alt Hacker NewsI dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction.
Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me.
F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
Speaking as a co-founder CTO, I believe there is a very insidious kind of attachment that forms when you’re dancing with burnout, and working on a successful company that you’ve built from the ground up.
“I want to leave a dent in the universe” I told myself. After 3 months in a hammock decompressing, I very quickly realized that there is more to life than work, and it’s really easy to find fulfillment building things if you get bored. But this viewpoint is really hard to hold onto when you’re buried in the day to day excitement of the job.
> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
At least for me, regular financial decision making breaks down once the numbers are above a certain amount.
E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall.
The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on building.
That’s the route I took. Paired with obsessive focus on work/life balance, I don’t regret taking this route.