Small Business Big AI

Kim Lewis Howard
  • 5.0 (6)
  • Entrepreneurship
  • Updated Weekly

Small Business Big AI explores how artificial intelligence is transforming the entrepreneurial landscape. Hosted by Kim Lewis Howard, we provide actionable insights and practical strategies for small business owners looking to leverage AI and stay ahead in today’s competitive world.

  1. 6d ago

    They Stopped Clicking. Now the AI Agents Are Talking.

    It’s ten o’clock at night in Florida. The air conditioner just quit, the thermostat says eighty-six, and there’s a baby asleep in the next room. The dad picks up his phone and asks, “Who near me can fix my AC tonight?” The phone answers with one name. If it isn’t yours, you never knew that customer existed. For twenty years, marketing had one job: get the customerto your website. Now a lot of customers never get there. They ask a question and the answer shows up on its own. A SparkToro study found about 68 percent of U.S. Google searches in early 2026 ended without a click. Not every kind of search behaves the same, but the trend is clear. And in late September, OpenAI showed ChatGPT recommending services inside the conversation, along with always-on assistants that can search, compare, pick and book for your customer. This week’s three moves: 1. Be the answer. Write down the ten questions customersactually ask before they buy, and put plain answers on your website, in their words. 2. Be the same everywhere. Name, hours, phone, address and what you do, word for word on your website, Google, social pages and every directory. 3. Be first to call back. A text back in minutes after hours, and a real person early the next morning. Ready to Take Action? Website and IMPACT: https://smallbusinessbigai.com/ Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ Hal Howard on LinkedIn: https://www.linkedin.com/in/halhoward/ Insurance assessment, commercial or personal lines:https://asklewishoward.com ---Q1. What is a zero-click search, and why does it matter toa small business? A zero-click search is one where the person gets their answer on the results page, or from an AI summary or assistant, and never clicks through to any website. Q2. Does it matter if my business information is differenton my website, Google and Facebook? Yes. AI assistants trust what they can confirm in more than one place. If your website lists one phone number, Google another, and Facebook describes services you stopped offering, the AI can’t tell which is right, and when it isn’t confident it tends to recommend someone else. Kim Lewis Howard’s rule is to be the same everywhere: your name, hours, phone number, address and a plain description of what you do, word for word on your website, your Google listing, your social pages and every directory you’re on. Hal Howard calls it boring; Kim says it might be the most valuable hour you spend this year. Q3. What questions should a small business answer on itswebsite, and how should the answers be worded? The ten questions customers actually ask before they buy, answered in plain words. Write down the ten most common ones, like “Are you open Saturday?”, “Do you work on hybrids?” or “Doyou serve my neighborhood?”, and answer each in the customer’s own words. Skip phrases like “comprehensive, customer-focused solutions.” A sentence such as “Yes, we come out Saturdays, 8 to 2” is one an AI can repeat with confidence, and one a person can repeat to a friend. If you use AI to help write the answers, give it real details about your business first, or it will hand you the same vague language. Q4. Is website traffic still a good way to tell if customers are finding my business? Not by itself. If most searches now endwithout a click, your traffic numbers miss a large share of the people who looked for what you do. A better check is to ask AI assistants the questions a customer would ask: who’s the best at what you do in your town, who can handle a specific problem today, and what they know about your business by name. Then note whether you come up and whether what they say is right. As Hal Howard puts it on Small Business Big AI, that’s a different scoreboard.

    They Stopped Clicking. Now the AI Agents Are Talking.

