Activation Time: Christopher Gandy's Vision for NAIFA & Empowering the Financial Services Community

You are about to meet NAIFA's new president, Christopher Gandy, a former professional basketball player turned powerhouse in the financial services industry, on this special edition of Pathways e3 with Amber Stitt. 🚀

In this episode, Christopher Gandy shares his journey from the courts to becoming NAIFA’s president, his bold take on leading change, and why excitement and community are the real game-changers in business. 🏀

From activating others to building a lasting legacy, he’s on a mission to uplift the industry and empower you to take action.

If you’ve ever wondered how to be the catalyst for transformation—whether in your organization or your own life—this conversation is your rally cry. 

Let’s talk about leadership energy, human connection, and building momentum that lasts. 🌟

Ready to make a difference? Hit play and join the movement!

📽️ To watch this episode:  https://youtu.be/Z2iw8qM3iOQ

🔗 To connect with Christopher Gandy: 

📲 Website: https://tlwgllc.com

📲 LinkedIn: https://www.linkedin.com/in/christopher-gandy-lacp-60779413

📲 Instagram: https://www.instagram.com/coach_cgandy

#pathwayswithamberstitt #christophergandy #amberstitt #givingback #tlwgllc #insuranceindustrymentorship #insurancecoach #naifae3 #amberstittmediacompany 

📻 Thank you for tuning in to Pathways!

🔗 Connect with Amber on Social Media:

• AMBER’S INSTAGRAM
• AMBER’S LINKEDIN
• AMBER’S FACEBOOK

📲 Be sure to visit Amber's website:

www.AmberStitt.com

🎬 And remember, let's take action today!!!

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Transcript

Christopher Gandy [00:00:00]:
We have to remember that we're human beings behind all this and that we have to take care of each other. If we start with that, and curiosity, and we care for each other, we can do anything. I think if we start with that, everything else is possibilities for us. And so, my cry is that as an organization, we show up better. We're present for each other, we support each other, we uplift each other. That's important. And now it's time for us to activate each other. Most people have stood in the shadows, "Well, I did my part."

Amber Stitt [00:00:34]:
Yeah.

Christopher Gandy [00:00:35]:
But now it's time for us to activate each other. And so when your number is called, and I will be calling numbers, "Hey listen, remember, I need your help."

Amber Stitt [00:00:44]:
Hello and welcome to Pathways e3, a special edition of Pathways with Amber Stitt. The Pathways e3 podcasts were recorded with special guests who were attending and collaborating at the NAIFA e3 conference in Newport Beach, California in September 2025. Let's join the conversation.

Amber Stitt [00:01:04]:
We are live at NAIFA e3, and

Amber Stitt [00:01:06]:
I'm so excited to finish our podcast

Amber Stitt [00:01:08]:
series this week at this amazing conference with Christopher. So thank you so much for being here.

Christopher Gandy [00:01:13]:
It is a pleasure being here.

Amber Stitt [00:01:15]:
And I was quite bummed, I had to miss, I was fortunate enough to podcast today, but I missed you on the main stage talking today.

Christopher Gandy [00:01:22]:
Yeah.

Amber Stitt [00:01:23]:
But I think everyone gets a chance to hear it now. You and I are going to talk about it.

Christopher Gandy [00:01:27]:
So let's talk about it.

Amber Stitt [00:01:29]:
You are going in as the next president of NAIFA, correct?

Christopher Gandy [00:01:34]:
Yes, I am.

Amber Stitt [00:01:35]:
And you're sighing. Oh, no!

Christopher Gandy [00:01:37]:
I had to take a breath.

Amber Stitt [00:01:38]:
Yeah, you know what you're getting yourself into. It's not the first time you've been up for a challenge.

Christopher Gandy [00:01:42]:
I'd like to say that the work is something that chose us, and it just aligns with what I'm feeling into at this point in this stage of my career. And what a better way to pour into thousands of people: vision, motivation, opportunity, and uplifting movement and spirit and all the fun stuff that makes life worth living. So that's what we're going to do. That's what we're going to have fun doing in 2026, to create that momentum, to create that excitement around who we are and where we came from and why it's great to wear these type of jerseys nowadays, that type of thing.

Amber Stitt [00:02:22]:
Not your first time, so from the court to the industry.

Christopher Gandy [00:02:25]:
Yeah.

