Josh Silverman, CEO of Etsy, shares his transformational journey at the company, where he initially hesitated but accepted leadership during turbulent times. He discusses the importance of energy management and effective delegation, emphasizing a shift in leadership style towards thoughtful decision-making. Silverman also reflects on the emotional toll of layoffs and balances work-life dynamics. Additionally, he addresses the role of AI in the future of handmade artistry, debating innovation versus traditional craftsmanship. His insights reveal a deep commitment to Etsy's community.
Josh Silverman emphasizes the necessity of energy management in leadership to enhance productivity and decision-making efficiency.
The podcast discusses the importance of adapting business strategies and fostering innovation by reassessing past methodologies without defensiveness.
Insights into the evolving role of AI in creativity highlight the need to embrace new technologies as empowering tools for creators.
Deep dives
Shifting Business Strategies for Future Success
The speaker discusses a significant transformation in business strategies after several years of successful operations. They emphasize the importance of reassessing and adapting approaches, suggesting that previous methodologies may not be effective for future growth. This shift is accompanied by a willingness to view the business with fresh eyes, akin to starting anew without defensiveness about past practices. Embracing this mindset fosters innovation and opportunities for improvement, ultimately enhancing the trajectory of the organization.
The Importance of Energy Management
The speaker highlights the significance of energy management in effective leadership. They express a newfound intentionality in directing their energy toward productive outcomes rather than merely logging hours in meetings. Creating structured time for contemplation has proven beneficial, allowing for more thoughtful decision-making and leading to shorter, more effective meetings. This deliberate allocation of time not only enhances productivity but also fosters a more focused and engaged work environment.
Types of Meetings and Their Purpose
A clear distinction is made among different types of meetings that leaders typically conduct, namely decision-making, accountability, and career development meetings. The speaker illustrates how each meeting serves a specific purpose, with decision-making meetings focusing on critical business choices and accountability meetings emphasizing performance reviews. They also mention that providing context to these meetings is vital for team understanding and engagement. Setting expectations for these various meeting types cultivates a more efficient and responsible organizational culture.
Leadership Challenges and Accountability
The speaker reflects on their journey of leadership, acknowledging the challenges faced when assuming a new role. They recount the difficulty of navigating significant changes and layoffs that often accompany organizational restructuring. Despite initial resistance from team members, the process ultimately led to increased focus and accountability within the company. Recognizing the importance of transparent communication during these transitions allows leaders to maintain trust and unity among their teams.
Embracing Innovation through New Tools
The conversation includes insights into the evolving landscape of tools available for creators, particularly the integration of AI in artistic expression. The speaker draws parallels between the adoption of electronic music as a legitimate art form and the potential acceptance of AI-generated art within creative marketplaces. They advocate for recognizing new technologies as tools that empower creators, rather than as threats to traditional craftsmanship. This perspective encourages embracing innovation for the growth of both individuals and organizations in the dynamic marketplace.
When Josh Silverman joined the board of Etsy, he had one condition: “Don’t ask me to the be the CEO.” And technically, they didn’t ask. One day, he got a phone call informing him the board had elected him as the new CEO, just days before an earnings miss. He knew the odds were against him — layoffs would be necessary, and “I was going to have to be the villain” — but decided to say yes out of a sense of duty to Etsy’s users and workers. “If I can be helpful, I have a responsibility to do it,” Josh says.
Chapters:
(00:55) - Energy management
(02:42) - Meetings
(09:56) - Etsy’s strategy
(13:36) - Learning to delegate
(17:10) - Setting an example
(24:17) - Evite’s rise and fall
(27:46) - Self vs. company
(30:22) - Legacy
(34:21) - Control and agency
(37:44) - Joining Etsy’s board
(40:40) - Becoming CEO
(46:16) - Culture shock
(48:09) - “We need you, trust us”
(51:25) - eBay and Skype
(57:15) - Pushed out
(01:00:40) - Accountability and family
(01:03:53) - Time horizons
(01:05:55) - Gen AI-supported art
(01:08:29) - Who Etsy is hiring and what “grit” means to Josh
Mentioned in this episode: Ken Chenault and American Express, Nick Daniel, Rachana Kumar, Ticketmaster and IAC, Etsy Studios, Silverlake, Shopping.com, Google, Microsoft, and Austin City Limits.