BiggerPockets Money Podcast - Does Money Buy Happiness? What the FIRE Community Gets Wrong

Episode Date: November 28, 2025

What happens after you achieve financial independence? Former Facebook employee turned comedian Paul Ollinger discovered the answer wasn't what he expected—and it completely changed how he thinks about money, work, and happiness. This Episode Covers: Why financial autonomy beats wealth accumulation—and what that actually means for your daily life The psychological challenges of early retirement nobody talks about (and why having a plan is non-negotiable) How he navigated major financial decisions in high-cost cities like New York without sacrificing his goals The truth about happiness and wealth—does more money actually make you happier? How to prepare for life's unexpected curveballs that can derail even the best financial plans And SO much more! Learn more about your ad choices. Visit megaphone.fm/adchoices

The fire community has this backwards. We're optimizing for financial independence like it's going to solve all of our problems. But what if reaching fire doesn't actually make you happier? Hello and welcome to the Bigger Pockets Money podcast. My name is Mindy Jensen. And with me, as always, is my happy and he knows it co-host, Scott Trench. Hooray! We are so excited to be joined today by Paul Ollinger.

Paul was one of Facebook's first 250 employees. He retired at the age of 42 and has gone on to start his own podcast. reasonably happy. And he's also got a successful stand-up comedy career. We are excited to talk about his relationship with money, happiness, and the aspects of the fire movement that absolutely terrify him. Paul, welcome to bigger pockets money. Thank you, Scott. Thank you, Mindy. Well, Paul, let's jump into it because we are a fire podcast talking to and about the fire community. What do you think about the fire community and the fire movement. I love the phi. I'm not so crazy about the er part of it or the re part of it because I think financial independence, the importance of financial independence in America,

especially today, cannot be overstated. And my wish for everyone is to achieve financial autonomy. That we mistakenly focus on wealth as the desired outcome as opposed to self-determination. And financial independence is something that has given me a great deal of joy in my life. And as I say to people, I was very fortunate to work in the right industry at the right time. I worked real hard and I made a lot of money. But the richest I've ever felt is the day I paid off my student loans. I want people to embrace that, to make that a goal, to be conscious of where they're investing their money and their energy in life and to make sure it's in places where it's going to have the highest return. We know you worked at Facebook did really well and now have branched out into a podcast and comedy.

Why do you declare that as not an early retirement? Like, I think that most people listening to this podcast would say, well, that sounds like a real retirement to me. I just happen to make money here. And that's how I view fire. What is that difference in your mind? You know, when I stopped working, I'd never thought about it as retiring. I just thought about it as like, I'm going to go figure something out and do something else.

The retire early thing, the reason I don't like it is because I think retirement is death's waiting room. You know, and there's been studies that have shown that people who retire early early die earlier than people who keep working. Sorry to jump in with that. When talks about those, we have to separate out the people who are forced to retire early due to health reasons. Tell me about that.

So what is the, if you take out the people who are forced to retire for health reasons, then what is the result of the study? It's very difficult to determine one way or another, whether folks live longer or less long after that, from a retirement standpoint. And also, there's very little research on the early retirement community in the fireworld. Anyways, that's an interesting tidbit there. He's wanted to jump in. Well, you know, we've seen lots of financial studies that have been done like the

Deaton and Connemon study about no additional happiness past $75,000 a year. And I was fortunate enough to be able to interview Sir Angus Deaton in his office at Princeton, gosh, going back six years now. And so that was really cool to talk to him. And he was a great guy. But we know through Killingsworth and, you know, some of the studies he's done at University of Pennsylvania that there is additional happiness and there's additional happiness to be gained at higher levels of wealth, blah, blah, blah.

It was my experience. I grew up always, I'm one of six kids. My dad always had a job while I was alive. We had everything we needed. We never had a ton more than that. My parents decided to send us all to Catholic school. So that was tuition money that he spent on the kids' education as opposed to on luxury goods. This subtext of our house was always that there was never enough money, that we always had to scrimp, that we always had to save. It was not an abundance mindset. It was a scarcity mindset. My brain came to the conclusion that I'm going to work card in high school, go to a good college, get a good job so I can make money and be happy. Because if I have more money, then I'll be happy. That was the mindset. And so from an early age, I was the kid who was going to be successful in business. That ended up happening, maybe to a greater financial extent, but not quite to the executive level as I had achieved, but whatever. When I got to a point where I was like, wow, I've got as much money as I'll ever need to live for the rest of my life, I was like, well, why should I work? Works just a big pain in my butt. They asked me to do a lot of things I don't want to do and live in places that I don't

want to live. And so I basically just walked away because I was stressed out about work. I was stressed out about carrying a quota every 90 days where they're like, okay, get up and do it again. And it was very hard and it wasn't life affirming. And so I quit. I walked away. I didn't walk toward anything. I walked away from something. And that's lesson number one. You should always be walking towards something. Don't just bail on your job without a plan. After three months, six months, maybe, I felt like I had everything I needed, but I didn't feel like I was doing great. I felt like I was a rich loser. Like I wasn't up to anything.

