
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!
Latest episodes

Mar 4, 2024 • 17min
Episode 240: Zero to CEO: Empowering underrepresented founders and entrepreneurs with Luke Diaz
In this enlightening episode of Zero to CEO, I have the pleasure of talking to Luke Diaz, a visionary entrepreneur and angel investor dedicated to empowering underrepresented founders through his initiative, DBT (Do Big Things) Ventures. Luke shares his experiences and insights into the world of angel and venture investments, focusing on how DBT Ventures supports underrepresented entrepreneurs with investments ranging from $25K to $250K. We delve into the critical role of angel and venture capital in leveling the playing field for startups led by underrepresented founders, discussing the methodologies to evaluate startups for investment, effective fundraising strategies to raise awareness, and the importance of conscious leadership in new business ventures. Additionally, Luke offers valuable advice on accelerating product adoption, driving tangible business outcomes for customers, and achieving unparalleled customer retention rates. This episode is a treasure trove of knowledge for any entrepreneur looking to make a meaningful impact in the startup ecosystem.

Feb 26, 2024 • 15min
Episode 239: Zero to CEO: Why Non-Food Franchise Opportunities are so Popular with Jon Ostenson
In this compelling episode of Zero to CEO, I sit down with Jon Ostenson, a leading expert in the franchise consulting space, to delve into the burgeoning popularity of non-food franchise opportunities. As business ownership and investment interest reach unprecedented levels, many aspiring entrepreneurs and investors remain unaware of the extensive array of possibilities that lie beyond the conventional food industry. Throughout our discussion, we explore why these non-food franchises are resonating so strongly with today’s market, offering listeners an in-depth look at who is investing in these opportunities, their motivations, and what exactly they’re investing in. With Jon’s expert insights, we also dissect the advantages and drawbacks of franchising compared to starting a business from scratch, the feasibility of operating franchises on a passive or semi-passive basis, and the critical financial considerations including cost, revenue, and profit potential. Moreover, we provide actionable advice on how to navigate the selection process to find the right franchise that aligns with one’s goals and aspirations, making this episode a must-listen for anyone considering a venture into the franchise world.

Feb 19, 2024 • 17min
Episode 238: Zero to CEO: Mastering the Pressure of Leadership with Steve Tashjian
In this episode of Zero to CEO, I sit down with Steve Tashjian, a renowned High-Performance Coach, to delve into the secrets behind achieving under pressure and the defining traits of high performers and high-performing organizations. Steve shares his unique perspective on leadership and the dynamics of high-performing teams, drawing from his extensive experience in preparing the youngest-ever American team for the Men’s World Cup in Qatar 2022. Through engaging stories and expert advice, we explore how to combat groupthink within elite organizations, the importance of resilience, and strategies for maintaining excellence in varying environments. Join us as we uncover the keys to sustaining high performance in the face of challenges.

Feb 12, 2024 • 14min
Episode 237: 5 Reasons Why Building a Startup Today is Different from 10 Years Ago
In this insightful episode of Strap on your Boots, Jason dives deep into the transformative shifts that have reshaped the startup landscape over the last decade. From the digital evolution and funding frenzy to the rise of big data, the pivot towards niche markets, and the cultural embrace of entrepreneurship, Jason unpacks how these changes have created new challenges and opportunities for today's tech entrepreneurs. Drawing on his own rich experience as an innovator, filmmaker, and tech expert, Jason offers a compelling narrative that blends personal anecdotes, expert analysis, and actionable advice. Whether you're an aspiring entrepreneur, a tech enthusiast, or just curious about the startup world, this episode offers valuable insights into navigating the dynamic terrain of modern tech entrepreneurship.

Feb 5, 2024 • 15min
Episode 236: Future Tech: Where AI is Headed in the Next 5 Years
Join me in this captivating episode of Future Tech as I embark on a journey to explore where AI is headed in the next five years. Delve into the fascinating world of artificial intelligence, from the looming singularity to its transformative impact on jobs, healthcare, education, and even the arts. I blend expert insights with vivid examples, discussing both the potential and challenges of AI in our rapidly evolving world. Whether you're an AI enthusiast, a curious listener, or someone passionate about technology's role in shaping our future, this episode offers a thought-provoking and comprehensive look at the AI landscape. Tune in for an enlightening exploration of how AI is set to redefine humanity, enhance our daily lives, and propel us into an exciting era of Humankind 2.0.

