Your team is using AI right now—and you probably have no idea.
From Canva to ChatGPT to Zapier, small business employees are quietly automating and creating with AI tools that were never approved, tracked, or reviewed.
In this episode, Kim and Hal shine a light on Shadow AI—the silent wave of innovation happening behind your back—and why ignoring it is costing you time, trust, and money.
Drawing insights from AI strategist Kristina Agustin (Southern Sky AI) and lessons from the 2025 Fort Lauderdale International Boat Show, they break down what every small business owner needs to know about compliance, leadership, and risk in the AI era.
You’ll discover how to:
✅ Spot hidden AI tools in your business (and stop data leaks before they start)
✅ Write a “good enough” AI policy in under an hour
✅ Lead innovation without killing creativity
Because if you’re not leading AI adoption in your company—you’re being led by it.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; Epidemic Sound via iStock.com
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#SmallBusinessBigAI #ShadowAI #AILeadership #AIPolicy #BusinessInnovation #TechSuperpower #FLIBS2025
Forty-seven days. That’s how long one small business owner waited to get paid for work she’d already delivered.
In this final chapter of AI Meets Humanity, Kim and Hal pull back the curtain on what they call “The Trust Machine” — a simple, zero-code system that turns compliance into confidence and contracts into cash flow.
Through real-world examples, sharp strategist banter, andlaugh-out-loud moments (yes, Hal still fears blockchain), this episode shows how AI can make trust automatic instead of assumed.
You’ll discover:
If you’ve ever waited weeks for payment, juggled clientfollow-ups, or lost sleep over “pending approval,” this episode is your blueprint for peace of mind.
Because in the AI era, trust isn’t a handshake — it’s a system.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
#SmallBusinessBigAI #AIforBusiness #AutomatedTrust #Compliance #Blockchain #SmartContracts #ZeroCodeAI
Your lead technician just took on 47% more work. Your designer stopped showing up to video calls. Your best customer sent an angry email at 11 PM—not about the service but about feeling invisible. What if these weren't separate problems, but the same signal?
In this episode, Kim and Hal explore how empathy has become your most advanced operating system in the age of AI. Spoiler alert: it's not soft. It's your most profitable competitive advantage. Featuring real business owners—a solopreneur, a regional catering leader, and a plumbing crewmanager—we unpack the Three Layers of AI-Driven Empathy and the Five Ds Framework: a practical system for detecting, discussing, designing, documenting, and developing empathetic leadership at any scale.
By the end, you'll walk away with proof that small steps lead to big changes.
KEY TAKEAWAYS
FRAMEWORKS & TOOLS MENTIONED
The Three Layers of AI-Driven Empathy
1. Insight Layer — What AI surfaces (patterns in tone, timing, workload)
2. Intention Layer — How you interpret it (context + curiosity before judgment)
3. Integration Layer — How you measure outcomes (retention, satisfaction, referrals)
The Five Ds Framework: Feedback Loops of Care
1. Detect — Use AI/data to surface signals you'd miss
2. Discuss — 15-minute one-on-ones with one real question
3. Design — Customized interventions based on what you learned
4. Document — Track patterns over time to see what works
5. Develop — Celebrate wins and spread the culture
KEY STATISTICS & RESEARCH
RESOURCES & FURTHER LEARNING
Mentioned In This Episode
Related Concepts
Recommended Reading/Listening
Ready to Take Action?
---Music Credit: “I Am with You” by Dream Cave; Epidemic Sound via iStock.com
This week, we’re diving into what AI can’t automate — authentic human connection.
When an unexpected “Pitch incoming 😎” message caught Kim’s attention, it sparked a bigger conversation: Why do some automated messages make us roll our eyes, while others make us reply?
Join Kim and Hal as they break down:
You’ll learn how to design your AI systems to sound morelike you, keep your customers’ trust intact, and build automation that scales connection, not just communication.
Because in the end, authenticity isn’t soft — it’s strategic.
