In Search Of FIRE: Financial Samurai Retirement Portfolio Review

In Search Of FIRE: Financial Samurai Retirement Portfolio Overview
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I'm always in search of FIRE (Financial Independence Retire Early). Even though I left work in 2012, it's now becoming more of a struggle to stay retired now that I have two kids.

It hit me the other day that I've got to get my act together if I plan to retire a second time soon. But retiring a second time just doesn't seem as feasible given the soaring cost of college and health care.

My First Re-Retirement Attempt

The first attempt at retirement lasted for just under a year until I started feeling too sheepish telling anyone I was retired at 34. Although my retirement portfolio was generating about $80,000 a year in passive income at the time, I started itching for more.

Seven years later, I was running out of steam. I conducted multiple calls with boutique investment banks, private equity shops, and larger media companies on the potential sale of Financial Samurai after its 10-year anniversary mark in July 2019. However, I feared I would regret selling my online business, so I didn't.

More Strategies To Boost The Family's Finances

I've also tentatively convinced my wife to go back to work once our son turns two years and five months old this Fall. Spending 29 months as a stay at home parent should be long enough to feel like a parent did the best he or she could without feeling too guilty chasing money instead. But we shall see when the time comes.

The final thing I need to do is make sure our after-tax retirement portfolios are generating enough income to cover our desired lifestyle just in case Financial Samurai is sold and my wife can't get a reasonable job in a field of interest.

I feel blessed to be able to do all the things I love since leaving full-time work in 2012 – coaching high school tennis for the past three years, writing almost daily on Financial Samurai, traveling around the world, and spending time being a stay at home dad since early 2017.

The Second Attempt To Re-Retire Probably Isn't Going To Happen

But all good things come to an end. We must frequently adjust in order to keep the good times going for long. Going back to work may seem like a failure. But I had over a decade off work during the prime of my life.

With college for two potentially costing $1.5 million all-in, in the year 2037, making more money again sounds like a good idea. Paying for college is a daunting task and I can’t rely on scholarships.

In Search Of FIRE: How To Build A Healthy Retirement Portfolio

Before discussing FIRE (Financial Independence Retire Early) and my retirement portfolio's latest income figures, I'd like to share five tips for everyone to follow to build their own healthy retirement portfolio.

1) Save until it hurts each month.

Most people think that saving for retirement in their 401(k) or IRA is enough, but it is not. In order to have the optionality of retiring early or ensuring a healthy retirement at a more traditional retirement age, it's important to max out your 401(k) while also contributing at least 20% of your after-401(k), after-tax income to an after-tax investment portfolio.

The after-tax retirement portfolio really is the key to early retirement since most people can't access their pre-tax retirement accounts without a 10% penalty before age 59.5.

2) Focus on income producing assets.

After you've had your fill of high octane growth stocks as a young person to build your capital, it's time to focus on income producing assets as you get closer to retirement. Dividend generating stocks, certificates of deposit, municipal bonds, government treasury bonds, corporate bonds, and real estate should all be considered in your retirement portfolio.

When I was younger, my favorite type of semi-passive income was rental property income because it was a tangible asset that provided reliable income. As I grew older, my interest in rental property waned because I no longer had the patience and time to deal with maintenance issues and tenants. Instead, my interest in REITs and real estate crowdfunding grew since the income generated is 100% passive.

3) Start as soon as possible.

Building a large enough early retirement portfolio takes a tremendously long time largely due to declining interest rates since the late 1980s. Gone are the days of making a 5%+ return on a short-term CD or savings account. You need to save early and often to make compounding work most for you.

I knew I didn't want to work 70 hours a week in finance forever. As a result, I started saving every other paycheck and 100% of my bonus starting my first year out of college in 1999. By the time 2012 rolled around, I was earning enough passive income to negotiate a severance and retire early.

4) Calculate how much retirement income you need.

It's important to have a retirement income goal. Otherwise, it's too easy to lose motivation and focus. A good goal is to try and generate retirement income to cover all basic living expenses such as food, shelter, transportation, and clothing. Once you hit that goal, focus on covering your wants.

If your annual expense number is $50,000, divide that figure by your expected rate of return or comfortable withdrawal rate to see how much capital you will need to save. If you expect to earn a 4% rate of return, then you would need at least a $1,250,000 after-tax retirement portfolio, and closer to $1,500,000 due to taxes.

5) Make sure you are properly diversified.

The first rule of financial independence is to never lose money. We saw a lost decade for tech stocks between 2000 – 2010 after the first dotcom bust. For NASDAQ investors, it took 13 years to get back to even. Then we experienced a housing bust of epic proportions between 2007 – 2010. Then the March 2020 crash followed by the 2022 bear market!

You always want to be moving forward on your journey to financial independence. The closer you are to retiring, the more conservative your investments should be. Please do not confuse brains with a bull market.

Financial Samurai Retirement Portfolio Review

Since retiring the first time around in 2012, I have yet to stress test my after-tax retirement portfolios because I received a severance that paid out enough money to live for five years. If you are in search of FIRE, then doing an annual portfolio review is a must.

