
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

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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Feb 14, 2025 • 21min
FridAI + Understanding Context
In this episode of Business Brain, Dave Hamilton and Shannon Jean explore the power of AI tools in transforming how entrepreneurs analyze data and streamline decision-making. Shannon shares a fascinating story about using AI to assess and value items from a liquidation auction quickly, saving hours of manual research and enabling smarter bidding strategies. Dave and Shannon discuss the importance of leveraging AI as a collaborator to organize and enhance productivity without replacing personal creativity or voice.
The conversation also dives into working with remote teams, focusing on cultural nuances and the challenge of providing clear context for tasks. They share strategies for managing expectations, avoiding micromanagement, and creating accountability between employers and their teams.
Let me know if you’d like any edits or additions!
00:00:00 Business Brain – The Entrepreneurs’ Podcast #623 for Casual Friday, February 14th, 2025
February 14th: International Winter Bike To Work Day
00:01:09 FridAI: Use ChatGPT to analyze long documents (contracts, details, product manifests)
00:05:15 FridAI: Settings > Personalization > Customize ChatGPT
“Respond with a precise, concise, and accurate tone. Focus on delivering clear and direct answers while avoiding unnecessary elaboration or repetition. Use structured formats such as bullet points, numbered lists, or short paragraphs where appropriate. Prioritize clarity and relevance, ensuring responses stay on-topic and align with the query’s intent. Tailor the explanation to be universally understandable, avoiding excessive jargon unless explicitly requested.Be opinionated and prepared to support your opinions: always state and make clear what statements are opinion and not objective fact.”
00:08:56 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!
00:10:18 Business Therapy: Context as it relates to global talent
Learn THEIR cultural norms
00:19:16 Business Brain 623 Outtro
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Feb 12, 2025 • 23min
The Hunt for Dopamine
Dave Hamilton and Shannon Jean discuss tips and strategies to stay motivated as entrepreneurs and manage tasks, including “grunt work.” They share personal tactics like breaking tasks into smaller chunks, using dopamine rewards (e.g., taking breaks, engaging in enjoyable activities), and leveraging the fear of failure to push through unappealing tasks. They highlight the importance of maintaining momentum by celebrating small wins and integrating fun tasks into the workday.
They also explore the value of building a “talent stack” by listing personal achievements and using tools like ChatGPT to identify and articulate skills. This practice helps boost confidence, foster self-promotion, and create opportunities for further growth.
Additionally, the hosts touch on themes like humility and self-promotion, encouraging listeners to showcase their accomplishments in a way that builds credibility without arrogance. They share an anecdote about David Bowie advising someone to “always make your name as big as you can” to enhance visibility and success.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #622 for Wednesday, February 12th, 2025
February 12th: National Lost Penny Day
00:01:51 RobzillaH’s Business Brain Review – Feb 10, 2025
00:03:14 What tricks do you use to keep yourself inspired to do the grunt work necessary to run your businesses?
The hunt for dopamine!
The fear of failure vs. the fear of being a failure
Rewarding yourself with a quick dopamine fix
Doomscrolling for ten minutes
Stacking work by sandwiching the grunt work between rewarding work
00:10:46 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!
00:12:08 Humility vs. Negative Self-Deprecation
Keanan Duffty on Gig Gab: “Always Make Your Name As Big As You Can”
To make it easier to talk about yourself, ask the question: What have you done? AND WRITE IT DOWN, then you can read your talent stack back to yourself.
Ask ChatGPT: “I need to create a list of my talent stack, but I’m not good at bragging. Can you create this list for me that we can collaborate on so that I can just have it and see it?”
00:22:31 Business Brain 622 Outtro
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Feb 7, 2025 • 24min
The FridAI Update - AI for the Rest of Us
In this episode of Business Brain, Dave and Shannon talk about how the internet warps our sense of success. Shannon shares how getting 15 likes on a post feels like a failure online, but if 15 people came up to you after an in-person talk, you’d feel like a rockstar. They remind listeners not to get caught up in the numbers game and to appreciate real connections, even if it’s just one person being impacted by your work. Dave brings up how they used to feel that 3,000 podcast downloads a week wasn’t much until someone pointed out that it’s like filling a huge theater every week.
