Navigating the downside of a startup and becoming a VC investor - Sam Wen (Square, Volley Travel, Green Visor Capital) - S2 Ep18

Welcome to this new episode of Explore! 😎Thank you for your continuous support, I wanted to let you know that the best way to send me some love is to give a 5 stars review ✨ on Spotify/Apple podcast. Thank you OpenVC for keeping this content free for our listeners. OpenVC is a fundraising platform used by 10,000 founders and 5,000 investors. You can use the code: "EXPLORE” to upgrade to OpenVC Premium and get a 20% discount. 📈🔥This is part 2/2 of this podcast with Sam Wen, a partner at Green Visor Capital, founder of Volley Travel and co-founder of Square. In episode 1, we went through the early days of building Square, and all the reasons behind Square's success. In this episode, Sam shares the story behind Volley Travel, we talked about the challenges of pivoting as a VC-backed startup, how they secured an acquisition, and the value of having a strong engineering-led team. Sam also shares his vision of Venture Capital and offers valuable insights for aspiring entrepreneurs and investors, emphasizing the significance of operator experience and scalability in startups. Have a great episode! Listen on 🟢Spotify or on 🟣Apple Podcast.Learn more about Explore: ⁠⁠⁠LinkedIn⁠⁠, ⁠⁠Newsletter⁠⁠. Learn more about ⁠⁠⁠Sam, and Green Visor.Timestamps: 00:00 Introduction00:44 Recap of Episode One01:31 The Journey to Volley Travel02:19 Pivoting the Business Model04:14 Challenges and Lessons Learned07:03 The Acquisition Process17:53 Transition to Venture Capital25:27 Empathy in Investing: A Double-Edged Sword27:07 Identifying Green and Red Flags in Investments27:39 The Importance of Technology in Early-Stage Companies31:25 The Role of Charisma in Founders34:42 Navigating the VC Landscape: Tips and Insights40:07 Advice for Aspiring Entrepreneurs and Investors44:39 Inspiring Stories and Final Thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit climateventuresvco2.substack.com