You’ll Learn:
The H.E.A.R.T. Method (Quick Reference):
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Small business owners are drowning in AI subscriptions—and most of them are wasting money, time, and customer trust. In this episode of Small Business Big AI, Kim and Hal wrap up their trilogy on AI Agents & The Future of Small Business with a blunt truth: AI tools without strategy are liabilities, not assets.
You’ll learn how to stop chasing shiny objects and instead build systems that boost ROI, protect compliance, and turn AI into your business copilot. If you’ve been wondering how to cut through AI hype and actually get results, this episode delivers the clarity you need right now.
What You’ll Learn
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Shiny apps are everywhere. But small businesses don’t need more noise—they need results.
In Part 2 of our 3-part series, AI That Actually Works for Small Business, Kim and Hal take you inside the new business model playbook:
Kim shares her own in-progress story of opening a new insurance agency in the AI era, weaving in lessons from blockchain at the University of Oxford and the hard knocks of hiring gone wrong. With humor, banter, and real-world examples, this episode goes deeper—showing how AI isn’t just about doing things faster, but building a business that thinks, learns,and runs itself.
You’ll Learn:
Links & References
Ready to Take Action?
---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Feeling behind in the AI race? You’re not alone.
In this episode, Kim and Hal pull back the curtain on a truth most business owners miss: you’re already paying for AI—you just haven’t turned it on yet.
Whether you’re a solopreneur drowning in admin, a seasoned agency owner juggling compliance, or a local service shop trying to keep up with customer requests—this episode shows you how to unlock the AI already built into the tools you use every day.
From QuickBooks to Calendly, from CRM follow-ups to LinkedIn hiring filters—Kim and Hal walk you through real-world, low-barrier examples of what it looks like to go from stuck to scaling… in just one click.
And in their signature “Coffee Table Conversation,” they share a laugh-out-loud story of using AI to hunt for commercial real estate—with a security guard and a suspicious parking lot moment included.
This isn’t about hype... It’s about help.
And it starts with one click.
Key Takeaways
Mentioned Tools & Use Cases
Ready to Take Action?
---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
One year. 53 episodes. And today, we reveal Your Year-TwoBlueprint for Small Business Success: 3 plays to scale smarter, 2 traps to avoid, and 1 decision you’ll want to make in the next 7 days—so you can build a true superpower.
You’ll Learn
In this milestone anniversary episode, Kim and Hal look back at the biggest lessons of year one and reveal the Year-Two Blueprint: the 3 plays to win, 2 traps to avoid, and 1 decision that will shape your next 7 days.
If you’re a solopreneur buried under a CVS-length to-do list—this year proved that AI can help you reclaim hours and reduce burnout.
If you’re a growth-focused entrepreneur—this year showed that AI isn’t just about efficiency, but about building resilient, predictable, future-proof systems.
Along the way, you’ll hear Hal’s strategist take (“leverage beats hustle every time”), Kim’s rally cry, and even a blooper to celebrate how far this community has come.
This isn’t about chasing shiny apps. It’s about designingyour operating system for growth.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
The deal room is where businesses rise… or collapse.Whether you’re buying a company, signing a lease, or just negotiating with a vendor, the stakes are high — and the old ways of due diligence aren’t enough.
In this episode of Small Business Big AI, Kim shares her real-world story of scouting office space for her new AAA agency — and how AI helped her see the red flags before locking into a deal. Joined by strategist Hal, they break down the Predict → Generate → Automate playbookand the Red Flag Radar (Compliance • Customers • Cash), showing how to use AI as a spotlight to expose hidden risks, protect your margins, and make better business decisions.
This isn’t about replacing human judgment — it’s aboutamplifying it. And with the tidal wave of Baby Boomer business exits underway, the winners will be those who walk into the deal room with clarity, not chaos.
