Crash? Reboot

Jacob Chapman
Jan 24, 2017 · 6 min read

I attended the VC boot camp in Boulder, CO this past weekend. Several others have written about their experiences and I echo all of what they’ve said but I’ll try not to repeat it here. I do recommend you check out their thoughts though:

David Goldberg’s Reboot

Elaine Stead’s post

Charlie O’Donnell’s Reboot

A couple preliminaries:

(1) This is a bit non-linear because everything is still settling in my mind from the weekend.

(2) I want to once again say thank you to everyone involved in this last week. My cohort and the Reboot team could not possibly be a better, more soulful group of humans. I know our paths will intersect again. I love you all.


The boot camp takes place over 4 intensive days and its stated goal is quite straightforward:

“Uncover your authentic leadership style and become the best board member/investor/supporter you can be.”

Easy, peasy right? Wrong. The process for getting there isn’t something as simple as memorizing a punch list of best practices, rather it is radical self-inquiry surrounded by your peers and heroes. I would say that it is an emotionally challenging experience from beginning to end except that I don’t know if there is an end. Once you start the process of radical self-inquiry it only comes to an end when you reach enlightenment and I’ve got lifetimes (or a singularity?) left before that happens.

While I won’t share exactly what we discuss at the boot camp, I will say the magic comes not from any particular exercises or tools, it comes from the people involved. The Reboot team possesses an otherworldly talent for coaxing authenticity and truth out of people. They can even coax truths out of people who, like myself, have been lying to themselves for years.


While these words were never uttered this weekend, I feel like I heard them, felt them and said them many times. The room practically vibrated with silent perception.

I think what made this so powerful for me was that it broke down all barriers to vocalizing my sacred fears and insecurities. Once you accept that everyone in the room already knows who and what you are, there isn’t a reason to hold back.


I came to a number of realizations over the past several days and I want to share some of them here.

1) While I had a great childhood and amazing parents, I realized this weekend I was inflicting some of my own brain damage on my daughter. I hate crying because my parents hated crying. As I was growing up I heard, many times, something along the lines of “If you’re going to cry, I’ll give you a reason to cry,” or “son, you need to toughen up,” or “he’s just an emotional kid, eventually he’ll grow out of it.”

It turns out that I did grow out of it but not in a healthy way. I impose calm on myself at all times. I can be cold and un-emotional even with those I love the most and hold dearest to my heart. I want to be a warm person but even casual displays of warmth, like a shoulder squeeze, can be hard for me to take in. Worse yet, when my daughter cries I tell her to toughen up, to take a deep breath and that I won’t listen to her until she gets herself under control. I’ve been robbing her of the right to emote just like I’ve been robbing myself. No more.

2) I have a deep seated fear of being called out as an imposter and a fear of standing out. As a young kid I was incredibly outgoing and gregarious but somewhere along the way I learned to be small. I was a fat kid and hopelessly uncoordinated. I was mercilessly teased throughout middle and high school. I think it was there that I built a cage of introversion over my extroverted spirit. I’ve carried this cage with me everywhere I’ve gone ever since. My friends and family see the other side of me but not founders, LPs, business partners, etc.

While introversion served me fine 20 years ago, its spiritual poison to someone who wants to be 100% out there and professionally it is like carrying around 100lbs of baggage. I’ve noticed on many occasions that even a very small amount of alcohol is all it takes to switch me from introverted to extroverted and I’ve wondered why it turns an introverted me into an extrovert. This weekend I realized its because I’m not an introvert. I’m an extrovert and the alcohol isn’t for me its for my loyal soldier. He’s a lightweight and it puts him to sleep. [For those playing along at home the loyal soldier is a metaphor for my defense mechanism]

I’ve never liked that I use alcohol as a chemical crutch, its not that I drink to excess, its that I like to think I can run my own show without extrinsic assistance. Now that I’ve come to terms with this complex, I hope that I can begin to be a truer expression of myself. I believe I’ve outgrown the stifling confines of introversion.

3) The fear of not being a great investor has caused me to act like my image of a great investor rather than being entirely authentic to myself. In practical terms this fear has manifested itself in hundreds of insidious ways from influencing the types of companies I look at to framing my relationships with founders. When I ask myself about my purpose in becoming a VC, I have a crystal clear vision but if I look back at what I’ve been doing, it doesn’t track my purpose.

I’ve accepted the present dissonance between my purpose and my process. Once the dust settles on the last week I intend to bring myself into alignment.

There are other things bouncing around in my head right now and if there is one thing this weekend made clear, its that the onion always has another layer. For now I’m looking forward to sitting with these things for a few more days and seeing what settles out. Ultimately I know that now that I’ve begun the process of radical self-inquiry I won’t be stopping it anytime soon.


I worry that without the magic of Reboot it will be hard to continue the processes I began this past week. While I believe radical self-inquiry is a lifelong process, without accountability it can fall by the way side. As I jump back into the flow of life it is easy to see how all of this could get buried in an instant.

Over the course of the boot camp it became clear just how powerful a walk could be, particularly if the walk is with someone who listens to you on a deep level. I intend to incorporate a regular hike through the trails near my home into my regular schedule. Sometimes I will hike alone but often I hope to walk with a fellow traveler. My hope is that I can be an ear for others in need.


There should be a Reboot certification, decoder ring, secret handshake or tattoo. If you are a founder you should be looking for Reboot VCs, if you’re a VC you should be co-investing in Reboot founders with Reboot VCs and you should be sending your founders through the program.

If you think that’s silly, I’d challenge you to read all of the posts written by Reboot alumni and still walk away thinking Reboot isn’t a major fucking advantage. It turns great founders and investors into Lightsaber wielding Zen monks.

A couple quotes I found instructive for myself this weekend:

“I’m smart enough to know that I’m dumb. The first principle is that you must not fool yourself — and you are the easiest person to fool.” — Richard Feynman

“The goal of life is to make your heartbeat match the beat of the universe, to match your nature with Nature.” — Joseph Campbell




Jacob Chapman

Written by

Managing Partner at & cofounder at We believe healthy founders = healthy returns and that venture done right is an impact business

Jacob Chapman

Written by

Managing Partner at & cofounder at We believe healthy founders = healthy returns and that venture done right is an impact business

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