This type of post only surfaced on the bull market, when greedily dragging the hardest people, which made it elusive. Since I made my first public stock investment in 1996, I have been fascinated by my investment decisions and fighting a constant psychological tug-of-war. Maybe you fight the same battle.
During the spring 2025 stock market crash, I deployed most of my rental home sales revenue to the stock market. I started buying too early (early March) just watching the stock keep falling. Still, I kept the dollar cost in mid-April. Ultimately, the market rebounded.
Of the gains I invested in March and April, there are about $500,000 personal Stocks are mainly technology. Of these, Meta made $40,000, which is my long-term holding of my rolling IRA.
My first SGD purchase was on March 10, at $591.76 per share. When it dropped to $488.50, I felt like an idiot, but provocatively bought more. My last dip-period purchase was $716.64 and then rotated to the value name.
Being a DIY investor determined to outperform performance, and active management can be very stressful. Unless you really like the investment process, it’s better to stick with a 100% passive index fund or ETF or hire a financial professional to manage your portfolio.
It takes a lot of investment to make a lot of money
I felt more stressed over two months and I was more stressed when I was doing a “C” on all SAT problems that I didn’t know. I also hope to drop 70% like I waited for the 30-second series of test results. Back to Goldman Sachs, failure will be humiliating.
All the time, pressure and effort put $40,000 into volatile technology stocks and five months later, I’m up 43%. That was a reliable return. But in the US dollar, it’s only $17,200 before tax. That hasn’t even covered half of the cost of my parents’ two-bedroom in-laws unit in Hawaii.
Yes, $17,200 is better than losing $17,200 in a bear market, but now it’s a bull market, so I’m looking to make a profit. But when I work hard to build more passive income, money doesn’t change my lifestyle. If I reinvest it in a 4% earnings asset, my annual passive income will only increase by $700. Several transportation tickets and passive income were eliminated.
Furthermore, unlike real estate, interesting monetary gains in the stock market can quickly evaporate given the richness of valuations.
As an active investor in my capital, I also suffered losses. For example, I currently Falling about $6,000 Since the stock level is $300, it has gone from dollar cost average to UnitedHealthcare. It was a disappointment when the S&P 500 entered the market.
The courage to take risks is elusive
Looking back, I should have invested in RMB in that window or leverage selection used. But I don’t want to bet. Government policies are highly uncertain and stocks are of high value. When growing stocks ride escalators, they tend to lower the elevator.
Fear of loss will naturally abandon one because of the huge reward. At least it has for me.
This is the dilemma: To be truly rich, you need to take huge risks. Without them, it would be hard to beat the crowd that mainly invests in index funds. But most of us are too afraid to take risks because we are afraid of losing more than we appreciate.
Read MBA students from the top 25 schools. They connect through case studies, analyze companies, and learn how to build a business. But what do most people do? They work in high-paying jobs in finance, technology or consulting.
After two years of loss of income and $150,000 in tuition, it makes sense to play safely. That’s what I did, once my MBA was done, back to Credit Suisse. Then it took me six years to finally make a leap of faith in 2012 and focus more on the financial samurai.
My biggest single investment slug
In Q1 2025, as the market fluctuates so much, I won’t invest more than $50,000 in single stocks. Instead, as the index fell, I bought mostly $2,000 – $10,000 for the S&P 500.
Then I made the largest single investment through the income, allocating $100,000 Innovation Fund. Because it is diversified among at least 13 private growth companies, I don’t think it’s over-risk. It’s more like investing $8,000 in each company in the fund.
In my podcast with fundraising CEO Ben Miller, I asked about the fund’s concentrated risks, as OpenAI, Anthropic and Databricks make up about 50% of their portfolio. Although I sound worried, the truth is I want more moneyAnd they are super-growth AI companies, and $100,000 in this space is a bet I’m very satisfied with.
Not going to get rich for $100,000
Sadly, investing $100,000 may not improve my life either.
In retrospect, I should have invested more innovation funds, as $100,000 is less than 7% of my home sales revenue. Now, humanity is worth $170 billion and Openai’s secondary population is $500 billion, and larger positions will create greater room for upward.
My venture capital target is usually 10-20% of investable capital, which in this case means $150,000-$300,000. But somehow, I just decided to make $100,000, probably because it sounds like a nice circular number. I didn’t think of things, especially when the stock market was saving.
This lack of consistency in investment is why the mandatory savings aspect of a mortgage-owned home is such a powerful wealth builder.
