The summer of 2011 was one of the most surreal times of my life as an entrepreneur. My company, DealsGoRound, a secondary market for daily deals, was receiving routine press coverage in the tech and business journals and I was about to embark on my first fund raising trip to San Francisco. We already received $350K in seed funding from Lightbank, my former employer and Groupon’s initial investors, and they made sure my trip out west was flocked with meetings and calls with top-tier and boutique venture capitalists which they viewed as value-add to our business. For three days, I bounced around Sand Hill Road in Menlo Park and downtown San Francisco meeting with VCs, tech reporters and just about anyone who would listen. The conversations always seemed positive and I felt pretty damn good about where things were going.
After returning home to Chicago, the initial investor conversations continued with follow-up calls, scheduling additional meetings in San Francisco and I continued to take inbound calls from new firms, as well. At any given time, I was juggling at least 15 of what I believed to be legitimate conversations regarding our next round of funding. In my mind we appeared to be in a great place. I clearly realized that DealsGoRound wasn’t going to be the next Twitter, but we were the first company to attack a niche market opportunity which one media outlet pegged as a potential billion dollar opportunity and we had already secured funding from one of the most influential players in the space.