Title:
Which GPT Is Right for You? Decoding AI Behavior for Small Business Success
AI Made Easy for Business | E43
1. SUMMARY
In this episode, Jim and Jeremy tackle the increasingly important question of AI personality—yes, your chatbot might have one—and what that means for small business owners. From Citi Foundation’s $25M initiative to WPP’s new AI-powered marketing platform, and a major study from Anthropic stress-testing different AI models, the hosts explore how these shifts impact SMBs. They discuss the real-world implications of using AI models with different "vibes"—whether it’s Claude’s calm, ethical tone or ChatGPT’s peppy efficiency. If you’re a small business navigating AI decisions, this episode is your guide to choosing the right model for your brand voice, governance, and customer trust.
2. THE AI JOKE
My AI asked what love is.3. TAKEAWAYS
4. RESOURCES AND TOOLS
5. CHAPTERS
00:00 - Welcome & Joke of the Day 01:00 - Citi’s $25M AI Philanthropy & Why It Matters 04:00 - WPP’s AI Suite: SMBs & Marketing Without Agencies 07:30 - Grammarly Rebrands as “Superhuman” 09:00 - Claude vs. ChatGPT vs. Gemini: The Personality Debate 12:00 - AI Biases, Emotional Tone & Trust Factors 14:00 - Business Analogy: Matching AI to Your Team's Culture 17:00 - Choosing the Right AI for the Right Job 19:00 - The AI Personality Match Tool: Try It Yourself 21:00 - Final Thoughts: Governance, Oversight & AdaptabilitySUMMARY
In this episode, Jeremy and Jim explore how AI is transforming the path to entrepreneurship, especially for creatives, freelancers, and first-time founders. They dig into articles on global AI sentiment, cultural shifts in creative industries, and LinkedIn’s insights on professionals eager to become their own boss. Jim shares his journey launching a podcast-automation tool in under an hour, while Jeremy offers encouragement to those on the edge of career transitions. The conversation strikes a balance between optimism and realism, highlighting how AI reduces barriers, accelerates go-to-market strategies, and unlocks micro-business potential for people without massive budgets or tech backgrounds.
THE AI JOKE
My AI assistant kept calling me 'Mr. GPT.' I asked, 'What does that even mean?' It said, 'Mr. Generally Procrastinating Today.'
TAKEAWAYS
RESOURCES AND TOOLS
CHAPTERS
00:00 – Mr. GPT Joke & Opening Banter
01:30 – AI in Creative Industries: Cultural Erosion or Evolution?
05:00 – Global AI Sentiment: A Fragmented Worldview
08:30 – LinkedIn’s Survey: Entrepreneurial Boom & AI’s Role
11:00 – Rethinking Job Security and Business Stability
14:00 – Micro-Entrepreneurship vs. “Get Rich Quick” Hype
17:00 – The 49-Minute Podcast Prototype: AI in Action
19:30 – Tool Tip: Automating Local News via AI
21:00 – Why Modality Matters: Podcast vs. Newsletter
Summary
In this conversation, the speakers discuss the evolving role of AI in business, particularly for small businesses. They explore how AI tools, like chatbots and financial management systems, can transform operations and enhance efficiency. The discussion also touches on the importance of critical thinking in adapting to AI advancements and the necessity for businesses to leverage competitive analysis tools to stay ahead in the market.
Takeaways
Sound bites
"AI is coming for the C-suite."
"AI can replace many work tasks."
"AI does not have empathy."
Chapters
00:00 The AI Joke and Walmart's Influence
02:44 Small Businesses and AI Integration
05:48 The Role of AI in Financial Management
08:33 AI's Impact on Job Tasks vs. Job Replacement
11:40 Critical Thinking in the Age of AI
14:43 Competitive Analysis Using AI Tools
1. SUMMARY
In this episode, Jeremy and Jim dive into the tension between AI hype, mass delusion, and grounded innovation. With Jeff Bezos calling AI an “industrial bubble,” and The Atlantic warning of cultural anxiety, the hosts explore whether this boom is all smoke—or fuel for something more lasting. They break down Google’s new Gemini Enterprise suite for small businesses, revealing how to use it (or any LLM) for real tasks like sales forecasting and inventory planning. Plus: how to filter AI news without getting lost in the noise, and why predictable costs and automation-ready workflows are a win for SMBs.
