Building a Lasting Legacy: Succession & Mentorship in Financial Services with Shane Westhoelter

🎙️ Welcome to a special episode of Pathways with Amber Stitt, recorded live at the NAIFA e3 conference in Newport Beach, California! 

Host Amber Stitt sits down with industry leader Shane Westhoelter for an inspiring and insightful conversation on legacy, succession planning, and the evolution of the insurance profession.

In this episode, Shane shares moving personal stories—including the transformative moment he delivered his first death claim check—and how that experience shaped his perspective on the value and dignity that insurance brings to families in their most difficult times. 

From his beginnings as a cable lineman to building a remarkable career in financial services, Shane discusses the challenges and rewards of finding purpose both inside and outside of your professional identity.

Amber and Shane dig into:

💡 The changing landscape of legacy planning and succession in today's financial services industry.

💡 Why mentorship and bringing new talent into the business are crucial for the sector’s future.

💡 Actionable advice for those getting started—and those considering transitioning out of the industry.

💡 The vital role that education, compassion, and a sense of purpose play in building a career that truly impacts lives.

💡 Plus, don’t miss Shane’s “four ifs” of life planning, his perspective on building legacy vs. wealth, and a fascinating historical anecdote about Colonel Custer and the origins of life insurance in America.

✨ Whether you’re a financial professional, business owner, or simply interested in stories of growth, impact, and legacy, this episode is packed with practical insights and heartfelt moments.

Listen, learn, and take action on your unique path!

📽️ To watch this episode: https://youtu.be/XTn-iBH-Qvw

🔗 To connect with Shane:

📲 Websites: https://gfainvestments.com & https://qualitylifeplan.com

📲 LinkedIn: https://www.linkedin.com/in/shane-westhoelter-aep-clu-lutcf-ltcp-58a9511a

#pathwayswithamberstitt #amberstitt #shanewesthoelter #naifae3 #legacyplanning #mentorship #insurancestories #financialservices #lifeinsurance #successionplanning #takeaction

📻 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

Shane Westhoelter [00:00:00]:
Through the tears, she finally said to me, she said, "Mr. Shane, thank you for this $10,000 check. May not be a lot of money to a lot of people, but to me, it allows me not to have to ask my family, my friends, or my church for the money that I need to give my son the decency he deserves. So thank you for being in the insurance business and helping me keep my dignity." And that was something that changed my life.

Amber Stitt [00:00:22]:
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. So we are live from NAIFA e3.

Amber Stitt [00:00:45]:
And we have Shane here as our first podcast guest.

Amber Stitt [00:00:48]:
Welcome, Shane.

Shane Westhoelter [00:00:49]:
Thank you. It's a pleasure.

Amber Stitt [00:00:50]:
And we grabbed you before you're on main stage twice this week, which is probably to be expected with your extensive history and leadership. And I thought for the first podcast episode, it'd be great to talk about legacy. And I think you're the guy for the job. Giving you a little context that growing up in the business, my father does a lot of succession planning for business owners and myself, now closer to 50 than 40, I have a lot of friends that have been talking about it. And I know that you help others and kind of mentor and really think about that. But I feel like times have changed a bit and I was really curious to see, is the legacy planning getting harder, or is it a little different than it ever was before?

Shane Westhoelter [00:01:33]:
That's a great question. I think over the 35 years of my career, I've seen the evolution of solo practitioners starting in the business. Back when I was brought in the business, I think the industry for the most part was you're in business for yourself, maybe not by yourself, but you're trying to build a practice that is rollable, sellable, transferable. In later years, the vision for most, I think, were to maybe bring family members in doing something for their children that they could have kind of a small business, if you will, mentality, entrepreneurial. And the industry kind of...I think it changed for a couple of reasons. Number one, I think the industry today is so broad and vast in product and knowledge.

Shane Westhoelter [00:02:11]:
It's not like you come in and you go sell a hundred of one particular thing. It's like you have to learn the smorgasbord right from the beginning because that's what consumers expect. The second part of that, I think also people are more diverse now geographically. And so it's not like you're just serving people in your geographic area, your town, or your metropolitan area. It could be multiple states, you know, over multiple states. And then I think the third part of that also is we're all living longer. And so back 30 years ago, even life expectancy was probably late 60s, maybe 70s. Now it's pushing 80.

