Strap on your Boots

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!

Strap on your Boots is a business podcast hosted by Jason Sherman, with 370 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jason Sherman hosts Strap on your Boots, a business show with 370 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #368

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

  Aug 17, 202616 min

  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.

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  Episode #367

  Episode 367: Why Small Companies Can Beat Big Companies

  Aug 10, 202620 min

  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.

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  Episode #366

  Episode 366: Why Experience Is the Ultimate Startup Advantage

  Aug 3, 202617 min

  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.

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  Episode #365

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

  Jul 27, 202617 min

  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.

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  Episode #364

  Episode 364: Build the Vision Before You Build the Team

  Jul 20, 202617 min

  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.

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