Setting intentions

Today feels like a momentous culmination of a journey that started when I simply followed a thread of something that inspired me.

Back in 2004, I attended a talk at UC Berkeley by Paul Graham, who was promoting his innovative new investment firm with a funny name, Y Combinator. His idea was to give hackers like me some hands-on guidance and a small sum ($6K at the time) to build a startup. Though I’d already started several companies on my own, I recall being excited about starting a “real” startup with investors backing it. I just knew I needed to be a part of this movement.

Two rounds of applications later, I vividly remember Paul calling to tell me they had accepted my application into YC. I was over the moon; I had been welcomed into this obscure “startup founder” club/thing! I didn’t know where that journey would take me, but I was just excited to be along for the ride.

Over time, while building my own startups, I started setting my sights on becoming an angel investor. There was something so compelling about multiplying my creative potential by giving money to startups I believed in. And by “giving”, I actually mean that most of the time it felt like a donation! I had so much belief in this space though, I just loved the idea of living vicariously through other startups that I otherwise couldn’t contribute to.

My experience is that when you set an intention like “I want to become an angel investor”, or “I want to become an artist”, there is rarely a moment along the journey where you feel like you’re actually that thing. I was making relatively small investments in obscure companies that no one had ever heard of, so I never felt like a “real” angel investor.

And then, one day you wake up and you are that thing that you intended to be. Today is that day for me, because one of my early investments, Coinbase, has gone public (my first IPO)! It’s one of the first investments I ever made, and I distinctly recall thinking that it was one of my riskier investments given all the uncertainty around cryptocurrency exchanges at the time. And while I have long since sold my early crypto investments (doh!), I’m so glad I took a bet on this team.

I often feel conflicted about sharing personal achievements like this, but I wanted to share my story today in hopes it will inspire you to follow your own dreams, whatever they may be.

My own dreams are shifting yet again and welcoming in new intentions that don’t yet feel “real”. But I feel braver knowing that the path starts with setting intentions and following what inspires you.



I’m not sure if I’ve ever really felt comfortable in my adult body. I’ve consistently muted my physical expression out of fear of judgment. The few times I’ve been in situations where I couldn’t avoid dancing, I’ve felt tremendous awkwardness and shame.

Lately through meditation and by consulting with my guides, I’ve felt called to start exploring moving my body as a way of celebrating my aliveness. Last week I had an incredibly powerful dream of dancing with a partner that felt so liberating that I woke with tremendous energy and excitement! It was a fun change to be awoken with aliveness rather than fear/anxiety!

I think one of the biggest barriers to my exploring physical movement has been thinking that I didn’t “know how”. Part of me would prefer to remain closed than have to open through the unknowingness. In my dream, I’m fairly sure I was doing the tango, but I certainly have never tangoed before, so I didn’t know where to begin!

When I talked to my sister about it, she reminded me of an experience I shared with her from my experience at Rythmia. As part of the program, the week ends with the “Dance of Liberation”. I kid you not that when I first saw that on the program, I planned to skip the class! But I’m so glad I went because the experience was as profound as any of the other ceremonies of the week.

Everyone is blindfolded, and then you are prompted to just let the music move your body. No steps to learn, just flowing with the music. Beautiful healing music that we’d been listening to throughout the week was pumped throughout the huge space, and we were allowed to just move how we wanted. At first, I felt awkward and constricted (based on the nervous laughter around me I don’t think I was the only one!), but as I relaxed and felt the energy of the music, I was able to let go and just really move for the first time in my life. It started to feel very tribal as everyone released their fear and started really moving.

It felt so incredibly powerful and soul fulfilling to me to dance in this free spirited way. About midway through the ceremony, I was really getting into the beat and jumping to the beat. To my surprise, the floor itself gave way as I landed – I had broken a hole in the thick plywood floor! It felt like something out of karate kid!

That night as I was returning from dinner, I passed by the maloca and saw there was a team of a half dozen guys repairing the floor I unintentionally damaged. While I felt bad about unintentionally causing so much trouble, as someone who has lived my life not taking up space, it felt powerful to see the impact of my movement.

When Jamie reminded me of this experience that filled me up with so much aliveness and power, suggesting that I should seek out a similar format in my exploration around dance, it clicked. So I joined an online subscription at Open Floor Dance and signed up for a class.

Today was my first experience post-Rythmia with free movement dance. I felt very nervous about it, but I’m so proud of myself for showing up with my bravery and making it happen.

The class was over zoom, led by an instructor playing great music, and it was such a wonderful experience to be in my own backyard in the sun enjoying my own aliveness in the present moment.

I look forward to expanding more in this form of creative expression. If my story inspires you to challenge yourself in this way, check them out at If you have experience with this type of practice, I’d love to be inspired by your journey!

I look forward to dancing with you!



Two years ago I was sitting in my truck, sobbing with intense feelings of betrayal. I felt so confused and lonely. Compounding my isolation, I didn’t know how to express my feelings safely with my person. I felt unloved and unlovable. These feelings led me to say and do things that I now regret but were a portal of insight that ended a relationship that wasn’t healthy for either of us.

