Hey everyone, and welcome to Passive Real Estate Investing. I’m Melissa Nash, your guest host jumping in for now.
Let’s dive in. Do you think that you need to hustle for 40 years to become a millionaire? Well, think again today I am talking to Sam Dogen, AKA, the Financial Samurai, who walked away from Wall Street at 34, negotiated a severance and build a seven figure portfolio by thinking differently. In his new book, millionaire Milestones, he shares the simple mindset shifts and action steps to build real wealth without giving up your life to do it. This just might change the way that you think about money forever. Let’s get into it. Welcome everybody. Today’s guest is someone whose name might already be on your bookshelf or in your podcast queue. Sam Dogen is better known as the Financial Samurai. He is one of the original voices in the financial independence movement. And after a successful career on Wall Street, he made a bold move. He retired at 34 and started writing about personal finance in a way that actually made sense for real people. Since then, he has built an audience of millions, authored a Wall Street Journal bestselling book by this, not that, and his newest release Millionaire Milestones, Simple Steps to Seven Figures. And it’s all about helping people take care of their finances the right way with practical, actionable steps.
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Sam, I am so excited to have you here today and welcome to the show.
Hey, good to meet you Melissa, and thanks for having me.
Absolutely. I am so excited. So now, I was telling you a little bit earlier before we hit record, I was recently in Miami and I got an advanced copy of this book so that the timing was perfect to be able to read it on the airplane. But before we go there, before we dive into the book, I would love to hear a little bit about your early days. Who was Sam before the Financial Samurai and what made you walk away from that traditional career so early on?
Yeah. Well, I grew up overseas in multiple different countries ’cause my parents were working in the US Foreign Service and I just started seeing the dichotomy between the very wealthy in Malaysia when I was in middle school and the poor and all the wealthy people were entrepreneurs and businessmen and women. And so I decided, hey, I think it’d be better to be rich than poor. So I decided to study economics, study finance, and go work on Wall Street because I thought it was very fascinating to be able to click some buttons to make some money <laugh>. And so it started in 1999 at Goldman Sachs in New York City. The pay was actually pretty bad. It was $40,000 base salary plus a bonus. And it was hard living in Manhattan on $40,000 actually. So the grind was intense. It was [spp-timestamp time=”5:30″] AM into the office when it was dark and you’d leave after [spp-timestamp time=”7:00″] PM maybe [spp-timestamp time=”8:00″] PM [spp-timestamp time=”9:00″] PM a lot when it was night.
And I’d had to connect myself with Asia because I was working in international equities. And so I really remember the first month, two months, I was telling myself, I don’t think I can last in this crazy, brutal competitive industry for a long time. And so I needed a way out and I thought to myself, okay, let me work for 17, 18 years outta college, get to age 40, save as much as possible, and then I’m out. I want to get out and do something else. There’s no way I could last the traditional retirement age of 60, 65. And actually at age, well, in 2009, at age 32, I finally decided to start Financial Samurai. July, 2009. It was almost, I think it was about the bottom of the global financial crisis. ’cause I was thinking to myself, I’m gonna get blown out. There were seven rounds of layoffs already over a two year period. That’s just it for me. I can’t last until 40. I’m gonzo. I needed a backup plan. And so I started my backup plan with Financial Samurai. It was a cathartic way to get through all the chaos, fear, and uncertainty, kind of like now in 2025. And one thing led to another. And by 2012, about almost three years after I started it, I engineered my layoff by negotiating a severance package and walked away at 34.
Wow. That was pretty bold. <Laugh>
<Laugh>
Especially, there’s so many entrepreneurs that listen to this podcast specifically, and we think of security as the corporate job. You know, Goldman Sachs, that’s like security for so many people. ’cause That’s what we’re taught. We’re taught that in school. We we’re taught to be good employees and to go to college and to get that secure job. Yeah. And then to just walk away from it is, is actually quite brave. It’s not, it’s not the normal.