While I was living off my severance income, my wife worked until she negotiated her own severance at the end of 2014. She is three years younger than me. Having her work and provide healthcare was very comforting and allowed me to reinvest 100% of our after-tax retirement portfolio income.

Then once both of us weren't working full-time jobs in 2015, Financial Samurai started generating a livable income stream as well. This positive sequence of events is why planning is so important. It's frankly why quitting your job to retire early is a suboptimal move.

Ideally, we want to live on around $15,000 – $18,000 a month in after-tax income to live our best lives while raising one or two children in expensive San Francisco or Honolulu. Using a 28% effective tax rate, we're talking a target $250,000 – $300,000 a year in annual gross retirement income.

Financial Samurai 2019 Passive Income

For reference, here was my passive income back in 2019. Then I'll share what my passive income is now in 2023.

In Search Of FIRE: Financial Samurai Retirement Portfolio Review 2019

As you can see from the chart, we generate about $16,300 a month in after-tax retirement income if we use a 20% effective tax rate. The effective tax rate for investment income is lower than W2 wage income. Something to think about when forecasting your own retirement income needs from investments.

$16,300 a month or $195,600 a year in after-tax retirement income should be more than enough to provide for our current family of three as our all-in housing cost is less than $6,000 a month. Once all our housing cost is covered, our costs for food, transportation, and everything else aren't too bad.

$16,300 a month will also allow us to continue saving at least 30% a month for a rainy day (~$5,000). Because we've been in the habit of saving at least 50% of our after-tax income since graduating from college in 1999 and 2001, respectively, it would feel foreign to not continue saving in retirement.

Upcoming Costs In Retirement

The main anticipated increase in cost is preschool tuition starting this Fall at $1,800 a month. The other potential increase in cost is if we are blessed with another child.

If we stay in San Francisco long term, our goal is to send our boy to public school after preschool if he can win the SF public school lottery system. If our son does not get into a reputable public school near by, then we'll be forced to spend about $3,000 a month for elementary school and likely $5,000 a month for high school when the time comes.

These potential grade school tuition costs are the main reason why I'm striving towards $18,000 a month in after-tax retirement income, or ~$2,000 a month higher than current levels. I've got three years left to make this goal a reality.

Below is an analysis of the major retirement income categories in search of FIRE.

Risk-Free Savings: $1,045/month (5% of total)

I love risk-free savings, especially after the Federal Reserve hiked interest rates multiple times since the end of 2022. It’s easier to generate passive income in a higher interest rate environment. That’s the one saving grace of the Fed rate hikes.

To be able to earn risk-free money after making massive gains in the stock market and real estate market since 2009 sparks joy! Gone are the days of pitiful 0.1% savings interest rates.

My target is to always have between 5% – 10% of my retirement income and net worth in risk-free investments. You just never know what might happen in the future.

Stocks & Bonds: $7,560/month (37%)

After a tremendous rebound in the stock market in 2019, 2020, and 2021, I decided to asset allocate more towards 3-month treasuries in my main House Fund portfolio.

As of now, my House Fund portfolio is roughly 20%/80% stocks/bonds because my plan is to buy another property within the next 6-12 months.

The House Fund portfolio had a nauseating $400,000 swing (-13%, then +23% so far) and I want to ensure that I protect the principal going forward. My other main public investment portfolio is closer to 60% stocks / 40% bonds. I plan to gradually shift the weighting closer to 50%/50%.

Below is my public stock and bond portfolio performance +9.2% vs. the S&P 500 +15.9% year-to-date according to Empower's performance tracker. With the income from my existing bond holdings, I should have relatively no problem closing out a 10-11% total return for the year.

Financial Samurai YTD 2019 stock and bond performance

As I edge closer towards retirement, my main goal is to minimize volatility and try and achieve a 5% – 7% total return equal to 2-3X the 10-year bond yield. 2018 was a positive year, +2% vs. -6.4% for the S&P 500. But I was up closer to 11%. Such volatility is unwelcome.

Real Estate: $6,550/month (32%)

Real estate used to dominate my retirement portfolio income (~60%) until I sold a significant SF rental house in 2017 for 30X annual gross rent.

I ended up reinvesting $600,000 of the proceeds in mostly dividend-paying stocks, $600,000 of the proceeds in mostly municipal bonds, and then $550,000 of the proceeds in real estate crowdfunding ($810,000 total) in order to not lose too much real estate exposure.

I did get a surprise $45,598.04 distribution on 4/16/2019 from the RS DME fund where I have a total of $800,000 invested. The fund has 17 investments, across 12 states, and 6 property types. My Class A Austin Multifamily property was sold for a 24.6% return over two years.

So far the fund is returning a 10% cash-on-cash return net of fees. I'm hoping the end IRR is much higher after the equity investments are sold within the next 2-3 years.

Real Estate Crowdfunding In Search of FIRE

For retirement portfolio calculation purposes, although I received $45,598.04 in distribution, I'm only inputting the profits as passive income to stay conservative. Perhaps there will be another significant distribution later in the year.

Real Estate Crowdfunding Distribution

Once about half my RS DME fund distributions are returned, I will look to reinvest about $300,000 in a couple Fundrise eREITs to further diversify my holdings and platform exposure.

