The only thing harder than making a ton of money is giving it away to family.
On paper, it sounds easy. We've finally got some dough and now we can hand it out like Robinhood to all the people in need. What could feel better than helping our family with a little extra cash?
That's until we find out what a giant tangled mess of problems it tends to create. What we are thinking about is how helpful we can be, but what we're not thinking about — and where most Founders live in regret — is what a can of worms we open from here on out.
The problem with giving away money once is that once we open those floodgates, they are nearly impossible to close. All it takes is a single act of kindness to send those gates crashing open.