Amber Stitt [00:02:25]:
The theme behind the conference is really empowerment, collaboration. So you've been talking about a catalyst and so I thought it's beautiful to have you at the very end because this is where anyone who's listening to the episodes, or binging, and is going to move into this next phase of thought leadership. There's a rally cry that I missed today and so can you talk about that?

Christopher Gandy [00:02:45]:
I've done a couple different talks nationally and people have asked me one on the industry of how to run our prospects and sales and the 1%, how to be the 1% better every day, every way, that type of thing, how to just crush and exceed expectations. But I've never done one on "change." And one of my good partners and people I trust, we were having a conversation and I said, "I got it, I want to come up with a talk, 15 minute, really just motivation, identification, and about change." And he's like, "Is that really what you're trying to do, based on some of the things?" And the thought was that change, in our mind's eye, is easy to do, but it's difficult, right? And so if everybody can change, they would just do it. And it's like the mind, like we can't turn the mind off.

Christopher Gandy [00:03:42]:
If everyone's listening, just try it, right? Just sit in silence and stillness for a period of time and see what happens. Our mind races. So the idea was we need to become the catalyst of change and embody that and what that looks like, because that's different than just accepting and saying that we need to change. So the whole talk was really around where we came from, where we're at, accepting what's ahead of us, and everybody taking ownership of being a part of this family. And it's super important that we create community, we create accountability for each other, and we do that in a way where we could collectively all feel better for what we're doing, not only for ourselves, but for our communities and the people's lives that we touch on a day-to-day basis. When other people show up with bills, we show up with checks. And it's really difficult for, I would say outside people, to understand the work we do. But we allow people to live life with dignity and we allow people to be able to stay in their homes, we allow people to be able to put food on their tables, we allow for people, when life sometimes throws us a curveball, and our health changes, for them to be able to hold their head up high and still be able to live a quality of life that's human.

Christopher Gandy [00:05:03]:
And so we're excited about that. In that call, that cry for help, is that when your number's called, you got to be ready to go.

Amber Stitt [00:05:12]:
Yeah.

Christopher Gandy [00:05:12]:
Which is important.

Amber Stitt [00:05:13]:
You've been in leadership for a long time. Is there anything that you're really trying to push on that hasn't been done before in NAIFA, or the industry?

Christopher Gandy [00:05:22]:
Well, we can't talk about this on a podcast...I'm just kidding.

Amber Stitt [00:05:25]:
I know, right? I'm really, not so much...Is there anything that you are going to implement that is so important that hasn't been done before?

Christopher Gandy [00:05:33]:
Well, I think the role that I'm moving into is a role of very stoic, presidential responsibilities. And what I've said before is that excitement is contagious. And we can have some excitement. We can bring excitement back to the largest, oldest financial services association on the planet, which is NAIFA. We can bring that back, that excitement back to it. When people come to a NAIFA meeting, they can be excited about what's going to happen. So one of the things I did, is challenge everyone on that we need to create an experience.

Christopher Gandy [00:06:12]:
Every single time we engage with someone who is considering NAIFA, someone is a NAIFA member, it needs to be an experience. Because if you notice, if we take a step from here, forget NAIFA for the moment. Is that people are living their lives based on experiences, right? And so, how else do you end up in the middle of the Venetian forest swinging from a tree, because you watched it on Instagram, right? That type of thing. And so, if we can create that experience and underlie it with a current of excitement, the FOMO is real, right? And the excitement then trickles and people are like, "I want to be a part of that." One of the concepts I had, and I don't know if it's going to come to fruition, I'd like it to, because I think it'd be really exciting, was that when we start in 2026, let's take a caravan to the 5 largest NAIFA chapters around the country. And we film it, just like they do a caravan, like when someone's running for an office or something like that. Like, let's do that. Let's have some fun doing that.

Christopher Gandy [00:07:13]:
And we track it like it's on the NAIFA website at the bottom, "Hey, where are they in the world?" Whatever.

Amber Stitt [00:07:17]:
Maybe you guys could land at the D.C. thing?

Christopher Gandy [00:07:19]:
Yeah, that'd be so fun, right? And so picking up people along the way and having stories and having conversations and someone filming that and just having a good time, I think that would be so much fun and it'll be a unique experience. And what we do is, the idea was simple, is that the person that is a NAIFA loyalist in the area is identify where is our largest NAIFA contingency there, and where's the largest agencies, or financial advisory firms. And we go there uninvited, of course. We go there with the idea that, "Hey, we're going to show up and just love on you enough, so that at the end of the day you at least know who we are, you know we exist and you know why we're here." And so I think that is it. And slowly but surely momentum, momentum carries us forward.

