

Business Brain – The Entrepreneurs’ Podcast
Shannon Jean & Dave Hamilton
Two long-time small-business owners, Dave Hamilton and Shannon Jean, come to you each week to talk through the trials, success, pitfalls and tips it takes to successfully run a small business in today’s world. Hear real-world folks talk about real-world problems, letting you know not only what it takes to get it done but that you’re not alone in doing it!
Episodes
Mentioned books

Nov 7, 2025 • 23min
FridAI - ChatGPT Tricks + Limitless Pendent
You’ll learn how to supercharge your entrepreneurial workflow with AI as Shannon and Dave dive into the latest ChatGPT tricks, from snapping store photos to capturing screenshots and shaping your business philosophy with better prompts. You’ll discover how adding context helps AI think more like a partner and less like a tool—helping you make sharper, faster decisions. This is all about working smarter so you can live your Charmed Life.
They also explore the world of wearable AI, including the Limitless Pendant and its seamless sync with Apple Reminders. With real talk about privacy, productivity, and where tech is headed next, this episode gives you a front-row seat to the future of entrepreneurship—powered by AI and grounded in business savvy.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #699 for Casual FridAI, November 7th, 2025
00:01:30 November 7th: Love Your Lawyer Day
00:02:26 ChatGPT: Using the Camera in the store
00:06:08 Taking screenshots from within ChatGPT
00:06:54 Using ChatGPT To Hone your Business Philosophy
The more context you give it, the better they are at predicting and helping you solve problems
Sponsors
00:10:42 SPONSOR: Surfshark. Go to https://surfshark.com/businessbrain or use code businessbrain at checkout to get 4 extra months of Surfshark VPN!
00:12:22 SPONSOR: PAKA. Softer than Cashmere and warmer than wool. Visit Go.PAKAapparel.com/BRAIN to grab your PAKA hoodie and free pair of alpaca crew socks.
00:14:07 Todd-Privacy concerns with wearable AI Pendants?
00:17:24 Limitless syncs with Apple Reminders
00:19:32 NEO Home Robot
00:22:20 Business Brain 699 Outtro
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Nov 5, 2025 • 25min
Age is Just Another Wave to Ride
As you navigate the waves of life and business, this episode reminds you that age isn’t a limitation—it’s momentum. Shannon and Dave dive into how your brain evolves from chasing facts to harnessing wisdom, helping you spot patterns and ride bigger waves of opportunity. You’ll learn to see mistakes as tuition and fear as a tool, not an obstacle. Whether you’re 25 or 65, you can turn experience into advantage and live your Charmed Life.
They break down how to flip fear-based thinking into forward motion, using uncertainty as fuel for smarter, faster decisions. If you’ve ever worried about slowing down or missing your next big break, this episode shows how every wave—no matter when it comes—can carry you further than you imagined.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #698 for Wednesday, November 5th, 2025
00:01:33 November 5th: Bonfire Night
00:02:06 Age is just another wave to ride
Charlie Munger: Find a wave and ride it!
Brains change as we age: from memorization to big-picture wisdom
Mistakes are tuition
Demi Moore’s The Substance
00:13:19 SPONSOR: Surfshark. Go to https://surfshark.com/businessbrain or use code businessbrain at checkout to get 4 extra months of Surfshark VPN!
00:14:58 SPONSOR: PAKA. Softer than Cashmere and warmer than wool. Visit Go.PAKAapparel.com/BRAIN to grab your PAKA hoodie and free pair of alpaca crew socks.
00:16:43 Revisiting Fear-Based Decisions
Having an irrational fear of not making any money is a superpower
What’s the most important thing to do right now to increase my revenue?
Trading Places is a Christmas Movie
00:23:47 Business Brain 698 Outtro
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Oct 31, 2025 • 22min
FridAI - BrowserAI
You’re already using AI every day—but are you actually using it smartly? In this week’s Business Brain, Shannon Jean and Dave Hamilton explore the next level of practical AI for entrepreneurs, from using your browser to scrape data instantly to letting AI listen, watch, and analyze what’s happening in your business. You’ll learn how to troubleshoot, research, and brainstorm faster just by speaking to your computer, snapping a video, or using your browser as your AI command center.
You’ll also hear about the tools that make it all click—Comet, Atlas, and Limitless—and how connecting them with ChatGPT can help you organize, motivate, and stay consistent with your goals. It’s a mix of humor, experimentation, and smart shortcuts that show you how to work less, create more, and live your version of a Charmed Life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #697 for Casual FridAI, October 31, 2025
October 31st: National Knock Knock Joke Day
00:00:01 AI Tip: Use your computer’s microphone to just dictate to AI. Not speech mode, just instead of typing.
