Josh Silverman

Guest: Josh Silverman, CEO of Etsy 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.  Links: Connect with Josh LinkedIn Connect with Joubin Twitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins This episode was edited by Eric Johnson from LightningPod.fm

Josh Silverman

CEO

Etsy

This Week in Startups is brought to you by… Coda. Coda empowers your startup by bringing words, tables, and teams together. Strategize, plan, and track goals effectively with all your valuable data in one place. Go to https://www.coda.io/twist to get started for FREE and get 6 free months of the Team plan. Intercom. Intercom’s AI-first service is the best thing to happen to your customers since you. TWIST listeners can get 90% off Intercom’s platform at https://www.intercom.com/twist Micro1. Micro1 is an AI recruitment engine to hire world class engineers fast. Visit https://www.micro1.ai/twist to open a talent search and get a 2 week free trial per hire. * Todays show: Etsy’s Josh Silverman joins Jason to discuss the marketplace business model (2:54), UX challenges (4:58), company operations during the pandemic (36:57), AI’s impact on team size (50:56), and more! * Timestamps: (0:00) Etsy’s Josh Silverman joins Jason (2:54) The marketplace business model and Etsy's growth (4:58) Maintaining Etsy's unique marketplace and UX challenges (10:34) Defining handmade and GenAI art on Etsy (11:53) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist (13:18) Preventing inauthentic sellers and the seller approval process (20:14) Etsy's star seller program and the importance of artisanal items (26:26) Intercom - TWIST listeners can get 90% off Intercom’s platform at https://www.intercom.com/twist (27:55) Durable products, warranties, and customer loyalty (35:47) Micro1 - Visit https://www.micro1.ai/twist to open a talent search and get a 2 week free trial per hire. (36:57) Company operations during the pandemic and efficiency era (44:11) Global talent, remote work, and productivity at Etsy (50:56) AI's impact on team size, productivity, and customer support (55:10) SEO strategies, organic traffic, and handling IP issues * Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/ Check out the TWIST500: twist500.com * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Follow Josh: X: https://x.com/jgsilverman LinkedIn: https://www.linkedin.com/in/joshuasilverman * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (11:53) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist (26:26) Intercom - TWIST listeners can get 90% off Intercom’s platform at https://www.intercom.com/twist (35:47) Micro1 - Visit https://www.micro1.ai/twist to open a talent search and get a 2 week free trial per hire. * Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com * Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Josh Silverman

CEO

Etsy

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 As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Josh Silverman

CEO

Etsy

When do you see the forest? And when do you see the trees? Building a company to scale requires a delicate balance of macro and micro focus – and the skill to know where to focus when. Josh Silverman has built that skill in leadership roles at Evite, eBay, Skype, and now Etsy. What he’s learned: Success isn’t just about zooming in on the details or taking the long view – but about knowing when to switch between perspectives. Read Nik Money's book The Selfish Ape: Human Nature and Our Path to Extinction. Watch Scott Suko topple dominoes: https://www.youtube.com/watch?v=-IuUp-rI0VU&feature=youtu.be Read a transcript of this interview at: https://mastersofscale.com/josh-silverman-when-to-zoom-in-when-to-zoom-out/ Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Josh Silverman

CEO

Etsy