The five highest global uncertainty readings since the 1980s have all occurred in the last five years. And yet the answer Wall Street keeps selling — products that promise upside without downside — is mathematically impossible and provably underperforms over time. Simone Stolzoff, author of How to Not Know, spent years studying how people, companies, and investors navigate uncertainty well. His findings are the opposite of what the financial industry is selling you right now.
What You’ll Walk Away With
- Why our tolerance for uncertainty is declining — and the specific role smartphones and real-time data have played in making investors more anxious and worse at decision-making
- The anchor framework: how certainty in some areas of your life makes it dramatically easier to hold uncertainty in others — and what that means for how you build a financial plan
- The Slack origin story — how a gaming company at the peak of its success chose to shut down and pivot into the unknown, and what that teaches about staying open to what might emerge
- Why Warren Buffett and the best venture capitalists actively seek uncertainty — and how confusion between uncertainty and danger costs most investors real money
- The kill criteria concept borrowed from mountain climbing — and how pre-committing to rules before the emotion hits is the only reliable way to prevent catastrophic decisions
- One-way doors versus two-way doors: the Jeff Bezos framework for knowing when to agonize over a decision and when to just act
- Why buffer ETFs are mathematically required to underperform broad index funds over time — and the one question that exposes every “downside protection” pitch instantly
- OG’s case for looking at your portfolio as rarely as possible — and the surprising thing that happened when he checked his mortgage balance after months away
- Why building a financial plan around your actual goals makes the daily market headlines genuinely irrelevant — not as a coping strategy, but as a logical outcome
- Kathy’s story: what a special education teacher who maxed her Roth IRA every year from 1998 to 2024 has in her account today
Why This Matters Now
Markets will always be uncertain. Headlines will always be alarming. The question isn’t how to make that stop — it’s how to build a life and a plan sturdy enough that it doesn’t matter. This episode is the clearest case we’ve made for why your financial plan is more important than your portfolio, and why the two are not the same thing.
From the Basement
Simone Stolzoff joins Joe and OG to unpack the psychology of uncertainty — including a couple who took a year apart to figure out if they wanted to stay married, a software engineer who programmed an app to make all his life decisions, and the monk who said not knowing is the most intimate thing of all. The Investment News headline about clients wanting “headline-proof portfolios” gives OG a full platform to explain why buffer ETFs are a product designed for the advisor’s book of business, not your retirement. Doug arrives with Wild Bill Hickok trivia. Kathy from the community sends a note that should be required reading for every Gen X stacker who thinks they’re behind.
Resources Mentioned
Stacking Benjamins Community — stackingbenjamins.com/basement
How to Not Know: The Value of Uncertainty in a World That Demands Answers by Simone Stolzoff — available wherever books are sold; early readers receive an invitation to an exclusive event with Michael Lewis
Simone Stolzoff — simonestolzoff.com
Investment News — “Advisors say more clients are seeking to headline-proof their portfolios” by Greg Greenberg
Stacking Benjamins Episode 1840 — “Why 67% of Americans Fear Running Out of Money More Than Dying”; stackingbenjamins.com
Stacking Benjamins Vault — stackingbenjamins.com/vault
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201
Our Mentor: Simone Stolzoff
Big thanks to Simone Stolzoff for joining us today. To learn more about Simone, visit Simone Stolzoff. Grab yourself a copy of the book How to Not Know: The Value of Uncertainty in a World that Demands Answers
Our Headline
Doug’s Trivia
- Wild Bill Hickok was killed in a western town that later became the name of a hit HBO series. What was the name of the town and the series?
Better call Saul…Sehy & OG
Stacker Kathy writes in after hearing a previous episode about Gen X and retirement fears. Her story pushes back against the idea that all Gen Xers are behind. She opened a Roth IRA in 1998, maxed it out every year until 2024, and now has a Roth worth $511,000 as one piece of her retirement. She also built a rollover IRA worth more than $1 million, paid off her home, avoided debt outside of a mortgage, and stopped full-time work at 55.
Have a question for the show?
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- Check out The 201, our email that comes with every Monday and Wednesday episode, PLUS a list of more than 19 of the top money lessons Joe’s learned over his own life about money. From credit to cash reserves, and insurance to investing, we’ll tackle all of these. Head to StackingBenjamins.com/the201 to sign up (it’s free and we will never give away your email to others).
Other Mentions
- The Good Enough Job: Reclaiming Life from Work by Simone Stolzoff
Join Us Friday!
Tune in on Friday when we’re diving into the difference between one-way and two-way door decisions, why some risks are worth taking, and how to stop uncertainty from quietly running your financial life.
Written by: Kevin Bailey
Miss our last show? Listen here: How Much Should You Really Save Without Hating YourLife?
Episode transcript
[00:00:00] opener: They’re dogs and they’re playing poker. Ah, [00:00:15] Doug: Live from Joe’s mom’s basement, it’s The Stacking Benjamins Show [00:00:29] Doug: I’m Joe’s mom’s neighbor, Doug, and to put it mildly, things have been a skosh uncertain lately, haven’t they? Between AI, Iran, inflation, and that dispute at the pickleball court last week, there’s a ton to worry about. Today’s mentor is a guy who studied how to keep it all together in the face of uncertainty, and today he’s going to share his findings with you. [00:00:51] Doug: Simone Stolzoff. In our headline segment, lots of investors are choosing a horrible way to deal with uncertainty. What is it? We’ll jump in. Plus, you asked for it, you got it. Let’s bring the best trivia question ever right here to your listening device. And now, here come two guys who are listening for the sounds of better money habits coming from your house. [00:01:13] Doug: It’s Joe and O. J- J- G. [00:01:20] Joe: Hey there, Stackers. Welcome back to the greatest money show on earth. This is Stacking Benjamins. Super happy that you’re here with us. Super happy the guy across the card table’s here with us, Mr. OG, back again by popular demand. How are you? [00:01:32] OG: Super, super-duper happy. [00:01:33] Joe: Super- [00:01:34] OG: Super-duper-duper happy [00:01:35] Joe: super beyond happy. Yeah, it’s a great Wednesday here. We’re talking about uncertainty, but there is no uncertainty here. We’re gonna have a great episode. [00:01:43] OG: There’s some certainty that we will, yeah. [00:01:45] Joe: There’s some- [00:01:46] OG: Uncertainty whether or not… Certainly our plan- It is- … to have some certainty … [00:01:49] Joe: it is, that is true. [00:01:51] Joe: And like any greatest money show on earth, you’ve, we have no idea what’s gonna happen here. We’re [00:01:56] OG: pretty sure. [00:01:56] Joe: Stuff tends to happen, and it goes even better than we thought. So strap in, everybody. Okay. Grab your favorite note-taking device. Simone Stolzoff, in his earlier work, OG, he dealt with this idea of the good enough job, right? [00:02:12] Joe: That w- we’ve heard this thing from people that are already very wealthy, “Hey, chase your passion.” And he’s like, “Yeah, it’s good enough to not have your job be your passion, but make sure that you’re getting- joy out of your life. So- Have [00:02:26] OG: you seen the bit from, uh, Scott Galloway on The Bill Maher Show about this? [00:02:31] Joe: I can only imagine after the bits he did on our show about this topic. [00:02:36] OG: I’ll see if I can’t find it. Maybe we’ll, maybe we’ll have a little segment maybe after the show- [00:02:41] Joe: Oh … [00:02:41] OG: where we have some things that we’ll- [00:02:42] Joe: Oh, huh, that’d be interesting. Never done that before, but, uh, love the idea. Simone today is going to tackle this idea of uncertainty, and we all feel so much angst, OG, because you wanna look into the crystal ball and predict the future. [00:02:58] Joe: You know, I think it’s why people watch CNBC and Fox Business is, “Oh, hey, I wonder what’s gonna happen next. Let’s get an idea of what ha- next.” Well, Simone’s gonna cover that today and how do we actually navigate uncertain waters. It’s a topic I’m sure even in financial planning, OG, you deal with with clients all the time. [00:03:15] OG: Certainty and uncertainty? Yeah. Yeah. I’d say so. [00:03:18] Joe: Yeah. [00:03:18] OG: It’s a common theme. Yeah. [00:03:19] Joe: It’s… So today we’re diving into that. We have only a couple of sponsor spots on the show. We have one right now and one at the midway point during the