Kevin Hart and Mark Cuban shared their regrets over passing on the chance to invest in Uber during the company’s early days — a move that haunts Hart “until this day.”
Chatting on an episode of Hart’s talk show, Hart to Heart, the actor and comedian said he scoffed at investing in the ride-sharing business because the idea of strangers picking up strangers and driving them places sounded “like Murderville” to him at the time.
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“This makes me so mad,” he told Cuban, reflecting on his decision.
Hart says he was asked to put $50,000-75,000 into Uber —an investment he estimates would now have been worth more than $100 million.
Cuban had it even worse. The American businessman and investor was approached by Uber co-founder Travis Kalanick to invest in the early stages of the company — but Cuban thought the initial valuation of $10 million was too high. He offered to invest at a $5 million valuation, but never heard back from Kalanick.
Both men regret their decisions. Uber now operates in more than 10,000 cities worldwide with a market cap of over $90 billion. Cuban moaned: “If I [had] given him $250,000 on a $5 million or $10 million valuation, it’d be [worth] billions.”
Getting the inside track on private, early-stage golden investment opportunities is often only available to high-profile investors or celebrities like Hart and Cuban.
Here are three tips that every retail investor (whether you’re a beginner or more experienced) can make the most of — and while they might not make you billions, they can set you on a positive path.
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Don’t be afraid to seek advice
Unlike investing juggernauts Hart and Cuban, everyday investors don’t typically get tips from business leaders that could grow into millions of dollars.
But you can work with a professional financial adviser to get a leg up on the hottest deals.
Financial advisers can answer your questions, help you to understand complex investing terms and provide you with reliable information on the stock market and the wider economy. Their advice expands beyond investing to wider financial planning and money management.
If you don’t want to work directly with an adviser, there are lots of investing apps and online platforms that will do much of the work for you — and some only require a small investment to get started.
Read more: Thanks to Jeff Bezos, you can now use $100 to cash in on prime real estate — without the headache of being a landlord. Here’s how
Diversify with index funds
One of the first things that many financial professionals tell beginner investors is to diversify your portfolio with different types of assets and exposure to different sectors.
One easy way to do this is to invest in index funds. An index fund is a mutual fund or exchange-traded fund that tracks the performance of a specific market index, such as the S&P 500 or the Dow Jones Industrial Average.
The fund includes a representative sample of stocks or bonds from the index it tracks rather than hand-selecting them. They’re typically less expensive to invest in than actively managed mutual funds.

A fund that tracks the S&P 500, for instance, is supposed to give you exposure to 500 different companies — but your investment will be skewed toward the firms with the largest market caps, meaning you could be more exposed to certain sectors, such as technology, than you might realize.
Generally, index funds have performed well in the past. From 1957 through Dec. 31, 2022, the S&P 500 delivered an average annual growth rate of 10.15%, according to Official Data. This has been excellent for long-term investors — but as with all things investing, it’s important to remember that past performance is not an indication of future returns.
Maximize retirement accounts
When building your wealth and planning for your financial future, you should consider using tax-friendly investment vehicles like a 401(k) account if your employer offers one.
A 401(k) retirement savings plan will allow you to steer a portion of your pay into an account where you can invest and grow your money — and get a tax break.
If you don’t have access to a 401(k), you might consider opening a traditional individual retirement account (IRA), where you can contribute pretax income and grow it tax-free until you make withdrawals in retirement.
You’re allowed to contribute up to $7,500 in a 401(k) and up to $1,000 in an IRA in 2023.
Another option is a Roth IRA, where your contributions are taxed upfront so that your withdrawals are tax-free in retirement. Roth IRAs are popular with experts like Dave Ramsey for their advantages and flexibility, but they do have certain rules and limitations and you can face penalties if you withdraw your earnings too soon.
The good thing about all of these accounts is they allow you to grow your wealth and put your money to work by investing, giving you needed cash flow in your golden years.
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