Small Business Big AI

Kim Lewis Howard
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  • 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. 23H AGO

    How to Build a Business That Runs Without You (Using AI)

    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 from treating AI as a tool you "use" to a teammate that "owns" afunction. What’s Inside: The Founder Bottleneck: Why whatever lives only in your head is exactly where your growth goes to die.Tool vs. Teammate Mindset: The shift from reactive, transactional use to embedded, operational leverage.The 3 Requirements of the Operational Shift:Defining scope, establishing persistent context (institutional knowledge), and feedback integration.The Friction Map: How to use the moments where AI misses the mark as a GPS to find the "duct tape andintuition" holding your business back. This Week’s Challenge: Commit to one recurring, high-impact task. Document the Context, Criteria, and Checkpoints, and then—crucially—decide where that documentation lives so it becomes infrastructure, not just a file in a folder. Ready to Take Action? Subscribe to Small Business Big AI on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.Join the AI Insiders Community for Exclusive Tips & Resources → ⁠Request to Join our Private Community⁠Ask us about the IMPACT Framework course—astrategic way to communicate effectively with the AI → ⁠Email Howard & Howard Holdings, Inc.⁠Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed for business owners → ⁠Email Howard & Howard Holdings, Inc.⁠Have a question or an AI success story? DM uson ⁠LinkedIn ⁠or ⁠Facebook⁠! --- Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    22 min

  2. FEB 10

    The $497 Prompting Lie (And the Skill You Actually Need)

    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 delegated intelligence, and delegated intelligence requires management, not just a blinking cursor. What’s Inside: The Translation Layer Problem: Why builders think infeatures while operators think in outcomes—and why you must build the bridgebetween them.The Literal Employee: Why AI is the most demandingdelegation partner you’ll ever have because it cannot fill in gaps with intuition.The 3 Components of Real Delegation: A breakdown of Context, Criteria, and Checkpoints to ensure you never get a "confident wrong answer" again.Asset Building: How a 30-minute voice documentationexercise can become a permanent business asset.This Week’s Challenge: Pick one recurring task that always comes back "not quite right." Before you delegate it again,document the specific context, the red lines (what you would reject), and the definition of "done." Stop wrestling with AI and start leading it. Ready to Take Action? Subscribe to Small Business Big AI on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.Join the AI Insiders Community for Exclusive Tips & Resources → Request to Join our Private CommunityAsk us about the IMPACT Framework course—a strategic way to communicate effectively with the AI → Email Howard & Howard Holdings, Inc.Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed for business owners → Email Howard & Howard Holdings, Inc.Have a question or an AI success story? DM us onLinkedIn or Facebook! --- Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    24 min

  3. FEB 3

    Why AI Feels Harder Than It Should

    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. What’s Actually Going On Most AI tools are marketed like software upgrades—faster,cheaper, smarter. But AI doesn’t behave like software. It behaves more like delegated intelligence. And intelligence requires direction, standards, and judgment. When those aren’t explicit, friction shows up fast. In this conversation, Kim and Hal explain: Why “fine” AI output is more dangerous than bad outputHow AI exposes fuzzy goals, hidden assumptions,and unspoken standardsWhy prompting guides don’t solve the real problemThe difference between asking AI for work and managing itWhy frustration with AI is often a signal of leadership growth—not failureThey also ground the discussion in real operator experience, including a live event where “the tech worked”—but failed the business in real time. This Episode Is for You If: You’ve tried AI and thought, “This took longer than doing it myself.”You know what “good” looks like—but AI keeps missing the markYou feel pressure to “keep up” with AI success stories that don’t match your realityYou’re tired of being told to “just write better prompts”This Episode Is Not About: AI hacks, shortcuts, or shiny toolsPrompt formulas without contextHustle, hype, or performance theaterThis is Part One of a three-part series, The Leadership Nobody Trained You For. In Part Two, Kim and Hal break down the specific leadership skill that turns AI from frustrating to genuinely useful—in real business conditions. Ready to Take Action? Subscribe to Small Business Big AI on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.Join the AI Insiders Community for Exclusive Tips & Resources → Request to Join our Private CommunityAsk us about the IMPACT Framework course—a strategic way to communicate effectively with the AI → Email Howard & Howard Holdings, Inc.Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed for business owners → Email Howard & Howard Holdings, Inc.Have a question or an AI success story? DM us on LinkedIn or Facebook!---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    22 min

