In order to grow our company and expand, our skincare line S.W. Basics recently decided it was time to pursue a round of financing. This is sort of like taking on a whole new job. We had to fine tune our business plan, put together a deck (a fancier version of a business plan with pictures), carefully calculate our projections and then put it all out into the world. While demanding, the most intense part was the conversations I was required to have in order to convince investors that we were worthy of their money.

Imagine having to field questions like: What makes your company so special? How do you know you'll succeed? What are your limitations? Why you?


That last one can especially get you. No amount of paperwork can help you in this moment. Most of us entrepreneurs already have pretty inflated egos, we have no problem boasting to strangers about this "awesome idea we have that's going to change the world." But when the future of your company is on the line -- in the form of lots and lots of money -- it is an absolutely terrifying thing to do.

On one call, I presented a potential investor with every problem I thought the company might end up facing. Sounds silly, right? But I thought he should know. I imagined I was warning him so he could be prepared and expectations wouldn't be too high. I thought I was presenting myself as realistic and perceptive. Only later did it occur to me I was telling him exactly why we didn't deserve an investment, rather than why we did.

Related: How Much Confidence Is Too Much?

I learned a lot from that one conversation that I plan on applying in future ones with investors. Here are some of my takeaways:

  • If I don't believe that I can do it, how can I expect anyone else to? It's not just about your idea, it's about you -- who you are and what you bring to the table. Talk about that.
  • In the end, you will always have doubts, but unless someone asks you what they are, then you don't need to tell them.
  • It's not egotistical to figure out what your strengths are. You'll be more prepared and more convincing. If you are having trouble building up your confidence, do what I did: Practice on your friends.
  • Don't take the crazy insecurity train to crazy insecurity town. One little stumble does not make you bad at pitching investors. Eventually, you'll rock at it.
  • If all else fails, go back to the idea. You believe in it, right?

What other tips do you have for building up your confidence? Let us know in the comments below.