I firmly believe that above-average wealth is largely a result of luck – around 60% – 70%. If we fail to recognize our lucky financial breaks, we risk confusing our abilities with good economic times. This overconfidence can lead to poor decisions and increase the likelihood of financial ruin.
Since starting Financial Samurai in 2009, I’ve witnessed fortunes rise and fall. Time and again, hubris during good times proved to be people’s undoing. I experienced it firsthand in 2007 when I assumed my income would keep climbing. That misplaced confidence led me to purchase a vacation condo in Lake Tahoe, tying up 30% of my net worth in an asset I didn’t need. Over the next three years, the condo’s value collapsed by 50%. Oops!
Times are great again, and nearly every asset class has performed well in recent years. It’s tempting to chase even greater returns to ride the bull market higher. If you choose to do so, proceed with the understanding that every bull market eventually ends—and often not gently.
Be Thankful For Your Lucky Financial Breaks
As the year comes to a close, it’s a great time to review how your net worth has performed. To truly appreciate the progress, look back three, five, and ten years. For those who have consistently saved and invested a portion of their income, you’ve likely witnessed the magic of compounding!
While it’s important to celebrate financial growth, it’s equally important to recognize the luck that helped along the way. If we do, we will feel happier and more appreciative.
Let’s reflect on some lucky financial breaks that keep us grounded and humble. Here are five past and recent fortunate events that have shaped my life. I hope you will share some of yours in the comments section below.
Lucky Financial Break #1: Landing a Good Job After Graduating From a Non-Target School
My luckiest professional break was when a woman named Kim Purkiss selected my resume from a sea of thousands at a career fair in Washington, D.C., in 1998. Kim was a strong, determined Black woman who grilled me like a sausage during our interview.
Coming from William & Mary, a non-target school, I kept getting passed around the various desks at Goldman Sachs in NYC. Yet, Kim continued to advocate for me through seven rounds and 55 interviews until I finally landed a position in International Equities.
Once I secured the job, I worked hard to prove myself. But I was young, unpolished, and made mistakes—like overindulging in day trading. Unfortunately, the Dotcom implosion in 2000 didn’t help my case as the firm began cutting staff.
Looking back, I wouldn’t have even gotten my foot in the door without Kim’s persistence and belief in me. Her advocacy was a stroke of luck that set my financial journey in motion. Thank you Kim!
Lucky Financial Break #2: Investing in a Chinese Internet Company That Went Gangbusters
Before I wasn’t invited back for a third-year analyst position in 2001, I had one of the luckiest trades of my life: identifying a Chinese internet stock called VCSY. Its homepage featured a dial pad, where each number led to a different subject matter. With stocks like Yahoo and Ariba skyrocketing at the time, I figured Chinese internet stocks would be the next big opportunity.
I invested $3,000 into VCSY, and within three months in early 2000, it surged 60X to $180,000. Part of this meteoric rise was because I worked on the international desk and shared the idea with peers on the 49th floor, including traders. I also mentioned it to colleagues at Morgan Stanley and JP Morgan, and the buzz spread like wildfire.
Ultimately, I sold the stock when it was worth about $150,000. Luckily, I held most of the proceeds in cash as tech stocks began to crash soon after. This windfall gave me some much-needed financial stability as my career prospects took a hit.
Ultimately, 85% of my VCSY gains after tax were rolled into a San Francisco condo I bought in 2003. This was the start of my love affair with owning real estate – it generated income and its value wouldn’t just go *poof* overnight, like VCSY’s value did over the next two months.
Lucky Financial Break #3: A Helpful Advocate Prevented Unemployment
Elaine, a VP on my desk, played a pivotal role in saving my career. She was one of my biggest skeptics during the hiring process, even insisting on meeting me a third time for a coffee before making a final decision. Although somewhat intimidating, she became a mentor of sorts once I joined, and we bonded over our shared love of skiing.
Elaine often shared stories about the fascinating people she met on ski trips. As a single woman in her mid-30s, she was trying to balance her demanding career with her personal life, shifting her focus toward dating. I became her confidant during that period.
One day, a recruiter named Michael, who had a nervous voice, called Elaine, hoping to recruit her for a role at Credit Suisse First Boston. She wasn’t interested but told Michael to hold on and handed the phone to me.
This moment was serendipity. Elaine knew my future at Goldman was dim. If she hadn’t handed me the phone, I wouldn’t have secured a role at CSFB in San Francisco in June 2001—with both a raise and a promotion. That break kept my career afloat and gave me a fresh start for another 11 years.
Retiring in 2012, just as the bull market was starting to take off, was also lucky. Each year of rising investment values increased my likelihood of staying free. It’s better to retire in a bear market. This way, your finances and resolve will be better tested.
Lucky Financial Break #4: Spared by Google Algorithm Changes
In July 2009, I started Financial Samurai, partly out of fear of losing all my money and getting fired during the financial crisis. It was also a joy to write and watch the site grow through effort outside of work hours. After several years, the majority of traffic to this site came from Google.
