
Business Brain – The Entrepreneurs’ Podcast
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!
Latest episodes

Jun 6, 2025 • 16min
FridAI - Projects and Strangers
In this Casual Friday episode of Business Brain, Dave and Shannon kick things off with a light-hearted celebration of National Donut Day before diving into a deeper conversation inspired by a post from Dr. Julie Gerner: “If I was a stranger stepping into this person’s life, what would I immediately fix or change?” The hosts explore how objective self-evaluation—or using AI tools like ChatGPT for analysis—can reveal blind spots and offer actionable improvements in business and life. Dave demonstrates this in real-time by prompting ChatGPT, which delivers insightful feedback on his mental clutter, decision-making habits, and money mindset.
The conversation transitions into a practical discussion about organizing information within AI tools. Shannon explains how he uses ChatGPT’s “projects” feature to sort and manage long-term content from his podcast, coaching, and other ventures—offering a systemized way to track insights and reuse assets. They touch on both the benefits and current limitations of this feature (like the inability to share project chats), and encourage listeners to explore prompt communities such as the Facebook group AI Prompts for Entrepreneurs.
The episode wraps with sponsor messages from SelectQuote and Square, followed by a reminder to leave podcast reviews for a chance to win a MacBook. As always, the hosts sign off by encouraging listeners to “keep living that charmed life.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #655 for Casual Friday, June 6th, 2025
00:00:50 June 6th: National Donut Day
00:01:44 Dr. Julie Gurner – Look at your life this way: “If I was a stranger stepping into this person’s life, what would I change to make it better.”
The Limitless Dongle
00:07:12 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:08:46 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:10:24 AI Prompts for Entrepreneurs Facebook Group
00:11:32 Making use of ChatGPT projects…on rails
00:15:28 Business Brain 655 Outtro
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Jun 4, 2025 • 23min
Let them Cancel and Don't Make Excuses
In this episode of Business Brain, Dave Hamilton kicks things off by sharing a standout customer service experience with FMPHost, a FileMaker Pro hosting company. After years of reliable service, Dave moved his FileMaker database to a self-hosted Docker container to save costs and consolidate resources. He praised FMPHost for making cancellation incredibly easy—a rarity that left a lasting positive impression and serves as a business lesson: making it easy for customers to cancel builds long-term goodwill and trust.
Shannon and Dave then dig into the logistics of sharing FileMaker solutions with clients. Shannon wants to provide a custom database to help resellers manage inventory and profits. They explore FileMaker Cloud’s licensing model, noting it’s not cheap but may be viable if clients purchase their own licenses. The conversation evolves into an impromptu endorsement of FileMaker’s power and flexibility as a bespoke business solution.
The episode closes with Shannon’s quote of the week—“Make adjustments, not excuses”—which sparks the idea to launch a Business Brain print-on-demand merch store featuring podcast catchphrases. The duo also crowdsource tips from listeners on how to better recover from time away, with Shannon seeking advice on managing his calendar and inbox after a 12-day vacation. As always, they wrap with appreciation for the audience and a reminder to keep living the charmed life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #654 for Wednesday, June 4th, 2025
June 4th: Shopping Cart Day
00:01:12 FMPHost made our FileMaker Server Hosting cancellation simpler than ever!
00:06:55 Building and Sharing FileMaker Databases
00:12:43 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:14:18 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:15:55 Make Adjustments, Not Excuses
00:19:46 Tips for digging out after being away?
00:21:41 Business Brain 654 Outtro
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May 30, 2025 • 25min
FridAI - Priorities and Calendars
In Episode 653 of Business Brain, Dave Hamilton shares a candid story about a business deal that fell apart after 18 months of negotiations. Despite the initial disappointment, Dave felt unexpected relief—realizing that the deal would have meant giving up control of the business and taking on fixed employment terms. The failed acquisition ultimately rekindled his excitement for rolling out new projects with his partners, reinforcing the value of ownership, fast decision-making, and strategic independence.
The conversation shifts into their FridAI segment, where Shannon and Dave discuss creative ways to use ChatGPT, like uploading handwritten task lists or calendar screenshots to get time-blocking and prioritization advice. They explore the potential of multimodal inputs and structured data like ICS files to streamline decision-making and reflect on how tools like AI can be most effective after first doing the work manually to understand the process.
