106: Scott Leibfried: What Climbing Wealth Taught Me About the Retirement Red Zone

Scott Leibfried's grandfather sold the family business at 60 with more money than he'd ever seen. He was generous, he lived long, and he ran out. That story is why Scott has spent 28 years in wealth management — and it's why he wrote Climbing Wealth.

Episode Summary

In this episode, Gabe sits down with Scott Leibfried, a Midwest-based financial advisor with 28 years of experience, to explore the parallels between mountain climbing and financial planning. From the moment Scott summited Long's Peak without a guide and couldn't wait to get back down, to guiding clients through the retirement red zone, this conversation is full of practical lessons about what it takes to navigate the second half of your financial life. Listeners will walk away with a clearer picture of what a real advisory team looks like, what triggers people to finally get serious, and why the descent matters just as much as the climb.

About Scott Leibfried

Scott Leibfried is a financial advisor and wealth manager with 28 years of experience, based in the Midwest. He grew up in eastern Iowa working in his family's agricultural business and attended the University of Northern Iowa before entering the financial services industry. Over his career, Scott has built a multi-generational, multi-specialist advisory team focused on financial planning, investment management, tax strategy, and estate planning. He is the author of Climbing Wealth, which draws on his experiences summiting mountains including Mont Blanc, the Grand Teton, and Grand Paradiso to illustrate the decisions that define financial success.

What We Cover

• How Scott's grandfather selling the family business became the origin of his entire career — and what two small decisions would have changed everything
• The shift from a commission-driven industry to a planning-first model, and why it matters for clients today
• What happened on Long's Peak without a guide that convinced Scott to never climb — or advise — alone again
• The retirement red zone: the five years before and after retirement when the most consequential financial decisions get made
• Why a real advisory team is built across generations and specialties, not just people sharing a copier
• The story of a client who retired at 58 against one advisor's advice — and used those five years before his death to live fully

Connect with Scott Leibfried

• Website: www.climbingwealthbook.com
• Email: scott@climbingwealthbook.com

Transcript

Welcome And Why Scott Wrote

0:00

Welcome to the Influential Advisor Podcast. Today, we sit down with Scott Leipfried, a wealth manager with 28 years of experience serving families and business owners in the Midwest. Scott recently published a book called Climbing Wealth, which draws a direct parallel between mountain climbing. He summited Mont Blanc and the Grand Teton and the financial decisions that determine whether your retirement is a successful descent or a dangerous one. In this conversation, we'll explore the retirement red zone, what it really means to work with a true team of professionals, and why reaching your financial summit is only halfway there. Scott, welcome to the podcast. So glad to get to talk to you today. Thanks, Gabe. The first question I wanted to ask you, Scott, could you tell us about your background and what led you to where you are today? I grew up in a small town in eastern Iowa and working in my family business, serving the agricultural community mostly with tires and trailers and working on trucks and that sort of thing. And went off to college at the University of Northern Iowa. After college, I worked selling educational books door to support my college, funded my college that way. And then coming out of school, my parents' financial advisor, we got together and he mentioned that he would need some help with his business and asked me to reach out to him after I graduated from college. And that was 28 years ago. And so here I am. And from there, just built our business both mostly organically through just doing the right thing for people and helping them with their financial planning and wealth management and hiring good professionals along the way, great professionals along the way. And we've done a little bit of acquisition where helping out other financial advisors who wanted to move into retirement. So we've done some of that as well. You've recently, Scott, written a book, and there's a story that I wanted to ask you about because you talk about your grandfather. Can you tell us a little bit about him? My grandfather, Grandpa Vic, he passed away a number of years ago. He lived to, I believe, 92, if I'm not mistaken. And he's one of my heroes. And I mentioned him in the book. Nine kids, good Catholic family, and in the three, and then he ran this the business that I mentioned, the family business, until he retired. And my dad and my two uncles bought the business from Grandpa Vic. And one of my reasons for getting into this business and doing wealth management and financial planning was inspired out of the experience my grandpa had with selling his business. I believe he was around the age of 60, and he had all he had more money than he ever dreamed of having from the business sale. There was really, I would say, not the right advice that was available at the time. He's getting a lot of messages from a lot of people. And long story short, is he was overly generous earlier in his retirement, and he spent just a little bit more than what he really should have. And so they had long lives. Him and grandma lived long lives, and later on they depleted their funds. And in hindsight, all it would have taken was a couple small things early on, and it would have made all the difference in the world for Grandpa. And of course, they were fine, and the kids all have done well, and the kids did my parents and aunts and uncles, and that kind of helped out in the end there. But I knew it really Grandpa, it bothered him that he ran out of money later on. It wouldn't have taken too much of just a couple different decisions early on, and I don't think they would have been any less happy or lived lesser of a lifestyle and that would have been better later. It's interesting to think about that. That looking back to the 1980s, that time period, that there was not the same information and approach to retirement planning at that time, and that things have really evolved since that point, haven't they? They sure have. And I would say a lot of it has to do with it's how things have evolved is so much better nowadays than it used to be. Whereas by and large, back then it was a commission-based sales-driven world in this industry. And so, of course, the industry, I don't blame individuals necessarily, but the industry as a whole rewarded selling something. And then, of course, the advice was minuscule because you had to move on, or the professional back then had to move on to trying to sell something else to someone else so that they could make a living. And it's so much better, so very different nowadays. Yeah, I think that's wonderful. That's move towards where it's really to help people prepare and to be ready for those things that are going to come up in their retirements. For