So far I like the simplicity of investing in a real estate fund versus spending time trying to pick the best deals. But if I'm going to retire again, I'll have more free time to do research on individual investments.

My goal is to always have at least 30% of my net worth exposed to real estate as it is my favorite asset class to build long term wealth.

I haven't raised the rent on my SF 2/2 condo in almost three years. At $4,200 a month, the property is now under market value by $400 – $500 a month. But I plan to just keep the rent the same because they've been good tenants. I'll wait until one or both decides to move out before raising the rent.

Our Lake Tahoe property is coming back to life! We've had a fantastic winter in 2018/2019, which has resulted in a roughly doubling of net rental income over last year. The mortgage is now paid off and the winter in 2023 was also epic.

As the storms have subsided, we plan to finally take our boy up to the mountains. Spending time with my own family has been a dream of mine since I first bought the property in 2007.

In Search Of FIRE: Financial Samurai Retirement Portfolio Review

Alternative Income: $5,220/month (25.6%)

Online books sales for How To Engineer Your Layoff has steadily increased each year since the first edition was published in 2012. I completely updated the book for its 6th edition in 2023 to account for negotiation strategies post pandemic. Use the code “saveten” to save $10.

The new edition will have even more case studies and strategies to guide people to better negotiate a severance.

The amount of positive feedback we get from readers who've successfully negotiated their severance has been tremendous. If you plan to retire early, it behooves you to try and negotiate a severance. You have nothing to lose.

To generate $50,400 a year in almost passive online income from a book would require amassing a $1,008,000 portfolio generating a 5% return. Not needing to have startup capital is one reason why I'm so bullish on building online real estate. There is almost no risk except for putting your education and creativity to use.

Alternative Investments Doing Well

As for my venture debt investments, I'm still waiting to get paid in full for my first venture debt fund from five years ago. The second venture debt fund just did a 25% capital call for a total of 92% of the capital committed. Depending on the final investment in the first fund, the IRR is going to be anywhere from 5% – 16%.

Finally, I invested in my first venture capital fund. This is a 10-year, $600 million fund by Kleiner Perkins where I don't expect to see any income until perhaps year five. The main partner has a good track record and is a friend of a friend.

Here are some thoughts on why I like to invest in private funds, despite the high fees. I like private funds and private investments during volatile times because they are less volatile.

In Search Of FIRE: Enough To Retire

Here is my latest passive income streams in my search for FIRE. As you see, my passive income has grown by over 50% since 2019. This shows the power of investing for the long-term and compounding.

Due to inflation, my goal is to now shoot for $400,000 a year in consistent passive income to take care of a family of four.

Financial Samurai passive income investments 2023

Based on this deep-dive analysis, my wife and I should have enough to live a comfortable retirement lifestyle in San Francisco or Honolulu.

Keeping lifestyle inflation at bay while steadily growing our various incomes streams has been key to building our retirement portfolio. I've been wanting to buy a fancier house for the past couple of years now and have chosen not to so far.

Re-Retiring Is Not Easy When You Have Young Children

What I find most interesting is that even though mathematically I shouldn't have a problem retiring, I still have trepidation about selling Financial Samurai and retiring again.

Change is always hard, especially after you've spent a decade doing one thing. Giving up a steady income stream is also scary when you've been through the 2000 dotcom bubble and the 2009 financial crisis and now have a family to support.

Eventually, we'll need to start spending our retirement portfolio income. But as of now, we plan to continue reinvesting 100% of our investment income and saving 80% of our active income until a retirement decision is made.

Sam Dogen, Financial Samurai is the pioneer of the FIRE movement, Fortune profile if him wanting to go back to work

Related: Ranking The Best Passive Income Investments For Retirement

Reader Questions And Suggestions

Readers, any of you planning to retire soon? Are you in search of FIRE? If so, what type of deep dive retirement portfolio analysis have you done to ensure that financially everything will be OK once you retire? Do you see any holes in our retirement portfolio we need to work on shoring up? Featured art by Colleen Kong-Savage.

Update 2023+: I've grinded things out for over 8 years since I published this post. Passive income is close to $380,000 a year and our net worth has increased by another ~40% thanks to the bull market. I plan to retire once Biden is in office and there's a vaccine. My search for FIRE will never end. However, I'm glad to finally take things down a notch. In Search Of FIRE is a FS original post.

Pick up a copy of Buy This, Not That, my instant Wall Street Journal bestseller. The book helps you make more optimal investment decisions so you can live a better, more fulfilling life. 

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter and posts via e-mail. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. 

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70 thoughts on “In Search Of FIRE: Financial Samurai Retirement Portfolio Review”

  1. Piyush Trivedi

    Can you please share what amount of investment is required to generate the monthly returns you have on Stocks and Bonds of the portfolio? Also, what kind of passive returns does this include? Only dividends or does it include stock/bond price/NAV appreciation?

  2. I can get a grasp on most of it, school and healthcare costs, except how your house seems to have become a bigger factor as your retirement progressed. If the mean home in your area is $1.6MM, but you’ve owned yours for a decade or more I don’t get the relevancy. I sounds like you could move to Hawaii now with your home equity and maybe have no mortgage. Personally I would (and did) pay off my home before early retirement. Good luck with monetizing your site. I’ve enjoyed it over the years.

