Category: Mindset

  • Boundaries: The Invisible Perimeter to Scale

    Boundaries: The Invisible Perimeter to Scale

    In one of my past ventures, my business lost millions, because I allowed a “Hero” to occupy the C-Suite. This is a hard truth to admit because I pride myself on my boundaries. But, I used his clear lack of boundaries as a buffer to avoid enforcing my own and to keep my peace – a peace that eluded me.

    My co-founder was the quintessential “Servant Leader”—genial, calm, tireless, and always the first to jump into the trenches. He believed he was building a high-trust, flat culture. I watched as he eroded his own sovereignty, allowing the normalized audacity of his team to treat him as a safety net rather than operationalizing our vision at scale.

    And I let it happen because it was convenient for me.

    This didn’t make me a passive bystander; it made me an accomplice. My clean hands were actually a form of negligence. I was so focused on protecting my own comfort that I kept quiet on the fact that my trusted partner – a man I genuinely liked – was setting the building on fire with his heroism.

    At some point, I knew my options. As majority shareholder, I could:

    Fire him.
    Demote him.
    Hire more under him.

    I wanted to avoid the conflict of the first two, so we kept hiring.

    In failing to make the decision I knew I should have made, I did a massive disservice to the company. I should have fired him and replaced him with someone who could rebuild the team. But in my role driving revenue, I was “crushing it”—having fun, making friends, being interviewed—and I didn’t want to pivot into such a crucial, painful conversation.

    The Costs of Avoiding Confrontation

    Because I chose personal comfort over conflict, the rot in the organization didn’t just stay static; it metastasized. My decision to hire more under him was the exact moment the business model broke. I threw capital at a structural problem, increasing the velocity of our dysfunction. The results were devastating.

    A Culture of Learned Helplessness

    By hiring expensive talent under a “Hero,” we added to his work. Because my co-founder couldn’t set a boundary, he couldn’t delegate. The new hires quickly realized that they didn’t actually have to deliver excellence—they just had to cry for help and have it escalated to him. We were paying top salaries for people to watch my co-founder burn himself out.

    This sent a silent but lethal message: “I don’t actually trust you to handle this.” The result wasn’t a supported or empowered team; it was a culture of learned helplessness.

    The Skill Gap: Engineers stopped learning how to solve complex problems because they knew the boss would swoop in and do it for them. They got stuck in their skillsets and delayed their own promotions and career advancements. That later brewed resentment that showed up with sudden departures, sabotaged work, or simply checked-out employees.

    The Ownership Void: Work was no longer seen through to the end; it was merely “started” and then “escalated” for the boss to finish. The team wasn’t owning their work; they were merely funneling the hard labor off to the equity holder.

    The Hostility Pivot: As the stakes grew, the “high-trust” culture soured. Because no one was truly responsible for their own results, “dropping the ball” became the norm. They had the normalized audacity to say “Well, he wasn’t around to help us, he is always too busy.”

    Writing this I just remembered how we had a long list of items under a ridiculous status “Waiting for Executive”.

    Revenue Subsidized Risk

    This is where my culpability cuts the deepest. Because I was crushing it on revenue, I masked the operational bleeding and increasing risk.

    Every big deal I closed bought us more time to ignore the broken machine. My success created a false sense of security. I looked at the P&L and saw growth; I downplayed the spiraling risk of catastrophe of having reduced competency down to one person.

    My poor boundaries around conflict avoidance blinded me. I told myself this chaos “was just part of being a successful startup.” Even though by any metric, we should have been operating like a mature organization. Revenue growth served as justification for my silence.

    The Cost of Lost Clients

    Eventually, the bill came due. Client deliveries began to miss their marks—massive, high-six-figure misses. Then catastrophe struck. Major outage – 100% caused by the environment we had allowed to take shape.

    Millions lost overnight.

    The genial atmosphere evaporated, replaced by defensive finger-pointing. Since the co-founder had touched every project, he took the blame for every failure. It was the antithesis of what I had envisioned. We lost years of sales efforts in a week, all because our COO was unable to focus on his role, and because I had allowed it to continue.

    All this was a painful lesson more than a decade ago, but one I’ll never forget:

    Leaders with poor boundaries are bottlenecks who prevent their people from growing up.

    The Invisible Perimeter: How Boundaries Define Leadership

    I experienced this in my company, but I see it everywhere. Lacking boundaries manifests in many ways across the C-Suite:

    The Vague Visionary: Has poor boundaries around their own curiosity. They change the company strategy often, creating “Strategic Whiplash” for the team.

    The Filterless Communicator: Has poor emotional boundaries. The leader “over-shares” their anxieties or half-baked ideas with the entire staff, causing unnecessary panic because they haven’t learned to use their board or a coach as a perimeter.