Grandpa Vic And A Hard Lesson

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sure. Yeah. Scott, I wanted to ask you, because from your book, you've climbed some serious mountains. And can you tell us about those experiences and what did they teach you about financial planning? Thanks for asking. Of course, the name of the book is Climbing Wealth. There's a lot of things I've learned with my mountain climbing adventures that are a parallel to financial decision making and working with a team of professionals versus not working with a team of professionals. I do not claim to be any sort of a pro or professional mountain climber by any stretch. I started probably 15 years ago and climbing what's called 14ers out in Colorado. And what a 14er is where the summit is 14,000 feet or more. And there's probably 50 plus of these in Colorado. There's a lot of them out there, and the difficulty range goes from relatively simple to life to threatening sort of difference. And so the first, I'd say 10 or 12 of these, they were really hard, long day hikes. It was a grind, but it was a hike, a hard hike. Going up to a high altitude where it's harder to breathe when you're up there. Could you really feel it? You get up to the top and you feel that difference. Oh, for sure. Yeah, yeah. You slow down because the oxygen wasn't as prevalent. Yeah. Right. And what I talk about in the book too is reached a point where there was Long's Peak. And it I had my sight set on this 14er. It's Long's Peak. It's an Estus Park, Rocky Mountain National Park, and another 14er, but I knew going into that there was it what's called exposure. And exposure is where there's ledges and where you they're narrow. And if you fall, you're not gonna, you're gonna be pretty messed up or you're gonna die because there are thousand foot drops. Summiting Long's Peak. And what I had imagined was like this, I imagine it'd be such a great feeling of elation. What actually happened on Long's Peak was I was very uncomfortable at the peak, and I just couldn't wait to get down. And that had a lot to do with I knew I had to go down through the same treacherous exposure that I came up through. Now made it down fine and everything. And it wasn't that I was gonna stop climbing mountains. It was just it wasn't going to be smart if we were gonna go bigger and better. We were gonna hire professional guides to do that. And so since then, summited Grand Teton in Jackson, Wyoming, summited Mount Rainier through the couch route, it's called, which is ice climbing in Washington State, and then last year over in Europe summited Grand Piradiscio, which is the tallest mountain in Italy, and then the Mount Blanc, which is the tallest mountain in all of Eastern Europe, and that was 15,000, nearly 16,000 feet in altitude. And did you have guides for these? Yeah, ever since Long's Peak, we're hiring professional guides where they know the way and you're tied to a rope and they've traveled this path. The parallel, and really this is where a lot of this came for the book. I was in a hut on the side of Mont Blanc last June of 2025. And I tell the more detailed story in the book, but the parallels in the decision making of working with professionals, I believe, make all the difference on having a successful, enjoyable journey versus maybe not coming out alive type of thing. And there's a lot of those same parallels when it comes to wealth management and financial planning, maybe not coming out alive, but financially speaking. Just after that experience on Long Peak, when you were with the guides, and when you say that they had the ropes, and did you ever feel the same exposure, or did you feel more confident, more steady, more sure that everything was being taken care of? And so you could enjoy the experiences at that point. Yeah, Long's Peak we did not have the guide. The other ones since but everything after that. Yeah, it was serious stuff, right? We're hanging on the side of a face on a rope in in certain cases, like having trust. And these, everyone, they've been there highly credentialed. Reminds me of a story. The first guy, it was a gate granteed town, his name's Jake, and we met him for the first day, like gear check. And Jake, this guy can't be 18 years old. And now he was it turned out he was probably in his early 30s, late 20s. He just looked young. We learned real soon that he had summited Denali, Mount McKinley, in Alaska 13 times. Like this excursion with us was his summer vacation. And it is interesting that once you learn, and once I learn about where someone's been and learn about their credentials, that can help with the trust level. These people are solid, they know what they're doing. That's incredible. Scott, I wanted to ask you a lot of the clients that you work with, they're already successful people. What do you think is usually the moment when they realize that something in their financial life needs to change? It's typically a life event. There's some sort of a life event that triggers because a lot of people, right, our clients that we work with, they're successful financially in their own right.

