HeyJaredSmall Business Big AI
Small Business Big AI explores how artificial intelligence is transforming the entrepreneurial landscape.
- Indexed episodes, last 90 days
- 13
- Latest publication
- Sep 29, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
AI Pricing and Your Customers: Why Walmart Promised Not to Charge You Based on Who You Are (opens the original)
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Same table. Same menu. Same chicken parm. Hers is twenty-two dollars. Yours is twenty-six, because the software knows you’re a regular and figures you’ll pay it. The restaurant is made up. The technology that could run it that way is not. On September 25, 2026, Walmart CEO John Furner put oneline in a letter to customers: “We price the product, not the person.” Walmart says it won’t set prices based on who you are, your income, your shopping history or how badly you need something, and it holds
Who Pays When the Robot Is Wrong? (opens the original)
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Kim opens this episode holding a letter that has not been written yet. It is a claim denial addressed to a small business owner whose AI tool made a promise the business could not keep, citing the generative AI exclusion that quietly landed inside most business insurance policies in the country this January. Nobody has actually received that letter. But the exclusion is real, and almost nobody who turned on an AI receptionist, a quoting tool, or a two-in-the-morning chat window this year has rea
How to Get an AI Coding Agent to Build the Software Your Business Actually Needs (opens the original)
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It's the exact two-year anniversary of Small Business Big AI , and Kim and Hal are finally answering a promise from a year ago. In Episode 96, they told you that you were renting your business: your CRM, your scheduling tool, your website, all of it built for an imaginary average company, none of it actually yours. This week, they hand you the blueprint to buy it back. Kim is building Lewis Howard Insurance Group's own proprietary CRM live, in real time, using nothing but Supabase, GitHub, and a
Your Business Has No Memory. That Is Why the AI Keeps Failing. (opens the original)
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A friend spent four months and real money putting AI into her business. Good tools, the expensive ones. Last Tuesday she called to say it was confidently wrong about everything and she was about to rip the whole thing out. So I asked her one question. When your AI says this customer, where does it look? Long pause. That is the whole problem, and it has nothing to do with the model she picked. Your AI is not failing because it is not smart enough. It is failing because you handed a brilliant new
Someone Is Going to Offer to Buy Your Business. Your Price or Theirs? (opens the original)
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Kim wrote a press release announcing the sale of Lewis Howard Insurance Group for eighteen times earnings. It has not happened. She wrote it because until you write it, somebody else writes it for you, and when they write it, they pick the number. Then Hal read his. One sentence, and it says something else entirely: the agency has acquired its eleventh location. Hers has a multiple in it. His has a count. Neither of them heard the difference until it was read out loud. This one is a Coffee Table
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