
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

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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The post FridAI – ShannonGPT + Shopify – Business Brain 647 appeared first on Business Brain - The Entrepreneurs' Podcast.

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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May 2, 2025 • 21min
Strategy is Choosing What Not to Do + FridAI
In this episode of Business Brain, Dave and Shannon dive into a mix of tech, strategy, and entrepreneurship insights. They discuss the mental exhaustion of constant video calls, particularly the unnatural experience of seeing oneself too often on Zoom.
They explore the idea that strategy is about choosing what not to do, referencing Steve Jobs’ approach at Apple and emphasizing the power of saying no to maintain focus and effectiveness. Shannon and Dave reflect on how early-stage entrepreneurs often say yes to everything out of necessity, but that maturing businesses must learn to prioritize.
They transition into how ChatGPT helps overcome decision paralysis and speeds up problem-solving, from renaming podcasts to fixing irrigation issues. Shannon shares how ChatGPT accurately diagnosed a sprinkler issue in seconds—something that would’ve taken hours or days otherwise. Both hosts agree that ChatGPT has become significantly more reliable, especially for tech support, but still has limitations and occasional false promises (like pretending it can generate Canva links).
Shannon introduces a new tool, typeset.com, for creating professional e-books and presentations. He used it with ChatGPT to develop a lead magnet for a client and found it valuable for enhancing visual content. They close by inviting listeners to share their favorite AI tools and reminding them to leave a review for a chance to win a MacBook.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #645 for Casual Friday, May 2nd, 2025
May 2nd: International Scurvy Awareness Day (also National Truffle Day?)
00:01:33 Watching ourselves on our own screens is distracting
00:05:35 Strategy is choosing what NOT to do
Guy Kawasaki with Debbie Millman
00:09:37 SPONSOR: Insta360 X5 Camera. To bag a free invisible selfie stick worth US$24.99 with your X5 purchase, head to store.insta360.com and use the promo code “brain”, available for the first 30 purchases only.
00:11:27 Using ChatGPT to rename Mac Geek Gab
From “Mac Geek Gab — Your Questions Answered, Tips Shared, Troubleshooting Assistance” to “Mac Geek Gab — Apple Tips, Tricks, and Troubleshooting”
00:13:25 Using ChatGPT for tech support can be great
00:17:00 But it also lies…
00:18:16 Typeset.com
00:20:25 Business Brain 645 Outtro
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Apr 30, 2025 • 20min
Leveraging your ADHD Superpower
In this episode of Business Brain, Dave and Shannon discuss how traits associated with ADHD—like jumping between ideas, hyper-focus, and high risk tolerance—can actually serve as superpowers for entrepreneurs.
They share personal experiences, acknowledge their unofficial ADHD diagnoses, and talk about learning to manage it through strategies like using ChatGPT, listening to music, or delegating tasks they’re not strong at, like accounting.
Shannon emphasizes that ADHD traits such as creativity, rapid idea connection, and risk tolerance can fuel innovation and success. Dave stresses the importance of learning to live with oneself and leveraging hyper-focus intentionally.
They also highlight the downside of imposter syndrome, arguing that true imposters don’t experience it—only the self-aware do. The show ends with a conversation about the power of quiet confidence in business, the downside of trying too hard or appearing desperate, and the value of letting results speak for themselves.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #644 for Wednesday, April 30th, 2025
April 30th: International Jazz Day
00:01:30 Shannon uses Insta360’s webcam
00:01:58 Leveraging your ADHD superpowers
Hyperfocus
Distractibility
Reality Distortion (in a positive way)
Pomodoro Method on Business Brain
00:13:27 SPONSOR: Insta360 X5 Camera. To bag a free invisible selfie stick worth US$24.99 with your X5 purchase, head to store.insta360.com and use the promo code “brain”, available for the first 30 purchases only.
00:15:16 The act of trying too hard is a sign of weakness
The real imposters never experience the syndrome
Quiet confidence vs. cockiness
00:19:33 Business Brain 644 Outtro
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Apr 25, 2025 • 24min
FridAI + The 3rd Door
In this episode of Business Brain, Dave Hamilton shares a story about a $36,000 IRS refund check he mailed to his bank, which never arrived. After frustrating interactions with Citibank and the IRS, he turned to ChatGPT for help. ChatGPT guided him to use the IRS Practitioner Priority Line and the Taxpayer Advocate Service, ultimately helping him start a trace on the missing check—something that could have taken months longer without AI’s assistance. Dave emphasizes how AI can dramatically improve efficiency and help with bureaucratic challenges.
Shannon Jean then shares a concept called the “third door”—a strategy for building relationships with key people before you need them. He recounts how he used LinkedIn to connect with eBay and Poshmark executives, establishing trust over time. These early, genuine connections later opened doors to speaking opportunities and support when problems arose. He encourages listeners to build relationships early by offering value and engaging authentically, without immediately asking for favors.
The episode also includes sponsor messages for Shopify and Insta360 and wraps with a call for listeners to connect on LinkedIn and share their own “third door” stories. The overarching message: use smart tools like AI and strategic relationship-building to live a more successful, charmed entrepreneurial life.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #643 for Casual Friday, April 25th, 2025
April 25th: International Financial Independence Awareness Day
FridAI
00:01:07 ChatGPT Taught me How to Solve my Problem Calling the IRS
00:11:09 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!
00:12:41 SPONSOR: Insta360 X5 Camera. To bag a free invisible selfie stick worth US$24.99 with your purchase, head to store.insta360.com and use the promo code “brain”, available for the first 30 purchases only.
