6 years ago I joined a 20-person startup. I wanted to quit after my first week, but I didn’t. Now our company is worth over $1B and has 200+ employees. Here’s what I’ve learned about succeeding at a startup:

1) Startups are HARD. The work has never been done before, so you will constantly feel like you have no idea what you’re doing. And you might not. This is uncomfortable, especially if you’re a perfectionist.

2) There’s a massive amount of UNCERTAINTY: Do we have product / market fit? Where will our growth come from? Will we get enough funding to keep going?

3) A great founder will challenge you constantly. Our CEO always asks the one question that no one anticipated. It stretches me to think “what am I missing?” It stretches me more to accept that sometimes I’ll miss a key idea, and that’s okay.

4) The leadership team’s values are INCREDIBLY important The less ego at the top, the more everyone wins. Financially, personally and otherwise. A business wins by focusing on what the customer wants, not someone’s ego.

5) It sucks to miss goals and let people down VC-backed startups are ambitious and require growth multiples. Sometimes external variables (ex: COVID) get in the way. The best you can do is rally your team behind the mission and figure it out.

6) What you do in year 1 is very different from year 2, year 3, year 4, etc… If your company is growing, you are getting promoted and taking on new responsibilities. Just when you figure it out, it’s not your job anymore.
7) Be biased to act Small experiments can reveal big insights quickly. Don’t waste time over-planning / overthinking. Run lots of small experiments and expect that some will work out.
8) MVP most things. There’s often a fast way that does 80% of the right thing and tells you what you need to know. It’s common to not know what you actually need until you start building or using something. Don’t try to make it perfect at first.
9) Take risks If you do what everyone else does, you’ll get the same results as everyone else. Try things that no one else is doing.10) Nothing is “not my job”. If it will move us to where we want to go, do it yourself or find the person who will.
11) Show people it’s okay to be wrong Moving quickly means you’ll inevitably make mistakes. Companies where people are afraid to be wrong end up with “reality debt” and bad culture.
12) Let curiosity carry you. Startups are great places for curious people because most days bring novel challenges. Always seek out new skills or info that will help you get better.
13) Understanding technical things is very useful. Learning how websites and code work makes you a better collaborator with product / tech teams.
14) There’s only so much that scrappy people can figure out quickly… If you reach a certain size, eventually they may bring in more experienced folks with deeper backgrounds. This can be a great learning opportunity.
15) Identify your weaknesses Smart people can still have big blind spots. Get feedback on what you may be missing.
16) Be flexible. Rigid people don’t work well in startups. The mission may stay the same but the direction of execution may change often. If that bothers you, you’ll be unhappy.
17) Finding good people is hard. Some recruiters are high volume low quality, some are high quality low volume. Find the approach that works for you.
18) Manage to outcomes. Smart people like to figure things out on their own. Let them. If they need help, offer suggestions.19) Know your metrics. Whatever you’re doing, only a few numbers matter. Know what they are and how you impact them.
20) Focus on leverage. There’s always too much to do, especially early on. Find the outcomes that will 10x your team’s impact. This can be hiring, adding tech, improving analytics, basic automation, etc.
21) If no one owns it, it won’t get done 100% If something is important, a single person should be responsible for it.
22) Be anti-bureaucratic Make it easy to execute independently for as long as possible. Nothing frustrates a doer more than “process”.
Courtesy @bbourque via twitter