The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

Ben breaks up every period of his company into chapters, each with a beginning, goal, reflection period, and reward. For example, a few years after the business was founded—once Pinterest’s website had a loyal and rapidly growing base of users—the company embarked on a new chapter to “become a mobile service.” At the time, Pinterest was known mostly as a web destination, and Ben believed that the company needed to shift its mind-set to being mobile first. The next chapter at Pinterest was “to become a global service.” Once again, the entire company shifted to make it happen, focusing on certain regions, doing research to develop strategies for serving users in different countries, and making the site available in different languages. And then, a year or so later, the next chapter was “to become a cash-flow positive service,” which meant developing a scalable business model that also enriched the product experience. This chapter ushered in a new set of leaders, partnerships, and changed product priorities. What I like about Ben’s “chapters” approach is that each one applies to everyone in the company and embodies a goal rather than a tactic. Each chapter requires a fresh perspective on the product, renewed empathy with the product’s users, and a candid assessment of the team you have and the team you need. A chapter is a clear goal, underscored by why it is important, and then every team determines its tactics. As a chapter comes to an end, Ben believes teams must be reflec...