Bootstrapping vs Raising Out of the Gate: The Six Questions to Ask Yourself

This post is by Charlie O’Donnell from This is going to be BIG

A lot of founders debate whether or not they should try to raise capital or get a product up and running—perhaps even get some customers. Well, I’m here to give you a definitive answer.

It depends.

Oh, come now. You knew that was coming. There’s really no one size fits all answer, but I can give you a set of questions that can help you clarify a few things.

#1 Can you focus on this for any reasonable period—I would say 3-6 months—without putting yourself in serious financial difficulty?

Before you think about anything else, be honest with yourself about your own economic reality. Do you have dependents? What does your overhead look like? How quickly do you think you could get another job if you can’t raise money or get going successfully after this period?

These are all important considerations in determining whether you need to raise money to start something up—because while I appreciate the side hustle, I think it’s incredibly difficult to try to juggle two jobs at once. It’s very hard to replicate the benefits of being able to focus on something full time when you’ve got other things going on. That’s not to mention what else you’re sacrificing when you try to do two jobs at once—like friends, family, health, etc.

So, that’s the first test—do you need money to give this a shot?

Ok, so now you’ve decided that perhaps you can go a little bit on your own—or you can’t and you need (Read more…)