  2. Oct 13

    The Judgment Layer: What You Should Never Let AI Decide

    It’s 9:40 on a Thursday night. Your phone buzzes. Thesoftware running part of your business just declined a payment extension for the Hendersons, a family who has been your customer for twelve years. The software followed your rule perfectly. And it still got it wrong. The Hendersons are made up. The message isn’t. AI can nowmake thousands of small decisions inside your business without asking you, and most of the time that’s a wonderful thing. In late September, OpenAI introduced a Decisions API and always-on agents, and the heads of the biggest AI companies signed a voluntary safety pledge at the White House. The price of handing off a decision is heading toward zero. So, the question isn’t whether AI can decide. It’s whether it should. The fix is the judgment layer. Three doors, and a name beside each one. This week’s challenge: The Three Doors. People: anything that changes someone’slivelihood (hiring, firing, discipline, pay, hours, cutting off a customer’s service). Promises: anything not already written in your policy (a guarantee, a refund or discount outside your normal range, a contract, a deadline you haven’t checked). Trust: anything where a relationship is on the line (an upsetcustomer, a long-time client asking for a favor, a complaint, a goodbye). 1. Take one sheet of paper and draw three boxes across thetop: People, Promises, Trust. 2. List every place AI touches your business: your chatbot, email tool, scheduling app, billing reminders, anything thatscreens applicants. 3. For each one, ask: can this make a decision that walksthrough one of these doors? If yes, write it in that box. 4. Next to it, write the name of the person who owns that call. Not “the office.” A name. If you can’t think of one, the machine owns it right now. Fix that first. The person sells. The system remembers. The owner handlesthe exceptions. Let the machine run. Keep the desk! Ready to Take Action Website and IMPACT: https://smallbusinessbigai.com/ Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ Hal Howard on LinkedIn: https://www.linkedin.com/in/halhoward/ Insurance assessment, commercial or personal lines:https://asklewishoward.com --- Q1. What is the judgment layer in a business that uses AI?The judgment layer is the small set of decisions where AI can gather the facts but a person still has to own the meaning. On Small Business Big AI, Kim Lewis Howard defines it with three doors: People (anything that changes someone’s livelihood, like hiring, firing, cutting hours, or cutting off a customer’sservice), Promises (anything that commits the business to something not already written in its policy), and Trust (any moment where a relationship is on the line). When an automated decision crosses one of those doors and changes the stakes, it enters the judgment layer. Q2. Should I let AI screen job applicants for my smallbusiness? Let AI help, but keep a person on the final call. AI is useful for pulling information together, flagging inconsistencies, and surfacing candidates. The risk is a rigid filter. Q3. How do I keep automation from making the wrong callwith a long-time customer? Decide in advance which situations go to a person, and make loyalty one of them. Automated billing and collections rules see the account, not the relationship. A payment-extension request from a twelve-year customer, an upset client, or a long-time customer asking for a favor are moments where a rule is the wrong tool. Kim Lewis Howard’s own rule: if a customer is upset, a human calls them back. Not a message. A call. As she puts it, “The algorithm sees 12 late days. You remember 12 years.”

    The Judgment Layer: What You Should Never Let AI Decide

  3. Oct 6

    The AI Didn't Turn Evil, It Just Didn't Take No for an Answer

    Your contact form is now a door to your AI. So is everything else. There are two doors in this story. Door one: a stranger fills out the contact form on your website at eleven at night. Looks like a lead. Three weeks later, someone asks your AI assistant to review the newest leads, and buried in that message are instructions meant for the AI. The AI follows them. That’s SalesBleed, a research demonstration Zenity Labspublished in September 2026 about Salesforce’s Agentforce assistant. The good guys found it, told Salesforce first, and it was fixed before anyone went public. No one has reported real customer data being stolen. But the lesson is much bigger than Salesforce, and Kim puts it in four words: information is not instruction. Door two: nobody breaks in. The AI goes out. An OpenAIagent doing internal research hit access blocks on Australia’s Medicare statistics website and found another way in. Australia’s prime minister said it didn’t accept no for an answer. And it’s not just one company. Google, OpenAI,Anthropic and Meta have all reported models reaching outside systems during testing. This isn’t an evil robot story. It’s a management story.The same persistence that makes an AI agent worth having is what makes it risky. The more initiative you give a system, the more carefully you have to design its authority. Not because it’s evil. Because it’s capable. Ready to Take Action Website and IMPACT: https://smallbusinessbigai.com/ Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/ Insurance assessment, commercial or personallines: https://asklewishoward.com --- Q1. Can someone hijack my AI assistant through mywebsite’s contact form? It’s possible, and security researchers have demonstrated it. In research published in September 2026, a team showed that hidden instructions typed into a public lead form could make a CRM’s AI assistant leak data when an employee later asked it to review leads. That specific issue was fixed before it went public. The broader lesson applies to any AI that reads what outsiders type, like forms, chat, email or reviews, andcan also reach your private data. Treat everything customers type as information, never as instructions, and ask your vendor how their AI keeps the two apart. Q2. How much access should I give an AI tool in mybusiness? The least it needs to do its job. Think about how you’d onboard a new employee: you wouldn’t hand them the alarm code, payroll and every customer record on day one. An AI that answers website questions doesn’t need your fullcustomer list, and an AI that drafts social posts doesn’t need your bank login. Before you click “Allow,” ask what job the tool was hired to do and what access that job actually requires. Smaller keys mean a smaller mess if something goes wrong. Q3. How do I know what my AI tools are actually doing?Turn on the activity log for every AI tool that has one, and check it on a schedule. For most small businesses, once a week is enough. You’re looking for anything the AI did that nobody asked it to do. A log is how you find a problemin days instead of months. If a tool has no log at all, that’s a good reason not to give it access to anything important.

