

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

Mar 21, 2025 • 24min
FridAI - GPT vs. Perplexity, Zoom AI and Bluesky
Business Brain episode 633 celebrates Twitter Day and discusses Blue Sky, a decentralized social network originally started as a project within Twitter by Jack Dorsey and now run by Jay Graber.
The show then moves to AI topics, emphasizing that people won’t be replaced by AI but by people who use AI. They discuss how AI has enhanced their workflow, especially with creating podcast images and using tools like Zoom’s AI summaries to generate meeting action items automatically. They also compare ChatGPT with Perplexity, noting Perplexity’s more detailed, direct answers.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #633 for Casual Friday, March 21st, 2025
March 21st: Twitter Day (also National Common Courtesy Day)
00:01:07 Lessons from Bluesky’s Jay Graber SXSW Keynote
00:11:07 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:12:32 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!
00:13:49 FridAI, the weekly AI segment
00:17:03 Zoom AI
00:20:25 Perplexity vs. ChatGPT
00:23:36 Business Brain 633 Outtro
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Mar 19, 2025 • 26min
Your Customers are Expecting to be Disappointed
In this episode of Business Brain, Dave Hamilton and Shannon Jean reflect on the unpredictable yet inspiring nature of South by Southwest and dive into two key business lessons: first, that customers today often expect to be disappointed — creating a powerful opportunity for businesses to stand out by exceeding expectations with clear communication, fast responses, and proactive service; and second, the surprising value of sabbaticals, where intentional, long-term breaks not only refresh individuals but also strengthen businesses by forcing better systems and planning.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #632 for Wednesday, March 19th, 2025
March 19th: Small Business Development Centers Day (also International Client’s Day)
00:01:09 SXSW Platinum Pass seems purpose-built for Dave
00:03:18 Customers are expecting to be disappointed.
Opportunity: Delightfully surprise your customers!
How much would you pay to get that negative review removed?
00:08:50 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:10:13 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!
00:11:31 Navigating Sabbaticals and Career Breaks — SXSW Session with Happiness Lab and DJ DiDonna
The Power of Planning Your Future Sabbatical
00:25:12 Business Brain 632 Outtro
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Mar 14, 2025 • 17min
FridAI - NotebookLM
Business Brain Podcast Episode 631 explores AI applications in business and content creation. Dave Hamilton and Shannon Jean discuss a listener’s idea to create a custom AI by uploading user manuals of all owned devices into ChatGPT, effectively turning it into a personal tech support assistant. They extend this concept to businesses, suggesting that customer service departments upload historical support tickets to train AI models, instantly improving response accuracy.
The conversation shifts to AI’s potential for content creators. Shannon considers uploading his entire written content library to an AI model for repurposing and reformatting. Dave envisions an AI tool that can be trained on personal email archives for more context-aware assistance, speculating that Google’s Gemini may soon provide such a feature.
Shannon introduces Google’s Notebook LM, an AI tool that converts written content into natural-sounding audio discussions. He explains how he uploaded a 250-page book, and the AI generated an 18-minute conversation summarizing its key points. This feature enables businesses to transform white papers, blog posts, and other text-based content into audio for easier consumption. They compare it to ChatGPT’s voice mode but highlight its passive listening benefits.
Dave shares an insight from using ChatGPT’s voice feature, emphasizing the value of delayed responses. Unlike human conversations, AI waits indefinitely, allowing users to think through responses without pressure. He notes how this improves interactions and creativity.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #631 for Casual Friday, March 14th, 2025
March 14th: Pi Day (also National Legal Assistance Day)
00:01:07 Using AI as tech support by uploading your user manuals
00:05:49 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!
00:07:26 Revisiting NotebookLM
00:12:43 Chatting with ChatGPT…don’t worry if you take some time to reply!
00:15:27 Be Polite…and considerate!
