How One Man’s Relentless Drive Built the World’s Fastest-Growing Productivity Company | Chris Cunningham
The Coaches Room with Coach Kav
Release Date: 10/22/2025
It’s not "My Mission to Inspire. I just want to be a superhero | Jimmy House
The Coaches Room with Coach Kav
In this conversation, Coach Kav interviews Jimmy House, a strength and conditioning coach and professional wrestler, about his journey in sports, the influence of Bill Goldberg, and his aspirations in professional wrestling. They discuss the importance of mentorship, overcoming obstacles, and the role of faith in achieving goals. Jimmy shares his desire to inspire the next generation and the significance of emotional control in personal growth. Takeaways • Jimmy's journey began at a young age with his father's influence in strength training. • He has a diverse background in sports...
info_outline
The Octopus Whisperer: Warren Carlyle's Journey Building a Community Around Octopuses
The Coaches Room with Coach Kav
In this conversation, Warren Carlyle. shares his journey from a curious child with a passion for octopuses to the founder of OctoNation, the world's largest octopus fan club. He discusses the importance of community building, collaboration, and creating impact through education and awareness. Warren emphasizes the significance of clarity, core values, and content creation in building a fanatical community. He also addresses the challenges of navigating potential and the importance of authenticity and ethics in branding. The conversation concludes with insights on passion, purpose, and the role...
info_outline
The "Trust" Mistake 99% Of Leaders Make! Why Being Late Is Destroying Your Business & Relationships | Blake Eastman
The Coaches Room with Coach Kav
In this engaging conversation, Coach Kav and Blake Eastman explore the intricacies of human behavior, communication, and leadership. They discuss Blake's unique journey from poker to psychology, emphasizing the importance of understanding nonverbal cues and cultural nuances in effective communication. The dialogue highlights the role of self-awareness, trust, and accountability in leadership, as well as the impact of data and AI in enhancing interpersonal interactions. Ultimately, they advocate for creating safe spaces for honest conversations and optimizing meetings for better outcomes. ...
info_outline
Navigating the Complexities of Communication | Michael Martocci
The Coaches Room with Coach Kav
In this conversation, Michael shares his entrepreneurial journey, discussing the founding and growth of Swag Up, the importance of employee engagement, and the role of technology in business operations. He emphasizes the need for quality merchandise, consistency in branding, and the significance of self-awareness in leadership. The discussion also touches on the balance between entrepreneurship and family life, and the value of continuous learning and personal growth. Takeaways 1. The loudest person isn’t always the most impactful. Some people build their influence quietly—through...
info_outline
This Is Why Most People Fail in the AI Era | Jonathan Mast
The Coaches Room with Coach Kav
In this episode, Coach Kav sits down with AI educator and creator Jonathan Mast for one of the most practical and eye-opening conversations about the future of work, coaching, and human performance. Jonathan breaks down what most people still get wrong about AI, why the real competitive edge isn’t the tool but the thinking behind the tool, and how anyone can use AI to become faster, clearer, and more effective in their career or business. Together, they explore the mindset shifts required to stay relevant, the truth about AI adoption, why courage beats confidence, and how the “Perfect...
info_outline
I Stand Against the Need to Be Understood | Nick Mayhugh
The Coaches Room with Coach Kav
In this conversation, Nick Mayhugh shares his inspiring journey of overcoming the challenges posed by cerebral palsy, his experiences with seizures, and the impact of his diagnosis on his athletic career. He discusses the importance of mental resilience, the support from family and coaches, and his transition from soccer to track. Nick reflects on his success at the Tokyo Paralympics, the advocacy work he is passionate about, and his aspirations for the future. Throughout the discussion, he emphasizes the significance of believing in oneself and the power of sharing one's story to inspire...
info_outline
The Leadership Lessons from the Batter's Box | Brandon Eaton
The Coaches Room with Coach Kav
What if our deepest-held beliefs about "failure" are all wrong? And what if the flaw we see in ourselves isn't a weakness, but the very engine of our success? My guest today is Brandon Eaton, the CEO and co-founder of the 10-year sporting goods brand, Stinger Sports. But this conversation isn't about business, it's about the "why" behind it. Brandon's entire company was built from a painful childhood observation: watching talented kids get "priced out" of the game they loved . He built his life's work on a promise to fight for them. This is one of the most honest conversations I've ever had...
