Congratulations, you raised Series A! Here are the ten things you are going to screw up:
1/ You are extremely hard on yourself and that often translates into being hard on those around you. Your expectations are very high, often obsessively high around product and execution. That usually has a very positive effect in reaching Product Market Fit (PMF).
If you do achieve PMF and raise Series A, your team grows, people don’t know you as well, and that high criticality factor can scare and demoralize others. Tip: Be conscious of this and try to practice the magic ratio of five positive to every negative comment with others.
2/ You are certain that there is a bigger opportunity than what you currently have and want to keep experimenting to find it. Experimentation is necessary for finding the best PMF. The more you try, and the more obsessively, the more likely you are to find the best possible PMF.
Post-PMF, it drives your team nuts. It comes off as inconsistent, and causes changes and re-prioritizations all of the time. Tip:This one takes discipline. Use your creativity for good in the existing business by prioritizing the experiments you think could be game changers.
3/ Ideas and execution may be more important to you than people. Pre-PMF when your team is small, this is totally fine. There’s a lot to get done and you are an individual contributor, working alongside your co-founders and early team to get things done.
Post-PMF, your employees will quickly detect that they annoy you. This is the main area that keeps founders from being effective leaders and it is hard to change. Leading, even if you are always a bit harder edged, is what gives you the leverage to create an epic company.
Commit yourself to understanding people, not just being a problem solver. Tip: The main way I did that was to find the most influential people in the company. They may be managers, ICs, whatever. Learn from them and enlist them to help you level up.
4/ The confidence you had which allowed you to start a company can turn to arrogance over time. Pre-PMF, starting a company and being told no 90% of the time requires a lot of self-confidence. People without it quit.
Post-PMF, when your idea has been proven correct, it’s easy for that confidence to change into arrogance. Arrogance is a very dangerous thing. Arrogance is a story that you tell yourself that you know the right answer, no matter what the facts are.
Arrogance filters out arguments you don’t like from your consciousness. Tip: The way you learn changes post-PMF. Now you learn through your team. They are also the best informed to call BS on your dumb ideas. Listen to them.
5/ Resist creating a cult. Many many high-growth startups evolve into a system where the founder is worshipped in one way or another. While the ego gratification is nice, this completely eliminates a team effort when it comes to trying new things, executing and adapting.
No matter how smart you are, you cannot be the one brain trying to outsmart the rest of the competition. Tip: Actively kill the type of hero worship that evolves naturally. Be intentional. Seek out hero worship and squash it.
6 — You really aren’t great at getting things done, especially through layers of management. Because most founders were never managers or leaders before starting their companies, when it comes to executing on ideas in later stages, they often suck.
There is a tendency to want to keep doing things yourself as you did pre-PMF. Resist that. Tip: Surround yourself with people who are as good at execution as your are with ideas. Hopefully they respect new ideas and you respect execution enough to work together.
7/You are a control freak and letting go is hard for you. Obsessively controlling everything that matters is a very good way to find PMF, because getting things really right is difficult to delegate early on. Later on, it becomes a significant weakness for many founders.
Tip: It’s often true that in one specific task, someone can not do it as well as you, but if you keep your standards very high and figure out how to empower your team, the company can scale to solve all of the problems you encounter without you becoming a bottleneck.
8/Hiring people feels risky. Most founders have never hired big teams. They hire far too slowly and conservatively, insisting that only the best people are worthy of working at their company. Generally, this is not a bad bias, but if it keeps you from hiring it is bad.
10/You don’t give people enough equity. Being cheap on cash is good. Being cheap on equity is stupid. Worrying about dilution is fine, but apply that to investors not your team. Double equity the same way you double engineering estimates.
I hope you liked this thread! If you want more of this, follow me at @jwdanner and please retweet this so that more founders make fewer mistakes.