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 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