Sam shares how he reached financial freedom through an aggressive savings and investment plan and his tried-and-tested tips for retiring early.
Philipp: Welcome to another episode of, In Your Best Interest, your personal finance podcast. I'm your host Philipp Muedder.
Sam Dogan runs Financial Samurai, one of the largest independent personal finance sites that gets more than a million visitors a month.
Before Financial Samurai, Sam spent 13 years working at two major finance companies, and earned his B.A. from William and Mary and his MBA from UC Berkeley.
He left corporate America in 2012 with the help of his retirement income that now generates roughly $300,000 passively.
Today, he enjoys being a stay-at-home dad to his two young children.
Sam, I'm very excited actually to have you on the podcast today. I've been reading your blog for the last eight-plus years. Thank you for joining us.
Sam: Thanks for having me.
Philipp: Yes, it's really great. I think you impacted a lot of people's lives, and this being a personal finance podcast, I think our listeners are going to be super excited to learn how you have done throughout your personal finance journey, and kind of like what you can share with them as well.
But I do want to start off because by reading your blog for so long already, I know you have quite some ties also to Southeast Asia, where we are located. I know we have listeners from all over. But our core audience is in Southeast Asia. So do you mind sharing a little bit of what your connection is with Southeast Asia?
Sam: Yes, I lived in Kuala Lumpur, Malaysia, [02:00] when I was in middle school, and I attended the International School of Kuala Lumpur. My parents were in the US Foreign Service. So it was a great life from when I was born until age 13 when I moved back to America, at age 14. I lived overseas for a while. So in my mind, KL and Singapore have the best food in the world, I always miss the food. I don't understand why more entrepreneurs don't try to bring Singaporean or Malaysian cuisine to America because it's the best.
Philipp: It's super good. I actually had the same discussion with my wife just not too long ago because I'm currently in the US, but we have lived the last three and a half years over in Singapore, and we just had the same discussion. Hey, we haven't even had very good Singaporean or even also Malaysian food since we moved back last year, right? It's really difficult to find, but it's so good, I do agree.
Philipp: Yes, this is great. So this is a good connection for all of our listeners. So I suggest everyone check out your blog as well, there's some good stories in there. And we will link a lot of the articles that we mentioned here today as well so that they can have a read on those.
But Sam, obviously, this being a personal finance podcast, we have a lot of other guests also talking about financial freedom and kind of becoming financially independent. Your journey is super interesting; I mentioned in your introduction that you spent 13 years working at major investment banks, and then you decided to leave corporate America in 2012 because you started to generate enough passive income, right?
That's obviously a big dream for a lot of people. So a couple of questions [04:00] before we get into that pre-retirement checklist that you have for everyone is, what does retirement actually mean to you nowadays? Versus do you call it still retirement to yourself, or is it more financial freedom that you like to associate with? What's your thoughts around that topic?
Sam: I believe it's more financial freedom. My motto is achieving financial freedom sooner rather than later. And so the way it started was back in 1999 when I had my first job out of college. I was working on Wall Street; I was at Goldman Sachs.
45 Wall Street - their equities headquarters - and I had to get in at 5.30 am. And after about a month of getting in at 5.30 am and then leaving after 7 pm, I just told myself I just couldn't take it anymore; there's like no way I could last for so long.
My parents were in the Foreign Service for 25 plus years; I think 30 years for my father. And I said there's no way I could sustain myself that way. So having a difficult job right out of college where you work 70 plus hours a week was my catalyst to try to achieve financial freedom sooner.
And so I decided after month one to try to save as much money as possible. Basically, I saved every other paycheck with the goal and the hopes that I would leave work by 40. I thought age 40 was a great time to leave because it would be 18 years of work, and then I'd still be young enough to do other things if I wanted to.
Philipp: That's a great story. I like that you said you started saving aggressively from your first job, right? I think… not in today's world, but in general, a lot of people don't put that first when they get their first paycheck, right?
So a lot of people want to spend. You have your friends having started to make income, [06:00] going out. So how was that for you? Like how did you cope with that, right? Yes, you were working quite a lot, so maybe there was not even time to go out after work. But yes, how did you develop that mindset to do that, getting that high savings rate up?
