I am now well into my third startup. It has been a 15+ year journey throughout which I have made many mistakes, learned a lot, had a lot of luck, benefited from the help of many, and enjoyed (almost) every moment.
But there are things I know today that I wish I had known when I first started.
Constant existential threats
There are always between 3 and 5 things that feel like existential threats that will keep you up every single night. If there aren’t — you are not paranoid enough and you are not recognizing the dependencies you have. It is critical to know and identify the threats or you won’t be able to get in front of them to solve them before they do become existential.
You have to figure everything out
There are no rules in startups and almost zero structure to lean on. Startups are about doing something new and from scratch. So every startup ends up being completely unique. You can read books, talk to experts, rely on advisors, but at the end of the day no two situations are the same. You have to figure it out yourself and usually the best way to do so is to just try something, anything and be open to changing it quickly.
You have to be super careful about every dollar you spend, because even if $500 sounds insignificant in the scope of a $5M raise, there are hundreds of “insignificant” expenses that add up quickly. At the same time, not being aggressive enough is just as dangerous as spending too much money because moving too slowly is almost as sure-fire way for a venture to die in a competitive environment. Finding the right balance is almost impossible and you should be obsessed with constantly assessing your spend.
You can NEVER spend too much time building a great team. The team is everything. But it’s also the hardest thing to get right and means more than just recruiting and retention. It means investing heavily in transparency, context, and alignment so everyone can work well together. In my experience great performers want to work with other great performers, which means keeping the bar consistently high is critical, but also very painful and difficult.
BD / Channel Deals
Great BD opportunities are very rare, but when they work they are exceptionally powerful. I have probably signed 15–20 channel type deals over the course of my last few companies and 2 of them have worked and they became hugely strategic. The others went absolutely nowhere. They all required a ton of work and it was very hard to predict which ones would be great and which ones wouldn’t.
We all have blindspots. This is especially true of CEOs. Constantly be searching for what your blindspots are, as they are likely to be blindspots for the entire company and the first places you should hire up.
Good outcomes are rare, because they are generally the result of an acquiring company internally developing a hypothesis that they need to buy you or someone like you. This is very difficult to manufacture. That means luck & timing plays an outsized role. But it also means you need to be evangelizing your view of the future to help bigger companies internally build a hypothesis.
Outcomes tend to be binary; they are either amazing or zeros. I believe strongly that it is better to optimize for a positive outcome than for your slice of the pie.
These are a few of the things I wish I had known 15 years ago. My parting thought is that startups truly are a series of exceptional highs and lows. The hardest part about being an entrepreneur is not to get too down when things are rough and not to get too excited when things are good. At the end of the day it is a blessing to even be on the journey.