

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

Aug 1, 2025 • 25min
FridAI. Gamma + Contract Review
In this episode of Business Brain, Dave and Shannon dive into practical AI tools that help business owners and individuals navigate modern tasks with less stress. A listener shares a clever tip for customizing ChatGPT responses by asking for links with every reply. Shannon introduces Gamma.app, a new AI platform he used to turn a pricing strategy post into a slick visual presentation—perfect for sales decks, proposals, and even one-page websites. The duo discusses how Gamma streamlines the process of turning rough content into polished, editable assets.
Dave then shares a real-world use case: reviewing a wedding venue contract using ChatGPT. Not only did the AI flag one-sided clauses, but it also helped Dave draft a more balanced alternative and even write a respectful, persuasive email to propose changes. The conversation emphasizes using AI not just for analysis, but for thoughtful, collaborative communication that protects your interests without burning bridges. They wrap up the show with a call for listeners to send in their own AI discoveries—because every tool that sharpens your business brain helps you keep living that charmed life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #671 for Casual FridAI, August 1st, 2025
August 1st: Start Up Day Across America
00:01:09 Jim-QT-Tell ChatGPT/Perplexity/Gemini/Claude to cite 3 sources for every answer
“Every answer should come with at least 3 links to source pages I can click on to read more.”
00:03:11 Gamma AI
Shannon’s Whistle, Workhorse, and Whale Example on Gamma App
00:08:28 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!
00:09:58 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!
00:11:46 Reviewing Contracts…and proposing the way to communicate your changes.
00:23:59 Business Brain 671 Outtro
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Jul 30, 2025 • 23min
Booze and Texting - But not what you think
Today on Business Brain, Shannon kicks things off with a brisket victory, reminding us that even after years of doing something, there’s always a new layer to learn—an insight that mirrors business growth. Dave shares a health update, revealing he was battling Lyme disease but managed to travel and speak at a conference while choosing not to drink alcohol. This sparks a conversation on how business functions often revolve around alcohol, and how having a few easy, non-confrontational reasons ready can help you gracefully opt out without judgment or awkwardness. The duo dives into how our relationship with alcohol evolves over time and how staying clear-headed can unlock unexpected advantages during networking events.
They also riff on how communication styles differ dramatically between in-person conversations and written messages. Shannon argues that written communication requires a more expressive approach—adding exclamation points, emojis, or personalized phrasing—to compensate for the lack of tone and body language. They discuss the importance of crafting automated messages with personality and branding (even down to using the same emoji in every newsletter). Dave highlights how ChatGPT helps him trim wordy emails, and they close out by urging listeners to reflect on how their employees communicate, and whether tools like templates or auto-responders help or hurt clarity.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #670 for Wednesday, July 30th, 2025
July 30th: World Snorkeling Day
00:01:00 You never stop learning!
00:02:49 Talk about not drinking on business trips
“Drunk words are sober thoughts.”
Shared crisis
Actually listening
DUBS Passive Earplugs
00:14:03 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!
00:15:34 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!
00:17:10 Differentiating yourself with text vs. phone
00:23:00 Business Brain 670 Outtro
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Jul 25, 2025 • 20min
FridAI - Surrounded by Agents.
In this episode of Business Brain, Dave Hamilton and Shannon Jean dive into the new agent abilities being rolled out by ChatGPT. These agents go beyond basic chatting, allowing users to automate tasks like managing emails, calendars, messages, reservations, and even moderating communities across platforms like Slack and Discord. They discuss the potential of these features, which are being gradually released to paid ChatGPT users, and how they might streamline daily business operations. Shannon shares how he’s particularly excited about applying these tools to his community and content workflows, while Dave explores how agent mode will work through desktop apps for broader system integration.
The hosts also reflect on their long-term use of ChatGPT as a business consultant and even for personal matters like health concerns, emphasizing its value as an objective tool not influenced by human bias. They contrast this to how traditional professionals like doctors rely on personal experience, which can sometimes cloud judgment. Both hosts touch on the broader vision of using AI to preserve their insights and experiences for future generations, envisioning a digital legacy that family members could someday interact with.
