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

Join our AI Operator Academy Community where we help entrepreneurs start and scale a profitable AI services business: https://www.skool.com/aioperatoracademy/about 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 08:29 - Booking the follow-up call off the explainer video 09:30 - Why he charges $5K/month over six months, not $2K 11:45 - Solve rich people problems 12:48 - Walking through the full deliverable package 13:19 - The one-pager and proof kit 13:34 - Why he built a 7-minute NotebookLM explainer video 15:49 - How the explainer video preempts objections 17:39 - Selling to secondary decision-makers without being in the room 19:14 - His real numbers: $65,734 from one $97 workshop 20:37 - Why he'd scale this into in-person workshops 22:41 - Where to follow Dino and final thoughts Key Points Dino closed a $30,000 AI Concierge retainer, $5,000 a month for six months, despite having dyslexia, no coding background, and no marketing expertise. Proof the AI Operator Academy playbook works for anyone willing to run it as taught. His funnel gets him paid at every single step. A $97 workshop with a built-in $497 early-bird upgrade to the paid assessment, then a $797–$997 assessment, then the retainer. He made $5,734 before he ever got on a sales call. From one $97 workshop with 20 attendees, Dino generated $65,734 in total tracked value and a 44% close rate turning assessments into retainers. His standout move: he runs the finished assessment report through NotebookLM (Gemini) to generate a seven-minute AI explainer video, then sends it to the prospect ahead of the sales call. It becomes an asset the client can forward to a spouse, partner, or financial advisor who needs to sign off. He charges $5,000 a month on a six-month contract instead of pitching a flat total, and always frames the price against the dollar savings ("pay $30K to get $250K back") rather than naming the full number upfront. His advice to new operators: don't overcomplicate the discovery questions. Even with 15 years of orthodontic industry expertise, his actual assessments still trace back to the same core questions taught in the program, deep industry knowledge just makes the calls longer, not more accurate. He never pitches the retainer as the only option. Every prospect is told they can take the full assessment blueprint to any AI developer they want. That transparency, plus already being a paying customer, is what makes them choose to hire him instead. Claude, used to build the presentation deck and customize the assessment questionnaire for the orthodontics niche - https://claude.ai NotebookLM (Gemini), used to turn the finished assessment into a seven-minute explainer video for prospects - https://notebooklm.google AI Operator Academy, the community where Corey and Dino teach people how to sell AI assessments and AI Concierge retainers - https://aoa.community FIND ME ON SOCIAL X/Twitter: https://x.com/coreyganim Instagram: https://www.instagram.com/coreyganim/ LinkedIn: https://www.linkedin.com/in/coreyganim/ YouTube: https://www.youtube.com/@coreyganim FIND DINO ON SOCIAL Instagram: https://www.instagram.com/dinowatt/