Sam: Well, the pain of work was so great that savings alleviated that pain. When you're working 70 plus hours a week, you're not at home as much. So I lived in a studio with my friend for the first year, and then a studio plus an alcove with no windows with another friend for the next year to save money on living expenses.
So it felt good; the more pain you go through at work, the more suffering, the easier it is to save because every single dollar you contribute is one step closer to financial freedom. So I would caution people who get out of college or get out of high school and start working at a really 9 to 5 easy job, hour lunch break, chatting around the water cooler or virtually whatnot.
That's nice, but I don't think it's going to motivate people to really save and invest aggressively.
And that might be fine, but the problem is, I think like anything, if you do anything for 10 years in a row, you're going to get sick and tired of it. I've noticed since Financial Samurai has been around since 2009 that a lot of people wake up 10 plus years later and wonder where all their money went because they didn't have the discipline to save and invest.
It's an analogy that I use when going to the dentist; if you've ever had braces if there's no pain in your teeth, nothing's happening with your teeth, right? So if the amount of money you're saving each month doesn't hurt a little bit, you're not saving enough.
Philipp: Yes, it's a good analogy. I think you made a good point. [08:00] I think a lot of people wake up 10 years later; then they're unhappy with their job because they weren't at the beginning, but they didn't save, and now they don't have that financial freedom option, right?
To take a time off or pursue whatever they want to instead. So I think great stories, great tidbits of information for our audience.
Then we get to 2012, you start to become retired, right? I don't want to give away too much information because we are going to talk about the checklist again later on.
But this is the first time you officially retired, right? So how did you decide that was the right time at that moment? And again, how did you over that time? You invested, of course, but that's an impressive amount of passive income, right? Did you just get that from investments, or what was that journey like?
Sam: So in 2012, it was just 3 years before the worst of the financial crisis in July 2009. So that was a scary period because I worked in finance during the financial crisis. So we went through 7 rounds of layoffs, everybody was, so many people I knew were getting blown out of the water.
And it was no longer fun working in finance; you just became the bad guy, even if you had nothing to do with the US housing market. So it was a scary time, but I held on; I kept on investing.
And then in 2011, well in 2009, I started Financial Samurai as an outlet. It was like a cathartic way to make sense of all the chaos and fear that was happening in the global financial markets. So what I found was I really enjoyed writing and communicating and connecting with other people online with similar goals and ideologies.
So I just kept writing, and I spent probably 3 hours on average after work or before work writing, writing, writing until in 2011 [10:00] it started making a couple of thousand dollars a month.
It's like something I was thinking, wow, this is pretty cool. Then so, in October 2011, I was in Santorini, Greece. By that time, I was already kind of checking out from the finance industry. I was taking six weeks of vacation every year, which is what I was allowed to as a director in finance.
Philipp: Allowed, but probably not looked up to, right?
Sam: Yes, it was frowned upon, but I just did it anyway. So I was in Santorini, I was hiking the big cliffs. And then I got to this bar. It was a 78-degree warm day, and then I got an email through Wi-Fi, which was kind of special back then with my phone, about an advertiser who wanted to advertise on Financial Samurai for $1,000 if I put up a link.
I said, sure, why not.
So I put the link in five minutes, ten minutes he sent over $1,000 via PayPal within 30 minutes after I put up the link. I was thinking to myself, wow, I'm so rich now, I can't believe I made $1,000 in under 30 minutes.
So let me go order another Mythos beer that costs $8 at the time, which I thought was like give me another one. So that was like my a-ha moment where I thought, what maybe I could do something else after finance.
And when I left in 2012, I had about $80,000 a year in passive income. And $80,000 was enough for me to survive comfortably because my wife, who was 3 years younger than me, still was working.
So I said, let me try first and see how this thing goes, and let me see if I can work on Financial Samurai in my free time, and we'll go from there. But the key catalyst for me to leave was the severance package. The severance package is what gave me the courage to leave because it was a six-figure severance package.
[12:00] It was allowing me to keep all of my deferred compensation, my stock compensation and my cash grants. So it was really the catalyst - the severance package - if you're going to retire early or quit your job and not go back or take a break, you want to try to negotiate a severance. Don't quit because if you quit, you just get left with nothing.
Philipp: Yes, that's a really good point. I know we can talk probably a few hours about the whole severance package. But I think you have an eBook on this topic, right? If people are interested.