Well, I was definitely terrified. I was thinking to myself, what am I doing? There’s, my base salary at the time was $250,000, which was a great base salary for a 32, 33, 30 4-year-old. And there was a bonus if times were good, but I was also miserable at my job. I was experiencing chronic back pain, sciatica, TMJ plantar fasciitis, all these ailments that I was just living with for the past 10 plus years because of all the stress, pain and suffering and pressure. And at one point I told myself, I was thinking to myself, this is kind of ridiculous having, I’m an adult man, getting told what to do by other adults and to do it, you know, and to work very hard in 60 plus hours. I just said, this is not just, this is not the way to live. And so I was trying to figure out my escape hatch because on Wall Street they pay you a base salary plus a bonus.
And the bonus part of it is comprised of stocks. And part of it is comprised of deferred cash as well. So if you get your bonus, you don’t get all your bonus, you get maybe 50% of your bonus, and then the rest is deferred over a three or four year period. So it’s the golden handcuffs. And by that time I had worked, I had moved to Credit Suisse and I had been there for 11 years, and if I had just quit, I would’ve lost hundreds of thousands of dollars of deferred compensation, which was, you know, a no-no, I couldn’t do that. And so I had a bright idea after seeing so many people get laid off and talking to so many people who did get laid off what their severance package was. And I thought to myself, well, if I could provide a smooth transition for my employer to train my junior employee to cover my accounts, maybe I can get a severance package and leave. And I brought that up in, I think it was January, 2012 after a terrible bonus in 2011. And they said, let me get back to you. And then two weeks later, my managing director based in, I think it was in New York and also in Hong Kong, said, actually, okay, let’s try to work something out. And so we worked something out. I stayed on for a couple months, trade my junior, and they gave me a severance package and all my deferred compensation that was coming to me over a seven year period actually.
Well, you know, the takeaway that I, I mean you ask, you know what I mean? Like so many people, we get caught up in this so afraid to ask for what we want, ask for the opportunity, ask to do things, put ourselves outta that comfort zone. You asked <laugh> that. Honestly, that is the the golden answer right there. Just ask and let other people come up with solutions, right? <Laugh>
Well, you know, it’s also putting yourself in your employer’s shoes because the last thing an employer wants is an employee to say, see you later with a one day notice. I’m gone. Because that leaves a big hole in your po in their pockets in terms of productivity and, and profitability. So if you can think about, okay, let me find my replacement, let me train my replacement, let me ensure a very smooth transition so my manager is not freaking out as well. They’re gonna be more amenable. If you’re a bad employee, they’re actually gonna be amenable to getting you out because you might be a cancer to the, the organization. And if you’re a good employee, they might be amenable to providing a severance package because you showed so much loyalty and thoughtfulness and commitment to the company over the years. And so you have to be brave enough to ask for what you want, but in a respectful win-win manner manner. And don’t just do the, you know, ghosting and never respond to anybody and what we do in society now, you know, confront them, but in a respectful way to ask for what you want.
Amazing. That is such, such great advice and very appreciated right now with, like you said, social media. And it’s just so easy to hide and ghost it just in relationships and in business. So with that, let’s jump into the book. In fact, that comment is one of the things that kind of I wanna talk about is that you broke down in the book is in three phases, right? So we’ve got growth, lifestyle, and legacy. So let’s rewind a little bit and kind of talk about how can we weave these things into our daily everything. A lot of people on here are looking for that exit what you did. So let’s just jump into it. So take us away with this phase journey that you lay out in the book.
Well, that’s a pretty long journey and a pretty comprehensive, but in your twenties and thirties, if you’re, if the amount of money you’re saving each month and investing each month doesn’t hurt, you’re not saving enough. The problem I see, and I’ve been writing about personal finance since 2009 on Financial Samurai, is that people have excuses. They complain why they can’t save or invest, and then they just wing it When it comes to their finances, they’re not meticulous, they don’t plan, they don’t save until it hurts. And then 10 years later they wonder where all their money went. We all know that compounding is one of the most powerful forces in finance, but you need to build that nut initially to get to that compounding phase. And I, in my book, I talk about you wanna try to get to $250,000 in savings and investments. Now to get there, obviously you gotta save your first thousand, first 10,000, first 50,000.
