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In a special episode recorded on the move in a Cybertruck, Brian is joined by his friend and founder of Arrowhead Strategy Group, Jarome McKenzie. Jarome shares the powerful entrepreneurial mindset he demonstrated during a 2.5-hour tennis match where he lost every single set 6-0, yet grew more confident with every game. This conversation is a masterclass in resilience, revealing how to find breakthroughs in failure and why the most important work you do happens before your business day even starts. For any entrepreneur feeling stuck or afraid of setbacks, Jarome’s insights on preparation, reflection, and "keeping the ball in play" provide a game-changing perspective on building a sustainable and successful business.
💡 What You'll Take Away For YOUR Business
📝 About Jarome McKenzie
Jarome McKenzie is the founder of Arrowhead Strategy Group, an agency dedicated to helping entrepreneurs find clarity, answers, and hidden growth opportunities within their business numbers and finances. A former college baseball player, Jarome brings a unique, athletic-minded discipline and a deeply reflective nature to the world of business. He excels at breaking down complex challenges into their core components and applying universal principles of success, making him a brilliant strategist for any entrepreneur looking to master the fundamentals and achieve sustainable growth.
📢 Memorable Quotes
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In an era dominated by AI hype, how do you move from simply talking about AI to securely and profitably implementing it? This episode tackles that exact question with Evan Glaser, founder of Alongside AI and an expert at the intersection of AI, cybersecurity, and business strategy. Evan demystifies the world of powerful AI agents, explaining both their groundbreaking potential and the critical security risks they pose. This isn't just a theoretical discussion; it's a practical guide for entrepreneurs who want to leverage cutting-edge AI without compromising their data, their customers, or their company's future. Tune in to learn how to bridge the gap between AI experimentation and real-world, production-ready systems that give you a competitive edge.
💡 What You'll Take Away For YOUR Business
📝 About Evan Glaser
Evan Glaser is the founder and CEO of Alongside AI, a firm dedicated to helping organizations implement AI securely and effectively. With a rich background in cybersecurity, AI governance, and enterprise consulting, Evan specializes in bridging the gap between technical execution and business strategy. His unique expertise allows him to guide leadership teams in reducing AI-related risks while accelerating real adoption. Evan brings a practical, security-first perspective to the AI conversation, making him an essential voice for any entrepreneur looking to innovate responsibly.
🎯 Evan’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"The barrier to accomplishing different tasks has never been lower. If you have a vision for a product or a service... that you have been limited in doing based on your skill set... I would really urge you to revisit them."
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In an era of shiny objects and AI shortcuts, 25-year marketing veteran Scott Orth joins the show to bring us back to the fundamentals that actually grow a business. This episode is a masterclass in building a holistic digital presence, proving that a solid foundation in SEO and strategic paid ads will always outperform chasing the latest trend. Scott breaks down why simply being on Google isn't enough; you need to dominate it from every angle—organic results, maps, and ads—to truly capture your audience.
This episode is invaluable for any entrepreneur tired of marketing strategies that don't move the needle. You'll learn how to transform your website from a static brochure into a lead-capturing machine, the right way to leverage AI as an assistant (not a replacement for human creativity), and how a powerful CRM can automate your follow-up so you never lose a potential customer again. Scott’s deep experience provides a clear, actionable roadmap for increasing visibility and driving real growth.
💡 What You'll Take Away For YOUR Business
📝 About Scott Orth
Scott Orth is an SEO and digital growth expert with 25 years of hands-on experience in the trenches of online marketing. As the founder of Thrive Business Marketing and the creator of Surge by Thrive, he has mastered the art of combining timeless marketing fundamentals with cutting-edge technology. Scott got his start back in 1999, paying for clicks when they were a penny apiece, and has since evolved into a full-stack marketing authority who helps businesses build a powerful, holistic online presence that drives measurable results.
🎯 Scott’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Things don't have to be perfect. Get out there, get it done. You're going to learn as you go."
