He owns the majority of Gumroad. Let’s say he had 100 basis points of Pinterest, call it 50% dilution, he’d walk away with $50m. That’s probably very generous, probably actually closer to $20m.
Gumroad will be worth that in a few years at this rate, and he could cash million dollar paychecks along the way if he wanted.
So he'll be worth $50M in a few years with Gumroad. Meanwhile his original investors lost all the millions they invested. His employees lost all the time and vesting. Ouch.
That's why it's way to dangerous to just follow any guy and do a startup and waste a few years of your life.
> So he'll be worth $50M in a few years with Gumroad.
That's my best guess, yes.
> Meanwhile his investors lost all the millions they invested.
Well, some sold his equity back to him for $1, so yes.
> His employees lost all the time and vesting.
Well the employees could have exercised their grants when they were laid off, but I doubt they were inclined to double down on what was then a failing company.
> That's why it's way to dangerous to just follow any guy and do a startup and waste a few years of your life.
I mean, the employees got paid all along the way, and probably not that much less (if any) than they would have working for another company, and they got to work on something they loved.
Sad that it didn't work out. These things are risky, but having worked at startups and not gained anything from the equity I would do it again in a heartbeat.
The employees got paid less because of vesting. It is a gamble and this story shows different outcomes for employees. Pinterest paided off and gumtree didn't.
In both cases the founder made between 20-50 million.
Actually, his employees got a ton of experience building systems and processes the “hard way,” from ground zero at a startup. This inevitably made them more attractive to whomever they decided to work with afterward — startup, large company, whatever — especially as they were let go into a frenzy of hiring by other firms.
And if, God forbid, they wanted to start their own company and waste a few more years of their life (your words, not mine!), well... Everything is easier when you’ve seen someone else do it.
Gumroad will be worth that in a few years at this rate, and he could cash million dollar paychecks along the way if he wanted.