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1/ I became "CEO" at 20. I dropped out of college. I had only interned somewhere prev. Looking back, I couldn't imagine the journey that would occur from writing code all day to scaling to 300 people. I got lucky, I screwed up a lot, & had a lot of help. Here's what I learned...
2/ Giving up control is hard & it was the hardest for me. I felt like everything at the beginning was important. You can't be good at everything tho. As you grow, I learned it's important to conciously give up things constantly. If you don't, you won't scale & everything suffers.
3/ Your VCs won't want to offend you so I'll suggest it: get a CEO coach & do a 360 review of yourself every few years. It was life changing for me. You can’t fix everything about yourself. Focus on 2-3 things each year. Tell your company you’re doing it. It'll build trust.
4/ Over time, you will feel like all you’re doing is spending time in meetings but not getting any real work done. You are though. Your job is now helping other people through the medium of meeting. Don't resist it, embrace it. Now's the time to design it to be fun & productive.
5/ Find a great mentor: Pick someone you want to impress. Find someone who will lift you up when you're down & take you down a notch when you're over confident. Ideally, they've been a CEO/founder before so they can empathize. Remember though: they offer guidance, not a script.
6/ Live by the mantra: “you should be building a team that can fulfill the mission without you.” You will be less stressed in the long-run. Keep empowering others. When you forget, try & ask yourself why you started this thing in the first place. Was it really about $$/power/ego?
7/ Power = responsibility. Being CEO will become lonely as you can't be as vulnerable & authentic as you'd like. Find other founders who will be real with you. Have dinners with them & share problems openly. I've been given hugs by them during tough times. It made the difference.
8/ Don't avoid confrontation with tough, critical decisions--deal with it head-on. Avoiding confrontation, builds resentment over time, it slows the company down, & relationships eventually turn sour in a irrevocable way creating instability. Attack problems, not people though.
9/ You will royally screw it up with people in your company even if it wasn't your decision. They may even dislike *you* for a long time. The words “I am sorry. I screwed up.” are some of the most powerful words you can ever say to someone. It won’t always fix it though.
10/ Your job will become 90% listening, 10% talking. I was bad at this & had to work 2x as hard at not interrupting people. Best solution I found after 9.5 years was to write things down during a meeting. It made me focus on what they were saying & showed I was listening.
11/ Your intuition about customers/the market will get worse as the organization grows & you become further estranged from customers. Keep empowering others but hold them accountable. Spend time learning from them. Stick to the facts, not their opinions when making decisions.
12/ Discovering the truth becomes hard as you grow. It also becomes the most important thing you can do as you guide the company. Make acquiring it & using it for decision a part of the culture somehow. I did this by constantly asking people what the actual facts were.
13/ Control your mood meeting-to-meeting. Sometimes you will have a bad/devastating meeting but try to remember that the next set of people don’t have that context & may be excited/stressed to meet with you.
14/ We’re all human & have our insecurities so consider a therapist to assist in helping with your personal psychology. If you associate a stigma with it know that I did too. I was wrong & wished I had done this earlier in life. It will be invaluable if you tend to bring it home.
15/ Finally, keep working hard to improve. You can’t fix mistakes of the past but you can be better in the future. Don't give up: when you make hard decisions, you get to know which values/principles you truly stand for. That alone makes the journey worth it. ✊
If you haven't read it already, check out this thread of mine on fundraising too:
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