middle of Doug’s trivia, which Doug, uh, no hyperbole today, you set the bar fairly high. [00:03:35] Joe: Best trivia ever? [00:03:36] Doug: Pretty sure. Pretty sure. [00:03:38] Joe: I’m super excited to hear that one. We have a couple sponsor spots there. We have a couple right now, beginning with the Vault. The Vault is the way you get seven different things that you’re trying to solve using your phone all in one place: your privacy, your credit, your subscriptions. [00:03:55] Joe: Coming, man, I, I know I’ve said this a lot, I know I’ve said this a lot lately. Coming very, very, very soon, your budget and your net worth tracking. Stackingbenjamins.com/vault gets you there. Go check that out, and, uh, we’re happy to see so many exciting things from Stackers that have used the Vault. People saving a lot of money, people also getting their financial house in order. [00:04:20] Joe: We have a couple more sponsors who help us keep on keeping on. We’re gonna hear from them, and then we’re talking uncertainty with Simone Stolzoff. [00:04:36] Joe: And I’m super happy we finally have this gentleman coming down the stairs to mom’s basement. Simone Stolzoff’s here. How are you? [00:04:42] Simone: Doing well. Thanks for having me. [00:04:44] Joe: As you have pointed out so often lately, we are living in a more uncertain world than ever before, and I love this idea that, you know, humans have always tried to predict the future, and now I’ve got my brokerage app and a mild anxiety problem. [00:05:00] Joe: So, you know, in the past people tried to read bones, and now we refresh our accounts all the time, like, “This time I’ll understand what’s happening.” Why are we so bad at just being comfortable not knowing, Simone? I [00:05:13] Simone: think there’s two things going on right now. One is that the world is very uncertain right now. [00:05:19] Simone: So if you look at data, there’s this project that tracks the global uncertainty index. That’s basically the vibe of uncertainty across the globe, and the study began in the ’80s. The five highest measurements since the study began were all in the last five years. [00:05:33] Joe: Wow, this is the highest level of all time. [00:05:36] Simone: Well, I don’t know about all time. If you were maybe living in Florence during the Bubonic plague- Okay … you might take issue with that characterization. But especially in the last sort of century or so, we have tariffs, we have COVID, we have a war in Ukraine, a war in Iran, and so the world feels more uncertain than ever. [00:05:53] Simone: And the other thing that’s happening is that our tolerance for uncertainty is in decline. So there’s this… been some really interesting research from this researcher named Nick Carlton who found that the rise of mobile phones and the internet in particular have created the expectations that answers should be readily available, and I think in an investing context we see this all the time. [00:06:14] Simone: Whereas the Wall Street Journal might have published the stock results at the end of the day in the late ’80s or early ’90s, now we literally can swipe down and get minute to minute results. And, you know, as an analogy to the rest of the information economy, this access to more information has not made us any wiser, has not necessarily made us better investors. [00:06:35] Simone: It’s made us more anxious, because we always have the ability to seemingly control how our portfolio is doing. [00:06:42] Joe: Well, it has been that way with our career too. I mean, a lot of our show also is about earning money, and I think that uncertainty exists in the workplace as much. [00:06:51] Simone: Yeah, very much so. You know, I think especially in the last three to five years since the beginning of the pandemic, we’ve seen the average tenure of a job decrease. [00:07:00] Simone: We’ve seen entire industries be upended or undermined by new technologies. And so I think people are feeling like a lot of the toeholds, a lot of the things that once gave their life more stability, like the loyalty of a profession or maybe a neighborhood or community group or the community you found at the workplace are starting to break down at this exact same time. [00:07:22] Joe: We’re gonna go through a series of tactics and strategies that we can use to make ourself more calm and more comfortable with the current environment that we’re in. You mentioned our phone. Could the beginning of our answer be just put the damn phone down? [00:07:37] Simone: I think that’s definitely part of it. You know, I think especially when it comes to thinking about finances, often the best thing that you can do is create rules, and so you’re not making emotion-based decisions, and you’re actually following some discipline about how often you’re checking and how often you’re rebalancing your portfolio. [00:07:56] Simone: I think it was Warren Buffett who said, “Uncertainty is actually something that is in favor of what a buyer should be looking for. Uncertainty creates opportunity.” I talked to a bunch of venture capitalists and investors for the book, and they said in the best deals, there’s always a lack of consensus. If everyone agrees that something is a good deal, it is often already baked into the price. [00:08:17] Simone: You know, buying Apple is not necessarily a contentious decision. But when there is that level of uncertainty, that also creates that level of opportunity, and so I think you need to balance those two things. How can you create boundaries and systems to prevent yourself from being on tilt or making emotional-based decisions? [00:08:34] Simone: And how can you also see that uncertainty is not necessarily a problem to be solved, but something that we all have to manage in our life, in our careers, and in our portfolios as well? [00:08:43] Joe: It’s interesting. You lay the groundwork for this whole discussion with a story that made me very uncomfortable, I think on purpose, about a couple and about this relationship that they have that has been going the wrong way. [00:08:57] Joe: Do you mind kind of laying the groundwork, talking about this couple and this big inflection point in their relationship and how they decide to handle it? [00:09:05] Simone: Yeah. So fascinating story, true story. There’s this couple, Connie and Andrew, and they’ve been together for 17 years, married for 10 years. But they both feel that something isn’t quite right in their relationship. [00:09:18] Simone: They can’t necessarily put their finger on it, but they’re out having a drink at a bar, and they decide to do something that others might seem as crazy. They say, “For a year, we’re not gonna talk to each other at all. We’re gonna go our separate ways and then come back to the same bar a year from today and decide whether we wanna stay together.” [00:09:39] Simone: Yeah. [00:09:39] Joe: I got to that point in the story and I’m like, “I could not imagine.” Talk about uncertainty. That is a risk. [00:09:44] Simone: Yeah. They called it the year of living dangerously, which I think is a great name. But, you know, I think there’s a few aspects to it that is interesting to me. One, I think most couples in this situation would either just carry on or break up right then and there. [00:09:59] Simone: But they created sort of a framework to play with, to sort of collaborate with the uncertainty that they were feeling, and try to come to a resolution themselves. And I won’t spoil the ending. You’ll have to read the book in order to figure out what happens. But I do think this perspective around uncertainty being something that we don’t necessarily have to rush to an answer to resolve as being an enlightened way to come to more innovative solutions, to be able to find ways to collaborate with people that might not have the same views as us. [00:10:30] Simone: For an organization to get to breakthrough ideas, if you’re willing to tolerate the risk that is inherent with facing uncertainty, is a lesson that we can all learn from. [00:10:39] Joe: Well, and I wondered as I was reading that story, you know, a lot of people come to Stacking Benjamins because they Googled, “I hate my job.” [00:10:48] Joe: I wanna find a way to make my investments do better so that I don’t have to work at this job anymore. And for all those people listening, even if they’re just a little bit uncertain, is there a context there where I need to sit my job down and go, “Hey, maybe we need a little space”? [00:11:04] Simone: Yeah, maybe we need to take our own year of living dangerously. [00:11:07] Joe: Yeah. [00:11:07] Simone: I definitely think it helps to understand our biological response to uncertainty. So you think about our ancestors, if they’re, you know, in hunter-gatherer society, if there’s a rustling in the bushes or there’s a berry that they’ve never seen before that could potentially be poisonous, it makes sense to try to seek certainty. [00:11:29] Simone: That’s why certainty makes us feel so safe and secure. That’s why we like music that’s based on repeating patterns, where you can anticipate what’s to come. But the problem is we still have this sort of life or death mentality towards uncertainty in our modern lives that are full of uncertainty. So