Sam: Yes, I just updated for 2021. A lot of good strategies and a lot of people sharing their stories. It's a no-brainer. You have no downside to try to negotiate a severance if you're going to quit anyway.
I think people are just a little bit too fearful, they don't like confrontation, and they always let the big guy beat them up. So I'm trying to encourage the little guy to fight for themselves.
Philipp: I think this is a huge topic in and of itself. So we'll definitely put the link in the show notes for all of our listeners, so if they're interested in that, they can learn more there from your eBook.
Just maybe in like a 30 second or a minute answer, just after the financial crisis, so most people in finance are happy to have a job, right? I was in that space as well. I graduated actually in ‘08, right?
So not a good time to graduate in finance. But what was that conversation like to go to your company where they probably think, oh, everyone should be happy to have a job. To then get a severance was a pretty gutsy move one, but like you said, there was nothing to lose, right? That they actually did it.
Sam: Well, in 2012, it was still uncertain, but it was much better than 2009. So in 2009, it would have been much scarier; I didn't want to do it. [14:00] Because I only had 10 years of work experience and savings and investing, and my net worth went down like 35% in 6 months.
So that was more fearful. But in 2012, I felt like, okay; things are kind of back a little bit. Let's give it a go; at 34 years old, it was now or never to try to do something on my own. I've always wanted to do something entrepreneurial on my own. And I was also sick and tired of finance; I did 13 years, I was just tired.
I needed a break; I wanted a break. And in retrospect, a sabbatical would have been nice, but they didn't encourage sabbaticals either. So when I talked about getting that severance package, it was awesome.
It was a six-figure severance check, and I had deferred compensation that paid out from 2012 until 2017, five years in a row of really good deferred income.
Philipp: Which is super nice if you didn't have to touch your investments in the meantime, right? So you could let those grow, so that's awesome.
Sam: Yes. I literally I got the severance check which was one part of the severance package, and I invested 100% of it into the S&P500, and I just said, let's go, it was like a bonus. It was like winning the lottery a little bit.
Philipp: Yes, super cool. Like I said, if people are wanting to find out more, we'll put those links in the show notes. I think it's a super nice story, and they can read a lot about it also on your different blog articles about it.
So then fast forward to 2012, you leave corporate America, you really hunker down on growing Financial Samurai.
Why now bringing out a checklist for pre-retirement, and talking about retirement again, because it seems that you have retired, but Financial Samurai seems like it took over your life as a full-time job, is that correct?
Sam: So not entirely correct, it was something that I loved to do in 2012/2013. So I said I consider myself [16:00] retired for about one year, and then after in 2013/2014, I decided this was ridiculous; I don't feel retired, I'm too young to be retired.
So I said I no longer was retired after someone would ask what I'd do. I said I was a freelancer. I did some consulting part-time for a couple of startups. I wrote on Financial Samurai, so I would say I was a writer or blogger.
And then, I pursued my dream of being a teacher, and I decided to be a high school tennis teacher for 3 years. It was only 3 months a year, but it was very rewarding. And then I kind of started fading again, but then when my son was born in 2017, I started getting amped up again to try to make a little bit more money.
Because healthcare is expensive in America, and college tuition is expensive in America. So in 2018, I slowly decided to try to make more money online or freelance consulting.
And it's something interesting, there's like a saying that says have children, and the money will come, and I thought I had enough money, but it was something about the birth of my son in 2017 that reignited my desire to make more money, to build more passive income, to take care of my family.
I think this has to be a genetic predisposition of all parents to try to do more to support the family. So I started doing a little bit more, and then when the pandemic hit in March 2020, and the lockdowns hit, I just said, well, if the government is going to lock me down, and there's less fun things to do, then I'm going to focus a lot on trying to make money online.
And so that's what I've been doing. I've been waking up by 3 am, 4 am working 3 to 4 hours before my kids get up at 8am - 8.30am. And then spending anywhere from [18:00] 4 to 8 hours a day with them.
And then afterwards, trying to update Financial Samurai and do all that stuff. So essentially, I went from working leisurely, like 20 hours a week, with Financial Samurai creative work. Writing, connecting and all that to then changing it to more like work, work. Which probably after 6 months didn't feel good at all; it felt bad actually, trying to make more money.