00:02:10 More on using ChatGPT with multiple modes: audio, video, pictures
Take video of your washing machine to troubleshoot.
Is “prompt engineering” just text?
00:07:34 AI Tip: Using AI in your browser
Comet Browser
Atlas Browser
Instant Data Scraper for Chrome
00:11:25 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:13:11 AI Tip: Use ChatGPT to find contacts at companies
Seamless.ai
00:15:19 Limitless Pendant Review Update
Linking Limitless with ChatGPT
Using Limitless to create your to-did list (for motivation!)
00:21:13 Business Brain 697 Outtro
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Oct 29, 2025 • 21min
Motivational Endurance
You already know that building a business is a marathon, not a sprint—but how do you keep running when the finish line keeps moving? In this week’s Business Brain, Shannon Jean and Dave Hamilton dive into the concept of Motivational Endurance, sharing ways to recharge your entrepreneurial drive and find joy in the daily grind. From creating a “To Did” list that celebrates small wins to finding multiple sources of motivation, you’ll learn how to build habits that fuel long-term success and keep your energy high even when your excitement dips.
You’ll also discover why mentoring others (even accidentally) might be the secret to staying inspired and how defining your Noble Cause keeps you aligned through setbacks. When you stack truth with creativity and discipline with purpose, business stops feeling like a struggle—and starts looking like your version of a Charmed Life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #696 for Wednesday, October 29, 2025
00:01:01 October 29th: National Cat Day
00:02:42 Robert-A Side Hustle: Until the Junk Runs Dry!
Start your side hustle today
Boredom is the enemy
Ask your employees: What are your interests? What do you want to do beyond this?
feedback@businessbrain.show
00:08:40 RGoodwin55-BB Review – Great Show
00:09:16 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:11:42 Motivational Endurance from Dr. Julie Gurner
00:16:16 Find multiple things that motivates you
Mentoring younger people, even accidentally
Always tell the truth, but make it fantastic
The “To Did” list concept, celebrating your wins
What’s your Noble Cause?
Review Business Brain
00:20:09 Business Brain 696 Outtro
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Oct 24, 2025 • 20min
FridAI - Devil's Advocate Prompts
In this episode of Business Brain, Dave and Shannon kick off a lighthearted Casual FridAI conversation that revolves around practical AI tips and how they’re integrating AI tools into everyday problem solving. Dave shares a recent experience using the ChatGPT mobile app to diagnose a foot issue by uploading and annotating photos directly in the app, highlighting how powerful visual AI has become for troubleshooting real-world tasks. Shannon adds examples of how he uses AI to identify dashboard warning lights, analyze auction pallet photos, and even figure out how to put a rental SUV into drive. This leads into a discussion on how AI is evolving rapidly and is now becoming a daily assistant rather than a novelty.
The conversation shifts into AI prompting strategies, including Dave’s method of pasting his final edited drafts back into ChatGPT so it continues learning his writing voice. Shannon introduces a new concept he calls the “Devil’s Advocate Prompt” to counteract AI’s built-in positivity bias. Since most AI tools tend to support user ideas without challenging them, this prompt forces AI to critique weaknesses, risks, and flawed assumptions so entrepreneurs can battle-test ideas before launching. They end by talking about building an evolving prompt library for Business Brain listeners and encourage listeners to share their own AI prompt wins.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #695 for Casual FridAI, October 24, 2025
October 24th: World Tripe Day
00:01:46 Annotate images in the ChatGPT app
00:05:11 Upload a photo to help you fix something that’s broken
SIXT Car Rental Agency
00:08:15 SPONSOR: Surfshark. Go to https://surfshark.com/businessbrain or use code businessbrain at checkout to get 4 extra months of Surfshark VPN!
00:09:47 SPONSOR: PAKA. Softer than Cashmere and warmer than wool. Visit Go.PAKAapparel.com/BRAIN to grab your PAKA hoodie and free pair of alpaca crew socks.
00:11:42 FridAI Prompt: “Here’s the final version I edited so you have it for the next time we work on something together”
00:13:34 FridayAI Devil’s Advocate Prompts:
The general Devil’s Advocate Prompt: “Act as a ruthless devil’s advocate. Your job is to find weaknesses, risks, and flawed assumptions in the following idea. No praise, no compliments—only critique and what could go wrong. Provide clear examples and evidence where possible. Here’s the idea: [INSERT IDEA].”
Execution Reality Check Prompt: “Assume this plan sounds good in theory but fails in practice. Explain why execution would break down—team issues, complexity, hidden costs, dependencies, time delays. Plan: [INSERT].”