  3. I am still confused as to how you can generate so much passive income from stocks and bonds? Is it really just from dividends ?

  4. Mary Panzer

    Spending any money on PRESCHOOL is completely crazy. The boy is 2.5 or 3. What can he possibly learn that would be worth 1800$/mo??? In California you are not required to send your child to school till 6 yrs. old. Why not teach him everything you want him to know? You can invest 1000$/year and buy homeschooling curriculum far superior to anything he will learn in preschool, and also not have to reteach him to be polite, or keep him from getting bullied, or any number of other things that happen at school. No one will love your son more than you do. Just as no one will love your money as much as you do.

    1. I don’t think it’s crazy, but I do think it’s expensive. What did your children do before the age of five?

      There are benefits to preschool, including more social interaction, Alvin with potty training, and getting relief as parents.

  5. Thanks for sharing your story in progress! That’s nice that you’ve been so transparent with your numbers.

    Seeing you laying out what it’s taken you 20 years to accumulate shows that patience is a must.

    I think you guys definitely have enough to live a comfortable life if you decide to sell the site. Hope you don’t!

  6. Sam,
    Congrats! Another great article and helps me reflect on what I need to do.
    Also would this count as your quarterly review? Any updates on where you think the market is headed as you have done in previous quarterly reviews/forecasts?


  7. Sam, big FS fan. Any chance you can post your approx. account $ balances for each bucket so we can see required $ amount to generate returns?

  8. Very impressive. Private school tuition also throws a wrench into my plans. Instead of saving enough such that you can afford to cover the incremental $2000/month from passive income, what about allocating a chunk to pay the projected tuition costs (with inflation adjustments) for the amount of time you think he’ll be in private school. So instead of needing an extra $800k (to throw off $24k a year at 3%), maybe you really only need to set aside ~$520k (40k year X 13 years) or even less. Your approach is more conservative, of course, but just a thought.

  9. Congrats Sam on your success with the blog. You provide so much detail on our posts and as a reader, I really appreciate you to put in time with your knowledge to pass it along to us. I’ve read your blog for about a couple years now and regret that I should have read your blog much earlier than that in the early 2010s.
    Did you end up enrolling your son at the preschool you initially wanted to take them(Presidio Knolls?)

  10. Why are so many blind to the apocalypse that awaits us?

    I’m hearing the same garbage I did early 2000 and then again in 2007.

    Peeps never learnz.

  11. Hi Sam, you blog is great. I have learned a lot! Please keep up the great work! Question- is the passive income on stocks dividend income only?


  12. the end is near

    A sign of a top.

    Youtube channel that typically touts work at home opportunities out of the blue does a video explaining to newbies how to invest in the markets for very little money.

    Odd Lot Larry feels bulletproof now.

    We know how this ends.

  13. Ms. Conviviality

    While I don’t see Financial Samurai in your retirement portfolio, I’m positive it will create a big gaping hole in your life so you should keep FS running! ;)

  14. I have a long way to go until retirement but still, think about it quite a bit. When do you think is a good time to do a deep dive pre-retirement analysis (5 years til retirement, 3, 2)?

    1. I would think you would want to do a serious check-in against your goals once you had assets that might be an issue with your income time horizon. If you can’t deal with volatility in equities and plan to move toward bonds or blue-chips, then you probably need to start paying serious attention 7-10 years out. That’s a simple example, but I think that kind of hygiene will make the final analysis much easier, more familiar, and more reliable.

  15. Man if you can sell an asset like this website at a decent multiple and have them have to pay you to keep it alive and humming along, that’s a no-brainer! My challenge when my partner and I considered selling our business we were involved in was everybody gets cold feet when the people who are the driving force want to sail off into the sunset. Luckily for me it happened anyway, but didn’t work out well for those who thought things would proceed as normal after the purchase at the margins we could produce. Websites are way different I understand because your content for five years ago can still draw in traffic and revenue. Is there any examples of where it worked out well for the person who is doing the buying a one man show FIRE website? If so, I think in your shoes I would be doing the buying and not the selling… Beach house in Hawaii would be pretty damn nice, I’d blog from there if it were me!

  16. Steve Sheets

    For selfish reasons (I want to continue enjoying direct Sam content), I dug out this old gem (


    Thanks to a tremendous disconnect in the marketplace for buying income producing websites, you should be buying all day long. If you were lucky enough to buy income producing assets in the downturn (2009-2011), even better because you’ve not only seen appreciation due to a rise in valuations, but also a rise in income as well.”

  17. Your plan seems very solid. Really enjoy all of your posts, been a long time follower. Thank you for all you do. As mentioned above by another reader, we see that you did not include the sell of Financial Samurai as a hedge. Got it.

    However, it is just not clear how reliable the $50K/year related to your Layoff book would be if you did no longer had the website to promote it. Have you considered this somewhere? Are you able to stress test it?

