Podcast Summary: Second in Command with Cameron Herold

Episode 504: Caitlin Fagan – How Being #2 Taught Me Authentic Leadership Like No One Else Could

Date: August 26, 2025

Overview

This episode features Caitlin Fagan, COO of Intermatrix Systems, as she dives deep into how her experiences as “#2” have honed her approach to authentic leadership. Caitlin and host Cameron Herold discuss vulnerability in leadership, embracing human experiences within company culture, the transformative power of systems like EOS (Entrepreneurial Operating System), and the intentionality behind growing people-centered businesses. Caitlin also offers candid insights into working closely—and romantically—with a CEO, as well as building scalable personal development systems for high achievers.

Key Discussion Points and Insights

1. Journey Through EO, EOS, and Stepping into COO

• EO’s Impact: Caitlin describes the Entrepreneurs’ Organization (EO) as instrumental for growth, both as a business owner and operator. Its forum structure taught her vulnerability and expanded her network.
  “EO was one of the first places... where I saw these people that I really respected... also struggle or have doubts.” (06:33, Caitlin Fagan)

• Bringing EOS to Intermatrix: Years of leveraging EOS frameworks gave Caitlin a toolkit that she brought to Intermatrix to help scale.
  “I was able to just bring the tools from as simple as the Level 10 to Rocks to the Scorecard... These truly help to run a business.” (14:36, Caitlin Fagan)

2. Vulnerability, Authenticity, and Leadership

• Human Leadership: Caitlin emphasizes the importance of acknowledging leaders’ and employees’ emotions, rather than suppressing them—especially in high-performance, tech-oriented environments.
  “You don’t have to be perfect, or know all the answers... You can actually be a human and run a company.” (06:33, Caitlin Fagan)

• Supporting the Whole Person: She highlights the necessity of embracing employees’ full selves—recognizing personal challenges as part of the work dynamic.
  “It’s a really big mess for people to expect employees to just come in and leave whatever’s happening for them at the door… ultimately, they can do their best work.” (09:11, Caitlin Fagan)

3. Balancing Compassion & Accountability

• Performance Culture with Empathy: Caitlin shares her approach to balancing empathy with accountability.
  “How can I support you to get that done, regardless of what’s going on for you?” (12:36, Caitlin Fagan)

• Setting Boundaries: Cameron discusses the need to avoid “Groundhog Day” scenarios—support is vital, but action and personal responsibility are equally essential.
  “If you’re not going to take responsibility for stuff and grow… we can’t just keep supporting you if you’re not going to do anything about it.” (13:17, Cameron Herold)

4. About Intermatrix Systems (IMS): A Personal Operating System

• Personal Development for High Achievers: IMS is likened to EOS for individuals—a proven, repeatable system to train and align emotion, thought, and nervous system, helping people achieve fulfillment and peak performance.
  “It’s like a business operating system for the person.” (17:46, Caitlin Fagan)

• Future-Focused, Repeatable Tools: Their approach is less about analyzing the past and more about actionable, forward-thinking change and self-reliance.
  “We’re very future-focused. How do you want to feel? What’s the outcome you want? Let’s get to work on creating that.” (21:55, Caitlin Fagan)

• Scalable Training & Community: IMS employs a “train the trainer” model—apprentices undergo rigorous training to scale the impact, supplemented by global communities fostering support and camaraderie.
  “It’s something like a 2000-hour program… they learn the curriculum, they understand… because we’re supporting people in intimate parts of their life.” (28:40, Caitlin Fagan)

5. Culture, “Culty-ness,” and the Importance of Community

• Walking the Line: Caitlin acknowledges that passionate group cultures can be misread as cultish, but emphasizes self-reliance and autonomy within IMS.
  “We never tell you what to think, what to want… our systems are about how to think, how to position yourself.” (26:52, Caitlin Fagan)