how many of us know someone who is maybe in a job that they know they don’t like, but they’re too uncomfortable with uncertainty to explore something else, or maybe a relationship that they know is not best for them, but they would rather praise the sort of devil you know, the comfort of their current status quo, rather than taking a risk? [00:12:07] Simone: I don’t think I can give sort of prescriptive one-size-fits-all advice about whether or not you should quit your job, but I do think having a sound financial portfolio can give you a foundation that allows you to be a little bit more comfortable with any uncertainty you may face moving forward. [00:12:23] Joe: It’s almost like separating the controllables from the uncontrollables. [00:12:27] Simone: Yeah, I like that a lot. You may be familiar with, uh, the Serenity Prayer. “God, grant me the grace to understand what I can control, what I can’t control, the wisdom to know the difference.” And I think that’s very true when it comes to our careers. There are some macro factors about the economy that you don’t have an ability to control. [00:12:48] Simone: But if you are able to, say, focus on what is in your purview, whether it is learning about some of these AI tools that are causing you anxiety, exploring new opportunities that might exist for you. You know, one of the big pieces of advice I give in the book is to find your anchors. When we are certain about some aspects of our life, it makes it easier to hold uncertainty in others. [00:13:11] Simone: So maybe for one person, it is an anchor to know that they want to plant roots in a given city, or to be with a given partner, or to know that they have three to six months of liquid savings that can allow them to take more risks in their equity portfolio. But once we know those anchors in our lives, it makes it easier to hold the uncertainty that we’ll inevitably face in the future. [00:13:32] Joe: Yeah, like I can go grab onto that anchor. I love that anchor analogy because now I’ve got something to grab onto as the… I don’t know what the analogy is. The wind gets strong or the waves get strong in life. [00:13:42] Simone: Yeah. I like, um, the steady boulders amidst the changing winds. [00:13:45] Joe: Yeah. And what’s funny is there’s a feeling that you explained that this creates having our anchors, and it’s in Intimacy. [00:13:53] Joe: But to get there, you use this great story about a monk that I think illustrates this really well. I was like, I even read this, Simone, and I went, “Wait, what?” Like Yeah. ‘Cause where ends [00:14:05] Simone: is not- That’s the point of a lot of, of these Buddhist teachings, these koans, you know? It’s like trying to break you out of your routine of thinking there are easy answers. [00:14:14] Simone: So I’ll give you a little bit of a backstory. So in San Francisco, I live in actually my childhood home that I grew up in, and I’m a full-time author. And my wife and I got pregnant with our first kid, and I was feeling so anxious, so anxious about how I was going to afford paying for a kid on sort of an artist’s salary, anxious about the world that this kid was going to grow up in. [00:14:40] Simone: And so I started going to this place called the San Francisco Zen Center, which is like a, a meditation meetup group. And one of the weeks, the person who was sort of presiding over the group told this story about these two monks that meet in the woods. They’re sort of the teacher and the student monk. [00:14:56] Simone: The teacher sees the student and says, “Hey, what are you doing here?” And the student says, “Oh, I’m going on a pilgrimage.” And the teacher says, “What are you on a pilgrimage for?” And the student says, “I’m not sure yet.” And the teacher says, “Not knowing is the most intimate.” And at first, you know, I heard this story and I was like, “What the hell is he talking about?” [00:15:16] Simone: You know, like- [00:15:17] Joe: Me too when I read you. Yeah, [00:15:18] Simone: exactly. It’s like, you know, the most intimate. Like, when I don’t know something, the thing I feel most intimate with is Google, you know? I look things up. But the wisdom of the teacher is that by suspending the need to know, suspending the need to grasp for, for certainty, we open ourselves up to what may emerge. [00:15:38] Simone: And so the student might be able to discover the purpose of his pilgrimage as he goes through the journey, rather than thinking it’s gonna deliver something very particular. And I think it’s a great metaphor for life. You know, as we think backwards, there’s probably moments of uncertainty that we’ve all faced, maybe after a layoff or after a breakup or after a transition where we really didn’t know what the future was going to hold, and our job is to not close ourselves off. [00:16:05] Simone: Our job is to stay open to what might emerge. I think that is really the upside of uncertainty. We often see uncertainty as a threat or we see it as a source of fear, but it can also be the birthplace of possibility. It can be the place where something emerges that we didn’t know previously could have emerged. [00:16:24] Joe: I feel I can also… What’s that Bruce Lee quote? It can also make you more like water. Doesn’t he say something about that? [00:16:29] Simone: Yeah, be like water. Exactly. [00:16:31] Joe: Yeah. I’m gonna be more open to the uncertainty and the fact that I don’t know, and then I’m just gonna flow wherever it flows and feel the feelings, and that will give me a better outcome than worrying nonstop about which way the water’s going to flow. [00:16:43] Simone: Yeah. I’ll give you one anecdote from the business world that actually isn’t in the book, but I think might be illustrative for our listeners. There was a startup in the early 2010s in San Francisco, and it was a, a gaming company. It was this massive online multiplayer game. And it was super hyped. It raised $17 million before it had even launched. [00:17:03] Simone: Its launch was covered in The New York Times. It had tens of thousands of active players in its first week that were playing the game for 20 hours at a time. And yet the founder thought there was something off, that he couldn’t necessarily put his finger on it, but he felt like the company itself wasn’t sustainable. [00:17:22] Simone: And so he did something that others might see as crazy. He decided to shut the company down, sort of at the peak of its success, and he made his investors whole. He gave his employees the opportunity to leave if they wanted to. And then with the remaining employees, he decided to build a new business in a completely new industry. [00:17:41] Simone: While they were building the game, they had built this internal communications tool to collaborate as a team, and he decided to build a company around this internal communications tool. That tool is the tool that you might be familiar with called Slack, and that startup became the most valuable B2B software company of all time. [00:18:00] Simone: It sold to Salesforce for, I think, $28 billion. And I think the point of the story is sort of similar to the, the story of the monk, where the founder, Stewart Butterfield, didn’t know necessarily what would emerge if he chose to turn toward the uncertainty of this new problem or this new business opportunity. [00:18:19] Simone: But by opening himself up to that uncertainty, he was able to discover something that was actually even bigger than the opportunity he was going for initially. [00:18:27] Joe: Imagine the fear everybody has. [00:18:29] Simone: Totally. “ [00:18:30] Joe: Wait, we’re doing what?” And [00:18:31] Simone: then- “Yeah, we’re pivoting completely. I thought we were a gaming company. Now we’re trying to create a workplace tool.” [00:18:36] Joe: Which by the way, I’m sure 99% of our stackers have heard of Slack. I’ve got Slack open right here with my notes on it for this interview. [00:18:46] Simone: There you go. I don’t know if Microsoft Teams has as sexy of an origin story. [00:18:50] Joe: No. I don’t think so. I wonder if the Acquired podcast has heard that Slack story yet, if that’s on- Hmm [00:18:57] Joe: the docket coming up You know, it’s funny, I love case studies. [00:19:02] letters: Mm-hmm. [00:19:02] Joe: And I know a lot of our stackers love case studies. I love the stories you’ve shared so far. But there’s a guy who is prominent in this work named Max, who kind of made himself a case study for exactly Simone, exactly what you’re talking about. [00:19:18] Joe: Can we talk about Max for a second and this dude kind of going over the, the edge on all this let’s embrace uncertainty thing? [00:19:25] Simone: Yeah. As a journalist, I’m always looking for those edge cases or those eccentric characters, and Max definitely fits the bill. He was a software engineer at Google. [00:19:33] Joe: How did you find him, by the way? [00:19:34] Joe: That just is the journalist piece? How did you find Max? [00:19:37] Simone: Yeah. It’s sort of like a friend of a friend of a friend- Okay … kind of thing. You know, this is my second book, and all of my books are very narrative driven, so each chapter is a story, a little case study, as you mentioned. And I’m always looking for people