But once you get to 250,000, that’s really when the magic happens. Especially if you’re at an employer that provides a 401k, for example, in 2025, the maximum employee contribution limit is 23,500. And imagine if you had a $250,000 portfolio. We know from history that stocks show a positive return about 75% of the time, and the historical rate of return is about 10%. So if you had a $250,000 portfolio and a 10% return, that’s $25,000. So you’ve now, you can now make potentially more from your investments than your contributions to your 401k, for example. And that is an amazing effect because over time, that really starts compound and grow. You know, I used to talk about, okay, the first million might be the easiest because you’re young, you’ve got energy, you’re not encumbered by responsibilities of aging parents and young children asking for your attention and everything. But I was wrong. The first million is the hardest. Once you get to that 250,000, get to 1 million, it’s much easier to get to the next million. Once you get to that 10 million, you’ll be surprised, several good years, you can get to that 20 million. But the problem is people don’t focus, don’t plant, and don’t save and invest until they hurt when they’re in, in their twenties and thirties. And that really starts putting them at a drag later on in life.
Yeah. So what is the biggest mind shift that someone needs to go from paycheck to paycheck to thinking like a millionaire in the making? Because you know, that sounds like a very scary number for people right now to go, how can I save that $250,000? You know, that that is a big number to a lot of people, let alone a million, 5 million, 10 million. So what is that mind shift?
Well, one of the funny things I like to tell myself and and to financial samura readers is you need to focus on forecasting your misery. And what do I mean by that? It doesn’t really matter what you do. If you do something long enough, you are gonna start getting miserable and bored about that thing. You know, your first job, you’re excited, 10th year during your first job, you’re gonna be really miserable and bored. You need change, you need excitement, you need something new. So again, it’s about planning ahead. You need to forecast your misery so that by the time you are miserable, you have the money, the passive income to do something else. It’s interesting because 250,000, it might sound like a lot to some people, might not sound like a lot to other people, but it’s not, you gotta get to 250,000 right away.
If you cut that money up, let’s say over a 10 year period and you crunch some numbers into a calculator, if you save $10,000 a year after 10 years, but then you get a 7% annual rate of return, you can get there, you will get there. You don’t have to think about it immediately, but you have to think about it over a planned period of time. And that’s why the book Millionaire Milestones tries to help you diligently save and invest by age, by work experience. So you can eventually get there because there’s a great saying, if the direction is correct, sooner or later you’ll get there. My hope is that people will achieve financial freedom sooner rather than later because we all have a finite amount of time.
Right. So in your book you talk about one thing that I, I found like one, one of my favorite areas was about generational wealth and family. What are we leaving? What are we creating? What is that legacy? And I loved was one property per person. Hmm. So let’s talk about that. Where did, where did this strategy come from? Not a lot of people talk about this.
So any parents out there know that their most prized possession asset, whatever you wanna call it, are their kids, right? We will do anything for our children. We’ll stop smoking, stop drinking, going out, laying at night. We’ll stop eating cheeseburgers. We’ll do anything for our children. This called daddy power, mommy power have children and the money will come. And so our number one responsibility is to provide, and we know that the world is gonna become a more competitive, harsher place to be in the future because of AI technology and globalization. There’s just no down in my mind that it’s gonna be tougher. So the idea is in terms of real estate, because I do believe real estate is the best investment for the average person. You want to get mutual real estate by owning your primary residence because that means you’re going up and down with the market.
You’re not a price taker with ever rising rents. And you’re also benefiting from inflation rent increases and property price appreciation. So the idea is the moment you’re about to have your first child, maybe your wife’s pregnant, your girlfriend’s pregnant, or that year you have your first child, try to search for a property to buy as a rental because by the time your child turns 18, you’ll have 18 years to pay it off by, in 18 years the rental income will likely be much higher thanks to inflation plus. And then you’ll suddenly have an asset not only for yourself, for retirement, to fund your retirement, but also to potentially pay for your child’s college education and the future. And if you don’t happen to need that, then that’s great. You can, you can just save it for yourself or you can save it for them. But having your primary residence and one rental property per child, I think ensures financial stability and freedom in the future.
I resonated with that so much. I, I did that actually, my daughter was, maybe she was like seven or eight years old, we took some of the savings that was in her account and we bought her a property in Birmingham, Alabama. And I mean, it wasn’t a very expensive property and property management and everything in place. And I remember her going to school and telling her friends that she owned a house and the kids That’s awesome. The kids were, yeah, they were like, oh, you’re a liar. You know? And she’s like, no, really I do. And you know, it’s all about also teaching our kids, right? Yes. Because this is what they’re going to inherit. This is we’re building this for them and we want the generational wealth. We don’t want it to stop, you know, at us. Like we built this, we created this. So it’s not only giving to them, but then it’s teaching them, right?
