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!
32episodes
Episodes
Newest firstAll episodes
Episode 361: How to Choose Your Next Big Project
3d ago00:19:05Tap to summarizeIn this episode of Strap On Your Boots, I answer one of the questions I get asked most often How do you decide what to work on next Looking back on a career that spans startups, AI, filmmaking, music, writing, and entrepreneurship, I share the framework that naturally emerged over the years. I discuss why I rotate between creative and technical projects, how curiosity shapes my decisions, why timing matters just as much as the idea itself, and how AI has become an invaluable tool for challenging assumptions before I commit to building something new.
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Episode 360: Virtual Appointments That Convert High-Ticket Buyers with Allan Khazak
1w ago00:16:56Tap to summarizeIn this episode of Zero to CEO, I speak with Founder and CEO Allan Khazak about why most high-ticket teams don’t have a lead problem — they have a broken conversion process. Allan breaks down the exact system he uses to help insurance producers, advisors, and service-based businesses increase show rates, reduce no-shows, qualify faster, and close based on economic outcomes instead of product pitches. We dive into building an owned, compliant pipeline that works remotely and drives consistent, scalable revenue — without relying on purchased leads or massive recruiting teams. If you sell high-ticket services and want predictable booked appointments that actually convert, this episode is for you.
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Episode 359: Have We Been Thinking About Entrepreneurship All Wrong?
2w ago00:16:18Tap to summarizeIn this episode of Strap On Your Boots, I reflect on how startup culture shaped my view of entrepreneurship and why I recently found myself questioning one of my own assumptions. After learning about entrepreneurs who buy existing businesses instead of building companies from scratch, I began wondering whether we’ve become too attached to a single version of what entrepreneurship is supposed to look like. I share lessons from my own journey building startups and explore why sustainability, execution, and long-term value creation may deserve just as much attention as innovation and growth.
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Episode 358: How to Actually Make Money with AI with Issac Hicks
3w ago00:16:08Tap to summarizeIn this episode of Zero to CEO, I speak with Technology and Operations Expert Issac Hicks about why most AI projects fail — and how entrepreneurs can be part of the small percentage that actually generate real returns. Issac breaks down the gap between AI marketing hype and operational reality, explains why nearly 95% of AI initiatives never make money, and shows what successful AI implementations really look like inside growing businesses. If you’re tired of gimmicks and want to understand how AI can truly drive revenue, efficiency, and scale, this episode is a must-listen.
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Episode 357: How AI Is Changing Entrepreneurship Forever
Jun 100:13:03Tap 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
May 2500:14:34Tap 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
May 1800:15:49Tap 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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