Landing a $30K Retainer BRAND NEW to AI (Case Study)

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In this episode, I sat down with Dino Watt, an orthodontics industry consultant with zero technical background, who used the exact AI Operator Academy playbook to land a $30,000 consulting deal in under three months. Dino walks through his entire funnel live: a $97 workshop that pre-sold assessments before he ever taught it, a $797–$997 paid AI assessment, and a standout add-on nobody else is doing, an AI-generated explainer video that turns his report into a seven-minute video his clients can forward straight to a business partner or spouse. He breaks down the actual numbers: $5,734 collected before a single sales call, a 44% close rate, and a $5,000-a-month, six-month AI Concierge retainer closed off the back of an assessment he got paid to deliver. By the end of this episode, you'll have a full blueprint for turning a paid workshop into a five-figure retainer, even if you've never written a line of code.

Timestamps:

00:00 - Intro: meet Dino Watt

00:50 - Not technical, dyslexic, no coding background

01:35 - Joining AI Operator Academy with his wife Shannon

02:39 - The $30K AI Concierge retainer overview

03:09 - Using Claude to build his podcast slides live

04:55 - The filter: effectiveness, efficiency, quality

05:27 - Pricing the $97 workshop and early bird upsells

06:20 - Upselling the $997 paid assessment

07:20 - Doing the assessments and giving one testimonial freebie