📢 Memorable Quotes
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In this episode, Connor O'Hearn completely reframes how entrepreneurs should view artificial intelligence. He introduces the game-changing concept of AI as a "navigation system for business"—a dynamic, layered GPS that guides you through complex decisions, rather than just being another static tool. For wantrepreneurs and entrepreneurs, this episode is a masterclass in leveraging AI to fill skill gaps, process overwhelming amounts of data, and make smarter, faster decisions. Connor’s unique journey from sales and geography to co-founding an AI strategy firm gives him a powerful perspective on how technology can enhance human intuition and democratize the tools previously reserved for massive corporations.
💡 What You'll Take Away For YOUR Business
📝 About Connor O'Hearn
Connor O'Hearn is the co-founder of an AI strategy firm dedicated to helping business leaders navigate increasingly complex decisions. With a diverse background spanning business, entrepreneurship, aviation, and even geography, Connor brings a uniquely human-centric approach to the world of technology. His experience in an early-stage startup, where he helped lead a strategic partnership with Microsoft's co-pilot ecosystem, gave him a front-row seat to the AI revolution. Today, he channels that expertise into building a true "navigation system for business," empowering entrepreneurs to turn data chaos into clear, actionable strategy.
🎯 Connor’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
Know what you're really good at, double down on that strength, and then use AI without fear to fill in all the gaps and deficiencies you have as an entrepreneur.
📢 Memorable Quotes
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Ever wonder how a niche hobby can explode into a category-defining brand with a cult-like following? Tim Seward, the founder and creative force behind ONYX Motors, joins us to share exactly how he did it. Starting as a lifelong tinkerer customizing gas mopeds, Tim leveraged his industrial design background and a breakout Indiegogo campaign to launch a brand that blends raw performance with timeless style. This episode is a masterclass in product validation, community building, and the power of authentic passion. For any entrepreneur looking to build not just customers, but true fans, Tim’s journey provides a powerful and actionable roadmap.
💡 What You'll Take Away For YOUR Business
📝 About Tim Seward
Tim Seward is the founder and creative heartbeat of ONYX Motors. A lifelong tinkerer and moped enthusiast with a background in industrial design, he has created products for massive brands like Sonos, Intel, and Nike. Tim combined his passion for two-wheeled vehicles with his expertise in consumer electronics to create ONYX, revolutionizing the electric bike space. His unique perspective blends cyberpunk grit with California swagger, focusing on building not just a product, but a powerful community and culture around it.
🎯 Tim’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"I just followed what I really love to do... if you're having fun working, then it's not really work."
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In this game-changing episode, we sit down with Jill Axline, Ph.D., the co-founder and CEO of Mavera, to explore the next frontier of artificial intelligence in business. Jill demystifies how her company is moving beyond basic language models to model human cognition and emotion, giving businesses a terrifyingly accurate predictive edge. This isn't just about faster answers; it's about understanding the why behind customer decisions, market shifts, and competitive movements. For any entrepreneur tired of making decisions based on guesswork, this conversation is a masterclass in using AI as a strategic collaborator to validate ideas, challenge assumptions, and uncover opportunities you never knew existed. Jill’s journey from studying behavioral science to leading a cutting-edge AI startup provides a powerful roadmap for how to merge human insight with technological power to build a truly intelligent business.
💡 What You'll Take Away For YOUR Business
📝 About Jill Axline
Jill Axline, Ph.D., is the co-founder and CEO of Mavera, where she builds generative systems that give companies instant, scalable insight into people and markets. With a fascinating background that began in design and behavioral science, she holds a PhD where she studied empathy and cognitive perspective taking. Before co-founding Mavera, Jill honed her skills at Morningstar, building their market insights team from the ground up. Her unique expertise lies at the intersection of human insight and intelligent systems, making her a leading voice on how businesses can harness AI not just for efficiency, but for deeper understanding and smarter growth.
🎯 Jill’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Maintain your skepticism... but also have an open mind and don't be dismissive of things before you've really given them a shot... always be learning."
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We’ve all heard the cliché: “You need to work ON your business, not just IN it.” But what does that actually mean? It’s easy to get trapped in the day-to-day grind of client work, emails, and sales calls, feeling busy but not necessarily productive. This cycle creates a growth ceiling that keeps so many entrepreneurs stuck. In this Solo Sunday episode, Brian demystifies this classic advice and gives you a tangible, actionable framework to shift from being a busy operator to a strategic visionary. He breaks down the critical difference between tactics and strategy using a brilliant chess analogy and introduces his powerful 7-pillar OPERATE framework. This is your guide to carving out the strategic time your business desperately needs to scale.
