It was 2007. I was living in Newport Beach, pocketing several hundred thousand dollars a year, and leading a company that had found its stride. I had a white SL convertible shipped to me from the east coast that I paid for on my Amex. To my friends and colleagues, I was living the entrepreneurial dream. But my reality was a different story. I was living with a level of suffocating anxiety that made it difficult to catch my breath. I suffered from multi-day migraines that felt like a violent protest from my own body. I was only 30. I was angry at the world for the endless list of problems it delivered to my desk, clearly unaware that my own methodologies for handling life were the primary source of my friction.
I walked into therapy that year not because I wanted to grow as a person, but because I believed everyone else was the problem and I needed to know how to better control the outcomes I sought. It wasn’t even seeking help about my anxiety, just anger-led to go see the beared therapist to fix the problems of my life. That first step began a seventeen-year commitment to my interior work—a journey that would eventually lead me from the practical tools of the present, to the deep archetypes of my past, and finally to the strategic design of my future.
The Early Years of Therapy
My initial years were spent in the world of Cognitive Behavioral Therapy (CBT). As a CEO, I treated therapy like any other optimization problem. My therapist got into my dense head that at the very least, I can’t think clearly when I’m angry and so I bought into some CBT resources. I wanted a quick fix for anger and stress to gain better focus and make sharper decisions. CBT provided a structured, actionable framework that felt familiar enough to a business mind.
The Benefits of CBT as a Founder:
Immediate Grounding: It provided “battlefield” tools to manage my anger in the middle of a high-stakes meeting.
Identifying Distortions: It helped me recognize when I was “catastrophizing” a missed quarterly goal or simply one lost prospect, allowing me to return to a more rational baseline.
Habit Restructuring: It offered a way to challenge the immediate, negative thought patterns that led to reactive decision-making.
However, as the company continued to scale and I acquired another company, I began to hit the boundaries of what this approach could offer. For a founder responsible for the culture and strategy of a large organization, the limitations became clear.
The Limitations of CBT from a Business Perspective:
Symptom-Focused, Not Future-Oriented: CBT is designed to get you back to a baseline so you don’t feel so anxious. But as a leader, I needed to move toward “times ten.” I needed a vision and a methodology for the future, not just a way to survive the afternoon.
Individual vs. Organizational: CBT gave me a breathing exercise for my stress, but it had nothing to say about how to handle a co-founder who, I felt, was undermining the company’s mission.
The “Why” vs. the “What”: It could help me change a thought, but it didn’t help me understand the deep-seated belief system that created that thought in the first place. It patched the leak but didn’t address the structural integrity of the dam.
The Descent: Jungian Analysis & the Shadow
My search for deeper answers eventually led me to a Jungian Analyst. If CBT was about managing the surface, Jungian therapy was an archaeological excavation. I spent more than a decade in this work, which is rooted in depth psychology and the process of “Individuation”, or becoming a whole, integrated human being.
Working with an analyst is a rigorous process. It involves looking into the “Shadow”—the parts of ourselves we have suppressed or denied because they didn’t fit our image of a “successful leader.” For much of my life I had relied on a rigid need for control and feared and rejected vulnerability, believing that combination was the engine of my success. In reality, they were the sources that fueled my exhaustion and my problems in the company.
As Carl Jung famously observed:
“Until you make the unconscious conscious, it will direct your life and you will call it fate.”
In the context of leadership, this is profound. The parts of a founder that remain unconscious will eventually run the company.
If you have an unconscious need for validation, you will build a culture of “yes-men.”
If you have an unconscious fear of conflict, you will allow toxic behaviors to persist. And so forth…
My years in Jungian analysis allowed me to stop calling my patterns “fate” and start leading from a place of conscious choice. This work took deep root in me; it changed the very nature of my presence in the office.
When Therapy Met Mentor
The transition toward coaching began during a lunch at Killer Shrimp in Marina Del Rey with my mentor Fred — a former C-level executive at IBM and Mattel. For the first time in our long history, I didn’t talk about revenue, scale, or product-market fit. I talked about the internal toll. I told him about the migraines, the anxiety, and the feeling that success was starting to feel like confinement.