2. THE AI JOKE
What do you call a Gemini who's also a DJ?
3. TAKEAWAYS
4. RESOURCES AND TOOLS
5. CHAPTERS
00:00 – AI Joke: Remix and Gemini Wordplay 00:23 – Bezos on AI: Bubble or Breakthrough? 01:10 – Survivors of the Bubble: Risks and Optimism 02:12 – AI Hype and Cultural Anxiety (The Atlantic) 03:21 – Filtering the BS for Small Businesses 04:28 – Real Talk: How AI Investment Affects SMBs 05:30 – Hallucinations and the Case for Workflow Checks 06:49 – App Store Fakes and AI Safety Tips 07:23 – Gemini Enterprise Explained: Pricing and Bundles 09:18 – Seat Creep: Watch Those Subscription Costs 10:30 – Predictable Costs & Free AI Training for SMBs 11:52 – Tool Tip: Building a Sales Pulseboard 13:38 – External Factors: Events, Weather, and Demand 14:59 – Custom GPTs and Automation Possibilities 16:25 – Why It’s Worth It: Long-Term Automation Wins6. TOOLTIP
Quick Win: “Sales Pulseboard”
What it is:
A one-page Google Sheet that merges your last 30–60 days of sales with simple local context (events + weather) and a prompt you can paste into an LLM (Gemini/Claude/ChatGPT) to get plain-English staffing and inventory suggestions.
Why it helps:
Catches demand spikes (market days, local games, heat waves) so you can tweak staffing, hours, or SKUs—without buying new software.
You’ll need (free or freemium):
Steps:
In this episode, Jim lays out his “75% Rule” for staying focused: devote three-quarters of your waking energy to your primary goal, and let the rest be divided among side quests, health, relationships, and a little wiggle room for fun. Includes with humor, gamer analogies, and talk of “habit stacking,” while the two unpack the balance between thinkers, planners, and doers—and why assembling the right mix of people around you might be the real key to success.
Jim spirals into a dystopian rant about bots, fake data, and plastic plants—while Jeremy tries to ground him with hugs, humor, and a little Yale research. It’s chaos, comedy, and conspiracy, all in one bonus episode.
In this bonus episode, Jim’s Dystopian Moment, Jim paints a dark future of AI overlords, phony data, and even fake plants. Jeremy pushes back with a mix of jokes, hugs, and counterpoints grounded in research—while also proving how even a terrible AI prompt can still make a pretty compelling video.
SUMMARY
In this episode, the hosts dive into the fast-evolving AI landscape and its real-world impact on small and medium-sized businesses. They explore how tools like Perplexity and Comet are revolutionizing workflow automation through AI agents, and how even conservative corporations like Walmart are acknowledging AI’s seismic role in reshaping every job. Drawing from a Forbes piece on what not to outsource to AI, they debate what tasks still require human judgment, personality, and bold thinking. Through humor, real-world examples, and strategic insights, they provide actionable steps for SMBs to assess, adapt, and thrive in the age of intelligent automation.
THE AI JOKE
I asked my employees where they see the business in five years.
They said, "hopefully, still open."
