

Business Brain – The Entrepreneurs’ Podcast
Shannon Jean & Dave Hamilton
Two long-time small-business owners, Dave Hamilton and Shannon Jean, come to you each week to talk through the trials, success, pitfalls and tips it takes to successfully run a small business in today’s world. Hear real-world folks talk about real-world problems, letting you know not only what it takes to get it done but that you’re not alone in doing it!
Episodes
Mentioned books

Sep 17, 2025 • 23min
Change and Time Blocking – Business Brain 684
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 two-hour time blocks dedicated to specific businesses and batching email into three 30-minute windows. The approach helps him avoid “working for whoever emailed last,” stay focused, and surface non-urgent but important work. Shannon, having reclaimed calendar space, plans to lean into time blocking as well. They close by inviting listener tips on time and attention management.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #684 for Wednesday, September 17th, 2025
September 17th: National Monte Christo Day
00:01:53 The Power of Embracing Change
Welcoming that end of summer productivity
Teaching your employees how to embrace change
Change…or Fail!
00:08:53 iPods increasing in value because of schools
00:10:11 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:11:24 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:13:34 Compartmentalizing your calendar…Time Blocking
Scheduling time for email (30 min). Time for each business (120min).
00:22:33 Business Brain 684 Outtro
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Sep 12, 2025 • 23min
FridAI - Mundane AI and Less Automation
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 workaround using Tailscale to make streaming services work in multiple locations by routing traffic through a home network exit node.
The hosts emphasize how AI is reshaping simple, daily problem-solving. They share examples like using ChatGPT to identify obscure lighting components or generate podcast interview questions. The theme is clear: what feels mundane to one person might be a lightbulb moment for another—so sharing these use cases is valuable. They encourage listeners to send in their own examples for future episodes.
Toward the end, Shannon introduces a concept inversion: when starting something new, it’s better to avoid automation at first. He shares a story about stagnant Instagram growth despite hiring an agency, only to gain traction after manually asking followers via his newsletter. They discuss how deep involvement early on leads to better understanding, making future automation more effective. The episode closes with a promotion for free Perplexity Pro subscriptions and their usual mix of business tips and charm.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #683 for Casual FridAI, September 12th, 2025
September 12th: National Day of Encouragement
00:01:31 the mundAIne
Explain patterned/targeted spam emails
00:04:54 Tech support for YouTube TV
Get TailScale and setup an Exit Node
00:07:56 Back to the mundAIne
Using ChatGPT as your search engine
Sending ChatGPT a picture of something to explain it
00:11:12 SPONSOR: Mint Mobile – This year, skip breaking a sweat AND breaking the bank. Get this new customer offer and your 3-month Unlimited wireless plan for just $15 per month at MintMobile.com/BusinessBrain today.
00:12:57 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!
00:14:20 Less Automation
Business is about people
00:21:00 Get Perplexity Pro free for 1 year
00:22:22 Business Brain 683 Outtro
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Sep 10, 2025 • 22min
What do you want + The Pot of Gold Myth
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 table along the way. They stress balancing reinvestment with risk reduction, maintaining a reasonable war chest without starving life or business, and seeking outside counsel to counter radical optimism. Dave recalls Howard Stern’s heuristic of not investing personal money if others won’t, as a gut-check on viability. They close by inviting listener feedback on how others think about building, enjoying the journey now, and funding choices.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #682 for Wednesday, September 10th, 2025
September 10th: National TV Dinner Day
00:01:29 Building your keychain to the kingdom
Aron North from Mint Mobile on Business Brain
00:02:18 What are you building towards?
Lifestyle businesses are OK by us!
What do you want? (out of the business you have/are-creating)
…you might already have it.
00:06:56 What do you want to do when you retire have more free time?
You deserve the life you want
00:08:24 What if I don’t create what I wanted?
It’s ok! Systems are better than goals.
And everything can evolve, including your answers to those questions
00:09:58 SPONSOR: Mint Mobile – This year, skip breaking a sweat AND breaking the bank. Get this new customer offer and your 3-month Unlimited wireless plan for just $15 per month at MintMobile.com/BusinessBrain today.
00:11:40 SPONSOR: Shopify – For anyone to sell anywhere, sign up for a one-dollar-per month trial period at Shopify.com/BusinessBrain and upgrade your selling today!
00:13:03 The Pot-of–Gold Myth
Did you get your pot of gold at the end?
