21 Hats Podcast

I Have to Figure This Sh*t Out

9 snips
Nov 25, 2025
Liz Piccarazzi, CEO of CityBin, shares her struggle with AI adoption amidst a $400,000 tariff bill, while Jaci Russo, CEO of Brand Russo, boasts about her successful integration of generative AI that generates ten vetted leads daily. Ted Wolf, an AI consultant, stresses the importance of documentation in AI workflows. The trio reflects on a challenging year, with Jaci lamenting a failed hire and Liz humorously acknowledging the reliability of New York City's trash. Together, they navigate the complexities of AI in their businesses.
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ADVICE

Stop Spinning — Outsource System Cleanup

  • Hire someone to organize systems and passwords if you're spinning your wheels on AI adoption.
  • A contractor or part-time expert can unlock progress faster than struggling alone.
ADVICE

Learn AI By Teaching And Doing

  • Learn by doing and then teach others; running classes forces you to master tools.
  • Use short, practical exercises to internalize AI capabilities instead of only reading theory.
INSIGHT

Workflows Power Successful Automation

  • Document workflows first because bots need clear process steps and data sources.
  • Without documented processes your automation will fail and tribal knowledge remains hidden.
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