The surrender experiment (year-1 results)

A quest to trade in "understanding" for magic

Welcome entrepreneurs. I’m so glad you’re here.

Writing you today from my home office in Michigan, looking out a window at the fifth consecutive sunny day. After scheduling this post I’ll walk around the neighborhood in the first 50-degree day of the year. The snow is melting, and I can feel the world waking up. If that’s not worth a smile, I don’t know what is.

Some more news worth a smile from my world. Longtime readers know that meditation is a big part of my life. I’ve found it to be an incredibly effective tool for leadership development, both because it helps one cultivate equanimity, and because it’s a direct path to better understanding your mind (your primary leadership tool). So I was pretty stoked when, having been introduced to me by a reader of this newsletter, the CEO of Mindful Magazine serendipitously asked me to collaborate on a series about mindful leadership. (PS thank you to that reader for sharing SMS. If you’d like to, button’s below, and I am so grateful.)

Share Second Mountain Startup by Ryan Vaughn

Fast forward a month, and here’s the first of 4+ pieces on Mindful Leadership, this one about the power of talking about failure.

Speaking of serendipity, I mentioned in a previous issue of this newsletter that my path to working as a coach to scale-up founders at On Deck was also an interesting one, and I wanted to tell that story today. It’s one highlight among many, all part of a lifestyle experiment I’ve been running for over a year now.

Can’t wait to tell you about it.

The Surrender Experiment

“What if there is no way the world should be and no way the world shouldn’t be? What if the world just shows up the way the world shows up?” — Jim Dethmer, Diana Chapman, and Kaley Klemp. The 15 Commitments of Conscious Leadership

Bust your ass, but roll with the punches.  

After 15 years of trying to wrench reality to conform with my latest 5-year projection, over the last year+ I've been living out my own version of Michael Singer's The Surrender Experiment, and I imagine I won't go back. 

Here's Singer describing the approach:

“The rules of the experiment were very simple: If life brought events in front of me, I would treat them as if they came to take me beyond myself. If my personal self complained, I would use each opportunity to simply let him go and surrender to what life was presenting me...My formula for success was very simple: Do whatever is put in front of you with all your heart and soul without regard for personal results. Do the work as though it were given to you by the universe itself—because it was."

Or the way I remind myself in the heat of craving: "Universe, I will take care of the quantity, you take care of the quality and direction."

We're taught to take charge of our lives from an early age, so giving up agency in favor of a cosmic dance with life, if you’d have suggested it to me five years ago, would have seemed backward and stupid. But a year into this crazy experiment, I'll tell you the last year has been one of the most magical, serendipitous years of my life. 

Here's a recent example:

I had spent the better part of two months building a leadership development peer group -- a long term adventure I'd called "Sangha," designed for entrepreneurs who had reached their definition of success and were looking for what comes after (a lot of this conversation). I had designed all the content and programming, and had commitments from five entrepreneurs (two shy of the seven I was targeting for launch). 

I did all this work, and then didn't touch it for a month.  It wasn't intentional.  I got busy.  I sat down at my computer one day and realized that it'd been a month since I last thought about the group. 

There's a thing that happens, when you're close to launching a creative work and immediately before the finish line the whole thing seems stupid and pointless. Julia Cameron calls these "creative u-turns" and Steven Pressfield lumps them in with other mental roadblocks-to-be-overcome as “Resistance,” and either way they're a common reaction to the fear of presenting a bit of your soul to the world's judgement.  

I figured that's what had happened, so I committed to brute-forcing it across the finish line. I created an outreach blitz, targeting some of the most successful entrepreneurs I knew.  I worked out all the required steps on a Monday, and committed to sending the emails out that next morning. 

On Friday I realized I still hadn't sent those emails.

You will forgive me if I don’t attempt to replicate here the venom with which my inner critic spoke to me then.  The scorn and the shame.  What a slacker I was. A lazy has-been who is so scared, so in need of the world's approval, he can't even force himself to launch a project on which he’s spent months.  Having grown up in the world of competitive sports, this was all very motivating.  All my mental machinery told me to just do it.

“What if the great opportunity of life isn’t in trying to get the world to be a certain way, but rather in learning from whatever the world gives us?” — Jim Dethmer, Diana Chapman, and Kaley Klemp. The 15 Commitments of Conscious Leadership

But I didn't. Armed with a long-term meditative practice, supported (fortunately) by a half-year financial runway from exiting my company, emboldened by Singer's approach (which, despite its incompatible-with-western-culture philosophy, still led him from a yogi in the woods to the CEO of two public companies), and fueled as much as anything else by curiosity, I decided to let it go. For the first time, I let go of the outcome I wanted to drive and instead listened to what, as near as I could tell, the Universe was asking of me. 

