HeyJaredStrap 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.
- Indexed episodes, last 90 days
- 11
- Latest publication
- Sep 14, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 6, 2026
Latest episodes
Episode 372: Investing in the AI-Driven ROAS Economy with James King (opens the original)
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In this episode of Zero to CEO, I speak with James King, founder and fund manager at ROAS Fund , about an emerging investment opportunity created by the way businesses acquire customers through platforms like Meta and Google. James explains what he calls the “ROAS economy,” how AI-driven advertising has created new inefficiencies in the market, and why measurable business revenue could become an alternative investable asset. We also discuss private credit, diversification, risk, and the lessons
Episode 371: Why Independent Filmmaking Is Easier Than Ever (opens the original)
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In this episode of Strap On Your Boots, I reflect on nearly twenty years of independent filmmaking and why I believe there has never been a better time to make a movie. Using my latest documentary, Before the Moon , as an example, I explore how affordable cinema cameras, drones, editing tools, social media, direct screenings, physical media, and digital distribution have transformed what independent filmmakers can accomplish. The technology is more accessible than ever, but the real advantage co
Episode 370: Why Investors Want Revenue, Not Just a Great Idea (opens the original)
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In this episode of Strap On Your Boots, I reflect on how startup fundraising has changed since I first entered the tech world and why I’ve become far more focused on revenue than raising capital. From growing Instamour to roughly half a million users without solving monetization early enough, to building companies today around paying customers and enterprise contracts, I explore why proving people will actually pay may be the most important validation a founder can get. Fundraising can accelerat
Episode 369: Why Five-Year Business Plans Don't Work Anymore (opens the original)
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In this episode of Strap On Your Boots, I explore why I've stopped treating five-year business plans as predictions of where a company will actually end up. After years of building startups, I've learned that customers, technology, competition, and entire markets can change faster than any spreadsheet can anticipate. I share how Vengo AI evolved from consumer to B2B SaaS to enterprise, why I now plan more specifically for the near term, and how founders can balance having a long-term direction w
Episode 368: The AI Race to Save Human Expertise with Bruce Dorey (opens the original)
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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 bus
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