The conversation wraps with thoughtful commentary on the implications of legacy, mortality, and generational knowledge transfer. Shannon and Dave muse about how human progress is shaped by generational resets, yet there is enduring value in archiving stories and lessons. They close by inviting listeners to share how they’re using agents in their own businesses and promoting a giveaway for Business Brain reviewers.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #669 for Casual Friday, July 25th, 2025
July 25th: International Red Shoe Day
00:01:18 ChatGPT Agents
00:06:58 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
00:08:42 ChatGPT as a consultant…it’s not biased by experience.
00:12:52 Agent ideas…and life, longevity, and legacies!
00:19:14 Business Brain 669 Outtro
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Jul 23, 2025 • 21min
What are We Working for?
In this episode of Business Brain, Shannon Jean shares a powerful metaphor that guides his work and life: the campfire. For him, success is about creating meaningful experiences and connections with loved ones—gathering around a campfire at his river house, watching his family enjoy the space he built through years of hard work. It’s a symbol of why he grinds day in and day out. He encourages listeners to find their own metaphor or “noble cause” that drives them beyond the daily hustle—to build a life that pulls them forward with purpose.
Dave Hamilton reflects on his recent health scare—diagnosed with Lyme disease—and how it forced him to slow down, reprioritize, and only focus on the most important work. That experience helped him realize how much of his time had been consumed by nonessential tasks, and that some things don’t fall apart when you step back. He shares how delegating or even automating B-level tasks (with the help of new tools like ChatGPT agents) could help entrepreneurs focus more on their A-level priorities and live their version of a charmed life.
Together, they challenge listeners to define their own “charmed life” and identify the signs they’re already living it. Whether it’s a campfire, a podcast studio, or something entirely different, the point is to use that vision to create purpose and joy in your entrepreneurial journey.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #668 for Wednesday, July 23rd, 2025
July 23rd: International Yada Yada Day
00:01:40 This is why we work
Shannon’s Campfire Metaphor…what’s yours?
What’s your noble cause?
00:08:39 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
00:10:22 Dave’s recent health issue leads to learning…
00:13:14 Value of forced prioritization
00:18:18 How does your charmed life manifest itself in how you live your life?
00:20:12 Business Brain 668 Outtro
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Jul 18, 2025 • 19min
FridAI with Non-Typical GPT and Voice Mode – Business Brain 667
In this episode of Business Brain, Shannon Jean and Dave Hamilton explore the unique and advanced ways they’ve been using ChatGPT, far beyond typical applications. Shannon shares how he uses ChatGPT to build and run his reseller mastermind community—developing branding, member agreements, swag, engagement strategies, and more. He also discusses leveraging AI to analyze hundreds of coaching call transcripts, extracting insights, emotional patterns, and frameworks to build scalable systems and codify intellectual property.
Dave shares how he uses ChatGPT for more technical purposes, like building a custom Cloudflare worker for anonymized tracking and for deeply contextual health troubleshooting—using it alongside his doctor to track symptoms and narrow down diagnoses. Both hosts emphasize the power of ChatGPT’s multimodal abilities, like converting images or PDFs into editable text and syncing disparate data sources.
They close with a discussion about the rising value of voice-mode interactions with ChatGPT, noting how it has replaced much of their Google searching. The duo also teases a future episode on SEO for AI-based search, suggesting that businesses need to adapt as AI changes the digital landscape.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #667 for Casual Friday, July 18th, 2025
July 16th: World Listening Day
00:01:15 ChatGPT, tell me something unique that I have used ChatGPT for that is different than a typical user
00:07:41 SPONSOR: Constant Contact makes marketing easier and more effective for small businesses like yours. Try Constant Contact free for 30 days at ConstantContact.com
00:09:16 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!
00:10:51 Dane Vahey-ChatGPT use cases
ChatGPT in Chrome search
Editable text from PDFs/images
00:14:30 Using ChatGPT’s voice mode
00:18:42 Business Brain 667 Outtro
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Jul 16, 2025 • 21min
Nick Hancock from Direct Outlet Mattresses
In this episode of Business Brain, Dave and Shannon welcome guest Nick Hancock from Direct Outlet Mattresses. Nick shares his journey from working a 9-to-5 job he disliked to diving into his family’s multi-generational mattress business. After getting fired from his previous job, he embraced the mattress world with the help of his father and brother. Now based in Charlotte, Nick explains how he’s grown his business beyond traditional retail by leveraging social media — especially X (formerly Twitter) — to connect with customers and drive national sales.
