Episode TL;DR
Climbing a serious mountain and building a serious financial plan have more in common than most people think. In this episode, Dan Pascone and fellow financial planner and mountaineer Chip Pyfer unpack what it really takes to tackle high-risk goals: preparation, discipline, clear “why,” and smart risk management.
Chip shares stories from Denali and Mount Everest (including why turning back saved his life), how childhood money experiences create fear and “money scripts,” and how thoughtful, fiduciary planning helps clients move from fear toward the life they actually want.
Key Takeaways
- Your “why” matters more than the summit. In both mountaineering and money, the goal isn’t just hitting a number it’s designing and living meaningful experiences with the people you love.
- Fiduciary advice is about alignment, not products. Chip explains the fiduciary standard as legally and culturally putting client interests first, with advice-driven planning and minimized conflicts.
- Fear around money is often rooted in childhood. Early experiences like divorce or financial insecurity can hard-wire money fears and scripts that drive adult decisions unless they’re examined and rewired.
- Partnering with experts reduces risk. Just as climbers hire professional guides and Sherpas to navigate dangerous terrain, investors can use a trusted advisor as a “thought partner” to manage complexity and avoid costly mistakes.
- Sometimes the bravest move is turning back. Chip’s decision to abandon an Everest summit bid due to high-altitude pulmonary edema shows the power of making difficult, rational choices under pressure a useful analogy for markets and life.
- Deep discovery questions reveal the real plan. Using George Kinder inspired questions about time, money, and regret helps clients surface their true priorities so the financial plan supports what matters most.
Key Moments
- 00:00 – Intro & episode setup. Dan introduces episode 48 with guest Chip Pyfer of Wealthspire Advisors and previews the link between mountaineering, fear, and financial planning.
- 01:40 – Chip’s path into financial planning. From a family doctor household with low financial literacy, to law school, boutique investment banking, PwC, and eventually the RIA world.
- 04:08 – What does “fiduciary” really mean? Chip explains the fiduciary standard in simple terms: fee-based, advice-driven, and legally obligated to put client interests first.
- 05:24 – How Chip found mountaineering. Growing up in Oregon, early climbs in the Cascades, and catching the bug after a guided ascent of Mount Rainier with his now-wife.
- 06:58 – Turning 40 and seeking bigger mountains. A group of friends decide to celebrate 40 with Mount Whitney, then build an annual tradition that leads to Shasta, the Grand Teton, and ultimately Denali.
- 07:44 – Denali as a catalyst. A successful multi-week climb on North America’s highest peak unlocks Chip’s confidence to pursue serious international mountaineering.
- 08:07 – What it takes to climb big mountains. Physical preparation, patience, teamwork, and years of practice before considering a peak like Everest.
- 10:59 – Bringing the “why” into planning. Chip describes moving from ego-driven peaks to a deeper why: shared experiences, testing limits, and learning through suffering.
- 12:49 – Discovery & Kinder’s three questions. How Chip and his colleagues use past, present, future conversations and George Kinder style questions to surface client values and regrets.
- 18:09 – Fear, money scripts, and childhood trauma. Chip shares how his parents’ divorce, financial insecurity, and law school debt shaped his own fear around money.
- 20:12 – The Khumbu Icefall and real fear on Everest. A vivid description of the most dangerous section of the climb and what it means to move through terror with competent guides.
- 22:25 – Advisors as thought partners (and Sherpas). Why high-aptitude clients still want a professional partner to navigate complexity mirroring climbers’ relationships with guides and Sherpas.
- 24:00 – The Everest decision: turning back at Camp Four. Chip recounts developing high-altitude pulmonary edema, facing the reality of the “death zone,” and deciding not to summit to save his life.
- 26:21 – Lightning round: lasagna, Garmin, Yoda, and fasting. Chip shares his favorite meal, go-to tech, a favorite quote, intermittent fasting routine, and advice to his younger self.
- 29:11 – Bucket lists & closing thoughts. Denali as a big bucket-list item, why parenting is an ongoing journey, and where listeners can connect with Chip.
Episode Summary
In this episode of the Making Sense of Your Money podcast, Dan Pascone sits down with fellow financial planner and mountaineer, Chip Pyfer, Partner and Financial Advisor at Wealthspire Advisors. Chip shares his unconventional path into financial planning growing up in a low-financial-literacy household, pursuing law school, discovering he didn’t want to practice law, and ultimately finding his professional home in fiduciary, advice-driven RIA firms.
The conversation quickly shifts from resumes to mountains. Chip tells the story of how he fell in love with the outdoors in Oregon’s Cascades, then rediscovered mountaineering in adulthood. A guided climb of Mount Rainier with his now-wife led to a 40th-birthday pact with friends: tackle a serious mountain together every year. That “big 4-0” idea evolved into a multi-year journey through peaks like Mount Whitney, Shasta, the Grand Teton, and eventually Denali in Alaska a three-week climb that proved to him he could handle serious international mountaineering.