I tell this story that one night we were at dinner with some other parents of our respectively young kids. And I was talking to the dad. I knew he was a doctor. And I said, what kind of medicine do you practice? And he goes, well, I'm a pediatric oncologist and neurosurgeon. And I'm doing research down at the university using nanofibers to help slow the spread of cancer and the brains of infants.

What do you do? And in that moment, I'm like, I don't do shit, man. I do nothing. I sit around my big house and I work out and I go take a golf lesson and then I try to make it to 7 o'clock when I can open a bottle of wine. That's what I do. And so in this moment, it's kind of like you have this zoom out moment where I'm like, wow, I do have the opportunity to do whatever I want to do, but I'm not really doing anything. And so right about this time, I just started reading everything I could about money and happiness. Because all these assumptions I had made about money being the solution and the whole Jerry and McGuire, you complete me moment,

it never happened because I did get the money, but I didn't get the sense that it was something to be proud of. Now, it's a tool. It can help you go and do something else, but if you don't do anything with that tool and it just russes in a drawer. And so I at that point was like, well, I don't know what I'm going to do, but I'm going to start writing and going to open mics and doing stand-up comedy. I had gotten bit by the stand-up comedy bug years before in business school when I I stood up at a talent show and made fun of my friends for 15 minutes.

And so before I even went into the digital media business, I had this dream in my head. But when I left Facebook, I had moved back to Atlanta where I grew up from L.A., where I had done stand-up comedy and then went to Facebook. I'd moved back to Atlanta. I didn't know how to start over into comedy. I was a little embarrassed that I'd quit the first time. And so I was dragging my feet and dragging my feet. But eventually I got to the point where it's like, I have the money to do whatever I want

to do with my life. And if I don't chase my dream, that's a dereliction of opportunity. And that's when I started reading about money and happiness, coincidentally, writing about it, and then also going to open mics and get my comedy career back on track. Paul, I'm hearing so many similarities between your story and my husband's story. You said that there was a scarcity mindset growing up. How did you overcome that to leave your job? Because my husband grew up where his dad was laid off every winter.

He was an electrician. Then he had his own high-paying job when he was a computer programmer, not for Facebook. And it was hard for him to leave. He's like, I grew up with no money. Why would I leave this great-paying job just for this, like, abstract concept of financial independence? So how did you decide that enough was enough? It got to a point where, I mean, if you got to Facebook early enough, you know, you made some pretty crazy dough. And I got to a point in life where the interest on my nut would pay for a beautiful home,

private school, country clubs and great trips. And I was like, this is enough. What's interesting is like that was the lifestyle of the richest people I knew growing up. But what happens is, and this is one of the things that I, you know, we can talk about around the concept of retiring early is. You think you know what a lot of money is until you make it. And then you start hanging out with people who have a lot of money. And you go, oh, wait a minute.

A million isn't a lot. Five million is a lot. And you go, you know, wait a second. Five million isn't a lot. 20 million. That's a lot of money. And then you hang out with people 20 million. You start thinking, 100 million.

And it never stops. And that's why you see, you know, multi-deca billionaires having these competitions around their yachts and stuff because it never ends. I hung up my corporate career when I got to the point where I thought I had more than enough to live however I wanted to live. and I was also thinking about work just as a paycheck, as opposed to something I was getting more psychic income. I was getting belongingness from. I was getting self-esteem from.

I was getting camaraderie and a sense of purpose from. And when you just walk away from work and you don't replace it with something, which I didn't do for a couple of years, then you start to go, oh, that's what work is all about. We're going to take a quick ad break. But while we're away, head on over to YouTube. subscribe to our channel. That's YouTube.com slash at BiggerPockets Money. Tax season is one of the only times all year when most people actually look at their full financial picture, including income, spending, savings, investments, the whole thing. And if you're like most folks, it can be a little eye-opening. That's why I like Monarch. It helps you see

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Audible has been indispensable for me over over 10 years. Kickstart your well-being journey with your first audiobook free when you sign up for a free 30-day trial at audible.com slash BPMoney. Welcome back to the show. I think that one area where we would definitely agree with you on this overall framework is that there's a contingent of the financial independence retire early community who seem to have this purity mindset. I'm going to retire. I'm never going to earn another dollar of income.

And I'm going to do leisure activities most of the time. And there are even some people who go so far as to create blogs and never actually earned additional money intentionally to conform with that that viewpoint. And I think that that's way farther off out of left field than most people who kind of go through this exercise intend to, you know, intend for. I think there's also a clear, overwhelming sentiment in the community of, I want the option to retire early. I'm going to build a financial portfolio. I'm going to put my energy time and resources into it such that I have Paul's problem here where I can clearly not have to work ever again. Then I'm going to figure out what I want to be when I grow up,

or along that journey I'm going to figure out what I want to be when I grow up. And I think that's really the true essence of the fire community. There's this fringe contingent that's very loud, that's purist, and kind of annoying, frankly, in many cases around that. And that's not really representative of what the people who pursue financial independence retire really want. They want true portfolio that produces a true version of financial independence. And then we'll do things that they want to do over life. Some of the of which we'll make money. I think that's really what's going on here. A couple of things on that. One, I don't think if there's things that you want to do with your life, you shouldn't wait until

