Ben Miller (ChroniFI) Stoicism, Time is Money, Risk, & Imposter Syndrome | Military Money Manual Podcast Episode 65

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Ben Miller from ChroniFI joins Spencer Reese and Jamie to talk about Stoic philosophy, learning humility on Wall Street, imposter syndrome, and how everything is risk.

Learn more about ChroniFI at and Ben Miller's writing at

Outline of Episode:

  • How Ben went from a career on Wall Street to ChroniFI
  • Facing Imposter Syndrome
  • Personal Finance and Credit Card Use
  • Purpose and fulfillment before reaching FI
  • Ben’s lessons learned from Wall Street
  • How to deal with discouragement in a down market
  • Stoic philosophy and investing 
  • Why pursue FI?
  • Lessons learned from Four Thousand Weeks 
  • Information about ChroniFI and who would be the ideal ChroniFI user

Military Money Manual Podcast Episode 65 Transcript

[00:00:00] Ben: Essentially, the equation that I was solving here was how can I get financial independence as quickly as possible, and then happiness eventually, and I realized that was exactly backward. I realized that what I should have been doing was pursuing happiness as soon as possible, so long as I was financially independent eventually. 

[00:00:43] Spencer: Hey, podcast listeners. Welcome to the Military Money Manual Podcast. I'm Spencer Reese, founder of and author of The Military Money Manual book. Today my co-host Jamie and I are talking with Ben Miller. Ben Miller is the founder of ChronifFI. It is a specialized budgeting and forecasting tool that allows you to visualize your financial independence journey, not just in money, but also in terms of time.

It's a really interesting concept. I recommend you go to and check that out. He's also got a podcast available anywhere you can find podcasts with the same name. ChroniFI. We had a really good discussion with Ben Miller. We got into all kinds of different topics. He's really well-read and well-researched on the ideas behind financial independence.

Some of the ideas we talk about today are how time is money, and money is time. Money can buy you time, but it goes way beyond that. We also talked about imposter syndrome and how it doesn't matter what job you do, whether it's in the military, or outside the military, imposter syndrome is real and a lot of people suffer from it.

And Ben talks about his experience with imposter syndrome and learning humility while he worked on Wall Street. We also talk about how stoic philosophy can help you become financially independent. Hey, if you find this episode valuable, the easiest way you can say thank you to me and Jamie is by leaving us a five-star review on Spotify, apple, or wherever you listen.

That helps spread the word and helps us beat the algorithm and get to the top when anybody searches military. Without further ado, here's our conversation with me, Jamie, and Ben Miller from ChroniFI. 

Ben, thank you so much for coming on the podcast.

[00:02:29] Ben: Thanks a lot for having me, and I'm excited to be here.

[00:02:31] Spencer: Can you go over a little bit about your background and how you got started with your interest in personal finance?

[00:02:36] Ben: Yeah. My interest in personal finance began, I suppose when I was young. We weren't hard up for money or anything like that, but my dad was a very frugal guy, and starting when I was like six, I remember I asked for an allowance and he decided that the best program would be one where he didn't give me money, but instead I gave him five dollars. Then each day he would give me a quarter, and that was it served double duty for him because he was traveling a lot and doing all that. So one, I got to learn about compound interest because as a six, seven year old getting to a point where I was like, “Hey dad, can I give you another $5?”

That was a milestone moment. I woke up with what wound up being a little stack of quarters on my desk every day when I got out of bed, and I know that my dad had been there. Anyways,  I don't know if you're looking to go that far back, but that's how I initially got interested in personal finance.

And then later on it was really just a matter of getting out of college into the real world and seeing that oh, okay, there's a whole lot of extra adulting I have to do here. I should probably do like I do with the rest of my life and just make it as efficient as it can be. 

[00:03:41] Jamie: You used to work on Wall Street, right?

What did you do on Wall Street and what brought you to the point where you left and then started your own company?

[00:03:47] Ben: Yeah, so I was at Goldman for eight years trading, foreign exchange derivatives. So yeah, Wall Street was a lot of stress, a high-pressure situation, and all of that incredibly intellectually stimulating, working with a ton of smart people.

And all that, but ultimately I decided that it wasn't what I wanted the entirety of my career to be about. So eventually I started thinking I wanted to do something entrepreneurial, but I didn't have my big idea yet. As I started merging the two threads of seeing oh, personal finance really is a passion of mine.

I'm spending a bunch of time on the weekends learning about this stuff, et cetera, and then realizing, Hey, there, there might be a way to weave these two things together. I could do a business about personal finance and thereby take a little bit more control over my life. Frankly, also the personal side of my life was colliding with it in a big way.

I had a two-year-old that was telling me her favorite thing to do is to walk on grass. So I was like, oh geez, we have to get this girl some grass to walk on. I was working in Manhattan, living in Jersey City and a kind of concrete jungle, so it was time to pull the rip cord.

[00:04:53] Jamie: And so tell us about the company that you started and then I'll have a follow-up for that as, well.

[00:04:57] Ben: Yeah, the company I started is called ChroniFI.

Basically, what we do, we help people simplify their finances by understanding them in terms of time. So instead of just looking at the nuts and bolts, here's your net worth, here are your taxes, here are your expenses, all that type of stuff we find that it's just way easier for people to understand these things if you boil them all down.

And so you can see them in the context of one another. So for example, when you look at things in terms of time, you can see, okay, given all this net worth, all these expenses, et cetera, these are abstract things. But when you boil them together, what pops out happens to be, here's the number of years that you can afford to be financially independent right now.

And so for me, when I looked at that number, When I was at Goldman and deciding when I should get out, I thought that it was going to be more than a decade before money was a problem. So I was like, why do I feel so fragile? Why am I feeling so insecure about my ability to go and do work that I really want to be doing?

And so that was a big turning point for me. Once I built the precursor of this system for myself and saw that it worked and saw that it changed my life, I was like, oh, geez. The way that software works, you can just control C, control V, and have everybody else have access to it, too.