You’ll Learn
1. How AI transforms due diligence for acquisitions, leases, and vendor deals.
2. The Predict → Generate → Automate playbook for smarter business strategy.
3. How to build a simple Red Flag Radar (Compliance, Customers, Cash) to avoid costly mistakes.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Google changed the rules. SEO is shifting. Here’s howsmall businesses can win before the big brands even catch up.
What You’ll Learn in This Episode:
In this episode of Small Business Big AI, Kim and Hal break down:
Whether you're a solopreneur, consultant, agency owner,or local brand, this episode will give you a playbook to stay visible, connect faster, and hedge against disruption.
Featured Strategy Concepts:
Tools + Mentions:
Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Feeling invisible in a noisy marketplace? You’re not alone. Millions of small businesses are competing for the same customers, but here’s the secret: survival isn’t about going bigger—it’s about getting sharper.
In this episode of Small Business Big AI, Kim and Hal reveal how AI helps you stop fighting over scraps in the crowded ocean and start owning your own pond—a hyper-niche where you become the go-to authority.
What You’ll Learn in This Episode:
Why This Matters Now:
With tariffs, inflation, and economic uncertainty puttingnearly 40% of small businesses at risk, playing it safe by being “generic” is the fastest road to failure. In today’s market, niching down is survival—and AI is the compass that helps you navigate.
Challenge of the Week:
Jump into a social media community in your industry. Use AI (even a smart ChatGPT prompt) to uncover one recurring frustration no one is solving. That’s your first step toward finding your pond.
Listen If You’re:
🎧 Tune in now and learn how to own your pond, build trust fast, and thrive in a tightening economy.
Subscribe & Review
If this episode sparked an idea, share it with another entrepreneur who needs it. Don’t forget to hit subscribe and drop a quick review—it helps more small business owners discover how to build their own technology-enabled superpower.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Tariffs are spiking, supplier prices are jumping, and small business owners are feeling the squeeze. In this episode of Small Business Big AI, Kim and Hal bring Olivia, our solopreneur persona, to the Coffee Table to face a real scenario: what happens when supplier costs jump 30%overnight?
You’ll discover how AI isn’t just about working faster —it’s about making your business safer. From spotting storms early, to modeling the financial impact, to acting with clarity, this episode delivers a practical AI playbook for surviving and thriving when margins are under fire.
What You’ll Learn:
Don’t just hustle harder. Learn how to think better with AI as your business safety net.
Subscribe & Share: Don't miss out on future episodes of Small Business Big AI. Subscribe on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.
Ready to Take Action?
---Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
If you think “someday” is the right time to start your business, think again—someday is here. In this high-voltage episode of Small Business Big AI, Kim and Hal break down why this is the most opportunity-rich moment in modern history for entrepreneurs… and why waiting could cost you everything.
From tearing down the old barriers to entry, to automating the busywork that drains your energy, to tapping into high-level expertise once reserved for Fortune 500 giants—this isn’t just about starting a business. It’s about joining a movement. A movement where small, smart, and strategic beats big and bloated every time.
By the end, you’ll know how to start turning your ideas into action—fast—so you can step into your technology-enabled superpower and claim your spot in the entrepreneurial revolution.
What You’ll Learn in This Episode:
Links & Resources Mentioned in This Episode:
Tools to explore for this week’s challenge:
o ChatGPT — Content creation, research, automation ideas.
o Zapier — Workflow automation for repetitive tasks.
o Canva — Fast, AI-powered design.
o Otter.ai — Automated transcription & meeting notes.
Episode CTA:
Your challenge this week: Pick one repetitive task in your business and automate it using AI. When you do, DM Kim on LinkedIn or tag it with #SmallBusinessBigAI. Your win could inspire another entrepreneur to step into their technology-enabled superpower.
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Ever feel like you're stuck doing intern-level tasks in your own business? In this unforgettable, story-driven episode, Kim walks you through a real-life transformation—from administrative chaos and chargeback panic to clarity and control—all powered by AI.
This week, we're not just talking about AI tools. We're showing you how to fire the intern and hire the assistant—without adding headcount. Whether you're tired of sorting emails, chasing customer refunds, or cleaning up after your overworked team, this is your moment to reclaim your CEO mindset.
