At 16, I never had a manager before, so it was hard to model what that would look like for managing my team. At YBC, I managed a staff of 20 writers, and when I was unsatisfied with articles, I would often bury my concerns and compensate by spending more time editing them. When I disagreed with my cofounder on scaling or content strategy, I often preferred to avoid conflict. Consequently, problems weren't fixed quickly and tensions quickly rose.
To reinforce this idea, I chatted with Danielle Strachman, General Partner at the 1517 Fund and cofounder of the Thiel Fellowship. She works with and funds young founders all the time, and, from what she's seen, she tells me, "I've seen cofounders split over not communicating enough and focusing on the same goals. It's really sad to see a team that starts out as friends turn against each other, but it happens."
Though I'm still friends with my former cofounder to this day, the time sink associated with not communicating and the hurdles we could have avoided are testament to the importance of addressing concerns early on. Whether it be a misalignment of values, a difference in priorities, or difficulty fundraising, these conversations are never fun to have. But putting them off doesn't do anyone any favors either.
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