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#1. Acquiring Bitcoin at $6 and selling at $1,000 -$713 million
Young me did not believe strongly enough in exponentials. A 100x gain could have been a 6,000x gain. ~98% of upside missed.
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#2. Buying NVDA in 2014 and selling in 2017 -$5.8 million
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#3. Acquiring Ether at $10 and selling at $20 -$2.8 million
Note: DAO bit was a joke. Never did find out what DAOs were.
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#4. Going long TSLA and selling for only a 50% gain -$330,000
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#5. If I had sold zero of my 365 AMD shares this $1,010.70 would be $224,664.80 today. -$224,664.80
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UPDATE: NEW PLAN!
Problem is true venture investors never stop looking for next thing, and their winners, while awesome, become less interesting (because 1 to N is less interesting to people obsessed with 0 to 1).
Lesson is: if you are an early stage investor, sell 10% of your remaining shares every single year (and no more).
You can eternally search for and fund new things but will maintain significant stakes in your winners:
- after 10 years you'll still hold 35%!
- even after 30 years you will still have 4% left of your stake!
The 2026 auction for a 10% stake in SellNothing.com is now open.
⁂