who might be able to shed some insight or light on the broader topic in a given way. [00:19:54] Simone: And so I started talking about, “Hey, I’m writing this book about how to get better at dealing with uncertainty. Does anyone know someone I should talk to?” And I got the recommendation to talk to this guy, Max. And so he was a software engineer at Google. He lived this sort of charmed life. He had everything dialed. [00:20:08] Simone: He knew his perfect bike route to get to work. He was making lots of money. He had his sort of go-to spots in his neighborhood, but he had this uncanny feeling like he was acting out a script that was written by someone else, or he was, like, reading a book that has already been read, that he’s just kind of going through the motions of his life. [00:20:28] Simone: And so he decided, software engineer that he was, to try to fix the bug, to try to get at sort of the, the heart of what was bothering him. And he realized that he was sort of in this bubble, and so he was looking for ways to get out of the bubble. First thing he did is he created a software program that would call an Uber to his house and take him to a destination known only to the driver. [00:20:52] Simone: So he’d get in the Uber, and the driver would drop him off at some place in the city. So he went to the Castro, which is the gayborhood in San Francisco. He went to a bowling alley on the other side of town. He went to … His first ever trip dropped him off at the psychiatric emergency room at the general hospital. [00:21:09] Simone: And so it was just sort of, like, a way to, like, get random … Yeah, this may be a sign from the- [00:21:14] Joe: You actually wrote, and I thought it was pretty funny, “Maybe that was a sign of things to come.” When they drop him off- Yeah, exactly … in front of the psychiatric hospital, like, really? You want to do this? [00:21:22] Simone: Well, so, you know, this was just the first experiment, and then he created another app that would take him to random restaurants around the city. [00:21:30] Simone: And then he created another app that would send him random clothing items off of Amazon each week. And it took this to the furthest extreme where he ended up quitting his job and designing an app to tell him where he should live around the world. And for two years, every month, he would sort of roll the dice and listen to the computer, and the computer would send him to Ho Chi Minh City, Vietnam, or to Gortina, Slovenia, or to Amarillo, Texas, and all of these places that he had never been to. [00:22:06] Simone: And he would sort of show up and then figure out how to live his life in those places. And it’s, you know, a fascinating study. Like, he has so many interesting anecdotes that I cover in the book. But I think the sort of macro point I learned from a psychologist that I interviewed and told him about this story, and he said, “When we are intolerant of uncertainty, we normally have one of two different reactions.” [00:22:31] Simone: So he said, “Imagine that you are going to buy a new pair of jeans. If you’re really uncomfortable with uncertainty, you will either try to try on every single pair of jeans in the store before making a decision or just buy the pair of jeans in the window.” They’re both sort of impulsive choices to get out of having to deal with the uncertainty of having to make the decision for yourself. [00:22:53] Simone: And so at first, I thought Max’s story was this brilliant case study of someone who was really willing to turn toward the unknown. But after reflecting and talking to Max and talking to some experts about it, I realized that just sort of leaving all of your life to chance is another way of circumventing having to grapple with the uncertainty that you may be feeling. [00:23:13] Simone: And so I think the sort of more adaptive version is to find that middle ground, where hopefully you are introducing some novelty in your life, trying restaurants that you’ve never been to, striking up conversations with strangers that you might not otherwise strike up. But you also have some of those anchors, some of those certain aspects of your life that makes it easier to build towards something as opposed to just sending out all this energy in all these directions. [00:23:38] Joe: It sounds like you’re advocating that contemplating the uncertainty in the decision and almost partitioning off the places where you know there’s uncertainty and becoming okay with it is really where we wanna be versus I’m going to have the Max random thing, and then to your point that I don’t deal with at all. [00:23:55] Joe: It reminds me, I’m a guy who’s afraid of everything. And during my career, I’ve had this mantra that I have to tell myself fairly often, which is feel the fear, but do it anyway. Because every time I do it and I embrace it, good happens. Like every- Totally … every, every time, good stuff. But I have to convince myself to do it. [00:24:14] Joe: But it sounds like what you’re talking about is also this contemplative- Anchor. Not just an anchor, but a very contemplative, “I’m anchored here, but I’m looking off and I need to contemplate this darkness and this fog around me,” and then venture out. [00:24:27] Simone: Yeah. I love that. Yeah. There’s a metaphor that I use in the book that living is like being on a rowboat on a lake that’s shrouded in a heavy fog. [00:24:36] Simone: You might not be able to see very far in front of you. You might not be able to know exactly where you’ll end up, but you have two jobs. One is to maintain faith that you’ll eventually reach land. Remember, you’re on a lake. And then the second is to keep rowing. And I think that action is what absorbs the anxiety, you know? [00:24:54] Simone: By doing the things that you’re scared of and figuring out what’s on the other side, that’s how we grow. That’s how we learn But I also think there’s some balance to strike. So let’s take an investing example, for example. So say you want to pick individual stocks and sort of play in the sandbox of investing. [00:25:11] Simone: That can be fun. It can potentially be rewarding, but you also need some structure and some rules around how you’re playing with your money so that you don’t just gamble it all away. In the book, I talk about this concept called kill criteria, which are things that will keep you from either going down to zero or continuing to invest your money past the point where you’ve already made a lot of gains. [00:25:40] Simone: So in the investing world, it’s often called, you know, stop-loss orders, where you buy a stock for 100 and you say, “If it goes down to 50, I’ll definitely sell. If it goes up to 150,” you’ll definitely sell. And there’s a, a story that I talk about in the book about climbing Mount Everest. When people climb Mount Everest, there is a turnaround time, which is to say that when you’re a certain level up the mountain, by 2:00 PM, you have to turn around no matter where you are. [00:26:07] Simone: And the reason they have this rule is because it saves people’s lives. When you’re so close to the peak of the mountain, it’s really tempting to be like, “Oh, I’m not gonna pay attention to the storm clouds,” or, “I’m not gonna pay attention to the fact that the sun is setting in the sky. I’m gonna make a push for the summit.” [00:26:24] Simone: And that’s when people get hurt. And so the point of creating kill criteria or stop-loss orders is to pre-commit to these rules. Because in the moment, you might want to make an emotional decision and say, you know, “Bitcoin’s going to the moon. I’m just gonna keep buying, buying, buying” or like, “I’ve lost, you know, $5,000 at the craps table. [00:26:46] Simone: I’ve got to, like, earn it back by continuing to bet more.” And by pre-committing to how you’re gonna act, you can make more sound and rules-based financial decisions as opposed to just making decisions based on your emotions. [00:26:59] Joe: That’s interesting. We talk about that in relation to a device called investment policy statement a lot. [00:27:04] Simone: Mm. [00:27:05] Joe: Which is I’m going to create these rules around my investing, and every time I invest, I’m only gonna look at my portfolio on X days, but do that ahead of time. You don’t know if it’s a good day or a bad day ahead of time, so you don’t know how emotional you’ll be, which is perfect, so you’re taking the emotion out of the game, and then you work from there. [00:27:21] Joe: I want to ask you that even more about financial planning, ’cause I’ll bet that during all these interviews you’ve been doing lately talking, you probably are talking about financial plans a lot. But it strikes me that- When we’re building financial plans, right, somebody’s building their financial plan for the future, are we building plans? [00:27:38] Joe: Are we just writing a confident guess? And is that guess then making us more confident to make the moves to find financial independence? [00:27:46] Simone: Well, it’s a bit of both, right? You know, I think with anything about the future, it is a guess. You can’t be certain about how a given index fund or a given stock will perform or whether this asset class is worth investing in right now at this