00:16:00 Business Brain 631 Outtro
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Mar 12, 2025 • 16min
Discounting Our Own Experiences
The episode of Business Brain features Dave Hamilton and Shannon Jean discussing productivity, mindset, and business strategies. They open with lighthearted Hitchcock-related jokes and discuss the unpredictable nature of the South by Southwest conference. The main discussion revolves around productivity methods, particularly the concept of a “reverse to-do list” or “to-did list,” where one focuses on what has been accomplished rather than what still needs to be done. Shannon shares his preference for using reminders instead of traditional to-do lists, explaining how he frames tasks as things he wants to do rather than has to do, which keeps him motivated.
They also discuss the power of storytelling in business and personal life, emphasizing that people are naturally interested in everyday experiences. Shannon recalls a successful newsletter he wrote that started with a humorous personal anecdote, demonstrating how relatable stories can engage audiences. Dave notes that while people often downplay their own experiences, they eagerly consume mundane details from others, as seen in social media.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #630 for Wednesday, March 12th, 2025
March 12th: National Alfred Hitchcock Day
00:03:06 Michelle Penczak’s Reverse To-Do List
00:09:23 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!
00:11:00 Discounting Your Own Experiences
00:15:39 Business Brain 630 Outtro
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Mar 7, 2025 • 19min
FridAI + Listerner Mail
Business Brain Podcast Episode 629 discusses the role of AI in learning, business, and social media strategy. The hosts, Dave Hamilton and Shannon Jean, address an email from a listener who limits their child’s AI use to encourage independent problem-solving. They compare this to past educational resistance to calculators and emphasize the importance of using AI as an assistant rather than a crutch. Dave shares a personal story about how using an early word processor for a school assignment led to a confrontation with a teacher, illustrating how technology adoption meets resistance before becoming standard practice.
Shannon shares a real-world example of using AI for business strategy. A client sought help refining their sales messaging. Shannon used Grok, X’s AI tool, to analyze the company’s social media presence and compare it with the salesperson’s posts. The AI identified a disconnect in messaging and highlighted areas for improvement. This allowed Shannon to provide detailed, data-driven feedback that led to an “aha” moment for the client.
The conversation expands into how AI can analyze successful and unsuccessful social media accounts in the same industry, providing actionable insights on engagement strategies. They discuss Grok’s ability to compare accounts and generate step-by-step plans for growth. Dave acknowledges that AI excels at processing vast amounts of data and summarizing key insights faster than humans.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #629 for Casual Friday, March 7th, 2025
March 7th: National Employee Appreciation Day
00:01:05 JHonaFalculan-Coaching AI Use in Children
00:04:21 AI and the Classroom
00:08:28 SPONSOR: Rogue Amoeba Software makes some of the best Mac Audio software on the planet, and we couldn’t produce BB this way without it! Just visit MacAudio.com/Brain and use code BRAIN to save 20% on anything they make. Download free trials, then buy online to receive the discounted price.
00:10:06 Using Grok to Get Ready for a Client Meeting
00:18:21 Business Brain 629 Outtro
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Mar 5, 2025 • 21min
Sold But Not Paid
In this episode of Business Brain, hosts Dave Hamilton and Shannon Jean dive into the challenges of balancing work and life, particularly in sales and leadership roles. They also discuss the risks of stepping away from a business while still retaining liability.
Key Takeaways:
The Dilemma of Instant Email Replies in Sales
Dave shares a real-life scenario where he responded to a client’s email over the weekend instead of waiting until Monday. They debate whether being always responsive is beneficial or if it creates an unhealthy work-life balance and unrealistic customer expectations. Shannon argues that in sales, responsiveness is crucial to success and one cannot always follow a strict work schedule. The hosts acknowledge that not all roles require 24/7 availability, and expectations should be set accordingly.
Training Employees for Responsiveness
They explore whether employees should be expected to reply instantly to emails outside work hours. Dave suggests that salespeople, in particular, must be available if they want to outperform competitors. They acknowledge that expecting constant availability could lead to burnout but recognize that customer perception matters in sales.
Should You Delay Sending Emails?
A LinkedIn user asks whether delaying email responses (e.g., scheduling them for the next morning) is a better approach. The hosts agree that for non-sales roles, delaying responses may help establish boundaries, but in sales, responding immediately often signals urgency and commitment.
