Business Brain – The Entrepreneurs’ Podcast

In this episode of Business Brain, you’re challenged to stop using AI as a polite yes-man and start treating it like a ruthless sparring partner. You learn how to pressure-test your thinking before you ever type a prompt by defining the real decision, the outcome that actually matters, and the constraints you refuse to break. Shannon Jean and Dave Hamilton walk you through using AI to surface opposing viewpoints, rank options by impact instead of effort, and expose second-order consequences that can make or break your strategy. This is how you sharpen judgment instead of outsourcing it.

In this episode of Business Brain, you’re challenged to think differently about how people experience you and your business. You explore why your personal brand is more powerful than any logo or company name, because people connect with you first. From lessons inspired by Crazy Eddie to the idea of the Alter Ego Effect, you’re reminded that sharing what you’ve learned—and giving yourself permission to evolve—builds trust faster than polished marketing ever could.

You also learn how consistency compounds over time, why replying first with value puts you on the radar of bigger pla...

In this episode of Business Brain, you step into the fast-moving world of AI and learn how to choose the right tool for the job. You compare Perplexity, ChatGPT, Claude, and Gemini, with real-world insight into why Perplexity may hallucinate less right now. You explore purpose-built tools like Gamma AI for presentations, NotebookLM for research, Manus AI for automation, and creative powerhouses like Sora AI and Google Veo. The focus is simple: stop chasing shiny objects and start picking AI that actually moves your business forward.

You also hear how AI is showing up in everyday workflows...

In this episode of Business Brain, you step back and review what 2025 really taught you as an entrepreneur. You’re challenged to stop being transactional and start building a transformational community, to take control of your feeds instead of letting social media control you, and to notice where distractions have quietly turned into complacency. Shannon and Dave remind you that hunger fades if you let it—and that staying sharp sometimes means becoming your own friendly pest in pursuit of progress and a truly Charmed Life.

You’re encouraged to embrace the fear of failure, run smart busine...

In this episode of Business Brain, you explore how tools like Perplexity and Manus AI can move you from scattered ideas to clear execution. You see how AI helps you design a professional development plan, clarify complex concepts before implementation, and even generate a forward-looking review of your year. The focus is on using AI as a thinking partner—one that sharpens your strategy instead of replacing it.

You also learn how to combine AI tools to build practical systems, including custom dashboards that surface what actually matters in your business. By asking better prompts and layering to...

In this episode of Business Brain, you’re challenged to stop playing it safe and start leaning into the discomfort that drives real growth. You explore why staying comfortable is often the biggest limiter in business, and how intentional unease sharpens your thinking, strengthens decision-making, and exposes opportunities you’d otherwise miss. When you choose discomfort on your terms, you regain control instead of letting fear make the calls for you.

You’ll learn how to reframe uncomfortable moments as signals—not stop signs—and use them to build resilience, confidence, and momentum. By pushing just past what feels...

In this episode of Business Brain, you take a hard look at the hidden risks of using AI to troubleshoot problems in your business. You learn why trusting confident-sounding answers without context can lead you astray, and how Gell-Mann Amnesia shows up when AI sounds smart outside your expertise. The takeaway is clear: AI is powerful, but only when you stay skeptical, verify results, and remain the final decision-maker.

You also explore the fast-evolving world of AI-powered wearables and what Meta’s smart glasses signal for the future of work and creativity. From short-form recording to deeper ap...

In this episode of Business Brain, you’re challenged to stop waiting for perfect conditions and start before you feel ready. You don’t need every system built or every detail nailed down to make an offer and move forward. You learn why perfection slows momentum, how action creates clarity, and why progress beats polish every time. This mindset shift helps you build confidence, traction, and revenue faster—without getting stuck preparing forever instead of doing.

You also explore demand avoidance and the subtle danger of the comfort zone. When things feel easy or familiar, it might actual...