moment in time. [00:28:01] Simone: There’s this psychology professor who I quote in the book who collated data from a decade worth of predictions from experts, so economists, politicians, journalists, et cetera. And his finding was the average expert was roughly as accurate as a dart-throwing chimpanzee. Which is to say, like, even the most, you know, heralded people that give financial advice aren’t very good at predicting the future on an individual basis. [00:28:27] Simone: That being said, the things that you can do by creating a plan are to, for example, diversify your portfolio, which is a hedge against uncertainty. When you have a diverse portfolio, it allows you to be able to absorb some of the risk and uncertainty that’s inherent in anything worth investing in, like real estate, like stocks, what have you. [00:28:48] Simone: I also think it’s important from a career perspective to diversify our identities or our sources of meaning for the exact same reason, which is to say that a given job might not always be there. You know, I speak to lots of recent retirees in my labor reporting and my research who basically stake their entire identity on one particular job or one particular employer, and maybe because of retirement, maybe because a layoff or a furlough, that job can be taken away from them. [00:29:17] Simone: So similar to our financial portfolios- Diversifying our identities allows us to be able to weather some of the inherent uncertainty. So make a plan. I think one of the benefits of working with financial professionals is they can help balance a portfolio so that you are diversified, and know that any sort of investment or any sort of opportunity comes with some level of risk. [00:29:42] Simone: When it comes to anything in the future, there is no certainty, and convincing ourselves of anything other than that is a fallacy. [00:29:49] Joe: It strikes me over the course of our discussion today to kind of get people comfortable with what you’re talking about. There’s almost this edge where I wanna have my anchor that gives me comfort, but I would also think, Simone, that from some people there would be this feeling that I need more anchors. [00:30:10] Joe: Like, I anchor again, I anchor again. I need more planning, I need more planning, I need more planning, and I use that as an excuse to never do anything. Where on the other side, there’s people like Max, who one day realizes, and I love this, he’s like, “Wait a minute, what am I building? I’m not really building anything. [00:30:24] Joe: I’m just kinda doing stuff, and it’s not really leading anywhere.” Is there a way for us to kinda know, okay, this is too much planning, this is too much winging it? [00:30:34] Simone: Yeah. Well, I’ll give you two frameworks that might be helpful. They’re both from Jeff Bezos. One is Bezos says that you should ship something, so you should publish or launch or do something when you feel 85% ready. [00:30:47] Simone: Because if you wait till you’re 100% ready, one, that day may never come, and two, it’s likely too late The second thing that Bezos says is you have to distinguish between one-way door and two-way door decisions. So one-way door decisions are decisions that are really hard to reverse. It’s like walking through a one-way door. [00:31:06] Simone: It’s hard to come back through them. And two-way doors decisions are decisions that we can often course correct or reverse if we have to. So often we treat two-way door decisions as if they are one-way door decisions. We sort of white-knuckle grip these decisions of our life and discount our own ability to adapt or course correct if something were to go wrong. [00:31:29] Simone: That isn’t to say that all decisions in your life are two-way door decisions. When you’re deciding, for example, whether to buy a house or who you want to marry, those are the types of one-way door decisions that make sense to really contemplate and have your research be thorough. But for the two-way door decisions, often we try to make perfect the enemy of good, and we discount our ability to make decisions right after we make them. [00:31:55] Simone: You know, I think one thing that I talk about in the book is what makes a hard decision hard is that one option is not clearly better than the other. If that were the case, it would be an easy decision, right? Right, right. What makes a hard decision hard is that there are trade-offs. So I’m thinking specifically about one moment in my own career where I was choosing between two jobs, and one job was to continue to be a magazine writer at this trendy magazine. [00:32:18] Simone: I also had another job offer to work for this design agency, which paid more, and for weeks I couldn’t make up my mind. I kept sort of waffling every day. I’d think that another decision would be better. I talked about it with my Uber driver and my yoga teacher. I was insufferable. And what I realized looking back is that I was looking for certainty where there was no certainty to be found. [00:32:40] Simone: Like, how could I know what job was right for me before I’ve actually done the job? And I think there’s so many different analogies. How could you know what person is right for you to date until you’ve actually gone on the date? How could you know what career path to pursue once you’ve gotten proximate to the work itself? [00:33:00] Simone: It is through action, it is through building, that we actually can learn much faster than these thought experiments that we tend to play in our own minds. [00:33:08] Joe: Which is a great reminder, I think, to us to stop spending so much time on the decision, spend more time on making the decision you decided on the right one. [00:33:17] Joe: Right? You know what I mean? Actually get more invested in not second guessing yourself. I feel like we second guess ourselves way too much instead of getting more invested in making sure that this was the right answer for us. [00:33:29] Simone: Well, that’s why I wrote the book. You know, the cliche among authors is that you write the book that you need to read. [00:33:34] Simone: And I have this natural tendency to ruminate, to second-guess myself, to play devil’s advocate for every decision that I make. And part of the sort of wisdom that I learned through, you know, multiple years of reporting this book is that uncertainty is an inevitable part of life. It’s an inevitable part of making decisions. [00:33:55] Simone: It’s inevitable part about living and thinking about the world. And so rather than trying to eliminate uncertainty or eliminate risk or eliminate ambiguity, we have to develop a tolerance for uncertainty to be able to make commitments in spite of doubt, as opposed to waiting until we have no doubt at all. [00:34:16] Joe: Suman, I, I’m so glad that you went down this road yourself and it was such a personal journey because it’s so personal for many of our Stackers, and it hits the nail on the head. One of the biggest problems in financial planning is not the markets, it’s not the strategies, it’s that we get in our own way. [00:34:33] Joe: I love the fact that you take us through how not to get in our own way when there’s uncertainty. Your brand-new book is called How to Not Know: The Value of Uncertainty in a World That Demands Answers. It was available everywhere last week, right? [00:34:47] Simone: Yeah. It just came out. I’m so excited for people to read it. [00:34:51] Simone: You know, part of the reason why you write a book is to be able to connect with people. So if you read the book, please let me know. I’m also offering a bunch of bonuses for the first readers. So if you order a book today, you can get an invitation to an exclusive event I’m doing with the author Michael Lewis, who wrote- Never heard of him [00:35:07] Simone: Liar’s Poker and Moneyball. I have no idea. Who are we talking… [00:35:09] Joe: Michael who? [00:35:10] Simone: I also have a guide to dealing with uncertainty in your career, that just for some of these first readers. So thank you so much for having me on the show, Joe, and I look forward to hearing about your own trials and tribulations with uncertainty as we continue to live in this world. [00:35:25] Joe: Thank you so much for mentoring all of our Stackers today. I appreciate the time and the energy you put behind this so much. [00:35:31] Simone: Thanks for having me. [00:35:37] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and, yep, Simone hit the nail on the barb. It’s like the Wild West out there, isn’t it? Well, funny coincidence, because today’s the birthday of one of the best known wild frontier lawmen of all time, Wild Bill Hickok. Hickok and yours truly have a lot in common. [00:35:55] Doug: Hickok was the fastest gun in the West, and I’m not one to brag, but I’m the fastest with the meatloaf fork, according to Joe’s mom. Hickok also liked to sit with his back to the wall when he played poker. Same for me, but, you know, between us, it’s because there’s a mirror on the opposite wall and it helps me see what OG’s holding. [00:36:12] Doug: I know what you’re thinking. That’s cheating. I thought so, too, until I realized how unlikely it is that OG has five aces nearly every hand. Ain’t nobody that