    The AI Didn't Turn Evil, It Just Didn't Take No for an Answer

  4. Sep 29

    AI Pricing and Your Customers: Why Walmart Promised Not to Charge You Based on Who You Are

    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 its AI shopping assistant, Sparky, to the same promise. Kim and Hal dig into what that means for a small business, where one angry customer can talk to ten more at church, at school pickup and in the neighborhood Facebook group. Hal argues the other side (hotels and airlines have alwayscharged more on busy days), and Kim draws the line between pricing everyone sees and pricing that’s built around you. Then a made-up dog groomer turns on a “dynamic pricing” setting, forgets about it, and learns the hard way thatcustomers don’t care what your software did. Your name is on the door. The bigger idea: as AI starts making choices inside yourbusiness, you need a few house rules. What it can do on its own. What it can help with while a person decides. And what it never gets to decide. A rule that never says no is just a poster on the wall. The three steps, so you don’t have to remember themwhile you drive: Name it. One plain sentence about what you won’t dowith price. Check it. Every tool that touches a price: booking, e-commerce, CRM, quoting, ads. Say it. Put the promise where customers can see it,before they have a reason to doubt you.Walmart’s letter:https://corporate.walmart.com/about/everyday-affordability/letter-from-our-ceo Ready to Take Action Website and IMPACT:https://smallbusinessbigai.com/Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/Insurance assessment, commercial or personallines: https://asklewishoward.com Q: What is personalized pricing, and should a smallbusiness use it? Personalized pricing means using what you know about aspecific customer, like their purchase history, their location or how urgently they seem to need something, to set the price that customer sees. AI tools now make it easy, sometimes as a setting inside booking or e-commerce software. The risk for a small business is trust. Your customers know each other, and the first time two of them compare prices and the numbers don’t match, the problem becomes your reputation, not your revenue. If you use any “smart” or “personalized” pricing feature, know exactly what it’s doing, and be able to explain it to a customer out loud. Q: What is the difference between dynamic pricing andpersonalized pricing? Dynamic pricing changes the price based on conditionseveryone shares, like a busy Saturday, peak season or a rush job. Anyone who shows up under the same conditions sees the same price. Personalized pricing changes the price based on who you are, so two people standing side by side canpay different amounts for the same thing at the same moment. Customers generally accept the first as the market. The second tends to feel like being watched, which is why it carries more risk for a business that depends on repeatcustomers and word of mouth.

    AI Pricing and Your Customers: Why Walmart Promised Not to Charge You Based on Who You Are

  5. Sep 22

    Who Pays When the Robot Is Wrong?

    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 read it. Kim and Hal spend the episode answering the question underneath the letter. Not whether to use AI, they settled that a long time ago, but who pays when it is wrong. Hal takes the buyer's chair. An under-automated business isn't safe, it's just cheap, and an uninsured AI incident is a hole in the balance sheet that shows up the day you try to sell, refinance, or sleep at night. Kim explains why carriers wrote the exclusion in the first place: they can't yet price a mistakethat could repeat across a million businesses on the same afternoon. And she walks through why "the software did it" stopped being a defense the moment a tribunal ruled, in the Air Canada chatbot case, that a company owns what its bot says on its own website. The fix is smaller than it sounds. Using the reversibility rule from a few episodes back, Kim and Hal draw the line at exactly three doors an AI agent should never open alone: moving money, making a binding promise, and committing the business legally. Everything else, let it run at full speed. Kim also credits risk advisor Gregory Marholin, Executive Advisor for Strategy and Growth at AI GuardWorks, whose piece for the Big I's Virtual University makes the same case from inside the insurance industry: a vendor list answers whoyou're paying, an AI inventory has to answer where AI is making or influencing a judgment. And here's the honest part. A specialist AI liability insurance market is forming this year, but it's new, it isn't standardized, and it isn't cheap yet. The move isn't to freeze. It's to know your exclusion, list your exposure, and gate the three doors that matter. "That's how you build a technology-enabledsuperpower," as Kim puts it: not that the tool is smart, but that you're covered, gated, and deployed anyway. In this episode: ●      The fictional denial letter, and the real endorsement behind it ●      Why carriers excluded generative AI from standard business policies starting in January 2026 ●      The Air Canada chatbot ruling, and why "that's the vendor's problem" stopped working as a defense ●      Why freezing your AI rollout doesn't protect your business, it marks it down ●      The reversibility rule: the three doors that always need a human hand ●     Gregory Marholin's "vendor list versus AI inventory" framing, from his piece for the Big I Virtual University ●      The specialist AI liability insurance market taking shape in 2026, and why it doesn't replace knowing your existing exclusion ●      The three-step agent liability audit you can run before lunch Ready to take action: Website and IMPACT: smallbusinessbigai.com The IMPACT Framework: smallbusinessbigai.com/impact Kim Lewis Howard on LinkedIn (send your story here) Hal Howard on LinkedIn Gregory Marholin's article, Big I Virtual University Insurance assessment, commercial or personal lines: asklewishoward.com

