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Run big decisions past an AI board of advisors: a pessimist, an outsider and a customer
Tim Leary, owner and founder of Handy's, a handyman and home-maintenance company in Salt Lake City with seven trucks and an office team, on the Blue Collar Builders podcast
He prompted and set up AI agents that act as a board of advisors. When an idea comes up, he puts it in and they talk to each other: one is a pessimist, one looks at it from completely outside the industry, and one takes the consumer's view. Then they come back to him with the good, the bad and the ugly. He is also using AI to work out strategies for building a handyman price book that estimators could learn in a week (not in use yet). The podcast doesn't name the AI tools.
ChatGPT Free $0; Go $8/mo; Plus $20/mo · Claude $17/mo billed annually ($20 monthly); free plan available (his tools aren't named; the DIY version below works in one chat)
Easy · or we do it from $149/mo
Varies
The problem
A fast-growing owner who calls himself a natural optimist can head down paths that aren't the right one for that stage of the business, and has no board to push back.
What happened
He says it gives him the ability to see things he doesn't naturally see, especially since he's in the business every day. Handy's revenue (about $365,000 from May to December 2024 and $1.2 million in 2025) is company context, not an AI result. Self-reported.
Quoted in the source: Tim Leary, owner, Handy's. Source: Blue Collar Builders: Tim Leary, Handyman business "Handy's" is generating $1.2M with an AI Board of Advisors (2026-06-24) · Added 2026-10-18.
How to set it up yourself
- What Handy's does: the owner puts a business idea to a set of AI agents he prompted to play a pessimist, an outsider from another industry and a customer; they discuss it and report back the good, the bad and the ugly. The tools aren't named, so the steps below are a one-chat DIY version.
- Make a ChatGPT or Claude project called "Board" and paste the prompt below into its instructions, with a few lines about your company: services, area, team size, this year's goals.
- When an idea comes up (a new service, a hire, a price change, a second location), write it out in a few sentences with the numbers you know, and ask the board to meet.
- Read the risks it raises and check the ones that matter with real numbers or a real customer. The decision stays yours; use the board to find blind spots, not to make the call.
Copy-paste prompt
Act as a three-person advisory board for {COMPANY NAME}, a {DESCRIPTION, e.g. handyman company in Salt Lake City with 7 trucks}. Members: 1) a pessimist who looks for what will go wrong and what it will cost, 2) an outsider from a different industry who questions our assumptions, 3) a typical customer of ours. For the idea I give you, have each member respond, then let them react to each other once. End with: the good, the bad, the ugly, the one question I must answer before deciding, and the cheapest way to test it first. Be blunt; don't flatter the idea.One short email a day: 3 new AI use cases from real small businesses, each with its source and setup steps, plus a Tool of the Day. Free, no spam, unsubscribe anytime.
Rather not do it yourself?
We'll set this up in your tools, in your voice, tested. $149/mo with setup included (6-month minimum), or $497 pay-once. Satisfaction guarantee: we'll fix it until it works. Pay-once setups: or we refund your setup fee. $149/mo plan: cancel in the first 30 days and we refund your first month. Terms. We reply within 1 business day.
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