some period at X years in the future to start doing them. Don't wait until you have $2 million or whatever your number is. Because the overall number is a function of where you live, what you need, how much you can control your wants, how in line you are with your spouse on how you're going to conduct your household. There's too many variables there. And by the way, I could spend all our money very easily if I wasn't conscious of, I'm not super frugal, but I'm very conscious of what too much is, you know, at our level, because I want to maintain that flexibility. But like, if you're interested in a hobby, start doing it on the side, on the weekends. What I found was I've sort of fetishized certain things while I was working or use the mis of excuses like to hate work. Like,

oh, I really want to speak Spanish because, you know, I only took Spanish for three years in high school and college. And now I'm working. And if I wasn't working, I could speak really fluent Spanish because I could take time. Well, when I stopped working, I did start taking Spanish lessons for a few months. And we got to a point and, you know, the vocabulary comes back pretty quickly. But we got to a point in the classes where I was like, oh, there's like 17 different past tense versions of Spanish verbs. And if I really want to master them, I'm going to have to work at this. And I was like, I don't think I want to work at it. And it wasn't work. It wasn't my job that was keeping me from learning Spanish.

It was the effort that goes into learning how to speak Spanish. And the willingness to speak Spanish like a babbling kindergartner for a few years until you get to fluency. Oh, and by the way, if you want to speak Spanish, you should probably spend a lot of time in a Spanish speaking environment. Right. So like, do that. You know, so dabble in these things before you start to, you know, say it's going to be zero to 100 once I hit my number. I think that you have hit the nail on the head. One of my biggest problems with the fire community is that you're saving for the future. And I say this as though I didn't actually do this myself. I totally did. But I'm saving for the future. So I can't do it now because that's for the future. All this money is being put away for the future. I can't spend it now. I'm not going to enjoy my life now. I'm just going to get there as fast as I can. And then it'll be the future. Well, now it's the future. And what am I doing? I want people to, that's why I keep doing the show. I want people to. That's why I keep doing the show. I want people. to learn from my mistakes. And, you know, I am starting to see more of a shift in the fire community

of people who are saying, I want to enjoy the now. If it's taking me 10 years of like hard work or 11 or 12 of like enjoyment, go the 11 or 12 because you're going to get to that 12 year anyway, hopefully, and you want to have a good experience. I mean, I gave up a lot of things that I could have been doing with my kids because I was so hell bent on getting there. Question, Paul, now that you are gone. Do you wish you would have left sooner? Not at all. Regretting decisions that you've made that are irreversible is not a very productive use of energy or time. And so I made a good decision with the information I had at the time. I sort of had to make a move. They offered me a job in Minlo Park. So I had to leave Los Angeles and relocate my two young kids. My wife was on bed rest with our

second child during this time. It was not, it was pretty stressful time. So I was going to have to move up to Northern California and that was going to be the sixth move since I graduated from business school. I was tired of moving. I wanted to put down roots. And so going back to Atlanta and raising my kids in Atlanta and being around for my parents when they were dying over the next few years was a very positive life experience that I will never regret. I've sort of lived my life in a mode of minimizing deathbed regrets. That's why I do comedy because I didn't want to be on my deathbed thinking what would have happened if I gave it my all. And I have given it my all and I'm not famous yet and I'm not rich from comedy. I won't have to regret that. I was there holding both of my parents' hands

when both of them died. I won't ever have to regret that. If I had moved to Menlo Park, I would probably be worth, you know, 10 times more than I am, maybe five times more than I am. But then again, I might not know my kids as well. My wife and I might not have had such a good time up there. I could be divorced. Like, we don't know what another path would have taken. Yes, I left significant upside financially and professionally on the table. I didn't have another year to kind of dally around and wait. And so I kind of left when it was time to leave. And sure, I'd like another few million bucks, but what are you going to do? This is a great discussion here. Earlier in this conversation, you referenced the study, a very famous study by Connemann Deaton. And you said

you've actually talked to one of the authors, Deaton. Deaton, yeah. And that study said, hey, happiness increases until you get to $75,000. There's been additional research that has come across in recent years that has updated that, right? That's day-to-day. happiness, you're moved from one point at the other. There's another component to happiness that we need to consider here, which is kind of this concept of overall life satisfaction. And that does increase. It's not a linear. It's a kind of parabola here. It's a, it's a logarithmic. We had to bring geometry and trigonometry into it, Mindy. Now I feel dumb. Every additional dollar does correlate with this concept of overall life satisfaction, but the more turns begin to diminish greatly.

And there's another piece of research that Killingsworth, the other guy you mentioned, who has done some of this updated research, and they actually, all three of these guys, banded together to get a, you're right and you're right, a report out last year that kind of puts it all into an eat boat. East coast, West Coast economists, man, they'll cut you if you dis them. Yeah. So how am I doing so far? Am I getting this accurately? You're doing great.