Shannon also discusses the rapid growth of his $5 Mastermind group, which has nearly reached 500 members. He’s adapting by blocking out structured time for introductory calls and gradually systematizing his approach. The episode wraps with a reminder about their ongoing MacBook giveaway and a call for reviews, emphasizing the importance of listener engagement and support.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #653 for Casual Friday, May 30th, 2025
May 30th: International Hug Your Cat Day
00:01:00 A deal died…and I liked it?
00:11:24 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:12:45 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!
00:14:09 Lydia Davey-FridAI idea for capturing and prioritizing client work
00:17:22 Multi-modal uses of AI
00:21:08 AI to manage your time
00:23:39 Business Brain 653 Outtro
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May 28, 2025 • 24min
Survival Entrepreneurship
In Episode 652 of Business Brain, Shannon Jean shares reflections from a recent trip to St. Lucia, highlighting the stark contrast between poverty and wealth on the island. He emphasizes how entrepreneurship there is a means of survival, with locals creatively hustling to sell everything from handmade goods to rum punch. The experience reminded him of the privilege and opportunity many in the U.S. enjoy, reinforcing the idea that success often stems from grit, simplicity, and perspective.
Shannon and Dave Hamilton explore the power of a “blue-collar mindset” in white-collar businesses—doing the hard work first before automating or delegating. They stress the importance of understanding systems manually (e.g., spreadsheets) before scaling, using examples like selling on Poshmark and building internal tools like their podcast ad scheduler.
The episode closes with a discussion on the role of AI and automation, specifically the concept of “vibe coding,” which they support—but only after you’ve done the foundational work yourself. Their message is clear: real business growth comes from a willingness to get your hands dirty, keep things simple, and always respect the hustle.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #652 for Wednesday, May 28th, 2025
May 28th: National Hamburger Day
00:01:05 Observations from your trip
The dichotomy of wealth vs. poverty
00:06:00 Entrepreneurship as a survival skill
00:10:40 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:12:02 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!
00:13:25 Applying blue collar attitudes to white collar businesses
Automation is great…but do it yourself FIRST.
Synology Office
Chase $100 Bills
Vibe Coding
00:22:54 Business Brain 652 Outtro
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May 23, 2025 • 21min
The Credibility Funnel + FridAI
In Episode 651 of Business Brain, Dave and Shannon dive into the concept of a “credibility funnel”—a precursor or complement to the traditional sales funnel. Shannon emphasizes how today’s AI tools can elevate a business’s professional image, especially through visual storytelling. He shares how he uses Napkin.ai to visualize abstract business ideas like credibility, customer service, unfair advantage, and storytelling, making complex concepts easier to communicate and more engaging for clients and newsletter readers.
They also explore AI-powered customer support, spotlighting Gumroad’s use of Helper AI to send highly relevant and personalized responses to podcast outreach. Dave praises the system’s ability to recognize context and deliver human-like interaction while being completely automated. Shannon and Dave agree that tools like these now allow small businesses to offer enterprise-level support and engagement—once impossible for solo entrepreneurs.
Finally, the episode wraps with a real-world win: Dave recounts how ChatGPT helped him recover a $37,000 IRS check by coaching him through the phone support maze during tax season. The key takeaway? Treat AI like an executive assistant—ready to guide, solve niche problems, and support your operations. Just be mindful when inputting sensitive data, especially if it involves clients or employees.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #651 for Casual Friday, May 23rd, 2025
May 23rd: National Road Trip Day
00:01:06 BB Review: voncompton
00:02:01 Before you build a sales funnel, build your credibility funnel
Business Brain 259 about Credibility Funnels
Using Napkin.AI to create your Creditbility Funnel visualization
00:08:25 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!
00:10:07 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:11:35 FridAI
FileMaker
Gumroad using Helper AI Support Agent for Instant Responses
00:17:17 I got my IRS check!