What You’ll Learn:
Episode Highlights:
Tools Mentioned in This Episode:
1. ChatGPT [https://chatgpt.com/]
Your always-on writing assistant. Use it to auto-draft emails, generate social media posts, create newsletter content, and more.
2. SaneBox [https://www.sanebox.com/]
Email inbox management powered by AI. It sorts unimportant emails into folders and prioritizes what matters—saving you hours every week.
3. Zapier [https://zapier.com/]
The ultimate automation tool that connects your apps and workflows. Use it to create automations like “if someone books a meeting, send a follow-up email.”
4. Stripe Radar [https://stripe.com/radar]
An AI-powered fraud detection system for Stripe users. It monitors and flags suspicious activity on your transactions in real-time to help reduce chargebacks.
5. Notion [https://www.notion.com/]
Your second brain for organizing customer data, receipts, content plans, and chargeback documentation. Bonus: integrates beautifully with Zapier.
Challenge of the Week:
Pick one intern-level task you've been doing far too long—drafting emails, posting on social, or processing refunds. Fireyourself from it.
Then choose one AI tool to take it over.
Tag @SmallBusinessBigAI on LinkedIn and use the hashtag #FiredTheIntern to share what you automated!
Subscribe & Share: Don't miss out on future episodes of Small Business, Big AI. Subscribe on Spotify or your preferred platform, leave a review, and share this episode with a fellowentrepreneur who could benefit from AI insights.
Ready to Take Action?
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Two entrepreneurs. Same resources. Same goals. Verydifferent results.
In the final episode of our Mindset & Messaging mini-series, Kim and Hal expose the pivotal mindset shift separating thebusiness owners who scale from the ones who stall. If you’ve been burned out, buried in busywork, or hesitant to fully embrace AI—this episode is your rally cry.
Because this isn’t about tech skills. It’s about identity.
In this high-impact finale, you’ll discover:
This episode will challenge you. Inspire you. And most importantly—it will equip you to lead your business into the AI-powered future with clarity and confidence.
Resources & Links:
If you loved this episode: Leave a review, share it with your fellow business owners, and tag Kim to let her know you’ve joined the movement. Because the future of your business is bigger than you think. And the steps you take today will shape the legacy you build tomorrow.
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Feeling behind on AI? You’re not alone—and you’re notfailing.
In this episode of Small Business Big AI, Kim and Hal dive deep into the real reason so many small business owners hesitate to adopt AI… and spoiler alert: it's not the tech.
It’s fear.It’s identity.It’s the deep emotional friction that comes with changing the way you work, lead, and show up.
Through the relatable story of “Mark”—a seasoned business owner stuck in outdated systems—you’ll uncover the silent ways hesitation is sabotaging growth and how micro-actions can build the courage to move forward.
You'll learn:
This isn’t about tools. It’s about transformation—starting with a single, brave step.
Challenge of the Week
Find one task you’ve been doing manually—out of habit orfear—and hand it to AI this week. Then tag us or DM Kim with your story using #AIBraveMove on LinkedIn, X, or Facebook.
We’ll share a few of our favorite breakthroughs in next week’s episode!
Subscribe + Share
If this episode gave you clarity, courage, or just a goodlaugh (looking at you, pirate voice AI), subscribe and leave a review. Your feedback helps us empower more small business owners like you to thrive in the AI era.
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
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Welcome to Small Business Big AI! In this powerful third episode of our Mindset & Messaging summer series, Kim and Hal dive deep into the mindset shift every small business owner needs to survive and thrive in the AI era.
Are you still stuck wearing the “chief doer” hat — grinding, hustling, and managing every detail? It’s time to trade it forthe “chief architect” hat and start leading like a transformer. This episode exposes the 7 hidden technician traps that cause most AI projects to stall or fail — and shares how to avoid them with city-planner precision.