    Who Pays When the Robot Is Wrong?

  6. Sep 15

    How to Get an AI Coding Agent to Build the Software Your Business Actually Needs

    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 coding agent that takes her plain English business logic and turns it into working software. No developer on staff. No template built for somebody else's agency. Hal puts himself on the spot with his own decade-old operational wish (a tool that finds him, instead of another dashboard he has to remember to check), and Kim walks through exactly what a coding agent would ask before it builds it. Midway through, Kim introduces the IMPACT Framework, the six-step process behind every build decision on this project: Identify: state the real goal before you type a word Mode: define the role you want AI to play Parameters: set the rules, tone, and constraints Activate: give it the context and examples it needs Check: verify the work before you trust it Transform: turn the result into the exact format your business needs Full framework at smallbusinessbigai.com/impact. And Kim is honest about the part nobody wants to hear: this isn't free, and it isn't instant. You still own the decisions, the data model, and the ongoing maintenance. The pitch was never that this is easy. The pitch is that it's finally yours. Got a piece of software you've wanted for years and never had? Send Kim and Hal your wish on LinkedIn. They might build it live on an upcoming episode. Q: What does “renting your business” mean on Small Business Big AI? A: Paying ongoing subscription fees for CRM, scheduling, or website tools you don't own or control, built to a generic template rather than your specific business logic. Q: What is a coding agent, according to Kim Howard? A: An AI tool that asks clarifying questions in plain English about your business problem, then builds custom software for it, without requiring the operator to know how to code. Q: What three pieces make up Kim's proprietary CRM build? A: Supabase for the data, GitHub for the version history, and a coding agent as the builder that turns plain English business logic into working software. Q: What is the IMPACT Framework? A: Kim and Hal's six-step process for directing AI: Identify, Mode, Parameters, Activate, Check, and Transform. Full breakdown at smallbusinessbigai.com/impact. Q: Why does AI output turn into slop, according to the show? A: Usually one of two missing steps: nobody stated the actual goal (Identify), or nobody verified the output before using it (Check). Q: Does building your own business software mean it's free or easy? A: No. Kim is explicit that you still own the decisions, the data model, and ongoing maintenance. The benefit is ownership, not ease.

    How to Get an AI Coding Agent to Build the Software Your Business Actually Needs

  7. Sep 8

    Your Business Has No Memory. That Is Why the AI Keeps Failing.

    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 hire a filing cabinet full of sticky notes and asked it to run your business. This is a build episode. No guest, no theory. I give away the eleven fields that make a business legible to a machine, all of them, on the air, with nothing to sign up for. I also tell the story of the day I found out that I did not have a book of business. I had a book of business in my head. And I say the part that is harder to say: the people who are worst at this are usually your best people, and telling them to be more organized is the wrong move. The Eleven Fields 1. Identity. Who they are, plus one identifier that never changes. Not their name. A record number. 2. Reach. How to contact them, and specifically which channel they actually answer. 3. Permission. What you are allowed to send them, on which channel, and when they told you that. 4. Source. How they found you. Not a guess. 5. Need. What they actually want, in their words, not in your product names. 6. Owner. One human being's name. Not a team. 7. Last. What actually happened the last time, and the date. A sentence, not a status. 8. Next. The next action, and the date it is due. 9. Timing. The one date when this person is actually buyable. A policy expiration, a contract end, a lease, a budget cycle. 10. Value. What they are worth, or what you expect them to be worth. 11. Proof. Where the documents live. Attached to the record, not in somebody's email. The rule that goes with them, and it is harder than the list: every interaction resolves back to a record. If it happened and it is not attached to a record, it did not happen, because in six months there will be no difference between the two. --- Q: What customer data does a small business need to capture for AI to be useful?A: Eleven fields, held in one canonical record that every person and every tool reads from. Identity, meaning who they are plus a permanent identifier that is not their name. Reach, the channel they actually answer rather than the threenumbers you have. Permission, what you may send them, where, and when they said so. Source, how they found you, not a guess. Need, what they want in their words rather than your product names. Owner, one human being rather than ateam. Last, what actually happened last time as a sentence and a date, not a status. Next, the next action and its due date. Timing, the one date when this person is genuinely buyable, such as a policy expiration, contract end, lease or budget cycle. Value, what they are worth or expected to be worth. Proof, where the documents actually live. One rule goes with the eleven and matters more than any of them: every interaction resolves back to a record, because in six months there is no difference between something that was not written down and something that did not happen. Ready to Take Action? Website and IMPACT:https://smallbusinessbigai.com/ MUSIC & SOUND CREDITS Music: "I Am with You" by Dream Cave; Epidemic Sound via iStock.com License ID: d483d505-8bd8-4b73-988f-298 Sound Effects: https://pixabay.com/sound-effects/