Shane Westhoelter [00:02:45]:
I think we're moving towards it's going to be 90 to 100. So part of what I'm noticing in the legacy planning is they don't want to quit. It's like, "Why do I need to get out?" It's not a physical job. We're not hanging on telephone poles or digging ditches or farming fields anymore. So as long as they're intellectually able to keep up with the business, a lot of people don't really want to totally get out because they enjoy it. They enjoy the social aspect of the industry.

Amber Stitt [00:03:08]:
Yeah, I think that's where I was really going with it because we go to conferences, we see our friends, and we have friends that are on stage, leader conferences. And that's kind of where I was going, is the identity of us and the "atta boys, or girls" kind of that it's fun to work so hard to go, "We made it!" And we're all seeing each other for the greater good and having that collaboration. I was curious if there's like a point where you talk with people, or even think for yourself that there should be a point to really start transitioning out. Do you think it's smart for a person to find more identity outside of the business before it's too late, or are there no rules on that?

Shane Westhoelter [00:03:41]:
That's a great question. Along that line is a great question would be, "Well, if you weren't getting paid for it, what would you do with your time? What would you like to do with the hours that you're not getting paid for?" And if they don't have an outside hobby, an outside interest, like this is their career, it's what they get up and do every day. It is their identity. As you said, a lot of times it's kind of like, "If I don't come into the office, then where's my identity? Where am I going to go?" So I think part of that is finding in life something that's more meaningful. What's your legacy? Why are you doing it? What is your end planned, if you will, in the sense of just because you start to hand off the business to someone else doesn't necessarily mean you have to disappear. We've got story after story where we've helped people, where we said, "Look, why don't you let us buy a piece of your business so that you can take some money off of the table and begin to enjoy life along the way?" In order to do that, you also have to be able to give up, to go up.

Shane Westhoelter [00:04:32]:
So you have to have something in place to where you have staff, or other people, or other advisors that are in your practice that you can say, "Look, it's okay for me to take two weeks, go travel Europe and enjoy the career and the money that I have." Can you do that? And that's where I think that that crossroads hits is I see people in their 60s, even 70s, mid-70s now that are like, "I've never had a vacation for 50 years. This is what I've done. Yeah, my vacations were around conferences, or going to meetings."

Amber Stitt [00:04:58]:
Well, there's a write off there, so I suppose that could be smart. But at some point, yeah, what else is there?

Shane Westhoelter [00:05:04]:
And it's having something else in life. And part of that is, is just because you hand it off to someone else, or maybe you sell some or all of your practice, maybe you don't get out of the business, maybe you become the rainmaker, maybe you're the one that becomes known in the community that you can go still have those lunches and coffees and hang out at the country club and enjoy referring people back to the firm so that others can do it.

Amber Stitt [00:05:23]:
Yeah. All right. So going back in time, I heard that it's possible you were in a different, completely different profession before this one. How did you bridge that? How did that come about for you? Can you share what you were doing prior to industry?

Shane Westhoelter [00:05:35]:
Yeah, so I went to school, I was athletic. And of course, for those of you that know something about me, those of you that don't, you'll learn. But I was in sports, very athletic, was running, ran the mile and was qualified for the Junior Olympics and then the US Olympic team back in the late 70s, early 80s and we ended up boycotting the Olympics and I was at the university and enjoying life. Wanted to go into corporate law, fashion design before that was popular. And the downside of that was my girlfriend ended up getting pregnant and I ended up dropping out of school, second year in college to start to raise a family. And so I didn't have a lot of options. I grew up in a very rural area.

Shane Westhoelter [00:06:15]:
Those of you that have heard my talk in the past may know some of these details, but I grew up in a township of about 800 adults, a grade school, first grade through eighth grade was about 200 of us total. And so it was a very small, very rural area. And my outlook on life at that time was I was either going to end up in a factory somewhere becoming a machinist, or working on the farm. And so I didn't want to do either of those. So I really wanted to get off into college and make something to myself and that didn't turn out. So I became a cable lineman. I did that for 8 years.