The Risks of a Business Running Without You
They analyze a statement from entrepreneur Noel Halal, who argues that if a business runs entirely without its owner, it’s essentially a “silent sale” where the owner assumes all risks but sees no real reward. Dave and Shannon debate the idea, acknowledging that while delegation is essential for scaling, owners must maintain oversight to avoid financial or operational risks. They highlight the importance of structuring business ownership so that financial rewards offset the liability of stepping away.
Final Thoughts & Engagement
They encourage listeners to weigh the risks and rewards of stepping back from business operations. The hosts invite feedback from the audience on balancing business ownership and delegation. The episode concludes with a promotion for their MacBook giveaway for listeners who leave a review.
Conclusion:
The episode offers insightful perspectives on business growth, delegation, and responsiveness in sales. While being highly available benefits sales, it must be balanced with sustainability and realistic employee expectations. Additionally, business owners should carefully structure their roles to avoid assuming risks without proper compensation.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #628 for Wednesday, March 5th, 2025
March 5th: National Stop Bad Service Day
00:01:51 Working weekends…triage vs. deep work; responsive vs. reactive. Employees?
00:09:35 SPONSOR: Rogue Amoeba Software makes some of the best Mac Audio software on the planet, and we couldn’t produce BB this way without it! Just visit MacAudio.com/Brain and use code BRAIN to save 20% on anything they make. Download free trials, then buy online to receive the discounted price.
00:11:11 Would Delay-sending that email help train everyone, including you?
00:13:46 Nahuel Hilal: Did you sell your business without getting paid?
00:20:33 Business Brain 628 Outtro
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Feb 28, 2025 • 21min
FridAI and Over-Automating
In this episode of Business Brain, Dave Hamilton and Shannon Jean reflect on the highs and lows of entrepreneurship, acknowledging the emotional rollercoaster that comes with running a business. They discuss the importance of resilience and how even seasoned entrepreneurs still experience moments of doubt, only to bounce back with new energy and perspective.
The main topic of the episode focuses on the risks of over-automation. Shannon shares his philosophy of manually doing a task before automating it to fully understand the process and add a personal touch—what he calls avoiding the loss of “Dave-ness.” Dave agrees, emphasizing that starting with a manual process allows businesses to iterate and refine their systems before automating them efficiently. They share real-world examples, including how Dave’s company initially managed podcast ad placements with spreadsheets before building a custom solution, and how Shannon believes hands-on experience in business operations prevents blind spots when scaling.
In their weekly FridAI segment, Shannon introduces Napkin.ai, a tool that extracts key insights from written content and automatically generates visually appealing charts and diagrams. Dave shares a personal story of using ChatGPT to decipher his illegible handwriting from a critical business call, highlighting the importance of interacting with AI as a collaborative tool rather than expecting perfect results on the first try.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #627 for Casual Friday, February 28th, 2025
February 28th: National Chocolate Souffle Day
00:02:22 Beware of over-automating
BackBeat Media’s PodMan
Zapier
Walter Bishop from Fringe said “posit”
00:11:58 FridAI: Napkin.AI
00:14:19 ChatGPT, I can’t read my own handwriting…can you help?
Apple spending $500B on AI Servers
00:19:50 Business Brain 627 Outtro
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Feb 26, 2025 • 19min
Quitting After the First Failure
In this episode of Business Brain, Dave Hamilton and Shannon Jean discuss Levi Strauss and the origins of blue jeans, highlighting how the company pivoted from selling dry goods to revolutionizing durable workwear. They then shift to listener engagement, sharing an updated review from a long-time fan and announcing a MacBook giveaway for those who submit or update their podcast reviews.
The conversation then turns to a listener’s question about Google vs. Microsoft for business operations. Dave shares his preference for Google tools and LibreOffice over Microsoft, while Shannon desires to use both platforms less, preferring AI tools like ChatGPT and Perplexity for search. They also discuss the benefits of self-hosted cloud solutions like Synology Drive for better data control.