They also dive into a cool side hustle idea from Shannon’s friend, Chris. Chris uses OpenAI’s $200/month operator tool to automate reaching out to people giving away free pianos on Facebook Marketplace. Instead of just picking them up for free, he offers to haul them away for $200, solving a problem for people who just want them gone. The AI handles all the messaging, and Chris barely lifts a finger. This sparks a whole conversation about how AI can simplify tasks like managing social media, scheduling, and even bidding on auction items. Shannon imagines using AI to automatically find and bid on overstock gazebos for his vacation rental.
They wrap up by talking about how doing this podcast isn’t just about teaching others—it’s also their own weekly reminder to stay motivated and improve their businesses. Both admit they’re not perfect at everything they talk about, but these conversations help them grow. They encourage listeners to leave reviews and connect with them, reminding everyone that even small interactions matter.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #621 for Casual Friday, February 7th, 2025
February 7th: National Working Naked Day
00:00:57 We get a warped perspective of being online
Narada Michael Walden at NAMM
Review Business Brain
00:09:42 FridAI – Your Weekly AI Segment
ChatGPT Operator (for $200/month)
An example of Operator in action
What happens to companies like Zapier and IFTTT?
00:20:50 Building the RIGHT inner judge for yourself
00:23:07 Business Brain 621 Outtro
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Feb 5, 2025 • 21min
The Only Constant is Change
In this episode of Business Brain, Dave and Shannon kick things off with a fun nod to National Shower with a Friend Day. They chat about the show’s upcoming 10th anniversary on February 19th and brainstorm some celebration ideas, like giveaways for listeners who submit questions or leave reviews. They’re still deciding what the prize will be, but promise it’ll be something big.
The main focus of the episode is all about embracing change in business. Shannon shares a story about a client whose product suddenly became obsolete, highlighting the importance of adapting to stay ahead. They both emphasize that if you’re not actively evolving your business, you risk falling behind. Dave draws parallels to Apple’s strategy of making their own products obsolete to stay innovative.
They also discuss their own evolution with the podcast—from calling it DBA (Doing Business As) to shifting away from frequent interviews to keep things fresh. Dave mentions how he had to adjust when his co-host left another show he runs, choosing to do solo episodes rather than scrambling for guests.
The episode wraps up with practical advice on the importance of following up in business. Dave talks about using tools like SaneBox to manage email reminders and ensure nothing slips through the cracks. Shannon likes the idea and plans to try it out. They encourage listeners to share productivity tips and, of course, leave reviews to get in on the giveaway action.
Overall, it’s a laid-back, insightful episode focused on adapting to change, staying proactive in business, and keeping things exciting for both you and your audience.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #620 for Wednesday, February 5th, 2025
February 5th: National Shower With a Friend Day
00:03:22 Change is the only constant
“The more that things change, they more they stay the same.”
Compete with yourself
Feels Like The First Time…at NAMM (on Gig Gab)
00:14:49 Always Be Following Up
SaneBox SaneRemindMe
Slack Reminders
00:20:38 Business Brain 620 Outtro
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Jan 31, 2025 • 23min
Don't Confuse the Delivery System with what You are Selling
Here’s a summary of the episode:
In this episode of Business Brain, Dave Hamilton and Shannon Jean discuss the importance of understanding what you’re truly selling, beyond just the delivery mechanism. They explore how businesses often mistake their product or service for the actual value they provide, emphasizing that customers are really looking for transformation rather than just a transaction. Shannon shares insights from his coaching business, illustrating how people may come to him for guidance on selling liquidation goods but are actually seeking financial freedom, flexibility, and independence.
Dave and Shannon also highlight how this mindset shift impacts marketing, customer relationships, and business strategy. They touch on how companies like Apple focus on the experience and benefits rather than just technical specs, and how reframing a business around transformation can lead to stronger branding and deeper customer engagement.
