Hi, I'm Dileepan Siva
I coach leaders to evolve faster than companies scale.
I'd scaled companies before. Built teams, raised capital, navigated exits. But sitting in a board meeting after my co-founder left, I realized something I now hear from every client: The company was evolving faster than I was. The tactical stuff — I had that down. But who I needed to become to lead through this next phase? That was the real challenge.
Raised across three continents — I'd grappled with identity my whole life. Who are you when every few years you have to become someone new? This nomadic childhood taught me what most leaders only discover during transitions: identity isn't fixed. It evolves — or it doesn't, and you get left behind.
Through three startups and two Fortune 500 executive roles, I lived every inflection point. The chaos of creating from nothing. Scaling from 10 to 100+. Board dynamics. Strategic influence versus hands-on execution. Leading through others instead of doing it yourself.
But despite all the tactical and theoretical knowledge — Berkeley, Harvard Business School, two decades of operating experience — I kept hitting walls that weren't about what I knew or was doing. They were about who I was being. The answer wasn't in more tactics. It was in understanding myself.
Which is something I'd been exploring my whole life. From my first silent meditation sit in grade school to every personal growth pitstop from Landmark to Hoffman, I'd been on a journey of self-discovery in parallel. This foundation led me to formal coach training at the Co-Active Training Institute and Conscious Leadership Group, and deeper work in spiritual psychology at the University of Santa Monica.
All these experiences pointed to the same truth: Business and personal challenges are opportunities to transform identity in disguise.
Today, after 2000+ hours coaching leaders through transitions, I understand what that boardroom moment was teaching me. The gap between your role's demands and your current identity isn't a problem to solve — it's the work itself.
People ask why I chose coaching over another startup. I haven't—coaching IS my venture. What began as leaders seeking guidance revealed where I'm world-class. The companies I built were the training ground. This is the real work, and the foundation for everything I'm creating next.
What I believe and why this matters
Beyond the work
To hold space for transformation, I maintain my own practices and rituals. Daily meditation and journaling. Regular work with my own coaches and healers across body, mind, heart, and spirit. Because you can't guide others where you haven't been willing to go — or be led.
I find clarity through movement — hiking mountain trails, and soon leading spiritual treks around the world. While there's power in face-to-face coaching, there's something profound about walking side by side in nature. The conversation changes. Defenses drop. And a different truth emerges when you're looking at the horizon instead of each other.
The real work isn't done in caves or retreats. It happens in the crucible of daily life—in business, partnership, and family. These aren't distractions from spiritual work. They're the vehicles for it.
Every relationship becomes a mirror. Every challenge, a teacher.