Jack Dorsey's Startup School talk in 2013 offered a refreshingly personal and unconventional approach to startup advice. Instead of a typical lecture on business strategy, Dorsey shared insights gleaned from two influential books: "The Art Spirit" by Robert Henri and "The Score Takes Care of Itself" by Bill Walsh, coupled with a personal practice of "Do" and "Don't" lists.
Dorsey highlighted key passages from "The Art Spirit," emphasizing the inherent creativity in every individual and the importance of doing things that resonate with one's self. He stressed that art is not merely an "outside extra thing" but is the act of finding the gain within the work itself. Dorsey drew parallels between the art student's journey and the entrepreneur's, both requiring courage, stamina, and the willingness to be alone in many ways to discover their unique voice. He cautions against blindly following established conventions in the tech world, urging listeners to create their own language and path. He reinforced that one needs to be a master of their tools. Finally, Dorsey highlighted the book's sentiment that we are building what we want to see in the world, rather than responding to external demands.
Transitioning to Bill Walsh's "The Score Takes Care of Itself," Dorsey delved into the crucial aspect of leadership and team building. He emphasized the importance of establishing a clear standard of performance, beginning with a structural format, a basic philosophy, and then gathering the right team. Walsh's book provided practical lists of "Do's" and "Don'ts" for leaders, emphasizing the need to be committed to excellence, positive, prepared, detail-oriented, and accountable. It also touched on being flexible while maintaining firmness. Dorsey further quoted General Patton's list of best practices for leading an army which included giving praise over blame, informing troops on actions, having discipline built on pride and detail, and officers setting an example. He addressed the “success disease” which Walsh spoke about to protect against complacency, so he added a list for that. These are to formally celebrate and recognize ownership, to be apprehensive about the applause, to use time to make hard decisions and address specific situations, and to always remember mastery is a process and not a destination. He cautioned against pitfalls like excessive delegating, favoritism, and creating an overly comfortable environment devoid of tension and urgency.
Dorsey then shared a personal tool he uses daily, a simple "Do" and "Don't" list in his phone's notepad. He encouraged the audience to create their own list, checking it every morning, throughout the day, and before bed. The "Do" list comprises daily aspirations, while the "Don't" list contains actions to avoid, reflecting past mistakes or undesirable behaviors. Dorsey shared examples from his own list, including staying present, being vulnerable, maintaining a healthy lifestyle, and physical fitness. He emphasized that the "Do" and "Don't" list provides focus and allows one to ignore external noise, focusing on what is most important. This concept extends to his companies, where "Do" and "Don't" lists guide strategic decisions, enabling innovation and bold bets.
Dorsey concluded his talk by sharing one of his favorite songs, showcasing that building a team is a way to construct something that delights people, an end product from the work. He urged the audience to build something that resonates with every single person on the planet. He also touched on how simplicity in creation can be extremely complex. He reiterated that attendees were the future with the unique ideas to build for themselves, which would resonate with others.