Transcribed
Why Most Businesses Get AI Wrong
Jun 19, 2026 ·
38m 22s
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Why Most Businesses Get AI Wrong
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Description
Most owners buy the AI tool, skip the strategy, and wonder why nothing improves. Jason Alexander, CEO of Chief AI, explains why AI is a people and process problem, not...
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Most owners buy the AI tool, skip the strategy, and wonder why nothing improves. Jason Alexander, CEO of Chief AI, explains why AI is a people and process problem, not a tool problem.
Hand someone a guitar, and you still hear no music until you teach them to play. Jason has lived the operator side of this. Over 20 years, he built and scaled a staffing and consulting business to roughly 100 million dollars before selling, and now he helps founders turn AI into practical, measurable results.
In this conversation with David Carr, he breaks down the three-year success roadmap he uses to determine where AI actually belongs, why "assess, one quick win, then scale" beats chasing silver bullets, and how to make AI part of your culture rather than hiding it from clients. He also gives a straight answer on the fear everyone carries: AI is a force multiplier, not a layoff plan. Arm 100 people to produce 400, rather than cutting headcount to save payroll.
If you are a founder or leader trying to make AI pay off without losing what makes your business human, start here.
Connect with Jason:
ChiefAI: https://chiefai.co
Jason Alexander on LinkedIn: https://www.linkedin.com/in/jasonalexander
Free AI Readiness Score: https://chiefai.co/ai-readiness-assessment/
Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.
Connect with Steward Your Business:
https://www.youtube.com/@steward_your_business
show less
Hand someone a guitar, and you still hear no music until you teach them to play. Jason has lived the operator side of this. Over 20 years, he built and scaled a staffing and consulting business to roughly 100 million dollars before selling, and now he helps founders turn AI into practical, measurable results.
In this conversation with David Carr, he breaks down the three-year success roadmap he uses to determine where AI actually belongs, why "assess, one quick win, then scale" beats chasing silver bullets, and how to make AI part of your culture rather than hiding it from clients. He also gives a straight answer on the fear everyone carries: AI is a force multiplier, not a layoff plan. Arm 100 people to produce 400, rather than cutting headcount to save payroll.
If you are a founder or leader trying to make AI pay off without losing what makes your business human, start here.
Connect with Jason:
ChiefAI: https://chiefai.co
Jason Alexander on LinkedIn: https://www.linkedin.com/in/jasonalexander
Free AI Readiness Score: https://chiefai.co/ai-readiness-assessment/
Become a supporter of this podcast: https://www.spreaker.com/podcast/business-roundtable--6049255/support.
Connect with Steward Your Business:
- Book a Leadership Clarity Call: https://calendar.stewardyourbusiness.com/cc
- Call: +1 909.404.9865
- Website: https://stewardyourbusiness.com
- LinkedIn: https://www.linkedin.com/in/davidwcarr
https://www.youtube.com/@steward_your_business
Information
| Author | David W. Carr |
| Organization | Steward Your Business |
| Website | - |
| Tags |
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