From there, Dan and Chip explore the deep parallels between climbing and financial planning. Chip breaks down what big mountains really demand: physical conditioning, patience, teamwork, and a long runway of smaller climbs before attempting something like Everest. He talks about how his own “why” evolved from summit-chasing and ego to sharing meaningful experiences with loved ones, testing limits, and understanding the productive side of suffering.
On the planning side, Chip explains what it means to truly operate as a fiduciary: fee-based, advice-first, and legally bound to put clients’ interests ahead of the firm’s. He describes the discovery process he uses with new clients, focusing less on account balances and more on past money experiences, shared values, and future hopes. Drawing inspiration from George Kinder’s work, he walks through the three questions he often asks clients about unlimited resources, having only five years to live, and having just one day left and how those questions unlock clarity about their deepest priorities and regrets.
The discussion then gets personal as Chip opens up about fear and money scripts. He shares how his parents’ divorce and the financial strain that followed left him with a deep sense of insecurity, which was compounded by heavy law school debt. That fear became a “money script” wired into his brain, and he’s spent years consciously rewiring it both for himself and for the clients he serves. Dan and Chip connect this emotional work to the way people often approach markets and planning from a place of fear rather than purpose.
In one of the most gripping parts of the episode, Chip describes climbing Mount Everest and confronting the infamous Khumbu Icefall, a moving, creaking maze of massive ice blocks between base camp and Camp One. He explains why that section is considered the most dangerous part of the climb and why climbers must pass through it multiple times for acclimatization. He then shares the pivotal moment higher on the mountain, at Camp Four in the “death zone,” when he realized he had developed high-altitude pulmonary edema (HAPE). Despite weeks of effort and the lure of the summit, he chose to turn back to save his life.
Chip is clear: he did not summit Everest, but the decision to descend not to push on is one of the most important decisions he’s ever made. The story becomes a powerful analogy for financial and life decisions: sometimes the bravest move is stepping away from a goal when the risk is no longer worth the potential reward.
Throughout the episode, Dan and Chip return to a recurring theme: experts as partners. Just as Chip always climbs with professional guides and Sherpas to mitigate risk and increase the odds of coming home safely, many of his clients partner with him even though they’re capable of handling money on their own. They don’t just want a portfolio; they want a thought partner to help navigate complexity, reframe fear, and ensure their financial plan actually supports their life.
They close with a quick lightning round Chip’s love for lasagna and Cabernet, his must-have Garmin watch, a favorite Yoda quote, his intermittent fasting routine, and advice to his younger self to “not sweat the small stuff.” The episode is a blend of adventure storytelling, behavioral finance, and life planning, offering a memorable reminder that the goal isn’t just reaching the summit it’s living the journey well.
Full Episode Transcript
DAN PASCONE (00:00): I’m Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast, Real Conversations to Help High Earners Make Sharper Decisions So Their Money Works as Hard as They Do. This is episode number 48, and today I’m joined by Chip Pyfer, Partner and Financial Advisor at Wealthspire Advisors, to unpack what it really takes to climb a serious mountain the preparation, the discipline, and managing fear and how those same skills apply to financial planning and wealth management so you can pursue the life that you actually want. Before we dive in, make sure that you’re subscribed on your favorite platform. And if you enjoy the episode and the podcast, I’d really appreciate if you leave a quick review. Thanks so much, and enjoy.
DAN (01:12): Chip, thanks for joining the Making Sense of Your Money podcast. Really excited to have you today. I think this is gonna be a fun discussion.
CHIP PYFER (01:18): Me too, I’m delighted to be here.
DAN (01:20): Very cool. We’ve got a lot to unpack with you. There’s a lot of stuff I want to talk about related to your history, some of your personal and professional accomplishments, and how you kind of interweave the two in your business. But do me a favor, like we always do, just give our audience a quick high-level overview of who you are, your background, and what you do today.
CHIP (01:40): All right, okay, so I’m Chip Pyfer. I live in the San Francisco Bay area in Marin County. Our office, main office, is in San Rafael, California, and I have an office in San Francisco. I’m a financial planner like you, Dan. I have a great, great group of colleagues that I work with. I have just a tremendous amount of passion for living life, and I’ll share more about that as we go through this, and I share that journey with my wife, who has some similar experiences that are fun to share with you. But at the end of the day, professionally, I’m a financial planner helping people live their best lives.
DAN (02:08): I love that, I love that. You and I share a lot in common with respect to this business and how we look at it and what we’re looking to help our clients do. So I’m excited to unpack that. All right, so first off, before we get into some of the personal stuff, which I think is really, really fun, tell the audience, how’d you get into financial planning? What did your career track look like? And what ultimately made this feel attractive to you?
