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    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!

    en-usJason Sherman243 Episodes

    Episodes (243)

    Episode 241: Zero to CEO: How entrepreneurs can own established online businesses with Mike Vranjkovic

    Episode 241: Zero to CEO: How entrepreneurs can own established online businesses with Mike Vranjkovic

    In this engaging episode of Zero to CEO, I sit down with Mike Vranjkovic, an online business expert, to unpack the intricacies of owning established online businesses. Mike shares his insights from WebStreet, a platform that not only equips successful online entrepreneurs with the capital to elevate their businesses to 8-figure revenues but also offers accredited investors golden opportunities to invest passively in established online ventures. We dive deep into the strategies for leveraging investor funds to scale internet businesses, analyze the latest trends and opportunities in the online business sector for 2024 and beyond, and reveal how online ventures can become lucrative passive investment avenues. Mike also sheds light on acquiring a portfolio of online businesses and the potential for entrepreneurs to own established online businesses with significant growth potential, even without prior internet business skills or time to run the business. This episode is a treasure trove of wisdom for anyone looking to navigate the rewarding path of online entrepreneurship and investment.

    Episode 240: Zero to CEO: Empowering underrepresented founders and entrepreneurs with Luke Diaz

    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. 

    Episode 239: Zero to CEO: Why Non-Food Franchise Opportunities are so Popular with Jon Ostenson

    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.

    Episode 238: Zero to CEO: Mastering the Pressure of Leadership with Steve Tashjian

    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.

    Episode 237: 5 Reasons Why Building a Startup Today is Different from 10 Years Ago

    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.

    Episode 236: Future Tech: Where AI is Headed in the Next 5 Years

    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.

    Episode 235: 5 Simple steps in building your passive income machine with Paul Halme

    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.

    Episode 234: Zero to CEO: Mastering Workers' Comp for Business Success with Kevin Ring

    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.

    Episode 233: Double Your Website Revenue with Michael Buzinski

    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.

    Episode 232: Rewriting the Rules of Being an Author with Michael DeLon

    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.

    Episode 231: Zero to CEO: The Path to Franchise Ownership with Greg Mohr

    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.

    Episode 230: Zero to CEO: Elevating CEO and C-Suite Dynamics with Margie Oleson

    Episode 230: Zero to CEO: Elevating CEO and C-Suite Dynamics with Margie Oleson

    In this episode of Zero to CEO I have a conversation with Margie Oleson, Founder and CEO of Oleson Consulting, about various topics including CEO and C-Suite coaching for women entrepreneurs, and companies undergoing mergers, acquisitions, or other major changes. We delve into the art of becoming a high-performing leader, leading an effective leadership team, and building a cohesive, high-performing group within a company. The episode also covers stories of triumph and empowerment for women CEOs, strategies for achieving peak CEO performance, and Margie’s unique insights on elevating team dynamics and leadership excellence.

    Episode 229: Zero to CEO: How to distill messages that engage VC partners with Davina Stanley

    Episode 229: Zero to CEO: How to distill messages that engage VC partners with Davina Stanley

    Join me for an insightful episode of Zero to CEO featuring Business Communication Expert Davina Stanley, as we explore the art of message distillation and its impact on senior leaders, boards, and VC partners. Discover valuable strategies to enhance your communication skills, including the importance of speed in reading, insights into the human brain, and the role of effective editing tools. In this episode, we’ll dive deep into the world of startup growth hacking and provide you with the knowledge to transform your approach to decision-making and communication. Don’t miss out on this enlightening discussion that’s sure to elevate your entrepreneurial journey. Tune in now!

    Episode 228: Future Tech: Unveiling the Power of AI and Originality with Jonathan Gillham

    Episode 228: Future Tech: Unveiling the Power of AI and Originality with Jonathan Gillham

    In this episode of Future Tech, I speak with Jonathan Gillham, the Founder and CEO of Originality.AI, about the groundbreaking role of artificial intelligence in the realms of content creation and verification. Launched in November 2022, before the advent of ChatGPT, Originality.AI was driven by Jonathan’s foresight into the transformative wave of generative AI, which he leveraged for SEO through his agency. With the full unleashing of ChatGPT and GPT-4, Jonathan’s insight into the necessity for a contemporary plagiarism checker has culminated in Originality.AI, featuring advanced functionalities including scan history, detection scores, shareable results, and team access. Find out why my startup Spinnr became one of the first customers of Originality.AI in this episode!

