Most entrepreneurs are optimistic, says Mycoskie.

Question: What mistakes have you made in starting your business?

Blake Mycoskie: I’ve definitely made a lot of mistakes.

I’m very optimistic, and I think most entrepreneurs are. So if I come up with an idea of, like, oh, this would be a great place for us to sell TOMS [shoes] or great opportunity for us to really revolutionize this concept in the business, I tend to not see why it won’t work. I only see why it will work. And that does get in the way sometimes as a businessperson.

A perfect example is, when we started selling TOMS [shoes], we sold them in these really cool canvas bags. Everyone thought they were beautiful. They were simplistic. They were good for the environment, because we didn’t have the cardboard and the packaging. And everyone loved them. And when we first started selling TOMS, we were only selling in little boutiques. So, fine, they could manage 20, 50 canvas bags of TOMS very easily in a basket by the checkout.

Then we started selling in Nordstrom. And we thought, oh, this is great, we’re selling in Nordstrom, we’ll continue with the canvas bags. But Nordstrom is built upon very specific methods and protocol. And they have stockrooms. And in their stockrooms, they stack these boxes and they are very organized. And it allows their employees to go in and out and sell lots of shoes in a hour period of time. Well, what happened with the bags is even though everyone loved it, including Nordstrom, we didn’t really listen to the advice of the stockroom people who said we really should use boxes because this is going to be a tangled mess with these bags and these strings.

Sure enough, we launched Nordstrom to great excitement in the consumer side and great excitement on the salespeople. But two weeks after we’re there, all our bags were a big pile of mess in the stockroom. And they couldn’t sell any shoes because they didn’t want to waste half an hour going and untangling the shoes when they could’ve gotten commissions on three other pairs of Cole Haans.

So our business really took a hit this last year, and we had to transform everything from bags to boxes, which was a big, big change for us. And it cost us a lot of money and a lot of time. But now we are in boxes, and we’re seeing great sell-through in Nordstrom again. So it’s a perfect example.

Recorded on: April 28, 2008