

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

Jun 27, 2025 • 20min
FridAI with Delphi, ChatGPT and Perplexity
In this Casual Friday episode of Business Brain, Dave and Shannon dive into a discussion about Delphi.ai, a tool designed to create a persistent, AI-powered version of your knowledge and insights. Shannon shares his plan to test Delphi by uploading transcripts from his coaching sessions to develop an AI assistant that can respond to client questions in his voice and style. The goal is to increase responsiveness in his Slack community and free up time by allowing AI to handle frequently asked questions—particularly for his reseller mastermind group. They discuss the potential of such tech to scale personalized advice without always being present.
The conversation then pivots to a comparison of ChatGPT and Perplexity, where Dave explains his frustrations with ChatGPT’s tendency to “people-please” and its limitations in long, complex sessions. He finds Perplexity to be more accurate and less prone to misdirection in search queries, especially for coding and in-depth questions. The episode also includes glowing listener reviews and a reminder about their MacBook giveaway. Ultimately, the show highlights the evolving landscape of AI tools for entrepreneurs and encourages experimentation while remaining mindful of risks and limitations.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #661 for Casual Friday, June 27th, 2025
June 27th: National Food Truck Day
00:01:35 Delphi.AI
00:08:58 SPONSOR: OpenPhone is the #1 business phone system that streamlines and scales your customer communications. Get 20% off your first 6 months at OpenPhone.com/BusinessBrain
00:10:33 SPONSOR: Eversite – Your own in-house web team for just $399/month. No big upfront fees, no long-term contracts—just a gorgeous, pro-managed website without the stress. Visit Eversite.com/bb to get started today!
00:12:28 Perplexity might be a better search engine replacement than ChatGPT
00:17:33 BB Review-5 Stars-EnricoLimcaco
00:18:29 BB Review-KingDave22-A Higher Level Show for Higher Level Business Owners
00:19:30 Business Brain 661 Outtro
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Jun 25, 2025 • 21min
Overnight Success + Patience is a Currency
In this episode of Business Brain, Dave and Shannon pay tribute to Fred Smith, the founder of FedEx, highlighting his pivotal role in the development of overnight shipping. They share the legendary story of Smith gambling FedEx’s last cash in Las Vegas to make payroll, a gamble that ultimately kept the company alive. Shannon recounts his own entrepreneurial journey, including how he tried to partner with FedEx and eventually succeeded with DHL to implement a nationwide laptop repair pickup system. This move transformed his business from local to national, demonstrating how persistence and creative problem-solving can yield massive results.
The hosts then shift to a discussion on patience as a critical “currency” in business. Dave reflects on how patience, much like money or time, can be invested to build lasting relationships and trust—especially in sales, customer service, and startup growth. Shannon reinforces the idea by sharing how patience helped sustain their podcast until it became sponsor-worthy and scalable. They both stress the importance of sticking with a long-term vision, resisting the temptation for fast success, and staying positive—even when progress is slow. The episode closes with an encouragement for listeners to keep showing up, ask smart questions, and be patient with outcomes.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #660 for Wednesday, June 25th, 2025
June 25th: Global Beatles Day
00:01:31 Fedex’s Fred Smith passed away
Fred Smith made payroll…with blackjack!
PowerBookResQ partnered with DHL for Same Day Pickups
00:09:10 SPONSOR: OpenPhone is the #1 business phone system that streamlines and scales your customer communications. Get 20% off your first 6 months at OpenPhone.com/BusinessBrain
00:10:44 SPONSOR: Eversite – Your own in-house web team for just $399/month. No big upfront fees, no long-term contracts—just a gorgeous, pro-managed website without the stress. Visit Eversite.com/bb to get started today!
00:12:38 Patience is a currency
00:19:56 Business Brain 660 Outtro
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Jun 20, 2025 • 19min
FridAI – Granola AI + LifeGPT – Business Brain 659
Want to live your Charmed Life? Then start using AI like your personal CFO. In this week’s episode of Business Brain, Shannon and Dave explore how to feed your business and personal finances into tools like ChatGPT to uncover waste, optimize spending, and build smarter systems—without relying on spreadsheets or budgeting apps. Think of it as hiring a ruthless, data-loving advisor who doesn’t sleep. They also cover tools like Granola.ai that help you record, summarize, and learn from meetings so you can sharpen your messaging and become a better closer.
You’ll learn how capturing and analyzing your data—everything from transcripts to bank statements—can help you build better habits, fine-tune your systems, and grow your revenue. The magic isn’t in working harder; it’s in working smarter with the help of powerful AI tools that are finally accessible to all of us. If you’re trying to scale, coach, or just stay organized in a sea of digital noise, now’s the time to pattern match your way to success.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #659 for Casual Friday, June 20th, 2025
June 20th: World Productivity Day
00:01:30 CopyPrompts on Threads-Let ChatGPT budget for you
00:04:42 Using ChatGPT as your medical triage assistant
00:06:15 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!
00:07:45 SPONSOR: Eversite – Your own in-house web team for just $399/month. No big upfront fees, no long-term contracts—just a gorgeous, pro-managed website without the stress. Visit Eversite.com/bb to get started today!