A year later, with my marriage all but over, I went to Rythmia in Costa Rica with hopes of connecting with people going through similar portals. All of my fellow attendees were becoming fast friends with their roommates, while the bed opposite mine remained empty. As it turns out, my roommate-to-be had canceled his trip last minute, and I had the distinction of being the only solo occupant of a double room on the whole property. This surprise solitude was a portal that cracked me open and allowed in greater self-love and social bravery.

Though I have found love since, today I am faced yet again with a portal of loneliness, which feels so deep and challenging. I miss my most recent partner so much, and so desperately want to fill this hole in my heart instead of facing my fear. I also have been setting firmer boundaries with my other relationships, which is triggering because I fear losing them as well. Yet I recognize this moment as another portal to embrace, full of wisdom ready to come ashore.

Upon reflection, I’ve never really allowed myself to experience loneliness. As an adult, I’ve moved quickly from one partner to the next without taking a significant break in between. The whole time I was running from my fear of being alone.

This fear has caused me to commit to and stay in romantic and business relationships that were not healthy for me. It caused me to unconsciously sacrifice my own needs, be dishonest, and refrain from authentic self-expression, all for fear of rejection and abandonment. On some level, I have gone through life subservient to the world out of my fear of being alone.

I experience this feeling of loneliness as a grasping towards the external. In my attempts to escape my fear, I find myself reaching for things that will either fill the hole in my heart or distract me, like working too hard, taking on endless projects, or getting into relationships too quickly.

As I’ve slowly let go of the attachments in my life, I realize that I’ve presciently created myself a perfect storm of loneliness in the present moment.

As I’ve meditated on loneliness, and experienced the ensuing waves of sadness, I have uncovered parts of myself that I feel judgemental of. Yesterday I sat with a barely intelligible piece that fears my success depends on my connection with others. A part of me that puts everyone in my life on a pedestal. I want nothing more than to cast it away as weak, but I realize that this part of me simply needs my love and understanding. So I have been focusing on this, journaling and listening.

One insight that has come from this place is that connecting with my needs and listening to the wisdom of my heart will dissolve this fear of loneliness. Because in the times that I listen to my guides and I connect with my heart, I don’t feel alone.

As is true about all fear, as I’ve spent time sitting with it, without trying to escape it or distract myself, the fear isn’t as scary as I imagined. In fact, just as I experienced at Rythmia, my self-care has leveled up and I’ve gotten back in touch with what I need in my life to feel fully embodied. As someone who unconsciously sacrifices himself in relationships, this is an important experience that I needed to witness.

I know most of us fear being alone, and as social animals, it is ok to desire connections with others. My painful experiences of the past have not turned me away from the desire to experience ever deeper love and evolution through my relationships.

And above all, I love myself for feeling this way, and for being brave enough to do it differently this time. For temporarily sacrificing monetary wealth and gifting myself this undistracted time to really explore my feelings and to heal.

I also expect that more emotional tides will come carrying ships of insights ashore. This is ok, I will let them come. I consider this moment a blessing of insight and surrender.

I have gifted myself the opportunity to deepen my relationship with myself.

About the painting: I channeled how I experience loneliness, as grasping from within to without. Loneliness to me feels dark, cold, and empty, separated from me yet crushing me at the same time. It is my first ever painting.


The pursuit of unhappiness

I’ve come to realize that I don’t have a great track record of knowing what will actually make me happy. Not that I’m generally unhappy, or particularly hard to please, but that the achievements I thought would result in my happiness seem to have about the same chance as any random event of yielding happiness in my life.

The fact is, life is inherently complex, and achievements made in the pursuit of happiness can have unexpected side effects. All the big milestones in modern life: career, marriage, family, your first house – we pursue them because we think they will make us happy, but they are at best unreliable engines. Lottery winners, by and large, live this irony because they generally end up less happy than before (to the continued bafflement of the rest of us). This leads me to believe that the achievement-based happiness promoted (and exploited) by our culture is fundamentally ephemeral.

In our “pursuit of happiness”, all we’ve been doing is making ourselves unhappy. I think there is a more sustainable path to happiness available to us.

For a moment, imagine your life as a chapter book of experiences. When you reminisce about old times, you’re reviewing previous chapters (or even wondering how to rewrite them). When you set goals and think about the future, you’re skimming ahead to future chapters.

In this magical chapter book of your life, the remaining chapters are being written as you experience them. So when you skip ahead in your book, you’re actually not reading your book anymore – you’re reading your *expectations of how it should go*.

Now think of a time you watched a movie adaptation of a book you love. People who didn’t read the book loved the movie, but you walked away disappointed because the movie didn’t match your expectations. The book and the movie were great on their own, but your expectations about how the story should go made the experience of the movie less enjoyable.

When you read ahead in your book of life, by holding onto expectations of how it will go, you’re similarly going to be disappointed. If instead, you release your expectations and just let life flow through you – you’ll enjoy the experience a lot more.

This isn’t an easy mental shift, but a good first step is challenging yourself to be relentless in your commitment to presence. When I catch my monkey mind drifting to the expectation “I’ll be happy when…”, I stop myself and find the gratitude of the moment. This is not always easy! But the more I practice, the more I’ve been able to find the gift in every experience that comes my way.

The next time you find yourself wrapped up in thoughts about the future chapters in your life, return yourself to the current page. You might just find the story easier to follow and the reading more delightful.