Small Business Big AI

You think you own your business. You log into the CRM, youexport the spreadsheet, you watch the follower count climb — and it feels like ownership. In this Coffee Table Conversation, Kim and Hal make the case that most of it is rented, and that AI just raised the stakes on the difference. It starts with a line Kim said to a friend that landed harder than she meant it to: you didn’t build a busines...

You bought the AI to get your life back. So why did it quietly book your weekend? There’s finally a number on it. The Glean Work AI Index (June 2026) found AI gives the average operator about 11 hours a week back — and then takes roughly 6.5 of them right back in supervision. Checking. Correcting. Re-prompting. Cleaning up. It even has a name now: botsitting. Kim calls it the six-hour tax. In this...

Every small business owner is asking the same question rightnow: “Which AI tool should I be using?” Kim Lewis Howard says it’s the wrong question. And she has a better one. In this episode, Kim and Hal make the case that the businesses winning in an AI economy are not the ones with the best tools. They are the ones who figured out what they have that AI cannot replicate for a competitor — and then...

What happens when your next customer never calls, never fills out the form, never reads your About page — becausetheir AI agent does it for them? In Episode 93, Kim Lewis Howard and Hal Howard close the Systemized or Squeezed series with the most forward-looking conversation of all four weeks. This is a Coffee Table Conversation— Kim and Hal thinking out loud at the edge of what they know, naming...

The businesses pulling ahead aren't bigger. They're leaner. Here's the blueprint. In Episode 92, Kim Lewis Howard and Hal Howard draw the line between reactive lean and designed lean — and showwhat a business actually looks like when AI is the operating system, not just a tool on the side of the desk. Kim names the four characteristics of a designed-lean business, shares a real consult...

Your best clients don’t know how you do it. They just know it works. That gap—between what clients experience and what it actually takes to deliver that experience—is where themost durable competitive advantages are being built right now. Not through bigger teams or faster hustle. Through invisible infrastructure. In Episode 91, Kim and Hal break down the three-layer architecture behind businesses...

The AI divide is quietly splitting small businesses in half — and most owners are on the wrong side without knowing it. There is a divide forming in small business — and it is not about who is using AI. It is about how. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard name the two tiers of AI adoption that are quietly splitting entrepreneurs apart: businesses that have bui...

What do the CEOs of Lowe's, YouTube, and IAC/Expedia all have in common? They listen — not politely, but strategically. In this Coffee Table Conversation, Kim and Hal break down how listening has quietly become the most powerful competitive advantage in the AI era. As small businesses invest in more AI tools than ever before (the average owner now runs five AI toolssimultaneously), the differe...

The distance between what you could do in year one and what you can do in year three is not a measure of how hard you worked. It's a measure of how well you designed. The series finale. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard close the IMPACT loop with the layer that changes not just what your business does — but what it becomes. Through the story of Elena, a...

Everything your system produces has your name on it. Checkis how you stand behind it. A Tuesday phone call. A gracious client. A citation that didn't exist. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard walk through the IMPACT layer nobody gets excited about — the one that feels like overhead, until it isn't. Through the story of Renata, a marketresearch consultant whos...

A $52,000 sale walked out of Hal's dealership because a four-minute follow-up got buried in Wednesday's chaos. Right now, the same thing is happening to thousands of small business owners. Not with trucks, but with leads of every kind. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard move from thinking systems to running systems: Activate, the third layer of the IM...

Stop trying to teach your team your taste. Build a system that has taste. Seven people on your team. Every one of them using AI. Productivity is up — but the business is starting to sound like seven different companies. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard name the quiet failure mode nobody warns you about: intelligence drift. Through the story of Sofia, a prem...

Most entrepreneurs think the secret to getting better results from AI is writing better prompts. But what if the real problem starts before the prompt is even written? In this episode of Small Business Big AI , Kim Lewis Howard and Hal Howard explain why so many business owners feeldisappointed by AI tools like ChatGPT—even when the answers seem technically correct. The problem isn’t the AI. And i...

