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!
34episodes
Episodes
Newest firstAll episodes
Episode 363: Why Building Great Software Isn't Enough
1w ago00:15:15Tap to summarizeIn this episode of Strap On Your Boots, I reflect on one of the biggest lessons I've learned after building multiple software companies: creating a great product is no longer the hardest part of entrepreneurship. As software becomes easier to build with AI and modern development tools, the real challenge has shifted to earning attention, finding the right customers, and standing out in an increasingly crowded market. I also share why I pivoted from chasing thousands of SaaS subscribers to pursuing enterprise clients, and how changing the customer completely changed the business.
Transcribe →
Episode 362: Why High-Achievers Burn Out with Naomi Scott
2w ago00:19:03Tap to summarizeIn this episode of Zero to CEO, I speak with leadership coach and somatic practitioner Naomi Scott about why so many high-performing entrepreneurs burn out — even after achieving success. Naomi explains how burnout isn’t a willpower problem, but a nervous system problem, and why the same drive that helps founders succeed can actually prevent them from sustaining growth. We dive into the biology behind burnout, how childhood patterns show up in leadership, and what it really takes to build a business that doesn’t destroy your health. If you’ve ever felt like you’re winning on the outside but running on fumes internally, this episode will help you rewire how you operate and lead.
Transcribe →
Episode 361: How to Choose Your Next Big Project
3w 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.
Transcribe →
Episode 360: Virtual Appointments That Convert High-Ticket Buyers with Allan Khazak
Jun 2200:16:56Tap 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.
Transcribe →
Episode 359: Have We Been Thinking About Entrepreneurship All Wrong?
Jun 1500:16:18Tap 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.
Transcribe →
Episode 358: How to Actually Make Money with AI with Issac Hicks
Jun 800:16:08Tap 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.
Transcribe →
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.
Transcribe →
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.
Transcribe →
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.
Transcribe →
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.
Transcribe →