Shane Westhoelter [00:06:44]:
And then my father had been in sales off and on throughout his career of various things. And I went to him one day and said, "How do I get into sales and what else could I consider?" And he said, "You might want to try the insurance business. I think you'd be really good at it." So I tried it, ended up selling $5,000, $10,000 policies door-to-door in the inner city of St. Louis, Missouri. And that's how I started in my career.

Amber Stitt [00:07:05]:
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 [00:07:24]:
Okay, so can you give me, top of mind, a story that was just like you're in someone's house, you're so nervous. Do you have any of those that were just like that one time?

Shane Westhoelter [00:07:32]:
I was nervous every day. I'm down in the inner city of people on welfare and government aid and having to sell $5,000, $10,000 life insurance policies and then going back every month to collect that premiums to make sure that they didn't lapse. And about 3 months into my career, I had to deliver my first $10,000 death claim check to a mother who had lost her 7 year-old son in a drive-by shooting.

Amber Stitt [00:07:54]:
Oh goodness.

Shane Westhoelter [00:07:56]:
We sat there, we reminisced and she told a lot of stories. Of course, through the tears, she finally said to me, she said, "Mr. Shane, thank you for this $10,000 check. May not be a lot of money to a lot of people, but to me it allows me not to have to ask my family, my friends, or my church for the money that I need to give my son the decency he deserves. So thank you for being in the insurance business and helping me keep my dignity." And that was something that changed my life. To think about a $10,000 death claim check after you had just lost a 7 year-old, and the thing that is on your mind is the dignity that you can provide for your son to give them the decency they deserve.

Shane Westhoelter [00:08:33]:
And from that point forward, I began to look at insurance totally different. We plan for the expected, we insure against the unexpected. But we're in a profession where when everybody else is asking for money, money to repair your car, money to repair your house, money for your healthcare needs, money for final expenses, we're in an industry where we're bringing people checks. We're providing them the opportunity to keep their dignity when it matters most.

Amber Stitt [00:08:56]:
Thank you for sharing that, taking that further. As a younger person, we talked about legacy on one side of things, but we also need to pull in new talent. To keep this going is so important. What would you share with a younger person, someone new to NAIFA perhaps, that they're not so sure about getting into the business?

Shane Westhoelter [00:09:12]:
Yeah, I think absolutely getting into the business is not as easy as it used to be. Of course, it was never really easy.

Amber Stitt [00:09:18]:
But it was harder to go into the door-to-door.

Shane Westhoelter [00:09:20]:
Absolutely, yeah. Or sitting out at fairs collecting names and then calling them afterwards and so on. I think today, if you take a different approach, think about it as a profession, because it is a profession. It's just as important as being an attorney, a doctor, an accountant. I mean, those are all professions that are right in line with what we do. And that's providing people a service that they don't necessarily enjoy paying for. But I've never had anybody hand me a check back and said, "Hey, this is too much life insurance. Why don't you take half this check back?" They value it when it matters most.

Shane Westhoelter [00:09:51]:
We have to take pride in that, that we're there to help them discover that need and understand that need. So I look at it more as an education, more than selling of a product. And if you ask people, "What do you want to do when you retire or when you no longer need to work because you've acquired enough wealth that you don't have to work anymore, what would you do?" Or, "What would you do in the event your home burned down in a California fire, or a hurricane on the east coast? What would you do? Are you in a position that money is no longer a necessity? Like you're not afraid?" And I've said, money doesn't necessarily bring us happiness, but it sure does solve a lot of problems.

Amber Stitt [00:10:27]:
Okay, so trick question for you. If you had to pick between building wealth, or building a legacy, what are you going to pick?

Shane Westhoelter [00:10:33]:
Building a legacy.

Shane Westhoelter [00:10:35]:
Yeah, that's not a trick question. Not for me.

Shane Westhoelter [00:10:38]:
Building a legacy. Because, I look at it this way, we have 4 questions that I typically will ask a client when I'm sitting with them, and that is, I'm in the business of taking the "if" out of life. There's 4 "ifs" that you need to address and think about regardless of your age. Number 1 is, "What if you live?" Do you have the wealth that you need to live the life you want to live the way you want to live it without financial stress? "What if you linger, become sick, hurt, or disabled?" How are you going to pay for that? Are you going to be able to get the care that you want, the care that you deserve, the care that you desire in order to keep your dignity? "What if you leave through death, or divorce?" Will the assets transfer the way you want them to transfer, to whom you want them to transfer? And the last question is, to your point, "What's your legacy?" We're all going to leave one by default, or by design. I propose that we should do it by design. The legacy is how we're known. The legacy is what we can leave.

