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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

Jan 18, 2021

Josh Silverman, CEO of Etsy and former leader at Skype and eBay, shares insights on effective leadership and the unique challenges of e-commerce. He discusses the importance of embracing crises for growth and the relationship between happiness and success milestones. Josh highlights the significance of strategic decision-making and focuses on optimizing teams for experimentation and agility. He emphasizes that learning often comes more from failures than successes and reflects on the evolving landscape of leadership in today's entrepreneurial world.

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ANECDOTE

Unplanned Career Path

Josh Silverman's career path was unplanned, starting in public policy and transitioning to business.
He co-founded Evite and later focused on revitalizing companies like Skype and Etsy.

ADVICE

Short-Term Goals

Focus on 3-4 year goals instead of overwhelming 20-year plans. Life's unpredictable, so shorter sprints offer more control and adaptability.

ADVICE

Assess Risk and Opportunity

Consider upside and downside when evaluating opportunities, especially risky ones.
If the upside is meaningful and the downside is acceptable, take the chance.

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Josh Silverman is the CEO @ Etsy, leading the company as it builds a platform that empowers creative entrepreneurs around the world. Prior to their IPO, Etsy raised funding from some of the best in the business including Danny Rimer @ Index, Albert Wenger @ USV and Jim Breyer @ Accel to name a few. Prior to Etsy, Josh served as President of Consumer Products and Services at American Express, was the CEO of Skype, and CEO of shopping.com, and he held various executive roles at eBay. Josh is also currently on the board of directors of Shake Shack.

In Today’s Episode You Will Learn:

1.) How Josh made his entry into the world of startups, came to be CEO of Skype and how he came to be CEO of Etsy? How did Josh's political background prepare him for being a public markets CEO?

2.) How does Josh think about 10 year plans? What is the right alternative? What does Josh do when he does not know what to do? How does Josh think about head vs heart in decision-making? How does Josh think about downside protection and risk mitigation with decisions?

3.) Why does Josh believe that you should, "never let a crisis go to waste"? How does he interpret that? Does Josh believe you learn more from success than failure? Why does Josh believe many succeed in spite of, not because of? How does Josh connote happiness to a milestone of success? What is true happiness for Josh?

4.) How does Josh think about winning today? What is the framework Josh believes founders need to put in place to optimise their chance of winning? How does Josh structure his team at Etsy to optimise for speed and experimentation? What has worked? What has not worked?

5.) How can leaders create a system where failure is minimised? How does Josh implement a "red hat vs green hat" decision making process around new ideas at Etsy? What question does Josh and the team ask with every experiment? How should one analyse the cost of rolling back a decision?

6.) How does Josh determine between dogma and good practice in a company? What is the right way to remove antiquated dogma without damaging morale? What were some of the biggest challenges from his doing this on entry at Etsy?

Item’s Mentioned In Today’s Episode

Josh’s Favourite Book: Grant

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