In this episode of Business Brain, you dive into the rising tension between innovation, trust, and responsibility in the world of AI. As Shannon and Dave unpack National Salesperson Day, they pivot into the challenge of working with tools that hold immense power but zero accountability. The conversation heats up as they explore the recent acquisition of Limitless and what it signals for the future of AI assistants that promise productivity without sacrificing your Charmed Life.

You also hear why trusting your AI is becoming just as important as the tasks it performs. Apple enters the discussion...

In this episode of Business Brain, you learn why belief has to show up before skill ever can. You’re pushed to take action immediately—not by buying gear, courses, or tools, but by selling what you already have to get real-world wins fast. As you move, you build confidence, momentum, and the all-important belief that fuels every entrepreneurial step of your Charmed Life. Listener reviews highlight how authentic, actionable, and inspiring this mindset is, especially when paired with smart discussions about AI and real business challenges.

You also dive into the big question: How long should you...

In this episode of Business Brain, you’re reminded that the work itself is the reward—and that avoiding the arrival fallacy is key to building a Charmed Life. Shannon and Dave push you to reframe your mindset from have to to get to, reinforcing that shared effort fuels momentum. You’ll see how celebrating your team—especially on Extraordinary Work Team Recognition Day—creates a culture where contribution feels meaningful and progress stays sustainable.

Then you dive into the art of employing confident helpfulness. You’re coached to stop bending over backward until clients walk all over you and...

In this episode of Business Brain, you dive into a Casual FridAI conversation where Shannon Jean and Dave Hamilton explore everything from Google’s playful foray into “antigravity” ideas to the rise of vibe-based coding and whether it helps or hurts creativity. You’re pulled into their energetic breakdown of how intuition and experimentation shape modern work, especially in an era when AI tools push boundaries faster than ever. As the hosts riff on innovation, they challenge you to rethink how you incorporate emerging tech into your entrepreneurial workflow to build your own Charmed Life.

You also get a sh...

You’re juggling data, marketing, and momentum, and this episode shows you how to turn all three into leverage. You learn why permissionless UTMs let you track audience behavior without waiting for approval, giving you a sharper view of what actually moves the needle. Then you’re pushed to rethink how you approach follow-ups and persistence — not as nagging, but as the habit-forming consistency that makes people naturally want to work with you. This is where you start building your own Charmed Life.

We also explore how relationship shifts inside a company — especially when your point of contact...

On this episode of Business Brain, you explore how to use AI as a tool for revealing blind spots you didn’t even know you had. With prompts designed to surface hidden assumptions and second-order effects, you learn how to turn AI into a sharper strategic partner. The hosts walk you through asking AI to SWOT your life, push for specific examples, and then combine strengths and weaknesses so you can take real corrective action instead of just collecting insights.

This episode also shows you how to redirect AI when answers drift and how to make it as...

Adding value in business doesn’t always mean solving every problem — sometimes simply naming the issue helps people unlock their own path forward. That mindset protects you from the Consultant Trap, where you feel obligated to deliver solutions instead of insight. Like cognitive behavioral therapy, your real power often comes from reframing the situation, not fixing it. Whether you’re chatting with clients, partners, or even hotel staff when you’re celebrating something special, you’re shaping outcomes through clarity and communication.

We also explore how lifestyle businesses can slip into complacency when comfort replaces intention. You’re pushed to...

You’re living in the future now—where ChatGPT rides shotgun and your car’s dashboard becomes your co-pilot. This week, you’ll explore how AI and CarPlay are merging to make driving smarter and conversations with tech more natural. Discover how Shannon and Dave use GPT behind the wheel and why they wouldn’t buy a car without CarPlay anymore. You’ll see how these tools blend productivity and creativity into the rhythm of daily life.

Then, shift gears into understanding the context window—the secret to keeping your AI assistant on track. Learn how to get better, mo...

You know that consistency is the secret sauce of every successful venture. This episode shows you how showing up—again and again—builds your credibility, sharpens your edge, and strengthens your moat against competitors. With the Business Brain hosts breaking down “bullheaded persistence” and the beauty of being “too dumb to quit,” you’ll see why consistency is more than habit—it’s identity.