There is no pot of gold…but sometimes you can take chests of gold off at times during your career
Don’t wait to take money off the table
Your business’s warchest doesn’t need to be as big as you might think
00:21:11 The Howard Stern lesson: I never invest my own money in my business
00:21:57 Business Brain 682 Outtro
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Sep 5, 2025 • 24min
FridAI - AI Guardrails
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 “simulated intelligence,” a tool that should be matched to the job; the hosts agree, emphasizing oversight and recognizing AI’s limits and “stupid loops.” They daydream about near-term household robots and ask listeners what price would make an “AI handyman” a must-buy. Dave’s quick tip: skip guided food tours and have ChatGPT build a self-guided itinerary tailored to your tastes, which saved his family money and improved the experience. They close by inviting listener feedback on the discussion.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #681 for Casual FridAI, September 5th, 2025
September 5th: Bring Your Manners to Work Day
00:01:22 Opus Clips
Agent Opus Beta
00:03:58 The risks of telling AI personal details
Sometimes AI uses information about you in ways that can be uncomfortable or unhealthy
00:06:48 Don’t make decisions based upon the news
00:09:37 Using technology to stave off loneliness
ChatGPT’s Parental Controls are coming
00:11:08 What’s your “I’m in!” price for an AI Handyman?
Shannon: $20K
Dave: $50K
You? feedback@businessbrain.show
00:13:24 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:14:58 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:16:18 Andy-Is AI Artificial Intelligence or Simulated Intelligence?
00:18:45 Book a food tour with ChatGPT
00:23:27 Business Brain 681 Outtro
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Sep 3, 2025 • 23min
Q&A with Dave and Shannon
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 five-star reviews praising the show’s longevity, actionable advice, and openness, reminding listeners to email feedback@businessbrain.show to enter their MacBook giveaway. More listener feedback introduces “forcing parties” (accountability sessions where people knock out avoided tasks together), which they tie to partner accountability and real-time Zoom coworking. A brief connection delay leads Shannon to discover an AI agent hogging CPU—teasing a Friday discussion. They close by inviting topic suggestions, pointing to businessbrain.show/review, and signing off with their “charmed life” mantra.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #680 for Wednesday, September 3rd, 2025
September 3rd: Global Talent Acquisition Day
The Babybacks Band
00:02:45 Mike-Interview question: How many ways can you use a pencil?
00:05:55 Patrick-Email Signature Management Tip
Keyboard Maestro
TextExpander
00:07:40 Texting vs. Email in Business
00:10:08 SPONSOR: MasterClass. Right now, our listeners get an additional 15% off any annual membership at MasterClass.com/BUSINESSBRAIN
00:11:42 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:13:05 JeffreysBeam-BB Review-5-stars
00:14:25 Rich W Portraits-BB Review-Wow! Great Tips & Advice!
00:16:41 Taylor-Discuss “Forcing Parties”
Bryan O’Connell on Business Brain
CEO Roundtable on Business Brain
00:21:43 Business Brain 680 Outtro
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Aug 29, 2025 • 21min
FridAI Leadership + AI SEO
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.
The conversation then shifts into AI SEO, with Shannon sharing how clients have recently found him through ChatGPT. They explore how AI-driven search is transforming marketing by prioritizing conversational queries, authority, and brand trust over traditional keyword strategies. Best practices discussed include creating clusters of related content, structuring content in a Q&A style, and doubling down on personal branding to stand out in AI-generated answers.
The episode is rounded out with sponsor messages from Bitdefender and Jerry, and the hosts reinforce the importance of proactive adaptation in both business and personal branding as the landscape shifts toward AI-first discovery. They close by encouraging listeners to leave reviews and keep building their “charmed lives.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #679 for Casual FridAI, August 29th, 2025
00:01:10 August 29th: National Chop Suey Day
00:02:54 Can AI Make You a Better Leader?
Maybe!
AI Can help you see things from different perspectives
But don’t use it as a crutch…use it as an unreliable assistant
00:05:38 Can AI be your leadership/management coach?
Be careful with your prompts. You want AI’s answers to be critical, not complementary.
Choose a leader who has had success and that you want to emulate. Tell AI to be your mentor based upon Bob Iger (for example, or Jack Welch, or Bill Campbell)
BusinessBrain.show/Brain – ask our brain!
00:09:57 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:11:25 SPONSOR: Jerry. Car insurance made simple and finally on your side. Drivers who save with Jerry save on average $110 a month! Head to JERRY.ai/BusinessBrain today.
