From the Ritz-Carlton in Dallas, George Wright III interviews Tucker Bern, who helps manage a complex family office spanning multiple industries and chose to focus on simplifying AI for real business use. Bern created Caddy, a locally installed “command center” built on Claude that uses a personalized intake to learn a user’s needs and then supports tasks like email triage, calendar/meeting prep with web research, diligence, reporting, workflow automation, and even software building, with about 100 built-in skills including an “auditor” to review and dry-run code. He shares examples of replacing tedious job-review work and helping a non-coder build a lead-scraping app in 2.5 days, emphasizing output gains beyond 20% without aiming to cut staff.

00:00 Get 20 Percent More

00:38 Show Intro And Guest

01:56 Why Focus On AI

04:02 Meet Caddy Platform

05:10 Setup And Intake

06:36 Real Workflow Wins

07:15 Skills And Auditor

08:20 Who Benefits Examples

11:49 Productivity Not Layoffs

13:49 Security And Ownership

15:26 How To Use Daily

17:48 Why You Must Adopt

20:49 Vision And Passion

22:15 Where To Learn More

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George Wright III

“It’s Never Too Late to Start Living the Life You Were Meant to Live”

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Tucker Bern is a dynamic entrepreneur and investment leader who currently serves as the CEO of a specialized AI Automation company and President of Bern Investment. At 29, Tucker manages a family office with nine figures in capital following the landmark 9 figure sale of his family’s 1,200-employee enterprise in 2025. His AI firm provides cutting-edge voice, text, and automation solutions for diverse sectors, including medical, accounting, and the trades (HVAC, roofing, pest control, etc). A versatile strategist, Tucker also leads business development for the family’s functional wellness brand, which they successfully scaled from zero to over seven figures in just 18 months across Iowa and Texas. Combining high-level capital stewardship with a "boots-on-the-ground" approach to tech innovation, he focuses on leveraging automation and strategic investment to drive rapid growth and operational excellence.

Links: meetcaddy.com, hi@meetcaddy.com.

https://createassistants.ai/

https://www.instagram.com/thetuckerbern/