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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Austin Next Links: Website, X/Twitter, YouTube, LinkedIn
Ecosystem Metacognition Substack

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