Shane Westhoelter [00:11:24]:
There's two things that I probably will never see, and that is a U-Haul behind the Hearse at a funeral with all the possessions of the person in the hearse, or a banker coming up to the coffin and putting all the money of the person in the coffin for them to take with them. So I have a phrase that I've said for many years now, I said, "Everything that we acquire on this planet, whether it be wealth or possessions, we're not taken with us. So you might as well learn to enjoy them while you're here."

Amber Stitt [00:11:46]:
I like that. Okay, so some of the listeners to the podcast are with us, and some are listening after the fact. So if we're going to wrap up today, is there anything you want to share that's just like an absolute action item? And maybe we could talk to two people, maybe the person coming into the business and then the person maybe leaving the business. Are there any actionable items that you want them to think about from this episode?

Shane Westhoelter [00:12:08]:
Yeah, I think the person coming into the business, look at it with pride, be excited about coming to this business because it's a profession that is absolutely needed. It's one that probably has not gotten the respect, if you will, that other professions have gotten through universities and that is changing, which is a good thing. But again, we're in a profession that we can change people's lives with a stroke of an ink pen. We can bring them money on 10 cents on the dollar. Give me a dime, I'll give you a dollar when it matters most. I mean, there's so many things that we can do to impactfully change people's lives. And as you grow in the profession and you start to acquire a little bit more and more success, think about the philanthropy, the charity, the give back that you can do, and to the community that you live. And for those that are leaving the business, I would say have a plan.

Shane Westhoelter [00:12:53]:
Make sure that your business is set up to where there's operating systems in place, there's people around you that you trust and learn to give up, so that you can go up and then start to enjoy life and then reach down and pull someone else up in this industry. You mentioned this earlier in this broadcast that there's not enough young people coming into the business. And I think part of that is, is because those that have been in the business a long time have stopped reaching down and pulling someone else up and helping be a mentor and to train others. And we need to get back to that. And I'm speaking to my peers and people like myself that have been in the business for 30 plus years to say, "What is our give back? Where can we reach down and pull someone else up in the industry?"

Amber Stitt [00:13:29]:
It's interesting because we can come to conferences, but I was going to say to Jason, the e4, the 4th element could be "execution". So how do we keep the mentorship going? It's really reciprocal.

Shane Westhoelter [00:13:40]:
Yeah, the mentorship is key and it's a unique industry. But if we bring back that pride, we bring back that excitement and we start bringing young people to conferences to hear what we do and how we change lives and "Life Happens", a great program that's available for the general public out there and those in the industry should know it. The stories that we hear through that are tear jerking, they're heart wrenching. And that is what we do. And it's been that way for hundreds of years. One last thing I'll share with you, I heard recently, I'm dating myself, but Paul Harvey was a guy that I grew up with. My dad made me listen to it all the time.

Shane Westhoelter [00:14:12]:
And he's a guy that always says, "And now the rest of the story." And I'll keep this short, but he shared a story where he said there was this general that after they came back from the Civil War, packed in his backpack & his saddlebag, rode his horse fort-to-fort, with enough food to get him from one fort to the next and a bunch of life insurance policies in his backpack. And when he got there, he insisted that every general and every soldier write a life insurance policy on themselves. And of course, he got a lot of resistance. He finally found one particular general that said, "Yes, I believe I should do that, even though I don't have any children, I don't have any family, I do understand the importance of leaving some money behind to create a legacy." And he insisted that every one of the soldiers that served under him also take out a life insurance policy.

Amber Stitt [00:14:55]:
Wow.

Shane Westhoelter [00:14:55]:
The rest of the story is that was Colonel Custer who wrote that life policy and insisted that all his entire troops write life policies. And that became iconic in our history.

Amber Stitt [00:15:05]:
That's really neat. I never heard that. Thank you for sharing that. Thanks for being live at e3 with us. Really appreciate it, Shane.

Shane Westhoelter [00:15:11]:
Absolutely. Thank you for having me.

Amber Stitt [00:15:13]:
Perfect.

Amber Stitt [00:15:14]:
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!