00:14:11 Find the Third Door
LinkedIn
Rebecca Michals, eBay Director of Community on Business Brain
00:21:39 If You Want More, Do More
00:23:12 Business Brain 643 Outtro
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Apr 23, 2025 • 25min
The 20/80 Opportunity
In this episode of Business Brain, Shannon introduces a new concept called the 20-80 Rule, a twist on the traditional 80/20 principle. His version suggests that investing two years of hard work upfront—building systems, making mistakes, and laying a solid foundation—can result in eight years of sustained revenue and business growth. He emphasizes patience, long-term thinking, and warns against the illusion of quick success.
Dave reinforces this idea with a story about launching Mac Observer in 1998, explaining how it took nearly two years to become sustainable, and highlighting the importance of building strong systems early to support future growth.
The hosts also dive into the idea of “coopetition”—collaborating with competitors to create mutually beneficial opportunities. Dave shares how BackBeat Media was born after competitors asked for help with hosting and ad sales. Shannon echoes the sentiment, recalling how sharing large product deals early in his career led to reciprocal opportunities down the line.
They criticize the scarcity mindset and the tendency of some business owners to guard information out of fear, arguing that execution and collaboration matter far more than secrecy. The episode closes with encouragement to share ideas, build in public, and seek partnerships instead of isolation.
Listeners are invited to share their thoughts on the 20-80 Rule and coopetition at feedback@businessbrain.show.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #642 for Wednesday, April 23rd, 2025
April 23rd: National Email Day
00:01:21 The 20/80 Rule
00:09:39 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!
00:11:08 SPONSOR: Insta360 X5 Camera. To bag a free invisible selfie stick worth US$24.99 with your purchase, head to store.insta360.com and use the promo code “brain”, available for the first 30 purchases only.
00:12:40 Prioritize Coopetition
The pie is infinite!
Apple SuperDrive
00:24:00 Business Brain 642 Outtro
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Apr 18, 2025 • 23min
FridAI - Prompts and Blind Spots
An AI update from the hosts of the Business Brain podcast. Two powerful prompts to keep you from being left behind and a prompt to analyze your blind spots. Join us!
00:00:00 Business Brain – The Entrepreneurs’ Podcast #641 for Casual Friday, April 18th, 2025
April 18th: Lineman Appreciation Day
00:02:34 America Turner-Use AI to help you learn to use AI
“I work in [insert your field]. I’ve made a career as a [insert your job title]. How will AI disrupt my progress, and what skills will it replace?”, then…
“What can I do in the next 6, 12, or 18 months to use AI to grow my career?”
00:05:49 AI Voice is Patient
00:08:39 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:09:44 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!
00:10:57 ChatGPT now lets you reference chat histories
“Now that you can remember everything I’ve ever typed here, point out my top five blind spots.”
Die With Zero
00:22:23 Business Brain 641 Outtro
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Apr 16, 2025 • 25min
Collin Rutherford of Founder Brands
Colin Rutherford joins the Business Brain podcast to share his entrepreneurial journey. Starting as a Division I hockey player at Dartmouth, he launched Greenbox Storage, a summer storage service for college students. Despite balancing 30 hours a week of hockey and Ivy League academics, he learned critical time management skills and grew the business to 23 schools. He discusses the challenges of scaling too fast—tripling branches in a year led to losses at multiple locations, teaching him the importance of measured growth and profit focus.
Colin also talks about going viral on X with a post that reached 62 million views, which helped him monetize and gain visibility. He emphasizes consistency, experimentation, and borrowing proven strategies from others as keys to growing on social media. He’s posted over 18,000 times and follows a strategy influenced by Justin Welsh’s content model.
Colin now runs Greenbox Storage and Founder Brands, a digital marketing and personal branding agency helping entrepreneurs grow their online influence. He highlights the importance of building a great remote team and using tools like Google Workspace, Slack, and AI to manage content and operations. He credits his parents for instilling discipline and drive and leaves listeners with advice: start before you’re ready, learn by doing, and surround yourself with smart people to scale successfully.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #640 for Wednesday, April 16th, 2025
April 16th: Wear Pajamas To Work Day
00:01:31 Guest Co-host Collin Rutherford from Business Blitz Podcast
Being monetized on X
Recruited to play D1 Hockey at Dartmouth
Started Greenbox Storage in Dartmouth
00:04:42 Time Management running a business while being a D1 athlete
00:07:14 Selling a portion of your business to bring on a partner
00:08:46 SPONSOR: SelectQuote — Get the right life insurance for YOU, for LESS, at selectquote.com/businessbrain.
00:09:51 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!
00:11:04 Shannon’s best practices means… copying Collin!
00:11:54 Social media: post content that attracts the algorithm, then people will see your valuable content
“I’m not that smart, guys.”
Justin Welsh’s Content Flywheel on X
When is it time to pivot and try something different?
00:14:49 It’s important to make mistakes
00:15:11 Grew from 6 branches to 18 branches in one year
We didn’t have any understanding how to find good schools
00:16:41 Unpacking the mindset of success
The never-ending pursuit of personal growth
00:20:08 Starting FounderBrands
00:21:17 Tools to use
Google Workspace
Slack
00:23:15 Have a great team
To Scale a business, you have to put the right people in the right places
00:24:51 Business Brain 640 Outtro <https://businessbrain.show/>
Follow Collin_Ruth89 on X
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