The Financial Samurai Podcast

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.
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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.

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/
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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
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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
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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