CHIP (02:32): Yeah, I came into it not directly. I grew up in a home where my dad was a family doctor. We had no level of financial literacy in our home as a child. I was not mentored by my father in that context, but he was my hero. And so I thought I chose a path through law school and finished up law school in 1998. In that journey, I discovered I don’t want to practice law. This isn’t for me.
CHIP: But I didn’t know where my destination was headed. So I took a leap of faith and moved to San Francisco. I was up in Oregon for school, for growing up and graduate school, and landed at a boutique investment bank called Hambrecht & Quist, which was subsequently acquired by J.P. Morgan. I learned quickly that transactional culture wasn’t for me, and I discovered what it means to be a fiduciary early on.
CHIP: I found some good mentorship. My next career stop was at PricewaterhouseCoopers, where we had a registered investment advisor business inside that business. And then I met one of my mentors in 2008, Greg Friedman, who’s pretty well known in the RIA community. And I joined his firm. At the time, it was called Friedman & Associates, and we built that firm from something in the order of $250 million up to $3 billion in assets.
CHIP: It’s a long-winded way of saying I didn’t know what my destination looked like early on. Through good virtue of finding good people to mentor me, I discovered this career that I’m in now and really leaned into it earnestly. Probably we’re at about 20, 22 years now.
DAN (03:57): All right, so before we even go deeper, you mentioned sort of a buzzword in our industry, which is fiduciary. I want you to explain, because I’m not sure we’ve actually ever unpacked this on the podcast, I want you to explain to the audience what it means to be a fiduciary and kind of how you think about those responsibilities relative to the work you do with your clients.
CHIP (04:08): Yeah, it’s pretty I think of it pretty simplistically. It’s behaving in a manner that puts the client’s interest first and foremost. We’re a fee-based business. I suspect yours is similar. We have no conflicts of interest. It is advice-driven, financial planning driven, and we’re held to a legal standard, this fiduciary standard that is literally, quote-unquote, putting the client’s interest first.
CHIP (04:36): And it becomes a cultural fabric at Wealthspire, that I always shared at Pricewaterhouse, at joining Greg Friedman’s team, and today with Wealthspire. Fiduciary working for our clients’ best interests.
DAN (04:53): Very cool, very cool, yeah, so important and sometimes I think it gets a little bit of a misnomer or maybe it’s thrown out a little bit too liberally. All right, so let’s talk a little bit about you. You are one of the few financial planners I know I think you’re the only one I know, frankly that has climbed Mount Everest. So let’s talk a little bit about that. I know that that’s a passion of yours. So I wanna talk a little bit about the work that you’ve done on the mountain and maybe how that correlates to the work that you do in the office.
CHIP (05:20): Great. Okay, where do you want me to start?
DAN (05:22): How’d you get into it? How’d you get into this passion for mountaineering? And then I definitely want to talk a little bit about climbing Mount Everest and hear what that experience was like.
CHIP (05:24): Okay. Yeah, the origin story is I grew up in Oregon skiing in the Cascades and recklessly climbing a lot of the Cascade Mountains the lower elevation mountains like Mount Bachelor, the Three Sisters, Jefferson. These are well known amongst the Northwestern people. And I did it as a young person with friends. We skied a ton. I’m very comfortable in snow since the age of five or four. And I just had that in my blood.
CHIP: And it was the first serious mountain climb I did was 1997, so I’m dating myself a bit here with my then, at the time, my girlfriend, who’s my wife now. We did Mount Rainier. We hired a mountaineering company and that was where I had my first experience of actually professional mountaineering as opposed to really reckless, like, recreational without following any rules. And I caught the bug. I caught the bug.
CHIP (06:03): And then the jump gonna make a really quick jump here that was a long time ago. When I approached age 40, I still dabbled in some mountaineering, but I, along with a group of friends who were also approaching the 40th birthday, said, let’s do something big together that takes us away from our families, our little kids at that time, our jobs. Let’s go do a mountain, get away for four or five days. And we first picked Whitney, Mount Whitney in Southern California, which happens to be those who don’t know is the highest peak in the lower 48 states. It’s just over 14,000 feet. And we didn’t know what we were doing really. We hired a good mountaineering organization and just had a blast.
CHIP (06:58): And to this day, those best buddies that I climbed with at the age of 40 and I’m 56 now we continue to pick a mountain every year to go climb.
CHIP: And we’ve been on this journey where we did Whitney, Rainier again (for me Rainier a couple of times), Shasta, the Grand Teton in Wyoming. Then we stepped a little further out of our comfort zone. And the big one that a lot of listeners might be familiar with is Denali in Alaska. And that was the first step into international or outside the lower 48 states big mountains. That’s the highest mountain in North America. It’s one of the Seven Summits.
CHIP (07:32): And I can describe what that is in a minute. And we had such a successful and positive and beautiful experience climbing that mountain together. And that’s where international mountaineering I really caught the bug. And that was in 2018.