Nick emphasizes the power of authentic storytelling and personal branding in building trust and generating business. By sharing real-life moments and insights into his daily work, he’s developed a loyal online following and turned seemingly mundane mattress content into engaging posts that drive results, including hotel and Airbnb deals. He stresses the importance of content, particularly video, and plans to scale his business further through digital channels, rather than expanding physical stores.
The episode wraps with a discussion about customer service in the mattress business, Nick’s in-store “comfort test” strategy to reduce returns, mattress longevity tips, and how changing habits — even what side of the bed you sleep on — can be beneficial. Nick’s story showcases how consistency, transparency, and leaning into content creation can elevate any business, even one as traditionally “boring” as mattresses.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #666 for Wednesday, July 16th, 2025
July 16th: National Hot Dog Day
00:01:47 Guest Co-host: Nick Hancock from Direct Outlet Mattresses
Dad started the mattress business
Nick got fired (from a different job), Covid hit, and Nick decided to learn the mattress business
00:03:53 The value of working elsewhere before joining the family business.
00:05:14 Being The Mattress Guy on X
00:08:19 SPONSOR: Constant Contact makes marketing easier and more effective for small businesses like yours. Try Constant Contact free for 30 days at ConstantContact.com
00:09:54 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!
00:11:28 With mattresses, it pays to slow down and encourage the customer to choose the right mattress.
Don’t just rush to a sale
00:13:45 Care for your mattress
Rotate it 180-degrees every 3 months
If you have a king mattress you can rotate it 90-degrees if you’re ok with it occasionally being 5” shorter
00:16:38 What’s next?
Rolling out eCommerce
00:18:49 Social Media driving business sales isn’t new…at all!
00:20:25 Business Brain 666 Outtro
Follow Nick Hancock
The Mattress Guy on X
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Jul 11, 2025 • 18min
FridAI with GPT Bank and Credit and Suno Music
In this lively FridAI episode of Business Brain, Dave Hamilton and Shannon Jean dive into personal experiments with AI tools. Shannon shares how he used AI to analyze his credit card and bank statements, uncovering surprising expenses like $1,143 spent on SaaS subscriptions and nearly $700 on Amazon. He discusses how he’s using AI tools like ChatGPT and Replit to create more efficient systems and audit his finances, even replacing paid services like FreshBooks. The hosts also explore the potential of AI agents for canceling unused subscriptions and discuss privacy considerations around sharing financial data with AI.
The conversation then shifts to creative uses of AI. Dave plays a country song he created using the AI music generator Suno, using only a single line of text as the hook. They talk about how tools like Suno help quickly flesh out creative ideas and iterate on them. The song’s hook, “The beer made it better for a minute,” sparks laughter and even a potential t-shirt idea.
The episode wraps with sponsor messages and an open invitation for listeners to share how they’re using AI. Whether it’s for productivity or creativity, Dave and Shannon highlight the power of these tools to simplify life and business — while always keeping things fun and engaging.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #665 for Casual Friday, July 11th, 2025
July 11th: World Kebab Day
00:01:30 Writing songs with Suno AI
00:02:10 Uploading your bank and credit card statements to ChatGPT
00:09:32 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
00:11:11 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!
00:13:00 Writing songs with Suno AI
“Beer Made It Better…For a Minute”
Business Brain 665 Outtro
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Jul 9, 2025 • 20min
Energy and Experience – Business Brain 664
In this episode of Business Brain, Dave and Shannon kick off by reflecting on their July 4th holiday weekends before diving into an engaging conversation about energy, connection, and entrepreneurship. Shannon shares insights from over 140 discovery calls he’s had with members of his $5 mastermind, emphasizing the surprising value he receives from these conversations — particularly a standout call with a driven 19-year-old entrepreneur named Cooper. The two discuss how meaningful connection, especially in a remote work world, can energize and inspire, helping entrepreneurs stay motivated and purposeful.