[00:06:08] Jamie: That's really neat and I think it's a refreshing approach to think about your money in terms of time and time savings. We talk a lot on our podcast as well, and I know I've seen your blog posts talk about exchanging your time for money. So it seems like you had set yourself financially in a way on Wall Street and you had enough money to give yourself options to go after this passion project that you had. So the other side of that might be, in the same blog post, is $10 too much for a sandwich? It depends on your situation and what you value. So how do people use that equation to spend in alignment with their priorities versus thou shalt do this way or that way?

[00:06:48] Ben: Yeah, I love that question because trade-offs are different for everybody. Different strokes for different folks. The idea here is not if you realize that your Chipotle habit is delaying your retirement by three months, that doesn't mean never go get Chipotle. What it means is, here's the trade-off.

Make your own informed decision. So for me, it came sequentially as this realization. I had this job that I wasn't in love with, and so I was like, okay, how do I save more money? How do I get out here quicker? So I had this assumption that expenses were always everywhere, a thing that you wanted to minimize, but what I was missing there was this second point, this one, two.

The second punch of the combination, if you will, is this idea that, okay, yes, you want to trim the fat. You want to get rid of those expenses that are not conducive to your long-term health and well-being, but it's just as important to be willing and in fact intentional about spending money on the things that do contribute to your long-term health and well-being or that of your loved ones.

Because that's what money's for. So it's not about gutting everything. It's about making sure do does this hierarchy of my spending, does it make sense relative to my values? And if it does, great, keep investing in that. If it doesn't, here are some tweaks you can make.

[00:08:01] Jamie: Another one of your blog posts that I really enjoyed.

By the way, that's, right? If people want to see all your posts and subscribe to the newsletter there. But another one I really enjoyed was the one where you talk about imposter syndrome and reallocating at least a part of your energy away from intellectual progress towards intellectual reputation.

I think a lot of times military service members can relate to that. Then you go on to talk about how FI is not a sprint and you have to keep the engine running sustainably more importantly than to make it run faster.

[00:08:30] Ben: Yeah, there's a lot in there, on imposter syndrome. I think a lot of people, particularly of our generation really struggle with that.

For me, the way that I experienced that was just in terms of questions, and it's like when I started out on my job on Wall Street, I was asking all these questions and I had a boss who was like saying, “Hey man you're asking way better questions and people two years older than you, nice job.”

And I was patting myself on the back and whatnot. Then I realized two, or three years later, I wasn't asking those questions anymore. It wasn't that I was this genius asking these precocious questions. It was the fact that everybody in that type of a system has a tendency to get more complacent with just, oh, this is the way it's always been done.

That sort of thinking.

[00:09:10] Jamie: We don't know anything about that in the military. 

[00:09:13] Ben: Yeah, I was going to say, I'm probably preaching to the choir. When you have a larger organization, that's just in some sense the way it has to be sometimes. So finding your place where you can actually, ask questions and continue to grow and develop into a better version of what you're up to, I think is a huge deal.

And Leaving a bank and entering the entrepreneurship ring is if you don't have imposter syndrome when you jump into entrepreneurship, then you're probably not paying enough attention because the idea here is there's an infinite variety of things that you need to know. There are all these plates, you have to keep spinning at the same time.

And if one of them drops, hey, the whole thing fails utterly and so good luck. But this side of things, it's just an approach of humility going listen, there's this whole world of information that I need to know. I'm only going to have a chance to know, like some low single digits, percentage of it, and I'm going to have to do the best that I can with what I've got.

And so anyways, it's a topic that hits close to heart.

[00:10:10] Spencer: One thing that I found in the military was, Early in my career, I was afraid to ask questions because it seemed like I hadn't studied the material enough, or at least to me, right? But that was the time to ask questions. When you're newly enlisted or you're a young lieutenant, that's your time to ask all the silly questions, because people expect it. If you try to act like you know everything and people aren't going to be as helpful to you.

And so what I realized, It was really only when I became a more senior captain and major O-4 that I actually became comfortable enough in my own skin and recognized that. In my career field in aviation, there are a million things you need to know. There's no way that you can know everything. Just recognize that, and as you said, be humble and ask the questions.

And so I would ask the dumbest questions as I got more senior. Yeah, I didn't care anymore. I didn't care what my reputation was. I think a lot of that though was I had built up this reputation as a better-than-average pilot in the squadron. But then at that point, you can be humble and you can say, look, I don't know everything.

If you know something, I need to know what you know so that I can learn from your experience.

[00:11:21] Ben: Yeah. That totally resonates. The thing is, it's like when you just start out, it's like this window is never going to be wider than that. Oh, it's acceptable to ask any question. Cause that's your job when you're green is to really just ask as many questions as you can to come up the learning curve.

And then the reality is for those of us who wind up hesitating and it's like that question that you were afraid to ask for looking stupid in year one, guess what? If you don't ask, you're still going to have that question in year three. How stupid are you going to look then when you still don't know that thing that's just basic, but you're totally right. Having that confidence comes later. So it's like there's this U-shaped curve sort of situation going.

[00:12:00] Spencer: Yeah, it reminds me of the “afraid to ask meme” Andy from Community where he's like, “I never asked this question during year one and now I'm like a senior director and it's too late.”

I can't ask it anymore. But it also reminds me of something you said earlier, imposter syndrome, where what I found was the higher I moved up the organization, even in the military. Everybody has imposter syndrome and everybody is just trying to figure it out. One thing that the military is really good about, and maybe some other organizations do this as well, is as soon as you figure out your job and get comfortable in it, they promote you to the next one.

That always frustrated me because I was like, no, I finally figured out how to do this job. Now you're going to put me in another job and now I'm going to have to go and figure that out and I'm going to have to keep overcoming imposter syndrome along the way.

[00:12:48] Jamie: I think imposter syndrome shows up definitely in work, and I've definitely experienced that as well in the office.

