Build With AI · Sep 18, 2026 · 25:18
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Join AI Operator Academy: https://www.skool.com/aioperatoracademy/about
Get all my FREE resources (including the ones mentioned in this podcast): https://www.skool.com/aioperatorhub/about
In this episode, I sit down with Charlie Madison, a member of AI Operator Academy, who sold two $999 paid assessments in his first 30 days and uncovered roughly $50K in additional pipeline. Charlie walks through the exact outreach system he used, a personalized video sent to his entire contact list, and breaks down how he qualifies hungry buyers and pitches the paid assessment with a 50 percent close rate. By the end, you'll have a real, replicable case study for landing your first AI services clients fast.
Timestamps:
(00:00) Intro: Meet Charlie Madison
(02:30) Charlie's 60-Second Outreach Video Strategy
(04:41) Breaking Down The Outreach Numbers
(07:01) AI Operator Academy Community Plug
(08:28) Charlie's Biggest Insight: Mutual Buy-In
(11:07) How Charlie Pitches The Paid Assessment
(14:20) Qualifying Leads: The Hungry Audience
(17:57) Selling Outcomes, Not AI
(21:55) Quantifying The $50K Pipeline
(22:43) Charlie's Advice On Joining AI Operator Academy
(24:23) Where To Find And Connect With Charlie
FIND ME ON SOCIAL:
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You can find Charlie here via Fire Busy Work:
🔗 https://firebusyworkfreepeople.com/