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3 mistakes kept me stuck at $30M

@jayhoovy
3.3K views197 likes1:04ENAug 17, 2026
257 words1383 characters13 sentencesReadability: High School

Transcript

Here are the three most brutal mistakes I made during a startup so you can avoid them yourself. Number one is I didn't take enough time off. We were stuck at 30 million dollars in revenue and my natural reaction was to lock in and try to fight the fires, but instead if I just taken two weeks just to breathe and zoom out, I would have figured out the answer way sooner, work exceptionally hard, but also know when you should take time off to rest recover and upload. Number two is I didn't trust my team enough. You as a founder are the start player when doing all the sales, doing all the marketing, making all of the product decisions. But this actually gets in the way of you eventually scaling. Instead it's to hire great people and not do what I did initially, which is to micromanage every single decision they had. And then lastly is I cared too much. I'm going to be hyper obsessed over this. I'm simultaneously holding this obsession with also this level of detachment of like, yo, if this thing doesn't go well, cool. That's okay. This kind of dual mindset ultimately leads you to be a CEO who can make the best decisions without all the emotional reactivity in the moment. So make sure you take time off so you can see the chessboard clearly, trust your A players to do what you hired them to do, and then find the right balance between obsession and healthy detachment.