Ever wondered why your business feels stuck in chaos—no matter how innovative your big idea is? Here’s the shocker: The real bottleneck might be you.

In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Jhana Li, operations expert and founder of Spyglass Ops, who shares how even the most visionary entrepreneurs can unintentionally hold their businesses back. Jhana reveals why the skills that get you started—wearing all the hats, holding the reins tight—are the same habits that keep your company from reaching the next level of growth.

Key Highlights:

• Jhana’s candid journey from failed startup employee to 22-year-old COO and coach—plus what she learned about leadership and operations along the way
• The surprisingly simple difference between visionary founders and world-class operators
• Why trying to “do it all” is a growth killer, and the power of delegation and trust in building successful teams
• Confronting the mirror: The radical role of self-awareness, emotional work, and personal growth in business success
• How Jhana leverages her unique position as a young woman in a male-dominated space to create a competitive advantage
• The truth about Gen Z and Millennial work habits—debunking the “entitled/lazy” myth with real stories from small, successful remote teams
• Leadership hacks: Why focusing on outcomes (not hours worked) and genuinely caring about team members’ goals creates high-performing, motivated workplaces

Want to go deeper? Connect with Jhana Li at Spyglass Ops or follow her on LinkedIn and Instagram @jhanali. For more generational insights and practical strategies, subscribe to Gen Mess with Tess, and visit tessbrigham.com for coaching, courses, and more!

Remember: Cleaning up the “gen mess” in your business starts with one real, honest conversation—and that starts with you.

00:00 From Failure to Entrepreneurial Success

06:21 Balancing Leadership: Vision vs. Details

08:59 Founders Struggle to Delegate

11:38 Generational Shift in Communication Styles

14:26 "Standing Out as a Competitive Advantage"

17:29 Finding Growth in Challenges

22:44 Shifting Confidence Sources

23:48 Navigating Quarter-Life Crisis

27:33 "Focus on Individual Needs"

34:08 Quarter-Life Crisis and Mental Health

37:26 "Seeking Growth-Oriented Collaborators"

39:39 People-Centric Leadership Focus

42:43 "Human Connection is Challenging"

46:05 Scaling Teams for Digital Founders

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