City Rewards Network

David Moore is the CEO of City Rewards Network, which combines deals from companies such as Coupons.com, Groupon, Living Social and Yelp. He previously managed a furniture store but decided he couldn’t take another day in retail. So he quit his job—with no savings, no severance and no safety net. Determined to go into business for himself, Moore, like many entrepreneurs, had to resort to some unusual funding methods, such as preselling the service to 60 customers at $1,000 a pop. “People look at you kind of crazy when you ask them for a check for $1,000 for something that doesn’t exist yet,” he said. Moore supplemented that with money from another source. “I applied for eight credit cards at the same time,” he said. “I gathered up every brochure I could find for Visa and MasterCard, and … called and applied [for all of them] in two hours,” he said. “I had to be quicker than the reporting system so the inquiries didn’t show on my credit report.” Moore was able to cobble together $25,000 that way, though “it pretty much tanked my credit score the instant the cards were issued and then maxed out,” he said. “It took a few years to recover from that.” It was worth it. He described the business today as “very, very profitable,” with 4,000-plus recurring customers. His methods were somewhat unorthodox, but Moore said it’s all in a day’s work for an entrepreneur. “Entrepreneurs do things most people won’t, so they can live like most people can’t,” Moore said. “Not sure who said that, but that’s how I roll.”

Securing funds is the first problem an entrepreneur encounters. It often requires courting a venture capital firm with the aim of wowing its members into opening the coffers.

Sadly, there can be only so many winners, and a number of entrepreneurs walk away empty-handed. This is when it’s time to be resourceful, to get creative and to engage in truly entrepreneurial thinking.

That can mean taking big risks and potentially courting disaster. But when it’s your only shot, it’s better than spending the rest of your life wondering, “What if?”