The Financial Samurai Podcast

Hosted by Sam Dogen

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264

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Oct 2026

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About the show

Helping listeners achieve financial freedom sooner rather than later. Financial Samurai is America's number one personal finance blog and podcast helping you make more money, save more money, and live the life that you truly want.

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60 recent

October 21, 202637 min

Buying More House Than You Need: Was It Worth It Three Years Later?

In 2023, we stretched to upgrade into a larger home we didn't need. Three years later, I sat down with my wife to talk through the whole experience and answer the question everyone keeps asking us: was it worth it? The short version is that we found a unicorn. A home on a large lot at a relatively low price point, fully remodeled and landscaped, with a view of the Golden Gate Bridge. In 24 years of hunting for property in San Francisco, I'd never seen anything like it at that price. So we had to buy it, even though it meant selling a chunk of stocks and bonds and blowing up our passive income. In this episode, my wife and I get honest about both sides. The joy of watching our kids run around an enclosed front yard with zero fear of traffic. The peace of finally being off the property ladder. And the part that still stings: the $1 million to $1.5 million in stock gains we likely gave up by turning investments into a house we live in every single day. If you're sitting on big gains and tempted to upgrade into more home than you need, this one is for you. What We Cover Why we upgraded into a home we technically didn't need, and how long it took to convince my wife Finding a unicorn property, large lot, full remodel, Golden Gate Bridge view, at a price I still can't believe The real opportunity cost of selling stocks and bonds to buy a home, and the dads I know who left 10X and 20X gains on the table Pros and cons of stretching to buy, and the six months we spent living paycheck to paycheck afterward The biggest surprise: how cheap maintenance has actually been versus the 1% rule of thumb Why a large, usable lot can matter more than a view once you have active kids Using a home upgrade as a form of decumulation, spending down wealth to actually enjoy it What we'd do the same, and the one thing we might do differently next time Deeper Dives Mentioned In This Episode Blew Up Our Passive Income And No Longer Financially Independent Embrace Living Paycheck To Paycheck A Great View Or A Big Lot Enjoying A Home With An Enclosed Front Yard The Best Time To Own The Nicest House You Can Afford Paying for A Home Inspection Is Worth The Cost Companion Post Read the full written breakdown, including our three-year maintenance costs and my checklist for anyone planning to upgrade into a home they don't need: Whether Upgrading To A Home You Don't Need Is Worth It . Subscribe If you enjoyed this episode, subscribe to the Financial Samurai podcast on Apple or Spotify, and join 60,000+ readers by signing up for my free weekly newsletter at FinancialSamurai.com so you never miss a thing.

September 9, 202645 min

Mezzi: The AI Investment Advisor That Saved Me Over $20,000

This summer, my new AI wealth advisor, Mezzi , discovered roughly $300,000 of Google exposure I didn't know I had. It sounds a little absurd, given the amount. But I've been investing in Google for over 15 years, and with a complicated net worth it's hard to track everything accurately when your mind anchors to old price points. Weeks after I trimmed the position, Google sold off about 10%. I sidestepped over $20,000 in losses. Then I did something I'd never done in 17 years of writing about money on Financial Samurai. I invested in the company. As an AI maximalist, I'm always hunting for new AI products that help build wealth, and for promising private AI companies to invest in. Mezzi turned out to be both. So I sat down with Manish Jain, CEO and co-founder of Mezzi, over lunch in San Francisco and then again for this episode. We get into: Manish's entrepreneurial path and why he left JPM to build Mezzi Why he built an AI wealth advisor instead of another robo-advisor What Mezzi surfaces in a portfolio that most investors miss, from overlapping positions to fee drag Where AI wealth management goes next, and the parts it still can't do Sign up for Mezzi AI for free today. Use code: FS30 to save 30% off the premium plus version. Disclosure: I'm an investor in Mezzi, an affiliate partner, and Mezzi sponsors this podcast. I only partner with companies whose products I use myself. If Mezzi weren't already open on my laptop most weeks, this episode wouldn't exist.