DAN (07:44): Very cool, very cool. All right, so for someone like me who’s never climbed a mountain like that, I’ve done some pretty intense stuff from a physical perspective ran a marathon, done a bunch of other stuff. What does it take to climb one of these mountains? What is the experience like? How do you prepare for it? What’s it like when you’re up there? Dive into that a little bit more and help us understand the experience.
CHIP (08:07): Yeah, I think I’d break that down into both the two sides. One is the psychological, emotional, practical, and one is the physical. I too have done several marathons.
CHIP: My wife and I share a passion for being in the outdoors and doing some pretty, by most standards, extreme outdoor endeavors. And so there’s a level of physical fitness that is required. You can’t walk into these mountains without being fit. I have once and it doesn’t pay off it doesn’t work out if you’re not fit. On the psychological side, it’s just having patience. You know, patience is a really important attribute for mountaineering.
CHIP: You have to be very oriented into team, working as a team. The sport’s very dangerous and you really rely on your partners. And practice.
CHIP: You know, we’re going to talk about Everest a little bit here today, but that didn’t happen until 15 years or 20 years of other mountains that got me to a spot where I felt I had the competency, the experience, basically the credentials to go for that big of a mountain.
DAN (09:06): So was that like was Everest, has that been for a long time for you sort of like a bucket list item that you wanted to check off and you were sort of preparing by doing all of these others along the way? Or what ultimately prompted like if this is your passion, we got the Super Bowl coming up this week, and Everest seems like the Super Bowl of mountain climbing. Was it just a natural thing, “I want to go do Everest,” or what prompted you to get there? I’m sure it was with a similar group. Tell me a little bit about that.
CHIP (09:26): Yeah. The vulnerable, meaningful, real answer is it was not a bucket list item for me. For most of my life, I saw it so far away and like unimaginable. It didn’t really come to my bucket list until 2018. And that was the year we climbed Denali.
CHIP: And Denali is a 20,000-foot it’s a massive mountain. It takes anywhere from two to three weeks to climb. It’s serious business.
CHIP (09:53): And we did all the things you do to prepare for that type of mountain. I climbed it with four very good friends and we just had a wonderful experience. And it just sort of like it opened a door to other, “Hey, we can do this.” And it built a lot of confidence, personal confidence. There’s a lot more that we can unpack here, as you say, around what it takes then to do an international mountain around time, money, preparation, support from the family. But that was a catalytic moment in 2018 for me to look beyond kind of the usual 14ers in the lower 48 United States.
DAN (10:36): Okay, very cool. So you mentioned I thought it was really interesting when you were talking about what it takes to do one of these climbs, right? Both from the physical and then sort of like the mental, psychological perspective. And I would imagine a lot of the stuff that makes that feasible and makes you prepared for that, you probably apply in your business and with clients. So talk a little bit about maybe the way that those are sort of interwoven into your business and your life.
CHIP (10:59): 100%.
CHIP: Yeah, so in mountaineering, those people who do it and those people who do it professionally, they often speak early on in their, you know, their pursuit of climbing as understanding your why. What is your why? What compels me like I would do Rainier or Mount Hood? And early on, years and years ago, I didn’t if somebody asked me that question, I’d probably just say, “I just want to get to the top and maybe ski down.” Or it was more ego-driven.
CHIP (11:28): As I matured and experienced more dangerous situations and as I evolved as a person, I discovered that my why was way more than that way more than just because it’s there or to get to the summit. It was about my why, if you’re getting at that if I can get at that is sharing experiences with people I love, doing something that tests their and my limits, and in the process, learning from suffering.
CHIP: Learning there’s a positive side of suffering. Suffering is very hard. You ran a marathon. You probably bonked at some point or hit the wall. All that’s a suffering moment. Everyone goes through it in extreme sports like that. And there is a degree of suffering that is hard to explain in high elevation mountaineering. And actually I’d like to tell you a little story, a few stories from Everest a little bit later about the degree of suffering that I went through to survive. But for me, the why comes down to sharing experiences with people I love.
DAN (12:30): Okay, I love that as your why and you’re crystal clear about that. How do you help clients in the financial planning and the wealth management process to figure out their why and then use all the services that you and your firm provide to help them live that why?
CHIP (12:49): Right, and there really are some very tangible comparisons here. I’m fortunate to be in a culture amongst very talented people that are committed to this financial planning process. And when we partner with let’s take an example of a new client. A practice that’s somewhat common, and I suspect, Dan, that you do this too, is at the very beginning, you have a conversation that’s less about money and more about the family’s goals. And we loosely call that discovery. And that discovery conversation explores this new client, their past, their present, and their future.
CHIP: And learning their experiences with money, people that mentored them with money, people that mentored them in life, how if they happen to be a married couple how they met.
