Hey Shae!
Yes, tripling your money in Amazon is awesome. But that is what I would call “getting lucky”. Study after study after study after study show that it’s basically impossible to consistently pick stocks that will outperform the market over time. So when you pick an individual stock, you don’t get a higher expected return, but you do get higher expected volatility (up and down). What if (for example) you KNEW that MySpace was the future of the world, social media was gonna take over and you want to ride that wave and put all your money in MySpace. Well, now your Roth IRA would be worth $0! That’s what we call “risk”. And normally when you assume more risk you deserve a higher reward. That’s why people invest in the stock market instead of savings accounts. But with individual stocks you’re assuming more risk than an index fund without a higher expected reward. (But you still can get lucky)
THAT SAID, investing in individual stocks isn’t BAD. After all, an index fund is just made up of individual stocks. If you invest early and often in 20-30 different individual stocks over the course of your career, I’m sure you’ll do great. But I would bet at the end you’ll have less than the index fund route.
And for sure, if you want to become a billionaire you have two options: Start a company or inherit it. But for every Jeff Bezos there’s a million failed/broke entrepreneurs out there. Some of it might be luck. i.e. if you flip 100 different coins 100 times each and ONE of them turns up heads 98 times you could point to it and say “See. I should just flip a coin to get a bunch of heads”. But that’s not going to be repeatable.
So: Tried and true, mathematically buying and holding index funds is most likely to optimize your future wealth from the cash you invest. BUT if you want to pick a few stocks, go nuts. Use the 90/10 rule (90% buy and hold index funds, 10% go nuts). If you’re so good at picking stocks, your 10% will quickly outpace the 90% anyway. And if you happen to pick a MySpace next time, at least you’re not broke.
And if you want to start a company, go for it! Like I said, that’s the only way to become a billionaire unless you have some rich parents you didn’t mention.