    More importantly, thank you for all the great content, idea generation, and sharing over the years. It is sincerely appreciated! Really hope you personally keep this going for a longer period, since it’s your unique approach that keeps the site relevant and engaging.


    1. Hi Ben – I’d retain the rights of the book, unless the acquirer wanted to buy that as well. Can also figure out a profit sharing agreement as everything is negotiable. It’s cool the book is registered with the Library of Congress and has an official copyright.

      Thanks for reading and sharing all these years!

  18. jdogsupreme

    In light of your desire to minimize volatility as you approach your next retirment I am interested in your read on the all weather portfolio? Is this something you have considered?

    It is 40% long term treasuries (20 year), 15% intermediate treasuries (7-10 year), 30% s&P 500 index, 7.5% gold, and 7.5% comodities index. Some of the back testing shows pretty low volatility with a decent rate of return.

  19. Hi Sam,

    How do you think Financial Samurai being somewhat of a personal brand affects it’s value in event of a sale? I think a lot of your site’s value comes from your personality and involvement and I’m wondering how a PE firm might view this when valuing your website?

    1. I think it helps me be able to keep some part-time consulting opportunities with FS if I were to sell. There is so much opportunity to build products and scale the brand like Rich Dad, Poor Dad for example. Someone just has to create these products under the Financial Samurai principles.

      What people don’t realize is that the posts they see are only a portion of the content that is responsible for the traffic.

      From what I can tell, there is no other site out there that combines story telling with search engine optimized content for business such as FS. I can easily hire lots of writers to produce revenue focused posts. But another site cannot easily start writing stories.

      How about yourself and your business? What are some of the pros and cons and what have you discovered when talking to potential acquirers? I’ll include it in an upcoming post!

  20. The ebook line is so inspiring to me. Have you thought about growing that via paid marketing and other forms of marketing?

    For instance I searched “negotiate a severance package” on google. Yours was organic search result #5 and there were no paid ads.

    Just an idea.

    Have you written any posts about producing ebooks or other information products? I have one I’m thinking about but I have a long way to get there!

    1. Yeah, I have admittedly been very lax at trying to promote my severance negotiation book. It’s partly because I didn’t have the fire to try to make a lot of money from it. But now that the third edition is coming out, I think I will be more promotional and go on more podcasts and stuff. The book will be almost 200 pages and the feedback I’ve gotten continues to be extremely strong.

      Structurally, it makes sense to figure out a severance b/c fewer and fewer people are staying at their day jobs for life.

      I don’t recall writing a post on producing ebooks and info products. Maybe something after my 10 year anniversary.

  21. “If our son does not get into a reputable public school near by, then we’ll be forced to spend about $3,000 a month for elementary school and likely $5,000 a month for high school when the time comes.”

    I’m curious if you’d thought about simply moving to one of the nearby burbs with great schools…Palo Alto, Marin, Piedmont, Burlingame, etc., etc. This seems like the classic move that many young SF families make. That way you can go with great public schools all the way through HS. Where you live now in the city (nice area) is almost suburban relative to the more central neighborhoods most people think of as classic city living. You sure have a large choice of communities with great public schools nearby, so I’m curious why you haven’t mentioned that?

      1. For me it’s simple, as no kids = no schools ;) But if I did have kids then it would be a real dilemma as I really like urban living, and the burbs (as nice as they are here) I find too sterile. (Not sure if that’s an issue for you though.)

        This is slightly OT, but when you sold your Marina home, did you consider doing a 1031 exchange into passive funds like DST’s?

      2. Actually the reason I brought this up is because you said above that you split the proceeds of the home sale into stocks, bonds and real estate. With a 1031 exchange you can avoid the capital gains tax on the portion that you reinvent back in RE, which of course is an advantage. So I was curious about your thinking on that.

  22. Hi Sam,

    It’s a joy to read your articles. I like your detailed analysis and explanation behind each category .

    I was wondering for REIT do you have portfolio listed anywhere ? Just curious as I have been thinking about it but have not explored yet . Also the return seems to be very low( 810k investment vs 27k yearly return).

    Best Regards.

    1. I include my public REIT positions as part of my stock returns, but it could be part of my real estate returns as well.

      I’ve owned O and OHI for a very long time.

      The $27K early estimated return on $800k in my real estate crowdfunding fund ($10K was my first investment in an individual project) is low b/c I’m being conservative and also because 100% of the 17 investments are in equity deals, not debt deals that don’t exit for years. The real IRR will be determined on the exit.

      So far, 13 of the projects are performing well, 3 are underperforming their targets but still providing a positive return, and 1 looks to be loss making based on the latest quarterly result.

      See: Debt Or Equity Real Estate Crowdfunding Investing

      How about you? How are you investing in real estate and what are your retirement portfolio plans?

  23. Financial Freedom Countdown

    Sam, any reason you have the house fund. Are planning to buy another property after selling your SF property? If it is Honolulu then wouldn’t your GGH home sale provide the capital for Hawaii If it is in SF then isn’t the loss of Prop 13 a bummer?
    P.S. Hoping you continue to generate content and don’t sell FS

    1. Yes. After gaining two years of reprieve from being a landlord of animal house, I’m reading to buy another property with ocean views in the city because I still think there is so much value. That, or I will buy my beach house in Honolulu.