lucky. Anyway, here’s today’s trivia question. HBO made a ton of Benjamins off a series titled the name of the same town where Hickok was murdered. [00:36:33] Doug: What’s the name of the town/series? I’ll be back right after I go see if we can put up another mirror behind Joe while we play. I’m still losing too many hands to these guys. [00:36:46] opener: We’re looking for the answer and correct spelling. Old MacDonald had a what? Farm. E-I, E-I-O. [00:36:58] Doug: Hey there, Stackers. I’m poker lover and guy who’s the sheriff of all good trivia in these here parts, Joe’s mom’s neighbor, Doug. Today we’re celebrating the birthday of Wild West sheriff Wild Bill Hickok. Not only did he love taming the lawlessness of the Wild West, but he also liked cards, and sadly, it was at a card table that he died with what they now call a dead man’s hand: black aces and black eights. [00:37:24] Doug: HBO made a ton of money on a top series named after the western town where Bill lost his life. What was the name of that town? Released way back in 2004 and still carrying a very high 8.4 rating on IMDb, the series was called Deadwood. And if you wanna hear more about the Wild West and what it has to do with your money, go back and check out our episode called Panning for Profits from June of 2023. [00:37:51] Doug: It’s a great one. I’ll have my people link to it in the show notes. Hey, people, do that magic stuff. And now back to two guys who are taming the lawlessness in your wallet, Joe and OG. [00:38:05] Joe: Thank you, Doug, and thank you to Simone Stolzoff for stopping by. You know, it’s interesting, OG, this idea of, uh, uncertainty just carries over to everything. [00:38:15] Joe: In fact, we have a headline about it [00:38:18] headlines: Hello, darlings. And now it’s time for your favorite part of the show, our Stacking Benjamins headlines Our [00:38:24] Joe: headline today comes to us from Investment News, the trusted resource for independent-minded advisors, is what they say. I tend to like this publication, and I also like the fact that, Stackers, we get to kinda look at what advisors are thinking about on the other side of the table. [00:38:40] Joe: Uh, this is from their practice management column, and it’s written by Greg Greenberg. Greg writes, “Advisors say more clients are seeking to headline-proof their portfolios.” Get this. Greg writes, “After months and months of headline whiplash,” I just love journalism, “more and more wealth management clients are asking their advisors to build them portfolios that can absorb the bumps without forcing emotional decision-making.” [00:39:10] Joe: I wanna dive into these words. The word forcing here, OG, seems to me to be very, very forced. I [00:39:18] OG: wouldn’t get past the first sentence of this article before, like, just, like, literally ripping the page out of this- … publication and burning it. [00:39:26] Joe: And that, Doug, is 100% the reason why I wanted to bring this one to the table. [00:39:31] Joe: I’m like, OG’s gonna have a field day. And especially after Simone just got done telling us about, “Hey, the only thing that’s certain is uncertainty,” nobody’s forcing you into emotional decisions. Greg continues, “Yep, to adapt the old network quote, they’re frustrated as hell, and they’re not gonna take it anymore.” [00:39:48] OG: Yes. Clients are super frustrated that the market has gone basically straight up for the last 15 years. They’re really ticked off about that. I’m so over it. Oh my gosh, the horror, the horror. I’m so done [00:39:57] Doug: with it, man. [00:39:58] Joe: Well, and this is the problem, right? My question is, why are we asking advisors to mitigate the fact that I watch the news minute by minute, and I’m following it entirely too closely? [00:40:11] Joe: Like, it’s, it’s… I think what they’re asking, OG, is for their advisor to walk them off the ledge that they put themselves on. Like, why are we watching the news- Yeah … every single second? [00:40:19] OG: So I hear this storyline that you’re talking about, and immediately I think, “Okay, the great news is, is that our business is future-proof for a while,” because if this is actually the case, that means that there’s millions of people out there who are just solely focused on the day-to-day market investment returns, and haven’t been converted yet to the idea of planning for your own personal financial success, and then building an investment plan that is unique to you that reaches your goals regardless of what happens, uh, you know, with who does what on CNBC. [00:40:58] OG: And, and so I feel really good about this, like, “Oh, good, I’ve got a job tomorrow.” That’s, that’s, uh, really great news. I don’t know that, at least in the last, I don’t know- Golly, since COVID? I don’t know that we’ve ever had anybody. I– So last year, I have this habit of, not habit, it’s not the wrong word, but, um, uh, philosophy maybe, that when we get to roughly correction territory, which– So to define a correction would be a closing value that’s minus 10% of the high water mark. [00:41:31] OG: So colloquially, that’s what we would say is a correction. The S&P closed at 6,000, and now it’s closing at 5,400. We’re down 10%. That’s a correction territory. You might hear those phrases. You know, that rarely happens in a snapshot. You can kinda telegraph that. You see like, okay, we’re on this path. I start thinking about it. [00:41:50] OG: And so I generally send an email around that time that just says, “Hey, this is normal. It sucks. It doesn’t make it feel any better, but we’re still in normal category territory of this happens a lot, so don’t sweat it.” Uh, last year, in 2025, we had the tariff shock to the market, right? Where the stock market went down a whole bunch in a short period of time, and I debated that. [00:42:11] OG: I was like, I don’t know that I wanna have some, give this energy. You know what I mean? Like this– When, when you, you put some… Your doctor says, “Hey, we don’t really usually test for this, but we’re gonna today,” you go, “Oh, jeez, is this a thing we have to test for?” Like you just, like all of a sudden it’s a thing you don’t know exists now exists, right? [00:42:27] OG: If I tell you, “Don’t think about a pink elephant in your room,” you just immediately thought of a pink elephant. You didn’t even think to think of a pink elephant five seconds ago, right? Yeah. Yeah. So it’s always a catch 22 of whether or not we wanna put any, any, you know- [00:42:39] Joe: If I address it or not. [00:42:41] OG: Yeah, if I put any emphasis on this, if I give it any weight. [00:42:44] OG: But we did. And, and so I sent out an email like I normally do, and it basically said something to the effect of, you know, this is crazy, but it’s still within the realm of reality and, you know, the market has a way of solving this, so just kinda hang tight. By the time April got to the end of April, like it had, the market had solved it, and I was like, “Ah, that was a wasted email.” [00:43:03] OG: You know? I coulda just waited like two more weeks and it’d been fine. I think that people that have well-thought-out financial plans that are unique to them, and then build their investment plan around the goals that they’re trying to achieve, which routinely are things like, “I wanna be financially independent at a certain time. [00:43:19] OG: Um, I have this amount of money to save. I wanna send my kids to college. I wanna give money to the people or places that I care about, and I wanna do so in a tax efficient manner.” When they do that and have that plan for themselves, these day to day, week to week, I mean, hell, month to month market news, air quotes, I’m saying air quotes news, it’s a non-event. [00:43:38] OG: And when you only focus on one particular area of your plan, all you do is focus on the money, then that’s all you have to focus on. You’re not– There’s nothing else to think about. So you think, “Well, this is the thing I must be… You know, this is the thing I’m supposed to be thinking about if there’s only money.” [00:43:55] OG: So if you’re working with a broker and that’s all y’all talk about, “Here’s what the stocks did. Here’s what your mutual funds did. Here’s what your ETFs did. Here’s your portfolio. Here’s the zhuzhing we’re doing because it’s Tuesday,” like exit stage left, man. We need financial planning more than we need day-to-day market movement stuff. [00:44:17] OG: It’s crazy. But great news. Apparently there’s a lot of people out there who still do this, so You know. [00:44:24] Joe: Well, and I love your take on this because controlling this with systems and mindset. I’ve got systems, I’ve got mindset. I don’t need to go watch the news every day. In fact, for people that are still really worried about this and they wanna deep dive into how we think you should look at geopolitical risk, we did an entire episode back, uh, put in, uh, Stacky Benjamin’s 1828. [00:44:46] Joe: We tell you exactly how to handle geopolitical risk. As an example, if you’re watching the headlines too much there. But if you’re, even if you’re just watching the stock market, setting yourself systems is a much better way to go. But it’s funny, OG, as always, we have two ways we can