The conversation transitions into the power of AI tools, specifically ChatGPT’s Canvas feature, which Dave recently used to draft an executive summary and set KPIs for his businesses. He explains how AI’s objectivity provided surprising insights and helped him see his business goals more clearly. Shannon experiments with it live, reinforcing the idea that AI is an essential tool for small business owners to stay competitive. The episode wraps up with a call to action for listeners to embrace AI tools and leverage them for business growth.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #619 for Casual Friday, January 31st, 2025
January 31st: National Fun at Work Day
00:01:52 Don’t confuse what you’re selling with your delivery system
Don’t be transactional, be transformational
Learn how your customers perceive your business
Helps you understand what your customers want
Helps you pivot (if/when necessary)
Helps you with your marketing
Helps get your team behind your purpose
00:08:55 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!
00:10:14 ChatGPT’s Canvas for your Executive Summary…and lots of other things!
00:21:00 Business Brain 619 Outtro
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Jan 29, 2025 • 25min
Living Through Economic Cycles
Dave Hamilton and Shannon Jean discuss the power of free thinking and the cost of leading an uncommon life. They reflect on Dave’s experience at the NAMM conference, where a minor snub from an industry professional fueled his motivation to make a bigger impact. The conversation explores the concept of “coopetition”—collaborating with competitors for mutual growth—and how having a chip on your shoulder can drive success.
They then transition into a deeper discussion on economic cycles and business adaptability. Reflecting on past downturns (dot-com bust, 2008 recession, and COVID-19 disruptions), they highlight how advertising trends and market corrections impact business revenue. Shannon emphasizes the importance of being connected in the industry to recognize downturns early and act decisively.
Key takeaways include:
Use setbacks as fuel for future success.
Economic downturns are inevitable—prepare by diversifying income streams.
Stay informed by networking within your industry.
When business slows down, don’t panic—adapt.
Signs of economic recovery are emerging, but strategic planning is essential.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #618 for Wednesday, January 29th, 2025
00:01:02 January 29th: Freethinkers Day
00:01:49 Putting a chip on your shoulder so you can WIN
00:09:03 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!
00:10:22 Living Through Economic Cycles
Peer groups are your friends
Is your industry headed to commodity status?
00:19:13 Blaming yourself, if only to find a creative solution
When it rains, fill up your buckets
00:24:03 Business Brain 618 Outtro
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Jan 24, 2025 • 26min
The 10-Year Overnight Success
Business Brain episode 617, hosted by Dave Hamilton and Shannon Jean, covers insights on business growth, persistence, and the value of consistency.
Dave shares his experience attending the NAMM conference, a key event in the music industry, where he was invited as press due to his Gig Gab podcast. Reflecting on his journey, he emphasizes the concept of “overnight success,” taking ten years, underscoring the importance of long-term consistency in content creation. He compares this with the Business Brain podcast, which also started a decade ago, highlighting how both shows have evolved and gained industry credibility over time.
Shannon shares his own journey, crediting the podcast for helping him refine his ideas, become more comfortable discussing successes and failures, and ultimately transitioning into a content creator and business coach. He explains how consistently sharing content on X (Twitter) and experimenting with different revenue models—such as paid posts, subscriptions, digital guides, and coaching.
The discussion shifts to the power of persistence, with Shannon reflecting on a past million-dollar mistake that he once kept hidden due to shame but now uses as a learning experience for others. He highlights the importance of having the right support system, particularly his spouse, and how that helped him push forward. Both hosts discuss how consistency, data tracking, and treating content creation as a real business have contributed to their success.
The episode concludes with a teaser for next week’s discussion on differentiating between the product being sold and the delivery method used to reach customers. They encourage listeners to send feedback and leave reviews, reinforcing the value of audience engagement in their business strategy.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #617 for Casual Friday, January 24th, 2025
January 24th: Macintosh Introduction Day
Ten years to “overnight success”
Bullheaded-persistence.
Business Brain and Gig Gab
00:08:41 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!
00:10:04 Things aren’t always as they seem
Shame is a signal to talk MORE about it
Shannon’s Assignment: One page per day…and you have to share it with someone
00:17:00 Starting a business isn’t about revenue…it’s about structure and practices
Gumroad
“If you’re not in the water, you’ll never catch the wave!”
“Don’t call me lucky, I have failed more times than you have tried.”
00:25:04 Business Brain 617 Outtro
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