Jan 29, 2024 • 15min
Episode 235: 5 Simple steps in building your passive income machine with Paul Halme
In this episode of Strap on your Boots I speak to Paul Halme, a best-selling author, international speaker, financial advisor, and Brazilian Jiu-Jitsu world champion. Paul is known as the secret weapon among entrepreneurs, a title he’s earned through his exceptional skills in creating high 6-figure offline businesses for his clients. As a former stockbroker who transformed his business into one of the most successful gyms in the US, Paul is uniquely positioned to offer insights in his podcast “5 Simple Steps in Building Your Passive Income Machine.” This podcast delves into whether passive income is truly attainable, the importance of building it now, how to eliminate limiting money beliefs, the best ways to start investing, and a comprehensive guide through the five steps of building your passive income machine. His wealth of experience and proven track record make this podcast an invaluable resource for anyone looking to navigate the world of financial growth and investment.

Jan 22, 2024 • 16min
Episode 234: Zero to CEO: Mastering Workers' Comp for Business Success with Kevin Ring
In this episode of Zero to CEO, I have an enlightening conversation with Lead Workers’ Compensation Analyst Kevin Ring, where we delve into the intricacies of workers’ compensation and explore strategies for employers to run more successful programs. Kevin, with his extensive experience and over 1200 experience mod worksheet analyses, shares insights on how employers, especially in blue/grey-collar industries, can navigate the often-misunderstood realm of workers’ compensation. He dispels the myth that workers’ comp is a non-negotiable cost and highlights ways to foster better employee relationships and a more profitable business. We cover a range of topics, from understanding the purpose and legalities of workers’ comp from an employer’s perspective, to practical tips on business classification, accurate premium audits, and effective handling of injured employees. Join us as we uncover how businesses can assert control over their workers’ comp expenses without compromising on the quality of their insurance coverage.

Jan 15, 2024 • 16min
Episode 233: Double Your Website Revenue with Michael Buzinski
In this episode of Strap on your Boots I’m we’re joined by digital marketing thought leader Michael Buzinski, who delves into the essential steps to double website revenue for service-based businesses. Michael emphasizes the critical importance of website marketing for entrepreneurs in today’s digital landscape. He introduces listeners to the Rule of 26, explaining its significance and how entrepreneurs can leverage it. Further, he discusses ARPC (Average Revenue Per Customer) and strategies to increase it by 26%. The episode also features two actionable items that can immediately enhance your website’s conversion rate. Moreover, Michael sheds light on the idea that not all traffic is beneficial, offering insights on how to maximize your website’s traffic potential for optimal results. A fun fact about our guest, Michael Buzinski, is his background as a professional Jazz Trombonist, which he began at the age of 13.

Jan 8, 2024 • 15min
Episode 232: Rewriting the Rules of Being an Author with Michael DeLon
Join me on the latest episode of Strap on your Boots, where I sit down with Michael DeLon, a marketing coach and book publisher, to delve into the unconventional pathways of authorship and entrepreneurship. Michael shares his captivating journey from feeling entrapped in a metaphorical “prison” to finding liberation through the power of publishing. He challenges the traditional notion that business owners must pen their books, drawing from his own transformative experience with his first book, “On Marketing.” Michael also demystifies his advice to entrepreneurs on why they shouldn’t be a “coffee bean” and introduces us to his innovative Credibility Calculator. Plus, don’t miss the intriguing anecdotes about his daring skydiving adventure and the reactions that leave his audience utterly astonished. Tune in for an episode that promises to ignite your curiosity and inspire you to rethink the way you tell your story.

Jan 1, 2024 • 16min
Episode 231: Zero to CEO: The Path to Franchise Ownership with Greg Mohr
In the episode of Zero to CEO, I have the pleasure of talking to Greg Mohr, a WSJ Bestselling Author and the brain behind Franchise Maven®, as we delve into the intricacies of franchise ownership. Greg outlines a straightforward, three-step process designed for budding entrepreneurs eager to kickstart their business ventures without the overwhelming burden or the paralyzing uncertainty that often accompanies such undertakings. This episode is a treasure trove of insights, offering guidance on how to embark on the franchise owner path, understanding the trade-offs between time and monetary investments across various engagement levels from full time to semi-absentee or even absentee ownership. We discuss the critical pitfalls to avoid when selecting a franchise, explore the different types of franchise structures including single, area developer, and master developer options, as well as the growth strategies whether vertical or horizontal. Additionally, we delve into the various ways of financing your franchise, from 401K rollovers and SBA loans to other financial avenues, ensuring you have the knowledge to make your franchising journey as smooth and successful as possible.Contact Greg here.