CHIP: Why are they drawn together? What are their shared values? If they have children, what are the values that they want to pass on to them? And then you can go further and further around legacy planning and you learn about what’s most important to them. And that really gets ultimately to their why.
CHIP (13:55): And when I get into the subject about why I really like to acknowledge that there is somebody who is influential to me who doesn’t know me. His name is George Kinder. You probably know who George Kinder is. Very thoughtful financial planning and life planning leader in the 90s and 2000s. And he had the book Seven Stages of Financial Maturity, I think. And there’s a script in there that I’m going to boil it down for like a little soundbite here. But there’s three questions that we ask I ask, my colleagues ask new clients early.
CHIP (14:14): And they’re this simple. And they’re usually caught a little off guard. And we ask for permission because we’re going to go a little deep here with the client. We say, “If you had all the money in the world and all the time, what would you do?” And it’s really amazing they start to daydream about what they would do. And maybe they’re philanthropic or they’d buy a fancy jet or whatever. You learn a little bit about what their values are. What they don’t know is the next question, which is, “OK, with your current resources, financial and otherwise, but you have five years to live, what would you change?” And then just let them talk. And you really open up, give them space to share. If they happen to be spouses, they’re gonna look at each other and they’re gonna it really gets them going. And the next question, the third and final question, which they’re really typically not prepared for is, “All right, you have one day to live. What regrets do you have, if any?”
DAN (15:05): Yeah.
CHIP (14:58): And in our conference rooms and you see this, Dan, in your career there’s several tissue boxes. It’s usually when people start to really open up. Their heart opens up. You’ve earned a bit of trust with them. They become more vulnerable. And you hear what’s most meaningful for them. And that’s where we get into this why. What is the purpose of money, ultimately?
CHIP (15:19): I hope we can partner with our clients we aspire to partner with them to help them harness the resources they have and their skills to go out without fear. I’d love to talk about fear and how it relates to climbing mountains and money. Without fear, with clear visibility, to go live their best life. And so that you asked me about the comparison of the why. There’s a very close correlation to that question, “why.”
DAN (15:37): Yeah, I love that.
DAN: I do want to get to the fear point. I’m gonna get to that next. One other question that I want to unpack here, Chip. So those are very, very good questions and deep questions and you’re going a lot deeper than just, you know, what do you have in your portfolio? What’s your tax situation? Yada, yada, yada, right? What do you find how often are you finding that people know and are quick to answer those? Does it take a lot of thinking? Do you have to dive a level deeper? Because I imagine a bunch of those questions, folks probably haven’t ever been asked before. So how do you sort of make sure that you get them comfortable, opening up, and if they’re a little bit caught off guard, how do you make sure that you get them prepared to share the most relevant information that helps you and your team with your ultimate process?
CHIP (16:29): Let’s first acknowledge that table stakes are the competency around financial planning. I’m going to speak on behalf of my colleagues. We’re all the majority of us have certified financial planning credentials or advanced degrees and different types of credentials. So there’s a level of high competency with the technical planning.
CHIP: We’re talking this next level in this context. The way we don’t freak them out is that and you do this in your business if you meet a new person, you’re probably not leading with that. You’re probably not going to punch them in the face. We’re going to like, we’re going to go right at your heartstrings, because that can be a little unsettling. But you do explain to them how we operate and how we partner. “We want to we’re going to next meeting, when we get to that discovery, we’re going to start to peel that onion back.” And ultimately, it won’t surprise anybody. We ask for permission.
CHIP (17:10): You know, and you can imagine we’re in the West Coast, maybe it’s a Marin County thing but people are really willing to, they really have an appetite for connection. And they probably haven’t when they find us here, they probably found us because they’re not getting it. Right? They’re not they have an appetite for it or a need. They may not know it, but once, if we have a good connection, it’s incredibly valuable for them.
DAN (17:33): Very cool, very cool. That’s great stuff. All right, so this concept of fear. This is so, so pertinent in, I imagine, what you love to do outside of work. I imagine there’s gotta be a level of fear if you’re climbing Mount Everest, right? But fear, as we both know, has such an impact on how people manage and make decisions around their money.
DAN (17:57): I want you to talk a little bit about your experience in both, how they may be related or unrelated at times, and the impact that you’ve seen fear have in your personal life, and then with the work that you’ve done with your clients.
CHIP (18:09): Yeah, fear is a real thing. So I’ll just be open here and share with you that I grew up middle class in Eugene, Oregon. My dad was a family doctor, which is not the highly compensated doctor kind of career. And at age 10, I felt like everything was perfect. And then my parents got a divorce. And I went on my journey, and a bit of trauma in that experience, which is not unique. In this country, we have a high degree of parents getting divorced. My trauma was financial insecurity.