August 4, 202634 min

Nobody Is Ever Truly Independent: Caring for Parents, Raising Kids, and the 37-Year-Olds Still Cashing Dad's Checks

Being an adult is hard, and nobody is ever truly independent. In this episode, my wife and I talk about spending 30 days in Honolulu with my parents and what it's like to slowly shift from being cared for to being the caretaker. We also get into a bizarre encounter with two park rangers on an empty public tennis court while I was teaching my own kids, and a discussion about what a real adult actually is when a 37-year-old still depends on her father for money. Three generations, one uncomfortable question about who takes care of who. We also touch on how hard it was to spend our Summer YOLO Fund. The full accounting comes in tomorrow's post. Related posts: Real Adults Are Not Financially Dependent On Their Parents (But That's OK) : https://www.financialsamurai.com/real-adults-are-not-financially-dependent-on-parents/ How Much A Family Needs To Earn To Live Comfortably By City: SF #1! : https://www.financialsamurai.com/how-much-a-family-needs-to-earn-to-live-comfortably-by-city-sf-1/ You'll Never Be Free From The Government: Introducing The Leash Ratio : https://www.financialsamurai.com/leash-ratio/ A Tax Identification System For Determining Your Level Of Freedom: https://www.financialsamurai.com/backwards-tax-identification-system/ Podcast Support If you enjoyed this podcast, please rate, review, and share. Every review means a lot, as each episode takes hours to produce. And if you want to achieve financial freedom sooner, sign up for the free weekly Financial Samurai newsletter at https://www.financialsamurai.com/news. You can sign up for ProjectionLab or Empower to help you better manage your finances, for free. I use both and they are long-time affiliates of Financial Samurai.

June 23, 202644 min

From Startup To Acquisition by Symantec: The Entrepreneur's Journey With Domingo Guerra

In this episode, I sit down with my friend and fellow school dad Domingo Guerra to trace his entrepreneurial journey: from growing up in Mexico, to studying engineering at UT Austin, to co-founding the mobile cybersecurity company Appthority with my poker and softball buddy Kevin, to selling it to Symantec in 2018. Today, Domingo runs his own seed-stage venture fund focused on cybersecurity, called Chispa VC. It always fascinates me how people become entrepreneurs, given that most of us just go to college and get a job. I wanted to start a company myself for the longest time, but I chickened out after Goldman Sachs offered me a job out of William & Mary. It took me until 2009 to finally stop waiting for permission and build something of my own . Domingo's story is the version where you take the leap much sooner, and it's a great one. If you'd like to connect with Domingo, the easiest way is to reach out to him on LinkedIn . Related posts: Y Combinator Demo Day: The Quest To Invest In The Best Startups The Startup Grind Will Make You An AI Maximalist Subscribe To Financial Samurai Enjoy the show? Please subscribe to the Financial Samurai podcast on Apple Podcasts, Spotify, or wherever you listen, and leave a quick rating and review. Reviews genuinely help more people discover the show, and they only take a minute. It's the easiest way to support the podcast for free. And if you want my best insights on money, investing, and building wealth delivered straight to your inbox, join 60,000+ readers and sign up for my free weekly newsletter . I've been writing it every week since 2009, and it's still the best way to never miss a thing.

March 26, 202630 min

Public Venture Capital Is Here: Why VCX Has Soared and What Fundrise Investors Should Do Now

With Fundrise's successful listing of VCX on March 19, 2026, its venture capital product, I want to discuss what's potentially next for the fund and for investors. The listing has far surpassed my expectations, and the expectations of most investors. Anything can happen during the 6-month lock-up period, so it's important to keep expectations low and stay humble. Don't spend any paper profits until you actually have liquidity. Financial Samurai has been working with Fundrise as a corporate partner for over 10 years now. I'm proud of what Ben Miller and his team have accomplished in democratizing access to venture capital through public venture capital . Let's see what the future holds! Related posts: After A Big Investment Win Stay Humble: Clean A Toilet How ETFs, Open End Funds, and Closed End Funds Trade Recommended Net Worth Asset Allocation By Age and Work Experience Subscribe and Support Financial Samurai Every podcast episode takes hours to record, edit, and produce. Your shares and positive reviews mean a lot and are greatly appreciated. If you've benefited from my writing in any way, please pick up a copy of Millionaire Milestones and Buy This Not That , and leave a review on Amazon . These national bestselling books will help you make better financial decisions and reach financial independence sooner rather than later. For more nuanced personal finance content, join 60,000+ subscribers and sign up for my free newsletter . Financial Samurai started in 2009 and is one of the top independently run personal finance sites today. Fundrise is a long-time sponsor of Financial Samurai and Financial Samurai is an investor in Fundrise products. Our investment philosophies are aligned. Best, Sam