00:17:24 Business Brain 695 Outtro
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Oct 22, 2025 • 26min
10x instead of 2x
In this episode of Business Brain, Shannon Jean and Dave Hamilton explore the difference between 2x and 10x growth mindsets. Shannon shares a quote from a recent event — “focus on 10x, not 2x” — and breaks down how the 2x approach is about working harder and incrementally improving, while 10x thinking requires transformative change, ruthless prioritization, and bold decision-making. They discuss how 10x growth forces entrepreneurs to abandon outdated systems and focus only on what delivers real results, even if that means disrupting what’s already working. Shannon relates this to his recent Instagram growth experiment and how it’s forcing him out of his comfort zone.
The conversation then shifts to the concept of “body doubling,” a technique Dave discovered during a recent trip where he and his wife worked productively side by side in a hotel room. This unintentional co-working setup led to high focus and output, prompting Dave to dig deeper into the psychological science behind it. They explore how having someone else nearby — even if not directly interacting — creates a low-level accountability and modeled behavior that can improve productivity. They wrap up with a reminder to stay self-aware, keep pursuing growth, and stay focused on high-leverage actions — like selling unused assets or building scalable systems — that generate real revenue.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #694 for Wednesday, October 22, 2025
October 22nd: International CAPS LOCK Day
Wind chimes for podcasting calmness
00:02:07 Focus on 10x-ing, not 2x-ing
Is Grant Cardone just blowing hot air, or does he have something valuable to say?
2x means:
Work harder
Add helpers
Same offer
Fear of losing what you have
Your identity remains the same
10x means:
Same or fewer hours
Build scalable systems, by breaking things and streamlining what you do
New offer
Willingness to destroy what isn’t essential
Your identity evolves
Don’t be afraid to ask: how are you doing 10x what I’m doing?
00:10:27 On Shannon’s Quartet:
Think Bigger
10x instead of 2x
00:11:14 SPONSOR: Surfshark. Go to https://surfshark.com/businessbrain or use code businessbrain at checkout to get 4 extra months of Surfshark VPN!
00:12:46 SPONSOR: PAKA. Softer than Cashmere and warmer than wool. Visit Go.PAKAapparel.com/BRAIN to grab your PAKA hoodie and free pair of alpaca crew socks.
00:14:40 Body Doubling for ADHD productivity – Vincent from Strawberry.me
Time constraints make a big difference, too
“What should I be working on that’s going to generate the most revenue today?”
Bringatrailer.com – car auction site
00:24:42 Business Brain 694 Outtro
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Oct 17, 2025 • 25min
FridAI - ChatGPT Did My Taxes?!
Dave and Shannon open Casual Friday with a Shopify nod, then spotlight listener David’s “vibe-coded” Replit app for high-school sports. His web iPad tool tracks scoring, fouls, streaks, and biggest leads, exports structured summaries to an AI project, and let him publish recaps before leaving the gym. The hosts urge productizing it as a simple SaaS for local media and parents, noting how low-code iteration unlocks niche, high-value workflows.
Listener Ian contributes a prompt to reduce ambiguity in text communications—analyze likely interpretations, confirm intent, then offer two clearer rewrites—which sparks a broader discussion about using AI to keep customer-service tone friendly over SMS. Shannon then explains how he used ChatGPT for tax prep: export a Gmail “receipts” label via Google Takeout, auto-extract 2024 transactions, categorize them, cross-check with credit-card summaries (dedupe, find misses), and organize 1099s/K-1s for his accountant—plus a “what am I wasting money on?” audit to cut subscriptions. They close by inviting listeners to send their own AI workflows to feedback@businessbrain.show.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #693 for Casual FridAI, October 17, 2025
October 17th: National Clean Your Virtual Desktop Day
00:01:16 David-Replit vibe-coded me an app I wanted!
00:08:00 Ian-FridAI-Here’s a prompt to help reduce communication ambiguity
PROMPT: Analyze my text for possible interpretations. Rank them by likelihood based on how most readers would understand the wording. Ask me to confirm which meaning I intend. Then, provide two alternative rewrites that eliminate ambiguity while preserving my tone: [paste text here]
00:10:00 Beware of customer service handling via text. You have to go over the top to be friendly.
00:13:40 SPONSOR: Shopify – For anyone to sell anywhere, sign up for a one-dollar-per month trial period at Shopify.com/BusinessBrain and upgrade your selling today!
00:15:17 Shannon: ChatGPT Did My Taxes
Google Takeout
Is this a prison decision or a penalty decision
Upload your credit card statement to ChatGPT and ask it, “what am I wasting my money on? Be harsh. Tough love.”
