The Ledger

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why aren't all 26 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Opinion
Silverman: Etsy is best positioned to be the alternative to Amazon
“I can't think of any company better positioned to be the alternative to Amazon than Etsy.”
Josh Silverman Jan 18, 2021 ▶ 10:51 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
Assertion Supported
Silverman: Etsy cut 20% of staff, half of projects in five weeks
“We had to lay off over 200 people, you know, within five weeks of joining the company, we'd laid off 20% of the staff, and of the remaining staff, probably 80% of them had new jobs, and we'd shut down over half of all the projects that the company was working …”
Josh Silverman Jan 18, 2021 ▶ 28:57 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
Assertion Supported
Silverman: Etsy refused cloud software due to internal handmade dogma
“Etsy believed that because Etsy was about handmade, Etsy should make everything itself. So Etsy didn't use the cloud and built almost all of its software itself. And that was sort of lore. It was considered strategy, but I don't think it was strategy. It was j…”
Josh Silverman Jan 18, 2021 ▶ 12:50 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
Disclosure
Index Ventures sold Etsy too early before Josh Silverman's turnaround
“Another one where we sold too early was definitely Etsy. We didn't take into consideration the fact that Josh Silverman was going to come in and totally transform the organization, and that obviously we left a lot of money on the table.”
Danny Rimer Jun 17, 2024 ▶ 43:00 Danny Rimer: The Biggest Lessons from Missing Snap, Airbnb, Spotify and Facebook | E1166 · 20VC with Harry Stebbings
Disclosure
Plantenga: Etsy buying Depop caused existential panic at Vinted
“So Depop got sold to Etsy. And we were shitting our pants. Like I thought Josh Silverman is gonna like take a bit baseball bat and smash us into the ground because Etsy is a company I very much look up to. They're a great company. Josh is a great CEO. And I th…”
Thomas Plantenga Feb 12, 2024 ▶ 27:55 Thomas Plantenga & Alex Taussig: Vinted CEO's Ultimate Guide to Scaling Marketplaces | E1114 · 20VC with Harry Stebbings
Disclosure
First Round passed on Etsy due to Fralic's misplaced eBay confidence
“We had the opportunity to look at Etsy, and I was almost dismissive, or I just thought of it as this little niche of handmade goods or something, and I think I was jaded. I mean, I thought I knew so much from eBay that it kind of turned me off to the whole cat…”
Chris Fralic Apr 29, 2021 ▶ 16:30 20VC: The Roblox Memo: First Round's Chris Fralic on The 17 Year Journey to Build a $41BN Market Cap Company, Why It Is Way Harder To Increase Ownership Across Rounds Today & What Happens Post SPACMania
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
Opinion
Silverman: Executives ignoring personal weaknesses is flippant given employee livelihoods
“Yes. And especially if you're a leader, I mean, I don't know, I feel like if, I mean, all of us are leaders in our own roles, but if you have the privilege to lead a whole company, there's a lot of people whose livelihoods are at stake. You know, it feels trem…”
Josh Silverman Jan 18, 2021 ▶ 36:59 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
Assertion Partly supported
Danny Rimer: Etsy Scaled From 250k to Over 3M Merchants, Defying Critics
“I'll never forget investing in Etsy and folks saying, well, it's crazy. You know, they already have 250,000 merchants online, all these arts and craft stores. Like, how many more can there be? And I think we're three million plus at this point in counting.”
Danny Rimer Dec 3, 2018 ▶ 12:13 20VC: Index's Danny Rimer on His Biggest Lessons On Price, Ownership, Board Dynamics & Building Consumer Businesses from Backing The Likes of King, Skype, Farfetch, Glossier and more...
Assertion Partly supported
USV's 2004 Fund Had Four Investments Each Return the Full Fund
“We made investments in Zynga, Twitter, Indeed, and Etsy within about a six month period. In our 2004 fund, each of those returned the fund.”
Brad Burnham Jul 13, 2016 ▶ 17:46 20VC: USV's Brad Burnham on Co-Founding USV with Fred Wilson, What They Look For In Potential Partners & Whether We Are Entering a Period of Consolidation or Expansion
Assertion Partly supported
Rhodes: Etsy and Bonagora failed at wholesale by ignoring retailer demand
“Moving that online, people had tried it. Like Etsy tried this. There was this other website called Bonagora a while back that tried it. Everyone who tried it Would get a bunch of brands signed up, but then they couldn't get the retailers to order.”