February 24, 202623 min

Forget Learn To Code, Learn To Invest Instead To Survive

For more than a decade, the mantra for boosting your career and income was simple: learn to code. Becoming a programmer or engineer was seen as the clearest path to job security and high pay. But with the rapid rise of AI, coding is no longer the protective moat it once was. As I revisited my own FIRE plans after leaving work in 2012, I realized the one financial buffer that has consistently stood the test of time: knowing how to invest well. Forget "learn to code." Learn to invest. Becoming a competent investor may be the most important skill you develop to survive - and thrive - in the coming AI wave. Posts mentioned: Becoming A Competent Investor Is A Vital Skill To Master Gain Financial Security By Creating Financial Buffers For Your Financial Buffers The FIRE Movement Is So Back Due To AI Disruption Free Financial Analysis Offer From Empower Stay on top of your net worth with Empower , the web's #1 free financial app. Track your cash flow, x-ray your investment portfolio for excessive fees and inappropriate risk exposure, and use their retirement calculator to plan for the future. If you have over $100,000 in investable assets—whether in savings, taxable brokerage accounts, 401(k)s, or IRAs—you can sign up for a free financial check-up from a professional at Empower . It's a no-obligation opportunity to have a seasoned advisor—someone who analyzes portfolios for a living—take a fresh look at your finances. A professional review can help you identify hidden fees, inefficient allocations, or missed opportunities to grow and protect your wealth. More importantly, it can give you the clarity and confidence to know whether your current savings and investment strategy aligns with your long-term financial goals. I've taken advantage of three free consultations with Empower over the past decade and each session has helped me build more wealth. There's no rewind button in life. Make the most of everything, especially things that are helpful and free. The statement is provided to you by Financial Samurai ("Promoter") who has entered into a written referral agreement with Empower Advisory Group, LLC ("EAG"). Diversify Your Retirement Investments Stocks and bonds are classic staples for retirement investing. However, I also suggest diversifying into real estate. It is an investment that combines the income stability of bonds with greater upside potential. Consider Fundrise , a platform that allows you to 100% passively invest in residential and industrial real estate. With over $3.5 billion in private real estate assets under management, Fundrise focuses on properties in the Sunbelt region, where valuations are lower, and yields tend to be higher. Residential commercial real estate is attract. Meanwhile, the Fed is set to cut rates further. I've personally invested over $500,000 with Fundrise, and they've been a trusted partner and long-time sponsor of Financial Samurai. With a $10 investment minimum, diversifying your portfolio has never been easier. Subscribe To Financial Samurai To increase your chances of achieving financial independence, join 60,000+ readers and subscribe to my free Financial Samurai newsletter here . Financial Samurai began in 2009 and is the leading independently-owned personal finance site today.

January 22, 202632 min

The Wonderful Flexibility Of Coast FIRE with Andy Hill, Author of Own Your Time

If you are a parent who is interested in FIRE, you should listen to Andy Hill's podcast, Marriage, Kids, & Money on Apple, Spotify, and wherever you listen to podcasts. It's a great show that talks about all the financial and parenting issues all mothers and fathers face. Andy also came out with a new book called, Own Your Time: 10 Financial Steps To Put Your Family First and Escape The Corporate Grind . Go check it out, it's a great book for parents looking to achieve financial independence. On the podcast, talk about the merits of Coast FIRE, a type of FIRE that I've dubbed the most dangerous early retirement strategy to follow . But the older and more tired I get, the more I've come to accept Coast FIRE's merits. It's certainly beter than aimlessly grinding away at a job you don't love forever. If you enjoy this podcast episode, please support my guest Andy, and please share the episode and leave a positive review. Every review means a lot as every podcast episode takes hours to produce. If you want to achieve financial freedom, you can also sign up for my free weekly newsletter here .