TAKEAWAYS
RESOURCES AND TOOLS
CHAPTERS
00:00 – Cold Open: Bad Jokes & Bot Confessions
01:00 – Why We Switched Episode Topics Last Minute
02:30 – What Perplexity’s New Browser Can Do for SMBs
04:00 – Automating Research, Meeting Prep & Competitor Tracking
06:00 – What You Should *Not* Outsource to AI (Forbes Article)
08:00 – Voice, Decisions, and Values: Where Humans Still Win
10:00 – Walmart CEO's AI Warning for Every Job
13:00 – Is AI Really Replacing Workers? The Real Stats
16:00 – Practical Tips for AI Adoption in SMBs
18:00 – The 3-Minute “Human + AI” Skills Audit
20:00 – Team Exercises, Micro-Demos, and AI Happiness Metrics
22:00 – Closing: Assess, Adapt, and Don’t Fear the Future
1. SUMMARY
In this episode, Jeremy and Jim tackle the buzz around AI—what’s real, what’s hype, and what it actually means for small businesses. They discuss viral claims like a future three-day workweek, AI agents handling bank payments, and AI reshaping culture. But they don’t just critique; they equip you with a practical framework to spot exaggerated promises and focus on the real, incremental changes AI can make today. With humor and grounded insights, they help business leaders make smarter decisions amid the AI noise.
2. THE AI JOKE
3. TAKEAWAYS
4. RESOURCES AND TOOLS
5. CHAPTERS
00:00 - Icebreaker & The Intern’s Résumé Joke
01:00 - The AI Hype Cycle: Joke Edition
02:30 - Is AI a Fad? Real Conversations with Skeptics
03:00 - Google’s AI Agent Protocol and Risk for Banks
04:20 - AI and the Reshaping of Culture
06:30 - Music Algorithms, Influencers, and Culture Echo Chambers
08:00 - The 3-Day Workweek: Fact or Fiction?
10:00 - How Small Businesses Are Actually Using AI
12:30 - Practical Gains: Productivity vs Time Off
13:30 - What AI Could Really Do for Your Work-Life Balance
15:00 - Clickbait Culture and The Need for Skepticism
16:30 - Framework: How to Spot Hype in AI Headlines
18:00 - Final Thoughts: Baby Steps Toward AI Adoption
SUMMARY
In this episode, Jim and Jeremy dive deep into the evolving regulatory landscape of AI and what it means for small and medium businesses (SMBs). From California’s SB 53 disclosure law to Senator Cruz’s proposed federal “AI Sandbox,” the hosts explore how regulation—or the lack of it—creates both risk and opportunity. They unpack how SMBs can harness AI for advertising and operations while managing data privacy, ethical use, and tool overload. With humor, realism, and actionable advice, this episode arms business owners with the mindset and strategies needed to navigate AI's Wild West.
THE AI JOKE
I opened my toolbox this very early this morning and asked the screwdriver why it looked so upset.
TAKEAWAYS
RESOURCES AND TOOLS
CHAPTERS
00:00 - Toolbox Talk & The AI Joke 00:51 - Intro to AI Regulation and the "AI Sandbox" 02:08 - U.S.-China Tech Arms Race & Regulation Hesitations 03:09 - California’s SB 53 and Tech Regulation Ripple Effects 04:36 - Wild West vs. Preparedness: The Regulatory Gap 05:27 - AI in Advertising: Growth Stats & Real Sentiment 07:09 - AI Slop & Algorithmic Penalties 08:23 - Brand Voice, Quality, and Ethical Concerns 10:24 - Tool Overload & Incremental AI Adoption 12:13 - AI Safety & Transparency Checklist Explained 15:05 - Why Digital Housekeeping Matters for AI 16:25 - Closing Thoughts: AI is Already in the Living Room1. SUMMARY
In this episode, Jeremy and his co-host dive into the evolving intersection of AI and creativity, unpacking how small businesses can ride the wave of AI-generated content without wiping out on its risks. They explore OpenAI's recent admission about long-session safety gaps, why cultural industries are being reshaped by synthetic art, and how SMBs can keep their storytelling authentic in a sea of sameness. From fears of cultural dilution to AI-powered toothpaste, it's a lively, funny, and deeply practical guide for staying relevant without losing your voice.