handle this, the way that you just outlined or the Wall Street way. [00:45:08] Joe: And the wrong way. ‘Cause you know, you know what Wall Street’s really good at? Taking something very simple and making some solution that sounds comforting. And the newest comforting phrase that this piece comes up with is a buffer ETF. [00:45:24] OG: Oh, my gosh. So this was a sales article? You SOB, you. [00:45:31] Joe: This is, this is- I, [00:45:32] OG: I actually didn’t see this coming. [00:45:34] OG: Does it say paid promotional thing at the top? That does, that’s not fair. [00:45:37] Joe: It does not, which makes it even more disgusting. So for people that don’t know what this is, markets get volatile, right? Investors get nervous, and all of a sudden Wall Street starts selling you upside without downside, which is kinda like, by the way, asking for pizza that has no calories. [00:45:53] Joe: That’s what, that’s what they always tell Doug down at the pizza place. No, that, that [00:45:56] Doug: exists, though. Yeah. The thin crust stuff. That’s diet pizza. I don’t- [00:46:01] Joe: It’s, it is 100%. That was a bad [00:46:02] Doug: analogy. [00:46:03] Joe: Yeah, sorry about that. Didn’t mean to pop the, pop the balloon, man. But a buffer ETF, OG, basically says, “We’re gonna protect part of your losses,” right? [00:46:13] Joe: “We’re gonna protect some of your losses. We’re gonna make it so you don’t have to follow the headlines.” That sounds like a good thing Or you can follow the headlines. I guess you can continue to watch all the headlines and get as angry as you want, but your portfolio is going to, uh, not have any waves anymore. [00:46:31] Joe: That sounds good. [00:46:33] OG: But? [00:46:35] Joe: But in exchange for upside. [00:46:39] OG: Well, d- I mean, there, but there’s a cost. There’s… You’re giving up upside return potential. I mean, here’s an interesting thing. I, I, I actually observed this the other day kinda personally. I was logging into Chase. Our, our mortgage is through Chase. I don’t generally log into the Chase website, but for whatever reason, I did. [00:46:58] OG: I had a great experience, and the experience was I remembered what our mortgage balance was the last time I had– Like, if some- if somebody would’ve asked me, “What’s your mortgage balance?” I had a number in my head. But then I logged in, and the number was way less, and that felt really good because I hadn’t looked in a long time. [00:47:15] OG: And so I got to experience the big change that happened. I didn’t experience it in, like, daily interest, you know, and principal reduction, which barely moves the needle, or even the monthly number, which does m- move the number but still not a meaningful amount. I got to experience it, like, a six-month number all at one time. [00:47:34] OG: And so the same thing is true with your investment portfolio on the upside. You know, if you just look at y- you know, your investment portfolio at the beginning of the year and make your rebalancing and be done with it, which statistically, by the way, is good enough. There’s no evidence to suggest that rebalancing more frequently than once per year provides any sort of economic benefit. [00:47:52] OG: So if you rebalance once a year, and that’s the day you look at it, there’s a really good chance that next year you’re gonna look and see a bigger number, especially if you’re contributing money to your portfolio. And so there’s a– Probably you’re gonna see a really big change year over year versus seeing, like, minute by minute, hour by hour, God forbid, you know, that level of, that level of frequency. [00:48:11] OG: So you’re seeing the impacts of the portfolio change or your financial plan change, if you’re talking about debt like I was earlier, over long periods of time, which by the way, is how you should evaluate it, and then you don’t live with the day-to-day fluctuation. This is solvable by just not putting any energy into this. [00:48:28] OG: You don’t even have to, like, get cute with it, and I mean, God forbid you buy stupid products, but, but you don’t even have to do that. You could just not log into your account. Just… You know some people, like, delete Instagram from their phone because they get too addicted to it? Like, just delete Schwab From your phone, and then you’re good. [00:48:48] OG: And then load it back in, log back in every year or every six months, you know? [00:48:53] Joe: Whatever your investment policy statement says, only do that. This piece actually isn’t a sales piece because they talk about dealing with it in different ways, but it is funny how people can, even some advisors can have this data, make a lot of great statements, and come to 100% the wrong conclusion. [00:49:13] Joe: Listen to this. Patrick Munlyn, Market Vice President at Forty Nine Financial, says, “A resilient client conversation in 2026 isn’t just about managing volatility, it’s about helping clients understand they have a plan.” Bam. Uh, we- this is exactly what you’re talking about, OG. They’ve anticipated the risks. [00:49:31] Joe: Bam. We’ve already factored in the fact that there’s gonna be some volatility along the way, and we already have looked at the, what’s called standard deviation of your portfolio. So we can be like the pilot. Last week I was on a plane, pilot said, “Hey, it’s gonna be choppy for the next 15 minutes.” Guess what happened? [00:49:47] Joe: It was choppy for the next 15 minutes, so nobody on the plane panicked. Had he not said that, there might have been more panic. So we kinda know the choppiness that we can expect a lot of the time And finally, their retirement income won’t require them to make emotionally driven decisions when markets get choppy. [00:50:06] Joe: That’s all great. And then he says, “What clients want most is confidence that if there’s a significant market pullback, the planning and framework we’ve accounted for this possibility. The planning and framework we’ve accounted for this possibility. Clients increasingly want to understand trade-offs, not just outcomes.” [00:50:25] Joe: I’m like, “Okay, where is this going?” Mudlin adds, “Structured investments have become an important tool in his planning conversations.” You’ve already solved it. Why the hell now are you leading people down this horrible road? Particularly for clients who are at a season of life where getting on ba- Listen to this sales discussion. [00:50:42] Joe: Getting on base matters more than hitting home runs. This isn’t about hitting home runs. Nothing to do with hitting home runs. [00:50:49] OG: All I can think about is the, um, you know, if you ever put anything into AI recently, they give you the, “It’s not this, it’s that.” That’s kind of like the new dead giveaway of- Yeah [00:50:59] OG: of AI, right? It’s, it’s, it’s [00:51:00] Doug: the new em dash. [00:51:01] OG: Yeah. Um, which by the way is kind of funny because I actually write with em dashes, and so now I have to like force myself- … to like figure something else out to do because like, oh, yeah, AI. It’s like, no, I’ve been doing this- For people not to think [00:51:13] Joe: you’re AI? [00:51:13] OG: Yeah. I have to like use semicolons and stuff like that now. The new, “It’s not this, it’s this,” the, the phrase that I see all the time is, “It’s a feature, not a bug,” right? That’s an AI, like it- they love that phrase, you know, for whatever reason. And volatility is not a bug. That’s the thing we have to have, and the more and more people that finally understand this, the better your life becomes because you can’t get market returns without market variability. [00:51:41] OG: It’s just, it’s an if-then statement in Excel. Like you have to have both, and anything that purports to say, “I’m going to give you this without this” is full of It just can’t simply exist, and, and it has to intuitively make sense to you that it can’t exist because if it did, everyone and all the money would do that. [00:52:03] OG: Like, there’s $800 billion that’s traded on the, on the public markets on a daily basis right now, right? If there was a thing that was better return with lower risk, do you not believe that some of those 800 billion, nay, all of that 800 billion, would find its way to that thing, right? Like, it just has to intuitively make sense to you that if this thing really existed and it was as good as, you know, this article from Investment News or this sales pitch from your broker sounded, all of the frigging money in the universe would go there because why wouldn’t it? [00:52:42] OG: So it doesn’t exist in real life. So there’s a give and take that has basically said, “This is no better than anything else. You’re giving up something to get this instead.” When you look at it in the context of your plan, most of the time giving up excess return is stupid. Don’t do that. Just, there’s a place for cash. [00:53:02] OG: You’re supposed to have cash, and you’re supposed to have safe, secure money. I d- I’m not disagreeing with that. But if this money is your investment money, if it’s your five-year money, seven-year money, 30-year money, this is the deal. This is the trade. [00:53:15] Joe: Yeah, these, these buffer ETFs over long periods of time have always lagged broad