  4. JAN 27

    Stop Experimenting, Start Operating: The AI Shift That Actually Works

    📅 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 displaced Big 4 / consulting professionalA fractional COO, CFO, or senior operatorA small business owner who needs real implementation help—not more decks For the re-play just say: “Tell me more about the BMS Licensee Model.” ✦ DM Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ ✦ DM Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/ ---  Why do most AI projects stall—even after promisingdemos and pilots?In this episode of Small Business Big AI, hosts Kim Lewis Howard and Hal Howard unpack the real reason most businesses fail to get value from AI—and why the problem isn’t the technology. Drawing on recent research from MIT, real operator conversations, and Kim’s lived experience building a new agency under real constraints, this episode exposes the critical gap between experimenting with AI and operating with it. If you’ve tried AI tools, felt optimistic, and then watched them quietly fade into the background, this episode will help you understand why—and what to do differently. What You’ll Learn in This Episode Why 95% of AI pilots fail to scale into measurable business value—and what that statistic actually meansThe difference between using AI and having AI run part of your businessWhy experimenting with AI feels productive but rarely creates leverageHow small businesses get left out of enterprise-led AI narratives (and why that matters)The three shifts businesses make when they successfully move from AI pilots to operationsHow to evaluate AI success using operational metrics, not adoption metricsA simple 15-minute exercise to identify why your AI tools aren’t stickingThe Core Insight Most AI projects don’t fail because the tools are bad.They fail because no one builds the bridge from “this is interesting” to “this is how we operate now.” AI becomes valuable only when it is embedded into workflows, measured by outcomes, and trusted to run without constant human intervention. The 3 Shifts Businesses that Win with AI Make 1.   Workflow before tool - They define what the process needs to become before choosing technology. 2.  Bridge, not just pilot - Pilots prove possibility. Operations prove reliability—without babysitting. 3.  Measure operation, not adoption - The right question isn’t “Do we use AI?” It’s “What percentage of this process does AI handle end-to-end?”  About the Show Small Business Big AI is a strategist-led podcast for operators who want to make better business decisions in an AI-shaped world.No hype. No tool worship. Just clear thinking about how real businesses actually run. --- Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    24 min

  5. JAN 20

    The Cost of Waiting: When Small Decisions Compound

    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 professionalA fractional COO, CFO, or senior operatorA small business owner who needs real implementation help—not more decksJust say: “Tell me more about the BMS Licensee Model.” ✦ DM Kim Lewis Howard on LinkedIn: https://www.linkedin.com/in/kim-lewis-howard/ ✦ DM Hal Howard on LinkedIn: https://www.linkedin.com/in/halhoward/   The Cost of Waiting: When Small Decisions Compound Most small business owners don’t fail because of one baddecision. They stall because of hundreds of reasonable delays. In this episode of Small Business Big AI, Kim Lewis Howard and Hal Howard break down the hidden cost of waiting—and why “fine” is one of the most dangerous signals in business. This is not an episode about hustling faster or chasing tools. It’s about how small decisions, postponed again and again, quietly compound into lost margin, lost position, and fewer options down the road. If you’ve ever told yourself “I’ll get to that next quarter”—this conversation is for you.   What You’ll Learn in This Episode Why waiting feels safe—and why it’s rarely neutralHow small, postponed decisions quietly compoundinto strategic driftThe difference between strategic patience and comfortable avoidanceWhy decision velocity often matters more than decision sizeHow one two-hour decision created $36,000 in annual savingsWhat operators miss when “everything is fine”The real human tension behind automation, efficiency, and AI-driven changeThis episode is grounded in real operator experience—fromrunning automobile dealerships and insurance agencies to making high-stakes decisions with real people on the line. The Core Idea Most operators think risk comes from acting too fast. In reality, the bigger risk often comes from waiting too long. Waiting delays learning. Waiting reinforces fragile systems. Waiting compounds drift. By the time clarity arrives, the math has already changed. Who This Episode Is For Small business owners who feel busy, capable, and slightly uneasyOperators running “healthy” businesses that haven’t broken—but haven’t moved eitherLeaders navigating AI, automation, or operational change without clear answersAnyone who senses they’re postponing somethingimportant—and knows it has a costWho This Episode Is Not For Tool chasers looking for quick AI hacksFounders who want certainty before making anymoveAnyone expecting hype, shortcuts, or motivational talk  About Small Business Big AI Small Business Big AI is a strategist-led podcast for operators who want to make better business decisions in an AI-shaped world. This isn’t a show about tools. It’s about how real businesses actually work—when time, money, people, and risk are real. Each episode is designed to help you think more clearly, decide more intentionally, and build an edge thatcompounds. --- Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    31 min

  6. JAN 13

    The Permission Trap: Why Waiting Is the Most Expensive Decision You’ll Make

    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 — especially in an era reshaped by artificial intelligence and rapid technological change. This week, we also weave in takeaways from the All-Inpodcast’s CES 2026 discussion on how AI is set to dwarf every tech revolution before it — transforming not just robots and gadgets, but how leaders accelerate decisions and reshape organizations in real time. (Apple Podcasts) What You’ll Learn in This Episode ✔ The Permission Trap defined:Learn the three versions that keep founders stuck — waiting for gatekeepers, waiting for markets to “settle,” and waiting for personal readiness. ✔ The real cost of waiting:It’s not just time — it’s position, momentum, and opportunity in a hyper-accelerated business landscape. ✔ Inside CES 2026 insights:We connect macro tech trends from the All-In podcast — where thought leaders argued that AI’s impact will eclipse past breakthroughs — to the micro reality of your business decisions. ✔ A real-world story that hits home:Hear how hesitation cost a logistics leader his competitive edge, even when the right tool was in front of him all along. ✔ The Operator Moment:Kim shares her personal journey with lease rejections, mindset shifts, and why she’s moving forward without permission. ✔ Weekly challenge:Identify the one decision you’ve been waiting on — then flip the frame and ask what you’re really waiting for. Join Us Live Save the date: January 27th — Kim and Hal are hosting a LinkedIn Live event to pull back the curtain on what they’vebeen building and answer audience questions live. This is for you if you are: A displaced Big 4 / consulting professionalA fractional COO, CFO, or senior operatorA small business owner who needs realimplementation help—not more decksJust say: “Tell me more about the BMS Licensee Model.” ✦ DM Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ ✦ DM Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/ ---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    25 min