Amber Stitt [00:08:04]:
You know what's really cool about that is we spent a lot of time this week talking about who's retiring and the numbers and the stats. You could hype up the industry by doing that.

Christopher Gandy [00:08:13]:
Yeah, yeah.

Amber Stitt [00:08:14]:
And that next generation can see that.

Christopher Gandy [00:08:16]:
The idea of...I was at a talk earlier and they asked how many people here plan on retiring in the next 10 years.

Amber Stitt [00:08:22]:
5 hands.

Christopher Gandy [00:08:24]:
You were in that talk? There was 5 hands that went up. But the average age of the actual advisors in the room is like 70.

Amber Stitt [00:08:29]:
So I'm not gonna call you out, but I see you.

Christopher Gandy [00:08:33]:
So the harsh reality is the majority of financial advisors, financial planners, and insurance professionals will never see the monetary value for their work and the sweat and the tears that they put into the business and pouring into other people's because they're never going to be rewarded for it. There's never in our business, unless you're a part of a collective, or group, or something like that. There's typically not a, what we call a financial incident, where someone comes and they say, "We'll give you 20X for your practice and you're done." There are some, but the majority of those firms don't exist. So unless we create an actual structure, a plan to do so, to exit, then it's going to eventually exit, whether it's under our conditions, or someone else's. So I just know in my practice, if something happens to me, the rule of thumb is that there's 2 years of revenue that comes from my practice if the person that inherits it does not have a license. And so if you do the math on that, if our practice say is worth on paper, let's call it $11, $12 million, and then say EBITDA is 5X that.

Christopher Gandy [00:09:46]:
Let's say it's worth $50 million. For someone to get 2 times the revenue for two years is ludicrous. And I don't think any financial professional would do that trade off if they had a choice. Given a choice.

Amber Stitt [00:09:58]:
Sure. So were you the one saying somebody was saying, I mean, at least 5, 10 years forward thinking. We got to start thinking about it now.

Christopher Gandy [00:10:07]:
Yeah. It's here.

Amber Stitt [00:10:07]:
Yeah.

Christopher Gandy [00:10:08]:
We're at the crossroads. And so we can't wait till it gets here. We can't wait. People spend more time packing for vacation than they do their exit. Doesn't make any sense, so...

Amber Stitt [00:10:15]:
Do the work, clean the house.

Christopher Gandy [00:10:17]:
Yeah, we can't wait till we get there to pack.

Amber Stitt [00:10:20]:
Thank you for joining us on this episode of Pathways. Please consider giving us a "Like" and subscribing to the channel. Your support goes a long way towards helping us bring you more compelling content. Remember, let's take action together! Now, let's jump back into the conversation.

Amber Stitt [00:10:39]:
Some people know you as an athlete, top producer. I don't know the origin story about how you got into the business.

Christopher Gandy [00:10:45]:
Sure, you want to hear?

Amber Stitt [00:10:47]:
I want to hear.

Christopher Gandy [00:10:48]:
I am actually a recovering athlete. That's my claim to fame. What I'd like to just preface and change the narrative of a little bit is I was an athlete that eventually landed in the financial services business, but I always kept athletics in a perspective that made it very honorable for me. Sports is nothing more than a dream with a deadline. It's eventually going to end whether we like it, or not. The majority of athletes don't retire because they can't do the sport anymore. The majority of athletes retire because they physically can't do it anymore. Or there's someone younger who can physically do it better.

Christopher Gandy [00:11:27]:
And so when you get to that place, you start to realize that what you do for a living is not who you are. And a lot of athletes have a real challenge and a difficult time separating the two. And in society, we treat them as such. And so, how do you unsee LeBron James as a professional basketball player? How do you unsee LeBron James as who he is? You'll always, kind of in your mind's eye, you say you see him as that, but he wakes up in the morning just like you and I. If I cut his wrist, he bleeds just like you and I. He has feelings just like you and I, he gets sick just like you and I.

