A Hard Goodbye, an Easy Goodbye and an Easeful Hello

On confronting death, leaving venture capital, and spreading meditation

A Hard Goodbye

When most people stare death in the face, they see fear. I know I do. It can be so incredibly difficult to sit with death and watch, in helpless agony, as a person you love withers away. Yet I had the exceptional privilege to live with a woman who saw beauty when confronting her death: my life-partner, Grace. After a nasty cancer diagnosis in 2018, Grace used what little time she had left to sing in dog voice every morning, point out each flower she saw, dance in hospital rooms, attentively listen to stories from random strangers on the street, color breath-taking mandalas, quietly walk through redwoods, and tell friends she loved them (usually while eating fruity ice pops).

A big part of what enabled Grace to face her diagnosis with, yes, grace, was meditation. Grace had first found meditation while enrolled in an eating disorder treatment program during college. Yet while meditation was lightly woven through her life, it didn’t become transformative until she got sick. When your body is failing you, it becomes more and more clear that you need to learn to accept it, not in the sense of giving up or saying everything’s fine, but in the sense of acknowledging the difficult reality. You have no other choice but to feel the body’s pain and appreciate the parts that work, which is most of them, even when you have terminal ovarian cancer.

Meditation mixed with cancer taught Grace to love and fully accept her body and eventually her full self. Of course, there was plenty of fear in there too, but her fearless self-compassion was simultaneously heartbreaking and awe-inspiring to be with (as many of the best things in life are).

Early in the morning of July 23rd 2020, Grace took her last tired breath with her hand in mine, in a house that she chose to die in, full of humans (and two dogs!) that deeply loved her. Later that day, we borrowed from a Buddhist tradition of covering the body in vibrant flowers to get close to the beauty in death, just as Grace did:

This is certainly not an easy goodbye, but I’m glad I got to do it with Grace.

An Easy Goodbye and an Easeful Hello

For nearly every human alive, 2020 was a challenging year. I certainly had my heaping helping of difficulties (see above), but I was also blessed to have some of my closest friends leave their solo quarantined lives behind and come live with Grace and me as she started home hospice. Boldest among them was one of my oldest friends, Ben Rubin, who rented a car and drove out from Boston:

I met Ben years ago while he was running one of the first connected hardware startups (Zeo). While I was off building a venture firm for hardware companies (Bolt), Ben started Ten Percent Happier with Dan Harris, who wrote the bestselling book of that name, and Derek Haswell. Ben had also roped Grace into helping Dan write the sequel to his book, this one on self-compassion. (Dan affectionately refers to Grace as his “book therapist,” which still makes my heart smile.) But most importantly, Ben is the kind of friend that shows up at your door after a three-day cross-country drive with a bernese mountain dog puppy when his friend’s wife is dying of cancer.

Over the six months Ben lived here, we spent a lot of time talking about Ten Percent Happier, and about meditation — the company’s flagship product is a meditation app with a devout user base, and recently, an incredibly popular podcast. The profound effect that meditation was having on Grace as she grew sicker, and talking about the business endlessly with Ben, drew me deeply towards meditation. What was previously an occasional habit for me turned into a daily meditation practice. Through cancer, hospice, death, and grief, meditation was one of the few things that helped me every single day. No matter what I was struggling with, this quiet little practice was there to remind me I was okay. That everything would be okay.

After Grace took her last breath, and after working through the initial phases of grief with the added challenges of a global pandemic, racial justice protests, and a turbulent election, I faced a choice: what to do next.

All my life, I’ve been singularly focused on building things: actual, physical things. From the earliest age, I learned to understand the world through physical objects and eventually fell in love with bringing them into the world. After college, I started a company that helped others build new products; eventually we helped bring some pretty rad things into the world (including the first Bluetooth accessory for the then-new iPhone). Then, after an accidentally successful royalty deal, I started a venture capital firm (Bolt) to help people that wanted to build physical product companies.

My relationship with venture capital was always complex. It is at once deeply empowering and endlessly thrilling, but with uncertainty and inauthenticity lurking in the shadows. I deeply loved my time helping build products and companies but I could never make venture capital a comfortable bedfellow. I felt like I never had the time or resources or experience to support enough. So, after the better part of a decade, I’ve decided to say goodbye to the world of venture capital and hello to the world of meditation 👋.

As of March 1st, I’m joining Ben, Derek, Dan and the whole Ten Percent crew on a mission to spread moments of okay-ness to minds everywhere. Meditation transformed Grace’s life (and death) and it has the capacity to profoundly change the world in ways I believe are more necessary than ever. As President and COO of Ten Percent Happier, I’ll be focused on building new products/services and accelerating the existing business. It’s bizarre and scary to be leaving hardware products behind, but I can think of no better way for me to have an impact on the world after this monumental transformation I’ve had.

And as a little extra bonus: I’ll be working for the company Grace choose to spend the last year of her life supporting and advancing a mission she cared passionately about. In more ways than one, Grace is still with me every day.

I probably won’t be writing about hardware much anymore, but I’ll certainly be building a few things in my spare time 🔨

Thanks to Jay Michelson for editing this post.