Originally, I planned to title this post, “Getting Rich by Getting Lucky Doesn’t Feel So Good.” However, after some time, I realized that getting lucky actually feels better over time! This change in sentiment has profound socioeconomic implications, as it may lead us to hoard our wealth and create more inequality. Luck may also lead us to delusion and subsequent experiences of disappointment.

On May 10, 2024, I got rich by getting lucky—not in a monetary sense, but in a feeling of richness from a USTA tennis league match. My doubles partner and I lost the first set 1-6, as we couldn’t consistently return our opponents’ big serves. During that set, I thought we would need a miracle to win the match.

Then, in the second set, a miracle came. Our opponents were serving at 2-3, and at 30-30, we had a long 12-shot rally. After the point, one of our opponents started hobbling. He went over to the fence to stretch his calf, and we gave him extra time to rest.

Our opponent said he heard a pop but felt no pain. Instead of forfeiting the match, he valiantly continued, limping around the court.

In the end, we beat them 6-2 in the second set and 10-3 in the tiebreaker. Although we were playing better before the injury, it was highly uncertain whether we would have won the second set and tiebreaker if our opponent had been healthy.

In other words, we got lucky. At this point, my record was 5-0 with half the season over, and I felt like it was time to retire.

Mixed Emotions Of Winning Through Luck

I’ve played over 100 USTA league matches since 2009, and I’ve never experienced anything like this. I have hoped to win by forfeit in the past, as playing at the 5.0 level against ex-college players was brutal, but my opponents have never given up.

Initially, I felt guilty about winning against an injured opponent. Then, over time, I felt relieved. As the days passed, I slowly started believing I deserved to win. I told myself things such as:

• I was 4-0 before the match, so I was already winning.
• To defeat your opponent, you must last to the end, not halfway through.
• The opponent could have retired, but decided to fight on.
• I practiced twice that week for the match and didn’t just wing it.
• I was at 75% capacity when I played because I was sick.
• My opponents were 12 and 13 years younger than me.
• Eventually, I’ll get unlucky as well, so I might as well accept my good fortune when it comes.

Isn’t it interesting how we oftentimes justify our lucky breaks even if not fully deserved? Let’s touch upon how justifying our victories can be dangerous.

A Similar Feeling To Getting Hired Based On Identity Or Legacy

I’ve touched on the diversity hire dilemma in a previous post.

On the one hand, you absolutely want all the benefits like higher pay and bigger promotions wherever you can get them. The world is brutally competitive enough. If an organization wants to pay you above market rate simply due to your identity, then great! It’s a free market!

On the other hand, if too much of your reward is due to your identity and not enough to your merit, you might feel overwhelmed with guilt. In a small organization, where there’s nowhere to hide, the pressure to perform will be immense. Eventually, you might start feeling like a fraud and an abject failure.

The beauty of sports lies in its strong correlation with merit. Sports doesn’t care who you are or what you look like. You either practice, strategize, and win, or you lose. It’s also why I love to continue competing. This clear and immediate outcome is why you don’t see a strong movement toward more diversity in sports.

As a result, if you do not strongly believe in your own abilities, DO NOT become a solopreneur or entrepreneur. You will be exposed because business competition is too cutthroat. Do not join a start up or any other type of small organization either.

We already see that ~90% of venture capital-backed companies fail, and these companies employ the “best and brightest” people. If you’re not one of them, your chances of success are infinitely smaller.

On Taking The Money And Running

During the pandemic, I spoke to someone who capitalized on the nation’s mood by signing a $400,000 book deal. Based on her platform size, she should have received closer to a $50,000 book deal according to a couple of top literary agents.

Sure, she felt a little sheepish to get so far above industry standards. However, she told me, “If the publishing industry wants to pay me this much in a bidding war, who am I to deny them? I’ll gladly take the money and see what I can do. If the book does well, then wonderful! Everybody wins. But if the book doesn’t, then it’s not my problem because the publisher decided to take a chance on me.”

In the end, the book was a commercial failure. It sold 1/20th of what the publisher had expected. She may never get another book deal, but it doesn’t matter because she received 8 times what she should have received. So in reality, it was like getting eight book deals!

If you get lucky, take the money and run. If you don’t, someone else will. Nobody is forcing an organization to give you more than you deserve.

Beat The Person Who Rejected Me

In my tennis match, the injured opponent was actually the captain. In early 2023, I had asked to join his public park team, but he said he didn’t have room. I was disappointed because he was a good guy, and I had played on his 9.5 team in 2021 with a 3-2 record.

So, beating him felt special, but not in the way I wanted due to his injury. If he had accepted me on his team last year, I would have played on his team this year. And if I played on his team this year, he wouldn’t have lost to me and my partner.

In other words, take what you can get, and savor the victory against someone who rejected you before. Because goodness knows, the more you put yourself out there, the more you will get rejected.

It’s Nice To Get Lucky Some Of The Time, But Not All Of The Time

There’s an old saying, “It’s better to be lucky than good.”

I empathize with this saying because I’m no longer as good a player as I once was. At almost 47, my photoreceptors have declined, making it harder to see the ball at night. My power and quickness are also down by at least 15% from 10 years ago. As an aging athlete who still competes, it’s sad to get old.

