law. Each episode features conversations with local leaders, innovators, and changemakers who are making a difference in our community—whether through their businesses, their service, or their stories.

One Hale of a Podcast Won Gold in the 2026 Best of SRQ Local Awards

Episodes

Sep 16, 2026

38 min

Mental Health Matters After Military Service Not every wound comes home visible. In this episode, we sit down with Kendra Simpkins. She's a U.S. Army veteran, CEO of Operation Warrior Resolution, and the 2019 to 2020 Sarasota County Female Veteran of the Year. Kendra takes us through her time in the Army, what she carried with her after being discharged in 2010, and the gap she found in veteran mental health care once the uniform came off. That gap is what pushed her toward the education, training, and drive that became Operation Warrior Resolution.
We get into what Operation Warrior Resolution actually offers, why Kendra's approach goes beyond traditional talk therapy, and what's next for the organization. That includes an upcoming new facility built around community and green space, designed to serve as a mental health retreat for veterans.
Of course, we don't stop at the serious stuff. We play a round of Florida Man (two fake headlines, one real, can you guess it?), talk local favorite restaurants, coffee spots, and hiking trails, and Kendra shares a piece of advice for any veteran who feels stuck right now.
 
🎖️ A story of service, struggle, and purpose, and a mission that's still just getting started. Listen to this podcast today on all major listening platforms!
 
***Medical, TBI, & Crisis Disclaimer: This episode features open discussions surrounding mental health, post-traumatic stress disorder (PTSD), and traumatic brain injury (TBI) trauma. The information, opinions, and stories shared in this video are for educational, informational, and entertainment purposes only. This content is not a substitute for professional medical advice, neurological evaluation, psychiatric diagnosis, or mental health treatment. Always seek the advice of your physician, neurologist, mental health professional, or other qualified healthcare providers with any questions you have regarding a medical condition, brain injury, or psychological trauma. Never delay seeking professional care because of something you heard on this show. Crisis Resources & Immediate Support: National Suicide & Crisis Lifeline: Call or text 988 (Available to anyone). Veterans Crisis Line: Dial 988, then Press 1, or text 838255 (For veterans and service members). Online Chat: Visit VeteransCrisisLine.net. Brain Injury Resources: If you are seeking specialized information on brain trauma, contact the Brain Injury Association of America at 1-800-444-6443.

Sep 16, 2026

38 min

Sep 2, 2026

52 min

A Law Firm's Mission is Important in Practice A mission statement means nothing if the values behind it aren't real.
In this episode, we're joined by Jason Miller, founder of Miller Litigation, and Rose Gwynn, marketing strategist for the firm, for a conversation about what it actually looks like to build a company around real core values and how those values shape a company's mission, not just its marketing. Jason talks about managing Miller Litigation and how those values drive the way he runs the business day to day, while Rose brings the marketing perspective on why core values matter so much and what it really means for a company to be mission-driven. We also get to know Jason and Rose a little better:
Jason talks motorcycles, Rose talks about her creative side, and of course we couldn't do an episode without our rapid fire questions and a Florida Man segment. Legal insight, real conversation, and a little bit of chaos, as always.
🏍️ Motorcycles, core values, and marketing this one's got it all. Listen to this podcast today on all major listening platforms!

Sep 2, 2026

52 min

Aug 19, 2026

38 min

Our first-ever virtual guest takes us straight to the bayou! David Vicknair of Scott Vicknair Injury Lawyers joins us from New Orleans, Louisiana — a firm Hale Law deeply admires and trades ideas with often.
 
We get to know David: his background, his philosophy, and what it's like running a firm in a different community with a whole different culture. Along the way we explore how the law is similar yet different across state lines, hear about a few of his New Orleans favorites, and throw in a Florida Man and a Louisiana Man story just to keep things interesting.
 
Listen now on all podcast platforms, or watch on YouTube.
 
Check out Scott Vicknair Injury Lawyers at scottvicknair.com.

Aug 19, 2026

38 min

Aug 5, 2026

38 min

In this episode of One Hale of a Podcast, Patrick Hale sits down with Annie Cobb-Trudell of the Big Bill Foundation.
Annie shares her background, how she got into race management, and the mission behind the foundation's work in Southwest Florida. She talks about the community runs they host, the scholarships they award to kids who have overcome childhood cancer, and the new races coming down the road. This one ties right back to our Sarasota community — and it's a conversation you don't want to miss.
Listen to this episode now on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts.

Aug 5, 2026

38 min

Jul 27, 2026

1 hr 4 min


Recording artist. Attorney. Mediator. Life coach. Sound bath practitioner. Tara Gess has had one of the most unexpected career paths you'll hear about — and on this episode of One Hale of a Podcast, host Patrick Iyampillai gets the whole story.
 
