Strap on your Boots

Hosted by Jason Sherman

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Episodes

370

Latest episode

Aug 2026

Language

EN-US

About the show

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! ]]>

Listen to episodes

60 recent

August 17, 2026Episode 36816 min

Episode 368: The AI Race to Save Human Expertise with Bruce Dorey

In this episode of Zero to CEO, I speak with Dr. Bruce Dorey , leadership expert, executive coach, and engineering CEO, about one of the biggest challenges organizations face today: preserving decades of institutional knowledge before it walks out the door. We discuss why experience is far more valuable than documentation alone, how mentorship and coaching help develop future leaders, and how AI can capture and scale human expertise without replacing the people behind it. If you’re leading a business or preparing your organization for the future, this conversation offers practical insights you can apply today.

August 10, 2026Episode 36720 min

Episode 367: Why Small Companies Can Beat Big Companies

In this episode of Strap On Your Boots , I explore one of the biggest advantages startups have over much larger competitors: speed. Drawing from my experience building companies and the evolution of Vengo AI from a consumer product to B2B SaaS and eventually enterprise, I explain how small teams can listen to customers, test ideas, pivot, and respond to the market incredibly quickly. Large companies may have more money, people, and resources, but all of that size comes with organizational weight. Sometimes the startup that can adapt in days has an advantage that money simply can’t buy.

August 3, 2026Episode 36616 min

Episode 366: Why Experience Is the Ultimate Startup Advantage

In this episode of Strap On Your Boots , I reflect on turning fifty and the biggest lesson I've learned after decades of building startups, making films, writing software, and exploring new ideas. Experience isn't just about accumulating knowledge. It's about developing judgment, recognizing patterns, and connecting lessons from projects that once seemed completely unrelated. I share how curiosity, failure, and continuous learning have shaped every stage of my career, and why your greatest advantage as an entrepreneur may be the experiences you've already lived through.

July 27, 2026Episode 36517 min

Episode 365: Why Success Without Purpose Leaves People Empty with Bryan Blakeny

In this episode of Zero to CEO, I speak with Bryan Blakeny, therapist, counselor, and founder of EQ Education , about why so many successful people still struggle to find fulfillment. After more than 26 years working in psychology, counseling, and personal development, Bryan has spent his career helping people understand the deeper connection between purpose, identity, emotional well-being, and long-term happiness. Our conversation explores why achievement and success don’t always lead to fulfillment, how spiritual intelligence influences mental health, and why many people feel disconnected despite accomplishing their goals. Bryan shares his perspective on the growing influence of pop psychology, the dangers of self-diagnosis culture, and the importance of developing wisdom alongside knowledge. We also discuss practical approaches to discovering purpose, navigating life’s challenges, and creating a stronger sense of meaning in both personal and professional life. Whether you’re building a business, leading a company, or searching for greater clarity in your own journey, this episode offers valuable insights into what it truly means to live a purposeful and fulfilling life.

July 20, 2026Episode 36416 min

Episode 364: Build the Vision Before You Build the Team

In this episode of Strap On Your Boots , I share one of the biggest mindset shifts I’ve had as an entrepreneur: why I stopped searching for the perfect co-founder and started focusing on building the vision first. Looking back at my early startups, I realized that talented people alone aren’t enough if everyone has a different picture of where the company is headed. I explain how building prototypes, attracting early users, and creating momentum on my own helped me find teammates who believed in the vision instead of helping define it. If you’ve been waiting for the right partner before getting started, this episode may change how you think about launching your next company.

July 13, 2026Episode 36315 min

Episode 363: Why Building Great Software Isn't Enough

In 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.

July 6, 2026Episode 36219 min

Episode 362: Why High-Achievers Burn Out with Naomi Scott

In 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.

June 29, 2026Episode 36119 min

Episode 361: How to Choose Your Next Big Project

In 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.

June 22, 2026Episode 36016 min

Episode 360: Virtual Appointments That Convert High-Ticket Buyers with Allan Khazak

In 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.

June 15, 2026Episode 35916 min

Episode 359: Have We Been Thinking About Entrepreneurship All Wrong?

In 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.