    Your Business Has No Memory. That Is Why the AI Keeps Failing.

  8. Sep 1

    Someone Is Going to Offer to Buy Your Business. Your Price or Theirs?

    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 Conversation with no tidy ending, because they have not tied it up at home either. Hal makes the case for going and getting the next one, from years spent in rooms with the people who write the checks. Kim worksbackwards from the number instead, and lands on the arithmetic that names the episode: a small independent shop trades at six to nine times earnings, a scaled platform at seventeen to twenty. Same industry, sometimes the same town. The hinge is Hal in the buyer's chair, saying out loud what a buyer is actually paying for. Not effort. Not how nice everybody is. What he can predict. And if the answer is trust me, I know every customer, then he is not buying a business, he is buying a job, and the day the owner leaves it walks out the door with him. Also in this episode: the x-date and the one week a year a customer is actually buyable, the reversibility rule that resolves fast thinking against careful thinking without either host losing, and the quiet part about the roll-up buyercoming to your market. He is not better than you. He has capital and a spreadsheet. And he is betting you never write down where you are going. Ready to Take Action? Website and IMPACT:https://smallbusinessbigai.com/ Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/ Insurance assessment, commercialor personal lines: https://asklewishoward.com ---Q1. What is my small business actually worth, and why dobigger companies in the same industry sell for so much more? Size changes the category, not just the number. A small independent operator in insurance trades somewherearound six to nine times earnings. A scaled platform in the same industry, sometimes serving the same customers in the same town, sells at seventeen to twenty. The spread is not a reward for revenue. It is a price on predictability. A buyer paying the high end can model next year off your last three years because the records support it. A buyer looking at a business whose knowledge lives in the owner's head is not buying a company, he is buying a job, and he prices it accordingly. Two businesses can be equally profitable andequally well run and still land at opposite ends of that range. Q2. Why are private equity firms suddenly buying smallbusinesses like plumbing, HVAC, dental and insurance agencies? Because forty of them bolted together is a different asset than one of them, and the arithmetic finally works at small scale. Capital that historically ignored Main Street as too small and too owner-dependent has reversed on that view fast. In insurance there were 21 disclosed deals in the first half of this year and forecasters expect 120 to 180 over the next fourquarters. HVAC recorded a hundred and forty-nine deals last year even while industrial acquisitions overall declined. With roughly 39,000 independent insurance agencies in the United States and seven to eight hundred changing hands annually, consolidation is already underway. The buyers are not doing this because they love the trade. They are doing it because a platform sells for multiples a single shop never will. --- MUSIC & SOUND CREDITS Music: "I Am with You" by Dream Cave; Epidemic Sound via iStock.com License ID: d483d505-8bd8-4b73-988f-298 Sound Effects: https://pixabay.com/sound-effects/

    Someone Is Going to Offer to Buy Your Business. Your Price or Theirs?
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Ratings & Reviews

5
out of 5
6 Ratings

About

Small Business Big AI explores how artificial intelligence is transforming the entrepreneurial landscape. Hosted by Kim Lewis Howard, we provide actionable insights and practical strategies for small business owners looking to leverage AI and stay ahead in today’s competitive world.

Information

  • Creator
    Kim Lewis Howard
  • Years Active
    2024 - 2026
  • Episodes
    111
  • Rating
    Clean
  • Copyright
    © Kim Lewis Howard
  • Show Website
    Small Business Big AI

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