In 'Team of Teams', General Stanley McChrystal and his co-authors share insights on how to lead organizations effectively in a complex and rapidly changing world. Drawing from McChrystal's experiences commanding the Joint Special Operations Task Force in Iraq, the book highlights the need to move from traditional hierarchical structures to a more decentralized 'team of teams' approach. This involves fostering common purpose, shared consciousness, empowered execution, and trust among team members. The book uses historical and contemporary examples, including military and business scenarios, to illustrate how this approach can enhance organizational adaptability and success.
This book is a monumental biography of Robert Moses, who was the single most powerful man in New York City and State during his time. It explores how Moses accumulated and wielded power, shaping the city through his public works projects, including highways, bridges, and parks. The book delves into Moses's early life, his idealistic beginnings, and his transformation into a powerful figure who dominated New York's politics without ever being elected. It also highlights the social and environmental impacts of his projects and his eventual fall from power. The biography is renowned for its detailed and nuanced portrayal of power dynamics in urban politics[2][4][5].
This book tells the story of Yvon Chouinard, who brought doing good and having grand adventures into the heart of his business life. It details his journey from his youth as the son of a French Canadian handyman to his ambitious climbing expeditions that inspired his innovative designs for climbing equipment. The book also explores how Chouinard built Patagonia into one of the most respected and environmentally responsible companies, emphasizing the importance of sustainability, personal growth, and unconventional business practices.
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Tim Holley is VP of Product at Etsy where he leads the Etsy buyer experience. With a tenure spanning more than a decade, Tim has seen the company through many transitions (both in culture, in leadership, and in growth), and his team’s product changes have had a significant impact on buyer retention, conversion, and global expansion. In this episode, we discuss:
• Lessons from navigating corporate culture shifts
• How Etsy capitalized on the explosive growth of e-commerce during the pandemic
• Marketplace learnings: when to focus on supply vs. demand, optimizing conversion, and more
• How Etsy solves the “graduation problem”
• Tips for hiring product managers
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Find the full transcript at: https://www.lennysnewsletter.com/p/inside-etsys-product-growth-and-marketplace
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Where to find Tim Holley:
• LinkedIn: https://www.linkedin.com/in/timholley/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter/X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Tim’s background
(04:23) Tim’s time away at SoulCycle and what led him back to Etsy
(06:34) Lessons from the 2017 culture shift at Etsy
(12:15) Etsy’s guiding principles
(13:32) How Etsy adapted to increased demand during the early days of mask mandates
(16:38) What Tim learned about managing stress with his team during the pandemic
(18:46) Lessons from building a thriving marketplace
(21:47) Prioritization at Etsy
(24:37) Supply constraint vs. demand constraint
(28:43) Conversion wins
(33:27) Experimentation at Etsy
(37:58) Acquisition and top-of-funnel tactics
(39:44) The seller referral program
(40:33) Etsy’s habit loop framework
(44:11) How they set themselves apart from other marketplaces
(51:23) Retaining sellers
(53:23) The defunct Etsy studio
(55:18) Running the product team
(57:20) Who the decision maker is
(1:01:20) What Tim looks for when hiring PMs
(1:03:03) A reflection exercise Tim does with his teams
(1:05:08) Lightning round
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Referenced:
• Etsy: https://www.etsy.com/
• SoulCycle: https://www.soul-cycle.com/
• Inside the Revolution at Etsy: https://www.nytimes.com/2017/11/25/business/etsy-josh-silverman.html
• Ronny Kohavi on Lenny’s Podcast: https://www.lennyspodcast.com/the-ultimate-guide-to-ab-testing-ronny-kohavi-airbnb-microsoft-amazon/
• How to Kickstart and Scale a Marketplace Business – Part 3: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace-911
• Team of Teams: New Rules of Engagement for a Complex World: https://www.amazon.com/Team-Teams-Rules-Engagement-Complex/dp/1591847486
• Let My People Go Surfing: The Education of a Reluctant Businessman: https://www.amazon.com/Let-People-Surfing-Education-Businessman-Including/dp/0143109677
• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394720245
• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone
• Nara Baby app: https://naraorganics.com/nara-baby-tracker
• Huckleberry app: https://huckleberrycare.com/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
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