You're doing great. But basically, this joint report and the new research from Killingsworth here, Professor Killing'sworth of University of Pennsylvania, I believe, suggests that this happiness does increase up to a point in plateau, but that the happiness associated with net worth and income is really most tightly correlated or directed towards life experiences outside of work. And people who earn higher income are not necessarily any happier at work. And I think that when I hear your story here, it's like a perfect output from that study the way this happened, right? You decide your net worth and your optionality is so great and your

happiness is probably so directly impacted by the wealth that you created early in life. And that is now realized with this new approach to work, I think, in your life. So how am I doing? Is this an accurate interpretation of how you're thinking about how things have gone in your life? And what do you make of those studies, given that you are clearly an expert on these things and referenced them unprompted? The theory behind the Connum and Deaton study that we took as as facts, for a decade or two, right? That, and this is what, 2010 or something they did the study. So time value of money, 75,000, maybe that's 150,000.

And of course, cost of living where you are, that's, you know, that's on average in America. So maybe in New York or San Francisco, it's 250 or, you know, $300,000. But there's a point. The purpose of money goes from being a painkiller to a vitamin, right? Like every additional dollar I made when I had no money in the bank was a pain You know, when your car breaks down and whenever you start, you're thinking about, you know, that engine, the knock you hear in your engine and you're dreading going to the mechanic because you know it's going to be $800 or $1,600, that's pain.

When you get into an accident, it's going to cost you $3 or $4,000 and you're going to get a ticket or whatever and you have no money or you got $5,000 or $20,000 in credit card debt. That's pain. But once you get to the point where, like, that stuff doesn't bother you anymore, your life is better. Your life is significantly freer of stress. And so I talk about this in one of the essays I published.

And it's about basically the best car I ever bought, the most exciting automobile purchase I've ever bought was a 1994 Saturn SL2. You know, I've driven Mercedes and Infinities and Teslas and things like that. None of them compared to the catharsis of replacing the beat up Honda with no air conditioning that I drove in Memphis, Tennessee in 1994. That car purchase relieved real pain. When you upgrade from a Saturn to a Corolla and then from a Corolla to a BMW 3 series,

those are nice, but they're not pain relieving. And so I really identified with that $75,000. And I think what that symbolizes is you're in a place where your life isn't a financial emergency all the time. And that's what I was talking about when I said, the richest I ever felt was the day I paid off my student loans. When I paid off my student loans, I felt as if I was my own man. I was an individual entity with a net worth of zero dollars and it felt wonderful.

And I want all of you to have that experience in life. Like I think that's what's missing in America today is this conversation around financial responsibility. It's nobody else's fault. It's up to you. You are a grown up. Make the decisions that are going to give you the opportunity to not be somebody's victim. And that's what that means to me.

Am I happier today with X millions than I was when I had 50,000 in the bank and I was single? I don't know. I got a lot more responsibilities than I did back then. You know, I see life very differently. I also know a lot of people, I know a few billionaires. And I really, I don't struggle, but I'm very conscious about not comparing my life to theirs. Because I didn't do the things that they did to earn that money. And they've made significant sacrifices to get where they're.

got and I wasn't willing to make those sacrifices and even if I had I probably couldn't have gotten there bringing this back to our friendly back and forth about fire and whether that there is a health component to that or not it's not fair to compare you know your happiness or state of well-being at one point in your life to another point I think you have to compare it to your counterfactual like if I'm in the same position at 35 with this situation am I happier being financially independent or not and I think that that answer is a clear, yeah, you're probably going to be happier financially independent to some degree over that counterfactual case. And I think that one thing that still bugs me is I really believe in what we do here at Bigger Pockets Money. I believe in pushing people to make the

sacrifices and earn that extra income and go all out and keep those expenses low and keep that spread very large so that your independence, the runway you have from a financial net worth perspective and liquid net worth perspective, the cash flow that that produces can actually give you optionality early in life. And I believe that that approach requires a pretty deep sacrifice for four or five years doing things you don't want to do necessarily in order to get that compounding journey going over. And then there's extreme unhealthiness taking it way too far for way too long after that. And there's kind of almost irresponsible or, you know, not quite mathematically sound approach of pulling the trigger too early in other cases. But many of the people in the fire community,

I think get that balance generally right. And then they struggle with this problem of what I want to be when I grew up once I actually hit financial independence. And that's a year's long journey as they approach and exceed it. Even if you work a traditional, not that these exist like they did, you know, 25 years ago, but even if you work a traditional corporate job, come out of college, maybe you get a graduate degree and you go into the working world and you work for 35 years and then you retire. Everybody's going to have this inflection point at some point where you have to decide,

well, what are you besides your job? Like, what do you stand for? What do you care about? How do you want to spend your time? And it's still going to be an identity crisis of sorts where you have to say, who do I stand for? What am I? You have this when your kids leave home when you become empty nesters.

A lot of my friends are going through that right now. My kids are a little younger. They're still in high school. But like, you have to say, well, who am I besides being a parent on a day-to-day basis? How do I relate to my spouse? Are we still like copacetic without the kids as a bonding agent? And how are we going to spend our time together? And you have to be on the same page.

And that's a question that comes back to values, part of which are financial. values. I really like that. I think a lot of people don't think about that. And when you said the RE part is not what you like about fire, I have said that multiple times too. So many people are focused on the RE. They're not thinking about the FI. They're not thinking about what they're going to do once they leave. I know lots of people in the fire community who have left and then found some other way to either generate a small amount of income or produce something that they are doing that makes them happy that isn't producing a ton of income because they don't need it anymore. They already got money out of the way. I love that you're saying this too.

