My first “real” investor pitch for digital.forest was in the lobby of the Seattle Westin hotel in the fall of 1999. There were five of us all huddled around a small coffee table to the side of the hustle and bustle.
My gut was doing somersaults and I was having a severe case of stage fright. I wasn’t sure I was going to be able to make it through this.
It was me, my friend Peter, who I had recruited to be a VP in the company, Michael, our advisor and lead investor who turned into a board member, and two prospective angel investors.
Michael had set up the meeting and had coached and worked with us to develop the pitch deck, which was a PowerPoint presentation that we had printed and handed out.
Taking a deep breath, Peter and I flipped through the presentation, stumbling and groping for purchase, trying to find the way to close an investment. We were sidetracked several times by flipping paper to answer questions. My stomach dropped even further.
Angel 1 was ebullient, loud, engaged, and asked many tough questions. Angel 2 was quiet, subdued, and seemed very distracted, like he wanted to be somewhere else. He didn’t ask many questions.
Angel 1 seemed very interested, but when we did the ask, he declined, saying he wasn’t sure we had our shit straight.
Deflated, and thinking we just crashed and burned, I turned to Angel 2 and timidly asked him. He chucked the presentation onto the table and then said, “Yeah, I’m in for a unit.”
My gut performed another somersault, but in a good way.