In 2006, the idea of shelling out $1,000 for—well—anything made Jason Ross cringe. But the mild-mannered Ohio entrepreneur had a dream business to launch. In order to get his men's discount clothing site, JackThreads, off the ground, he knew he needed to make contacts with big fashion brands. So the now-30-year-old took a chance on a ticket to a popular New York City trade show. Here, Ross talks to's Nicole Carter.

Why was this $1,000 so crucial for your business?
At the time, my business idea was somewhat vague: I wanted to build a site where men could get discounted clothes. I had to start with brands. I needed to bring fashion brands on board—and not like a few, like a lot. As I was cold-calling these brands, they all kept asking me if I was going to this one trade show called Project in New York City. And the more people that kept saying that, it dawned on me that I should probably go. It cost $1,000. So I booked the trip. I made contacts with over 100 brands, so it was worth every penny.

How much start-up cash did you have at the time?
I had an SBA loan for $85,000 and a credit card. So $1,000 doesn't seem like a lot, but personally, I had no money at all. I was crashing on couches in New York to save money.

How did you approach these brands once you were there?
I was actually really nervous. I walked into the show feeling like such an outsider that I walked right back out. I was outside thinking, "What am I doing? I'm from Ohio; I don't know anyone in there." It seemed like such a mountain, especially for the big guys like Nike and Adidas. But I pumped myself up, and went back in. I went booth to booth and just started pitching. They were all really friendly, and surprisingly open to talking about my idea.

What did you learn from them?
They voiced some concerns about my business plan, and I used this opportunity to tweak my business model. I got a sense of the type of business they would want to work with.

What kinds of concerns did they have?
Everybody was very concerned about having their off price merchandise available for long periods of time online, polluting their sales pool. And this was in 2006, so flash sales sites were mostly in Europe. But that business model was perfect, so I decided to make JackThreads a private shopping club with daily deals. And the rest is history.

Do you still talk to these contacts you made?
Oh yeah. Actually, it took me over two years to launch JackThreads, so I went to a trade show every six months. I stayed in touch with the people that I met in the first round, updated them on my progress, and kept them in the loop for launch. The relationships I started there are what still make JackThreads successful today. We have almost a million members and over 450 brands working with us now.