But if we talk about personal finance, we've mentioned in previous episodes how people don't like to talk about money. Even though in the military, our pay charts are published, everyone knows they're set by Congress. Everyone knows exactly what we make. You can look up our housing allowance, our food allowance, our base pay, and how much extra pilots get.

All those things are out there in the open, but it still is a taboo topic. So I think a lot of times people have imposter syndrome in their personal finance journey as well.

[00:13:16] Ben: And that winds up hurting exactly the people who can't afford to be hurt in the sense that who winds up talking about this stuff with each other?

It's often people who are similar to one another. So if you get to know somebody, I know what you're talking about it almost feels like you're talking about your sex life. Like it's just finance is just held so close to the vest. It's positively damaging to folks because the type of people that you're associating with and close enough to really, open the kimono, so to speak on this topic.

There are oftentimes people who don't know necessarily much different than you do. What I think would be really beneficial for folks is if they were a lot more willing to be transparent with all types because that's how you get the osmosis of information to flow down from people who have more of it.

By the way, our schools don't teach us to those who don't have any of it. We've seen some states and some jurisdictions start to mandate some personal finance education. But I don't know about you guys for me, four years of college and eight years in finance. I didn't learn anything about personal finance from either one of those places.

I had to pick it up from books and blogs and stuff like that. So what chance does anybody else have?

[00:14:22] Spencer: Yeah, and I think that's one aspect of our education system where I don't think this is just America. I think this is global where you learn how to derive an equation and you learn how to combine chemicals on a chalkboard.

But, you don't learn how you know to pay off a credit card. I remember when I got my first credit card, I thought that the interest was immediately charged like you bought something, and then it started accruing 26% interest immediately. So of course why would I ever get a credit card?

It's insane. It wasn't until after hours of research that I realized, oh no, you pay for something. Then you get a statement and then 28 days after that, then you owe the money. So if you bought something on day one, you basically get an interest-free loan for 60 days as long as you make the payment after 60 days.

Just that little factoid to my younger self was mind-blowing. I was like, why is nobody ever, Dave Ramsey was a popular figure in my financial upbringing, and so credit cards were looked at as a source of evil. It was never explained to me that no, it's a tool, it's a hammer and if you hold the hammer the wrong way, if you swing it the wrong way, you can get hurt.

But if you hold the right way and you use it correctly, it can be a great tool to improve your financial situation. It's just that a lot of people tend to use hammers the wrong way, I guess when it comes to credit cards.

[00:15:49] Ben: Yeah, totally. It's one of those, Batman things where it's like, with great power comes great responsibility that's the nature of the beast. I remember when I was growing up, my parents told me that I had to get a credit card last year of high school, that type of thing, and I looked at them like they had three eyes because it was just like, why would I get a credit card? My system's working, I was cutting the neighbor's grass and babysitting and stuff like that, and so I was like, okay, my system was my nightstand right by my bed had this drawer, and I would put my cash in there and once it got above a couple of hundred dollars, I'd go to the bank.

Okay. It only ever went one way. Like why introduce credit into this? It's working perfectly. Then, they started educating me. They started going you need to build up your credit so that when it comes time you can borrow more money and blah, blah, blah, blah, blah. But all this stuff is counterintuitive in a lot of cases.

And so people do wind up getting in over their heads with that. But you're totally right. You're leaving a, leaving aside the part that you get 2% back on everything you buy if you do it with credit that you can't get with cash. So it's an interest-free loan and a 2% discount. It's almost foolish if you don’t. For some people. 

The thing is, not all people are wired the same way. That's one of the things that I had to train out of myself as I left Wall Street was I had this mentality of, okay, I need to make the most basis points of return that I can possibly make on everything.

Otherwise, I'm doing the wrong thing by my family because I'm not being a good steward of my resources or whatever. Then I realized, okay. I'm human. I'm not a robot. So it's not just about inserting the right code and then just executing it. It's about appreciating the fact that look, people are people.

They need to be able to be motivated. They need to make decisions that sometimes aren't going to be optimal, but they're going to be better than what they were doing otherwise. Sometimes going cold turkey is the right way to go. Even if the right amount of credit card use for most people is some and possibly quite a bit.

For some people, if you're personally predisposed towards irresponsible spending, sometimes the right thing is to cut them up and move on because 2% isn't worth the risk.

[00:17:45] Spencer: A lot of the ideas that you've encapsulated in ChroniFI, remind me of the book, Your Money Or Your Life. Are you familiar, have you read that book?

[00:17:54] Ben: Yes. It's deeply enmeshed within the origin story but go on.

[00:17:58] Spencer: Yeah, so the whole idea is we're trading our time and energy for money, and eventually if you save a portion of that money and you set it aside and you invest it properly, then the investment can outgrow your contribution of time and energy.

And then you can free yourself from trading your time and energy for money. Then your money just provides you with enough income to live your life. So you said that was instrumental in the origin story of ChroniFI.

[00:18:26] Ben: Oh, absolutely. I started smirking as soon as you, as soon as you mentioned the book because literally what happened in my case was I heard as I do with a lot of the books that I read I heard about it one place and I was like, yeah, okay, maybe. Then I heard about another place and I was like, okay, I'll check this out. So when I read that book, and it was a few years into my career, it was just a total mind blow for me.

I was I realized I'd been thinking about money the wrong way, forever. What I was trying to do was just save up a giant pile of money and then live off the interest. What I didn't realize was that no, dude the point here is to structure a life where you're going to be financially independent at some point, but enjoy it along the way.

I literally remember not long after I read that book, I was in the gym at Goldman working out and I was like, there's have to be something out there about this. So I was googling Your Money or Your Life app and there was nothing. So that was where kind of the seed of ChroniFI was planted in my head. Okay, then I guess first I'm going to have to develop some more skills and think about how I'm going to start a company around this.

But that was what kind of got the ball rolling.

[00:19:34] Spencer: Wow. I love that. So one of the concepts that you just talked about there was, I read this quote on Reddit once where the guy said, “You want to build the life you want and then save for it.” And in my mind that was life-changing when I read that, which is not, it's not a quote I use for Reddit quotes all the time, but I was laser-focused on achieving FI in my younger days.