Mountain Exposure And Hiring Guides

11:57

And many of them have done a fantastic job at getting themselves to the point in which they got to before they engage our team on things. Life events such as an inheritance or a job change or divorce or a marriage, or we've had a number of new clients lately that they're done a great job into their 70s and then they woke up as like the one spouse might not have really any aptitude or interest or know what's going on and what happens if there's a decline in the spouse that is handling everything. That's a life event. Yes. And sometimes we call it the retirement red zone when people are getting close to five years leading up to, and the five years immediately after retirement is what we call the retirement red zone. We can get to okay, five years from now, done a good job building things up. I got to make sure we can flip this over from the accumulation stage to the income stage and factor in inflation and everything else that we want to accomplish. So that's typically the catalyst that causes somebody to engage with professionals. I talk about this in the book too, that just like on Long's Peak, I imagined prior to me getting to that summit without a guide, I imagine how great and elated I would feel. And just like I think someone who they might imagine once they get to 2 million or 5 million or 10 million or whatever it is, whatever that number is, that mental summit that somebody has, they imagine how great will it be when I get to this particular elevation. And then they actually get there. And it's similar to when I was on Long's Peak. And if I'm not so sure how comfortable I am where there's this is consequential now. That's typically how it goes. Exposure and those ledges that can come up in your financial life too, and that you might need a guide to help you proceed safely. Yeah, and many times people it doesn't settle in or sink in until they're there. Yeah. And then that's that life event or that change and maybe attitude around I ought not go it alone from here on out. And I like that you brought up the professionals that you want to work with it. And you in the book, you draw a hard line between what a real team of professionals who look like versus ones that just share office space. And so can you describe to me, Scott, what that real team looks and why that matters for people? Great question. There's a lot of professionals in our industry and our business that will put themselves out there as being affiliated with a larger team, or and the reality of it is they may be sharing some resources, or they're sharing the copier and the reception person, but really they're an individual or an individual and another person. What we've built is a team so that it transcends generations, and so a family can work with the team across generations because we have professionals on the team that represent multiple generations. That has a lot to do with, and there's a very clear succession, and also where really the compensation structure of any business really drives behavior. And if a professional is only rewarded for serving this specific group of people, they're not going to be motivated to help anyone other than this specific group of people. So our entire team is compensated on the success of all the clients of all of the entire team. We're very motivated to crosswork, and then that way we have certain specialists that are more focused on financial planning, others more focused on tax, and others are more focused on estate planning, and others are more focused on investment. So there's nothing keeping us from bringing in these specialists into the relationships. We work hard

Life Events And The Retirement Red Zone

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to also see to it that there's multiple advisors in the relationship that represent multiple generations. That idea really gets me thinking about working across generations because I'm thinking if mom or dad passes away and the children come in, they may have no idea what's going on in that financial life. But when you say that there's a team of professionals that have all dedicated themselves to mom and dad's financial life and really truly understand it, that probably makes it a lot easier for the kids to have things sorted out and so they can adequately just grieve for their parents and not have to dig through boxes and try to sort through things. Is that right? The importance of understanding the context of the family dynamic is so important. And that's something that is, I would say, nearly impossible to get the better advice and help and execution if somebody is coming in from their own personal bias, also, or if it's research online or working with someone who really isn't engaging into the family dynamic and what the motivations are and the goals, the real goals and the attitudes around things. Scott, is there a client story that you can share with us that has really stayed with you and that captures why this work is so important and matters to you so much? There's so many stories, but one I can share, and this was from a long time ago. This might have been 20 years ago, that has stuck with me. We had a client that was actually working with us and another professional, and they went to both of us. They went to the other professional and they came to us. It was about retiring at age that where the husband was going to retire on the retirement, I believe it was at like age 58. It was a rather relatively young retirement. Our advice was based upon these assumptions, and and this can work, and we have confidence that yes, you can retire at 58, and as long as we're mindful of how we're you're doing things, yeah. Like green light, let's do this. So he retired, and he five years later got cancer and died, like very quickly. Like it was and talking to his widow, she then told me about how they had they went to somebody else. And they were like matching things up, and that somebody else said, Don't do it, don't retire. You need to continue the work. And she said how thankful she was that the advice and us holding her hand, their hand through the retirement, and how thankful they got to spend five wonderful years together before he passed away. There's a lot there to that story, but I think the biggest thing to that story is I'd say more times than not, it's people they underestimate what's possible, especially here in the Midwest. A lot of our clients are they underestimate what they can really do and what they can really accomplish. And sometimes we have to hold people in check and they're out in