✨ Why This Matters for You
Understanding how to work ON your business is the key to unlocking real growth:
📝 Key Takeaways
🚀 Put It Into Action
This week, schedule your first "ON the Business" strategy session:
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Think your small business is too insignificant to be a target for cyberattacks? Think again. In this eye-opening episode, cybersecurity expert and co-founder of Attainable Security, Martin Hiriart, reveals why small and medium-sized businesses are now the primary targets for hackers. Martin breaks down the critical, often-overlooked connection between everyday IT practices and a rock-solid cybersecurity posture. This episode is a must-listen for any entrepreneur who wants to move fast without leaving their business vulnerable. You'll learn how to implement proactive security measures that protect your company, your customers, and your reputation without slowing down your growth.
💡 What You'll Take Away For YOUR Business
📝 About Martin Hiriart
Martin Hiriart is a seasoned cybersecurity and IT professional and the co-founder of Attainable Security. With a rich background spanning helpdesk support to high-level cloud and identity management, Martin saw a critical gap in the market: small and medium-sized businesses lacked access to enterprise-grade security programs. He and his co-founder created Attainable Security to provide holistic, high-quality IT and cybersecurity strategies, allowing entrepreneurs to build their vision on a secure and efficient foundation.
🎯 Martin’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Find those people and those relationships in your life that are partnerships... just knowing that you have that person or the set of people that you can trust to just, hey, let's work on this together and work towards this shared goal is huge."
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Are you an expert in your field but struggle to communicate your true value to clients, investors, or your team? In this episode, former health insurance executive turned consultant Mandy Geyer breaks down the art and science of influential communication. She reveals why even the most brilliant experts fail to get buy-in and provides a clear roadmap to translate complex data and ideas into compelling stories that drive action. For any wantrepreneur or entrepreneur who feels their message gets lost in translation, this episode is a masterclass in building confidence, connecting with your audience on their terms, and simplifying your value proposition to accelerate growth and impact.
💡 What You'll Take Away For YOUR Business
📝 About Mandy Geyer
Mandy Geyer is the founder of Integral Edge Consulting and a former health insurance executive with nearly 20 years of experience leading actuarial teams. After seeing countless brilliant, technical experts struggle to convey their value, she made it her mission to bridge the gap between data and influence. Today, Mandy works at the intersection of data, storytelling, and persuasion, helping technical leaders, analysts, and health tech companies communicate with clarity and confidence to get buy-in faster and drive meaningful results.
🎯 Mandy’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Make sure you're taking time and space every day to be alone."
📢 Memorable Quotes
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Traditional Google searches are declining by 25% as consumers turn to AI like ChatGPT and Gemini to find products, get advice, and make buying decisions. This is the next major platform shift, and if your brand is invisible to AI, it will soon be invisible to your customers. In this episode, Apurva Luty, a marketing expert from Microsoft, Meta, and Discord, reveals how this AI wave is a massive opportunity for challenger brands to get ahead. Apurva breaks down exactly how to "teach" AI models about your business, ensuring they become your biggest advocates and drive a new wave of traffic and customers your way.
💡 What You'll Take Away For YOUR Business
📝 About Apurva Luty
Apurva Luty has spent the last decade on the cutting edge of every major platform shift in tech. With a track record of turning new mediums into predictable revenue streams at giants like Microsoft, Meta, and Discord, she has a deep understanding of consumer behavior. Apurva is a storyteller and marketer at heart, passionate about translating complex technology into accessible strategies. She is now the founder of Optimly, where she is tackling the final platform shift—AI—and building the tools to ensure challenger brands aren't left behind.
🎯 Apurva’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"Just do it... take that leap, because you are probably more prepared than you realize you are." Apurva’s core advice is to embrace a bias for action. Whether you’re on the fence about starting a business or scared about tackling a new frontier like AI, the key is to stop overthinking and start doing.
📢 Memorable Quotes
🔗 Links & Resources
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