Most companies don’t have a culture problem — they have a comfort problem.

In this episode, Sean sits down with Mike Krupit — former CTO, COO, and CEO turned leadership advisor and founder of Trajectify — to unpack what really happens when companies scale.

They dive into the uncomfortable transitions founders must make, why delegation is emotional (not tactical), how to manage up, and what CEOs should actually spend their time doing. Mike also breaks down why culture must evolve and how high-growth companies avoid stagnation by embracing discomfort.

If you’re leading a growing organization — or becoming the leader your company needs next — this conversation is for you.

⏱️ Chapters

00:00 – Comfort vs. Culture
Why most companies misdiagnose their real growth problem.

03:00 – From Individual Contributor to Leader
The mindset shift that derails new managers.

07:00 – Managing Up & Owning Your One-on-Ones
How to take control of your growth at any level.

12:00 – Leading in a Remote World
Overcommunication, systems, and preserving humanity.

16:30 – Founder Mode vs. CEO Mode
Why scaling requires letting go — emotionally and strategically.

19:30 – The CEO’s Four Real Jobs
Visionary, fiduciary, talent architect, and external voice.

25:00 – Evolving Culture Through Discomfort
Why hiring people “like us” limits growth.

30:00 – Vision vs. Mission
Why your mission should change more often than your vision.

33:00 – The Quadrant That’s Killing Leaders
Escaping urgency and investing in long-term growth.

🔗 Connect with Mike Krupit

🌐 Trajectify: https://www.trajectify.com

🔗 LinkedIn: https://www.linkedin.com/in/mkrupit/

🔗 No Limit Leadership

🌐 Website: https://www.nolimitleadership.com

🎙️ Podcast: https://www.nolimitleadership.com/podcast

No Limit Leadership is the go-to podcast for growth-minded executives, middle managers, and team leaders who want more than surface-level leadership advice. Hosted by executive coach and former Special Forces commander Sean Patton, this show dives deep into modern leadership, self-leadership, and the real-world strategies that build high-performing teams. Whether you're focused on leadership development, building a coaching culture, improving leadership communication, or strengthening team accountability, each episode equips you with actionable insights to unlock leadership potential across your organization. From designing onboarding systems that retain talent to asking better questions that drive clarity and impact, No Limit Leadership helps you lead yourself first so you can lead others better. If you're ready to create a culture of ownership, resilience, and results, this leadership podcast is for you.