Founders start a business to have more freedom, and very quickly give up that freedom

Often founders start a business to have more freedom, or to be their own boss, and then very soon go out and give up that freedom and get a boss.

Usually when you start, you have all the control. You work hard to create a better situation for yourself than you had in your job, or previously. The dream is to feel free, to have a better lifestyle. It takes hard work upfront, but the opportunity is definitely there to fully shape how it will feel.

So many founders go out and take the well trodden path of raising funding, without thinking about the consequences. Usually after the first round, maybe even the second round, you still have control and can shape your company how you want. But it’s already starting to shift, you have pressure as soon as you have investors.

By the time you’ve taken a Series B, maybe even Series A, you usually have a board of investors, and you often don’t control the company anymore. You might not feel it at the time of finalizing the funding, as that is a moment of alignment and celebration, but in the details you’ve signed away the control you had. And what that means, is that technically you now have a job again. You work for those investors, and they can dictate what that means in a big way. You lose the ability to shape the culture and the lifestyle, and you lose the freedom that you often started out to have. And this can happen in the space of a few years, without you really realizing it.

Bryce Roberts put it really well in the crowd cast:

It’s strange to start your own business to become your own boss, and immediately going out to get a boss.