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What’s your biggest “what if” when it comes to finances?
Posted on 4/30/26 at 9:40 pm
Posted on 4/30/26 at 9:40 pm
I bought about $60,000 of Nvidia in a Roth IRA back in 2018. Admittedly, it wasn’t a “buy and hold” position for me at the time. I was just looking to make a little money after it dipped. I sold it a few months later.
Had I held it, it would be worth about $3 million in a tax free account today.

Had I held it, it would be worth about $3 million in a tax free account today.
Posted on 4/30/26 at 9:53 pm to DrrTiger
Financial advisor told me to sell some of my company stock because we had 6500 shares and options between the wife and I. No options were over $50 ish most high $20’s to $40 range. Sold 1000 to 1500 shares at $150 then wife got let go and we lost anything that wasn’t vested. Then it shot up to around $900 and split 4 ways
That and I should have sold game coin when I had 700k to 800k in that shite
Hopefully I have another 7 figure one coming up in 28 or 29 and need to play my cards right this time.
That and I should have sold game coin when I had 700k to 800k in that shite
Hopefully I have another 7 figure one coming up in 28 or 29 and need to play my cards right this time.
This post was edited on 4/30/26 at 9:55 pm
Posted on 4/30/26 at 10:05 pm to DrrTiger
I try to steer clear of the what ifs because that ish will drive you crazy
Posted on 4/30/26 at 10:05 pm to DrrTiger
My buddy tried to get me to buy Bitcoin when it was like $20-30. I laughed at his fake money nonsense
He didn’t hold long enough to become a crypto millionaire like Wiki Tiger, but he invested a couple hundred bucks and ended up selling for enough profit to put a pretty hefty down payment on a house.
He didn’t hold long enough to become a crypto millionaire like Wiki Tiger, but he invested a couple hundred bucks and ended up selling for enough profit to put a pretty hefty down payment on a house.
Posted on 4/30/26 at 10:05 pm to DrrTiger
Parents neighbor went bankrupt in 08-09, 1,250 acres of prime hunting grounds of I-10 in Kendall Ct, Tx. Turned down our first right of refusal.
It sold in 2020 for 18.75m. The guy that bought it, a friend of mine, put about 1.5m into the property and made over $16m.
It sold in 2020 for 18.75m. The guy that bought it, a friend of mine, put about 1.5m into the property and made over $16m.
Posted on 4/30/26 at 10:28 pm to DrrTiger
Never (almost, to be honest) do I ‘what if.’ Try to stick to objective, timeline for money and risk appetite. Once decision is taken, moving forward.
But I would be lying if I stopped there. I lived near Silicon Valley during dot com boom. Sold piece of real estate that made us a lot of money at the time (that was near early in career). Not too long ago, I looked it up. Multiple millions in value today, and not quite as high as your Nvidia regret.
So, you win!
But I would be lying if I stopped there. I lived near Silicon Valley during dot com boom. Sold piece of real estate that made us a lot of money at the time (that was near early in career). Not too long ago, I looked it up. Multiple millions in value today, and not quite as high as your Nvidia regret.
So, you win!
This post was edited on 4/30/26 at 10:40 pm
Posted on 5/1/26 at 6:09 am to DrrTiger
I have several. One that bothers me the most was not buying the Facebook ipo, which was around $38 a share. I thought about it and decided not to invest in it. I still don't use Facebook but I sure wish I had invested in their stock.
Posted on 5/1/26 at 7:25 am to DrrTiger
Not selling Gamecoin at the peak lol
This post was edited on 5/1/26 at 7:29 am
Posted on 5/1/26 at 12:08 pm to Tiger Prawn
quote:
My buddy tried to get me to buy Bitcoin when it was like $20-30. I laughed at his fake money nonsense
I had the same thing happen to me with Bitcoin but have been rapidly expanding my holdings in MegPrime based on what I'm seeing so far. It is the only crypto holding next to ETH that I'm holding.
Posted on 5/1/26 at 12:23 pm to DrrTiger
I bought a thousand LWLG at 1.21 and sold them at 2.16.
Had a chance to buy more at 4.20. THought it would head back down to 3.90.
Had a chance to buy more at 4.20. THought it would head back down to 3.90.
Posted on 5/1/26 at 12:41 pm to DrrTiger
Not investing more into vintage Pokémon cards during the pandemic. I knew the vintage sets were heavily undervalued.
Posted on 5/1/26 at 1:38 pm to Rendevoustavern
quote:
The guy that bought it, a friend of mine, put about 1.5m into the property and made over $16m.
You have to have money, to make money. (And be risk tolerant.)
This post was edited on 5/1/26 at 1:39 pm
Posted on 5/1/26 at 9:12 pm to DrrTiger
What if I bought gold @ 400oz instead of weed circa 2003.
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