How to sell AI to Main Street (Full Playbook)

About this episode

Get Your Complete Financial OS at https://startup-ideas-pod.link/brex_SIP I sit down with James Dickerson, the Boring Marketer, who owns Diesel Dudes, a mobile diesel repair business in Charlotte, North Carolina, and spent years running agencies for local businesses. James shows how to sell AI-built funnels to Main Street trades businesses doing $2 million to $20 million a year, starting with a Boring Funnels search that found 100 Dallas plumbers worth pitching. He walks through the leaks he finds on their landing pages, the funnel offers he'd sell, and how he'd win clients with the Dream 100, lumpy mail, and local meetups. If you know how to use coding agents, this episode gives you a full playbook for a service business built around booked jobs. Build funnels that sell: https://startup-ideas-pod.link/boring_funnels Timestamps 00:00 – Intro 01:23 – Sponsor: Brex 02:08 – Why sell AI to Main Street 03:05 – James's Background 04:32 – Finding and Picking a Niche 07:26 – The $2M to $20M Opportunity 09:02 – Plumbing and HVAC Market Size 10:56 – Underserved Trades Niches 12:38 – Auditing Five Dallas Plumbers 13:50 – Personal Agents vs. Google 15:02 – Selling Booked Jobs and Phone Calls 17:41 – Funnel Offer Overview 19:43 – Funnel Example 23:19 – Matching Ads to Funnels 24:14 – Chet Holmes and the Dream 100 28:18 – Branding your Firm 30:04 – Meta Ads for your firm 31:37 – Stacking Old School and New School Marketing Strategy 34:31 – Find, Pitch, Deliver 36:02 – Showing Owners the ROI 37:37 – Pricing your Offer 41:45 – Reporting With AI 42:33 – Closing Thoughts Key Points Main Street trades businesses doing $2 million to $20 million a year have budgets and few useful pitches in their inbox. James sells booked jobs and phone calls, since owners care about revenue and ROI over AI. The biggest leaks sit on the landing page: missing ad promises, hidden Google ratings, and buried booking buttons. Funnels with tripwires, instant prices, quizzes, and owner videos turn paid traffic into booked jobs. The Dream 100, lumpy mail, and local meetups build trust with owners over months. One free build in exchange for a case study gets you to paid work. The #1 tool to find startup ideas/trends - https://www.ideabrowser.com LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/ FIND ME ON SOCIAL X/Twitter: https://twitter.com/gregisenberg Instagram: https://instagram.com/gregisenberg/ LinkedIn: https://www.linkedin.com/in/gisenberg/ FIND JAMES ON SOCIAL X/Twitter: https://x.com/boringmarketer LinkedIn: https://www.linkedin.com/in/jadickerson/