May 5, 2026

1454: How to Turn Your Diverse Career Experience into a Founder's Superpower w/ Connor McCormick

Apple Podcasts podcast player badge
Spotify podcast player badge
Castro podcast player badge
RSS Feed podcast player badge
Apple Podcasts podcast player iconSpotify podcast player iconCastro podcast player iconRSS Feed podcast player icon

In this episode, Brian sits down with Connor McCormick, the founder and CEO of Percheron AI, a trailblazing company bringing “agentic AI” to the legal industry. Connor shares his journey from a machine learning engineer to an entrepreneur, detailing the pivots and iterations—from AI consulting to micro private equity—that led him to build an AI co-pilot that helps attorneys prepare for litigation faster and more accurately. This episode is a masterclass for any wantrepreneur or entrepreneur looking to break into a traditional industry with a tech solution. Connor pulls back the curtain on how to build trust in a skeptical market, the importance of a rapid "time-to-value" loop, and how to leverage a diverse career path as your greatest entrepreneurial asset.

💡 What You'll Take Away For YOUR Business

  • How to use a consulting model to discover and validate a scalable product idea directly with your target customers.
  • Why "agentic AI" is the next frontier, and how building systems with internal checks and balances can overcome major user objections like "hallucinations."
  • The go-to-market strategy for entering a traditional, skeptical industry by focusing on security, privacy, and building trust from day one.
  • How a diverse career across engineering, product, and sales can become your secret weapon as a solo founder, giving you the confidence to learn and execute on any business function.
  • The power of the "fail fast" mentality: why trying multiple business ideas and knowing when to pull the plug is a critical skill for finding the one that works.
  • How to shorten your "time-to-value loop" by getting user feedback as quickly as possible to ensure you're not wasting time building something nobody wants.
  • The Ironman mindset in business: how endurance, iteration, and a willingness to "pound the rock" are essential for entrepreneurial success.

📝 About Connor McCormick

Connor McCormick is the founder and CEO of Percheron AI, an agentic AI co-pilot that helps attorneys prepare for litigation. With two AI-focused degrees and a decade of experience building real-world AI systems, Connor has a rich background spanning engineering, product, sales, and marketing at companies ranging from seed-stage startups to Fortune 500 enterprises. His journey showcases a relentless drive for learning and iteration, making him the perfect guide for entrepreneurs looking to leverage deep technical expertise to solve real-world problems.

🎯 Connor’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Be like water." Connor’s most impactful advice is to remain adaptable and fluid in the face of the countless obstacles you'll encounter in business and life.

📢 Memorable Quotes

  • “I've jumped around enough to be confident in my ability to just learn what I need to learn in order to succeed in that domain.” – Connor McCormick
  • “Percheron isn't meant to automate the job of an attorney. It's just to make it go a lot faster because in any given day...six of those hours are just like reading through documents, trying to find a needle in a haystack.” – Connor McCormick
  • "One of the best things you can do to ensure your success is making sure you're keeping that time-to-value loop as short as possible, making sure that you build something and then you get feedback on it as quickly as possible." – Connor McCormick

🔗 Links & Resources