CHIP: At about age 10, 11, 12 because of the division of assets and the stress of the cause. And my mother was a stay-at-home mom. So it just it was an environment where I was acutely aware of, “We are a little there’s a little insecurity here financially.” And I carried that burden because I didn’t have proper tools to understand it for years. And then, Dan, I doubled down when I went into law school and took a load of debt out because I was pursuing my why and came out of law school with this giant monkey on my back of debt. So I’ve had years of this financial fear of failure and all that that has.
CHIP (19:29): Wired it’s neurological. It’s wired in my brain. I’ve been on a mission, both personally and partnering with clients, to help myself and help people that I partner with to rewire the brain.
CHIP: To rewire conventional thinking, these money scripts that we have that are a product of our childhood. You have them, I have them, everybody I work with has them, we all have them. And ego can get in the way of acknowledging that, but if you permit yourself, give yourself permission and the grace to actually explore, “Why do I have that fear?” So that’s on the money side, inside of your question. On the climbing side, I’m not
CHIP (19:48): someone who doesn’t lack fear. But I’ve been fortunate enough to go through a number of experiences with competent people, with competent leaders. These are people that are professional climbing guides, and practice and practice and practice, that I actually don’t have a lot of fear. I’ll give you an example that’s extreme. And I might be jumping ahead here, so tell me to pause. But on Everest, once you get to base camp,
DAN (19:57): Sure.
CHIP (20:12): the most what’s known as the most dangerous part of the climb isn’t the summit. It’s the section between base camp and Camp One. It’s called the Khumbu Icefall. And it’s a flowing glacier that moves a certain number of feet a day. And there are massive ice blocks that are 40 to 100 feet tall. They’re cracking and moving. And you have to navigate over the course of about six to eight hours to get through that to Camp One. That is the most intense climbing experience I’ve personally experienced. And on the Everest climb, you have to do it more than once.
CHIP: Because you have to acclimatize and you get your body used to the high elevations. And so you don’t just do it once. You do it at least twice, often three times going up, and then you have to go down. So you have to go through it. So up to six or six to eight times.
CHIP (20:35): That is an intense experience where, I will be honest, everyone’s a little bit spooked by that one. It’s a pretty thrilling, exhilarating, and terrifying experience.
DAN (21:10): You know, that’s really, really cool actually just to hear about that and have you share that. And I’m struck by what you said around, you know, what you gained from taking on these moments of fear, taking on these fear-inducing experiences, but doing it with highly trained, highly competent professionals. Because I think there’s a lot of analogies here that apply to business and life, frankly, that can really help you to become just a better individual, a stronger individual if you take on these types of experiences, but you can mitigate it to some degree with these professionals. And frankly, now as I’m talking, I’m hearing all these analogies in our business, right? So talk a little bit about that, because I thought that was really interesting how you framed that.
CHIP (21:55): Absolutely.
CHIP (21:59): Yeah, so this is pretty easy for me. My best I have great clients. I work with some really tremendous people, and most of them can do what we do probably on their own because they have a high aptitude, high skill level. But they want to live their best lives and they don’t want to do what we do. So they don’t see me as just the person that gives them advice. They see me as a thought partner. Someone to partner with to navigate the complexities of the financial world.
CHIP (22:25): As a partner. Right. Similarly, in mountain climbing, I have a lot of experience. I have a pretty high degree of competency and confidence. But what I’ve learned is that to mitigate risk, I always hire or partner with the climbing guide, the true professional. And there’s another layer here about Sherpas on Mount Everest that the Sherpa doesn’t get the appropriate recognition but the Sherpas are, they make it possible to climb Mount Everest. And if you’re interested, I can share more about that. But partnering with someone who is an expert in the field is going to increase the likelihood that I’m going to come back alive, for one, summit, and number two, come back healthy.
DAN (23:04): So do you envision you mentioned the Sherpa, which is clearly such a critical role. Do you envision yourself and see yourself as sort of like the financial Sherpa to your clients? Is that a fair analogy?
CHIP (23:15): It’s a fair analogy. I don’t want to be disrespectful to the Sherpa community because it’s such an incredible bunch of humans. But yes, you could draw an analogy there. The Sherpas are like, on the mountain, very critical to progress. I mean, I can go on and on with this analogy, but just checking gear, making sure that the lines are safe, the rope lines. It is a good analogy. I hadn’t actually processed it entirely, but yeah, the analogy is good with Sherpas or the guides.
DAN (23:43): Yeah, sure, got it, got it. Okay, very cool. All right, that was great. There was a lot of really good insights there, and frankly, I think some of these themes will come back up, but I wanna get to know you a little bit more, even above and beyond what you’ve shared, because you’ve shared a lot about yourself already, Chip, which I appreciate. So we’re gonna do the lightning round, you ready?
CHIP (24:00): Dan, can I do one thing, one little pivot here? Just because I feel I must share this. I got to Camp Four on Everest. And I had I came down with something called high-altitude pulmonary edema. And it was progressing through the climb. And I want to be clear, because I don’t know if you heard this, Dan, but I actually didn’t summit Everest. I got through Camp Four, which is the death zone at 26,000 feet. I was with a team of 10 climbers, as well as our Sherpa and professional climbers.
