Dan Lennon (The Benefits of a Second Career, Firefighter Fitness and Honouring the Fallen) - Episode 1157

Behind The Shield

James Geering

Health & Fitness, Mental Health, Fitness

4.9 • 667 Ratings

🗓️ 2 November 2025

⏱️ 137 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Dan Lennon is a U.S. Air Force veteran, Lieutenant with Orange County Fire Rescue, and the founder of The First Responder Realtor® brand. We discuss his journey into the fire service, firefighter fitness, the fiscal and mental health benefits of a second career, the world of real estate and so much more.

With over 17 years in the fire service, Dan has built his career and his business around one guiding principle — “relationships before business.” After years of serving his community on the front lines, Dan turned his passion for service toward real estate. He’s a proud member of eXp Realty’s Gwilt Group, a military-led team dedicated to serving those who serve — including first responders, veterans, and their families. Dan helps buyers, sellers, and investors across Central Florida navigate the market with trust, transparency, and integrity.

He’s also the co-founder of F.I.R.E. Flips, a business he runs with retired firefighter Anthony Kibler, specializing in purchasing and restoring fire-damaged homes for people looking to sell — transforming loss into renewal. Beyond that, Dan leads Trapelo Road Investments, inspired by his family roots in Waltham, Massachusetts, where he focuses on long-term development and wealth-building opportunities across East Orlando.

Whether he’s running calls with Orange County Fire Rescue or helping a client close on their dream home, Dan brings the same sense of duty, discipline, and heart to everything he does. His mission is clear — to serve those who serve, and to help others build lasting freedom through real estate.

https://www.instagram.com/dan_lennon_realtor/?hl=en

Transcript

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0:00.0	Welcome to the Behind a Shield podcast. As always, my name's James Gearing, and this week it is my
0:04.0	absolute honor to welcome on the show, veteran firefighter and realtor Dan Lennon. Now, in this
0:11.7	conversation, we discuss a host of topics from Dan's journey into the fire service, the importance
0:17.8	of firefighter fitness, the brother and sisterhood at the 343 Hero Challenge,
0:23.7	how a side profession can not only give financial security, but also help with the transition
0:29.1	out of the fire service, the 2472, and so much more.
0:34.9	Now before we get to this incredible conversation, as I say every week,
0:38.5	please just take a moment.
0:40.6	Go to whichever app you listen to this on.
0:43.0	Subscribe to the show, leave feedback, and leave a rating.
0:47.7	Every single five-star rating truly does elevate this podcast,
0:52.0	therefore making it easier for others to find. And this is a free
0:56.1	library of over 1,100 episodes now. So all I ask in return is that you help share these
1:03.8	incredible men and women's stories so I can get them to every single person on planet Earth
1:09.9	who needs to hear them.
1:11.6	So with that being said, I introduce to you Dan Lennon.
1:17.6	Enjoy.
1:49.6	Enjoy. Well, Dan, I want to start by saying thank you so much for first of your patients, because we tried to do this yesterday and my computer basically took a shit so we had to reschedule and do it today so I want to thank you again for coming on the Behind the Shield podcast yeah man thanks for having me super excited to do it
1:55.9	and you know my son's my oldest son he met you at the 343 and I told him I was doing a podcast, and he was like, is that the guy that interviewed James Brolin? And I was like, yeah. So, like, because of you, my kids think I'm like some type of famous person, but I told him, I'm like, nobody knows who I am. So it's okay. But I appreciate it. you're popping me already well that was so cool we'll
2:20.9	soak around to it again but this last year I've done the 343 I think this was the 11th year if I'm not
2:27.0	mistaken um and uh you did it with your son uh Dave Coughlin did it with his son so you know 10 know, 10 plus years ago, we were doing it, and then we were losing a lot of people.
2:37.8	And obviously, there was a very poignant backstory to, you know, the bonus wads and all those kind of things.
	...

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