It was in that boring middle, which people will talk about. You get very excited when you first learn about FI, financial independence, retiring early. You get very excited about it, and you start saving and you cut your expenses and you increase your income. Then you were like, oh my God, I have to do this for 10 years in order to actually achieve FI.

What do I do in the middle? So I was in that boring middle, and I was still focused on saving and increasing my income. Then I read that quote, build the life you want and then save for it. I realized this could be it. What if I get to 10 years from now, I finally achieved FI? And I get hit by a bus and I die.

And I look back over that 10-year period and I scrimped and I saved, and I was miserable to achieve this goal, to get to this finish line. Then I realize, oh no, like it wasn't worth it. The journey was miserable along the way. So can you talk a little bit about purpose and fulfillment before achieving fi before retirement?

[00:20:57] Ben: Yeah. There's a ton in there. So stop me if I run over on this question because holy cow. There’s a ton to say. First of all your whole idea there of what if I get hit by that bus, 10 years from now? That's exactly it. Tomorrow's not promised to anybody. So if you are basically not liking your job, and so because of that, you want to save up your money at an accelerated pace and so you've got your expenses and make yourself unhappy at home, guess what?

Unhappy at your job plus unhappy at home equals unhappy. That's not exactly a recipe for you building the life that you actually want. It matches my own epiphany in the sense that I had that same complex. I was just trying to like sprint to the finish line. Essentially, the equation that I was solving here was how can I get financial independence as quickly as possible, and then happiness eventually.

And I realized that was exactly backward. I realized that what I should have been doing was pursuing happiness as soon as possible, so long as I was financially independent eventually. So I love that quote that you mentioned from Reddit because that's exactly the whole point. It's not about getting to some mythical land where all of a sudden money's growing on trees and you never have to worry about anything.

Spoiler alert, you're going to be the same person when you get there. At least in a lot of respects. So getting to a point where you can be comfortable enough to pull the first fruits of retirement forward and start living a sustainable life now that gets you to where you want to be eventually.

That was the whole entire ballgame for me. When I realized that, I was like, okay. It turned by individual situation from why should I leave into why should I? 

[00:22:41] Spencer: I love that. It reminds me of the quote, “No matter where you go, there you are.” 

Let's say you set off on this journey to FI and you increase your income and you decrease your expenses and you're studying all the Mr. Money mustaches, and you eventually, you get to the finish line, you've got 2 million in the bank. You look around and you're like, okay, now what? And you realize if you didn't become a person along the way, if you didn't develop hobbies and relationships and create a life worth living, you're going to get to the end of it and you're going to be miserable.

The one thing that money does is reveal your true character, right? If you are an a-hole when you're poor, you're going to be an a-hole when you're rich, and if you work on becoming a better person. As you become more wealthy, I think that the money will just accelerate that journey towards becoming a better person and towards living a better life.

[00:23:37] Ben: A hundred percent. I love that you mentioned Mr. Money Mustache there as well because he was like my gateway drug into this whole space of like personal finance. So one of the concepts of his that comes to mind, or at least I first heard it from him, who knows, maybe he picked it up from somewhere else, is this idea of the weekend test.

It's this idea that if you're trying to imagine how much you're going to enjoy retirement, a great litmus test is how much you're enjoying your weekends. Because really all retirement is in the end, is just expanding your weekend from two days a week to seven days a week. So if you're not really loving your weekends right now, where's the evidence that you're actually going to enjoy just kicking it forever?

And that matches my own experience as well, because going into the workforce, I was like yeah, clearly what we want to do here is we want to retire as soon as possible so then we can do whatever we want. What I realized was like, okay, dude, one, I'm not going to be able to stomach showing up on the trading floor for decades that it's going to take to get me where I want to be.

Goldman took my hair from me. What else is it going to take? That's, that was a part of the reality for me. Then, the other half of it was like even at a job that was great, but I just wasn't in love with it. A week and a half into vacation, I'm itching to get back to work. So what's up with that?

Whether it's a feature or a bug. I enjoy productive labor of some kind. So instead of solving for never making a dime again, factor in the fact that I'm going to want to, as a part of my optimal life building, do some sort of production, some sort of work, and solve around that. Money can come as a byproduct.

[00:25:15] Spencer: I found the same thing. I took a six-month sabbatical after I left the military and after three months I was miserable. I thought I had, I did a lot of things all at the same time, so I left the military. I moved countries. I moved away from family and friends. I quit my job. And I thought I had enough hobbies and enough activities and enough things to fill the time and to provide a fulfilling life, and I didn't, and I got to the point where I wasn't happy and I needed to make a change, but I honestly, I don't know if I could have set myself up for success until I actually took the six-month sabbatical.

And gave myself all that time to figure out what do I want to do, and who do I want to be when I grow up? And It's funny because I'm watching my dad who listens to the podcast. Hey dad! And he's approaching retirement and he's going through a more traditional retirement age of 62. He is going through the same thing where he's I don't know what I want to do next.

I enjoy working a little bit, it helps my mind work and provides some intellectual stimulation. So that might be part one. One quote that he said is, “I'm retired, but I'm choosing to work.” My mom just laughs at that. But I get it. I understand. Warren Buffet, 80, almost 90 years old, multi-billionaire.

And what does he do with his time? He likes to work, and he loves to figure out good trades and good companies to invest in.

[00:26:48] Ben: Yeah, and I always used to be jealous of the folks who really enjoyed trading because it's an incredibly remunerative career, and I was just one of those people where I was like fun and intellectually stimulating and whatnot, but I just didn't have the innate hunger for it that made me go, oh yeah, I want to wake up and do this even if I'm not paid for it.

And so being in that spot where it's like the people who do enjoy that. No knock on them. They won the game. If you can find something that pays the bills and you actually enjoy doing it, that's the entire point. All of this retirement business or all of this, whatever labeling you want to apply to it, the whole point is just being able to wake up and enjoy your day.