• Community as Support & Stickiness: Community arose organically—people wanted to train and grow alongside like-minded peers, extending engagement in personal mastery journeys.
  “Let’s do life with people that are on a similar trajectory and have a similar zeal for life…” (32:26, Caitlin Fagan)

6. Tech, AI, and the Future of Personal Development

• Embedding AI: IMS is preparing to harness AI for on-the-go personal development—enabling immediate, personalized support.
  “I want to have a pocket AI trainer at some point… we’re definitely looking to build out an AI trainer…” (34:10, Caitlin Fagan)

• Changing Role of Coaching: Conversation with Cameron touches on how AI-driven avatars may democratize access to world-class coaching, creating both new challenges and opportunities for authentic connection.
  “In a way, I think coaching is almost gone… There’s no way that someone’s going to pay me what they pay me now to get my advice when they can pay an avatar version…” (35:00, Cameron Herold)

7. Authenticity in Work & Relationships

• Personal and Professional Boundaries: Caitlin reflects honestly on co-running a company with her fiancé (the CEO), detailing the challenges and unique strengths of their partnership.
  “It is not for the faint of heart… I wouldn’t lead with that for sure… we’ve learned to stay in our lanes in business and personal.” (36:46, Caitlin Fagan)

• ‘Seasons’ Approach: Rather than strict boundaries, they operate in intentional seasons—high-intensity work periods balanced by more personal time.
  “We’re pretty good at just seasons throughout the year… dinners are strategy during program runs… and then on the other side, we focus more on the personal.” (39:43, Caitlin Fagan)

• Building Deep Team Relationships: Caitlin and Cameron agree that friendship and deep knowing between leaders and their teams encourage trust, resilience, and higher performance.
  “You really want to get to know the person so you know what they’re made of, what you can count on them for…” (41:38, Caitlin Fagan)

8. Notable Quotes & Memorable Moments

• On Authentic Leadership:
  “Figure out who you are and then be that person all out.” (44:09, Caitlin Fagan)
• On Vulnerability and Success:
  “You can actually be a real person and lead a company. You don’t have to be perfect or know all the answers.” (06:33, Caitlin Fagan)
• On Training the Whole Person:
  “You only have one life, you only have one nervous system…” (09:11, Caitlin Fagan)
• On Friendship at Work:
  “I’ve always developed close relationships with the people I work with… that gives you an inside track to how far we can go.” (41:38, Caitlin Fagan)
• Advice to Young Leaders:
  “Don’t work to be what you think you’re meant to be… Figure out who you are and be that person.” (44:09, Caitlin Fagan)
• Cameron’s Mother’s Wisdom:
  “Be yourself. Everyone else is already taken.” (45:08, Cameron Herold)

Timestamps for Important Segments

| Timestamp | Segment | Speaker(s) | |-----------|------------------------------------------------|-------------------------| | 03:51 | Caitlin’s EO/EOS journey | Cameron, Caitlin | | 06:33 | Embracing vulnerability in leadership | Cameron, Caitlin | | 09:11 | Supporting employees holistically | Caitlin | | 14:36 | Implementing EOS at Intermatrix Systems | Caitlin | | 17:46 | IMS as a personal operating system | Cameron, Caitlin | | 21:55 | IMS system vs executive coaching | Caitlin | | 28:40 | The “train the trainer” program & networks | Caitlin | | 34:10 | AI and the future of personal development | Caitlin | | 36:46 | Working with/being engaged to the CEO | Caitlin | | 41:38 | Deep team relationships and friendship | Caitlin, Cameron | | 44:09 | Advice to her 21-year-old self | Caitlin |

Conclusion

This episode offers an expansive look into the mindset, tactics, and real-life complexities faced by effective COOs. Caitlin Fagan’s advocacy for authenticity, clear systems, vulnerability, and whole-human leadership provides actionable inspiration for any second in command. The conversation moves seamlessly from strategic frameworks to the interpersonal—always rooted in real experience, humor, and a desire to help others grow both in business and in life.