Use AI as your assistant
00:20:50 Business Brain 651 Outtro
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May 21, 2025 • 23min
You Need a 3rd Brain with Michael Greenberg – Business Brain 650
In Episode 650 of Business Brain, Dave and Shannon welcome guest Michael Greenberg from 3rd Brain to explore the essential but often overlooked world of digital operations. Michael explains that before companies dive into AI and automation, they need to establish solid foundations—clear processes, documented operations, and organized data. His firm focuses on getting businesses “AI-ready” by standardizing internal workflows, integrating tools effectively, and building a unified data structure. This strategic groundwork is crucial, especially for older, legacy businesses that haven’t evolved digitally in decades.
The conversation touches on common pitfalls, like SMBs being distracted by shiny new SaaS tools or attempting to implement tech solutions before fixing underlying operational issues. Michael urges business owners to simplify—stick to one productivity suite, create naming conventions, build templates, and focus on consistency. He also shares his approach to AI-assisted writing, where he provides structure, examples, and data, then uses AI to fill in the connective tissue—saving time but still requiring human oversight to polish.
The episode wraps with advice on productizing internal tools and resisting the temptation to overcomplicate. As Shannon and Dave reflect on their own experiences with fragmented systems and underutilized tools, they agree that standardization, clarity, and operational discipline are what allow businesses to scale effectively and avoid chaos.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #650 for Wednesday, May 21st, 2025
May 21st: International Tea Day
00:01:22 Guest Co-host: Michael Greenberg from 3rd Brain
Shannon’s Tribe Business Group on X
Third Brain provides Digital Operations (and AI and automation… just a few steps earlier)
I want to build businesses that fit an existing budget line item
00:07:11 Evolving a (family) real estate business
00:09:00 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!
00:10:44 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:12:12 Writing a book with AI
Garbage in, Garbage Out – GET YOUR DATA RIGHT
00:15:31 Simplify your business FIRST
00:19:28 Productize your internal tools
00:21:55 Business Brain 650 Outtro
Follow Michael Greenberg
3rd Brain
@gentoftech on X
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May 16, 2025 • 24min
Every Business is in the Content Business + FridAI
In Episode 649 of Business Brain, Dave and Shannon focus on the power of consistency and content creation in modern business. Kicking off with a listener email about the value of handwritten thank-you notes, they stress the importance of thoughtful outreach and relationship-building. From there, they segue into a deeper discussion on how every business is now in the content business, whether they realize it or not. Content isn’t just about marketing—it attracts clients, builds brand awareness, and even draws in potential employees.
The hosts emphasize that consistency beats quality when it comes to content performance on social media. Platforms favor creators who post regularly because it signals commitment, reducing the risk for the algorithm to promote your content. They encourage business owners to focus on one platform at a time, master it, and avoid spreading themselves too thin unless they have the team to manage engagement genuinely across multiple channels.
They also share practical advice: save every piece of content you create into a “content library,” reuse old posts as your audience grows, and use tools like Opus.pro and Loom to generate and repurpose video content. The key takeaway? Start now, even if it’s messy. Authenticity, consistency, and strategic content reuse will compound over time to grow your presence and business impact.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #649 for Casual Friday, May 16th, 2025
May 16th: National Pizza Party Day
00:01:14 David-Treat Everyone like a customer…with a handwritten note!
00:02:54 Every Business is now in the content business
00:05:35 Consistency matters more than being on the right platform.
Which platform(s) is(are) right for your business?
00:10:25 Build a content library
Social media is like a parade
00:12:12 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:13:50 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!
00:15:21 FridAI
Shannon resale video content
Opus.pro
Loom
00:17:51 Using multiple platforms (im)properly
00:21:14 Experiment with timelapse videos
00:23:50 Business Brain 649 Outtro
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May 14, 2025 • 22min
The EDU Episode
In Episode 648 of Business Brain, Dave and Shannon dive into the evolving landscape of education and its impact on entrepreneurship and the workforce. Shannon shares a conversation with a colleague who helps businesses start trade schools—not just for profit, but to solve hiring challenges. These businesses leverage trade schools to train workers in-house, tap into government retraining grants, and recruit top-performing students directly into their companies. It’s a strategic move that creates a powerful competitive advantage and highlights how alternative education models are disrupting the traditional four-year college path.
