People Who Can Help You Are Tough Questioners

I never raised capital at CCAW, but I do remember having conversations with investors. They weren’t looking to invest, but they wanted to better understand the business. I vividly remember the nature of their questions. They asked about the most private, guarded details. Things no one else asked about (or knew to ask about). How much of the company do you own? How much cash do you have on hand? What was last month’s revenue? The questions always made me feel a bit uncomfortable. Not because I didn’t know the answers; I did. It just felt weird giving detailed information about my business to someone I’d just met and might never speak with again. It made me feel vulnerable.

In the end, I’m glad I was asked and answered these questions. My answers helped the investors benchmark my company against other companies they evaluated. They were able to point out the areas in which I was doing well—and the things that concerned them. The true value of their feedback was why they felt the way they did. They were able to explain what they’d seen with other companies (or their own companies if they were former founders). I was able to essentially learn from the experience of other founders (albeit through investors).

If you’re a founder looking to raise capital or get outside opinions about your business, get ready to feel slightly vulnerable and uncomfortable. If you’re talking with credible investors or former operators, they will ask tough questions. Rest assured that being forthcoming in answering them is likely to result in good things for you and your business. Get comfortable being uncomfortable—it means you’re learning!