You are willing to sell.
Scenario #1: Company goes out of business
Lets say you are completely right.
$100K in 2017's dollars > $0 in the future.
Verdict: Sell
Scenario #2: Company struggles/downrounds/etc
Your stock is diluted.
$100K in 2017's dollars > $100K (or less) in 20xx dollars.
Scenario #3: Company is moderately more successful than expected
$100K in 2017's dollars ==(approximately) $150K in 2020 dollars
Scenario #4: You are completely wrong
$100K in 2017's dollars < $1MM in 2020 dollars.
--------------------------
You left the company for a reason. Has any of those reasons changed?
Maybe sell part and keep part to reduce regret possibilities?
Question: What number will you be emotionally o.k. with no matter the result?
You are willing to sell.
Scenario #1: Company goes out of business
Lets say you are completely right.
$100K in 2017's dollars > $0 in the future.
Verdict: Sell
Scenario #2: Company struggles/downrounds/etc
Your stock is diluted.
$100K in 2017's dollars > $100K (or less) in 20xx dollars.
Verdict: Sell
Scenario #3: Company is moderately more successful than expected
$100K in 2017's dollars ==(approximately) $150K in 2020 dollars
Verdict: Sell
Scenario #4: You are completely wrong
$100K in 2017's dollars < $1MM in 2020 dollars.
--------------------------
You left the company for a reason. Has any of those reasons changed?
Maybe sell part and keep part to reduce regret possibilities?
Question: What number will you be emotionally o.k. with no matter the result?