Fred listened with the perspective of someone who had seen the same patterns in the boardrooms of global giants. He shared his own struggles with burnout during the high-pressure years at Mattel, back when toys were built to last with die-cast metal, he would tell me. That conversation opened a new branch in my life. It was the realization that while therapy was tending to my soul, I needed a different kind of partnership to redesign my entrepreneurial journey.
Questions Only a Coach Asks
While therapy often asks, “Where does this feeling come from?”, coaching might ask, “What is this feeling costing your vision?”
The inclusion of coaching wasn’t a replacement for therapy; it was an expansion. My coach asked me questions that a therapist, focused on my psychological well-being, never would have considered.
Here are a few examples of how that coaching lens changed my company:
1. The Question of Identity vs. Role
The Question: “You say you ‘have’ to make every final decision to ensure quality. If you were to die tomorrow, would the company fail because of a lack of talent, or because you’ve designed a system that requires your permission to exist?”
The Application: This hit my need for control directly. We looked at the “methodology of permission” I had built and how approvals all routed to me (with a nifty workflow that I thought was efficient but all it did was funnel more problems my way faster).
The Change: I dismantled my “NASA-style” dashboard of 50 metrics and narrowed it to 3. I empowered my team to make decisions without my input. We created a committee that could arrive at their own decisions and justification and act on it. The result? Decisions were made faster, employee morale improved because they felt trusted, and I finally stopped got room to breathe and spend time doing what was truly my role – getting more clarity on our vision and our long term direction.
2. The Question of Value Alignment
The Question: “You are optimizing for ‘Scale,’ but your stress suggests you value ‘Peace.’ What would happen if you optimized for ‘Peaceful Scale’ instead of ‘Growth at all Costs’?”
The Application: This forced me to look at our sales strategy. We were taking on “toxic” clients who paid well but drained our team’s spirit.
The Change: We fired our most difficult clients and we fired our bottom of the barrel clients and repeated it every single year. It felt like professional suicide at the time, but it cleared the air and made space for more lasting and sustainable growth. We replaced them with partners who aligned with our values. Our customer service improved, our referrals increased and customer loyalty went through the roof. Later when I came to sell the company, we saw that our client retention average was an astounding 12 years.
3. The Question of the “Founder’s Shadow” in Culture
The Question: “Your team is hesitant to give you bad news despite you insisting its ok. What is it about your reaction to ‘failure’ that has made silence feel safer than honesty for them?”
The Application: Through my Jungian work, I knew I hated failure. My coach helped me see how that internal hatred was manifesting as a “culture of fear.”
The Change: I started a regular lessons learned forum where I shared my own mistakes first. By making vulnerability a leadership methodology, I unlocked the creativity of the team. I didn’t expect it but issues that had been lingering for months were solved because people were finally brave enough to speak the truth.
The Synthesis of Therapy & Coaching
I stayed in deep therapeutic work years after my company was acquired, for what would be over 17 years. I’m a big advocate for everyone doing deep work. The only journey worth taking, in my humble opinion, is the one within.
Therapy is the work of the roots—it ensures the tree is healthy and grounded. Coaching is the work of the fruit. It is about the harvest—the strategy, the methodology, and the design of the future.
For the modern founder and CEO, the two are not mutually exclusive; they are interdependent. Here is it how I have experienced it:
| Therapy | Coaching | |
|---|---|---|
| Primary Focus | The Soul and the Past. | The Company and the Future. |
| Key Question | “Why am I this way?” | “How do I lead from here?” |
| Scope | Healing and Integration. | Strategy and Methodology. |
| Outcome | Internal Peace. | Sustainable Success. |
If you are building something significant and feel the pressure stretching you thin, remember: the business can only grow as far as you do. Seeking support is not a sign of weakness; it an act of leadership. If you ever feel you need someone in your corner that’s been through it, I’d welcome getting to know you.