Beyond the Buzzword of AI with Rob May

Cockpit Counsel

Beyond the Buzzword of AI with Rob May



Legal teams need to deploy modern technology, but many don’t know where to start when it comes to AI. We’re here to give you a high-level overview of this complex topic. Watch this episode to learn from Rob May, an expert in the space.

Rob has founded an AI company, made over 70 early-stage AI investments, writes one of the world’s most popular AI newsletters, and hosts the podcast “Investing in AI” about AI’s impact on business models, markets, products, and consumer behavior.


  • 00:00 Introduction
  • 00:26 What is your preflight ritual?
  • 01:31 Tell us a bit about your career path and how you ended up at LinkSquares
  • 04:37 What perspective have you gained as a business operator after being an investor?
  • 07:32 What is the state of AI right now? What are some trends that you’re seeing?
  • 12:33 How do you justify the integrity of what AI is learning? 
  • 16:02 What’s the immediate future of AI over the next two to five years?
  • 20:24 How are you thinking about the legal team? What was the driving force for you to bring in counsel? 
  • 27:33 When building a team, what traits do you look for from high-performance scalable teams? 


Tim Parilla Headshot
Tim ParillaChief Legal Officer, LinkSquares
Rob May headshot
Rob MayAI Expert and Founder/CEO, BrandGuard

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