Christopher Gandy [00:12:04]:
And so at the end of the day, one of the things that allowed for me to make that transition easier for me is I kept it in perspective. And then through my journeys of playing sports, I never let it define who I was and what I believed and the person that was underneath that. So I never did that. And so it was fun to kind of play in that shadow and say, "Hey, I'm an athlete." But the narrative is one that's simplistic in nature. It's like, I'll give you an example. It's like someone said to me about 4 or 5 years ago when DEI was important, or was not such a divisive word.

Christopher Gandy [00:12:42]:
Someone said to me that, "Hey, DEI is the reason why you may become president at some point." And I sat back, I said, is that...So I said, "Maybe it's just simply because I'm better than the other guy." I go, "What about that? What about I'm more intelligent than he is, I'm more of a thought leader than he is, and I'm actually a better financial service professional than he is. And I actually run an organization, I don't work for somebody and I actually make those financial decisions all the time. And I understand, top down, I understand how to build a process versus a system. I understand it's not personality driven, it's process, or procedure. I have that part in me, too."

Christopher Gandy [00:13:14]:
And they're like, "Okay, we get it." And so changing that narrative a little bit is super important. But it was a blessing. It was, it was a beautiful thing for me to play a kids game and get paid to do it.

Amber Stitt [00:13:27]:
Was there ever a point early in your, we'll call it sales career, where you were up...maybe like a blooper reel. What's a funny story that you would like a younger person to know? Like, "You gotta hear this." Is there anything top of mind? You're like, "Ugh, There was this one time."

Christopher Gandy [00:13:41]:
Oh, which one time? I was...

Amber Stitt [00:13:45]:
On the come up. Anything? You were just like, "Oh, man, you gotta hear this."

Christopher Gandy [00:13:48]:
I wrote an insurance policy for someone and got chased by a dog. I had to jump over a fence. I had that. I showed up to a lady's office and she decided that she wanted to give birth. That happened.

Amber Stitt [00:14:00]:
She decided just at that time.

Christopher Gandy [00:14:01]:
Yeah, "We gotta go now." That happened. I mean, I could give...I remember I went to this lady's house, she was probably 75 years-old. She's like, "I really want to do Business with you." And I'm like, "Okay, great." She's like, "But you have to eat my apple pie." I'm like, "Okay, great."

Christopher Gandy [00:14:17]:
Well, I got there at like, 10 in the morning and I left at like, 11 at night because she had to make the apple pie. But the apple pie didn't come before she had to make dinner. And it was just a series of different things. And the best story ever was I went to go see a guy, when I first started, and they were like, "You got to work with business owners!" And so because I did play sports in a town like the University of Illinois, people kind of knew me, but they didn't know me, they knew of me. They didn't know me, Chris Gandy. And so I called up this guy and I said, "I want to introduce myself.

Christopher Gandy [00:14:49]:
I know you might remember me. I played here. And now I've entered into a new game. I'm building what they call the 'Financial Playbook: The True X's and O's on Actually Building a Successful Game Plan.' I'd love to talk to you and your business about it." He's like, "Well, come on over." I said, "Okay, great." So I go over, interesting story.

Christopher Gandy [00:15:07]:
I go over to see him, and after we talk, I tell him why it's wonderful, "Here's the type of plans you should do, blah, blah, blah." And I'm feeling really good, really excited. And he's like, "You know what? We're going to do business together." And I'm like, "Sweet!" And in my mind's eye, business owners could do $10K of premium, or more. So I was super excited because that would have been the largest case I've ever had.

Christopher Gandy [00:15:28]:
And then he goes, "Come on back to my office." So I sat down with him. He has this desk that's probably the size of this table. It's huge. And he sits back and puts his feet on his desk. And he pulls out this bag, sets it on the table. He goes, "You know what that is, young man?" I go, "No." He goes, "Put those papers away."

Christopher Gandy [00:15:45]:
He goes, "We're going to do business the way I like to do business." I said, "Okay." He pulls out this bag. There's a cigar. He pulls out a cigar. He pulls out this thing of brandy, or something. Mind you, it's 9:00 in the morning. Pulls out this thing.

Amber Stitt [00:15:59]:
Where are these people with their booze and their pies?

Christopher Gandy [00:16:02]:
Brings out this thing of brandy, puts up two glasses, pours it. He goes, "Here you go." He takes a pen out of his pocket. It's a Mountblanc pen. And so he goes, "If you want to be a champion in the business world, this is what champions do." He goes, "Here, I'm giving my pen to you." And he hands me the pen.