Quickly calculate potential $100,000 returns
If the fund offers a 25% IRR over five years, $100,000 grows to about $305,000, which is just over 3 times my money. In a decade, it became about $931,000, or 9.3 times. These are impressive numbers, but at 53, $305,000 won’t move the needle too much. Maybe I would splurge on the Toyota tundra in Honolulu, innocent, but that’s all.
$58, $931,000 can cover a complete remodel of my parents’ old house. But after my last gut transformation, I swear I will never do one again. It’s too painful and time-consuming.
More likely, I invest my proceeds in buying a completely remodeled home in Honolulu. That said, once I sold my primary residence in San Francisco and used tax-free exclusion benefits, I should have been enough.
Can funds actually be 25% per year on average over the past decade? That was a difficult task.
I want to own a $500,000 position
If I’m willing to save about $500,000 per child’s 529 plan, I should be equally willing to invest $500,000 in private AI companies that may make their college education obsolete.
Now, let’s dream: If I invested $500,000 and somehow got a 40% IRR for 10 years, that would grow to around $14.4 million. From a bet, it is indeed life-changing money.
For an additional $14.4 million I could fly privately, rent a luxury vacation home of $100,000 a month, buy a $200,000 family car, and donate $5 million to “help” my kids to go to college. How obscene! But that’s what the richest people have been doing.
question? Maintaining 40% IRR is nearly impossible without early stage startups or catching lightning in three bottles. Another problem is that investing 33% of my stable local income in venture capital is positive, especially when my target allocation is 20%.
In the context, the historical average return of the S&P 500 since 1926 is about 10%. Still…the dream is big.
The only real way to get rich is:
- Become rich and invest a lot to gain wealth.
- Invest large amounts of money in assets that have performed significantly for a long time.
- Build a successful business where you own a large amount of equity.
- Luckily – join the right startup, climb to the top of the rankings, or meet the right people to help you get a huge investment
Obviously, not everyone is born rich and has the courage to build a business or can invest big money into a risky adventure. Although luck is uncontrollable, you can take steps to increase your odds, such as moving to San Francisco during the AI boom.
So what is the solution? The continuous fence waving a certain percentage of capital.
Carve a portion of your capital for a high-risk bet
I found the best way to overcome the fear of high-risk investment is to put a small portion of the capital into practice and consistently bring it into positive opportunities. I recommend allocating 10% to 20%.
Take up 10% of your investable cash flow, savings or financial surprises and put it on the highest risk, highest return assets you can tolerate. If you lose all of this, you’ll only lose 10%. But hit something 10 or more and it will move your overall wealth into the needle.
As wealth grows, instinct is to play defensive and protect capital. After all, you don’t want to be forced to return to the “salt mine” during the next recession. But boycotting everything is too conservative. Keep 10% – 20% of high risk buckets.
Some sample allocations:
- 25 years old, $50,000 to invest: $5,000 speculative, $45,000 S&P 500
- Age 30, investment of $200,000: $20,000 speculation, $170,000 S&P 500, $10,000 liquid
- Age 35, investment of $500,000: $50,000 speculation, $250,000 S&P 500, $200,000 Real Estate, $50,000 Liquid
- Aged 40-60 years old, can invest $1,000,000: $100,000 speculation, $600,000 S&P 500, $250,000 Real Estate, $50,000 Liquid
Or get a percentage of monthly savings. If you save $5,000 per month, put $500 into the speculative bet. In more than a year, it’s $6,000. As your income and savings grow, so do bets.
Practice to relax high-risk capital
I have considered the child’s hosting account, Roth IRA and 529 plans as no longer mine. This mentality makes it easier to have a stomach sluggish and keep the course. In fact, whenever the stock market goes down, I become rebellious and actively invest in my kids’ accounts to help them build their wealth.
Apply the same strategy to high-risk investments. Once you put in that money, it will be psychologically produced. This is easier when it only accounts for 10-20% of capital and you still have other 80-90% security. This detachment makes it easier to place bets, keep them for longer and avoid panic for sale.
Align with your active investment
The formula for building a serious wealth is simple, but uncomfortable: invest in large sums, earn high returns and repeat consistently. The real challenge is to maintain the discipline to make the high-risk buckets funded year after year.
Automatically contribute to your brokerage accounts, open-end venture funds and other investments. As time goes by, this steady drop adds up.
Reader, do you suffer from greed and dissatisfaction in this bull market? How do you make sure you are always investing and looking for potential multi-bag opportunities? And, if you don’t chase life-changing money, how did you achieve what you really have? What guardrails do you use to avoid the risk of overextending bets?
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