Jack Dorsey at Startup School 2013

Key Themes and Takeaways

• The Nature of Creativity and Art

  • Robert Henry's The Art Spirit defines art as "a province of every human being" rather than a specific profession limited to painters or sculptors.
  • True artists are described as "inventive, searching, daring, self-expressing creatures" who disturb, upset, enlighten, and open new pages of understanding.
  • The craft itself, not just the end product, must be the primary source of gain; the work must be done for its own intrinsic value.
  • Meaningful work often requires solitude, as "being alone" allows one to grow apart from the crowd and become acquainted with oneself.
  • Success in art and innovation comes from finding one's own path and tools rather than copying the conventions of "old masters" or successful predecessors.
  • Mastery is defined as a process of constant practice and being a "master of such as he has" at the current moment, not a final destination.
  • Rejection is an inherent part of the process; personal work is less likely to be immediately accepted by juries, but the goal is to paint for oneself, not for external validation.
  • Organizations must avoid stagnation by having a shared motive or purpose; without it, teams "wobble" and fail to achieve timeless results.

• Leadership and Organizational Standards (Bill Walsh)

  • Bill Walsh's approach, detailed in The Score Takes Care of Itself, emphasizes establishing a "standard of performance" based on specific actions, attitudes, and beliefs rather than just winning games.
  • High standards begin with identifying and revering specific actions (e.g., tucking in shirts, cleaning lockers) to signal a culture of care and excellence.
  • Leaders must communicate clear expectations for high effort, require the highest level of expertise, and teach their values and philosophy to ensure connection rather than independent contracting.
  • The "12 Habits of a Leader" include being yourself, committed to excellence, positive, prepared (viewing luck as preparation), detail-oriented, organized, accountable, near- and far-sighted, fair, firm, flexible, and believing in oneself.
  • Walsh advises leaders to "show and not tell" by leading from the front line, similar to General Patton's five rules for his army.
  • Effective leadership avoids specific pitfalls: paralyzing patience, excessive or insufficient delegation, favoritism, socializing excessively with subordinates/superiors, and creating a "comfortable" environment that lacks necessary tension and urgency.

• The "Success Disease" and Managing Growth

  • Winning organizations face a "success disease" where they risk relaxing, becoming overconfident, or changing for the sake of change rather than necessity.
  • To counter this, leaders should formally celebrate victories but limit applause to a short window to prevent complacency.
  • Post-success periods must be used to make "hard decisions" and address specific mistakes or areas that were not up to snuff.
  • Reaching the top does not make tasks easier; it makes them harder, requiring a continued focus on mastery as a process.
  • Leadership requires balancing a fun, relaxed atmosphere with appropriate levels of tension and urgency to drive performance.

• Personal and Organizational Execution Tools

  • The speaker utilizes a "Do and Don't" list checked daily via a digital note app to maintain focus and filter out noise.
  • The speaker's personal "Do" list includes staying present, showing vulnerability, drinking only lemon water and red wine, exercising (squats, push-ups, planks, running), meditating, maintaining good posture, greeting everyone, training with a heavy bag, and keeping a video journal.
  • The speaker's personal "Don't" list includes avoiding eye contact, being late, failing to meet set expectations, eating sugar/wheat/lentils/dairy (Paleo diet), and drinking hard liquor or beer on weekdays.
  • This methodology has been scaled at Square to create an organizational "Do and Don't" list, serving as "bold bets" to drive fast innovation, question assumptions, and reset organizational thinking.
  • The ultimate goal of building a team is to create a product that "delights people," creating a resonance that makes them tap their feet and engage deeply with the work.

• Forward-Looking Statements and Final Directives

  • The future of great art and technology will rely on fewer words and fewer copies, focusing instead on essays (or products) that are shorter in length but longer in meaning.
  • Creators are urged to build "what they want to see in the world," making a personal bet that others will resonate with that vision, accepting that wins and losses are inevitable.
  • The core message to the audience is that they are the future creators responsible for interpreting and building their own realities, free from external demands.
  • The speaker suggests that individual discipline in "Do/Don't" lists translates directly to organizational agility and the capacity to push boundaries.