What you’ll learn in this episode:
Why you can’t afford to miss this episode
If you’re still firefighting, buried in data chaos, or chasing the latest shiny AI tools without a clear plan—this episode is yourwake-up call. Kim and Hal bring the tough truths, practical solutions, and real-world stories (including Jordan’s journey) to help you build an AI strategy that’s scalable, sustainable, and profitable.
Resources & Links Mentioned
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
The AI era isn’t coming. It’s here—and it’s already rewriting the rules of business. So, the question isn’t if you should adopt AI—it’s how fast your competitors already have.
In this episode, Kim and Hal cut through the noise to reveal what’s actually happening behind the scenes for small business owners in today’s AI-driven marketplace.
✅ Feeling overwhelmed by AI hype?✅ Wondering how to stay competitive without losing your soul?✅ Curious how real small businesses are using AI right now to gain an edge?
This episode is for you.
In This Episode:
Featured Framework: SBTM
The Small Business Transformation Model isn’t just another acronym—it’s your new AI-powered playbook. From mindset shifts to automation audits, this 5-step model helps small business owners build systems that scale.
✳️ Want a guided walkthrough? Email Howard & Howard Holdings, Inc.
Mentioned:
🎓 NEW: Learn to Talk to AI Like a Pro
Want to master prompt engineering without needing acomputer science degree? Enroll in Kim’s signature course: "From Overwhelmed to Empowered" Learn the IMPACT Framework and how to use AI to reclaim your time, sharpen your strategy, and grow your business. 👉 Request to Join our Private Community
Love the Show? Here’s How to Support:Have a question or an AI success story? DM us on LinkedIn or Facebook!
Share this episode with a fellow entrepreneur; Tag us @SmallBusinessBigAI on LinkedIn; DM Kim your #1 AI challenge and she just might feature your question in an upcoming episode
Episode Quote to Share:
“AI won’t replace you. But someone using AI—strategically, intentionally, creatively—absolutely will.”
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
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Feeling overwhelmed by your business—but too busy tofix it? This episode is your wake-up call.
In today’s can't-miss conversation, Kim and Hal take on one of the most glorified lies in entrepreneurship: that hustle alone is the secret to success. Spoiler alert—it’s not. In the age of AI, grit without leverage leads to one destination: burnout.
You’ll hear:
Whether you’re a solopreneur juggling a dozen roles or asmall business owner scaling fast, this episode will challenge how you work—and inspire a smarter, more scalable future.
Who This Episode Is For:
Ready to Take Action?
Listen Now If You’re Ready To:
✅ Stop confusing 'busyness' with business✅ Reclaim your time, energy, and strategic focus✅ Turn burnout into breakthrough✅ Finally use AI to scale—without losing control
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
Loved this episode? Share it with a fellow founder who’s stuck in hustle mode.
Are you future-proofing your business—or just hopingfor the best?
In the final chapter of our 3-part Human-AI Harmony Revenue Playbook, Kim and Hal expose the hard truth most entrepreneurs are avoiding: AI isn’t coming—it’s already here. And it’s about to decide who grows... and who gets left behind.
In this episode, we go beyond AI tools and into strategy—showing you how to build an “always-on” innovation engine that keeps your business ahead of market shifts, customer trends, and the competition. You’ll learn why small businesses that wait for the “perfect moment” are quietly becoming obsolete—and how to become the technology-enabled superpower your industry didn’t see coming.
In this episode, you’ll discover:
Perfect for:
Small business owners, solopreneurs, franchise founders, consultants, and creators who want to:
✅ Stay relevant in an AI-driven economy
✅ Turn overwhelm into strategy
✅ Build a resilient business that adapts and scales with confidence
Listen if you’re wondering:
Action Step from Kim & Hal:This week, identify one recurring bottleneck in your business—and spend 30 minutes exploring how AI could automate or simplify it. Small moves. Big momentum.
Ready to Take Action?
🎵 Available on Apple Podcasts, Spotify, YouTube, and all major platforms.
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/