And so if you're doing that and you're making ends meet, game over, you win.

[00:27:35] Spencer: Yeah. It reminds me of the Psychology of Money where he says, “The highest dividend money can pay is choosing what you do with your time, who you do it with, how long you do it.” That's why we save and invest, right? So that eventually if you can go and find a thing that you enjoy trading your time and energy for, and for most people it's usually not the job that they're currently doing.

There probably is some kind of productive work or some kind of hobby out there that a lot of people would enjoy. 

So you mentioned working on Wall Street earlier. What were some of the lessons that you took away from, working with some extremely type-A motivated people who were in an industry where you could potentially make a lot of money?

[00:28:16] Ben: I'm going to say something that's probably counterintuitive at first blush, and that is that Wall Street taught me humility. People think Wall Street, they don't necessarily think, oh yeah, this person's going to be afraid of his own shadow. Humble, self-effacing sort of guy. You think of this Gordon Gecko. Yeah. Gordon Gecko, alpha Male, that type of thing. The idea here, why I'd say that Wall Street taught me humility is the fact that when I was growing up, I was a pretty psychologically conservative sort of person. I believe this, I'm always going to believe this. That's the way the world works and I already know everything.

You know I was 18 and I was pretty sure I knew how the world worked. What I realized going onto Wall Street was, okay, no, I am killing it if I'm wrong 40% of the time. If you can be right 60% of the time and wrong all the whole rest of the time, if you've got the same size of bets and all that kind of stuff, then you are an absolute master.

And so realizing that, okay, I'm going to be wrong a giant proportion of the time. When I'm wrong, I have to get back up, dust myself off, and keep at it. You learn the same thing in martial arts. You learn the same thing I'm sure in lots of applications within the military, it's like mistakes are the rule, not the exception.

And so it's all about getting the reps in, getting those reps in, seeing how you failed, doing better the next time, et cetera. So I feel like in a large way I aged in dog years when I was on Wall Street because I just had to make so many decisions every day that it's like you get to a point and you're like, who am I to say that at 30 or whatever I was when I resigned?

Who am I to say that I'm mature or that type of thing? But I feel like at least in that one dimension, I just got so many more reps at making decisions and being wrong that I got to a point where it's okay, I'm no longer afraid of being wrong. When you're no longer afraid of being wrong, it's just like the floodgates have been unleashed because you're able to go out there and swing for the fences a bit more.

Whereas a lot of people who come up in these sort of go to a good school, you go into a respected institution, blah, blah, blah, blah. Then if you've never made a mistake, if you've never been visibly wrong, then you're just terrified of it. We see a lot of our best talent within society kind of occupy that perch where it's just they've never made a mistake and they don't plan on doing it any time soon.

And that can be a real hindrance.

[00:30:38] Spencer: What were your peers' and boss's reactions to leaving Wall Street?

[00:30:42] Ben: Oh, it's funny you asked. I was about to pop into this just a moment ago. Essentially, again, you think of Wall Street as this cowboy risk-taker culture sort of situation, and in some ways it is, but in another respect, it's incredibly risk-averse people because a lot of these people are people who graduated top of their class, went to Harvard and then wound up at JP Morgan Chase or something like that, and it's just it's been one accolade after.

And they get into that sort of framework that I was mentioning before where it's just okay, this person's never had something go wrong for them. So how can they possibly expect to know how the world works? Because that's the way the world works. It goes wrong half the time and it goes right the other half. 

So I was shocked because it's all relative. For example, I asked my friend the other day, if you were to place me on a spectrum, where zero is afraid of his own shadow, like risk-averse, and 10 is like crazy cowboy risk-taker, where would you put me? And he told me a couple of ticks to the right of zero.

So that was one data point. The reason why I asked him that was because I was talking to somebody who I used to work with just that past weekend and this guy was telling me, I just don't get it, man. How on earth did you leave? What about this? What about health insurance? What about that? What about all these other things?

It didn't really hit me until right that moment that wow, a lot of people within this sort of orbit that is of, high finance or that type of thing, regardless of what they're doing at work in their personal lives, they're incredibly risk averse because it's always, did you think about this?

What about that I that you forgot to dot, that T that you forgot to cross? There are all these different things, and the reality is life is uncertain. Those of us who are in careers where we're forced to confront that every single day, understand that fact. How could you possibly leave the house?

Don't you know that you could get hit by a car? Like everything is a risk. You guys in the military, again, preaching to the choir here, like everything is a risk. It's just about taking the right calculated risks. So for me, I got to a threshold where I was just like, this is silly. Why am I feeling financially fragile?

And for some people that threshold is way higher. I like to think that what I'm doing with ChroniFI is putting things into a framework where people can look at things objectively and go, okay, here's what it all means, this complex finance thing, oh, here's what it all means. At the end of the day, I think one of the best ways to do that is here's how many years I can afford to coast off of what I've got.

Spoiler alert, yeah, that's responsive to your net worth, but it's also way more responsive to your expenses. So if you get your lifestyle into shape the right way, you can make yourself pretty, well, we'll put it this way, about as immune as you can be from whatever the world's going to throw at you.

Because if you've got, 5, 10, 20 years in the bank, then for most folks, that's F U money. If I'm thinking about things and going geez, my kids are going to be in college by the time that money's an actual problem, that's okay it's time to get out there and take a risk.

[00:33:45] Jamie: Okay, Ben, so speaking of things, the world is going to throw at us SB 500 s down over 20% year to date.

So someone logs in to their ChroniFI portal and sees their net worth has dropped, or their time to FI has increased. What advice do you have for someone who is a little discouraged about their financial outlook or investing in today's market?

[00:34:04] Ben: Yeah, I think that's an awesome question in the sense that we have a problem as humans, and that is, pains hurt us a lot more than pleasures help us.

 The way that we're wired, I forget what the ratio is. I think it might be either four or seven to one or something like that. Whereas winning $20 feels just a fraction as strong as losing $20 feels bad. So the idea here is that when you look at it from that behavioral finance perspective, It is exhausting to look at the markets.