January 6, 202617 min

Being Happy In Spite Of Everything

Happy New Year 2026, everyone. Despite a strong year in the stock market in 2025, I found myself feeling less happy due to some family health challenges. That contrast inspired me to reflect on what truly brings us greater happiness and gratitude. Related posts: 2025 Year In Review And The Happiness Curve The Best Of Financial Samurai 2025 Eliminated A Regret And Fulfilled A Childhood Dream Join 60,000+ others and sign up for my free weekly newsletter here . My goal is to help you achieve financial freedom sooner, rather than later.You can receive my posts in your inbox immediately after they are first published without ads by signing up here .

November 13, 202510 min

Housing Security: The Underappreciated Benefit of Owning In A Rising Rent World

The debate between owning and renting will go on forever — it all depends on your stage in life, finances, and lifestyle. But as you get older, one thing becomes clear: housing security matters more than ever . The last thing you want in retirement is to be forced out of your neighborhood because of rising rent. Yet as a renter, you have little control over how much your landlord raises prices, especially if you're not in a rent-stabilized home. With housing inflation outpacing wage growth, it's time to get neutral real estate by at least owning your primary residence. In this episode, I'll share why ownership becomes more valuable with age — and how to think about real estate in a world where affordability keeps shrinking. Read the post for more details and discussion: Please Don't Rent For Life: Housing Security Is Vital Other related post: Why I'll Never Manage Money For Anyone For Free Again Invest In Real Estate Passively If you can't buy a home yet, don't sit on the sidelines while housing prices and rents keep rising. You can still participate in the real estate market and build wealth over time — without needing to come up with a massive down payment. That's why I've invested with Fundrise , a platform that allows everyday investors to gain exposure to residential and industrial properties nationwide. With over $3 billion in assets under management and 350,000+ investors, Fundrise makes it easy to own a piece of the real estate market that continues to compound in value. Real estate has historically been one of the best ways to hedge against inflation and grow wealth passively. And with a minimum investment of only $10, anyone can start investing today. Fundrise has been a long-time sponsor of Financial Samurai because our philosophies align — consistent, disciplined investing in tangible assets to build financial freedom. Regards, Sam To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter . You can also get my posts in your e-mail inbox as soon as they come out by signing up here . Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

October 22, 202524 min

Permission To Live It Up In Retirement With Bill Bengen, Father Of The 4% Rule Going To 5%

Bill Bengen, the father of the 4% Rule, is back with a new book titled A Richer Retirement . In it, he raises his SAFEMAX—or safe withdrawal rate—from 4% to 5%. This change has major implications: retirees can confidently spend more and enjoy life to the fullest, while those pursuing FIRE or traditional retirement may not need to save as aggressively or work as long to achieve financial freedom. See related Financial Samurai post: Persmission To Live It Up In Retirement Free Financial Analysis Offer From Empower If you have over $100,000 in investable assets—whether in savings, taxable accounts, 401(k)s, or IRAs—you can get a free financial check-up from an Empower financial professional by signing up here . It's a no-obligation way to have a seasoned expert, who builds and analyzes portfolios for a living, review your finances. A fresh set of eyes could uncover hidden fees, inefficient allocations, or opportunities to optimize—giving you greater clarity and confidence in your retirement financial plan. The statement is provided to you by Financial Samurai ("Promoter") who has entered into a written referral agreement with Empower Advisory Group, LLC ("EAG"). Click here to learn more. Subscribe To Financial Samurai To increase your chances of achieving financial independence, join 60,000+ readers and subscribe to my free Financial Samurai newsletter here . Financial Samurai began in 2009 and is the leading independently-owned personal finance site today. Everything is written based off firsthand experience.

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