334: Yancey Strickler - Using The Power Of Metaphors (This Could Be Our Future)

Episode Summary

Executive Summary: Ryan Hawk interviews Yancey Strickler about leadership, self-awareness, and his book This Could Be Our Future. Strickler argues that great leaders are selfless, curious, and open to feedback, and introduces Bentoism—a framework for making decisions based on now me, future me, now us, and future us. The conversation explores hiring, crisis leadership, metaphors, and building more generous, effective organizations.

Main Topics: Selflessness as the foundation of great leadership: Strickler says the best leaders sustain excellence by focusing less on themselves and more on others, combining strong vision with flexibility and empathy. Learning to lead through fear, pressure, and crisis: He describes how fear and pressure can be assets, noting that he is at his best in crisis because it creates clarity and forces him to dig to the real problem. Hiring and developing leaders through humility and honesty: He explains that he looked for selfless, honest leaders who could tell the truth, take responsibility, and serve the mission rather than their egos. Bentoism and expanding self-interest: Strickler details Bentoism as a framework that broadens rational decision-making beyond short-term personal gain to include future self, current community, and future generations. Metaphors, storytelling, and communication: He emphasizes combining unrelated ideas into vivid metaphors to make abstract ideas memorable and persuasive, and says this is a learnable leadership skill. Feedback, failure, and identity shifts at Kickstarter: Strickler recounts his difficult 360 review, emotional burnout, and eventual decision to step away from Kickstarter after realizing the organization needed something different. A more generous future through new values: The discussion closes with his belief that society needs new metrics beyond financial value, especially for climate, loyalty, and social cohesion.

Key Arguments: Great leaders sustain excellence by being selfless: they hold tightly to vision but remain flexible about everything else. Leadership requires understanding other people deeply; managers should regularly check the temperature of their teams and customers. The team usually knows whether a leader is working, even before the leader does; honest feedback must be taken seriously. Promoting or hiring top performers into leadership roles can fail if the job requires a different skill set than individual execution. Bentoism expands rational self-interest from just 'now me' to include future me, now us, and future us. The current dominant worldview overweights financial maximization and underweights long-term, shared, and generational consequences. Metaphors are powerful tools for leaders because they translate complex ideas into something people can feel and remember. Crisis can be clarifying and energizing; some leaders perform best when they have to solve urgent, high-stakes problems. The future of better decision-making depends on creating new values and metrics that can be measured and shared broadly. People should not simply follow the dominant concept of success; they should build a personal framework aligned with their values and responsibilities.

Data Points: Kickstarter team size when Strickler became CEO: 70 - He started as CEO with roughly 70 employees. Kickstarter team size when Strickler left: 155 - By the time he stepped down, the company had grown to about 155 people. CEO tenure: 2014 to late 2017 - He said he was CEO from 2014 until late 2017. Shares of people choosing the same leader in peer consultation: More than 40% - He suggested that if more than 40% of employees say they go to the same person for help, that person may be the right leader. Stakeholder board valuation comparison: 80% - He cited a claim that companies with stakeholder boards are worth about 80% as much as traditional for-profit counterparts. Fullness principle: 80% full - He referenced the Japanese idea Hara Hachibu, where meals should leave you 80% full. Adele scalping reduction: 2% scalped - He said Adele's ticketing approach led to only 2% of tickets being scalped. Bento quadrants: 4 - Bentoism is presented as a four-quadrant decision framework. Workshop size: 15 strangers - He described hosting a workshop at his house with 15 strangers. Workshop count: 4 workshops - He said the home workshop was the fourth one he had run. Estimated people who have built bentos: About 50 - He estimated that around 50 people had built their own bento framework through his workshops.

Pivotal Quotes: "I needed to make friends with my fear. I needed to befriend the pressure." — Yancey Strickler: Explaining how he reframed anxiety and crisis as useful forces in leadership. "The team itself might know... if more than 40% of people say this same person, it's like, maybe that should be your leader." — Yancey Strickler: On identifying leadership talent through peer trust rather than only top-down performance rankings. "The rational choice is not just now me... our rational self-interest is also our future me... now us... and future us." — Yancey Strickler: Defining Bentoism as an expanded model of self-interest and decision-making.

Implications: Listeners are urged to lead with self-awareness, seek honest feedback, and use broader decision frameworks that account for community and future generations. For organizations, the episode argues for more humane leadership, better hiring, and values beyond profit.