There's a book that I read back in the day, Fooled by Randomness, by Nassim Nicholas Taleb, and his supposition that he put forward in that book was this idea that, okay, if you look at the markets every single day and you put that together with this idea of what I just mentioned, which is this behavioral finance point, then all of a sudden you're just going to be a miserable wreck, even if your portfolios are going to the moon because half the time it's up half the time it's down, et cetera.

If each one of those pleasures is offset by a pain of the same objective size, but much huger psychological size, you're just going to be in bad shape. So anyways, why I even went down that rabbit hole is because I think it's incredibly important to take the stoic approach, divide the world into what you can control and what you cannot control, and focus on what you can control.

And so what do I mean by that? Within ChroniFI, that's exactly the approach that we take is this idea that, okay, yeah, sure, over the last month you got six months closer to retirement. But more importantly, where's that coming from? It's way more useful to know that, hey, four of those months were, because I was a diligent saver because I embraced better habits and stuff like that.

Whereas two of those months are from the market. I can't predict that's always going to happen. So I'll just wave it off to the side. There's this paradoxical nature of progress within personal finance, which comes from the fact that as soon as you start to get closer to where you're going, the world starts to seem like a much less controllable place because when you have money invested in the markets and stuff, then all of a sudden it's you skimp and save and you pack your own lunch to work instead of getting a fancy sandwich at the office or whatever, and you save 200 bucks over the course of a month. That feels good, but if you've already got a portfolio, then your portfolio is up or down ten grand in that same time.

So it's like, why did I do this to myself? And it doesn't matter whether it's up or down, it's just the fact that it's outside your control. So the reality is when you bake it all together, do the math and understand what this actually means within the context of your life. That $200 a month is $2,400 a year, and that $2,400 a year equals $60,000 that you would have to have invested to endow that habit for life.

And so suddenly it's not 200 versus 10,000. It's 60K versus 10K. So what we're trying to do with ChroniFI is to get people to go, oh, okay, this is where this fits in. This is how this habit extrapolates to the rest of my life. Because there's this really beautiful part of saving that comes from the fact that, yeah, when I'm saving, that makes it so that I'm spending less, and so, therefore, I've got more money I'm stacking into my bank account each month.

That's. But if you liken it to a running race, that's just okay, I'm running a little bit faster. The cool part about saving is that if you are spending less money, then the amount of money you need to save in order to be financially independent gets smaller. So it's as you're running faster, also the finish line is coming closer to you.

That's the big kind of unrealized part of what people confront within personal finances. Expenses are everything, and again, it's not gutted to the bone, it's just making sure it's spent on the right stuff.

[00:37:40] Spencer: Yeah, I talked about in my book The Military Money Manual, how there are two levers you can pull, you can reduce the expenses and you can increase the income.

But if you pull them at the same time, then it creates this magical effect where all this, just like you said, you're running faster and the finish line is moving towards you, and then over time you've got compounding interest going to work for you. It's amazing how fast you can achieve fi, but even along the way, you can get to that point where you have so much in savings.

You have five years, 10 years. Of that F U money where you now have choices. If you want to, if you did six, 10 years of military service and you're like, I cannot make it to 20, go to the guard. Go to the reserves, get out. Use your GI bill, go to school, do something. If you're not happy living your life, don't gut it out to 20 years to earn that military pension.

Another thing you just mentioned was taking a stoic approach to investing and I'm a big fan of the stoic approach. I'm actually rereading Marcus Aurelius Meditations right now.

[00:38:38] Ben: Right on. Yep.

[00:38:40] Spencer: Yeah. Great. So much wisdom there. It to me I'm reading it and bed at night and I'll start giggling or laughing and my wife will be like, what's so funny?

And I'll just be like, it's the same problems in ancient Rome 2000 years ago as it is today. Humans do not change. All we do is we get new toys. We're literally hunter gatherers wandering the Savannah and someone just handed us an iPhone. It's crazy that these stoics were having the same problems and the same issues that we're having today, but are there any other lessons that you've taken from stoic philosophy and applied to your investing or to your life approach?

[00:39:18] Ben: Yeah it's another great question. I feel like I have to go broad on this one in the sense that hearkening back to earlier in the conversation, we brought up a bunch of books and things and merging that with my own lived experience. I knew that when I was, leaving act one to go on to act two, I don't know, I'm going to have to do some mental detox for a while and just figure out what do I want out of the next chapter of my life? 

And so I actually literally took several months after I resigned to just sit with religious and philosophical texts and just, there were 15 of them and I think three of them were stoics. So I was overweight that sector in the sense that I knew that I was interested in them before, and I had read Aurelius before then, but there's a lot of that philosophy that just intrinsically aligns really well with the way that I see the world. To answer your question more directly, some of the stuff that popped out of that study.

Equanimity in particular is I think an underlying theme, and it's got a lot to do with humility that we were talking about just moments ago, trying to be indifferent to the slings and arrows that life throws your way, has a lot to do with the way that you treat your investment. Has a lot to do with the way that you treat your career and your life, and just really trying to take a process over product sort of approach. Just follow the right process and don't be married in your mind to oh, this has to have the right outcome. 

There's just a substantial portion of life that's just variance. It's just chance. It's just randomness. So the less we kid ourselves about that, the better.

And you look at a guy like Marcus Aurelius. By the way, was essentially effectively kind of king of the western world at his time. He's still, you can read in his journal, which is what meditations is, he's like hemming and hawing about how do I be a better dude and it's just come on man, you're the king of the world.

What more do you want? But what an upstanding citizen in that respect. But he went through a lot of stuff. I think he had a bunch of kids that died and things like that. He was put through the ringer and despite the fact that he had a ton of power in all of that, there's a lot of extremes of emotion and extremes of the human experience that he had to deal with.

