That’s the thing though, we all do have a crystal ball. It says buy a broad basket of stocks, hold them for a long time and you’ll have a lot more money than you started with. The nominal return on the S&P 500 since the mid 1960s has been over 30,000%.
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Probably some old timers wish they had bought BRK.A for $19 per share in 1965.
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GME. I came across reddit posts about people buying and holding it in late Dec 2020. Before Billionaire tweets or press stories. But I’m not part of the population that trusts what is posted on social media. Probably would have sold it too early anyway.
Back in around 2015/2016 my then 16 year computer nerd son came to me and said that there were two vastly undervalued tech stocks that he wanted to invest in. After some deliberation, my husband and I decided to let him invest some of his bar mitzvah money thinking it would teach him a lesson about the stock market. Maybe he would make a little money, maybe he would lose some. Those stocks? Nvidia at $22. It has since split twice at 4 to 1 and most recently 10 to 1. The other AMD at $2. He has made something like a 3000 percent return. Not quite the lesson I thought he would learn. I invested in both about two years later, but wish I had listened to him sooner. 
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Is he retired ?? 
Congrats to both of you. He did better but I’m sure you both did well.
No. His initial investment was less than $10k, but he is in great shape for a 25 year old. We didn’t make a huge investment either, we leave that to the financial professionals.
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Our son bought, “a,” Bitcoin (maybe in 2015/2016??) for $425.
He did sell half of it (at a nice profit at the time) to fund his post college, pre-job, SE Asia trip. But, he would have been better off not selling it.
Timing was good, tax-wise because he paid no capital gains tax because he had no other source of income.
We thought it would be a good lesson for him as well. 
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I remember when my father called me and asked if he should invest in Apple. He knew I was a computer guy and had used Apple. This was when it was at its low point with only PCs as a product line, Jobs long gone and not yet back, down to less than 3% of the PC market and losing ground. And frankly its products had sucked lately – freezing with the bombs icons all the time, dropping support for products every couple of years, etc…
So I talked him out of it. 
I also talked someone out of buying Google at the IPO and talked myself out of buying Amazon in the late '90’s.
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My darling child who told me to buy Nvidia and AMD in 2015 was also obsessed with mining dogecoin around that same time. He was running up my power bills and the computer was literally heating up the house. I had screaming matches with him about how stupid it was and that doge would never be worth more than what I had paid out in power usage. I later learned he had also rigged his school’s computer system to mine for him as well. Lol. Shortly after his seventeenth birthday, he received 2 speeding tickets within weeks of each other. The tickets were $500 a piece and we had to hire a lawyer. I told him he would be paying for that. He cashed in $2500 worth of dogecoin to cover it. A couple of years ago when doge suddenly took off(thanks to a couple of tweets from Elon Musk), kiddo informed me that the doge he cashed in would have been worth $450k. Lesson learned: he no longer speeds. 
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“What stocks didn’t you buy…but wish you had bought?”
Lots and lots including Chipotle and Taiwan Semi, AMD.
I also bought lots of stocks I wish I hadn’t bought!
However, I also bought a lot of the right stocks so not too much regret here.
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Our family story was when my mom’s school system gave her a check for a few thousand dollars to make up for short changing her salary for a few years. She wanted to invest it in a new computer tech company. My Dad convinced her to put it in bonds.
The company was Microsoft - in the 1980s…
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Ugh
I remember thinking hard about buying Netflix back when they were still just shipping DVDs, but I never pulled the trigger. Also thought about Amazon in the late 90’s but I was like, “nah, they’re losing money and who makes money selling books anyway?”
I remember deciding to spend a few hundred on bitcoin when it was about $100. But as soon as I started reading about digital wallets and exchanges I gave up in frustration as I just didn’t have the mental energy for it and the whole thing seemed shady.
After those missed opportunities I decided to indulge my investing whims more, and got lucky buying nvidia about 4-5 years back when I heard automakers were using their chips for apple and google carplay. I completely forgot about that purchase until AI started making headlines last year. So I bought the right stock for the wrong reason - shows how much I know.
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We bought a ton at the wrong time and now wish we had been using broad index funds all along. We did buy a few good ones along the way, Apple, Berkshire B, Nike, and a few more. 
Never had any regret regarding stocks, but have regrets regarding land.
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