CHIP (24:25): And out of the 10, three of us didn’t summit because of severe this high-altitude pulmonary edema problem. And so this is beyond today’s discussion, but I had to make a decision alone that I had to turn back for my own safety. And it might be surprising to hear, or it might be surprising to hear what I’m going to say next, which was the decision was not difficult at all.
CHIP: You know, I had spent six weeks getting up to that point. You know, life is life. We get thrown curveballs. In that moment, I had to make a decision whether I go left or right. And I have to tell you, everyone gets summit fever there. And my heart and brain wanted to go to the summit. But my body was absolutely not going to go forward. It was crushed physically and mentally. And so I turned back.
CHIP (25:03): And saved myself, and I had a Sherpa and another climbing guide and we navigated the descent under really, really awful conditions physically and got to Camp Two and I got helicoptered off the mountain and I spent a couple days in the hospital. So there’s another story behind that, but I think the lesson here is that, you know, it’s not about the summit. You might, you know, because it’s cool to climb Everest, people think, “Did you summit?” That’d be great if you summit, but it’s not about the summit. It’s the journey. And we, you know, it sounds cliche.
CHIP (25:39): It sounds cliche, but it’s the journey. And I just wanted to get that off my chest so I didn’t leave this podcast having people think, “He climbed Everest and he summited.” No, I almost did. I got to the death zone.
DAN (25:47): I appreciate the transparency there and as I heard you talking, the word that was sticking in my head was it is about the journey and I couldn’t agree more. All right, well, you’ve gone through all of that. The lightning round’s gonna be a piece of cake for you, all right? So we’re gonna have some fun here. All right, so this is how this works. Just give us the first thought that comes to your mind. Could be a one word answer, could be a long drawn out thought, all right? Let’s do it. All right, one meal for the rest of your life, what is it?
CHIP (25:54): Wow. Well, one I love really good quality lasagna paired with some excellent Cabernet wine.
DAN (26:21): I love it. And thirsty for that matter. What is one tool or piece of technology other than your phone or your computer that you can’t live without? Hardware, software, anything in between.
CHIP (26:31): I don’t know if you can see my wrist here, but a Garmin watch the brand’s Garmin. This is a Fenix 8, it’s a data watch. It gives me all kinds of body-hack data around sleeping, physical exertion. It’s a must-have for people who are fitness-oriented and especially mountain climbing. So yeah, the Garmin watch definitely have to have that.
DAN: I love it, I love it. Do you have a favorite quote or phrase about life or success?
CHIP (26:53): The one that I learned when I was about 10: “Do or do not. There is no try.”
DAN (26:58): There is no try, I like it, I like it. I’ve heard the quote but I don’t know who it is.
CHIP: Do you know who that is? It’s Yoda.
DAN: OK, there you go, Yoda. That works, that works.
CHIP (27:09): Now I got one more for you. “If I had to live this life again, I would make more mistakes.” And I’m not saying that’s me now. I think it’s just an inspirational statement like, “Go lean into life and go experiment. It’s okay to fail.”
DAN (27:21): All right, you shared a few of these along the way, but do you have a process, a system, a routine or a hack you can share with our audience, personal or professional?
CHIP (27:31): Personal, physical I’m into, and I have been for six years probably, intermittent fasting. It is a way to keep the body clean and alert, and I’ve just really embraced it, so physical.
DAN (27:36): Mm-hmm. I’m curious, what’s your process around that? Because I do a modified version of that. But tell me what’s your process around that?
CHIP (27:47): Yeah, it’s pretty simple. It’s just you have 24 hours out of the day. You don’t eat for 16 of those hours. And so for me, it’s like 10 p.m. at night till about one or two in the afternoon
CHIP: where I just don’t have anything except for no calories basically water and coffee without creams or a light amount of like low-calorie milk. And then I break the fast and I can go intense here but I break the fast with a really clean, high-protein, low-carb, low- to no-sugar vegan shake. And then I rationalize it then I can have that lasagna. You know, I can do whatever I want for dinner.
DAN (28:18): Yeah, yeah, yeah, I love it. I love it. Very cool, very cool. All right. This is a question I usually ask, and I hesitated if I wanted to ask you, but I am gonna ask you, and maybe it’s different than what you’ve already shared, or maybe it’s the same. What’s one bucket list item that you’ve already accomplished?
CHIP (28:36): Well, my kids aren’t done growing up. I haven’t said it yet, but I’m a father of three, and they’re in their late teens, early twenties. They came to mind first, but I’m not done. You know, we’re not done together. So there’s going to be more. That bucket list is not over. We’re still enjoying a great journey together. I think the Denali climb that I’ve mentioned a couple of times with some very, very good friends was an incredible life-changing experience that I’m really grateful for, and it’s big time bucket list.