You’ll also learn why accountability partners can turbocharge your follow-through and how competing with yourself keeps your growth curve alive. Shannon and Dave share how staying consistent has powered them to 700 episodes and a truly Charmed...

You’ll learn how to supercharge your entrepreneurial workflow with AI as Shannon and Dave dive into the latest ChatGPT tricks, from snapping store photos to capturing screenshots and shaping your business philosophy with better prompts. You’ll discover how adding context helps AI think more like a partner and less like a tool—helping you make sharper, faster decisions. This is all about working smarter so you can live your Charmed Life.

They also explore the world of wearable AI, including the Limitless Pendant and its seamless sync with Apple Reminders. With real talk about privacy, produc...

As you navigate the waves of life and business, this episode reminds you that age isn’t a limitation—it’s momentum. Shannon and Dave dive into how your brain evolves from chasing facts to harnessing wisdom, helping you spot patterns and ride bigger waves of opportunity. You’ll learn to see mistakes as tuition and fear as a tool, not an obstacle. Whether you’re 25 or 65, you can turn experience into advantage and live your Charmed Life.

They break down how to flip fear-based thinking into forward motion, using uncertainty as fuel for smarter, faster decisions. If you’ve...

You’re already using AI every day—but are you actually using it smartly? In this week’s Business Brain, Shannon Jean and Dave Hamilton explore the next level of practical AI for entrepreneurs, from using your browser to scrape data instantly to letting AI listen, watch, and analyze what’s happening in your business. You’ll learn how to troubleshoot, research, and brainstorm faster just by speaking to your computer, snapping a video, or using your browser as your AI command center.

You’ll also hear about the tools that make it all click—Comet, Atlas, and Limitless—...

You already know that building a business is a marathon, not a sprint—but how do you keep running when the finish line keeps moving? In this week’s Business Brain, Shannon Jean and Dave Hamilton dive into the concept of Motivational Endurance, sharing ways to recharge your entrepreneurial drive and find joy in the daily grind. From creating a “To Did” list that celebrates small wins to finding multiple sources of motivation, you’ll learn how to build habits that fuel long-term success and keep your energy high even when your excitement dips.

You’ll also disc...

In this episode of Business Brain, Dave and Shannon kick off a lighthearted Casual FridAI conversation that revolves around practical AI tips and how they’re integrating AI tools into everyday problem solving. Dave shares a recent experience using the ChatGPT mobile app to diagnose a foot issue by uploading and annotating photos directly in the app, highlighting how powerful visual AI has become for troubleshooting real-world tasks. Shannon adds examples of how he uses AI to identify dashboard warning lights, analyze auction pallet photos, and even figure out how to put a rental SUV into drive. This leads in...

In this episode of Business Brain, Shannon Jean and Dave Hamilton explore the difference between 2x and 10x growth mindsets. Shannon shares a quote from a recent event — “focus on 10x, not 2x” — and breaks down how the 2x approach is about working harder and incrementally improving, while 10x thinking requires transformative change, ruthless prioritization, and bold decision-making. They discuss how 10x growth forces entrepreneurs to abandon outdated systems and focus only on what delivers real results, even if that means disrupting what’s already working. Shannon relates this to his recent Instagram growth experiment and how it’s forcing him...

Dave and Shannon open Casual Friday with a Shopify nod, then spotlight listener David’s “vibe-coded” Replit app for high-school sports. His web iPad tool tracks scoring, fouls, streaks, and biggest leads, exports structured summaries to an AI project, and let him publish recaps before leaving the gym. The hosts urge productizing it as a simple SaaS for local media and parents, noting how low-code iteration unlocks niche, high-value workflows.

Listener Ian contributes a prompt to reduce ambiguity in text communications—analyze likely interpretations, confirm intent, then offer two clearer rewrites—which sparks a broader discussion about using AI t...