      Property went down in 2018 after going up a little after I sold. So we’re basically about flat. The house I sold was on a busy street next to the busiest street in all of SF. I’m very thankful to have got out with a profit.

      I’m not bummed about losing Prop 13 b/c I was still paying $24,000 a year in property taxes.

      How are you investing?

      1. Financial Freedom Countdown

        I am invested in mainly paper assets excluding my rental and primary. I have considered SF but the homeless situation coupled with the politicians catering more to renters v/s owners has me always worried.

  24. Sam –

    I’m confused. You mention using two different tax rates. Do you use a 28% tax rate or a 20% tax rate?

    Which one is it and how do you come up with that? For example, do you include NIIT, which is an additional 3.8% on much of your investment income? Do you account for the different tax treatment of qualified dividends? Did you apply the higher tax rate to real estate income versus other income? Do you include CA (or HI) state income tax? Have you looked at whether your investments would trigger AMT?

    I am trying to understand the tax analysis better since, I think, there’s a lot more to unpack.


    1. Thanks for all your questions. For investment income, I use an effective 20% tax rate due to lower taxes on long-term capital gains, dividends, amortization expense and tax free income from municipal bonds.


      I would use a 28% effective tax rate if I had to reach my $15,000-$18,000 a month after tax passive income go through W-2 income.

      How about you? Please share some of the details of your retirement portfolio. What effective tax rate would you use?

  25. What is it about these high cost of living areas (HI and SF, CA) that is so attractive to you. You realize you could raise your kids in a low cost of living state like TN or NC or SC or even AR, and your wouldn’t need half your desired income needs. You could easily get by on less than $100k/year and have the outdoors and great places to visit like the smokey mountains and Nashville. Warning though, these places are way more conservative than what you’re used to.

    1. Probably family and friends, and also good food and weather. How about you? Where have you retired to our plan to retire and for what reasons?

      I’m totally down for aggressively investing in Memphis real estate and other heartland real estate areas though. The rental-year-olds definitely help pay for my higher cost of living in San Francisco or Honolulu.


      1. Fascinating. I used to be pro-Heartland real estate investing (that post was a big reason why), but after continuing to see the trend of top human capital moving to the coastal places, I no longer agree. The Heartland eREIT on Fundrise continues to underperform the East Coast, Income, and other funds. The election of Trump barely moves the needle in terms of talent and capital flow to the heartland. I bet if you did a LinkedIn analysis of HBS grads or Ivy League grads it would overwhelmingly be not heartland, and possibly even stronger than in 2015.

        Companies like Amazon continue to set up shop in places like NYC and DC. Knowledge economy workers continue to strongly prefer places with komboucha on tap and yoga studios rather than churches and big open land. California continues to add states to their “no state-funded travel” list due to culture war issues, and the Heartland continues to lose there. It’s unfortunate, but this trend and the “Big Sort” seem much stronger than a few words and books on Hillbilly Elegies can fight

        1. Cool. Please share more about your heartland real estate investments and how you invested in them. Highlighting some numbers would be great. thx!

          I’m long SF real estate already, so I hope you’re right.

          1. Fundrise eREITs:

            Heartland: 8.1% in 2017, 5.7% in 2018, 1.4% Q1 2019
            Growth: 17.0% in 2017, 14.0% in 2018, 2.8% Q1 2019
            Income: 9.7% in 2017, 9.1% in 2018, 2.5% Q1 2019
            East Coast: 10.2% in 2017, 12.2% in 2018, 3.4% 2019

            The other funds have strongly outperformed Heartland

            Also, nearly all of the Fundrise Heartland investments are in Denver, Austin, etc. I really don’t think Nashville real estate will out-appreciate the rest. The Big Sort is just starting – all future trends like automation will further concentrate economic gains in big cities like yours, for better or worse.

            Politicians aimed at reducing inequality do so on a class-based basis, not a state / region-based one

            1. Great insights! And good thesis.

              The thing is, it all depends on one’s existing real estate and investment positions. I am already largely exposed to Growth and San Francisco real estate. I’m looking to diversify.

              Where are you based and where are most of your RE investments?

  26. Things look good from what I’m reading. Once I read the line, “Because we’ve been in the habit of saving at least 50% of our after-tax income since graduating from college in 1999 and 2001, respectively, it would feel foreign to not continue saving in retirement,” I had a feeling you might be feeling a little weird trying to FIRE.

    Embrace the relaxation that can be FIRE is all I can suggest. Of course, I’m not talking from experience which means it’s probably worthless advice. But at some point, you have enough. You appear to have enough.

    1. True, my stress level went down to about a 4 out of 10 in 2012from a seven out of 10 when I was working.

      One of the reasons why I want to move to Hawaii is because when I’m there, my stress level goes down to a three out of 10. I’m going to assume the average person has a stress level of about a six.

      How are you? Where are you and your financial journey? Does this post make it sound like I am overly stressed out? I think I’ll do a follow up podcast after I read some more feedback.

