I've been selling AI consulting for a year, but last week I interviewed a guy who puts my model to shame.
His name is Dino Watt and he recently closed a $30,000 AI consulting retainer. $5,000 a month, six-month contract. That's more than double what my highest-paying concierge client pays me.
I've spent the last year selling AI assessments and concierge retainers to small businesses. Dino came on my podcast this week and screen-shared his entire playbook. This article is that playbook, in step-by-step format to help you land your first retainer.
In this article:
- The positioning shift that makes retainers close themselves
- The three-rung ladder: paid workshop → paid assessment → retainer
- The exact pricing at every rung, with Dino's real numbers
- The 7-minute deliverable that does the selling for you
- The math behind $65,734 from one $97 workshop
- The two-path close (word for word)
- The 10 actions I'd take starting from zero
Most people trying to land their first AI retainer lead with the retainer. That's exactly backwards, and it's why they're stuck at zero.
Before we dive in, I combined all the best practices, prompts, and resources from this article into one simple downloadable playbook.
Let's get into it.
The positioning shift: never sell the retainer first
Dino is 53. Dyslexic, ADHD, barely graduated high school. His words on coding: put a gun to his head and he's a dead man. No marketing background, no tech background. His day job for the last 15 years has been culture and communication consulting for orthodontic practices.
So how does a guy like that out-close me on retainers?
He never sells the retainer.
He sells a filter. Dino's pitch to his audience is simple: you're being bombarded with AI tools and you're terrified of buying the wrong thing. I'll give you a filter so you can make better decisions. That filter is the Three Outcomes. Every tool and workflow gets judged on whether it improves Effectiveness (makes you money), Efficiency (saves you time), or Quality (improves your product and customer experience). That's the framework we teach inside AOA, and it's the spine of everything Dino delivers.
The retainer shows up at the very end, almost as an afterthought. By then the client has already paid him twice and trusts him completely.
I call this the Paid-Every-Step Ladder. Three rungs, and you collect money on every single one:
- Paid workshop ($97): teach the filter
- Paid assessment ($497-$997): apply the filter to their business
- Retainer ($5,000/month): implement what the assessment found
No free discovery calls. No "pick your brain" coffees. No proposals rotting in someone's inbox.
If they won't pay $97 to learn from you, they were never paying $5,000 a month.
Rung 1: The $97 workshop
Dino built a three-hour virtual workshop on AI basics for orthodontists. One email to his list of roughly 5,000. No ads.
21 people in the room. 15 paid (he comped 6 existing clients). Some caught a $49 early-bird rate, the rest paid $97.
Three hours of teaching the Three Outcomes filter, applied to their industry. That's it. He's a trainer by trade, so this rung plays to his strength. But the content itself came from what we teach, customized to his niche.
Two things make this rung work:
The niche can afford you. Dino quotes Alex Hormozi on this: solve rich people problems. Orthodontists run practices doing seven figures. A $997 assessment isn't a purchasing decision for them, it's a rounding error. Pick a niche where your eventual retainer price is normal, not shocking.
The upsell starts before the workshop. The moment someone registers, the confirmation page offers the assessment: normally $997, but $497 if you grab it right now. Four people bought before the workshop even happened. He was up over $2,000 before delivering a single minute of content.
Rung 2: The assessment (and the deliverable that sells the retainer)
At the end of the workshop, Dino pitches the assessment again: $997, or $797 if you buy within 24 hours. Three people closed on the spot. Two more came in days later at full price.
That's a 44% close rate from the workshop room.
The assessment itself follows the process we teach: a deep discovery call, transcript into Claude, and out comes a scored report mapping AI solutions to their specific pain points against the Three Outcomes. You don't need to know how to build anything to deliver this. You need to ask good questions and let the AI do the analysis.
But Dino added one thing that I'm now stealing for my own business.
The 7-minute explainer video. He runs the finished assessment through Notebook LM (now Gemini's video tool) and generates a short animated video that walks the client through their own report. Their pain points, in their words, played back to them with the plan to fix each one.
Here's the prompt structure he adds to his assessment build:
EXPLAINER VIDEO PROMPT
Take this completed AI assessment report and write a prompt for Notebook LM that will generate a ~7 minute explainer video.
The video must:
- Address the client by name in the opening line
- Lead with the single biggest outcome (e.g. "designed to give you 5+ doctor-hours back every week")
- Replay the client's own stated pain points in their own words
- Walk through the plan as: "First we'll do X. Second, Y. Third, Z."
- End with the projected annual savings figure from the report
Why this matters for landing the retainer: your buyer is almost never the only decision-maker. There's a spouse, a partner, a business manager, a financial coach. One of Dino's prospects promised her financial coach she wouldn't buy anything without running it past him first. Instead of hoping she could re-explain a 20-page report, she forwards a 7-minute video.
The video does your selling in rooms you'll never be in.