Dave and Shannon kick off episode 692 with a Shopify sponsor read and dive into listener-submitted interview questions. Jeff’s favorite prompt—“How many gas stations are in the U.S.?”—is used to evaluate problem-solving under pressure, not factual recall. Shannon riffs on the persuasive power of specific numbers and “making the truth fantastic,” while Dave notes real estimates vary widely. Todd’s “What would you put on a bumper sticker?” uncovers candidates’ core beliefs; the hosts swap their own slogans and talk about how pithy lines often emerge over the years, not on demand.

Listener Andrew asks whether his fabri...

Dave and Shannon kick off episode 691 on National Handbag Day, segueing from Shannon’s experiment that grew into selling 7,000 handbags and nearly $4M in revenue. He explains how handbags taught him the power of emotional selling and confidence-driven purchases. The conversation pivots to ChatGPT “tasks” (automations) that perform timely research and send results—born from Dave’s football-pick workflow—and expands to examples like weekly industry briefings, sponsor invoicing reminders, and Apple Shortcuts/Zapier/IFTTT integrations to reduce friction and beat procrastination by starting work for you.

They broaden the lens to AI’s impact on creative industries: ga...

Dave and Shannon open episode 690 on National Fluffernutter Day with playful banter before diving into the core theme: “execution is the moat, not information.” They argue that oversharing isn’t risky because ideas are plentiful; what matters is doing the work. Dave recalls advice from a VC contact that asking for NDAs is a rookie move—investors back people who will execute, not just ideas. Sharing publicly sharpens thinking, invites useful critique, and reinforces learning, while daily incremental action is what separates success from stagnation. They weave in a Masterclass sponsor segment as an example of learning that fuels better e...

Dave and Shannon kick off Casual FridAI by sharing practical body language tactics for Zoom and sales calls: stand to boost energy, avoid crossed arms, gesture intentionally (without smacking the mic), and hide self-view to reduce fatigue. They invite listener tips and note small cues—posture, face-touching, taking up space—shape how others read you.

They then demo Limitless AI (formerly Rewind): a pendant + Mac/phone apps that capture conversations, generate searchable “Life Logs,” set voice reminders, and answer questions like “what commitments did I make today?” Use cases span entrepreneurs, ADHD support, journalism, medical visits, and elder care...

Dave and Shannon kick off Business Brain ep. 688 on World Sake Day by riffing on a San Diego beach rental and the power of being a customer of your competitors—and your own business. They share lessons from buying and selling: Dave used paid podcast ads to learn the market and build relationships, and both discuss selling cars and iPhones with smart baselines (Carvana, Gazelle) to stay in control. They swap tactics for negotiating with dealers, anchoring offers, stacking incentives, and using time constraints to avoid the showroom grind.

The conversation pivots to deal-making on both the bu...

Episode 687 opens with sponsors Paka Apparel and Shopify, then dives into a practical compare-and-contrast of LLMs. Dave sticks with ChatGPT for history and workflow but says Claude is hands-down best for assisted coding due to reliability, longer context, and faster iteration. Perplexity earns points for research (and a 12-month Pro via PayPal promo); its Comet browser is mentioned. Shannon uses Grok on X to verify posts and add context. They read listener reviews, remind folks about the MacBook giveaway, and plug businessbrain.show/review.

The pair share real-world AI wins: Shannon fixes a Polaris Ranger parking brake...

Episode 686 opens with sponsors Shopify and Paka Apparel, plus a quick birthday nod to Dave. Dave recaps a concert trip to Hampton, VA: a cool, round, indoor Hampton Coliseum with great sound, but a struggling town he wouldn’t visit except for shows.

Shannon then details how consistent posting on X led to coaching requests, a $5/month subscriber DM that grew unwieldy, and ultimately the Kajabi-based “$5 Reseller Mastermind.” He built lead magnets and a weekly newsletter (5,500 subs), added paid upgrade programs (Costco, eBay, Poshmark, Facebook Marketplace), and replaced 1:1s—canceling 118 appointments—in favor of bi-weekly group calls with 60–70...