00:13:29 Do you need AI SEO for your business?
(The answer is yes)
Trust signals matter the most: Authority, Credibility, Structured Content
FAQ, How-to, Comparison Posts
Build topical authority with clusters, not keywords
Double down on your brand!
00:19:12 The personal brand is so important
00:20:12 Business Brain 679 Outtro
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Here’s what ChatGPT has to say about AI SEO:
Great question — this is one of the biggest shifts happening right now in marketing. Being “AI-SEO ready” means preparing for a world where people ask AI (ChatGPT, Perplexity, Gemini, etc.) instead of typing keywords into Google. Here’s how to think about it:
1. Understand the New Search Behavior
Conversational queries: Instead of typing “best hiking boots,” users will ask, “What are the best hiking boots for wet trails under $200?”
Direct answers, not links: AI gives summarized, synthesized answers. If your brand isn’t cited as a trusted source, you may get skipped entirely.
Trust signals matter more: AI looks for authority, credibility, and structure in content when choosing what to reference.
2. Structure Content for AI Retrieval
Answer questions clearly: Write in a Q&A style that matches conversational prompts people ask AI. FAQ sections, “how-to” guides, and comparison posts work well.
Use structured data: Schema markup (product info, reviews, author details) gives AI models clean signals to pull from.
Concise summaries: Start articles with clear, 2–3 sentence overviews — AI loves digestible takeaways.
3. Build Topical Authority
Clusters over keywords: Instead of one keyword article, build a cluster of related content around a topic. Example: not just “handbag resale tips,” but a cluster on sourcing, pricing, authenticity, marketplaces, and scaling.
Authoritativeness: AI prefers sites with expertise demonstrated across multiple related articles, not one-off posts.
4. Optimize for Citations (AI Mentions)
Get linked from high-authority sites (news, universities, niche blogs). AI often pulls from these sources.
Original research, stats, and case studies are gold. AI tools surface data points, so if you’re the source, you get visibility.
Unique frameworks/methods (like your “Liquidation Method”) help you stand out. AI is more likely to reference branded systems than generic content.
5. Think Multi-Channel, Not Just Google
AI assistants pull from YouTube, Reddit, forums, and newsletters as much as websites. Posting your content in diverse channels increases discoverability.
Podcasts and transcripts also matter — AI uses them as knowledge sources.
6. Double Down on Brand
As AI search becomes more answer-oriented, the brand is the differentiator. If someone just trusts “Shannon Jean’s Reseller Mastermind” instead of “some blog,” they’ll bypass generic AI answers and go directly to you.
In short:
Prepare by writing conversational, authoritative content clusters, marking them up properly, and publishing in multiple formats (web, audio, video). Then focus on building brand trust so when people do get AI answers, they’re looking for your name in them.Would you like me to create a playbook/checklist you (and your mastermind members) could use to make sure every piece of content is “AI-SEO ready”?
The post FridAI Leadership + AI SEO – Business Brain 679 appeared first on Business Brain - The Entrepreneurs' Podcast.

Aug 27, 2025 • 26min
The 17-37 Rule + Review Culture
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 value and keeping a beginner’s mindset in entrepreneurship.
Sponsors Bitdefender and Jerry are introduced, emphasizing cybersecurity for small businesses and simpler car insurance shopping. Dave stresses the importance of communication and trust in small business tools. The hosts then dive into Airbnb experiences, emphasizing how five-star reviews have been inflated and are no longer informative. They discuss the value of proactive communication with guests, fixing small issues, and even suggest reforming review systems to start at a baseline lower than five stars to provide more meaningful feedback.
They close by encouraging listeners to leave a five-star review for the podcast at businessbrain.show/review, promoting a MacBook giveaway as an incentive, and reinforcing their message of living a charmed entrepreneurial life while learning through curiosity and adaptability.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #678 for Wednesday, August 27th, 2025
August 27th: National Just Because Day
00:03:40 Learning to be a community builder
Adding value for between $17 and $37
00:08:31 “I watched a tutorial”
Kajabi
00:10:39 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:12:07 SPONSOR: Jerry. Car insurance made simple and finally on your side. Drivers who save with Jerry save on average $110 a month! Head to JERRY.ai/BusinessBrain today.