  7. JAN 6

    The Middle Is Gone - Why AI Rewards Judgment, Not Hustle in 2026

    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 need to own right now. You'll hear Becky's real-time journey from displaced Big 4 consultant to solo operator with leverage—and why she rebuilt her entire client system in a weekend (while battling massive imposter syndrome). If you're grinding harder but getting less traction, thisepisode will give you language for what's happening—and a clear path forward. IN THIS EPISODE The Diagnosis: Why the middle disappeared and what that means for your identity (3:20) The Structural Break: How 2025 collapsed the old business model—and why "working harder" won't save you (5:30) Two Founders, Two Different Games: The compound effect of decision speed and why learning beats planning (8:10) The AI Orchestrator Role: What's actually left for humans (and why "inspiration without execution" is just expensiveprocrastination) (11:45) Becky's Transformation: How a displaced consultant rebuilt her practice in a weekend—and why nobody believes her (1:45) The Fork in the Road: The choice you're facing right now and what happens if you wait until Q2 (14:00) The Small Step Challenge: Two questions you need to answer in under 60 seconds (16:30) KEY TAKEAWAYS ✅ AI handles the middle. Humans own the edges. Judgment on the front end. Decisiveness on the back end. Everything else? Automated. ✅ Being busy isn't a flex anymore. It's a warning. If you're grinding on tasks AI can handle in 90 seconds, you're not being thorough—you're being slow. ✅ The future doesn't reward effort. It rewards decisiveness. Strategy is now a commodity. Execution atspeed is the premium. ✅ Waiting isn't prudent. It's a liability. The gap between those who moved and those who waited? It's widening. And by Q2, they'll be unreachable. ✅ Your technology-enabled superpower: The ability to do what used to take a team—by yourself—in a weekend. TAKE ACTION Join Our LinkedIn Live for the Month of January We're walking through the exact framework Becky used to rebuild her client system in a weekend. Not theory—actual deployment. The templates. The prompts. The decision trees. If you're realizing you've been standing in the middle, this is for you. Just say: “Tell me more about the BMS Licensee Model.” ✦ DM Kim Lewis Howard on LinkedIn: https://www.linkedin.com/in/kim-lewis-howard/ ✦ DM Hal Howard on LinkedIn: https://www.linkedin.com/in/halhoward/ ---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    26 min

  8. 12/30/2025

    The Great Redistribution: What 2025 Took Away (And What 2026 Is Giving You)

    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 something far more interesting underneath: A redistribution of talent, leverage, and execution power.   What You’ll Learn in This Episode Why the 2025 layoffs weren’t just a “cycle,” but a structural breakHow the traditional handshake between skill, title, and value quietly collapsedWhy small business owners don’t need more advice—they need executionHow AI accelerated the shift without being the cause of itWhy Q1 2026 is a narrow but powerful window (and why it closes quietly)What “fractional” really means now—and why it’sevolving fastHow high-caliber operators are repositioning without starting from scratchThe difference between being aggressive and being on time This episode is especially relevant if you are: A displaced Big 4 or consulting professional navigating what’s nextA fractional COO, CFO, or senior operator rethinking how you package your valueA small business owner stuck with complexity butunable to buy real implementationAn operator who wants leverage without bloatedoverheadAnyone trying to build a technology-enabledsuperpower in 2026  Key Insight from the Episode This moment isn’t about tools. It’s about ownership. The market is shifting away from titles, prestige, andpermission—and toward people who can take responsibility for outcomes. Those who move early don’t just participate in theredistribution.They get to set the terms. The rest inherit them. The Window Is Open (But Not Forever) We’re hosting a live LinkedIn event where we break down the full BMS Licensee Model—the exact framework Becky uses to build her fractional practice without starting from scratch. This is not freelancing.This is not gig work.This is precision execution, backed by systems, positioning, and leverage. This is for you if you are: A displaced Big 4 / consulting professionalA fractional COO, CFO, or senior operatorA small business owner who needs real implementation help—not more decksJust say: “Tell me more about the BMS Licensee Model.” ✦ DM Kim Lewis Howard on LinkedIn:https://www.linkedin.com/in/kim-lewis-howard/ ✦ DM Hal Howard on LinkedIn:https://www.linkedin.com/in/halhoward/ --- Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com Sound Effects: https://pixabay.com/sound-effects/

    26 min
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Ratings & Reviews

5
out of 5
4 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
    76
  • Rating
    Clean
  • Copyright
    © Kim Lewis Howard
  • Show Website
    Small Business Big AI