Max Rhodes Feb 18, 2022 ▶ 7:22 20VC: Faire's Max Rhodes on Three Steps To Hire the Best Candidates, Why Every Company Should Have a Strategy Doc and How To Do It & The Art of Referencing; How to Get the Most Out of Every Reference
Opinion
Silverman: Etsy's market is massive, defined by 'special' rather than 'handmade'
“I don't think it's niche at all. I think it's massive. I just don't define the market as handmade. I define the market as special.”
Josh Silverman Jan 18, 2021 ▶ 10:56 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: 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: 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: 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
Disclosure
USV Created Venture Partner Role for Albert Wenger for Sourcing Etsy
“Been very actively involved in Etsy early on and brought Etsy to the partnership. And we created a venture partner role for Albert to, you know, to sort of compensate him for having brought Etsy to the partnership.”
Brad Burnham Jul 13, 2016 ▶ 7:17 20VC: USV's Brad Burnham on Co-Founding USV with Fred Wilson, What They Look For In Potential Partners & Whether We Are Entering a Period of Consolidation or Expansion
Disclosure
Wenger angel invested in Tumblr and Etsy before bringing them to USV
“Started making some angel investments, some of which became USV investments, and some of which were USV investments, so it's an angel in Tumblr, and it's an angel in Etsy, and I brought that deal to Union Square Ventures”
Albert Wenger Jul 11, 2016 ▶ 4:31 20VC: USV's Albert Wenger on Automation Replacing Humans, The Universal Basic Income and The Instalment & The Deployment Phase
Opinion
Galston rates Etsy stock between a sell and hold at $1.6B
“So I actually just looked it up. It's basically at 1.6 billion, which is where it kind of went out. I'd say somewhere between a sell and a hold.”
Ezra Galston Aug 17, 2015 ▶ 22:53 20 VC 063: What It Takes To Standout In A Crowded Market with Ezra Galston @ Chicago Ventures
Assertion Supported
Lipman: Two-year-old Slack valued at $2.8B compared to Etsy's $3.5B IPO
“And when you look at, like, the recent IPO this week of Etsy you know, they're a ten-year-old company, and Slack, You know, is a, you know, two-year-old company, and they, Slack is valued at a two-point-eight billion dollar valuation, where Etsy is, you know, …”
Brandon Lipman Apr 20, 2015 ▶ 14:35 20 VC 029: The Potential Upside To A Technology Bubble with TechCrunch's Brandon Lipman
Assertion Supported
Silverman: Four million sellers rely on Etsy daily for their livelihoods
“Four million sellers count on Etsy every day to feed their families and to connect with community.”
Josh Silverman Jan 18, 2021 ▶ 9:07 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
Assertion Supported
Silverman: Etsy squads ship at least two to three experiments monthly
“Typically, a squad is going to ship two or three experiments a month at least.”
Josh Silverman Jan 18, 2021 ▶ 26:32 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
Assertion Supported
Silverman: Etsy uses 10-person squads focused on a single customer metric
“At Etsy, the way we do it is we're organized in squads. The unit of work at Etsy is a squad. A squad is about 10 people, six engineers, a designer, a product manager, an analyst, roughly. And they're given one customer problem to fix and one metric of success.”
Josh Silverman Jan 18, 2021 ▶ 25:47 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
Assertion Supported
New York City consistently produces billion-dollar tech exits like Etsy and Tumblr
“New York, we believe, has now shown that it consistently can produce billion plus dollar exits, and so that's companies like Etsy and Mongo and Tumblr and a bunch of others, you know, a bunch of e-commerce companies as well.”
Nicholas Chirls Sep 14, 2015 ▶ 7:19 20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital
Disclosure
Charlie O'Donnell was present for USV's Indeed investment and first Etsy meeting
“Although I was there when we invested in indeed and there for the first meeting when we met Rob Kalin and at Etsy.”
Charlie O'Donnell Jun 8, 2015 ▶ 14:55 20 VC 043: How To Be A VC Analyst and Lessons From Union Square and First Round with Charlie O'Donnell, Founder @ Brooklyn Bridge Venture
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