# # 161 How I'm AI-maxxing boomer businesses to make f*ck you money

Page: https://stenobird.com/podcast/build-with-ai-6407453/161-how-i-m-ai-maxxing-boomer-businesses-to-make-f-ck-you-money
Text version: https://stenobird.com/podcast/build-with-ai-6407453/161-how-i-m-ai-maxxing-boomer-businesses-to-make-f-ck-you-money.md
Podcast: [Build With AI](https://stenobird.com/podcast/build-with-ai-6407453)
Published: 2026-04-29T18:22:28+00:00
Episode link: https://share.transistor.fm/s/ce5600ca
Audio file: https://media.transistor.fm/ce5600ca/092cbc6a.mp3
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JSON: https://stenobird.com/v1/public/podcasts/build-with-ai-6407453/episodes/161-how-i-m-ai-maxxing-boomer-businesses-to-make-f-ck-you-money
Duration seconds: 2173

## Resource

Free audit template Corey is giving away — https://audittemplate.ai In this episode, I sat down with Chris Koerner and outlined how I sell AI assessments to small businesses. Timestamps 00:00 – Intro 00:33 – The $1,000 AI audit pitch 01:10 – The lunch conversation that started it all 02:23 – Why 99 out of 100 owners need this 02:57 – Why Loom screen recording failed 04:25 – From Zoom calls to a voice agent 05:31 – Meet Annie, the AI interviewer 06:17 – Live demo of the voice agent 08:06 – How the voice agent was built (Retell + skills) 10:18 – Walking through a real assessment in Gamma 12:00 – The effort vs impact matrix 13:00 – Wedding venue saves 8 hours with Dash This 15:16 – Pricing journey: free to $1,000 17:30 – Why charging more makes upsells easier 18:02 – The full upsell menu breakdown 22:00 – Custom GPT knowledge system for a business broker 24:46 – Which industries this works best for 25:53 – Seven ways to find clients with no followers 26:39 – Hosting a local AI meetup 27:30 – Door-knocking businesses in 2026 29:25 – Using free audits to land warm contacts 30:30 – Running free AI office hours 31:30 – Hard-won lessons and the speed-to-lead upsell 34:36 – The simple Claude prompt that builds the audit 35:33 – Where to find Corey Key Points The business started from one lunch where a friend said he'd pay $1,000 just to be followed around for a day. After validating with 50–100 owners, Corey found 99 out of 100 small business owners need this — they just don't know which AI tools to use. The upsell menu is built into the report. Common follow-ons: process optimization ($3K–$5K), Zapier or Make automation builds ($1K–$3K), custom GPT knowledge systems, CRM setups (high-level CRM at $3K–$5K), and speed-to-lead AI agents tied directly to revenue. The seven-way cli…

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