My inner critic judges me as I write this.  I felt that judgement then, too.  It felt impossible to justify but I let go anyway, and for those reasons. The sixty days of work, the entrepreneurs already committed, the little bit of identity I'd already wrapped up in the project.  I let it all go.  It felt like I'd given up, but like it still might, in some way I couldn't yet understand, work out ok.  Like dropping a Plinko ball and, despite the odds, expecting a jackpot.

It didn't even take a week. 

Six days later a chance email from On Deck, the preeminent community-builder in the startup world, landed in my inbox announcing the launch of On Deck Scale (ODS), their first attempt to build a peer-leadership program designed for scale-up entrepreneurs.  I replied, and the next day I was talking with the Program Director, Ty Walrod.  He told me what he was building, his vision for a transformational program for some of the top entrepreneurs in the world.

"I think I built that already," I said. 

Fast forward a couple months and Ty and I, along with two other amazing coaches, are now bringing 80 of the top scale-up entrepreneurs in the world on an incredible adventure called ODS.  The essence of Sangha lives on in ODS, but it’s become so much more.  By letting go of what I thought I wanted, I was handed an opportunity I couldn't have dreamed of. 

You may say coincidence.  Maybe so.  But then coincidences happen constantly these days, in areas big and small. 

  • After deciding that the NLP certification training I wanted to take was too expensive, the organization randomly reached out to me to offer me a $500 course for free.

  • A chance encounter with a mindfulness teacher in Jackson, WY, which I almost bailed on in lieu of something more “productive,” lead to me doing a series on mindful leadership with Mindful Magazine.

  • I wrote the most popular issue of this newsletter after giving up on the article I was trying to write and just writing what I was feeling.

  • So much more…

Einstein said there are two ways of relating to life: one, as if nothing is a miracle.  And the other, as if everything is.  After years as an intellectually-superior Atheist, I'm finally beginning to see the world’s spiritual axis.

“How could I possibly explain the great freedom that comes from realizing to the depth of your being that life knows what it’s doing? Only direct experience can take you there. At some point there’s no more struggle, just the deep peace that comes from surrendering to a perfection that is beyond your comprehension.” — Michael Singer

To manage expectations, let me say that Singer is on another level. I get the sense from reading his story that he would, and has, maintained equanimity in the midst of a hurricane. I’m not there yet. There are still times in which everything inside me panics, and I wrench the steering wheel of a situation toward what I think I want. But I’m getting better, every day. My grip is loosening as I learn my fear patterns more intimately, and catch them quicker in the process. My reptile brain is learning, slowly but noticeably, that it will, truly and for all, be ok.

The Surrender Experiment continues to be, without a doubt, the hardest challenge I’ve faced in life. But after a year of living to learn instead of living to win, I wouldn't trade life's daily magic for all the five-year projections in the world. 

(HT: Soma Mandal, Joel Christiansen, and Compound for editing!)

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I’m an executive coach for startup founders, a role in which I get to help founders expand into leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here. Here’s a more detailed bio.


One: What we talk about when we talk about running (Murakami)

“Most runners run not because they want to live longer, but because they want to live life to the fullest. If you're going to while away the years, it's far better to live them with clear goals and fully alive than in a fog, and I believe running helps you do that. Exerting yourself to the fullest within your individual limits: that's the essence of running, and a metaphor for life-and for me, for writing as well. I believe many runners would agree.”

This is why I practice.

Two: Study the % of people who, when left alone, decide to shock themselves (UVA)

When left alone in a room for 15-minutes, 70% of men decided to give themselves a painful shock. 25% of women decided the same.

Doing nothing is harder than getting a painful shock, turns out. If you’re struggling to meditate, this is normal. And you can do it.


Three: Best video of Perseverance landing on Mars (YouTube)

In case you didn’t already see it, here’s an incredible video of the Mars Perseverance Rover landing on Mars. I watched it with my boys, and they asked when they’d get to go to Mars. I told them 20 years. I might not be wrong.


Four: What I Worked On (Paul Graham)

I’ve lived four lives (future NBA player, Jim Morrison impersonator, hotshot tech founder/CEO, and, now, Me). This is very different from the career path we’re told to follow, but I wouldn’t change a thing. Paul Graham’s career autobiography, involving art school, programming, building companies (including Y-Combinator) and writing essays, refreshingly normalizes my kind of non-linear career path.

TL/DR: YOLO, so do you. It’s probably the financially smart move.


Five: The Soul of an Octopus (Feld Thoughts)

Animals with parallel brains in each arm, who may or may not experience time non-linearly. Not sci-fi. Octopuses. In real life.

Thanks Brad Feld for sending me on a really interesting Google deep dive, which like the best deep dives ends in awe-struck wonder at just how little we know about how it all works.


My hunch is some readers will think I’m crazy after this week’s essay. I’ve made my peace with that fact. I had to share my experience anyway.

If you’re someone with whom this approach makes sense, this post is for you. I’d love to hear from any other fish crazy enough to swim against the current.

Thanks for reading,


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