He also has Claude prep his sales call from the same assessment:
SALES PREP PROMPT
From this assessment report and discovery call transcript, give me:
1. The client's 3 biggest pain points, ranked by emotional weight
2. Their stated financial goals and any hard numbers attached
3. Which sections of the report to slow down on during the walkthrough call, and which to move through quickly
4. A suggested call flow that connects our plan to their #1 goal
Real example: one client wants to sell her practice in five years for at least $1.2 million. Claude flagged that her EBITDA needs to hit roughly $500-600K to get there. So Dino's entire walkthrough connected every recommendation to that exit number. She's expected to sign this week. That's a target, not a closed deal yet, and I'm labeling it as one.
Rung 3: The two-path close
After the assessment walkthrough, the retainer pitch is one sentence. Here's the structure, pulled straight from how Dino (and I) run it:
TWO-PATH CLOSE SCRIPT
"I promised you a blueprint, and this is it. You now have everything you need to go save $[X] a year.
You've got two options. You can take this blueprint and implement it yourself, or hand it to any AI person you trust. It's yours.
Or you can hire us to do it for you. I've got the people and the process in place. You sit back and collect the results.
Which one sounds better to you?"
No pressure. No countdown timers. The genuine willingness to let them walk is what closes the deal, because it proves the assessment wasn't a trojan horse.
And think about who's hearing this. An orthodontist with patients, staff, and a practice to run. Implementing the blueprint themselves means 200 hours they don't have. Paying $30,000 to capture $250,000 in projected annual savings is the easiest math they'll do all year. (That $250K is the assessment's estimate, not audited savings, so say so on your calls too. Honest numbers close better than inflated ones.)
One sales psychology note from Dino worth bolding: he never says "$30,000." It's $5,000 a month. The only time the full number comes up is in the ROI comparison: pay 30 to get 250 back.
The math behind $65,734
From one $97 workshop, before marketing beyond a single newsletter email:
- Workshop revenue: ~$1,500 (15 paid seats, mix of $49 early bird and $97)
- Assessment revenue: ~$4,200 (4 pre-workshop at $497, 3 at $797, 2 at $997)
- Cash collected before delivering a single assessment: $5,734
- First retainer closed: $30,000 ($5,000/month, 6 months)
- Second retainer: expected this week (target, not proven)
- Behind that: 3 more assessment clients in the pipeline
Total value from one workshop: $65,734. The closed, verifiable portion is the $5,734 collected plus the $30K contract signed. The rest is pipeline, and Dino presents it that way too.
Notice the structure of the funnel math: the workshop and assessments aren't really the money. They're paid trust-building. The retainer is 84% of the total value. But you can't skip to it. The retainer only closes at that price because the client has bought from you twice, watched you deliver twice, and seen their own numbers in your report.
Getting your first client: who this works for
This model works if you have at least one of these:
- A niche you already serve or understand (Dino: 15 years in orthodontics)
- An email list, even a small one (his took 10 years to build to 5,000, but 21 registrants means you'd get similar results from a list of a few hundred in a tight niche)
- A willingness to run a warm-network version: 5-10 personal invites to business owners you know, same ladder, smaller room
Who this isn't for: if you want to skip the assessment and go straight to building agents for strangers, this playbook won't save you. The ladder is the product. And if your niche can't afford $997 for an assessment, fix the niche before you fix the offer.
One more thing Dino said that should remove your last excuse: not knowing the industry deeply can actually be an advantage. His discovery calls run 90 minutes because his expertise pulls him into rabbit holes. The core assessment questions, the basic ones we hand you, produce the report either way.
You don't need to be the expert. You need to be the person holding the filter.
The first 10 actions I'd take from zero
- Pick one niche where owners clear $500K+ and already pay for consulting.
- Customize the assessment question bank to that niche (feed Claude what you know about their world and have it adapt the questions).
- Build a 3-hour workshop teaching the Three Outcomes filter applied to that niche. Charge $97.
- Set up the registration flow with the assessment upsell on the confirmation page: $997 anchored, $497 pre-workshop price.
- Fill the room with one email to your list, or 20 personal invitations if you don't have a list.
- Deliver the workshop. Close the assessment at the end with a 24-hour $200 discount.
- Do 1-2 free assessments for existing contacts first to collect testimonials before the paid ones land.
- Run every paid assessment through the discovery-call → Claude → scored report process.
- Generate the 7-minute explainer video and send it as the teaser before the walkthrough call.
- On the walkthrough call, run the two-path close. Quote monthly, not total. Anchor against their projected savings.
Then do it again next month. Dino's second workshop already has 10 paid seats, zero comps.
Final thoughts
The reason most people never land their first AI retainer is that they ask for marriage on the first date. Dino got paid to build trust three separate times before the retainer conversation ever happened, and by then it wasn't a pitch. It was the obvious next step.
He's 53, can't code, and plans to ride this until the wheels fall off.
Your excuses are gone.
Watch the full breakdown with Dino on the Build With AI podcast.
If you want the assessment templates and playbook resources from this article in one place, grab the free bundle here.
And if you want the complete business in a box (the trainings, the customized assessment templates, and 242+ operators selling AI services right now), join us inside AI Operator Academy.
Follow me @coreyganim for daily posts on growing an AI services business. If this playbook helped, repost it so other operators see it.
