Published Jan 18, 2021

20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure

Etsy CEO Josh Silverman reveals two key traits of great leadership, explains why happiness shouldn't be tied to milestones, and outlines strategies for team structuring to enhance experimentation and agility. He also delves into his vision for Etsy as a creative alternative to Amazon and discusses the balance between learning from success and failure.

Episode Highlights

Topics covered

Successful Experimentation
01
Visionary Business Strategy
02
Leadership Traits
03

Questions from this episode

What is success?
Asked by 38 people
What makes a company mission-driven?
Asked by 31 people
What are your core values and principles when it comes to doing business?
Asked by 26 people
Is failure a valuable data point?
Asked by 17 people
How can I maintain team accountability?
Asked by 16 people

20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure

Topics covered

Popular Clips

Happiness and Success

Challenging Dogma

Learning from Failure

Accountability and Milestones

From Policy to CEO

Embracing Discomfort

Challenging Core Beliefs

Long-Term Planning

Embracing Uncertainty

Streamline Spend

Saving Time and Money

Global Employment Solutions

Vital Few vs Worthwhile Many

Etsy's CEO Insights

Embracing Crisis

Questions from this episode

What is success?

What makes a company mission-driven?

What are your core values and principles when it comes to doing business?

Is failure a valuable data point?

How can I maintain team accountability?

Episode Highlights

Successful Experimentation

Visionary Business Strategy

Leadership Traits

20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure

Topics covered

Popular Clips

Questions from this episode

Episode Highlights

Successful ExperimentationJosh Silverman, CEO of Etsy, shares insights into fostering a culture of experimentation and effective decision-making. He discusses how Etsy's agile framework supports innovation and how he navigates risk and opportunity in leadership roles.

Successful Experimentation

Visionary Business StrategyJosh Silverman shares his vision for Etsy as a human-centric alternative to Amazon, emphasizing the importance of creativity and personal connection. He also discusses the value of adaptable planning and focusing on impactful initiatives to drive growth.

Visionary Business Strategy

Leadership TraitsJosh Silverman, CEO of Etsy, discusses his strategies for turning crises into opportunities and his personal evolution as a leader. He shares insights on challenging core beliefs, embracing uncertainty, and focusing on short-term milestones for growth.

Leadership Traits