Tara is the owner of Gess Mediation and a Florida Supreme Court Certified Circuit Civil Mediator. But before the courtroom, she was chasing a music career in Nashville. In this conversation she walks us through every pivot: what performing taught her about people, why she traded the stage for law school, and what eventually pulled her out of practicing and into mediation, and what truly makes a good work-life balance.
 
🎙️ New episodes every other week.
 
Connect with Tara Gess | Gess Mediation | https://gessmediation.com/
 
One Hale of a Podcast is brought to you by Hale Law Accident Attorneys — Gold Winner, Sarasota Magazine's 2026 Best of SRQ Local. Learn more at https://www.halelaw.com

Jul 27, 2026

1 hr 4 min

Jun 24, 2026

37 min

In this episode, we sit down with Michael Freedman from the Venice, FL chapter of the AACA — the Antique Automobiles Club of America. Michael gives us a look inside his personal collection of classic cars, what it takes to organize and run a car show, and what makes Cars & Coffee such a staple in the community. We also get into the partnership between the AACA and Hale Law and how both organizations are showing up for the people of Venice and beyond. And if you stick around long enough… we get into his award-winning chili recipe. You're not going to want to miss that part.
 
Whether you're a classic car enthusiast, a community event regular, or just someone who appreciates a good conversation with even better people — pull up a seat. This one's a great listen.
 
Listen now on YouTube, Apple Podcasts, Spotify, or your favorite podcast platform.
 

Jun 24, 2026

37 min

Jun 10, 2026

30 min

This episode is all about compassion, second chances, and the incredible impact of animal rescue.
 
Partner Patrick Hale and Partner Patrick Iyampillai sit down with Connie Boros from the Humane Society of Sarasota County, who also brought along a very special furry guest, Milky Way!
 
Connie shares her journey to Sarasota, what inspired her passion for animal welfare, and how the Humane Society works to help animals find loving homes. The conversation dives into real shelter stories, unforgettable rescue moments, and the heartwarming experiences that make this work so meaningful.
 
Whether you're an animal lover, considering adoption, or simply enjoy hearing inspiring stories about people making a difference in the community, this is an episode you won't want to miss. And keep an eye on Milky Way throughout the episode—you might catch some calm (and adorable) chaos happening behind the scenes.
 
🎙️ Listen now on YouTube, Apple Podcasts, Spotify, or your favorite podcast platform.

Jun 10, 2026

30 min

May 27, 2026

31 min

Bringing the Heat On and Off the Field 
 
In this special Hot as Hale edition of One Hale of a Podcast, things get spicy as USF football alumni Christian Helms joins the show for a challenge unlike any other. The rules are simple: answer 10 hard-hitting questions truthfully… or add even more hot sauce to your taco. 🌮🌶️
 
Throughout the episode, we dive into Christian’s life on and off the football field, his experiences as a USF athlete, and what life looks like beyond the game. Along the way, Patrick Hale also shares some of his strongest lawyer hot takes, leading to plenty of hilarious and unexpected moments.
 
From football stories to uncomfortable questions and spicy consequences, this episode brings the heat from start to finish.

May 27, 2026

31 min

May 13, 2026

35 min

Who Let the Dogs Out? 🐾
 
This episode of One Hale of a Podcast is bringing the energy—and the puppies. We sit down with Rob Oglesby, Director of Development at Nate’s Honor Animal Rescue, who joins us with two special guests, Mochi and Eggroll.
 
Rob shares his journey into the rescue world and how he became a driving force behind one of the most impactful animal rescues in our community. From unforgettable rescue stories to his favorite moments on the job, this episode is full of heart.
 
We also dive into the exciting future of Nate’s Honor, including their new facility and how it will expand their mission to save more animals and connect them with loving homes.
 
If you love dogs, community, and stories that make a difference, this is one you don’t want to miss. 🐶
 

May 13, 2026

35 min

Apr 29, 2026

28 min

We’re back—and better than ever.
 
In this kickoff episode of One Hale of a Podcast, Co-Managing Partners Patrick Hale and Patrick Iyampillai sit down to welcome you into Season 2 and give you a preview of everything ahead. From a brand-new setup to exciting new guests and unforgettable stories, this season is all about leveling up.
 
They also take a moment to reflect on what’s been happening at Hale Law—both personally and professionally—sharing real updates, behind-the-scenes moments, and what’s driving the firm forward.
 
Most importantly, this episode is about getting to know the people behind the firm. The conversations, the mindset, and the mission that fuels everything they do.
 
We’re ready to kick off a new season full of amazing memories—and you won’t want to miss what’s coming next. 🎧

Apr 29, 2026

28 min

Patrick Hale and Patrick Iyampillai

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