Steve Schlafman

Transitions create an opening to reconsider what truly matters and reshape how we live and lead. I guide founders, executives, and investors through these moments of change.

I spent nearly twenty years as an operator and investor. I started in finance and strategy at Microsoft, oversaw new ventures at The Kraft Group (owners of the New England Patriots), then spent a decade in venture capital at Lerer Hippeau, RRE, and Primary, seeding dozens of startups, including Zipline, Boom Aerospace, and Brightwheel. By 36, I had made partner and achieved what I’d spent years chasing. I had influence, access, and a clear path to wealth, but I was burned out and disconnected. I walked away from institutional investing without a plan.

Over the past twelve years, I’ve gotten sober, cultivated a daily meditation practice, and studied Hakomi, Internal Family Systems, and Conscious Leadership. I built a coaching practice, founded Downshift, a program for leaders moving through transition, and raised an angel fund for the builders I still love backing.

People come to me when something important is shifting. They may be stepping into a bigger role, reconsidering their place in a company they built, or finding that the ambition that carried them for years no longer gives them direction. Often, the immediate decision opens up larger questions about who they are, what matters to them, and how they want to live.

We slow down enough to understand what’s happening and bring that understanding into your choices and actions. I ask direct questions, help you examine old patterns, and offer perspective from my years in business. Depending on what you need, we might work through a consequential decision, explore an internal conflict, or design a small experiment to learn what fits. Between sessions, I send personal reflections and practices to help you carry the work into daily life.

At Camerado, I get to bring this work into a partnership with Ryan and Derek, whose experience and perspectives challenge and deepen my own.

I live in the Hudson Valley with my wife and our two daughters. I love long bike rides, walks in the woods with a friend, cooking for my family, and watching the Patriots win.

You can learn more about me at steveschlafman.com or read my writing at Field Notes.