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

An open conversation about PMF, pivot, M&A and venture capital investment

Welcome to this new episode of Explore! 😎

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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! 

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Learn more about ⁠⁠⁠Sam, and Green Visor.


Timestamps: 

00:00 Introduction

00:44 Recap of Episode One

01:31 The Journey to Volley Travel

02:19 Pivoting the Business Model

04:14 Challenges and Lessons Learned

07:03 The Acquisition Process

17:53 Transition to Venture Capital

25:27 Empathy in Investing: A Double-Edged Sword

27:07 Identifying Green and Red Flags in Investments

27:39 The Importance of Technology in Early-Stage Companies

31:25 The Role of Charisma in Founders

34:42 Navigating the VC Landscape: Tips and Insights

40:07 Advice for Aspiring Entrepreneurs and Investors

44:39 Inspiring Stories and Final Thoughts

Discussion about this podcast

Explore (Startups and VC)
Explore (Startups Founders and Investors)
Explore tells the stories behind the success of entrepreneurs and investors around the world.
Hi there👋, I'm Hugo Rauch, a financial analyst at Microsoft and the host of Explore. I've always been fascinated by startups. In 2022 I wrote a 100 pages paper on the startup economy. In 2023, I wanted to learn from experience and I started Explore.
I've made myself the goal of supporting early-stage founders with theoretical and practical learnings.
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*Opinions expressed are solely my own and do not express the views or opinions of my employer.