For a start-up CEO, here’s my list, force-ranked:
1. Spend more of your time recruiting VPs and your senior team — and help in general. At least — 20% of your time. Your life will be much, much, much simpler once you have a great VP for every core functional area. If you are lacking one — stop hacking it. Hire the real deal.
Probably, we can stop right there. This could be 1-5.
But my next best 4, FWIW:
2. Get one great mentor. On your board, as an advisor, whatever. That can truly spend real time with you — both tactical and strategic team. Quantity over quantity. Someone that’s done it at least 2 stages successfully ahead of you. And that you trust. She’ll spot all the issues and pitfalls before you do. She’ll be right 80-90% of the time. She’ll challenge you. And she’ll back you. And help you see when you are actually doing better than it looks. (And don’t cheap out on equity here. Or she’ll help in the beginning, but then drift away.)
3. Fire whomever is truly dragging you down. Get rid of them. Tomorrow. Even if you can’t survive without them in your org chart. Better to find a way without them.
4. Raise 30% more money than you planned. This will dramatically de-stress your life. You’ll have a buffer. I know you don’t think you need it. But everyone, in the end, does. You’ll at least get to make that one extra great VP hire (see point 1 above), hire than extra engineer. Whatever. 30% more.
5. Say Thank You more. And Fix what you break. As a start-up founder, you’ll break a lot of stuff. Often unintentionally. You can’t fix it all. But fix what you can. Apologize. Give out extra options if you screwed up. Give a raise you forgot to make — and true it up. It’s a long game. Treat people right, and it will benefit you on many levels. You’ll make mistakes. We all do. Just fix ’em when you can.