About me

How I got here

My friends call me a recovering overachiever.

For more than a decade, I lived the kind of life ambitious people are told to want. Ivy League degree, consulting job, fast promotions. I helped build one company through an IPO to a $12B valuation (and an Emmy - long story), then helped scale a YC-backed education startup to a 9-figure acquisition. I was making more money than I'd ever imagined.

Behind the scenes, I was falling apart.

I was burned out, anxious, sleep-deprived, and increasingly convinced that if I kept going, I was going to look back on a life I didn't actually want.

The harder I pushed, the more I felt like I was pretending to be someone I wasn't.

Outside, I looked successful. Inside, I was deeply dissatisfied and starting to suspect that the ladder I'd been climbing my whole career was leaning against the wrong wall.

So, with guidance and support, I began questioning and unlearning the scaffolding of my identity: inherited programming from society, family, and industry.

I began to see more clearly. Every moment of insight brought a little more connection to a more honest version of me.

In time, the work that changed me became my work. In the years since, I've partnered with leaders at some of the most innovative companies in the world, ranging from fast-growing tech startups and top venture firms to leading non-profits and the Fortune 100.

But that's not the real story.

The real story is that I feel more ME than ever.

I'm more clear on what I stand for, and what I won't. More accepting of myself. More loving in my relationships. More effective at my craft. Less reactive when heated. Less afraid of not being enough. Better at taking bold swings. Better at not taking myself too seriously.

I'm in my 40s now. The biggest thing I've learned is that the true journey is the inner journey - and that it turns out to be good for business, too. When leaders operate from a place of inner clarity, they become more effective, creative, and alive. And they give the people around them permission to do the same.

If that's the kind of conversation you've been looking for, I'd love to explore it with you.

Warmly,
Leland

見性

My craft

I named my business after Kenshō, from the Japanese 見性: ken, to see, and shō, nature. "Seeing one's true nature."

In Zen it means an initial awakening. Not some final state, but a moment of recognition along the path. Where the real work begins, again and again.

I love two aspects: remembering what's actually there, underneath the stories we tell ourselves and those we were given. And the boundless nature of this work. Insight can come quickly; acting from it is the ongoing practice.

My specialty is creating relationships and experiences that wake leaders up to how innately capable, powerful, and loving they already are. That's right - it's been there all along.

Rather than leading with theory and frameworks, we co-create the conditions for self-generated insight, and then we practice living from it.

Nature is a catalyst for this process - climbing mountains, hiking through forests, polar bear plunging in oceans, even jumping out of airplanes - as a way of tuning in to what's here in this moment.

Some of my lenses

Principles I strive to live by

Why: they keep things simple, keep me humble, and show me where to clean things up when I drift.

1. I seek and speak the truth.
2. I nurture my mind, body, heart, and spirit. This is the only way to serve others fully.
3. I am committed to my family - being loving, being present.
4. I prioritize long-term games with long-term people.
5. I can learn something from everyone.
6. I am not for everyone.
7. It's not about me.

Ubuntu: I am because we are

I am fortunate that some people believed in me before I believed in myself.

Beyond my family/friends, I'm especially grateful to these folks for seeing something in me:

Thank you. Your love lives on through me.

Terry Driskill, Alice Meyer, Kurt Meyer, Pierre Yoo, Josef Mittlemann, Arkady Belozovsky, Nick Rintalan, Eric Jurasinski, Mike Schaeffer, Meghan Laffey, Sumit Chawla, Romulo Melo, Paul Jeune, Alex Cashman, Dusty Hanks, Ben & Devin Roane, Alana Fulvio-Bigley, Donagene Jones, MX, Mikey Knight, Debbie Cohen, Susan Carlisle, Anne Grete Mazziotta, Dan Spinner, Steve Hardison, Ankush Jain, Townsend Wardlaw, Jonah Cohen

Influences

Some of the thinkers, teachers, and writers whose work has shaped my own.

Esther Perel, Brené Brown, Simon Sinek, Adam Grant, Patrick Lencioni, Tim Ferriss, Alex Hormozi, Sri Nisargadatta Maharaj, Rumi, Sam Harris, Henry Shukman, Adyashanti, Elena Bower