From June 24 to 30, my colleague, Ryan, and I hit the road for 30 meetings (and 4 calls) split between NYC and LA. Rather than tediously go through the details of our trip, I figured I’d share a few takeaways / learnings from the week.
1. Have a Strategy - Before nearly every meeting, Ryan and I would discuss what we wanted to get out of each conversation and how we were going to get to that result. Maybe we’d ask a leading question, maybe we’d try to bring up a new feature that our team had recently built, or perhaps we’d even mention another party with whom we were meeting or had met. Regardless, we always tried to have clear objectives for each appointment, and that helped us keep the discussion focused and most valuable for both sides.
2. Never Get Too Down or Too High - On an occasion or two, we didn’t think the meeting matched the lofty expectations we had set for ourselves. Rather than allowing this to carry over to the next one, we quickly analyzed what happened, critiqued ourselves, and made sure to keep our confidence high for the next meeting which was usually set to start 30 minutes after the previous one ended. Fortunately, we were rather pleased with how the majority of our meetings went. However, we were sure to enjoy the moment only briefly (while we waited for a cab in NYC or while we walked to our rental car in LA) before we refocused and began strategizing for the next meeting.
3. Divide and Conquer - During our trip, this phrase took on two different meanings. First, on a couple occasions, Ryan and I split up to handle multiple meetings during the same time slot. We had a fairly aggressive schedule, and splitting up allowed us to cover twice the ground when necessary (although this was only really possible in NYC). The second meaning is in regards to the meetings themselves. There are some questions that Ryan answers better than I and vice versa. Prior to our trip, we had a meeting in SF that served as a good test run for our marathon week. This meeting along with our own strategizing allowed us to figure out who would handle certain questions in meetings.
4. Act Like You’ve Been There Before - On several occasions during the week, we had meetings with high-level people in buildings with nicknames, such as The Death Star. Each time, we made sure to not get overwhelmed by the titles or experience of the people with whom we were talking or by the setting of the meeting. It is certainly easier said than done, but keeping our composure and acting like we’d been there before definitely made a difference when it came to establishing Gumroad as an integral cog to the future of their digital business.