What A Real Advisory Team Does

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front over their skis, so to speak, and like, hey, hold on, we need to maybe pull it back. But many times it's really doing the work and saying, yeah, green light, do that. And this is possible, and you can do this. So there's a story that like has always stuck with me of it's more than the money, it's about like the in this case, this couple living five, like having five great years before he passed that wouldn't have otherwise happened if they would have left to their own conservativeness or left to their the the advice of the other uh professional. I think that's incredible that they because of that advice that they could do it, were able to have that time together. So that's a great example. And it's just it's so the favorite stories are of opening up the eyes of the client in what is possible. And so often it's about let's think bigger here because you can think bigger. And a lot of people, because they've been in accumulation mode and saving for retirement for so long, I imagine that can be tricky without permission to switch to the other side of okay, now we're going to spend it. And you talk about in the book about reaching the summit being only halfway. So, what are a lot of people getting wrong about that transition moving into retirement, Scott? Going back to what is possible and just with my mountain climbing. I mean, if I would have stopped at Long's Peak and say, I'm done going higher, and by the way, I would have been done going higher if I chose not to engage professionals. And but then when in in mountain climbing, most of the accidents happen on the way down, not on the way up. Oh, really? Yeah. I talked about in the book, there was the story there that was a tragic story of somebody who fell to their death on the morning that we were climbing Mount Blanc and unguided. And as with the later stages of life, and I hesitate to say retirement always, it's more, I call it financial independence where work is optional. Because some people just go cold turkey one day with work, but I'd say a lot of people, it's more of a phasing stage. And so we call financial independence when work is optional. But when that change occurs and there's a time when we instead of adding assets to our bucket, we need to start withdrawing assets from our bucket to support our income needs that aren't that were formerly coming from working a job. And that's a new aspect because there's so many items. There's items with the managing of the taxation of which where we're drawing funds from a bucket and the asset class that we're using, whether it's cash or stocks or bonds or a pension, or the list goes on and on, private equity and so on and so forth, real estate. And there's a sequence that is smarter than others in taking that income, and it

The Descent Into Financial Independence

23:55

really ends up being unique to every there isn't a template necessarily. Every family, every household is just unique, and what makes more sense for one is probably a bad decision for the next. And so, Scott, how does somebody know when they've found the right team that's best for them? I think a couple things about trust. One is integrity trust. And I would say most people in our industry check the box on integrity trust. The second part of trust is competency. And how a client would be able to know or feel strongly about their working with the right team, is how that team is represented from a credentials and education perspective and from a 10-year in the industry perspective. The team we've built is we have the five to 10 year credentialed professional very well represented, the 10 to 20 year credentialed professional, very well represented, and the 20 plus year credentialed professional, very well represented. And if you're working with a team that has all these credentialed professionals that have different tenures, and those professionals are well represented in the relationship with you, the client, that's I believe where you found the right fit. I can imagine that for newer advisors, when they're in that starting period, that working with the team members just that have been there for a long time really helps to understand in a deep and meaningful

How To Reach Scott And Close

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way the different situations. And so they can respond to their clients no matter what's coming their way. Well, and it goes both ways too. The newer, younger, energetic professionals can really teach the tenured folks on some of the newest developments, whether it be in technology or strategy, that sort of thing. So it really does go both ways. Scott, for listeners that are interested in getting a copy of your book or would like to get in touch with you and your team, how should they do that? It's just the website is climbingwealthbook.com. And there my email is Scott at climbingwealthbook.com. That's a good starting point. I'm interested in to hear people's feedback and their comments and what they like and what they don't like about what we're doing here. Have a strong passion in seeing to it that families are served for multiple generations in the right way. Scott, I've enjoyed our conversation. Thanks so much for being here today. Thank you, Gabe.