It just felt like, oh man, I'm back to the grind. I've got meetings, calls. I've got deliverables, and all that, I've got to negotiate business development deals. So I have a goal, June 15th, 2021, that's when California opens up fully; that's what the governor said.
That's going to be my 1-month sabbatical. August 25th, 2021 that's when my son finally goes to preschool. We pulled him out from preschool, and so he has been in home learning for the past year and a quarter.
That's going to be a time where we're really going to kick back because we're going to get 6 more hours of free time. Then I think by February, around February 2022, there's going to be herd immunity. And that's when it's back to retirement life, baby.
Philipp: I love this plan.
Philipp: It's really good to hear, so you really have a timeline on exact dates, right? I think that's where you want to spend the next few minutes of the podcast, is kind of that pre-retirement checklist that you created.
Maybe it could be even like a financial freedom checklist almost, right? If you want to call it that for the audience. But where did you start out on that? So why do you even think you should have that checklist?
Sam: Well, if you think about it - so one of the worst things I think people can feel is regret. The regret of not [20:00] doing something when they could have. That's something that has always driven me to try many things.
But eventually, you're going to get wise enough and old enough where you will be able to minimise your regret; starting Financial Samurai was using the regret minimisation framework.
And since what I regret when I'm 70, not having tried something on my own and the answer is absolutely. If you think about packing for a long trip, an international trip, it's easy to forget something you may end up regretting not bringing without a checklist.
So this pre-retirement checklist is round two because I already went through that in 2011/2012. And that was the first time around, and I missed on with several things. So round two is my way of being wiser and helping other people who want to retire early or just take a break or get out.
So for me, as I plan this, it's so important now, like before I had kids, it was just me and my wife, it was really easy to live a comfortable life. But when you have young children under 5 years old, under 10 years old, it's so important to get your finances right and to minimise the regret.
So what I realised - one, was that my exposure to risk assets, such as stocks, real estate and alternative investments, was very high. About 88% of my net worth was exposed to risk assets, which doesn't make sense if I'm going to be taking it down a notch within 12 months.
So the first item on the pre-retirement checklist is to make sure you have the proper asset allocation. Just because I'm 43 years old today doesn't mean I should be investing all-in 88% of my net worth into risk assets.
Instead, maybe I should be thinking more like a traditional retiree who's retiring at maybe 62 to 65 or 70, [22:00] and I should bring down that risk.
Philipp: I think that's a good point you're making, right? Because a lot of times nowadays, but bond yields are very low across the world.
So people are putting more towards risky assets even closer to retirement, or they're afraid to do it, right? And so they're sitting in cash, which is also not helping them at all. So yes, how do you think about that when you look at your asset allocation?
Sam: Well, I have an asset allocation model that I go through based on the type of person you are and the age.
So for me, I've been strongly considering taking down that risk exposure from about 88% closer to about 70% or 60%. And so one of the things that people should think about is how much wealthier they have gotten, thanks to the pandemic.
I call this the overages; I call this the boot. So let's say the stock market generates 10% on average, would have generated 10% in 2020, and 10% in 2021. Well, any returns over that 10% is called the boot, and that boot is something that you gain thanks to the pandemic and thanks just massive stimulus spending by various central banks around the world.
So one of the things you want to think about, and this is not just for retirement, is just thinking about living a better life. So for most people, the pandemic has decreased the quality of life. You can use your money, your extra money, the boot, to spend on a better quality of life.
So whether that's travel, going first class, buying new shoes, eating toro sashimi, whatever it is.
But really, people have to think even harder about how to asset allocate and how to utilise their money. Because I'm sure most people are thinking - I'm not going to, I realise [24:00] that life is precious; I don't want to work at a stupid job that does nothing and gives me no purpose. I want to use my money, my savings, and my life for a better life going forward.
Philipp: Yes, I think those are great thoughts; yes really appreciate it.
Sam: So other things on the pre-retirement checklist, for example, number two on my list, is make sure you've done everything you've wanted to do.
So again, we're trying to minimise regret. So if you're working, make sure that you ask your boss if you want to try to do this project, or maybe you want to relocate to some other part of the world.
If you can cross those to-do lists off your career list, once you retire or take a long break, you won't have that kind of regret.