00:14:12 The Flaws of Stars-Based Review Culture
Quick Tip: Stay at your AirBnB regularly to fix all the little things
00:20:48 Vacation Rental Success and Failure Stories
00:23:29 Review Inflation
00:26:03 Business Brain 678 Outtro <https://businessbrain.show/>
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Aug 22, 2025 • 18min
FridAI - Operators and Agents
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 belief and purpose in work must eventually come from within the team, not just from the founder’s enthusiasm.
The conversation then shifts into a discussion of AI agents and operators. While both hosts are avid users of ChatGPT and consider it incredibly valuable, they express skepticism around AI agents, noting that most current implementations feel unfinished or unreliable for business-critical tasks. Dave mentions his positive experience using GitHub Copilot for coding, while Shannon describes ChatGPT as a daily-use tool that saves thousands of dollars. Both are eager to hear from listeners who have had success with AI agents and encourage feedback, hoping to one day integrate them meaningfully into their workflows.
The episode also includes sponsor spots for Bitdefender and Constant Contact, with Dave highlighting Bitdefender’s scam protection for small businesses and Constant Contact’s all-in-one marketing automation features. The hosts wrap up the show with appreciation for their audience and a reminder to keep living the “charmed life.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #677 for Casual FridAI, August 22nd, 2025
00:01:11 August 22nd: National Tooth Fairy Day
What is your noble cause?
00:07:21 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:08:50 SPONSOR: Constant Contact makes marketing easier and more effective for small businesses like yours. Try Constant Contact free for 30 days at ConstantContact.com
00:10:36 Operators and Agents and…Progress?
Github CoPilot
00:16:57 Business Brain 677 Outtro
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Aug 20, 2025 • 22min
Full Family Buy-In and Sports Guy
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 pushback.
They expand the conversation by emphasizing how buy-in isn’t just important at home—it’s also critical within your team. Specifically, Dave highlights how the families of employees can influence retention, so building a workplace that employees proudly talk about at home makes a significant impact. The hosts then pivot to a fun yet practical idea about hiring socially aware team members (like a sports expert) to help connect with clients and customers through shared interests like sports. They end the episode with favorite interview questions that help identify personality and passion, encouraging listeners to send in their own to enter a MacBook giveaway, all while reinforcing the show’s theme of living a “charmed life.”
00:00:00 Business Brain – The Entrepreneurs’ Podcast #676 for Wednesday, August 20th, 2025
00:01:00 August 20th: National Bacon Lover’s Day
Millionaire Bacon at Sweet Maple on the menu
00:03:19 The Importance of having full family buy in (for you, yes, and also for your team/employees)
Everyone is a customer
00:11:21 SPONSOR: Bitdefender. Keep your small business safe with Bitdefender Ultimate Small Business Security. Save 30% when you go to bitdefender.com/BRAIN
00:12:52 SPONSOR: Constant Contact makes marketing easier and more effective for small businesses like yours. Try Constant Contact free for 30 days at ConstantContact.com
00:14:38 What do you do if you’re not a sports person?
Sports can be a huge part of business
00:18:34 Interview questions
What are YOU a nerd about?
What should I remember about you?
00:21:40 Business Brain 676 Outtro
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Aug 15, 2025 • 16min
The Business Brain is Alive
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 enhanced reasoning. Shannon shares a real-world example of using GPT-5 to troubleshoot an AC issue in his son’s car, demonstrating how AI can offer guided problem-solving by progressively asking for more input. They also talk about developments in LLM access restrictions (e.g., Cloudflare’s paywall for crawling), and Shannon’s use of agents and tools like Comet from Perplexity.
The episode closes with thoughts on the evolving AI landscape, the growing number of paid tools, and how each platform competes and leapfrogs each other with new releases. The hosts encourage listeners to try out their new “brain” tool, share feedback, and connect via social media or email to discuss how they’re using AI in their own businesses.
00:00:00 Business Brain – The Entrepreneurs’ Podcast #675 for Casual FridAI, August 15th, 2025
August 15th: National Relaxation Day
00:01:10 Delphi AI Business BrAIn … it’s alive!
00:04:34 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!
00:06:06 SPONSOR: Eversite – Your own in-house web team for just $399/month. No big upfront fees, no long-term contracts—just a gorgeous, pro-managed website without the stress. Visit Eversite.com/bb to get started today!
00:07:29 ChatGPT GPT-5 Features (with Thinking!)
00:10:14 Cloudflare’s LLM Block
00:11:16 Feeding ChatGPT symptoms of a problem…and come up with a solutions
Perplexity Comet
00:14:25 When in doubt, start a new chat!
00:15:32 Business Brain 675 Outtro
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