I came across this X post and it brought me to think about the lifestyle and time economic tradeoffs between the two roles of Operator vs. Investor. Nothing wrong with any of these roles, but one thing that comes to mind for me is career endurance, especially when some of these angel investments can take over a decade+ to materialize.
At what point do top corporate executives burn out and rotate into an investor role? How many folks transition from investor to operator and vice versa? I think deeply about these questions because, in the end, I think it’s up to the preference of each individual and how they’re looking to allocate their time and energy portfolio.
Check out some of these great comparisons between a CEO operator and a GP fund investor that I got from ChatGPT below.
Based on these comparisons, I feel like being the software investor in all of this economy role architecture isn’t so bad (this is my bias :)). Anyway, check out some of the returns below from an old WSJ post related to the angel investors who pocketed big from Uber’s IPO. This list of returns is awesome, but if I recall correctly, Jason Calacanis made this Uber investment when he was ~38-39 years old (born in 1970) back in December of 2009, and later Uber IPOed in 2019. That’s a whole decade, folks!
List of Angel Investors in Uber
Uber’s Seed Round took place back in August of 2009
Uber IPO Date
Quick Google Search on Jason’s Birth Date