Most small businesses are experimenting with AI tools—butvery few have turned them into systems that actually run the business. In this episode of Small Business Big AI , Kim Lewis Howard and Hal Howard explain why the companies winning with AI aren’t just using tools—they’re designing AI systems , including the idea of an AI Chief of Staff that prepares your day before you even open your laptop....

"Build a million-dollar business with one AI tool." The pitch is everywhere — and Kim and Hal aren't buying it. In this Coffee Table Conversation, they pull apart the one-person business model honestly: what actually works, what's marketing, and what it costs when you remove all the humans from the equation. From the emotional reality of entrepreneurship to deal-level pattern rec...

The question isn't whether AI is ready for your business; it's whether you're ready to stop being the engine. The Agentic Shift is here — and most small business owners are experiencing it as anxiety, not advantage. In this episode, Kim and Hal unpack the most important distinction of 2026: the difference between being the engine in your business (doing the work) versus being the engin...

You don't have a prompting problem. You have a design problem. Most small business owners are stuck at Level One — better prompts, faster outputs, same results. In this episode, Kim and Hal break down the AI Thinking Stack: a three-level framework that separates operators who use AI from operators who are built on it. From a standing-room-only Small Business Expo in Orlando to Kim's real-t...

MIT’s 2026 prediction is blunt: AI becomes invisible. It stops being a feature and starts being how work gets done. When that happens—when AI operates continuously in the background, executing business functions without waiting for you—it isn’t a tool anymore. It’s workforce. In the final episode of the Agent Layer Trilogy, Kim and Hal make the case for what that shift actually requires: not more...

The adoption gap is closing fast. 89% of small businesses now use AI in some capacity—and 78% report efficiency gains. So why does most of it feel like it’s not working? Because the competitive edge in 2026 isn’t about whether you use AI. It’s about whether you’ve built a system around it. In this episode, Kim and Hal follow two business owners—both named Sarah, same industry, same starting point—...

Agentic AI is no longer a future scenario. It’s the operational reality of 2026. The market is projected to hit $45 billion by2030, and Gartner predicts 40% of enterprise applications will have embedded agents by year’s end. But here’s the number that should stop every small business owner in their tracks: only 11% of agentic AI use cases made it to production last year. That’s not a learning curv...

The shift isn't learning AI—it's building a business where AI can actually contribute. Every founder eventually hits the "2 AM ceiling"—the realization that they’ve built a business that can’t runwithout their constant judgment. We often look to AI for freedom, but without a system, we just end up busier managing more outputs. This series finale moves beyond skills and into organ...

The most important AI skill isn't prompting—it's the sameskill you use with your best employee who doesn't read minds. You’ve seen the ads: "Master the perfect prompt for $497.” But prompting is just a surface-level fix for a much deeper leadership gap. In this episode, we pull back the curtain on why "clearer prompts" won't save you if you don't know how to mana...

AI was supposed to make work easier. For many experienced business owners, it’s doing the opposite. In this episode, Kim Lewis Howard and Hal Howard unpack a frustration they’re seeing everywhere—but almost no one isnaming clearly: why capable operators feel slower, less confident, and more mentally taxed when working with AI. This isn’t a tools problem. And it’s not a competence gap. It’s a leade...

📅 January 27 — Live on LinkedIn Join Kim and Hal live on LinkedIn at 2:00 PM EST as they’re joined by Rob Belfield and Jon Stevens to discuss why most businesses struggle to move from advice to implementation —and what an operating model built for this moment really looks like. 👉 Link to the live event: https://www.linkedin.com/events/thegreatdisplacement-asaferpath7419916211754524673/theater/  ...

Upcoming Event 📅 January 27 —Live on LinkedIn Kim and Hal go live with Rob Belfield and Jon Stevens to dig into the real questions operators are wrestling with right now—no panels, no polish, no platitudes. ---  This event is for you if you are: A displaced Big 4 / consulting professional A fractional COO, CFO, or senior operator A small business owner who needs real implementation help—not more...