And through it all, this was a kind of philosophy that he picked to orient toward. I think there's a lot to recommend. It resonates with me super deeply. I would highly recommend Meditations. It's definitely on my top 10 list, although frankly, I've been pleasantly surprised. Few of the other books, that have already come up in this conversation, Housel and Vicki Robin’s book, among them have been other things.

And so what's one thing that I think people should draw from this little soliloquy here? Read. Make sure you. That is a huge deal because it keeps you fresh, it keeps you thinking about things that are not necessarily related to the matters that you're working on, nine to five or whenever you're doing your actual job.

But also it just helps to stir the pot. I would've been a miserable wreck if I didn't keep reading throughout my time in my finance career. Likewise, I'd be giving myself short shrift now if I didn't read, if I didn't do what's more important, what I think is more aligned with what you just asked about the Stoics.

Just some self-analysis, some introspection, understanding what it is you actually want and what that means in terms of the actions you should take.

[00:42:38] Spencer: Yeah, I love that. Any time you can encourage anybody to read, and it doesn't have to be a hardcover book. It can be on the Kindle, it can be audiobooks, it can be podcasts, it can be blogs, but I find it incredibly difficult to generate new ideas. But when you read things and you read multiple things, then what's interesting is your brain connects, you read something over here and something over there, and then your brain makes a connection between the two things, and it's those connections that maybe no other human in history has ever connected the dots between those two things, but you just did.

And so that's where the fresh ideas come from if you read the Stoics. Like I said, it's hilarious because they're having all the same problems and coming up with all the same solutions that all the self-help guys today are coming up with. But when you read them and you read the classic stuff and you read the modern stuff and you make those connections, that's where you get these fresh ideas and that's where you can change your life.

[00:43:32] Ben: What you just mentioned that line of thought, I love it. I have to mention there's a quote that came to mind and so I looked it up as you were speaking that I think just perfectly encapsulates that thought. It's Ralph Waldo Emerson. He says, “When the mind is braced by labor and invention, the page of whatever book we read becomes manifold with illusion.”

And so the idea there is just this, it is exactly what you just expressed. It's as iron sharpens iron, like when you're engaged in work, then all of a sudden these books come alive and vice versa. Because when you're reading these books, then all of a sudden what you're doing in your actual life takes on more meaning.

So anyways, I had to double-click on that because I love that line of thought. 

[00:44:14] Spencer: That's great. I'm going to pivot here now to a more high-level question, and I want to talk about Financial Independence. I depend. So one thing that we've heard from a couple of guests now is that you get to financial independence, and if you haven't created the life that you want, just getting to that finish line is not going to make you happy.

So in your mind, what is financial independence even good for? Then why pursue fi? Why restrict yourself today so that your future self can benefit?

[00:44:43] Ben: I want to question the premises of the question itself in the sense that why pursue financial independence, I would venture to say, has an obvious answer. But the fact that the question is asked, I think valid.

And I think it also belies the fact that people have these preconceptions about what financial independence even means. Let me unpack that for a second. The idea here is that this whole idea of financial independence, People think that means that work is bad. People think that means that work is something to be avoided at all costs and that you want to get your financial independence so you don't have to work anymore.

But in reality, you're painting with a lot more colors than that. It's overly restrictive to see early retirement, for example as well, that's what financial independence is. This idea of financial independence is one that encompasses a lot more than that people can. 

Let's start with the good sides.

The good sides of financial independence. People think it's just, kicking it on the beach forever and that type of thing. That's not what financial independence is about. For me, when I think of financial independence, I think about my friend whose wife was having a tricky pregnancy, and because they were financially independent, he was able to drop everything and use his time towards what was most important to him and to his family.

That is the power of financial independence. I think about a person who has dutifully saved money and put themselves in a spot where they can respond to opportunities as they arise. They can quit their job and go and work at a startup that's doing something interesting or better aligned with their values.

And so that's what's actually on offer. It's not just this wake up every day and go for a walk and then decide what you're going to eat for lunch. That's not financial independence or what it's actually good for now, this idea. What financial independence costs. There's this misconception that what are you doing?

You're sacrificing, you're getting rid of current spending in favor of future spending, and so what's that all about? I would venture to say that comes from a misconception that budgeting or that saving comes from a scarcity mindset. It comes from this idea. People assume that there's this scarcity embedded because it's oh, I'm depriving myself.

I would say that basically saving, budgeting, et cetera, that actually comes from an abundance mindset because what you're doing when you do that is you're saying, look, I think that there is a future worth saving for. I believe that there is something coming down the pipe. Which is going to be worth having some assets on hand.

And so it's an inherently an optimistic type of operation rather than a pessimistic one. So basically, what is financial independence good for? It's good for just having an expanded range of choices, financial independence, or, somewhere along that continuum gives you more options than you would otherwise have.

It gives you a position where you can actually just make decisions that are aligned with your values without being constrained by your finance. 

[00:47:52] Jamie: Ben, I saw on your Twitter feed, which is @chronifiben, right?

I saw on your Twitter feed about the 4,000 weeks book. You said that book was life-changing for you.

So now I'm curious, you got me hooked. Can you tell me a little bit about the book and why it was so impactful for you?

[00:48:06] Ben: Yeah, I'll say this. One, I've found that for me, it's very often the case that like when the student is ready, the teacher appears, and so this book hit me at exactly the right spot in my life to do maximum impact.

Essentially, what I took from that is you see a book with a title like that and you go, oh, it's going to be about life optimization, optimizing your time, et cetera. Time is precious and scarce and all these types of ideas. To be clear, there's plenty of that going on within the book. But the real upshot that I drew from it is that this whole notion of optimizing how you spend your workday, for example, or how you spend your day for another example, is in some sense, kind of misses the forest for the trees.

And so what I mean by that, and I guess what Berkman meant within his book is this idea that our to-do list is always going to be as long as our arm. That's just the way that life works. You always have problems, always things that you want to solve. There's a list of things that are itching to get off of your to-do list.