Dave and Shannon open a playful Casual FridAI episode for Talk/Meow Like a Pirate Day, then pivot to an NFL pick’em story: Dave joins a family pool and has ChatGPT and Perplexity generate weekly picks, even pitting them against each other and noticing different “motivations” when prompts imply stakes (e.g., deleting a chat). That leads to a discussion about what AIs “value” (usefulness, accuracy, clarity) and how prompt design can shape urgency and quality of output.

They pose a provocative question: if AI replaced you tomorrow, what would it do first? Both admit the answer exp...

Dave and Shannon open with a light riff on Monte Cristo sandwiches before diving into the theme of embracing change—seasonal shifts, life rhythms, and how entrepreneurs must adapt faster than most. Shannon shares how he normalizes change with employees, vendors, and even in his family’s vacation-rental business, warning against getting stuck in “the way we’ve always done it.” They use Apple as a case study of self-disruption (iPod to iPhone to Watch) and debate school phone restrictions, noting the recent resale spike in iPods as districts limit smartphones.

Dave then details a productivity reset: adopting t...

In this episode of Business Brain, Dave and Shannon introduce a new Casual Friday segment called “The Mund-AI,” where they explore seemingly mundane ways they’re using AI tools like ChatGPT in everyday life. Dave shares how he used ChatGPT to make sense of repeated acquisition emails for his business, asking the AI to analyze patterns and even generate template responses. Shannon highlights using ChatGPT as a complete replacement for search engines, especially for things like troubleshooting YouTube TV limitations or checking fishing regulations—tasks that would have been tedious with traditional search tools. Dave even explains a clever workarou...

Dave and Shannon kick off episode 682 by reframing a core entrepreneurial question: not “define success,” but “what are you building toward?” They discuss lifestyle businesses without stigma, urging founders to articulate what they truly want—more time, flexibility, specific experiences—and to design daily systems that move them toward that vision. Shannon shares his “campfire” story concept as a motivating north star and notes that goals can evolve; you may already have much of what you’re after.

In the second half, Shannon tells the “pot of gold” story from an early warehouse lease, learning to take “chests of gold” off the...

Dave and Shannon kick off Casual Friday by troubleshooting a recent recording delay that turned out to be an AI video agent (Opus Clip beta) hammering CPU, noting browser quirks and local processing. They pivot into a broader conversation about the risks of oversharing personal details with AI, the “sycophant” tendency of chatbots, impacts on teens, and the need for parental controls and guardrails. Dave cautions against overreacting to isolated news stories amplified by modern media, while both acknowledge AI can help process thoughts and even ease loneliness—ideally as a temporary aid.

Listener Andy reframes AI as “si...

Dave and Shannon open episode 680 by diving into listener mail: Mike’s favorite interview question (“How many ways can you use a pencil?”) as a way to break candidates out of scripted answers and spark creativity; reflections on interviewing via internships; a humorous twist on “sell me this pen.” Patrick shares text-expander shortcuts for email signatures; Dave notes built-in iPhone/Mac text replacements, while Shannon says he now relies more on Slack/DMs than email. They joke about a dream where speaking louder makes text larger and note texting’s lack of native follow-up tools.

Mid-episode they read two fiv...

Dave and Shannon kick off this Casual Friday episode with some lighthearted banter about the difference between chop suey and chow mein before diving into a deeper conversation about AI’s role in leadership. They agree that AI can be a valuable assistant, offering perspective and analysis, but caution that it can also mislead leaders if used as a crutch or if prompts aren’t carefully designed. They emphasize using AI as a tool for growth, not validation, and suggest frameworks like modeling AI responses after respected leaders such as Bob Iger or Bill Campbell to get constructive feedback.

Dave opens the episode by sharing about his travels to Dallas for Podcast Movement and then to Toronto with his family, where they finally fulfilled his promise to take his kids to see Oasis. The concert, made even more memorable by pouring rain, became a lesson in shared adversity and living a “charmed life.” This transitions into Shannon discussing his growing $5/month online community for entrepreneurs learning reselling, now at nearly 1,200 members. He experiments with adding a $29 Costco liquidation guide as an upsell during signup, which quickly generated $1,000 in its first week. The two highlight the importance of offering real...