The hosts discuss the diminishing ROI of expensive college degrees and spotlight faster, more affordable ways to gain credentials, like six-month accredited programs targeted at working adults, veterans, and healthcare professionals. Dave shares personal stories, including how his son bypassed degree barriers by proving himself through an internship, and how he himself built businesses without finishing college. They agree the system is undergoing a fundamental shift, driven not by institutions but by market needs and entrepreneurial innovation.
They close by critiquing the entrenched education establishment, especially in states like California, where union influence and bloated administration hinder meaningful reform. Despite institutional resistance, Dave and Shannon remain optimistic about the role of trade schools, micro-schools, and AI-powered learning in reshaping the future of education—and opening doors for entrepreneurs to lead the way.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #648 for Wednesday, May 14th, 2025
May 14th: Root Canal Appreciation Day
00:02:24 Trade School as a recruiting tool.
00:07:37 SPONSOR: NordLayer – NordLayer is network security for modern businesses. Save up to 22% off NordLayer at NordLayer.com/brain and use code BRAIN for an extra 10% off.
00:09:14 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!
00:10:45 Backdooring College Degree Requirements
Excelsior College (online)
High School Juniors working in the trades
00:21:35 Business Brain 648 Outtro
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May 9, 2025 • 17min
FridAI - ShannonGPT + Shopify
In this FridAI episode of Business Brain, Dave and Shannon dive into the evolving future of pay-per-click advertising in a world increasingly dominated by AI tools like ChatGPT, noting how AI is replacing traditional search behavior and potentially reshaping monetization models. They discuss Shannon’s creation of a custom GPT trained on his own content to produce more personalized, on-brand outputs, and encourage listeners to build their own. Dave explores the value of upgrading to ChatGPT’s $200/month plan, including business-ready Operator features and custom GPTs for specific workflows. They also highlight promising AI-driven business ideas—like ad pitch bots and sponsorship compliance tools—before wrapping with a nod to a compelling post from Fiverr’s CEO on AI and the future of work.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #647 for Casual Friday, May 9th, 2025
May 9th: Tear The Tags Off The Mattress Day
00:01:54 n-ars56-v7v-What will happen to paid search ads now that we all use genAI?
ChatGPT adding Shopify to chat
00:06:15 Create a GPT about you!
“I want you to talk and think like I do. If I upload 100+ Word documents that I have written. Can you create a GPT and analyze what I have?”
00:09:35 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:11:10 SPONSOR: SoundSource gives you app-level audio effects and controls for any app on your Mac! Visit MacAudio.com/Brain and use code BRAIN to save 20.
00:12:30 Upgrading ChatGPT
“Given what you know about me, please give me your top 5 examples of why I would want to upgrade to the $200/month ChatGPT account. Prioritize them bringing me short-term value.”
“It seems like we might be missing something that could truly be its own business using ChatGPT Operators. Ideas?”
00:15:03 Fiverr CEO on AI
00:16:52 Business Brain 647 Outtro
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May 7, 2025 • 22min
The Agreement that Saves Partnerships
In this episode of Business Brain, Dave and Shannon dive into the value of creating a “working agreement” before starting any business partnership. They discuss how this simple, non-binding document can clarify roles, expectations, and accountability—helping partners avoid misunderstandings and preserving friendships if things don’t work out. Framed as the first true project partners tackle together, the agreement surfaces potential red flags early. Alongside this main topic, they share practical tips for product listings and legal negotiations, and reflect on homebrewing beer as both a bonding experience and an example of smart marketing.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #646 for Wednesday, May 7th, 2025
00:01:17 May 7th: National Homebrew Day
Mr. Beer
Untappd
Pinter
Quick Tips
00:05:39 Mix in client reviews and testimonials with your photos
00:07:04 When negotiating a large transaction using attorneys, make a prediction up front
“Presuasion”
00:10:23 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:11:58 SPONSOR: SoundSource gives you app-level audio effects and controls for any app on your Mac! Visit MacAudio.com/Brain and use code BRAIN to save 20.
00:13:17 Working Agreement
It’s a test!
The Friendship Clause
Heavy equipment business for toddlers!
00:20:14 Business Brain 646 Outtro
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