One thing that he spoke about in the book, which really resonated with where I am right now, is this idea that look, that's always going to be the case. You're always going to have more stuff that you want to do than time in which to do it. Accept that and opt into the present moment. That for me, hit me powerfully, especially as somebody with three little daughters, because it's just geez, all this stuff that I'm doing all day long, running around like a chicken with its head cut off is like trying to achieve some ends so that what, so that I can do what's most important to me, what's most important to me, being a good father to these three amazing little girls. So every time I'm like pulling out my phone while I'm around my kids because oh, there's this work emergency, and if I don't handle it now, then whatever's going to happen, the sky's falling. 

The reality is there's always going to be a huge list of things going on, but really the only thing you ever have is the present moment. That's another thing drawn straight from the stoics, is whether you're old or young, all you have to lose is the present moment. So this idea of really just taking that present moment, which is the only thing you have an opting in, that's the bottom line.

[00:50:20] Spencer: Yeah, I find so right now I'm training for a half Ironman, and so I have, a few hours a day of training, whether it's swimming, biking, or running, or sometimes all three in one day. What I find is when I sign up for these things, I lose so much of my free time because, not only are you doing the training, but you have to eat you have to get ready for the training, you have to drive the pool, and it just eats up so much of your day.

But then when I stop training for those things it's not like I get all those hours back, right? All those hours just slip through my fingers, right? But when I force myself and I sign up for the training, it's like all of a sudden I didn't get any more hours in a day. Whether you're rich or poor, everyone's granted 24 hours a day.

What do you do with it? That goes way beyond personal finance and achieving FI, those are those deep philosophical life questions, which I love to get into. I would say they're beyond the scope of the podcast, but actually, money touches everything

[00:51:16] Ben: It's all one problem at the end of the day.

[00:51:19] Spencer: That's right. That's right. We're all just trying to solve interesting problems.

[00:51:22] Jamie: So Ben, as our time comes to a close with you, it's been great today. Thank you so much again for coming on. I want to give you an opportunity to share a little bit about ChroniFI the software and what makes it different from other apps or other financial products that are out there.

Who's the ideal ChroniFI user? And just give us a little bit more information about the software.

[00:51:40] Ben: Sure. Thank you for giving me the chance here. Basically, ChroniFI is personal finance software that's meant to meet you where you are here in the present tense. So what I mean by that is so much software that's out there in the personal finance space is geared towards either the past what did I spend my money on last month or towards the future, like investing, I've got money, what should I do with it.

What we really try to drill down on is the present tense. Ultimately answering the question of, how does what I'm doing right now impact my overall financial health? Now, on the personal side, I used to be the guy who was sitting there in his bed on Mint every morning for 5, 10 minutes trying to convince myself that everything was okay.

I don't have anything against Mint. I used them for eight years. I think there are a lot of good things about it. It's not a direct competitor to what we're up to over here. Sure, we bake in some budgeting software, but the main meat of what we're actually doing here is just helping people understand here's where it all fits together.

Here's what it all means, and then dynamically tracking, because frankly, people who use budgeting software are still wildly off on what their lifestyle actually costs. Because when you bake in one-offs oh, I didn't think about the car, or the vacation, or the hospital bill, or whatever. Life is lumpy.

And so what we do at ChroniFI is we help people dynamically track that and amortize those one-offs out over whatever range they're actually useful for and get a bead on what actually their cost of lifestyle is. In a ticking sense, because we start with an assumption, and then over the first three months we bleed into, okay, here's what you're actually spending.

And then we update it every time they check-in. So what we do with that is once we've got that, it's the single biggest factor within personal finance, then we pipe it through to the metrics that actually matter so that people can understand here's what's actually going on under the hood, and frankly, put finance in its place because most people don't want to jump into the spreadsheet for three hours on Saturday morning.

What they want to do is get finance over with so that they can get back to living their lives. So that's what we've built is a way for people to check in, 10 minutes, twice a month, know that their finances are on track, and get back to living. So that's what we're up to. You can find it at and we've got a blog and podcast, too.

So if an hour of Ben Miller was not enough for you, then that's the place to look. 

[00:53:55] Jamie: You offer a trial, right? 

[00:54:01] Ben: Yeah, yep. Free 17-day free trial. No risk. Basically, just jump in, see if it's actually what we say it is, and if it is, cool, stick around. Otherwise, no love lost.

[00:54:07] Spencer: Ben, what are the names of the podcast and blog where people can find you?

[00:54:11] Ben: Yeah, so the podcast is the aptly named ChroniFI Podcast. You can find that anywhere podcasts are consumed. The blog is that, as you mentioned earlier,, and basically, That's pretty much the extent of our online presence. Honestly, I had no social media for a decade by choice and then starting a company had to jump back into the ring.

And so I'm on LinkedIn quite a bit, on Twitter occasionally, and that's pretty much a wrap, but always happy if somebody wants to reach out, if anything resonated from today, I can't get enough of this stuff. So I'm always happy to jump in and help.

[00:54:44] Spencer: That's great. Thanks so much for coming on the podcast.

Talked about a lot of really cool topics today that I think will resonate with a lot of our listeners.

[00:54:53] Ben: Thanks a lot for having me. It was a pleasure.

[00:54:56] Spencer:  Man, Jamie, I think we're getting really lucky with our podcast guests. Today's discussion I really benefit from it. I think Ben is, he's one of the good guys in the personal finance space.

I really like what he's doing with his ChroniFI app and website and just the ideas he discusses on his podcast and that he discussed in this podcast episode.

To review some of the ideas that we talked about today were how time is money and money is time. Imposter syndrome. How Ben learned humility on Wall Street.

We also talked about how Stoic philosophy can help you become financially independent and why you would want to become financially independent and how it goes way beyond just being able to do whatever you want with your time. 

As always, listener, if you have any questions or feedback, please message us on Instagram @MilitaryMoneyManual or you can email us. It goes to both me and Jamie We do love getting questions and messages from all of you and answering some of them on the podcast. We appreciate you joining us today and we're grateful for you listening. We'll catch you in the next episode of the Military Money Manual Podcast.

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