I'm happy to share my point of view for whatever it's worth and everybody's got their own journey to go on and they've got to do what's right for them. My problem with retire early is I see a lot of 28, 32 year old guys have been doing stand-up comedy for 10 years. They've been baristas, if that, you know, in their career so far. And I'm like, dude, you are going to be screwed when you're 45 years old unless you make it in comedy. And the chances of you make it in comedy are extremely low. I had a career counselor in business school, Steve Lebrano, who was amazing. And my first year, coming back to my school after graduating, I was saying, I want to go do stand-up comedy. He was like, make your money first. Make your money first. Don't just bail and chase your

dream because your value in the marketplace diminishes rapidly once you drive it off the lot. Isn't this fire? Like what I think of fire, and I think I think some people, like, it means some different, different people, but I think you just described exactly what we are trying to do here to a T. Like there are so many people out there who are a director of marketing or an FPNA, you know, financial planning and analysis at their company. And that's not their passion, but it pays the bills. And they're on the fire journey. And they're going to be there in five, seven, eight years if the market cooperates anything close to historical averages and they do all the right plays. And then they can go and start their comedy podcast. Oh, don't start a comedy podcast.

That's what I'm telling you. Don't do it. But that's the point is there be financially independent so they can do exactly what they want. And that's their passion, their joy. They don't care if it makes money. That's retirement, right? Retirement is not doing nothing and playing video games all day. It's doing what Paul does. It's making this content that somebody enjoys, even if it doesn't make money because your portfolio enables you to do that. Just be really diligent about your math and as diligent as you can be about your future psychology without being able to do any calculation. Let me tell you this.

Sorry, that sounded didactic or pedantic. One of those things. I don't know what it is. Here's my, here's been my experience. You quit with an amount of money that sounds and feels like a lot. And it still is a lot and I'm super grateful. But guess what? The clock doesn't stop ticking.

Your peers keep working and moving on. And your peer that was a vice president becomes the CEO. And the people you start hanging out with, the bar keeps moving. And yes, we can practice meditation and awareness and mindfulness to be grateful for what we have and to not let the moving gold posts affect us too much. But you notice. And so unless you can keep really earning and keep moving that thing forward, it doesn't feel like a victory every day.

How do you feel about it? Right. Like, is this, did I not describe your situation to some degree? You made a boatload of money. Yeah, I did. And I'm still wildly fortunate. And I still watch the markets. And I'm still trying to be prudent, but, you know, generate as much cash as I can safely.

I'm just saying that these things we talk about, like just retire and you'll have enough, the question is to what is enough changes all the time. And because our life circumstances keep changing. Maybe you have a third child that you weren't planning on having. Maybe that child has some sort of disability. That means you need an extra 20% of net worth to cover that child's medical expenses. You know, maybe you get divorced. Well, that wasn't on the menu.

Like, I'm just saying life happens. Circumstances change, which makes your previous math not as accurate as it once was. Like, if I needed a job, if the market tanks by 75%, I'm not in a good place anymore. I'm still fine. I'm just not in a great place. And if I were to try to go back and get another job, it's not Paul Hollinger, vice president of sales at Facebook. It's Paul Ollinger. What do you got? How can I create value? Like, who will take me after being a stand-up comedian for 10 years? I could find something.

I could find some things that are pretty good, actually. But it's not like, you're not going to go back making a million bucks a year after you've been out of the workforce for 15 years. That's all I'm saying. That's the sort of you don't know what's coming down the road. And so, Scott, to your point about like, yes, as long as you've created those cash generating tools in your life, they just have to be robust. I mean, really robust and probably more robust than you think they need to be. Because between 40 and 56, life changes a lot more than you think it will. One thing I will call out is that a huge percentage of the fire community has all of their wealth, effectively all of their liquid wealth in S&P 500 index fund portfolios. And that is not a good place to have all of your

wealth if you are declaring a state of financial independence because the market can and will be volatile to that point. It will display a 50% drawdown at various points in your life. And that, you know, I don't know, 75% maybe that's even possible, you know, stocks at all time, high sales to price ratios. So I think I think you're completely right. And I think that's the, the rub here is that if you're going to declare that and really go on this different tangent, you got to be pretty sure. I do think the paradox of it is that the withdrawal rules, because that that fear is so acute in the fire community. I mean, how many times, Mindy, have we discussed the 4% rule? We've had endless, endless debates about, you know, 60, 40,

stock bond portfolio, risk parity, golden ratio portfolio, here's all the different incorrelated assets, here's all the historical cases and we'll be a little bit more conservative on top of those anyways and build a big cash buffer and all that kind of stuff. So I think people do respect that message that you're giving us right now to a very healthy degree, maybe something perhaps even to an unhealthy degree by going so far and away over the numbers that are supported by historical research that they, you know, that there's no historical context where they could possibly get disrupted. I would argue that most people in the fire community actually who actually do pull the trigger are likely in that extreme tail end,

if they plan to truly earn no money afterwards. But I'll also call out that a third of Bigger Pockets money listeners specifically intend to and plan to start a business after they achieve financial independence. And another third, say, perhaps I might in there. So that's probably half the community that will pursue some form of business endeavor after financial independence. And who's to say that a self-made multimillionaire early in life is not likely to succeed in business to some degree after early retirement? 100%. And that's not necessarily a resume killer, right?