    The Approval Seeker: Has poor boundaries around time. Because they haven’t set a boundary around their deep-work time, they become a high-paid administrator reacting to every department’s priorities.

    And so on, and so forth with countless examples.

    The Impact of Poor Boundaries

    A boundary is the psychological and operational perimeter that protects a founder’s most valuable asset: Clarity of Judgment.

    You are not measured by tasks completed, but by the quality of your decisions regarding Vision, Capital, and People.

    Impact on Vision: The Competence Trap

    Vision requires a CEO to look at the horizon. When you lack strong boundaries, you succumb to the gravitational pull of “doing what you’re good at.” Rewriting copy or debugging code feels safe—it provides a dopamine hit of “value.”

    But when you do this, you are a symphony conductor who has sat down in the string section. You might hit the right notes, but the orchestra has lost its cohesion. You have traded the podium for a chair, and the music suffers.

    Impact on Capital: The Dilution of Velocity

    Without clear boundaries, your capital becomes a humidifier—misting the air in ten directions instead of a laser cutting through your target market. A leader who says “yes” to marginal ideas wastes the velocity of capital. The result may be a product that is feature-rich but profit-poor, sold in markets you have no business being in.

    Impact on People: The Culture of The Shadow

    When you have poor boundaries around role—answering Slacks at 2 AM or jumping into channels you don’t belong in—you cast a destructive shadow. You create a “theatre of productivity” where people stay online just to be seen. High performers leave for autonomy; those who tolerate micromanagement stay for the paycheck.

    The Identity Trap: You Can’t Just “Read” This Into Practice

    If you are nodding your head right now, be careful. That’s probably just a dopamine hit, not transformation.

    Boundaries are tied to identity beliefs held for decades. “My value is my utility,” or “I am a good person because I help.” The list goes on.

    Deep work is required.

    Without the deep work, the brain will revert to its old identity the moment pressure spikes. You will justify stepping back into the trenches as “necessary” when in reality, it is a retreat to a comfortable, destructive identity.

    True change doesn’t happen by learning a new “hack”; it happens in transformative work where you rewrite your identity and safely get to strengthen and practice it.

    The Boundary Audit: A Process of Inquiry

    If you want to move from “nodding” to “being,” you must audit your life through the lens of open, curious, self-inquiry. Often! I did the work for many years myself, and still do, and didn’t know it would lead me to eventually helping other founders and executives.

    A great coach ask questions to your blind spot and holds space for you to show up and do the work. Coaching questions show up uniquely to every person, but some examples to uncover old beliefs might look like:

    “How am I complicit in creating the conditions I say I hate?”
    “What is the ‘payoff’ I get from jumping in?”
    “Does solving this fire make me feel more valuable than the long-term work of strategy?”
    “If I died tomorrow, which of these processes would stop immediately?“
    “Why have I built a system where I am so needed all the time?”
    “Am I actually helping my team, or am I stealing their opportunity to become competent so I can stay relevant?”

    Examples of Boundaried Responses

    Once your identify changes, your language changes. Leaders who go through the deep work learn to attune to their intuition and consequently develop language that helps them show up healthy under pressure. Again, from my own experience, I can share some examples:

    ScenarioThe Old Way (Hero)The Boundaried Way (CEO)
    Team asks for a decision.“Let me look at it and I’ll get back to you.”“You are the DRI. What would you do if I weren’t here? I’ll back your play.”
    A “quick” Slack on Sunday.Responding immediately with a solution.(Silence until Monday) then on Monday “Put this in our 1:1 doc for Tuesday.”
    A client escalation.“I’ll jump on a call and fix it.”“I trust you to handle this. If they need my input, you can package it into a 2 minute read and I’ll chime in the doc.”
    A new project idea.“That sounds great, let’s try it.”“That’s interesting. Which of our top 3 priorities should we kill to make room for this?”

    The Shift

    There is no hack. True change doesn’t happen in the reading. It happens in the deep work of transformation. You become who you need to be, or you revert to who you were.

    Boundaries make the difference between a founder who “hustles” and a CEO who “leads by vision.” By defining where you end and the company begins, you don’t just save your sanity—you give your people the space they need to grow. And if you build a culture where your people grow, by extension and consequence and good fortitude, your company will grow and thrive.

  • 17 Years of Therapy as an Entrepreneur

    17 Years of Therapy as an Entrepreneur

    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 bearded 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:

    TherapyCoaching
    Primary FocusThe Soul and the Past.The Company and the Future.
    Key Question“Why am I this way?”“How do I lead from here?”
    ScopeHealing and Integration.Strategy and Methodology.
    OutcomeInternal 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.

All Posts