Strap on your Boots

Jason Sherman
  • 5.0 (34)
  • ENTREPRENEURSHIP
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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!

  1. Zero to CEO: How to Build Success in Your Startup with Lem Garcia

    3D AGO

    Zero to CEO: How to Build Success in Your Startup with Lem Garcia

    In this episode of Zero to CEO, I speak with relentless legal trailblazer Lem Garcia, who turned just a few thousand dollars and a Craigslist desk into one of Southern California’s top personal injury law firms. Lem shares his journey of betting on himself, overcoming setbacks, and proving that success isn’t about where you start but how hard you’re willing to push forward. We dive into the challenges of building a business from scratch, the lessons he learned in leadership and growth, and his best advice for aspiring entrepreneurs looking to take control of their future. Whether you’re an entrepreneur, risk-taker, or simply looking for motivation, this episode is packed with powerful insights on grit, resilience, and turning ambition into success.

    15 min
  2. Zero to CEO: Zero to CEO: Design a Winning Compensation Strategy with Scott Trumpolt

    MAR 24

    Zero to CEO: Zero to CEO: Design a Winning Compensation Strategy with Scott Trumpolt

    In this episode of Zero to CEO, I speak with independent compensation consultant Scott Trumpolt about growth-driven compensation strategies for startups and business leaders. We explore how a company’s compensation philosophy impacts its success and evolves over time, highlighting the importance of building flexibility into pay structures. Scott shares insights on market-based pay, the balance between fixed and variable compensation, and how to link salaries to career architecture and job classification systems. We also discuss pay transparency methods and the key principles behind an effective compensation strategy. Tune in to learn how to design a pay system that supports business growth while attracting and retaining top talent.  Talk to Scott here.

    16 min
  3. Why 90% of Startups Fail And How to Avoid It!

    MAR 17

    Why 90% of Startups Fail And How to Avoid It!

    In this episode of Strap on Your Boots, I dive into the harsh realities of startup failure and the critical mistakes that lead to it. With 90% of startups failing, I break down the biggest reasons why, from ignoring market demand and running out of money to co-founder conflicts and poor customer engagement. Using real-world examples, I highlight what went wrong and how you can avoid the same fate. I also share lessons from my own AI B2B SaaS startup, Vengo AI, on how to stay lean, validate ideas, and build a product people actually want. If you’re an entrepreneur looking to beat the odds, this episode is packed with no-nonsense advice to help you succeed.

    16 min
  4. Future Tech: Silicon Valley’s Dirty Secret - AI is Replacing Founders

    MAR 10

    Future Tech: Silicon Valley’s Dirty Secret - AI is Replacing Founders

    Is AI going to replace entrepreneurs, or is it the ultimate tool for success? In this episode of Future Tech, I break down the impact of AI on business, exploring whether it’s a threat or an opportunity. From automating tasks to optimizing marketing and even generating business ideas, AI is transforming how we work. But can it replace human creativity, risk-taking, and leadership? I dive into real-world examples, the power of intuition, and how AI can be the ultimate co-founder for entrepreneurs. Tune in to learn how to leverage AI to build, scale, and future-proof your business!

    11 min
  5. Zero to CEO: Why Belonging at Work Matters with Dan Berger

    MAR 3

    Zero to CEO: Why Belonging at Work Matters with Dan Berger

    In this episode of Zero to CEO, I speak with hospitality entrepreneur and belonging expert Dan Berger about the true meaning of belonging and its impact inside and outside the workplace. Dan shares insights from his book The Quest, where he explores the psychology of belonging and provides a framework for building it intentionally. We discuss the difference between DEI and belonging, how they intersect, and the role workplaces play in fostering real connections versus surface-level inclusivity. Dan also shares his experience designing spaces and experiences that help small teams cultivate deeper connections and a sense of shared purpose. Tune in for a thought-provoking conversation on how belonging shapes our lives and careers.

    17 min
  6. Zero to CEO: Bold Solutions to the World's Biggest Problems with Mitch Francis

    FEB 24

    Zero to CEO: Bold Solutions to the World's Biggest Problems with Mitch Francis

    In this episode of Zero to CEO, I speak with visionary entrepreneur, innovator, and author Mitch Francis about bold solutions to some of the world’s biggest challenges. Drawing from his new book, Bad-Ass Solutions for Today’s Big-Ass Problems, Mitch shares practical and non-partisan ideas for tackling issues like climate change, national debt, education reform, gun control, and more. With years of experience leading successful businesses across multiple industries, he offers a fresh, real-world perspective on solving problems that matter. Tune in for an eye-opening discussion on creative, actionable solutions that could reshape the future.

    17 min
  7. Transforming Financial Services and Leadership with Matt Logan

    FEB 17

    Transforming Financial Services and Leadership with Matt Logan

    In this episode of Zero to CEO, I speak with Matt Logan, Founder of Rise North Capital, about his mission to transform the financial services industry. With over 16 years of experience, Matt shares how he empowers financial professionals to thrive, expands access to financial advice, and creates lasting impact for clients. We explore his innovative leadership strategies, the art of building successful teams, and his personal journey of balancing a fulfilling career with his passions for drumming, fitness, and family. This conversation is packed with actionable insights and inspiration for leaders, financial professionals, and anyone striving to make a meaningful difference.

    16 min
  8. Zero to CEO: Building Startup Success and Customer Value with Robert McMillan

    FEB 10

    Zero to CEO: Building Startup Success and Customer Value with Robert McMillan

    In this episode of Zero to CEO, I speak with Robert McMillan, founder of Camping.Tools, about crafting value for both B2C and B2B customers in the digital age. We explore the challenges startups face when creating the perfect customer pitch and the importance of identifying market pain points to deliver meaningful solutions. Robert shares insights on where to begin, learning through trial and error, adopting a process-driven approach, building a strong network, and the power of taking decisive action. Join us for a conversation packed with practical advice for entrepreneurs and innovators.

    16 min
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5
out of 5
34 Ratings

About

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!

Information

  • Creator
    Jason Sherman
  • Years Active
    2018 - 2025
  • Episodes
    298
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Jason Sherman
  • Show Website
    Strap on your Boots

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