The Mergers Podcast

Using AI to assess Start-Ups [Special Guest - Billy Gallagher, Prospect]

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In this episode of The Mergers Podcast, Rory and Ken are joined by Billy Gallagher, founder of Prospect, to explore the intersection of venture capital, startups, and career decision-making. Billy brings a wealth of experience, having started his journey at Stanford, covering early tech giants like Snapchat and DoorDash, and later joining Rippling as employee #30, helping scale it to 1,000 employees.

Key Highlights:

  • The Prospect Mission: Billy explains how Prospect helps employees make better decisions when joining startups by providing tools to assess equity value and using proprietary AI models to score startups—offering a VC-style approach to career choices.


  • Startup Screening Secrets: Billy shares his process for identifying high-potential startups, including looking for early signs of product-market fit and visionary founders, and why joining a company at the “hockey stick inflection point” can maximize equity upside.


  • State of Venture Capital: Get Billy’s take on the current VC landscape, including the boom in AI-driven startups, lingering hype-driven valuations, and the shift toward lean, disciplined business models.


  • AI in Startups: Billy reflects on balancing shiny object syndrome with practical AI applications, highlighting how models can now act as endless research interns to improve decision-making.


  • Building Networks and Careers: Advice on managing your professional network, evaluating startup opportunities, and why now is a great time to get into the startup ecosystem.


Whether you’re a startup founder, a VC enthusiast, or someone navigating career choices in tech, this episode is packed with actionable insights on leveraging data, building networks, and making the most of equity opportunities.