info_outline
Simplicity Is the Highest Form of Mastery | Junaid Ahmed
The Coaches Room with Coach Kav
This conversation explores the critical importance of first impressions in communication, particularly in video content. It emphasizes how quickly audiences make decisions about their engagement and the role of brand presence in capturing attention. Takeaways: The average person takes three seconds to make a decision. First impressions are crucial in retaining audience attention. Brand presence significantly influences viewer engagement. Clarity in communication enhances audience connection. Video content must be engaging from the start. Understanding audience behavior is key to...
info_outline
Pressure Reveals Who You Really Are | Ari Meisel
The Coaches Room with Coach Kav
In this episode Ari Meisel sits down with Coach Kav for a wide-ranging conversation about how high performance actually gets made not in moments of comfort, but under pressure and constraint. They trace the practical architecture of effectiveness (optimize → automate → outsource), the difference between productivity and true effectiveness, and why asynchronous communication and disciplined boundaries create space for real impact. Personal stories from building a house with limited resources to EMS leadership and the muscle of saying “no” puncture the theory with lived, actionable...
info_outline
How One Man’s Relentless Drive Built the World’s Fastest-Growing Productivity Company | Chris Cunningham
The Coaches Room with Coach Kav
Chris Cunningham’s journey reads like a startup fairytale but lived like a war story. From a small town in Martinsville, Virginia, Chris went from managing his father’s tire shop to living in a Palo Alto house full of dreamers building a platform that would redefine how the world works. This episode is a masterclass in grit, reinvention, and relationship capital. Chris opens up about risking it all to build ClickUp, how he helped create one of the most viral tech marketing campaigns (“Cut the Slack”), and why being a “super-connector” is his real superpower. It’s a story of...
info_outlineChris Cunningham’s journey reads like a startup fairytale but lived like a war story.
From a small town in Martinsville, Virginia, Chris went from managing his father’s tire shop to living in a Palo Alto house full of dreamers building a platform that would redefine how the world works.
This episode is a masterclass in grit, reinvention, and relationship capital. Chris opens up about risking it all to build ClickUp, how he helped create one of the most viral tech marketing campaigns (“Cut the Slack”), and why being a “super-connector” is his real superpower.
It’s a story of obsession not with fame or money but with excellence, speed, and doing right by people.
In a world where social media is saturated with noise, Chris reveals how authenticity, raw storytelling, and community still win.
This isn’t just about building software.
It’s about building something that lasts.
Takeaways
Speed is the new superpower — in tech and communication, slow systems kill innovation.
Obsession beats motivation — you must trick your mind into loving the grind.
Relationships are your real equity — every connection expands your world.
The new marketing isn’t perfection — it’s rawness. Authentic, imperfect stories connect deeper.
Celebrate solving problems, not raising money. Real success is earned, not announced.
You are the brand. Whether in B2B or B2C, personality drives growth more than products.
Timestamp:
00:00 — From Small Town to Silicon Valley: The Early Hustle
06:30 — Losing It All to Build Something Bigger
10:15 — The Power of Environments That Challenge You
13:00 — The Art of Connection: Why Relationships Are the Real ROI
17:45 — The Power of Proximity and the Miami Network
24:00 — Building ClickUp: Obsession, Failure, and the Underdog Mindset
27:30 — Innovation, AI, and the Next Chapter of Work
31:15 — The New Era of B2B Storytelling
35:00 — Superpowers, Flaws, and the Psychology of Obsession
38:00 — Final Reflections: What It Means to Build Something That Lasts
Follow Chris:
LinkedIn: https://www.linkedin.com/in/chrisclickup?utm_source=chatgpt.com
Instagram: https://www.instagram.com/cunningham/
Facebook: https://www.facebook.com/CHAMMMMER/
Follow Coach Kav:
LinkedIn: https://www.linkedin.com/in/justin-kavanaugh-80629682/
Instagram: https://www.instagram.com/coachkav/
Facebook: https://www.facebook.com/coachkav/
Youtube: https://www.youtube.com/@TheCoachesRoomWithCoachKav