July 23, 2025

Can AI Really 2X Output and Break Legacy Business Models? | Dru Armstrong, AffiniPay CEO

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How do 100X engineers, cheap development, and AI-everywhere workflows flip slow-moving industries and legacy business models? AffiniPay CEO Dru Armstrong joins to discuss how vertical fintech and generative AI reshape professional services, the evolution of a new small-business software stack, and Austin’s climb to a top five tech cities. 

Highlights

  • 00:00 AffiniPay overview & mission
  • 02:57 Why solo firms need vertical SaaS
  • 05:45 Unified platform vs best-in-class tools
  • 08:26 AI’s early impact on law and accounting
  • 11:39 Billable-hour model under pressure
  • 14:20 Where AI in services is heading next
  • 17:03 Culture change: adopting AI at work
  • 20:14 Automating routine legal workflows
  • 30:19 Manufacturing Cost crashes & roles
  • 31:40 Austin emerging as a FinTech frontier
  • 34:54 Building a legal-payments platform locally
  • 39:34 Generative AI’s effect on big-law practice
  • 45:55 Faster product cycles with AI tools
  • 48:35 How engineering roles are evolving
  • 53:34 What's Next Austin" “I want Austin in the top five."


Guest Bio
Dru Armstrong is the Chief Executive Officer of AffiniPay, LLC, a leading financial technology software provider for professionals, since July 2021, where she has implemented and executed a new strategic direction for the business, including its transformative acquisition of MyCase. Prior to joining AffiniPay, Ms. Armstrong served as Chief Executive Officer of Grace Hill, LLC, a real estate technology and software provider, from June 2016 to July 2021, and as Chief Product Officer from September 2015 to May 2016. Ms. Armstrong received a Master of Business Administration from the University of Chicago Booth School of Business, a Juris Doctorate from the University of Chicago Law School, and a Bachelor of Arts in Economics from Columbia University.

Episode Links
Dru Armstrong
Affinipay
Kaleidoscope September 2-4, 2025

 

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