The other item is living off your passive investment income. You want to try to do that for 3 to 6 months at least, so see if you can live off your investments. Whether it's the dividends that are being paid out by your stocks or the coupon payments by your bonds, or the distributions by your real estate, or your rental income.
Or whether it's touching principal, withdrawing principal, which is very hard to do for super-savers and long-term savers to do. But you gotta try.
Philipp: It's probably one of the hardest things for people to do. Everyone who has saved a lot their whole life, now taking it back out, is very scary.
Sam: Yes, it's uncomfortable. Which is why I think you'll see a lot of people in the FIRE community not do that.
I haven't done that, I have left 100% of everything in the markets or whatever since 2012, and I've tried to generate supplemental retirement income in a way that I enjoy doing, right? And that's Financial Samurai.
And then another thing is, obviously, I think you need to have a specific retirement date in mind. Because if you don't have a date, you circle on your calendar, you're just going to kick the can down the road, [26:00] and it's going to push things down.
So you want to have a little bit of discipline, actually a lot of discipline, so you do everything you want to do. Whether it's savings, relocating, asking your boss, whatever it is before you actually make the move.
The other thing is you want to be clear on what you want to do next. You want to retire to something, not away from something. And so everybody listening has to ask themselves what would you be doing with an extra 8 hours of your day.
In my case, that was writing for 2 to 3 hours a day, playing tennis and softball, sometimes golf for 2 to 5 hours every other day. And then now, spending a lot of time with my children. I was doing some research, and it says the average American mother spends 120 minutes a day with their child. And the average American father spends about 80 to 90 minutes.
Philipp: That's crazy numbers.
Sam: It's so low, it's kind of sad, and it makes me wonder if we all spent more time with our children, maybe we'd have better relationships with our children. Maybe we had better-adjusted people in society. Who knows? But we're trying; my wife and I are trying.
Philipp: I think this is so low like I never looked at those numbers. But that seems so low. Just me growing up in Germany, I think I definitely saw my parents more than that I think, to remember, but who knows at the end. But yes, that's a very scary low number.
Sam: Ask your parents.
Philipp: Yes, I should actually ask them, even though my dad did work quite a lot, but I know we always had dinners at night, all of us together. Weekends and yes, and definitely my mom was stay-at-home at the time, so I saw her every day after school, right? But yes, that's a scary low number if you put it like that.
Sam: Yes. There's several more things we’ll just quickly touch upon.
Sam: You should refinance all your debt before leaving your day job. [28:00] Because once you leave your job, you're dead to banks and lenders. They won't want to trust you or lend you any money unless you have 2 to 3 years' worth of freelance experience, like a steady amount of income as a freelancer.
The other point, make sure you pay all your outstanding corporate debt. Whether it's your corporate card or whether it's debt to people that have helped you out in the past. And you also want to have closure with all your outstanding issues.
So over the course of the years of competitive work, everybody's like grinding to try to climb up the corporate ladder. You're probably going to step on some people's toes or make some enemies. It actually feels really great to try to make amends somehow, to have that closure. Closure is so important.
And then finally, I think you need to, and it's along the lines of retiring to something, is to make sure you and your life partner are clear on what you want to do, are at least on the same page, and have some of your own lives to live, right? Because if you're going to go from spending 3 to 4 hours a day with your life partner to 12 plus hours a day, it's going to be very difficult for most people.
Philipp: Yes, super difficult. Yes, thank you for sharing that checklist with us. I think this will be super helpful for any of our listeners who are also thinking about this.
Like you mentioned before, I actually did quite a bit of financial planning the last few weeks with clients, and everyone feels a little bit burned out, right? The last year really had a lasting impact on people and well they're burned out from work, [29:58] they’re burned out from COVID, and they don't really see a way out yet.
[30:00] Because I think in the U.S where we are right now, it seems like there is some light at the end of the tunnel. But in some other places, it seems still very far away from that.
So I think this is a great checklist; I think people can start working on it. It's not going to happen overnight if they haven't been planning for this a long time. So I think a great start for them that you shared with them, so thank you, Sam, for that.
Sam: No problem, yes. The ideal amount of time before you retire is probably around 1 or 2 years. You can start the checklist, start the planning 1 to 2 years ahead of time. And one of the keys I think to becoming wealthy is to successfully forecast your misery or the future.