The episode’s main topic focuses on why many aspiring entrepreneurs give up after their first failure. Shannon emphasizes that business success is about averages and long-term profit rather than immediate wins. Dave reinforces that failure should be seen as a learning opportunity rather than an endpoint. They discuss how mindset plays a crucial role in entrepreneurial success, urging listeners to embrace adaptability and continuous learning instead of prematurely labeling efforts failures.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #626 for Wednesday, February 26th, 2025
00:01:21 February 26th: Levi Strauss Day
00:02:46 BB Review-2/24/2025
00:04:38 Patrick-Do you prefer Google or Microsoft platforms for your business?
Google Workspace
Microsoft Office
LibreOffice
Synology Drive
Zoom
00:08:55 The Importance of not stopping after the first failure
This business is about the averages…profit over time
Business Brain 626 Outtro
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Feb 21, 2025 • 21min
FridAI + New vs. Better
This episode of Business Brain explores strategies for innovation, marketing, and leveraging AI to optimize your business. Hosts Dave Hamilton and Shannon Jean discuss how businesses can stay top-of-mind with partners by regularly reaching out with valuable updates. They introduce a new system for vetting podcast sponsors, ensuring that hosts are enthusiastic about the advertisers they promote.
A key theme is the challenge of proving advertising effectiveness. They discuss the strengths and limitations of direct response marketing, using examples like Valpak mailers and Shopify ad tracking. Instead of trying to create a superior alternative to direct response, they suggest focusing on an additive approach—introducing new, different tracking methods that complement existing strategies.
The conversation also touches on business innovation, emphasizing that new ideas don’t have to be better than existing solutions; they just need to be different and worth testing. Shannon shares an example from his Apple repair business, where they positioned their aftermarket glass screens as “diamond glass,” creating differentiation even though it wasn’t better than Apple’s.
The episode also covers AI adoption in business. Dave expresses frustration with people who resist AI tools despite their advantages. He shares a story about a colleague hesitant to use AI and contrasts it with his own workflow, where he effectively uses ChatGPT to research unknown topics. He stresses that avoiding AI gives competitors an advantage and that failure to adopt new technology can limit growth.
Shannon introduces his workflow challenge—wanting AI-generated summaries before creating podcast images. Dave suggests using FlowSend, an AI tool they already use for other shows, to streamline the process.
The episode concludes with a teaser for next week’s discussion on the dangers of stopping after the first failure. They highlight how people prematurely dismiss opportunities due to early setbacks and promise to explore strategies for overcoming this mindset.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #625 for Casual Friday, February 21st, 2025
February 21st: National Sticky Bun Day
00:01:10 You don’t have to come up with something better… just different.
00:09:17 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!
00:10:30 FridAI
00:10:49 Podcast workflow
Flowsend
00:14:08 Helping people get over the AI hump
Don’t stop after your first failure…next week!
Business Brain 625 Outtro
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Feb 19, 2025 • 25min
10 Years of Business Brain
The episode celebrates the 10th anniversary of Business Brain and reflects on the challenges and lessons learned from a decade of podcasting. Dave Hamilton and Shannon Jean emphasize the importance of consistency, particularly in the face of life’s obstacles, and how having a co-host or accountability partner helps maintain momentum. They discuss how measuring success in podcasting can be challenging compared to other businesses with clearer metrics.
Dave shares a list of 10 lessons from his years in podcasting, including listening to one’s own show, maintaining a schedule, communicating effectively with co-hosts, ensuring sound quality, refining ad reads, and taking control of hosting and distribution. They also highlight the importance of promoting the show, handling criticism constructively, and evolving over time.
The conversation shifts to review, reflecting on the problematic nature of modern rating systems, where anything below a five-star rating is often perceived as a failure. Shannon shares a personal experience with a delivery service that explicitly directed customers to leave only a nine or ten, sparking a broader discussion about the value and reliability of ratings in various industries.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #624 for Wednesday, February 19th, 2025
February 19th: National Prevent Plagiarism Day
00:01:21 Lessons from ten years of podcasting
00:11:36 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!
00:12:51 BB Reviews-Feb 17, 2025
00:15:53 Linear vs. Logarithmic Review Scales
TextExpander
Grammarly
00:24:14 Business Brain 624 Outtro
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