255: How Great Leaders Grow People Faster — The 2025 Leadership Playbook | Cameron Herold

Helping people grow, building teams that win, and leading through rapid change—business success doesn’t have to be complicated. In this energizing episode, Damon sits down with legendary operator and leadership coach Cameron Herold to reveal the core skills every leader needs—but most never learn. From skyrocketing 1-800-GOT-JUNK’s growth to founding the COO Alliance, Cameron Herold shares field-tested lessons on interviewing, delegation, building culture, and coaching your team. You’ll learn actionable frameworks for hiring, developing talent, running better meetings, and leveraging AI—plus the mindset shift that turns managers into true leaders. 

Packed with real stories from hiring 8,000 student painters in six weeks to transforming toxic teams, this episode is your practical playbook for scaling yourself, your team, and your business. 

In this episode, you’ll learn: 

• Why your #1 job as a leader is to grow your people (and how to start today) 
• Cameron’s favorite interview and reference “torque” techniques—and how to spot true performers 
• The power of situational leadership: how to adapt your style based on each team member’s needs and projects 
• Why delegation unlocks scale—and how to finally get out of the weeds (hint: delegate everything but your genius) 
• How to build a culture that drives results and stays free of toxic talent 
• The mindset and tools needed to future-proof your team in the era of AI 

Timestamps: 

00:00 – Why business is simpler than you think 

00:47 – How Cameron grew 1-800-GOT-JUNK from 14 to 3,100+ employees 

02:14 – “A leader’s job is to get results through others”—Cameron’s College Pro Painters story 

04:01 – Why people struggle with interviewing, meetings, and core management skills 

05:11 – The danger of “30 years’ experience” vs. real growth 

06:25 – Group interviews and the “threat of reference check” (TORC) method 

08:38 – How to spot a victim mentality (and why introspection matters in hiring) 

10:24 – The difference between theory and proven experience 

13:30 – Why toxic high performers destroy organizations 

16:27 – What most leaders get wrong about delegation 

19:28 – How to delegate things outside your own expertise (and who to bring in) 

21:48 – Helping new managers win by embracing vulnerability, coaching, and connection 

24:44 – The essentials of situational leadership (and why it’s every leader’s secret weapon) 

28:50 – How to promote and onboard new leaders for success 

30:17 – Why curiosity and “learning time off” are now nonnegotiable 

35:03 – Leading for the whole company, not just your function 

38:10 – Core values in action: Calling out leaders when they break them 

41:18 – Disruption and simplicity in the age of AI 

45:03 – Skills, confidence, connections: What it really takes to grow as a leader 

About Cameron Herold 

Cameron Herold is a globally recognized business growth expert, author, and the founder of the COO Alliance—the top community for second-in-command leaders. Nicknamed the “CEO Whisperer,” Cameron was instrumental in scaling 1-800-GOT-JUNK from just 14 staff to over 3,100 and $100M+ in revenue. He’s a six-time author, award-winning keynote speaker, and creator of the Invest in Your Leaders program. Cameron’s legacy includes coaching high-growth organizations on core leadership skills, situational management, and building companies where people love to work. 

Resources & Mentions: 

• Cameron’s Website  
• Cameron’s LinkedIn 
• Who Not How by Dan Sullivan & Ben Hardy 
• Ken Blanchard & Paul Hersey – Situational Leadership / The One Minute Manager 
• There’s an AI for That – AI Tool Directory 
• The Five Dysfunctions of a Team by Patrick Lencioni 
• COO Alliance 
• Invest in Your Leaders Program 
• Cameron’s upcoming book: “Grandmother’s Timeless Tales on Business Success” 
• 1-800-GOT-JUNK 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

Follow us on LinkedIn and Instagram for more updates.