So a lot of people I've talked to who start a new job, or they're young, they feel so happy, right? They're like, oh, excitement times; they think everything is going to be lollipops and rainbows.
But if you can successfully forecast your misery in terms of when you think you're no longer going to be happy doing something, you're going to take those steps to be able to prepare for that, better prepare for that, so that as soon as you start feeling that decline, you can make a rational and calculated change.
Philipp: Yes, good tip as well, very good tip as well. If you would leave the audience with one thing that got the best out of you to get that early retirement lifestyle.
Was it aggressive savings that is the best tip? Is it you have to invest as well? But if you're scared of investing, but you're saving aggressively. What combination would you leave the audience with that they should focus on if they wanted to be on their financial freedom journey?
Sam: I think you've got to figure out what you want and go after it with abandonment. It's the thing where I notice people like to make fun of planners, super planners.
[32:00] I get made fun of all the time about planning; let me give you an example. So one of the reasons why I wanted to be a high school tennis teacher. Not only because I played tennis, and I always wanted to be a teacher.
But because I had a new son in 2017, my son was born in 2017. So I wanted to understand what it's like to teach and be around teenage boys because I was coaching 14 to 18-year-olds. I wanted to see is it really that much of a disaster? Or that difficult?
Philipp: Were we that bad back in the days, right?
Sam: Yes, because that's what everybody says. So I wanted to understand that, so I could be better prepared for when my son turns 14 or 13 at that time. So to some people, they said Sam, that's ridiculous; why are you preparing 13 to 14 years out?
And I'm thinking to myself, why not? Why not prepare? Preparing is free, and it can be fun, and you can actually make some money as well.
So don't let anybody try to make fun of you or put you down for over-preparing. You can't over-prepare, you can prepare, and you can run your scenario analysis, and I think that's a great thing.
So prepare as much as you can, and you really got to go out and want it with your one and only life. There's no rewind button, so you've got to take ownership. Everything is rational, so whatever happens to you, you shouldn't blame other things; you should focus on how you can get better and control what you can control.
Philipp: Yes, super nice final thoughts. And Sam pointed out quite frankly, you can only control what you can control.
I think the savings rate is one thing that you can control; I always underscore, underline for people. That's the one thing you can control in investments is your savings rate.
So keep doing that, and thank you again so much, Sam. [34:00] I'll be able to put a few links to your articles; I'll definitely put my top five articles that I like into the show notes below.
So if you want to learn more about those topics that I like, feel free to check them out.
Also, we'll put the link to the negotiating a severance package eBook into the show notes as well, if you're interested in that. Anything else, Sam, where can people find you across different channels? Anything you want to share with them?
Sam: Yes. You can always go to FinancialSamurai.com. I read pretty much all the comments, and I respond to any comment that needs responding to.
I'm working actually on another book with Penguin Random House; it should be out in 2022. It's gonna be a traditionally published book, so that'll be fun. Look out for that, maybe in the second half of 2022.
I'm on Twitter sometimes at @financialsamura without the “I” because there was not enough space to put in the “I”. But I try to minimise my time on social media because I just think, man, big media and social media is not really good for your mental health.
Philipp: No. Then you just keep starting fighting with people, and then you get in a bad mood, right?
Sam: Yes. I mean it's kind of crazy, and one of the things scientists have been studying is the negative causes of extended isolation, and it causes people to be unhappy and more violent.
So just be aware that if there's someone who's super moody or whatever, maybe be more empathetic to them. And maybe check in on people who are isolated, like maybe the parents or whatever.
I'm really going to be spending a lot more time trying to spend my boot, as I mentioned before. Try to stay healthy, spend time with children, our children.
Maybe other children like foster children. I think we really need to heal now, and we really need to live our lives to the fullest, and that's what I'm excited to do.
Philipp: [36:00] Awesome. Well, thank you so much, Sam, for your time; we really appreciate it. Hopefully, when you're about to publish your new book, maybe we can have you on again and continue that discussion. Because I think there's still a lot of topics that I would love to touch on with you. So thank you again for your time.
Sam: Sure, thanks a lot.
In this episode, Sam Dogen joins Phillip to talk about how he reached financial freedom and what’s on his retirement checklist. He also shares why he started Financial Samurai and what his plans are for the post-pandemic world.
For past guests, visit stashaway.com/podcast
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