What’s your deepest secret regarding your company that you haven’t been able to share with anyone?

  • I should have never cofounded a company with my brother. It nearly ruined our relationship because I didn’t want to hang out with him outside of work after spending 60+ hours together every week.

  • I regret having spent 5 years building it, still getting $0 salary, only to have my co-founders not follow through by doing next to nothing. I regret having my wife work with us (DO NOT EVER DO THAT).

    Most of all, I regret founding a company with a good friend. Because we WERE friends, I waiting way too long to call him on his complete lack of follow-through.

    … and I haven’t let go yet because I’m afraid.

  • It looks like most answers here are because you are having a difficulty to make a hard decision, to fire your brother, friend, wife or to let go of projects that you shouldn’t be working on. My advice to people with relationship issues is: Communicate. I can’t stress this out enough. Discuss the situation, be firm about your beliefs, and politely ask them to go. You don’t need to do much other than that.

    For people who are having difficulty letting go, one of the best things you could do is take some time off to think and reflect. Taking time off is a compromise, with less consequences than you may be afraid off. Just take it, think, reflect and pivot.

  • The importance of deeply thinking and clearly articulating what it is the company will stand for (it’s raison d’etre), and having the guts and determination to stick to it.

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