Small Business Big AI

Small Business Big AI

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.

Episodes

April 7, 2026 25 mins

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.

 

The Big Idea

Most businesses bought AI ...

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"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 recognition, this episode explores why...

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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 engineer (designing how the work gets don...

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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-time AAA agency build as an AI-native...

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March 10, 2026 33 mins

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 tools, but a fundamentally different...

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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—through 14 months of AI implementati...

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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 curve. That’s a 90% failure rate.

In thi...

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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 organizational design. It’s time to move ...

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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 manage. AI isn't just software; it is...

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February 3, 2026 21 mins

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 leadership shift no one trained you for.

Wh...

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📅 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/

 

This is for you if you are:

  • A displa...
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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 decks

Just say:

“Tell me more about...

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In this episode of Small Business Big AI, Kim and Hal tackle the invisible force holding small business owners back: thePermission Trap — the tendency to wait for someone else’s approval, clarity, or “perfect timing” before moving forward. With personal stories, expert insight, and strategic perspective, Kim dismantles the myth that patience equals wisdom and shows why decision speed is now the realcompetitive edge in business — es...

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It's 2026. The middle is gone. And if you're still standing there, you're about to get crushed.

This is the uncomfortable truth most business owners don't want to hear: AI didn't make business harder—it exposed just how much of "work" really never mattered in the first place.

In this first episode of the new year, Kim and Hal breakdown why 2025 felt so disorienting, what the "structural break" actually means, and the two edges you ne...

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In this New Year’s Eve episode of Small Business Big AI, Kim Lewis Howard and Hal Howard break down the real storybehind the 2025 layoffs—and why 2026 is quietly creating one of the biggest opportunities we’ve seen in years.

This isn’t a tech hype episode. It’s a market shift episode.

In 2025, high-skill talent was displaced at the same timesmall business owners hit an execution wall. What looks like chaos on the surface is actually ...

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What if losing your Big 4 job wasn’t the end of your career… but the moment you finally took control of it?

In this episode, we follow Becky, a former Big 4 consultant who went from 60-hour weeks and partner politics to running a $360K fractional executive practice—solo.

No team.

No burnout.

No Big 4 badge.

Just AI-powered leverage, smart workflows, and judgment that machines can’t replace.

This is Part 3 of The Great Displacement series...

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The $25,000 Binder That Changed Nothing

It's 11 PM on a Tuesday. Mike sits alone in his convertedstorage room office, staring at a leather-bound binder with gold embossed lettering: "Five-Year Strategic Growth Plan." He paid $25,000 for this plan. Spent two months in planning sessions. Got a 47-page document with charts, timelines, financial projections—everything.

And two years later? Not a single initiative has beenim...

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The consulting world is experiencing a seismic shift, andthousands of Big 4 professionals are being quietly swept into what Kim and Hal call The Great Displacement. In this episode, we break down the real economic and AI-driven forces behind mass layoffs at Deloitte, PwC, KPMG, andEY, and why this moment is a once-in-a-generation turning point for displaced consultants. Through the story of “Becky” we explore the identity crisis, b...

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Is your small business ready for AI—or are you aboutto scale chaos?

In this episode, Kim and Hal break down the AI Audit—astrategic 3-question framework that every legacy business must ask before implementing automation, AI tools, or tech upgrades.

These aren't fluff questions. They’re the hard ones. The ones that expose operational gaps, team bottlenecks, and silent friction that's eroding trust with your customers and emplo...

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I built an employee yesterday. In 45 seconds. For free.

It's scanning commercial real estate in Florida right now. It knows zoning laws, traffic patterns, and lease rates better than any broker I've hired. And I didn't write a single line of code.

For 15 years, we've been sold the Virtual Assistant dream: "Hire offshore labor for $5/hour. Hand over your inbox. Go sit on a beach."

But you didn't buy freedo...

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