      1. Hawaii could be fantastic. I would think that you’d settle into a nice, new normal there.

        My wife and I are doing well. After my wife cranked out an awesome spreadsheet, it looks like we could probably retire at 55. That’s 11 years out. But we enjoy what we do for a living to a degree and are planning on semi-retirement. That may occur in 5 years or less. We just got serious about 6 months ago so we’re learning.

        I really didn’t take it as overly stressed out. You seem to be very focused on looking at many angles. And you want to maintain a certain lifestyle that is difficult to have, let alone maintain. My gut tells me that you’re just planning for the worst so you can be pleasantly surprised when it all works out.

        I still view it as hard* to live off of investments as opposed to a paycheck for services rendered. Even though you have a scale-able website (I suppose like all websites,) it still is time spent to get money. For me, I’m sure that I will feel odd when drawing from investments someday as opposed to getting W2, so it’s good to read about your thoughts on this.

        *Note. To anyone laughing at people being concerned about how to manage millions in investments or perhaps even being annoyed by it…yes, it is a rich/affluent person problem. It’s a very good problem to have. And being self-aware of this, helps keep it in perspective.

  27. It appears that your passive investment income exceeds your expenses without factoring in income from a) running Financial Samurai or b) selling FS and investing the proceeds. I wouldn’t expect you to divulge how much you expect to sell FS for, but wouldn’t that create a very big cushion for you even if your wife didn’t go back to work?

    1. Yes, good observation.

      I should be able to reinvest some of the proceeds from a Financial Samurai sale inti more passive income. I’ll have to calculate how much that would be exactly for a new post perhaps. I do want to do a thorough analysis of what people should think about before selling a business.

      1. Thank you the info. I, along with my two partners, have spent 12 years building a business that’s been good to us. I wish it was one that could be sold, but it’s a law firm and that’s not really possible.

        1. Why can’t the law firm be sold? Shouldn’t there be some brand equity and partners with existing clients on retainer? Or are you saying you can only sell your partnership to another partner?

          1. The total value of the law firm is in what the partners create. You can’t really sell a client, and we are a class action firm that doesn’t really have clients in the traditional sense anyway. The only real value is our ability to have ideas and convert them into revenue.

            Not saying that some law firms can’t sell, but when they do it’s at very low multiples and requires partners to stay on to work.

  28. Wow Sam, talk about a thorough and detailed analysis. For those of you who are as lazy as I am, you can just look at your tax return and pull your interest, dividend, rental and K-1 income off your return. Add them up and this is your passive income.

    In your chart you have $33600.00 under stocks. Is this number your current dividend income?

    Thanks, Bill

  29. What motivated you to invest in an early-stage VC fund now?

    You’ve been somewhat critical of angel investing / investing in startups in the past.

    1. I am critical of my own ability to invest in early stage start up’s. But Kleiner Perkins is one of the blue chip venture-capital firm’s and I know the fun manager. I even got to talk about his philosophy and his background during an hour long hike in Joshua tree in March. I feel good getting to know the people who are responsible for investing my money.

      I only invested about $140,000 in the fund, which was actually the limit because the phone had $1.2 billion in demand and only $600 million in supply. I figure if this one does well, I have access to other funds by Kleiner Perkins. It’s kind of like a hedge. I think I’ll write more about it and an upcoming post.

  30. mcarthur wheller


    Hold the phone, where can I get a Financial Samurai shirt? How long have these been available? Why have you not mentioned this previously or is it an optical illusion? Is there only 1 existing? Is there a box sitting somewhere full of these neat-o shirts? Do you have ball caps too? Cooking aprons? How can you throw that photo in with no explanation? Or was there a previous explanation that I missed? Or is there a pending explanation that will enable to purchase said Financial Samurai shirts in mass quantity?

    I also noticed you sneakily (couldn’t remember how to spell subtlely) threw in you need to support a child or 2 while living in San Francisco or Hawaii. 2 in my book means you are either thinking of or going to have a buddy for the youngest samurai. I bet the grandparents are all for it. Do you have baby FS shirts? That is cool! 2 small humans is better than 1. I see 2 custodial ROTH IRAs on the horizon.

    Thanks SAm,


    1. Why funny you should ask! The Financial Samurai merchandise store is actual in its final stages. You can buy some cool swag here! Feedback welcome.

      I’ve commissioned the talked Colleen Kong Savage for all the artwork. More selection will be added over time.

      Enjoy! And yes, praised be if we are blessed with another child.

  31. Wow! This is one thorough post! Congrats on accomplishing SO much! That sure took a lot of preparation, long hours of hard work, and guts. Amazeballs!

  32. Money Ronin

    I’ve been reading your blog for 6 years now since I unknowingly started my own early retirement. I don’t quite understand this new source of stress. You’ve build a decent passive income stream. Even if you and your wife never work again after selling the blog, you should be set. If you took the proceeds and stuffed it in your mattress and pulled some out every now and then you should be set.
    I understand the stress of investing and optimizing a large cash infusion but I don’t understand the concerns of living a comfortable retirement. I’ll have the added pressure of paying 4% on my cash infusion because it’s a cash out refi.

    1. Yeah, Unfortunately I have not yet reached enlightenment or monk like status yet for stress free living.

      To me, change is always a little bit stressful and I try to do my best to anticipate change.