stock market index. [00:53:22] Joe: So if you’re long-term- And, [00:53:23] OG: and ever so, it must be thus. It has to. They, they can’t not do that because if they did, then all the money would go there. Would go there. Like, you’d see- 100% … you could see how, like, that all- [00:53:32] Joe: Yeah … [00:53:32] OG: just kind of works together. Yeah. It’s like over time this must be lower. [00:53:36] Joe: Well, so because of that, OG, they’re really timing dependent, right? [00:53:38] Joe: I mean, this gets back to timing and, and the fact that you can’t time the market. And so we have proven over and over again that we’re horrible at timing, which is why you say not to play that game, why you’re saying here, really, don’t play the timing game. Play the long range game. Stick to your plan. But it’s kind of, you know, if the timing is wrong, which it almost always is, it’s like buying insurance after the hurricane just went through. [00:54:02] Joe: Like, it, it doesn’t make any sense, and that- It’s [00:54:05] OG: not a feature. It’s a bug or whatever. [00:54:06] Joe: It’s a bug. Yeah, yeah. I, I will link to this piece in our show notes at stackingbenjamins.com and also have a discussion around it, I’m sure, in the, in Mom’s Basement, our Facebook group, stackingbenjamins.com/thebasement. [00:54:22] Joe: Speaking of that, let’s go to the back porch because, Doug, guess what I got today. [00:54:28] Doug: A hernia. [00:54:29] Joe: That and, and a letter [00:54:36] letters: We just got a letter, we just got a letter, we just got a letter. Wonder who it’s from. [00:54:44] Joe: I got a note, guys, from Kathy. Kathy says she was listening to the podcast about Gen X would rather die than run out of money. [00:54:51] Joe: This was episode 1840 a couple weeks ago. You guys remember that? The title of the episode’s Why 67% of Americans Fear Running Out of Money More Than Dying. [00:55:00] Doug: Yep. [00:55:00] Joe: She says, “Somebody was talking about Roth IRAs and when they started in 1998. I remember my dad making me open one up. Okay, not made me, but said it was the thing to do.” [00:55:11] Joe: I like how Dad, Dad makes it the cool thing. “Hey, all the cool kids are doing it.” [00:55:18] Doug: Oh, and low-rise jeans. But Roths, way cooler. Like, I would do that first, and then maybe… [00:55:24] Joe: Of, of the two? 100%. Yeah. “I was 31 years old, special education teacher, and trying hard to pay myself first and do as much as I could to not have to work for anybody down the line. [00:55:34] Joe: Coming from a family that said free time was better than working for yourself, the only way out I saw was to save.” Well, a family that, uh, guys, that’s anti-entrepreneurship. I would rather a free time than work for myself. That actually is a good way to look at it though, OG, because I think the entrepreneurial myth is that entrepreneurs have it easier because you have, quote, flexible time. [00:55:57] Joe: So you, I’m sure in your practice, OG, you barely work. [00:56:01] OG: Well, I mean, the reality is, and Joe, you know this, and maybe this is the well-kept secret, you know, entrepreneurs only work really half-time on a daily basis. We just have the flexibility to pick which 12 hours a day we wanna work. So, um, that’s the, uh- [00:56:16] Joe: Yes [00:56:17] OG: that’s the myth that everybody, you know, that’s, that’s the reality is, like, you know, we on- we do only work half-time, you know? So. [00:56:23] Joe: What’s the other one? An entrepreneur works for himself ’cause they’d rather work 60 hours for themselves than 40 hours for you. Yeah. [00:56:29] OG: Fair. [00:56:31] Joe: She continues, “I opened the Roth IRA in 1998, maxed it out every year until 2024 when I stopped working. [00:56:37] Joe: Today, that Roth IRA account is worth $511,000 and is one piece of my retirement. I was a pro- teacher, college professor, online adjunct professor. I saved my ass off. I never relied on a pension. I worked in the public school system, and I worked long enough in a state to get vested. When I moved, I rolled over my money into a rollover IRA worth over a million, and I saved all I could, paid off my home, had a couple rental properties over the years. [00:57:02] Joe: Yep, I had a good life, had no student loans, and never went into debt, with the exception of a home mortgage. I quit full-time work at 55 and all paid work two years ago. Short story long, not all Gen X suck at DIY retirement. ” Absolutely love that, and I think, OG, that reflects a lot of our stackers, that while Gen X has trouble saving, as the piece says, man, we’ve got some people doing some great stuff out there. [00:57:30] OG: Oh, 100%, yeah. I mean, every generation has… I was just reading a book review that I can’t wait to get my hands on. I’ve got, like, a no-spend May going on right now, so I’m just- June 1st is gonna be lit on the Amex card, by the way, because I’m, I’m building a big shopping cart of, like, all the stuff I’m gonna buy. [00:57:48] OG: But I’m trying not to buy anything in May just to experiment. [00:57:51] Joe: Turn over a new leaf. [00:57:52] Doug: Yeah, and what you’re not telling people is that your little caveat is, well, like, no spend for you means trying not to have six-figure spending. Like, five-figure spending is the equivalent of no spending, isn’t it? [00:58:03] OG: No, I really have not bought… [00:58:04] OG: I mean, we’re buying groceries and stuff, but I really have not done any sort of discretionary purchase of any kind this month so far, and we’re already… Today’s already the 11th, guys. Like, I am a third of the way through it. Do not kill my vibe, Doug. I’m very proud of myself. [00:58:20] Doug: I can’t wait to hold you to this. [00:58:21] OG: But I was reading this book review, and it was talking about, like, income and asset growth generationally, and, you know, how things have been, and the stories that people are told. You know, like how last, you know, the other generation had it so much easier, and all of that sort of stuff. He references a, a series of content that was in the mid-’80s, early ’80s, that was like, “Well, Boomers are screwed. [00:58:41] OG: They will never be able to retire. They’re never gonna have enough money. The old way of doing things is over. Best wishes, you’ll never make it.” And, uh, of course, you know, they’re doing okay, generally speaking, but there’s a subset, right? There’s a subset of people that aren’t doing okay, that had some influence on their own outcomes. [00:58:57] OG: So sounds like Kathy has done all the right stuff and keeps on doing all the right stuff, so that’s pretty frigging awesome, in my [00:59:03] Joe: book. Well, and for our younger stackers too, this idea of starting early, you know? [00:59:07] Doug: Yeah. [00:59:07] OG: Yeah. [00:59:09] Doug: OG just gave, gave me an idea. We should have our research team, in the back room over there, we should have our research team go back and look at some publications from the, say, ’90s, and just see how many of those predictions have come true and/or how many of the trials and tribulations are the same as they are now. [00:59:30] Doug: ‘Cause there’s so much clickbait stuff that is out there making it feel like, “Oh, it’s different now.” And I’d like to see what that’s really like over the last 30, 40 years. [00:59:40] OG: I, uh, Doug, I do have some content on that I’d be… Maybe, maybe one day we can share it. Yeah. [00:59:45] Doug: Yeah. [00:59:46] OG: Some piled up stuff that I have accumulated over the years. [00:59:49] Joe: Kathy, thanks for the awesome note, and, uh, great to hear from a stacker doing very, very, very well. Big thanks to all of you for listening. If you’ve got somebody who watches the news far, far, far too often, Simone Stolzoff’s interview today really, I think, is something you’re gonna wanna pass on to that, uh, future stacker. [01:00:08] Joe: Turn somebody who is very worried into somebody that can start stacking and begin with the end in mind. But we always end with the end of the show in mind by asking Doug, “What should we have learned on today’s episode?” [01:00:22] Doug: Well, Joe, first, take some advice from Simone Stolzoff. Change is the only constant. [01:00:27] Doug: Dealing with uncertainty begins with realizing there will always be a cloud over what comes next. Second, dealing with uncertainty by giving up risk in your portfolio, only make that move if you’re certain you have enough money without growth. But the big lesson, don’t ask Joe’s mom to play poker. How does she always have the other five aces that OG isn’t holding? [01:00:52] Doug: There’s no way this family is that lucky. Thanks to Simone Stolzoff for joining us today. You’ll find Simone’s book on the topic, How to Not Know: The Value of Uncertainty in a World That Demands Answers, wherever books are sold. We’ll also include links in our show notes at stackingbenjamins.com. This show is the property of SP Podcast LLC, copyright 2026, and is created by Joe Saul-Sehy. [01:01:19] Doug: You’ll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. [01:01:39] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at the Stacking Benjamins show.
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