At TableCheck (Japan's answer to Resy, Tock, Sevenrooms, etc.) our first 100 customers were definitely the hardest. It took us nearly two years, and many times I came close to giving up. Even though we had built a solid MVP, in Japan's risk-averse culture, no restaurant wanted to be the first to use our product. The question was always "Who else is using it?"--basically a deadlock.
After a lot of cold-calling, we found a 120-year old sukiyaki and shabu-shabu restaurant chain. They told us they always survived by adopting the latest technology, and were willing to try our product. Most of their staff were elderly women in kimonos, many of whom had not touched an iPad before. We were worried they would struggle, but after a few training sessions they got the hang of it--soon they were greeting and seating customers with no problem.
12 years on, we are at 13,000 restaurants on our platform and adding a few hundred more each month!
replies(1):