In this Casual Friday episode of Business Brain, Dave Hamilton opens with a heartfelt parenting story sparked by National Tooth Fairy Day, tying it into a broader business lesson. He shares how his daughter realized the truth about Santa, and he used it as an opportunity to empower her with belief by choice—not enforcement. Dave and Shannon explore how this same dynamic applies in business: leaders initially carry the energy and vision, but over time, it’s crucial to pass that belief to team members and allow them to choose to buy into the mission. Shannon emphasizes how beli...

In this episode of Business Brain, Dave and Shannon kick off with a humorous and enthusiastic celebration of National Bacon Lovers Day, sharing stories about smoked bacon, pig candy, and even a mug full of bacon. The conversation then shifts to a meaningful discussion about the importance of gaining buy-in from your family when pursuing entrepreneurship. They stress that support from spouses, kids, and even extended family members is crucial for long-term success and mental stability as an entrepreneur. Shannon shares that he often encourages clients to include their spouse in business discussions to ensure alignment and eliminate negative...

In this episode of Business Brain, Dave and Shannon share the launch of their new AI-powered tool built using Delphi.ai, which allows listeners to search through over 11 years and 674 episodes of Business Brain content. The tool, which can be accessed at businessbrain.show/brain, offers personalized insights by indexing approximately 4 million words of past episodes. They emphasize that it only pulls from their show’s advice and interviews, making it a focused and reliable resource.

They also discuss the latest updates in ChatGPT-5, noting improved context handling, multimodal capabilities (like integrating text, audio, and video), and en...

In this episode of Business Brain, Dave Hamilton and Shannon Jean open with lighthearted banter about left-handedness before Shannon shares a major milestone: his $5 Reseller Mastermind has reached over 1,000 members. He explains how the community started almost by accident through X (Twitter) subscriptions, evolved to a Kajabi-based platform for better management, and now allows members to connect, share resources, and learn. The move off social platforms gave Shannon ownership of his audience and reduced his personal workload as members help each other.

The conversation then shifts to Dave’s new business maxim: “Burned bridges kill future deals,” an ext...

In episode 673 of Business Brain, recorded on International Beer Day 2025, Dave and Shannon attempt a live experiment: building a “Business Brain” AI using Delphi. Inspired by Chris Koerner’s “ChrisGPT”, they explore connecting their decade-long podcast archive to Delphi, aiming to let listeners query their advice, strategies, and philosophies directly. Although the onboarding process reveals some friction—Delphi treats them as a single person and requires identity verification—they begin the setup and plan to continue refining it offline.

Shannon also shares his experience upgrading to ChatGPT Teams to connect it with his Google Drive. This enables deeper data an...

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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 ca...

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...

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 de...

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 o...

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 cont...

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 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 co...

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 enco...

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 c...

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 ac...

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 pe...

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 re...

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 capt...

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...

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 a...

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 fo...

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 mind...

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 pr...

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 ca...

In Episode 652 of Business Brain, Shannon Jean shares reflections from a recent trip to St. Lucia, highlighting the stark contrast between poverty and wealth on the island. He emphasizes how entrepreneurship there is a means of survival, with locals creatively hustling to sell everything from handmade goods to rum punch. The experience reminded him of the privilege and opportunity many in the U.S. enjoy, reinforcing the idea that success often stems from grit, simplicity, and perspective.

Shannon and Dave Hamilton explore the power of a “blue-collar mindset” in white-collar businesses—doing the hard work first before automa...

In Episode 651 of Business Brain, Dave and Shannon dive into the concept of a “credibility funnel”—a precursor or complement to the traditional sales funnel. Shannon emphasizes how today’s AI tools can elevate a business’s professional image, especially through visual storytelling. He shares how he uses Napkin.ai to visualize abstract business ideas like credibility, customer service, unfair advantage, and storytelling, making complex concepts easier to communicate and more engaging for clients and newsletter readers.