Like you're a director or a VP at a company. Then you go and start a business in your early retirement and then you want to go back in the workforce. I don't know if that's a resume killer. I don't think it is. And you'll develop new capabilities and knowledge that will make. make you more valuable in the marketplace. If you go and start a podcast and do it for 10 years and it doesn't work out and Spotify or Megaphone doesn't want to hire you, you haven't built your

industry knowledge or status. It hasn't kept pace with, you know, the marketplace. Mindy, let's hope it works out. I hope it works out. But also I would not. I mean you guys to help me make it work out. Go listen to Paul Ollinger's podcast called Reasonably Happy. It used to be called Crazy Money. There is a financial component in there. So go listen to his show. after you listen to all of ours, of course. I want to ask you something here, Paul. We have talked to a lot of people who have made it into the top 1%

and wealth on this podcast, and many of them, in fact, I would say the great majority of these top 1%ters have some kind of outlier investment that propels, you know, income or investment that propels them into this position, right?

For Mindy, it's, in Carl, it was these technology stocks that they picked that really zoomed up over time. For you, it's obviously going to be meta. And the stock that you got as an employee, that ballooned. When we find people with those positions, there's a one great situation because we're rich now, and two, a problem because we're highly concentrated in one highly volatile asset, that we're not quite sure how comfortable we feel about as comprising that much of our net worth.

And it's hard to get out of that position because there's a tax consequence to realizing gains in many of those situations. At the highest level, can you talk about what that looked like for you and how you thought about bridging from what is or was a highly concentrated position in meta stock than Facebook to a more diversified portfolio that makes you feel better about your position today. Yeah, there was a point at which a few, many years ago, my financial advisors asked me what my goal was, and I said it was to sleep at night. And so we started a methodical drawdown of Facebook as a percentage of my overall net worth and sold off. you know, on regular, a regular basis. And we sold some of it pathetically early, you know, painfully, painfully early for a stock that's at whatever, 600 bucks a share now. I mean, 10% of that or way less. But you can't worry about that, you know. And I was fortunate to have

the right skills at the right time and the right relationships to get a job at Facebook. I've been lucky to hold onto a stock that has had so much upside. That's what we've lived on. The appreciation of that stock is what we've lived on for the last 14 years. And that's certainly not something that, you know, you can bet on. So we have less than we'd have if we had held on for a long, long time. But I've slept better at night. And I haven't had to worry about missing any rent payments or missing any meals along the way.

What did you reallocate to? Did you just harvest it and spend it? Or did you reallocate portions of those sales to like an S&P 500 Nix fund or other portfolio assets? We reallocated into a portfolio that, uh, has lots of stocks and bonds, some real estate, things like that. And we always do it with an eye on taxes and understanding where we are in the year versus what we might need to live on the next 12 months, always have plenty of cash in the bank

so that we don't have to sell. If the market takes a big dip, when COVID happened, we weren't in a position where I had to sell tons and tons of stock to meet our expenses on a month to month basis because we'd already done it. And so we rode the dip out, sold nothing, and everything came back. And so that's a fortunate position to be in. What does tons of cash mean in terms of monthly or annual spending? Not as much as you think.

And when I say cash, I mean, cash equivalence also not just sitting, you know, under the bed or in the same. Right. What's the percentage of it? I don't know. I mean, we've got probably nine to 15 months worth of cash or cash equivalence, you know, in our portfolio. Does your spouse work? She has our own small fashion accessory brand called Sidecar, and it's a very cool thing that also does not make a lot of money.

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Visit Northwest Registeredagent.com slash money-free and start building something amazing. Get more with Northwest Registered Agent at Northwest Registeredagent.com slash money-free. Thanks for sticking with us. Let's keep chatting with Paul. In terms of like annual or monthly spending, What sort of income are you generating from your stand-up job and your spouse's job versus what you're pulling out of retirements? Well, it's not really retirement. I mean, you know, it's a living, living, breathing portfolio that will, well, retirement is a, is a weird word.

He doesn't like the word retirement, but he has a very suspiciously retirement, early retirement lifestyle. You guys make it sell like, I don't have a, I don't have a fire voodoo doll. I don't know. I think we came at this the wrong way. I don't. No, I think you're making really great points. I think people have this idea that once I get financially independent, my whole life is going to change and everything's going to be great.

And that's not true. You don't change automatically just because you no longer have to have a job. You're the same person you were before. If you were a jerk before, guess what? You're still a jerk now. If you were super awesome before, you're super awesome now. If you had a terrible relationship with your partner, that's not going to magically change. In fact, it'll just get worse because you're spending more time with them.

Money amplifies who you are. It doesn't change you so much, I think. Good and bad. So the question was how much, I mean, you know, look, we're in a good year after you deduct things like podcast production, promotion, travel. If I'm clearing on my comedy and professional speaking of which I do a decent amount, which actually pays quite well, you know, if I clear 100 grand on that, then I'm excited. And it's because, you know, being a creative independence, very expensive. And, you know, travel, if you want to travel halfway decently is, you know, it's also expensive and getting more expensive all the time.