00:09:43 Granola AI
Inviting ChatGPT to know as much as it can about you
AI used to be called Machine Learning, and ML used to be called Pattern Matching. This stuff has been used to target advertising to you for a long time.
00:18:22 Business Brain 659 Outtro
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Jun 18, 2025 • 22min
You Need Patience More Than Money
You’re building a business—but are you being too impatient? This week on Business Brain, Shannon and Dave dive into why patience often trumps money in the early stages of entrepreneurship. Instead of chasing quick profits, focus on putting in reps, learning the game, and building a system that pays off long-term. You’ll hear how to stay grounded during those “grind now, profit later” phases, and why a strong foundation is your best shot at sustainable success. If you’re flipping products, launching a service, or just pivoting, the secret isn’t more cash—it’s more time, more process, and more clarity.
They also unpack the power of transparency in partnerships. Want to make smarter decisions with your co-founders? Try laying your cards on the table—real talk about personal cash needs can shift everything. Shannon shares how keeping expenses lean gives you maneuverability, while Dave reveals how his team shared their personal budgets to boost trust and empathy. It’s all about knowing what you really need, so you can stop panicking and start living your Charmed Life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #658 for Wednesday, June 18th, 2025
June 18th: International Panic Day (and International Picnic Day)
00:02:44 BB 5-Star Review-Jeremy Luebke-Just the facts ma’am
00:03:20 BB Review-4 Stars-A Different Perspective
00:04:03 BB Review-Dave-5/5 Podcast
00:04:43 Quick Tip: Mix screenshots of your reviews in with your product images
00:07:27 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!
00:08:58 SPONSOR: Eversite – Your own in-house web team for just $399/month. No big upfront fees, no long-term contracts—just a gorgeous, pro-managed website without the stress. Visit Eversite.com/bb to get started today!
00:10:55 You need patience more than money
“I need time more than I need money.”
An experiment: Sharing your monthly expenses amongst your partners.
00:20:19 Business Brain 658 Outtro
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Jun 13, 2025 • 19min
FridAI - Gmail and Calendar Takeover
In this Business Brain episode, Dave Hamilton celebrates the 20th anniversary of his first podcast, Mac Geek Gab, reflecting on how a direct email to Steve Jobs led to Apple featuring his show on the launch day of their iTunes podcast directory. This moment serves as a springboard for a broader discussion with Shannon Jean about the importance of building relationships with decision-makers early—before you need them. Shannon shares a similar story from his time selling on Poshmark, where connecting with the company’s executives via LinkedIn eventually led to major promotional support. The takeaway: establish valuable connections in advance, and don’t hesitate to reach out directly—it’s often the “third door” to opportunity.
The second half dives into emerging uses of AI as personal assistants. Shannon shares a powerful case study from Nick Hulinski, who uses Claude (an AI model) to streamline his calendar, email, and weekly planning—essentially replacing the need for a human assistant. Dave and Shannon express interest in building a similar setup and lament Apple’s slower pace of integrating these AI tools in a privacy-conscious way. They also touch on how tools like Claude and ChatGPT are helping users build personal operating systems and frameworks for decision-making. The episode wraps with an invitation to connect, watch the live stream, and engage with the hosts directly through LinkedIn or email.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #657 for Casual Friday, June 13th, 2025
June 13th: National Productive Business Civility Day
00:01:10 It was 20 years ago today…Dave launched his first podcast!
Want a Steve Jobs story? Press play!
00:08:44 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!
00:10:11 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.
00:11:54 Claude fixed @CoFoundersNik’s Chaos
Connect Gmail to Claude
00:18:30 Business Brain 657 Outtro
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Jun 11, 2025 • 15min
I Need Time More Than I Need Money – Business Brain 656
In this episode of Business Brain, Shannon Jean kicks off the discussion by highlighting the importance of experimentation through a simple product called the Brain Press—a tactile fidget toy created by a fellow entrepreneur he follows on X. The segment uses the Brain Press as a springboard to emphasize the entrepreneurial value of trying new things, escaping the daily grind, and executing on small ideas just to see what happens. Shannon celebrates the mindset of building and testing, citing inspiration from others who create and launch products annually as passion projects or side hustles.
Dave Hamilton follows with a story about helping a client with a tech issue, which leads to a reflection on valuing time over money. Even when money was tight, Dave always focused on completing jobs efficiently rather than billing for more hours. Both hosts agree that this mindset builds trust with clients and fosters personal efficiency. The conversation ends with a mutual acknowledgment of how future-focused thinking helps them move quickly through tasks, maintain momentum, and ultimately live a “charmed life.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #656 for Wednesday, June 11th, 2025
June 11th: National German Chocolate Cake Day
Brain Press
00:05:28 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!
00:06:54 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.
00:08:16 The value of having an “I need time more than I need money” attitude, even when that’s not true.
00:14:49 Business Brain 656 Outtro
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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
Discover the stark contrasts of wealth and poverty in St. Lucia, where locals rely on entrepreneurship as a vital survival skill. Hear how a blue-collar mindset can elevate white-collar businesses and the importance of manual understanding before automating tasks. The hosts stress that true growth comes from hard work and maintaining simplicity in business. They also discuss how AI and automation should come only after mastering the basics, highlighting the need to respect the hustle in any entrepreneurial journey.