
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

Dec 26, 2023 • 17min
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.

Dec 18, 2023 • 16min
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!

Dec 11, 2023 • 17min
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!

Dec 4, 2023 • 16min
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.

Nov 27, 2023 • 16min
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.

Nov 20, 2023 • 16min
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.

Nov 13, 2023 • 16min
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.

Nov 6, 2023 • 15min
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.

Oct 30, 2023 • 17min
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

Oct 23, 2023 • 17min
Episode 221: How to effectively revolutionize an industry with Bryan Clayton
Join me for an insightful episode with Bryan Clayton, the CEO and co-founder of GreenPal, the groundbreaking mobile app often dubbed the ‘Uber for lawn care.’ With a staggering 300,000+ active users and over $20 million in annual sales, GreenPal has revolutionized the lawn care industry. Bryan’s journey from founding Peachtree Inc., a landscaping giant with $10 million in annual revenue before its acquisition by Lusa Holdings, to his current role, is a testament to his expertise in entrepreneurialism, small business growth, marketing, and bootstrapping businesses from zero to profitability. Bryan shares invaluable strategies on using customer feedback to drive SEO, bootstrapping to eight figures, harnessing Google search for customer acquisition, and building high-performing teams. Don’t miss this chance to learn from Bryan Clayton’s remarkable success story.