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Insight
Silverman: Business moves faster and impacts communities better than policy work
“I think when you run a business, you're able to really move much more quickly than in policy, and I think do a lot of things that can positively impact community.”
Josh Silverman Jan 18, 2021 ▶ 3:56 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
Insight
Silverman: 20-year career plans are overwhelming and likely to get derailed
“I think this notion that you've got to figure out what you're going to do for the next 20 years can be so overwhelming. And life has so much luck and Fate involved that if you hang everything on some twenty-year aspiration, the probability that something is go…”
Josh Silverman Jan 18, 2021 ▶ 5:44 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
Insight
Silverman: Successful companies confuse what helped them with what hindered them
“The other thing I've observed in companies that have achieved some level of success is they confuse that they've succeeded because of and the things they've succeeded in spite of.”
Josh Silverman Jan 18, 2021 ▶ 12:19 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
Insight
Silverman: Untouchable corporate dogmas yield the highest-value experiments
“So in some ways, the things that people are unwilling to test or experiment with are often the things that are most valuable to test and experiment with.”
Josh Silverman Jan 18, 2021 ▶ 16:06 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
Insight
Silverman: Being different only matters if it makes you better
“I want to be better than everyone else, and so if you can't tell me why different makes us better, I'm not that interested.”
Josh Silverman Jan 18, 2021 ▶ 16:53 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
Insight
Silverman: Teams failing with bold, customer-focused ideas deserve high esteem
“There are teams that have delivered close to zero over the course of the year, and I hold them in great esteem because their ideas are bold and grounded in good customer insight.”
Josh Silverman Jan 18, 2021 ▶ 27:48 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
Insight
Silverman: CEOs must build baseline competence in weak areas for empathy
“I think there's table stakes and there's your spikes or strengths, right? So whatever your job is, there's table stakes good enough. I'm not a project manager by nature. It's not What I'm great at. But to be an effective CEO, there's a table stakes level of pr…”
Josh Silverman Jan 18, 2021 ▶ 35:54 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
Insight
Silverman: True happiness comes from hindsight fulfillment, not present ease
“Happiness, you normally, I don't know, in my experience, I don't often have happiness in the moment. I have happiness in hindsight. When I feel like we have achieved something of great purpose, at the end of my life, I will reflect back and determine that I wa…”
Josh Silverman Jan 18, 2021 ▶ 13:43 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
Insight
Silverman: Pursuing every good ROI idea leads to corporate failure
“If you do all of the ideas that meet that criteria, you're dead in the water. There's far too many of them. So instead of asking what good ideas do we have, I try to ask, and I think we at Etsy try to ask ourselves, what are the fewest things we need to do in …”
Josh Silverman Jan 18, 2021 ▶ 19:35 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
Insight
Silverman: Etsy focuses on seller GMV above company revenue
“For me, the metric of success winning is all about GMV. GMV is the sum sales of our sellers. How much did our sellers sell this year? That's different than our revenue. Our revenue is a subset of that, and our profit is a subset of our revenue. But our seller …”
Josh Silverman Jan 18, 2021 ▶ 20:08 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
Insight
Silverman: Leadership requires only defining success, constraints, and hiring correctly
“Leadership is about defining success and defining constraints. And the more I've been on my journey, the more I realize it's those two things plus one. I would add one thing, which is making sure you have the right people on the team. But if a leader does only…”
Josh Silverman Jan 18, 2021 ▶ 21:15 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
Insight
Silverman: Framework for evaluating decision importance vs rollback cost
“The second decision matrix that I use a lot actually is a two by two framework of the importance of the decision and the cost of rollback. And if you think about each decision you make in terms of how important is it and what's the cost of rollback for There's…”
Josh Silverman Jan 18, 2021 ▶ 32:45 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
Insight
Silverman: Authentically echoing dissenting views builds trust during hard choices
“And for any difficult decision you make, there's going to be a group of people who don't agree with you. But if they know that their point of view was heard, and if they can actually hear you articulate it back, Here are the four things about this decision tha…”
Josh Silverman Jan 18, 2021 ▶ 30:04 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
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