So, yeah, so if I'm clearing 100 grand on that, I'm pretty excited. And living in New York City. And then everything else is, and everything else. Yeah, that doesn't even cover one kid's private school tuition after taxes. New York City is absurdly expensive. It's, I mean, private school is $70,000 per child. And so if you're in the fire movement, you probably don't want to live in New York City. You certainly don't want to send your kid to private school.

I think that's a big thing, though. Like, I don't really know a lot of people in the fire community that are in New York City. I just don't think it's a thing. I don't think it's like the desire of people in New York City to retire early. I think that it's just so hustling and bustling and there's so much to spend money on and there's so much to do and see that it's different. Like here in the burbs of Southern Denver, like there's, the fire is really appealing relative to Manhattan because the things I want to do with my day on a Tuesday are like, oh, I can go to the

mountain ski with there's no lift lines or whatever. And that's a really big difference in mindset. And I think it's very popular out here in Colorado. This is not an uncommon thing. I'll meet random people. And it'll come up and that'll be like, yes, that's what I want. But you don't really hear that from Manhattan. Yeah, the things you want to do in Manhattan cost a lot of money. You know, my wife and my anniversary was yesterday. We went to a very expensive restaurant. And it was lovely and it was romantic. And it was nice. but it was expensive. We're going to go see Stevie Nicks tomorrow night in Brooklyn at whatever the arena is there.

You know, it's a thousand bucks for the tickets. I mean, like, it's absurdly expensive to live here and do the kind of things that people want to do when they live here. I'm sure there's people in the fire movement here, and I'm sure they've got all the kinds of cool New York hacks and all that, but it's an insanely expensive place to live. I would like to invite all of our New York City members, listeners to email Scott at biggerpocketsmoney.com. and let him know that you are there and thriving in New York City. Yeah. I'm not saying it's not thriving. I'm just saying I think that the folks who have the hardest time grasping fire

tend to be relatively high-income earners in New York City. Like, I'll call out Ramit Sethi, who posts a fire-bashing Twitter post, X-post, once a week, it seems like on there. And I get it. I get it. You live in Manhattan. You have another house at L.A. There's so many five-star restaurants to spend money on. Like, it's incomprehensible in there.

But if you lived at, like here where I live, the public school is a 9 out of 10. And the private school is a 9.2 out of 10. There's no advantage to spending 40, 50 grand a year in private school tuition where I live in a relative context. It matters much more greatly how much what I do as a parent than that marginal spread. In New York City, it's probably a big difference. The public school is probably very different than the $70,000 private school you're doing there. And it's so much greater that there's a real desire and need to a certain extent to have that

income difference if you want to provide that extra level of advantage and you have the capability to do so. I think that that's the rub. And maybe that's where, maybe that's where this gets mixed up a little bit is that it's very hard in L.A. in New York City, San Francisco, maybe a couple other places to really comprehend this concept at all. And it's much easier if you live out many other places. Well, these are choices, right? And if if your goal is to live a life of happiness is a broad, is a word with a lot of definitions, but if you're looking to live a life of contentment and satisfaction and fulfillment, that you can do that in places that cost a lot less and you can invest your money in the things that you really care about, like sweet trail bike as opposed to,

you know, crazy private school tuition that is 0.1% better than the public option, right? In New York, there is that huge difference. There are outstanding magnet public schools in New York City, but you have to test into them. And so not everybody gets a chance to avail themselves of those schools and they're highly, highly competitive and maybe not a great place for your kids. So I'm a big believer in what you say, spend your money in ways that are going to maximize your satisfaction and on the things that really matter and not on stuff. You don't care about like, so last night, for example, we went to this incredible French restaurant and I was talking to my friend about it who's a big time hedge fund guy and he was

saying he wanted to try it. And I texted him this morning. I was like, dude, it was great. It was elegant. It was lovely. The food was magical. The experience was cool. And if I had to choose where to go to dinner tonight, I'd go where we had fried chicken

last week because I just thought it was a better restaurant experience. And it wasn't cheap because it's New York City, but it was a lot cheaper than last night was. Yeah, I would say the fine dining options here in Highlands Ranch, Colorado are limited. Happy Hour begins at eight at the local brewery. So it's a little different vibe out here. Well, you know, there's there's something out there for everybody. There is. So Paul, open invitation to come visit us whenever. The next time you are in Denver, I want to come see your show. It was so nice to see you in Denver. So I want to give a shout out. to David, who I met through the Choose Fy Denver local groups or at a campfire. I can't remember. I've seen him a ton of times. He posted, hey, does anybody want to go to Paul Ollinger's show in Denver?

My husband and I went. You were hilarious. I stopped out. You stood outside the door and you were shaking hands with everybody. And I asked if I could have you on my show and you're like, oh, sure. And then I had taken a picture of you and sent it to Joe Sal C. Hi. I'm like, this dude looks just like you. And he said, oh, I know, Paul. He's been on my show. show. I'm like, could you introduce me to him, please? Joe has stayed in my house in Atlanta. I mean, we're pals. He came through on his book tour and we hung out. He was in my basement on his book tour too. I didn't keep him in the basement, Mindy. I put him in the guest room. Well, you're better than me. Oh, I'm sorry. I thought you meant you tied him up in the cellar.