00:23:55 Business Brain 693 Outtro
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Oct 15, 2025 • 23min
Dave and Shannon AMA
Dave and Shannon kick off episode 692 with a Shopify sponsor read and dive into listener-submitted interview questions. Jeff’s favorite prompt—“How many gas stations are in the U.S.?”—is used to evaluate problem-solving under pressure, not factual recall. Shannon riffs on the persuasive power of specific numbers and “making the truth fantastic,” while Dave notes real estimates vary widely. Todd’s “What would you put on a bumper sticker?” uncovers candidates’ core beliefs; the hosts swap their own slogans and talk about how pithy lines often emerge over the years, not on demand.
Listener Andrew asks whether his fabrication LLC should bill his rental-property LLC. The hosts recommend billing (or at least tracking) to expose true margins, enable clean property-level P&Ls, support valuations, and strengthen leverage with banks or vendors—while reminding Andrew to confirm structure and tax treatment with a CPA and attorney. They wrap by inviting more questions at feedback@businessbrain.show and signing off with their “charmed life” mantra.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #692 for Wednesday, October 15, 2025
October 15th: National Take Your Parents to Lunch Day
00:01:34 Jeff-More favorite interview questions
Make the truth fantastic!
00:07:52 Todd-Interview question…the Bumpersticker!
00:11:52 SPONSOR: Shopify – For anyone to sell anywhere, sign up for a one-dollar-per month trial period at Shopify.com/BusinessBrain and upgrade your selling today!
00:13:30 Andrew-Should I bill myself for work I do?
00:22:21 Business Brain 692 Outtro
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Oct 10, 2025 • 22min
FridAI: ChatGPT Tasks + AI in the Movies
Dave and Shannon kick off episode 691 on National Handbag Day, segueing from Shannon’s experiment that grew into selling 7,000 handbags and nearly $4M in revenue. He explains how handbags taught him the power of emotional selling and confidence-driven purchases. The conversation pivots to ChatGPT “tasks” (automations) that perform timely research and send results—born from Dave’s football-pick workflow—and expands to examples like weekly industry briefings, sponsor invoicing reminders, and Apple Shortcuts/Zapier/IFTTT integrations to reduce friction and beat procrastination by starting work for you.
They broaden the lens to AI’s impact on creative industries: gatekeepers vs. discovery, parallels to self-publishing in books and indie music, and the rise of AI actors. Their stance: embrace the new tools, accept pros and cons, and focus on execution and curation. A Masterclass sponsor read reinforces continuous learning. They close by inviting listener feedback and reviews (with a MacBook giveaway) and sign off for the weekend.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #691 for Casual FridAI, October 10, 2025
00:01:00 October 10th: National Handbag Day
00:01:52 ChatGPT Tasks to stay on top of your projects
IFTTT
Zapier
Apple Shortcuts
Morning Briefings – then create the LinkedIn post to present me as a thoughtleader in the industry
Reminders for focus
And more…
00:09:04 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:10:54 More automations
00:13:32 AI and the dying, legacy movie industry
Sora Video Creator
Self-publishing with Vellum
00:15:32 The changes in the music industry…What’s next?
Solving the music discovery engine
00:21:04 Business Brain 691 Outtro
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Oct 8, 2025 • 21min
Execution > Information
Dave and Shannon open episode 690 on National Fluffernutter Day with playful banter before diving into the core theme: “execution is the moat, not information.” They argue that oversharing isn’t risky because ideas are plentiful; what matters is doing the work. Dave recalls advice from a VC contact that asking for NDAs is a rookie move—investors back people who will execute, not just ideas. Sharing publicly sharpens thinking, invites useful critique, and reinforces learning, while daily incremental action is what separates success from stagnation. They weave in a Masterclass sponsor segment as an example of learning that fuels better execution.
They then highlight customer service as a universal responsibility. Dave shares two contrasting experiences in the same week: the USPS quickly resolved a stuck tracking issue for an eBay iPhone shipment by updating the delivery scan, leading to released funds; a UPS driver showed uncommon courtesy in traffic, modeling brand-aware behavior. The takeaway: every business—and every employee—is in customer service because any touchpoint shapes the brand. They invite listeners to share how they train teams to represent the company well and sign off, encouraging everyone to keep living that “charmed life.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #690 for Wednesday, October 8, 2025
00:00:56 October 8th: National Fluffernutter Day
00:02:13 Aren’t you worried about over-sharing your secrets?
“Execution is the moat, not information.”
00:09:49 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:12:00 USPS delivers excellent customer service!
00:15:50 …and so does UPS
Every employee is in the customer service department
00:19:50 Business Brain 690 Outtro
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