Podcast
Strap on your Boots
Hosted by Jason Sherman · EN
Successful technologist and filmmaker Jason Sherman gives you real world examples on how to realistically succeed in the world of entrepreneurship while helping you avoid common mistakes. His methods and strategies apply to any industry, income or education level. You will also learn from industry experts, entrepreneurs, CEOs, and business owners as they talk about their successes in his segment Zero to CEO. Lastly, you can hear about future technologies and space phenomena in Jason's favorite segment: Future Tech. So get ready to Strap on your Boots!
28episodes
Episodes
Newest firstAll episodes
Episode 357: How AI Is Changing Entrepreneurship Forever
2w ago00:13:03Tap to summarizeIn this episode of Strap on Your Boots, I talk about how artificial intelligence is fundamentally changing entrepreneurship, productivity, and the future of work. Over the last few years, I’ve watched the barriers to building businesses collapse in real time as AI tools dramatically accelerate research, design, marketing, coding, automation, and content creation. What once required teams of specialists can now often be prototyped by a single person working alone with the right systems and enough curiosity to experiment.I also explore the deeper implications behind this shift. While AI makes it easier to create and test ideas, it doesn’t replace judgment, taste, emotional intelligence, or experience. I discuss the growing tension between efficiency and authenticity, the psychological impact AI is having on trust online, and why human relationships and reputation may become even more valuable in a world saturated with generated content. The conversation also touches on how AI could reshape software, education, entry-level jobs, and the structure of modern companies as intelligent systems increasingly coordinate work behind the scenes.
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Episode 356: How AI Is Changing How Businesses Operate
3w ago00:14:34Tap to summarizeIn this episode of Strap on Your Boots, I talk about something that feels less theoretical by the day: the growing impact of AI on business, creativity, and everyday work. Over the past year, I’ve watched AI tools evolve from interesting experiments into practical systems that entrepreneurs and companies are quietly integrating into their daily operations. From marketing and customer support to coding, research, and content creation, AI is already reshaping how businesses function behind the scenes.I also explore the larger questions this shift creates. What happens when companies reduce entry-level hiring because software can handle repetitive tasks? How does this affect younger generations entering the workforce? And as more online content becomes algorithmically optimized and AI-assisted, why are audiences increasingly craving authenticity, personality, and real human perspective?This episode isn’t about fearmongering or blind optimism. It’s an honest conversation about the opportunities, tradeoffs, uncertainty, and cultural shifts surrounding AI right now, especially for entrepreneurs, creators, and people trying to adapt to a rapidly changing digital world.
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Episode 355: Your Guide to Building Your Dream Home in the Tropics with Peter Sandiford
4w ago00:15:49Tap to summarizeIn this episode of Zero to CEO, I speak with architect, entrepreneur, and father Peter Sandiford, who shares expert insights on how to bring your dream tropical home to life. We explore how to choose the right architect, why Caribbean modernism is on the rise, and how sustainability and technology are reshaping design in the tropics. Peter breaks down what makes a home not only beautiful, but climate-resilient, culturally rich, and built to last. If you’ve ever dreamed of building in paradise — or just want smarter, future-ready architecture — this episode is for you.
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Episode 354: How to Exit for Millions More with Mitch McGinley
May 1100:16:38Tap to summarizeIn this episode of Zero to CEO, I chat with Mitch McGinley, an Exit Planning Advisor and Business Broker specializing in boutique fitness, health, and wellness businesses. Mitch shares three simple steps to plan your ideal business exit — whether you’re looking to sell in five months or five years. We break down what buyers are really looking for, how to avoid costly mistakes, and why your exit strategy should start long before you’re ready to walk away. If you want to cash out smart and maximize your business’s value, this episode is for you.
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Episode 353: From Booked Calls to Bank with Austin Medlin
May 400:16:41Tap to summarizeIn this episode of Zero to CEO, I talk to $200K/month sales strategist Austin Medlin about why most coaches don’t actually need more leads — they need to fix how they’re closing. Austin shares the framework that’s helped over 500 coaches boost their close rates to 60–90% and scale to $50K–$100K months without relying on more ads or complicated funnels. We break down the real reason calls aren’t converting, how to train confident closers, and what a truly scalable sales system looks like. If you’re a coach or consultant with calls booked but cash not flowing, this episode is your roadmap to stronger results.
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Episode 352: The 30-Minute App Lie Nobody’s Talking About
Apr 2700:16:32Tap to summarizeIn this episode of Strap on Your Boots, I break down the reality behind the AI app-building boom and why so many founders are still struggling to get traction. While tools like Claude, Cursor, and modern cloud platforms have made it faster than ever to build apps, the real challenge hasn’t gone away — it’s shifted. I share my experience building apps over the past 30 years, how development has evolved, and why “vibe coding” isn’t a business model. We dive into the real bottleneck most people ignore: marketing, distribution, and user acquisition. If you’re building an app in today’s AI-driven world, this episode will change how you think about what actually matters.
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Episode 351: How to Scale a Service Business Without Losing Your Soul with Julie Wilson
Apr 2000:15:51Tap to summarizeIn this episode of Zero to CEO, I speak with award-winning healthcare CEO Dr. Julie Wilson about how entrepreneurs can scale a service-based business without burning out their teams or losing their core values. Julie shares how she grew Terra Nova Medical Clinics from a single practice into a 30-location healthcare network, all while maintaining quality, culture, and purpose in one of the hardest industries to scale. We discuss values-based leadership, smart growth systems, and how technology and delegation can help founders grow sustainably while staying human.
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Episode 350: How CEOs Fail with Jason Baumgarten
Apr 1300:18:04Tap to summarizeIn this episode of Zero to CEO, I speak with leading CEO advisor Jason Baumgarten about the most common ways CEOs and founders fail — and how entrepreneurs can avoid those traps early. Drawing from years of advising top executives, Jason breaks down leadership blind spots, hiring mistakes, and scaling challenges that quietly derail companies. We discuss how teams can actually make leaders better, what founders misunderstand about growth, and the decisions that separate effective CEOs from struggling ones. If you’re building, scaling, or leading a company, this episode will help you recognize failure patterns before they cost you everything.
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Episode 349: How To Build Million-Dollar Deals in Silence with Reagan Rodriguez
Apr 600:16:49Tap to summarizeIn this episode of Zero to CEO, Capital Futurist Reagan Rodriguez pulls back the curtain on the world of private capital networks and reveals how high-trust dealmakers acquire and scale businesses off the radar. As founder of the 5th Avenue Underground Club, Reagan shares how zero-down acquisitions work, why traditional funding often fails entrepreneurs, and how to tap into the hidden economy of private deal flow. If you’re looking for alternative ways to fund and grow your business, this episode is your inside pass.
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Episode 348: How to Raise and Manage Private Credit for Maximum Growth with Anthony DeBenedictis
Mar 3000:16:13Tap to summarizeIn this episode of Zero to CEO, I speak with Alternative Capital Architect Anthony DeBenedictis, Managing Partner at Avanza Capital Holdings, about how entrepreneurs can access and leverage private credit to fund and scale their businesses. Anthony explains how non-traditional capital sources can outperform traditional loans or equity funding, offering more flexibility, liquidity, and control. We discuss how to structure deals, manage risk, and build trust with private lenders, while avoiding the financial pitfalls that can cripple growing companies. If you’re ready to raise smart money and use it to grow sustainably, this episode will show you how.
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