    Episode 227: Zero to CEO: Insights on AI and the media landscape with Alex Fink

    Episode 227: Zero to CEO: Insights on AI and the media landscape with Alex Fink

    In this episode of Zero to CEO, I am joined by Alex Fink, an AI pioneer and the founder and CEO of the Otherweb. Delve into the pressing issues of journalism and media in the digital age as Alex passionately discusses the challenges and potential solutions, using technology as a powerful ally. Join us for an engaging conversation that explores mindful internet navigation, the role of AI in information filtering, the responsibilities of tech companies, the trustworthiness of AI, and the reasons behind the decline in media quality in today’s interconnected world.

    Episode 226: Zero to CEO: Inspiring entrepreneurship and overcoming failures with John St.Pierre

    Episode 226: Zero to CEO: Inspiring entrepreneurship and overcoming failures with John St.Pierre

     In this episode of Zero to CEO, I have a compelling conversation with accomplished entrepreneur and author John St. Pierre. With a remarkable 25-year journey filled with both successes and valuable lessons from failures, John shares his insights on moving from CEO to Chairperson, the importance of protecting equity and building capital for self-financing growth, and the seven principles for entrepreneurial success from his book “The $100M Journey.” We delve into the transformation of a business from a lifestyle venture to a high-performance entity, enabling the creation of wealth and freedom. John also offers valuable advice on fostering a culture of intrapreneurship within your organization to strategically elevate your business. 

    Episode 225: 6 superpowers you need for entrepreneurial success with Iva Paleckova

    Episode 225: 6 superpowers you need for entrepreneurial success with Iva Paleckova

    In this insightful episode, we dive into the dynamic world of entrepreneurship with Iva Paleckova, a mindset and strategy coach who defies all odds. Iva takes us through her remarkable transformation from a single mother to a seven-figure entrepreneur in just 18 months. She shares the six essential superpowers that she believes are crucial for entrepreneurial success. Throughout the conversation, Iva reflects on her journey, discussing the pivotal moments and the greatest mistakes she's made and observed in others. We unravel the formula that took her from the brink of financial despair to thriving success, probing into the reasons why many budding entrepreneurs give up on their ventures. Additionally, Iva introduces us to The Break Free Process, her unique strategy designed to empower struggling entrepreneurs to overcome their hurdles and achieve their business goals. This episode is a treasure trove of real-life experiences, practical wisdom, and transformative advice for anyone looking to make their mark in the business world.

    Episode 224: Zero to CEO: Ditching VC Safety Nets and Finding Your Startup's North Star with Paul Bianco

    Episode 224: Zero to CEO: Ditching VC Safety Nets and Finding Your Startup's North Star with Paul Bianco

    In this episode of Zero to CEO I engage in an insightful conversation with accomplished entrepreneur and visionary Paul Bianco, exploring the intricacies of financial navigation in the world of entrepreneurship. Gain valuable insights into ditching the traditional VC safety net and thriving without a Harvard MBA. Discover the crucial pre-launch question that can steer your startup toward success, learn from Paul’s personal founder journey, and receive practical recommendations for building a rewarding entrepreneurial career. Finally, delve into the importance of defining your startup’s North Star as the foundational step toward building a thriving business. Join us for an enlightening discussion on financial resilience and entrepreneurial excellence.

    Episode 223: How to build a business strategy in 3 simple steps with Alex Brueckmann

    Episode 223: How to build a business strategy in 3 simple steps with Alex Brueckmann

    In this episode, I’m joined by Alex Brueckmann, a strategy entrepreneur and author, who shares valuable insights on how to construct a robust business strategy in three simple steps. We delve into the mindset shift that entrepreneurs must master, the limitations of seeking answers solely in marketing courses, and the importance of aligning business strategies with purpose for a better world. Join me as we explore Alex’s journey, which began with the birth of his child in early 2020 and a move from Germany to Canada amidst lockdown conditions, leading to the inception of his new business venture under rather unconventional circumstances.

    Episode 222: Zero to CEO: Hidden strategies to exponentially grow your business with Brooke Lively

    Episode 222: Zero to CEO: Hidden strategies to exponentially grow your business with Brooke Lively

    In this episode of Zero to CEO, we delve deep into the world of entrepreneurship alongside Chartered Financial Analyst (CFA) and seasoned entrepreneur, Brooke Lively. Together, we unveil the hidden strategies utilized by successful business leaders to propel their ventures to new heights, including Brooke’s pivotal role in catapulting a startup from ground zero to achieving seven-figure revenues in under two years. Our engaging conversation covers covert tactics employed by top entrepreneurs for exponential growth, strategies for harmonizing personal, professional, and financial goals with business expansion, insights on gracefully exiting a business with a sense of fulfillment, and the critical decision-making process between hiring in-house help and partnering with fractional CFO companies. Join us for a deep dive into the world of business growth, strategies, and achieving your entrepreneurial dreams. To try Brooke’s Profit Finder head over to: https://www.cathcap.com/zerotoceo