They explore the importance of storytelling in business, with Shannon encouraging his coaching clients to leverage their personal motivations — such as supporting family or contributing to their communities — in their brand narratives. This authenticity, he argues, builds trust and differentiation. The duo also revisits the concept of “selling the transformation, not the transaction,” using the Michelin brothers as a prime example. Rather than marketing tires, Michelin promoted travel and experience, which in turn created more demand for their product.
The episode wraps with a nod to the show’s sponsors and a reminder to entrepreneurs to sell the outcome their product or service provides, not just the item itself. Dave and Shannon encourage listeners to think about how they can market the experience their business creates — a strategy that can be both more compelling and more rewarding.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #664 for Wednesday, July 9th, 2025
July 9th: National Don’t Put All Your Eggs In One Omelet Day
00:01:57 The energy of connecting with people
00:10:28 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
00:12:08 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!
00:13:45 Selling the experience, not the product
Founders Podcast (and their episode about the Michelin Brothers)
Sell the transformation, not the transaction
00:19:06 Business Brain 664 Outtro
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Jul 4, 2025 • 20min
FridAI - Replit + CoPilot
In this Independence Day episode of Business Brain, Dave and Shannon kick things off by reflecting on unbirthdays, reviews from their listeners, and the continued popularity of their “FridAI” episodes. They emphasize the value of experimentation and how the show has evolved over time to stay fresh and relevant for both themselves and their audience.
The duo then dive into practical tools to boost productivity. Dave shares tips on using the ChatGPT desktop app for deep integration with Mac apps, allowing users to streamline work by sharing files and leveraging app-aware functionality. Shannon introduces Replit, a no-code AI coding tool he used to build a custom financial dashboard. He explains how he walked through the process—describing what he wanted and letting Replit generate a working web app to categorize business income and expenses simply by forwarding emails.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #663 for Casual Friday, July 4th, 2025
00:01:33 July 4th: Alice In Wonderland Day
00:02:28 BB Review-WeRPID-A Must-Listen for Anyone with a Growth Mindset
00:04:25 BB Review-FirstInTheRace-5-Stars
00:05:23 Experiment with your business to keep things fresh for you and your customers
00:06:10 Do you use the ChatGPT Desktop App?
VS Code with CoPilot
00:08:16 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:09:41 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!
00:11:28 Replit
00:18:55 Business Brain 663 Outtro
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Jul 2, 2025 • 22min
Fear of the Unknown + Fever Dreams
In this episode of Business Brain, Dave Hamilton and Shannon Jean kick off with a candid conversation about Dave’s recent illness, which includes an unexplained fever and persistent headache. Despite being under the weather, Dave emphasizes the importance of consistency and leadership, especially when managing a growing business. He discusses the challenges of maintaining productivity while sick, using tools like Loom to create SOPs and keep his team aligned as they evolve internal systems at Backbeat.
The hosts also explore the topic of decision-making and fear in business. They stress the value of empowering employees to act independently, even if the decisions aren’t perfect, and highlight the power of curiosity to overcome fear. Shannon shares how reframing risk-taking as experimentation helps mitigate fear of the unknown, and recounts how a failed software venture taught him valuable lessons that led to writing a successful book.
Finally, they reflect on the psychological differences between fear of failure and fear of being perceived as a failure. They encourage listeners to embrace action, share their own fears and insights, and participate in the community through reviews and feedback. The episode blends vulnerability, leadership strategy, and personal growth, all with their signature enthusiasm.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #662 for Wednesday, July 2nd, 2025
July 2nd: World UFO Day
00:01:35 Fever Dreams and Your Business
Loom to train *and* create SOPs
00:11:37 SPONSOR: Square. Get up to $200 off Square hardware when you sign up at square.com/go/brain #squarepod #ad
00:13:02 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!
00:14:53 Managing Fear
The main source of fear is the fear of the unknown
Will this work? Feed your curiosity.
“Failure gives you data, fear gives you excuses.”
00:20:19 Fear of failure or fear of being a failure?
00:21:26 Business Brain 662 Outtro
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