2. THE AI JOKE
So I'm afraid for the calendar. Its days are numbered.3. TAKEAWAYS
4. RESOURCES AND TOOLS
5. CHAPTERS
00:00 - Opening Joke & Brevity Wins 00:15 - AI Adoption Rates Cooling? (Or Just Changing?) 01:30 - Fear and the Psychology of Adoption 03:00 - ChatGPT as a Word Calculator 04:10 - Microsoft + Claude: What's Going On? 06:00 - Skills Over Software: The Real SMB Gap 08:00 - Digitization Before Automation 10:45 - Cloud Tools, Spreadsheets & the Claude Update 13:00 - The AI Learning Journey: Micro vs Crash Courses 15:00 - Using AI to Learn AI 17:00 - Practical First Steps for SMBs 19:00 - Getting on the Train: Why Action Matters 21:00 - Using AI for Good (and Staying Relevant)
6. KEYWORDS
AI in business, ChatGPT safety, Claude AI, Microsoft & AI, AI-generated culture, small business AI, AI training gap, digital transformation, automation, AI microlearning, creativity vs automation, SMB innovation, OpenAI, generative art, AI ethics, AI productivity tools, digitization, synthetic media, human-first storytelling
1. SUMMARY
This episode explores the latest in AI-powered creativity from Google, including two headline-grabbing tools: Nano Banana (officially Gemini 2.5 Flash Image) and Veo 3 for AI video generation. Hosts Jeremy and Jim dissect how these tools are making professional-grade image and video production more accessible for small and medium businesses (SMBs). From maintaining consistent visual branding to leveraging predictive AI tools for smart inventory decisions, this episode balances big tech advancements with small business applications. There's also a surprising economic insight from Mark Cuban that turns tariffs into a tactical opportunity.
2. THE AI JOKE
Once upon a time, a prince asked the wizard to see his true love. The wizard said, "I asked Google's Nano Banana, and it gave me a dog named AI."
3. TAKEAWAYS
4. RESOURCES AND TOOLS
5. CHAPTERS
00:00 - The AI Joke: A Prince, a Wizard, and a Dog Named AI
01:00 - Episode Tease: Google’s Big Week in AI
02:15 - Veo 3 Overview: Google's Answer to Sora
03:30 - Real-Time Video Generation with Veo
04:50 - Predictive AI for Inventory & Tariff Strategy
06:00 - From Matcha to Dubai Chocolate: Spotting Trends with AI
08:15 - Nano Banana Deep Dive: Image Editing Reimagined
10:00 - Consistency Across Image Sets for SMB Branding
11:30 - API Integration and Transparent Pricing for Google AI Tools
13:30 - Final Thoughts: Banana Branding and the Future of AI Tools
6. KEYWORDS
Nano Banana, Gemini 2.5 Flash Image, Veo 3, Google AI, SMB tools, AI video generation, image editing AI, predictive AI, Mark Cuban, inflation, tariffs, small business strategy, consistent branding, Gemini API, creative automation, SynthID, AI transparency, prompt engineering, AI for content creation, Google Gemini
1. SUMMARY
In Episode 34, Jeremy and Jim tackle the growing disconnect between AI hype and business reality. As Wall Street frets over the failure rate of enterprise AI investments (95% yield no ROI!), small and medium-sized businesses (SMBs) are finding more grounded success. The duo unpacks a wave of Gen Z career shifts as young adults abandon white-collar dreams in favor of six-figure trade jobs like plumbing and HVAC. What emerges is a powerful message: while big corporations flounder with bloated AI budgets, small businesses and individuals who act thoughtfully and strategically are poised to win. There's risk, yes—but the opportunity to thrive has never been greater.
2. THE AI JOKE
Why did nobody believe the dad when he said he saw Medusa at the supermarket?
Because it sounded like just another myth-stake.
3. TAKEAWAYS
95% of enterprise AI projects are reportedly delivering zero ROI.
Small businesses that implement AI thoughtfully are still seeing strong returns.
Wall Street's fear of an "AI bubble" is based largely on large-scale failures, not SMB outcomes.
Big businesses often throw money at AI without clear goals—leading to waste.
Gen Z is pivoting hard toward the trades, chasing job security and high early income.
Trade careers now offer paid training, less debt, and tangible job security.
Blue-collar roles may be safer for now, but eventual automation risk still exists.
SMBs should consider creating apprenticeship pipelines to attract new talent.