When I left my job in 2012, for over 10 years, I have expected Google to eventually ignore Financial Samurai after one of their countless search algorithm updates. It’s a natural expectation after witnessing so many great independent sites disappear over the years. Yet, against poor odds, this site has continued to chug along, like a trusty tugboat navigating stormy waters.
From King Of The Hill To Minimum Wage
I feel especially grateful for this financial break after catching up with a friend who also runs a site. He recently hired the co-founder of another once-thriving site to handle sales for him. The base pay was minimum wage plus a percentage of revenue.
I was floored. That site, which had been around for over a decade and once regularly boasted over a million pageviews a month, is now a shadow of its former self. Due to Google’s algorithm changes, their traffic is down 90%, and the co-founders have had to pivot to stay afloat.
Now, I feel like my old-school approach of writing three posts a week myself with real-life stories isn’t so shabby after all. Although I constantly feel like the tortoise lumbering along against hundreds of darting hare, the enjoyable pace lets me earn supplemental retirement income, which I primarily reinvest in stocks and real estate.
Lucky Financial Break #5: Being Able To Invest In AI Near The Beginning
For years, I’ve treated my online income as “funny money”—a bonus that I didn’t rely on but instead saved and invested. Much like how rational people save or invest their tax breaks when they suspect the cuts might be temporary, I’ve been consistently funneling my online earnings into real estate and stocks. After 15 years those investments have grown thanks to a long bull market.
Now, AI presents another incredible opportunity to invest early in a transformative trend. While our children may not yet have the means to invest in AI today, we can invest on their behalf—and I feel a responsibility to do so. In 25 years, I don’t want them asking why I didn’t seize this opportunity, just as my dad once questioned my grandfather for not buying prime oceanfront Waikiki property when it was affordable in the 1950s.
Ironically, I expect AI to also hurt Financial Samurai by scraping my content and reproducing it without attribution. Then I expect AI to wipe Financial Samurai off the face of the internet, even worse than my expectations I have for Google. It’s funny how history tends to repeat itself if you live long enough.
Holding Onto The Final Years Of Existence
Since I can’t beat companies like OpenAI and Anthropic—with their deep pockets and armies of talent—I’ve made them work for me. I’ve invested in them and other leading AI players through venture capital funds, creating a hedge against the potential loss of online income. My goal is to invest enough in AI so that the gains from these private investments will surpass my online income over time.
Despite this site’s existential crisis, I’m cautiously optimistic that Financial Samurai can survive three more years, giving me until December 31, 2027, to reach my goal of full financial independence once again. If it does, I’ll be incredibly grateful for this final chapter in my journey. If the site doesn’t survive, then what a nice run it’s been helping over 100 million people achieve financial freedom sooner.
While it feels bittersweet to envision Financial Samurai’s potential end on December 31, 2027, it’s also liberating. A new chapter awaits—perhaps solely as an author or a 50+-year-old pickleball professional!
Related: Perpetual Failure Is The Reason Why I Save
You’ve Got More Lucky Financial Breaks Than You Realize
Take a moment to reflect on your lucky breaks. It’s easy to overlook them and attribute success solely to hard work and determination. Yet, a single fortuitous event can dramatically alter the course of your life. These moments are often the silent drivers of your journey—don’t take them for granted.
Let’s make the most of every opportunity our luck brings! Even if luck accounts for 70% of your success, that still leaves a meaningful 30% where you can try extremely hard. Thank you for reading, sharing, listening, and contributing over the years. It’s been a pleasure to connect and grow old with so many of you.
Readers, what are some lucky financial breaks you’ve experienced but may have overlooked? Is it inevitable to downplay the role of luck and overemphasize hard work and ingenuity in our success? How can we avoid confusing brains with a bull market so we—and our children—remain grounded and appreciative?
Investing In Artificial Intelligence
If you’re looking to invest in private AI companies, consider Fundrise Venture. Unlike closed-end venture capital funds, the Fundrise venture product allows you to see most of its investments before committing capital. With a low investment minimum of just $10 (compared to $100,000+ for traditional venture funds), it offers accessibility for a wide range of investors.
I recently invested another $5,000 into Fundrise Venture and plan to continue doing so for years. My goal is to capture potential liquidity events in the coming years, driven by acquisitions and IPOs. To do so, I’m building my position now, because such liquidity events are lumpy and take step functions up (or down) in price.
AI’s transformative impact is already evident—my dad lost his editing job, and my content is frequently scraped. These experiences reinforce my belief that AI will continue to disrupt various industries and reshape the labor market. My hope is that when my kids become adults, they will recognize their lucky break of having a dad who could invest for them.
Fundrise is a long-time sponsor of Financial Samurai, and I’m an investor in Fundrise. Remember, returns are never guaranteed, so always invest at your own risk based on your financial goals and risk tolerance. You can join 60,000+ others and subscribe to my free weekly newsletter here.