      How have you been able to live so stressed free? Can you share some of your strategies of being a parent and a provider? How many kids do you have?

      I’m always looking for tips on how to get happier. Thx

      1. Sorry for the delayed response; I was on spring break with the family.

        From what I can surmise based on reading FS, we are in the same ballpark with regard to income, wealth and origin story. I’m a decade ahead of you in the parenting department. For my kids’ sakes, I worry a lot more about the negative effects of having too much vs. too little.

        Being a new parent is always stressful, but you’re going to adjust. If your son doesn’t attend the $1800 per month preschool, it won’t be the end of the world. Whether that happens because he doesn’t get accepted, you can’t afford it, or you realize that it costs more than room and board at a UC, who knows? This applies as well to your other investments and endeavors.

        You’ve diversified your income streams and you’ve planned for various contingencies. The only thing left to do is to be flexible with your thinking, which from everything that I’ve read, you are fully capable of. Even if the worst case scenario happens, hopefully you can see that you will still be okay and you’ll more than get by.

        As your son ages and becomes accustomed to your lifestyle, he will be in far greater danger of the negative effects of having too much vs. little. I am having a very difficult time teaching my kids to appreciate what they have since they’ve always had it. I’ve explained to them that I didn’t have the things and opportunities they have. I’ve shown them the homeless encampments near our home. I’ve taken them to third world countries. We’ve vacationed in spartan and tiny hostels/local homes. They still don’t get it.

        If we ever suffered a financial calamity, I actually look at that as a teachable moment for my kids. I know I’ll be fine because I’ve been through difficult times (as I know you have). They perhaps need the same life experience at some point.

  33. Congrats Sam. You mentioned “all good things come to an end. We must frequently adjust in order to keep the good times going for longer.” Do you really view it as good things coming to an end or just using the expression? I think I get your overall message that occasional change is great to keep from getting bored and add variety to challenge each of us. I guess for your sake I am asking if this is continued good things of another variety ;)

    1. My problem is that I have a habit of always trying to forecast my misery 5-10 years out in order to stay happy.

      I see a bright future full of challenges. Namely: rising living costs, injuries, sickness, death. Nothing lasts forever, so we’ve got to make the most of the present and constantly try and anticipate potential hardships.

      When I was 22, I just felt that getting into work by 5:30am and working until 7:30pm was unsustainable. So I decided to save aggressively from day one to one day be free.

      Same thing w/ ever rising rent. I figured at age 24, I better start saving and investing for a downpayment, or else I’m going to be screwed if I want to live in San Francisco.

      Just gotta be realistic about the future. And yes, nothing good lasts forever. Seems sad, but it doesn’t have to be. Let’s make it a game of continually self-improvement!

  34. I am trying to do similar thing to you Sam but on a much smaller scale (as I don’t have the HCOL and its associated cash drains that you do).

    Incredible amount of passive income you are currently generating. It is the equivalent of a primary care doc who is busting his or her ass 60-80 hours/week.

    I am hoping to get to a $125k/yr passive income stream (not including retirement accounts) that would let me live a remarkable life where I am currently situated. When the retirement accounts kick in I think I would have more than enough to handle unexpected things that happen as the body ages.

    Best of luck and still incredibly sad that you are in the process of shopping FS

    1. Thanks for making me feel good b/c I’ve been busting my butt aggressively saving and investing since 1999 too. 20 years feels like a long time, but it also has gone by quickly. I can’t waste time.

      I’ve stubbornly chosen to live in a HCOL area due to family and friends. It would be wonderful if I had family of friends in a lower cost area.

      Good luck on your journey! And enjoy that 50 foot water fall in your house!

  35. Dave @ Accidental FIRE

    You’re killing it on all fronts, and making everyone else feel bad. Stop running up the score :)

    1. Yeah, it hurts to realize how far behind I am. Time to go back to reading Jacob @ ERE to feel better about myself!

      In all seriousness – my wife and I won’t ever see these numbers (at least not before we’re in our seventies) but my twins might be able to, if they apply themselves. I’ll be showing them posts from this blog, along with ERE and a couple others, before they leave the nest so they understand what’s at stake and what’s possible. Right now they’re only 21 months old so I’ve got a lot of time to think about how to frame these issues (and save copies of the blog posts). Keep up the great work!

      1. Any idea how Jacob is doing at his job? He went back to work about 7 years ago in quant trading.

        Going back to work is always a solution for FIRE folks.

        Hopefully you don’t live in a high cost of area part of the country and can need less to live comfortably.

        1. Hmm, perhaps my comment made our situation sound worse than it is. We have a net worth in the very, very low seven figures. We actually achieved FIRE in Houston Texas, then decided to move to pricier Seattle because we like it and figured we’d never really quit working anyway. Right now I’m working part time and wife is at home. We’re a quintessential DIRE family!

          No idea what happened to Jacob. Perhaps he’s now an anonymous billionaire trader living next door to Oprah…

  36. Congratulations! You two have done really well. It looks like you’re set for a very nice lifestyle in either SF or Honolulu. Your portfolio looks good, not too aggressive.

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