DAN (29:03): Another one that you’ve referenced a few times, but I’m curious to hear your take on it. Last one: one piece of advice you could give to your younger self. What is it?
CHIP (29:11): Don’t sweat the small stuff. Yeah, I did. I think most young people do who come from a certain background and maybe have fear in their minds and hearts—try to move on and not sweat the small stuff.
DAN (29:22): I love it, good stuff man. All right, Chip, thanks so much for joining us. That was a lot of fun. I learned a lot. I’m sure our audience is gonna learn a lot from this. Really, really cool life and business experiences. Thanks for opening up and thanks for coming on today.
CHIP (29:35): I love that, and congratulations to you on your podcast. I think you’re are you a year into it or half a year?
DAN (29:39): Yeah, we’re about a year into it. This is episode number 48. So yeah, we’re about we started actually in February of last year, so I think we’re coming up on our one year anniversary. We’re doing about one a week for a while now. So yeah, thanks for joining. And my last question to you is if our listeners want to connect with you, learn about you, collaborate, potentially work with you, how do they find you, Chip?
CHIP (30:01): Pretty simply, can Google or use your large language model for “Chip Pyfer” or “Wealthspire.” And I’m here feels like all the time but I’m always present.
DAN (30:09): Thanks again, appreciate having you on. That’s it for the episode. As always, you can find our podcast along with our newsletter, our YouTube channel, and this podcast all for free at makingsenseofyourmoney.com. Prioritize your version of a rich life. Cheers.
CHIP (30:26): Cheers, thank you.
Resources & Links
- MakingSenseOfYourMoney.com – podcast, newsletter, videos
- Making Sense of Your Money – episode archive
- Wealthspire Advisors – Chip’s firm
- Tailored Wealth – planning for high-earning professionals
- Search for “George Kinder Seven Stages of Money Maturity” if you’re curious about the life-planning questions Chip references.
Frequently Asked Questions
What does it actually mean when a financial advisor is a “fiduciary”?
A fiduciary advisor is legally and ethically obligated to put your interests ahead of their own or their firm’s. In practice, that usually means fee-based, advice-first planning, minimized conflicts of interest, and recommendations that are driven by your goals and circumstances not by commissions or hidden incentives. Chip describes it as a cultural fabric: always acting in the client’s best interest.
How is climbing a big mountain similar to building a financial plan?
Both require preparation, discipline, patience, and a clear sense of why you’re doing it. You don’t just show up at Everest base camp just like you don’t wing a complex retirement. You build skills on smaller climbs (or financial decisions), train for the conditions (volatility, uncertainty), and surround yourself with experienced partners who help you navigate risk and stay focused on your true goal.
Why does Chip say the journey matters more than the summit?
Chip’s Everest experience reaching Camp Four and then turning back due to high-altitude pulmonary edema drove home that the summit isn’t worth your life. Similarly, in money and life, chasing a number for its own sake can be empty or dangerous. The real value lies in who you become and what you experience along the way, especially with the people you care about most.
What are “money scripts,” and why do they matter?
Money scripts are often unconscious beliefs about money formed in childhood through events like divorce, financial instability, or parental attitudes. They can lead to fear, scarcity thinking, overspending, or over-saving. Chip shares how his own early experiences created a sense of financial insecurity he had to consciously rewire. Identifying your scripts is a first step toward making calmer, more rational financial decisions.
How do the Kinder-style questions help with financial planning?
The three questions Chip uses about unlimited resources, having five years to live, and having one day left force you to move beyond abstract goals and think about what truly matters. The answers often surface values, relationships, experiences, and unfinished business. That gives the financial plan something real to serve, instead of being just a math exercise.
Why might someone hire a financial advisor if they’re capable of managing their own money?
Many of Chip’s clients are fully capable of DIY investing but don’t want it to dominate their time or mental bandwidth. They hire an advisor as a thought partner and “guide on the mountain” to help them manage complexity, stress-test decisions, align money with their values, and stay the course during uncertainty. It’s less about outsourcing competence and more about gaining clarity, confidence, and time.
Related Episodes & Resources
- Browse more Making Sense of Your Money episodes
- Visit MakingSenseOfYourMoney.com – free content hub for high earners
- Watch the podcast on YouTube
- Learn how Tailored Wealth approaches life-driven planning
Next Steps
If this episode sparked something for you about your fears, your “why,” or the mountains you want to climb in your own life don’t leave it as inspiration only.
- Reflect on your own three questions. Take 10–15 minutes to write out your answers to the Kinder-style questions Chip shared. Bring those answers into your next planning conversation.
- Start building your own “climbing team.” Whether that’s a financial advisor, tax pro, therapist, or coach, surround yourself with experts who help you manage risk and move toward a life you actually want to live.