What’s the Worst That Can Happen?

So, that’s the happy part of it. But building a business is really, really hard. And you took a risk as an entrepreneur. All entrepreneurs take risks. What would you say has been—and it doesn’t have to be Poshmark, in your career overall— what would you say has been one of your biggest fears? And how did you overcome that?

I think with entrepreneurs, like you said, they’re risky, but once they decide to start a business, it doesn’t feel risky. That’s the thing, is you actually believe that your idea is so awesome, but that doesn’t mean you are the first one to do it.
Before I started in Poshmark, which is based in California, in Silicon Valley, I lived in New York. I didn’t understand technology as much. I was much more in the fashion world. But I knew that the next thing I wanted to do was going to be tech-based because I saw the limitations of inventory businesses.
It just wasn’t what I was going for. I wanted to have a broad impact on people. I didn’t feel like I could have that impact if you had an inventory business. So, what I did is I had lived in New York for 15-something years. It was home for me. I picked up and left. I left an industry I understood. I left a city I understood. I left my home and my friends. I left my family. And I moved to Southern California. I didn’t understand the industry. There was a different culture that I had to learn.
And so, that was the part where that was really hard. Because you didn’t know yet where you were going to land. So, you just have to take a leap of faith. And how I… I think you asked how do you handle that risk? I don’t always do this, but when I catch myself in this fear-based state, I try to remind myself to do this, is really visualize and write down what’s the worst thing that can happen. What’s the worst thing? So, moving across the country. Leaving all of your friends. It sounds scary. It was scary. But I love it now. Worst case scenario. That’s it.
That doesn’t sound so bad, right? You just move back. Maybe you lose some money because of moving costs, but that’s it. So, I visualize that fear. And then if you’re like me, you’ll realize it’s actually just fear. It’s not fear based on fact.