They also explore AI-powered customer support, spotlighting Gumroad’s use of Helper AI to send highly relevant and...

In Episode 650 of Business Brain, Dave and Shannon welcome guest Michael Greenberg from 3rd Brain to explore the essential but often overlooked world of digital operations. Michael explains that before companies dive into AI and automation, they need to establish solid foundations—clear processes, documented operations, and organized data. His firm focuses on getting businesses “AI-ready” by standardizing internal workflows, integrating tools effectively, and building a unified data structure. This strategic groundwork is crucial, especially for older, legacy businesses that haven’t evolved digitally in decades.

The conversation touches on common pitfalls, like SMBs being distracted by shiny ne...

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 s...

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 e...

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 a...

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.

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 tr...

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 levera...

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...

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 earl...

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!

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 mi...

Dave and Shannon kick off the episode reflecting on the importance of mindset and self-talk. Dave shares a recent insight: instead of saying “I wish I had known that,” he shifted to “I’m glad I know that now,” which they agree is a powerful mental reframe. They talk about how this kind of positive self-programming builds confidence and impacts relationships with others in business, including employees and vendors.

They also discuss how language affects perception, both internally and externally. Shannon gives an example of reframing a client’s negative self-talk about having a “chaotic mind” into something more e...

In this episode of Business Brain, Dave Hamilton and Shannon Jean kick things off with a humorous nod to International ASMR Day before diving into key business tips. Dave shares insights from the Podcast Movement Evolutions conference, emphasizing the importance of identifying where your industry engages online—like how the podcast ad industry is active on LinkedIn. By interacting there for just 30 minutes a day, he significantly boosted connections and created new business opportunities.

They also stress the value of joining conversations without immediately pitching—just genuinely engaging first. Tools like Seamless.ai are recommended for finding emai...

Dave and Shannon discuss the “consulting trap”—the cycle where coaches or consultants trade time for money and get hooked on the immediate gratification of helping people, like feeling like Superman. Dave shares his own experience getting stuck in it and warns that it’s not scalable. Shannon agrees, saying he’s early in his coaching business and is already feeling the limits of one-on-one work. He’s working on solving this by automating, hiring help, building curriculum, creating group programs, and selling digital products. He started by offering free coaching to test the waters and quickly saw demand. They talk ab...

Dave Hamilton and Shannon Jean open the episode with a light chat about peanut butter and jelly sandwiches. Dave then shares insights from attending South by Southwest (SXSW), focusing on a documentary called Strange Journey: The Story of Rocky Horror. Initially intending to cover it for his music podcast, Dave realizes the documentary offers a deeper business lesson.

The film covers how Rocky Horror started as a stage musical in London, became popular, moved to L.A., and was eventually turned into a low-budget movie. It initially flopped, but the creators noticed college students were the ones...

In this episode of Business Brain, hosts Dave Hamilton and Shannon Jean celebrate National Hot Tub Day by discussing how hot tubs help them decompress and unplug. They transition into AI and automation, sharing practical Gmail tips—like using built-in templates for quick replies and the “+” email trick for tracking sign-ups and spam.

They discuss the benefits of small automations, like smart lighting and motion-activated garage lights, which save time and mental energy. Shannon emphasizes using tools like Calendly to automate appointments and streamline client interactions, even incorporating automated sequences for paid consulting calls. Dave encourages listeners to sta...

Dave Hamilton and Shannon Jean open episode 634 of the Business Brain podcast by sharing personal updates and diving into a frustrating customer service story from Shannon. He explains his negative experience with Bluehost, a company he used for domain management. After being hacked and receiving poor support with constant upselling, he moved his sites elsewhere but left domains with Bluehost, which later caused major DNS issues. Bluehost reset his DNS records after ending his hosting plan, leaving his business offline for days and requiring a tedious domain transfer process. Dave empathizes and recommends Cloudflare as a better DNS and...

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.

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.

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 A...

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 motivate...

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 sh...

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 ar...

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...

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...

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...

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 r...

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...

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 co...

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 l...

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 a...

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 high...

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...

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.