The teaching part is huge because we, instead of just giving our children money, imagine buying a property when they’re young, when they’re born. And then let’s say at age five they under, they understand some things in the world and you take them to your rental property and you go pool the weeds and you go landscaping. And during tenant turnover, you paint the walls and you fix things that are broken over a 15 year period while they’re taking care of this property, they could potentially inherit, they’re gonna be darn more appreciative of the property and the sweat that was, you know, was needed to take care of the property over the years. Versus just saying, here honey, here son, here’s $500,000 or mil, whatever it is. I mean that, that’s, that’s no way to go. But teaching and getting them to have skin in the game is so huge.
Yeah, I agree with that. I, I kind of tend to, maybe this is a little bit controversial, but even with their education, paying for college, ’cause I’ve got kids that are in college and they’re paying for their own college. I’m not paying for that for them because I feel like if you pay, you pay attention. However, I love that.
<Laugh>, however, they have rental properties. And so those are something that I have given to them that is that, you know what I mean? I’m not just giving them everything. I want them to be really into their education. I don’t want them to just go and pick a random major and party and you know, not take it seriously ’cause mom and dad are footing the bill. You know?
Right. I mean, this is definitely one of the major questions and concerns. Fire parents, we call ’em, or financially independent parents who can provide wealth question will they raise spoiled, rotten, entitled children who end up doing nothing with their lives. And I think that’s one of the biggest shames is to take away a child’s ability to learn, earn, and create something for themselves.
Right. Well, if you think about how you got started, most entrepreneurs started somewhere where they saw something bigger and they saw a vision of what the world could be and had to just freaking work their butt off to make that happen. I agree with you. I’ve always <laugh> worried and thought about those same things, is I had that fire under me to make something happen and I want there to be some type of a fire for my kids as well.
Yeah, absolutely. And it’s interesting, I, I grew up in Zambia, Japan, Malaysia, Taiwan, when I was growing up, and I could see the differences between the rich and the poor. And then when I came to the Amer America, Northern Virginia for high school, there was much more homogeneity in terms of socioeconomic wealth. And so when you don’t see that poverty, it might, it might be a shame because you won’t appreciate how good you have it until it’s gone.
Yeah, definitely. So if you don’t mind, I’m gonna take you back to the beginning of your book because there, there was a section that I, I think that the listeners can really find value and obviously they’re gonna have to read your book to really get the value in it. But when we’re setting up our goals and our why, you are very specific. You’re like, Hey, don’t just create a goal that’s very broad. You’re like, I want a, a $300,000 house in five years, a three bedroom house. You know, you’re very, very specific. So can you walk us through again, I love the mindset part of it so much and I love goal setting so much. I’m a firm, firm believer in all of that. So can you walk the listener through goal setting?
Well, money is just funny. Money to me. There’s really, you know, stocks, it’s just numbers on a screen. They don’t really matter unless you have a specific purpose for why you’re saving and why you’re investing. Once you list those specific purposes, ah, it is so much easier to save. It’s so much easier to come up with a risk appropriate investment game plan. It’s so much easier to plan out your future. Otherwise we’re just walking zombies. I feel doing the same old thing at work and not feeling very inspired. So in terms of goal setting, it’s really, we know that the median life expectancy is about 80, right? 78 to 82. It’s kind of sad, but that’s the reality. And so we have to really goal set by time because we’re always running outta time. And so in your, let’s say in your teenage years, maybe you want to goal set to be able to pay 20% or 50% of your college tuition.
When you’re in college, your goal set is to try to meet someone by the age of 26. So you can get married by 30, so you can have a family, and then maybe your other goal is to have a house by age 35. And you need to have these specific timeline goals because biology is not gonna wait for you in terms of making enough money to have a child or have a home. And your life is not gonna wait for you to be able to do the things that you want. And so to be very specific by age is very important. And I think a lot of people will look at these milestone charts, you know, how much you should have saved in your 401k or net worth by age 25, 35. And sometimes they might be like, whoa, oh, I’m way far behind. But that’s actually great because it hopefully it will shock you and motivate you to catching up because at the end of the day, nobody really cares about your wellbeing except for you. And time waits for nobody.
