Changes Brought by Raising Money

When considering whether to raise venture capital, entrepreneurs go through the pros and cons. Growth capital, potential insight and connections, weighed against more rapid timetable, potential meddling or pressure, etc.

These are big, important considerations. There are also some more personal considerations a founder should think through. What’s your style? What’s your personal pace? Do you like keeping people in the loop and getting feedback, or do you hate it and want to be left alone? Do you value bigger swings with bigger upside, or more flexible meandering grind?

It’s also worth thinking about how investors change your mental game. No matter how much you know they don’t need or expect every company in their portfolio to win big, you will feel the need to win big for them. You will feel a pull to define the what and how of success on your idea of their expectations. No matter how much you may think pleasing investors won’t weigh in, it will. It’ll be in the back of your mind. Not a big deal, but one more thing to juggle in a complicated stew of expectation management.

If that sounds torturous, you may not be a great fit for VC.

I never thought I was. And for half a decade, I wasn’t. But at some point, after clarifying a vision of something that I could see going 10x bigger and faster with VC (even though taking on VC makes margin for error 10x smaller), and finding a truly amazing VC match, I made the leap. I like it. Jury’s still out whether it ends up being better than the solo bootstrap approach, but I’m glad I jumped in. Complicating though it can be. It adds one more thing that can subtly distract from the customer, but it’s brought a lot of excellent stuff too – mostly pushing me to think bigger, faster, and clearer.