Chapter 3. Look for the Pain
Isaac is the founder and CEO of SendGrid, an e-mail service that solves the problems faced by companies sending application-generated transactional e-mail, which raised $5.75 million from Highway 12, SoftTech VC, and Foundry Group after completing TechStars in 2009.
I have always been interested in solving complicated problems and am naturally passionate about scalability and complex engineering problems. I enjoy using technologies such as Hadoop for massive data analysis, Memcached for distributed caching, and Twisted for event-driven programming. Early in my software engineering career I landed positions as CTO in multiple startups. The more I dealt with engineering problems, the less I wanted to be engaged with users or any other nontechnical problem. I strongly believed that my time was best spent on solving really difficult technical problems instead of dealing with all those pesky customers.
One day I was in the process of moving our static files to Amazon S3 to solve some scalability issues with our web site when one of those annoying users notified us that the e-mails that our application was generating were not getting through to his Yahoo! Mail inbox. Off I went to solve this seemingly trivial problem.
After a few tests I realized that Yahoo! was flagging all of our e-mails as spam. Since this was out of my control, I contacted Yahoo! ...