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Can AI Really 2X Output and Break Legacy Business Models? | Dru Armstrong, AffiniPay CEO
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Manage episode 496056052 series 3341253
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
-------------------
Austin Next Links: Website, X/Twitter, YouTube, LinkedIn
Ecosystem Metacognition Substack
166 episodes
Fetch error
Hmmm there seems to be a problem fetching this series right now. Last successful fetch was on October 01, 2025 12:26 ()
What now? This series will be checked again in the next day. If you believe it should be working, please verify the publisher's feed link below is valid and includes actual episode links. You can contact support to request the feed be immediately fetched.
Manage episode 496056052 series 3341253
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
-------------------
Austin Next Links: Website, X/Twitter, YouTube, LinkedIn
Ecosystem Metacognition Substack
166 episodes
All episodes
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