Never mind. He's used to the basement. That's where he records in his mom's basement. That's true. That is true. I forgot. That's very good point. He likes the basement. He likes a dank, dark area. It's not that dink. Okay, so Paul Ollinger, thank you so much for your time today. I had a lovely time chatting with you. Please tell our listeners where they can find you. Best place to follow me is on my substack. It's words.

Paul Oll-O-O-L-O-L-O-L-O-N-G-E-R. Paul, O-L-O-L-I-N-G-E-R. Paul, this has been fantastic. Thank you for coming in and providing such a thoughtful challenge to the concept on fire. I think we are trying to communicate very similar things, and the language that we choose in there is really important. I think it means very different things to the word financial independence retire early has a different register, like a register is differently in my brain than it does in yours,

and that's okay. It makes a lot of sense. And it sounds like you've been very successful and have a thriving career and are doing wonderfully. And I look forward to seeing you next time you are here in Denver. Any Scott, thanks for having me. All right, Scott, that was Paul Ollinger, and that was a really fun conversation we just had.

What did you think of Paul? I thought Paul is like a classic example of fire, right? Like he's using different terminology. He rejects the term. But like this is a guy who built a huge net worth early in life through, you know, Facebook and then, you know, now meta stock that appreciated. And now he gets to, you know, do whatever he wants. And he's chosen to pursue this comedy career that blends comedy and a little bit. He's an expert on happiness and the science behind it and has really studied that and spoken on those topics as well.

And that's a good career. It's actually a quite good career. We talked about making almost $100,000 in some years with that career. But his framework of other folks that have made up, you know, Buku dollars from META and that live in New York City and send their kids to private school doesn't seem like that much income. So he has to rely on his portfolio. To me, that's a fire outcome. That's the outcome that we are trying to enable en masse for the people who listen to Bigger Pockets money. It's just that he rejected the terminology.

What did you think? He is FI, but he wasn't pursuing FI. He's like FI by accident, not on purpose. So I can see why he doesn't identify with the community as much as somebody who was actually doing it on purpose would identify with. And also, he's really anti-retire early. Even though he did leave his job, he doesn't consider himself retired. And I think that like you say,

said, Scott, it's all semantics. We're talking about the same thing. But it is your mindset. And his mindset is not one of someone who is in the fire community. I wonder if it's a little bit because of the frugality aspect, too, and that he's not frugal. I really want to explore that concept of Manhattan specifically. Let's focus on Manhattan and not broader New York City because we have plenty of folks who follow the podcast from New York City. But I would be surprised if we have a large contingent of Manhattan-based listeners to this podcast and that are pursuing fire in general. I'm sure they're out there, but please email me if you are in Manhattan, Scott at biggerpocketsmoney.com, and tell me about this. But I think that as a young person,

I would have had a lot of trouble with the fire community if I was living in Manhattan. I've been there a few times, and it is not really conducive to that mindset. It's very difficult to justify, I think, the concept of early retirement when there's so much to see spend and do, the world's best of everything is right there at your fingertips. And I think it's a little harder to comprehend, you know, when you don't look out your window and see the mountains right there, which are free and fun and wonderful, that's a very different draw that comes to your mind every day living in Denver and looking at those things. Then there is going out your door and knowing that the best food, entertainment, and fun in the

world is right there as long as you can spend money. And so I wonder if that's a dynamic that we're seeing. Okay, I asked everybody in Manhattan to email Scott at biggerpocketsmoney.com. Please see me, Mindy at biggerpocketsmoney.com, because I want to see how many people are there. I know several people that live in Manhattan. Paula Pant lives in New York City and Broke Millennial lives in New York City, or at least she did. I actually haven't talked to her in a while. I need to send a note to Aaron.

But I know multiple people who live in New York City and are pursuing fire. I think you can pursue financial independence in any city and you spend the money that you choose to spend. And if you decide not to do all of these expensive things, then you decide not to. Or maybe you make friends with the stage manager and you can get in for free or you can get in, you know, on discount day or whatever. There's lots of ways to enjoy your life without spending full price. I completely agree. And I'm not saying there's not out there. And I know all those folks. I just think it's a little harder. I think it's even harder relative to a place like Los Angeles or these expensive places. in California because there's a lot of free and wonderful activities you can do there as well

out there. Not as much, I feel like, that you can do that's free and wonderful in New York City. Maybe I'm wrong. Maybe someone will tell me about that and educate me on this. Central Park? Central Park is great. So, yeah, these are the things that I don't know about New York City, and I just wonder if it seems like a lot of the people who are most anti-fire seem to concentrate in Manhattan or the New York City area. Remember, this is Scott saying this, not Mindy. All right, Scott, should we get out of here?

Let's do it. That wraps up this fantastic episode of the Bigger Pockets Money podcast. He is Scott Trench. I am Mindy Jensen saying, cheers, dears.