Christopher Gandy [00:16:20]:
And I didn't know what it was. I went back to my office and I was like, "Look, he gave me this." And they were like, "Oh, my gosh! The Mountblanc Bowler Roller pen? You got that one? He gave it to you?" So I understood like, "Hey." He goes, "This is a big deal pen. Big deal people write deals with these."

Christopher Gandy [00:16:36]:
I was like, "Okay, fine." So I put the pen in my pocket. He goes, "So if we want to do business together, I don't do business with people I can't at least have a drink with." I'm like, "Okay." Who am I not to agree with this guy? He's going to do business with me. Pours it, slides it over to me. Mind you, I have never had brandy before, but the things you'll do for business, right? So I said, "Okay." He slides it to me.

Christopher Gandy [00:16:59]:
I mean, it's that high. Okay, well again, I've never had brandy. I'm like, "Oh." He's like, "Cheers." Takes the glass, puts it up, and he goes, "You can just kill it." I'm like, so it's like this much easier. "You just kill it." I kill it.

Christopher Gandy [00:17:12]:
I think my throat has exploded and I'm trying not to make a face. Oh, and it's so, so, so, so, so, so bad. Mind you, we sat there till like 3 o' clock in the afternoon as he smoked in this place. And I came out. He actually did write an application with me, but that was probably one of my more...

Amber Stitt [00:17:32]:
Not that day? You probably had to...You did case design?

Christopher Gandy [00:17:35]:
I didn't have to do any of that. He's like, "I'm doing business with you. I want to buy insurance." He goes, "I want to buy insurance and I'm going to buy it from you." He goes, "Because you know what?" He goes, "I know you..." And he said at the end, he goes, "I know you don't like brandy because I can tell by the look on your face."

Christopher Gandy [00:17:48]:
He goes, "And I know you don't smoke cigars because I can tell you were hacking the whole time I was actually having a good cigar." And he goes, "But I admire the fact that you actually met me where I was at and you were comfortable just hearing me out and spending time with me today. So I'm going to do business with you." So that was really one of the more endearing, awesome and challenging situations in my life. But, if someone's listening to this and they're like, "Wait, you did what?" But, yeah, it was fun.

Amber Stitt [00:18:17]:
Well, and that's the thing. It's like you never know. You never know who you're going to meet and how it's going to affect you. So as people finish up the episode with us today, what's the takeaway? What is something they're going to turn off the... however they're watching, and they're going to do this today, what do you want for them to take home?

Christopher Gandy [00:18:32]:
Well, I want people to...there's a couple things that I did say from the stage, and I'm glad that you're allowing me and anyone that's listening to just partake in this, is that we have to remember that we're human beings behind all this and that we have to take care of each other. If we start with that, and curiosity, and we care for each other, we can do anything. I think if we start with that, everything else is possibilities for us. And so my cry is that as an organization, we show up better. We're present for each other, we support each other, we uplift each other. That's important. And now it's time for us to activate each other. Most people have stood in the shadows, "I did my part."

Amber Stitt [00:19:18]:
Yeah.

Christopher Gandy [00:19:18]:
But now it's time for us to activate each other. And so when your number is called, and I will be calling numbers, "Hey, listen, remember, I need your help." Because one of the first things my coach shared with me was that when you ask people for help, they're willing to do it for you, if you ask them nicely. And so I've asked people, "I need your help. Can I count on you?" If they say, "Yes," then I'm counting on you. So people will do things for other people more than they'll do it for themselves. And so I want people to understand that this is the time for us to make a difference, not only for NAIFA, but for ourselves. We can prove to ourselves, our families, that we can do something collectively, together, bigger, better.

Christopher Gandy [00:19:59]:
And that as we become the catalyst of change in our lives, in other people's lives, we inspire other people to do the same.

Amber Stitt [00:20:06]:
It all matters.

Christopher Gandy [00:20:08]:
It all matters.

Amber Stitt [00:20:09]:
Thanks, Christopher. It was wonderful. Thanks for listening, everybody.

Amber Stitt [00:20:13]:
Thank you for joining us for this special edition of Pathways e3 recorded at the NAIFA e3 conference in Newport Beach, California. Join us for more insightful conversations with the experts and leaders of their industries. Until next time, keep taking action on your unique path!