20VC: The Story of Turning Around MTV, AOL and Time Warner | How To Be Effective When Making Hard Decisions | Tactics vs Strategy and Why Plans Are BS with Bob Pittman, CEO @ iHeartMedia
9th December 2022
James Reinhart is the Founder & CEO @ ThredUp, the world’s largest online thrift store, and consignment store. To date, ThredUp has raised over $130m in VC funding from many friends of the show including Tim @ Redpoint, Patricia @ Trinity, Eric @ Founder Collective and Ian @ Goldman Sachs just to name a few. As for James, prior to ThredUp he was a Goldsmith Fellow in Social Enterprise at HBS and a Bill George Fellow at the Center for Public Leadership at the Kennedy School. Before that, James co-founded Beacon Education Network, a charter management organization serving low-income students on California’s Central Coast.
In Today’s Episode You Will Learn:
1.) How James’ childhood dream of being an architect changed to founding the world’s largest online thrift store?
2.) Tim Hale @ Redpoint: “James is one of the most naturally talented leaders I have ever worked with”. So what does great leadership mean to James? How has James seen the way he communicates and inspires change with the scaling of the company? What has James observed as the core characteristics that great leaders share?
3.) Why does James believe that investors are inherently wary of the female and child clothing market? How did James see the funding rounds differ from round to round? What did James really look for in his early investors? How does investor value-add change with time and scaling?
4.) What have been James’ core learnings in managing a board with transparency and efficiency? James has said before “your board is right 50% of the time”. How does James look to determine which 50% is right vs wrong? What is a time when James has gone against the decision of the board? How did the situation result?
5.) Having raised over $130m in funding, how does James think about the balance between aggressive growth and capital efficiency? How does James assess when is the right time to pour fuel on the fire? How does James react to the mindset of “sustainable growth”? How do investors think about capital efficiency?
Items Mentioned In Today’s Show:
James’ Fave Book: Sapiens
Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.