21 Hats Podcast Dashboard: You Probably Should Be Doing More with AI
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Oct 13, 2025 Ted Wolf, experienced entrepreneur and co-founder of GuideWise, shares insightful AI strategies for businesses of all sizes. He discusses the common pitfalls of AI pilots and emphasizes the importance of partnership and governance. Ted offers practical steps for small businesses to start their AI journey, including using ChatGPT for immediate SWOT analyses against competitors. He highlights the vital role of training and trust-building to overcome employee resistance while cautioning against sharing sensitive data on public platforms.
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Bootstrapping To Major Exit
- Ted Wolf built Wolf Advisory International from $1,000 to ~800 people and sold it to Iron Mountain.
- He attributes growth to surrounding himself with talented people and learning from people mistakes.
AI Is A Full-Circle Productivity Moment
- Ted sees AI as a full-circle technology moment similar to early computing adoption.
- He expects AI to increase productivity and open broad opportunities for businesses and individuals.
AI Success Requires Three Alignments
- AI adoption success hinges on business readiness, tech fit, and people alignment.
- Pilot failures often come from trying to implement AI without the right team, governance, and change plan.