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Write the message yourself, then ask ChatGPT to make it a little softer
Cody Jackson, founder and owner of Black Bear Roofing and Exteriors in the Springfield, Ohio area (a team of almost 15), on the Builders Bible podcast
The company uses ChatGPT, Gemini and others "for the proper ways": not writing its emails for it, but "help me out with this". When something he wrote sounds too direct, he asks it to "make this a little softer", so the message is still his.
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ChatGPT
The problem
He's a very direct person and sometimes comes across that way in writing, without meaning to hurt feelings.
What happened
He says it keeps the personal touch because he still wrote it, and warns that owners who let AI write their contracts and emails lose that touch. No figures given. Self-reported.
Quoted in the source: Cody Jackson, owner, Black Bear Roofing and Exteriors. Source: Home Service Studs Podcast (Builders Bible): Bear-ing Growth: Cody Jackson on Scaling Black Bear Roofing and AI Estimation (2026-08-31) · Added 2026-10-19.
How to set it up yourself
- What Black Bear Roofing does: the owner writes the email or text himself, then asks ChatGPT to soften the tone without changing what he's saying.
- Write your message the way you'd say it, facts and all. Don't let AI write it from nothing.
- Paste it into ChatGPT with the prompt below. Compare the two versions and keep your facts, dates and prices exactly as you wrote them.
- Read the softer version out loud once; if it doesn't sound like you, ask for "less formal" or put your own words back in before sending.
Copy-paste prompt
Here's a message I wrote to {WHO, e.g. a homeowner / a crew lead / a supplier}: {MESSAGE}. I'm a direct person and I don't want this to come across as harsh. Make it a little softer and friendlier, keep it about the same length, keep every fact, date and price exactly as written, and don't add anything I didn't say. Then list what you changed.The $39 Plumbing & HVAC AI Starter Kit has ready-to-use call scripts, missed-call texts, estimate follow-ups and review templates, built from 18 real, sourced setups. Instant download, 30-day refund.
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Tools used
ChatGPT
General AI assistant for writing, research, brainstorming and analysis.
From Free $0; Go $8/mo; Plus $20/mo; Pro $100/mo (checked 2026-10-17)
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Checked prices: ChatGPT: from Free $0; Go $8/mo; Plus $20/mo; Pro $100/mo (verified 2026-10-17)
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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