That’s so true. I mean, I, I don’t think that I was ready to have my first child, like in all accounts. I mean, I was doing the right things and we had some money and having that first child sure. Kicked our butt because it made us go, wow, life is serious. We have to get on it now. We can’t just mess around. Like, we’ve gotta take our job seriously. We’ve gotta save like all these things. Like that actually is what really, you know, it wasn’t just us anymore <laugh>.
Right. You know? Yeah. When it’s, when it’s just you, after you have a child, when you look back, when you don’t have children, you’re like, wow, life was actually pretty easy. But wow, it could have been much more specific and plan. You know, one of my biggest regrets is having children late. Our first son came in 2017 when I was 30, almost 40. And that’s really sad because on the backend, I won’t be there in his life as long as I wanted to. And the reason why I had children late was because somebody, when I was working at Goldman Sachs, he was a wealthy kid who went to Yale, very wealthy parents. He said, Sam, my goal is to have a $1 million net worth before I have my first child. And at 23 I was like, okay, that sounds like a reasonable goal, why not?
Right? And I had that stuck in my head all the way until about 32. So 10 years after college. And as a result, I focused way more on making money, saving money, investing, you know, which is okay, but way less on family planning and being a father. And so I regret that. I, I wish someone told me, you don’t need a million dollar net worth to have children even in expensive New York City or San Francisco. You need to be more balanced in your planning and have more specific life in family goals. Because at the end of the day, what’s gonna make you happiest? What’s gonna make you happiest? Are your friends and family in your community? Not so much the money.
And you know what, and that kind of wraps up my takeaways from your book. We kind of start off with why and goal setting. And then we talk about, well, you talk about <laugh>, about the why and then embracing saving and investing and then building your net worth and then continuing to grow it through entrepreneurship, through real estate, how, however you’re gonna do it. And then you get into the lifestyle of it, which I love. I, I love everything that you’ve talked about be where the money is, make the most of your family and marriage, and then creating that legacy and that wealth. I’m so excited for all of our listeners to go out and get your book. My key takeaway from it is, real wealth is measured in freedom and time, not just money. And so do you have anything else that you would love to mention to our listeners out there? Or did I get your recap of this book correct. I mean, that’s, that was my personal takeaway.
That’s great. Everybody will have their own takeaway. Yes. My, my number one goal is for readers to achieve financial freedom sooner rather than later so they can do more of what they want in their one and only lives. It really is something that, you know, when I look back upon in my twenties and thirties, I wish I worked even harder. I wish I took even more risks because over time the economy, your investments generally go up. Anybody who bought the dip over the past, let’s say 30 years is doing well. If they still held on, you know, now it’s a little bit dicey in 2025, but I, I’m pretty certain in 10 years you’re gonna look back today and say, I wish I took that risk. I wish I bought that index stock or that stock and I wish I went for it. Time goes by very quickly.
It accelerates as you get older. And the one of the worst things that we want to prevent ourselves from experiencing is that feeling of regret. I think we really need to go through that regret minimization framework where we compare the two outcomes. You know, if you don’t try, the answer is no, succeed if you try, the answers are no succeed or you succeed. So you might as well just try <laugh>. You might as well try and you might as well go for it. And while you’re doing so and you’re building wealth and you’re building connections and friendships, try to give something back. Because at the end of your life, I feel one of the most rewarding things is to share the knowledge and wisdom and teach others how to build that wealth and a better life. So I’m really excited about Millionaire Milestones.
That was so clip it and make a soundbite out of that for a reminder. Kind of put that in our phones, like a daily mantra just to listen to. I, I love so much of that. Thank you so much. I appreciate your time today and again, I am so excited for our listeners to go out and get the book. I definitely am honored that I was able to read it in advance so that we can have this conversation. And yeah, thank you again.
Thanks so much, Melissa, for having me on.
That Is it for today’s episode with Melissa and Sam. If you haven’t subscribed to the show, please do. You know, I appreciate you listening. If you haven’t subscribed to the show, please do so. It only takes you a few seconds to click the subscribe button. Thank you for your ratings and reviews. Greatly appreciate it. If you need to get in touch with my team, just reach us at noradarealestate.com and we’re here to help you. So thank you for listening. We’ll see you all on our next episode.
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