Path 1: CEO Advisory & Organizational Systems Work

This path is designed for CEOs and senior leaders of growth-stage startups, enterprise companies, and investment firms.

The First 6 Months

We work together closely to establish trust, communication cadence, and a clear understanding of what you're seeking to build. This time is dedicated to learning about your thinking, natural strengths, areas of challenge, approach to leadership, vision for your company—and perhaps most importantly, who you are as a whole person, both at work and in life.

Getting to know the whole person matters deeply to me. I invest significant time understanding both dimensions of your life because they're inseparable. If you are not in NYC, I will travel to where you are to spend meaningful time both in and out of office. To give some examples: my very first meeting with an enterprise CEO last year began at dawn in a cold parking lot pulling on wetsuits—we surfed his local break before heading to breakfast then the corporate office for our first official day of work. Another CEO and I spent our first day walking his dog through Prospect Park (2 loops), talking about his relationship with his father and how it shaped his leadership. These aren't detours from "the real work"—this is the work.

At the heart, we're forming an important long-term relationship that transcends the immediate business challenges. Strong partnerships take time to develop, and they require us to understand and relate to the many human dimensions of who you are. The success of our engagement depends on the quality of our relationship and the level of trust between us. We'll need to speak more frankly to one another than in any other professional relationship. When we can be ourselves completely, we have a real opportunity to build something profound.

Over these six months, we'll explore your:

• 3-year vision for the company or firm, and clarify what follows from that north star: your 1-year goals, quarterly priorities, and current focus

• Leadership style and ability to build culture

• Team's capabilities and level of talent

• Role clarity and boundaries of what only you can do

• Colleagues' strengths, gaps, and how the leadership team functions together

• Relationships with the board and investors

After Six Months

Some CEOs prefer to continue only with ongoing 1:1 work. However, in many cases, the work naturally evolves to include others because the issues we've diagnosed require systemic intervention—not just CEO-level support. When blockages exist throughout the organization, addressing them at the CEO level alone is insufficient. In these situations, my role often expands to work directly within the system, beginning with the executive team.

I start by integrating with your leadership team—attending executive meetings, participating in strategic planning sessions, and providing real-time guidance as the team navigates critical decisions. The goal is to help the executive team function as a cohesive unit while diagnosing where clarity, alignment, and execution are breaking down between levels.

From there, the work cascades through the organization.

For earlier-stage startups, I'm able to serve as a Fractional Chief People Officer, focusing on strategic organizational development rather than HR operations.

Path 2: Individual Leadership Transformation

This path is for accomplished entrepreneurs, creatives, and thought leaders—typically from tech, media, law, conservation, entertainment, and the arts—ready for fundamental change, not incremental improvement. You've experienced success in current or previous roles, but you sense something missing. You want to create the next stage of your life aligned with your core truth, whether that's a creative project, career change, or major lifestyle shift. At heart, there's an unlock you're seeking.

The Work

We discover what you actually want—a slow, patient process that can't be rushed. As Jungian analyst James Hollis says, the adult's primary job is "knowing what you want and then mobilizing the inner resources to achieve it." This may seem simplistic, but it's extraordinarily difficult to know what one wants.

We slow down to introspect. We patiently—and strategically—allow what's within to come forward—it's akin to waiting for a deer to emerge at the forest edge.

Simultaneously, we address persistent personal and relationship issues that impede progress: emotional baggage, limiting beliefs, entrenched patterns. We'll update your "operating system" with a new program that allows more flow, ease, and certainty. We look at your tactical systems to ensure you're operating with momentum, clarifying commitments of time, energy, health, family, and finances.

This is intensive, transformational work grounded in a high-quality relationship built on trust, vulnerability, accountability, and healthy risk. Past clients report greater results in one year than from many years of therapy or other coaching programs.

The Commitment

This is a 12+ month engagement requiring full commitment. You must be ready for discomfort—the space between your old comfort zone and any new answer is where transformation happens.

Investment

Fees begin at $6.5K per month