Given my disadvantage, I welcome some occasional lucky breaks to help level the playing field against younger opponents. However, I don’t want luck to ever account for more than 10% of the reason why I made money or got a win. I’m good with the occasional lucky break that might give me a 10% boost during times of need. Otherwise, I’m happy to battle straight up in sports, investing, business, and the like.

It’s simply not as satisfying winning due to luck, connections, identity, or any other unfair advantages. This is why if you are born with a disadvantage and get ahead, you’ll feel much better than someone who was already born with everything.

Life Is Never Going To Be Fair

However, the reality is, the world is rigged. People have unfair advantages all the time. And many of these people with unfair advantages also get lucky! As a result, don’t feel bad when the occasional lucky break comes your way. Because goodness knows, there are a lot more lucky and undeserving people out there than you.

Trickle down economics doesn’t work because everybody has enough greed in them to keep most of what we have, even if we gained most of it through luck. Just think of all the billionaires out there who are willing to hold onto their wealth even upon death while people on the streets suffer.

MacKenzie Scott, the ex-wife of Amazon’s Jeff Bezos, is a rare individual who donates aggressively and frequently. It’s quite apparent that MacKenzie recognizes how fortunate she is and wants to share that good fortune with as many people as possible.

Take What You Can Get If You’re Willing To Compete

As I come to the end of this post, I no longer feel guilty about defeating my opponent who got injured and rejected me. We all battled to the very end, and my teammate and I got a lucky break. Eventually, we will also get unlucky, and that’s just the way things go.

The key is to recognize the luck we’ve had in our lives and not confuse brains or skills with luck, i.e. don’t be delusional. Instead, try to take our good fortune and make it last as long as possible.

My luckiest financial break was buying a stock called VCSY in 2000 for $3,000, which then went up 50X to $150,000 in six short months. I knew I was lucky because the Dotcom crash wiped away all gains for almost all internet stocks over the next couple of years.

To extend my luck, I sold VCSY and parlayed the funny money into a real asset, a 2/2 condo in San Francisco that I still own today. The condo is paid off and every electronic rent deposit is reminder about getting lucky as a young lad, and not take the good fortune for granted.

Owning real assets that will survive long after we’re dead is one of my favorite ways to preserve wealth. I suggest you do the same.

Extending The Luck That I’ve Experienced Online

Today, my luck may be running out with Financial Samurai.

I made a promise to publish three posts a week for 10 years starting in July 2009. Although we’re well past July 2019, I continue to publish three times a week, partially because I sense my mortality. With fading eyesight and fingers slowly becoming more arthritic, I don’t know how much writing I have left in me.

I need to type now while my brain still works, just as I need to compete in USTA tennis before my body no longer allows it. My window of opportunity is closing fast. Perhaps, like me, you become more sensitive to your mortality as you get older.

Financial Samurai has grown about 10X larger than I first imagined. However, with the emergence of artificial intelligence ripping off content creators and Google changing its algorithm to show more of their answers, the online publishing world is only going to get more difficult.

Investing Aggressively To Overcome Bad Luck

Given this recognition of change online, over the past three years, I’ve reinvested 96% of active online income into a new primary residence, private AI companies, Google stock, and private real estate funds.

Yes, that’s right. Since I can’t beat AI and Google, I might as well join them as a hedge. The battle for tech supremacy is fierce. I will not get left behind. By reinvesting my online proceeds, I’ll be able to make my online luck last longer.

If you get lucky, you will feel richer. Embrace it. Everyone deserves some good fortune on occasion. As long as you are consistently trying your best at whatever you do and willing to battle, there’s no shame in getting lucky once in a while!

Reader Questions

Have you ever gotten rich by getting lucky? What lucky breaks have you had in your life that made you feel a little sheepish at first? How did you overcome any guilt you felt from the luck you received? What is the best way to make more people lucky? Have you ever decided to work harder, even when you didn’t have to, just to feel like you earned your luck?

Get Luckier By Investing In Real Estate

Although luck plays a big part in building more wealth than average, you still have to take risks. Investing in real estate and the S&P 500 have proven to be long-term wealth creators.

Check out Fundrise, my favorite private real estate platform. Fundrise runs private real estate funds that predominantly invests in the Sunbelt region where valuations are lower and yields are higher. Its focus is on residential and industrial commercial real estate to help investors diversify and earn passive returns. 

Fundrise currently manages over $3.5 billion for over 500,000 investors. I’ve invested $954,000 in private real estate funds since 2016 to diversify my investments and make more money passively. After I had children, I no longer wanted to manage as many rental properties. 

Invest In AI And Private Growth Companies

Given I expect AI to wipe away millions of jobs and make life more difficult for my children, I’m investing ~$500,000 in various private AI companies. Check out the Innovation Fund, an open-ended venture capital fund that invests in leading AI companies like OpenAI, Anthropic, Databricks, and more.

Roughly 90% of the Innovation Fund has exposure to artificial intelligence, which I’m bullish about. The investment minimum is only $10 versus $100,000 or more for closed-end venture capital funds.

Financial Samurai is an investor in Fundrise funds and Fundrise is a long-time sponsor of Financial Samurai. Getting Rich By Getting Lucky is a Financial Samurai original post. Everything written is based off firsthand experience because money is too important to be left up to pontification.