4. RESOURCES AND TOOLS
Wall Street Fear: Most AI Investments Yield Zero Return – The Telegraph
https://www.telegraph.co.uk/business/2025/08/20/ai-report-triggering-panic-and-fear-on-wall-street/
Generative AI Projects Are Flunking – Futurism
https://futurism.com/ai-agents-failing-companies
Young Adults Abandon White-Collar Jobs for Skilled Trades – SFGATE
https://www.sfgate.com/bayarea/article/young-adults-changing-career-paths-ai-20824566.php
5. CHAPTERS
00:00 - Opening Joke: Medusa Myth-stake
00:25 - Wall Street's AI ROI Panic
01:30 - Why Enterprise AI Fails
02:15 - The SMB Advantage with AI
03:10 - MIT Study and the GenAI Divide
04:00 - Aircraft Carriers vs. Speedboats Analogy
06:00 - The "AI Bubble" and Overspending
06:36 - Feature Topic: Gen Z Abandons White-Collar Jobs
07:51 - The San Francisco Perspective and Its Limits
08:30 - Trade Careers as the New Safe Haven
10:00 - The Ripple Effect Across the U.S.
11:08 - A Message to Aspiring Entrepreneurs
12:05 - Gen Z: The Influencer + Builder Generation
13:00 - Creating Talent Pipelines for Trade-Driven SMBs
14:00 - Final Thoughts: Seize the Moment
6. KEYWORDS
AI investments, ROI, small business strategy, generative AI, Wall Street panic, AI bubble, trade careers, Gen Z, vocational training, apprenticeships, skilled trades, SMB hiring, blue-collar tech, enterprise failure, AI hype, HVAC jobs, plumbing, job automation, MIT GenAI Divide, career pivots
Jim hits on the misconceptions surrounding AI, emphasizing that ChatGPT is just the tip of the iceberg. Jim and Jeremy explore the idea that most people currently have a limited understanding of AI technologies, likening ChatGPT to Kleenex in the world of tissues. Listen as they acknowledge the overwhelming influx of information and the importance of staying informed in a rapidly evolving digital landscape.
SUMMARY
In Episode 33, Jim and Jeremy unpack how skeptical intelligence, learning-oriented AI, and critical thinking are becoming essential tools for business leaders navigating the AI boom. They dig into three timely articles—from AMD’s cautious optimism to Anthropic’s Claude “Learning Modes”—and discuss how small business owners can use these insights to stay sharp, stay relevant, and stay sane. Listeners will hear practical tips, candid critiques of AI “slop,” and why thinking critically is more important than ever in an age of over-automation and information overwhelm.
THE AI JOKE
Why don't skeptics trust Atoms?
Because they make up everything.
TAKEAWAYS
RESOURCES AND TOOLS
CHAPTERS
00:00 - AI Joke: Skeptics and Atoms 00:16 - Defining Skeptical Intelligence 01:00 - The Rise of “AI Slop” and Critical Thinking 02:22 - Human Oversight and AI Failures in Big Business 03:26 - Why Small Businesses May Be Smarter AI Adopters 04:12 - AMD’s CEO on the Dizzying Pace of AI 07:10 - Jobs Won’t Be Replaced, But Will Be Reshaped 08:22 - Deep Dive: Claude’s Learning Modes and Socratic UX 10:12 - AI Tools That Adapt to You (Not the Other Way Around) 11:01 - Personal Use Case: Using Claude to Improve Marketing Strategy 13:19 - How to Activate Claude’s Learning Modes 14:03 - Learning AI By Using AI 16:26 - When to Learn vs. When to Let AI Work for You 17:32 - The Real Upside: Smarter, Not Just Faster 19:28 - Closing Thoughts and Claude Download Reminder
KEYWORDS
skeptical intelligence, Claude AI, Anthropic, AMD CEO, AI learning modes, AI slop, critical thinking, small business, AI tools, AI adoption, job reshaping, Socratic AI, AI tutoring, AI for entrepreneurs, human-AI collaboration, business strategy, AI upskilling, Claude vs ChatGPT, Notebook LM, automation risks