Takeaways from coaching CEOs, founders and VCs

This has been the most important discovery from my startup journey, and the topic on which I now place the greatest focus.

I was in the YC batch of winter 2009 – the one that included Airbnb. It was a small batch, so we all got to know each other pretty well.

There was something that really made the Airbnb founders stand out from the rest in that batch.

It wasn't that they seemed to have the best business idea; as has been widely written about before, PG and the other YC partners thought their "eBay for space" concept was stupid and would soon fail, then they would hopefully move onto something more promising.

But for some reason, everyone just assumed that these guys were on a sure path to huge success, and in the batch voting on the most promising startup just before demo day, they won by a huge margin.

I didn't grasp this at the time, but over my own startup journey I realised that the factor that made them seem so promising, and the one that held me back and all the other companies that didn't make it, was emotional strength and stability [1].

The Airbnb guys just really seemed to have their shit together emotionally. Not in any bulletproof, infallible way; they had their weaknesses, and made mistakes like everyone else, but they had a unique ability to cop the hits, learn the key lessons and bounce back better from every challenge and setback, and thus they kept growing and progressing at an astonishingly rapid rate.

I, on the other hand, whose business concept was considered by some others to be at least as solid, was far more sensitive and emotionally fragile, and I would become increasingly scarred by setbacks and criticisms, and paralysed by fear of further torment.

Though we battled on for five years, I became physically and mentally exhausted, and ultimately had to step away to let my co-founder and a new CEO to take over.

In the six-plus years since then, it's been my primary focus to overcome all my deeply held traumas and unhealthy emotional/behavioural patterns, and to become as grounded and rounded a person as possible.

And as my healing journey has progressed, any ambitions I held to achieve business success on par with the Airbnb founders has faded, and been eclipsed by the realisation that in order to do _anything_ well – from running businesses and leading social/political movements, to simply having successful friendships/relationships, a healthy family life and a physiologically healthy body – a healthy emotional foundation is of prime importance.

And as I methodically work though my emotional baggage, all those key aspects of my life - career, family/friendships, and physical health - have steadily improved, but my ambitions and visions of a desirable future have also significantly changed from what they were when I entered YC.

Exactly what that means for my ultimate career/life outcome is still very unclear, and to me, these days, not especially important.

But one thing is for sure; whereas I'd initially hoped that getting into YC would put me on a path to building a "unicorn" tech company, the way it ended up changing my life has turned out to be far more profound.

[1] The other thing that made them stand out was that they were by far the most nice and supportive to everyone else in the batch, which I've also since learned is a sign of emotional roundedness and wholeness; when you really have it together yourself, you have plenty of positive energy to share with others.

This is a really provocative and powerful post, you have a unique coaching perspective being grounded in somatic trauma therapy.

As a fellow male (British) ex-startup founder I can certainly relate to being disconnected from my emotions. What are some of the most effective means for encouraging your conversation partners to start listening and tune in?

Also, what might be some questions to ask a potential coach to see if the relationship would be a good fit?

It amazes me that our educational system at every level teaches so much information, knowledge, and analytical skill but virtually ignores teaching social and emotional skills, I guess because we can't test them in a way to stratify learners.

Most of my practice is leading clients and students through these exercises, which I call the basics or fundamentals of leadership, initiative, and entrepreneurship. In every other performance-based field we don't lecture and test but teach the basics and perform -- sports, acting, singing, musical instruments, the military (basic training).

A few exercises make master the following a matter of rehearsal and practice, not necessarily easy or fast, but straightforward and effective:

> The hardest of hard things to deal with for all these people (including myself, when I work with my own coach), no matter the level of success, is the perpetual, ever-recurring loop of mental chatter, difficult emotions and body sensations. To frame differently, it’s our capacity to be with what’s alive and right in front of us, whether we like that or not in any given moment.

I'm a follower of this priority aswell. I can't tame the onslaught, but I can ensure that my focus is spent in the right places.

I'd love to hear more about this topic as I often have issues communicating what I mean by that, as many other people in my environment want to see get things done "one after the other".

Over the past year I have made a conscious effort to do this in all my conversations. Two things really stood out for me: first, I was a REALLY bad listener. I would interrupt a lot because I assumed I knew what the person was getting at.

The second is that sooooo many people do that as well and it's incredibly frustrating to be interrupted like that. What's worse; about 75% of the time they are completely wrong about what I'm about to say. Just as I was when I did this. Not long ago, I had finally had my fill with an Amazon support rep and had to interrupt his constant interruptions and say, "You have GOT to stop answering questions I'm not asking." He thankfully realized what he was doing and took a step back to listen to what my problem really was.

Another thing I've noticed is that the smarter the person is and/or perceives themselves to be and/or are told they are, the more they do this. Which means, this happens a LOT in technology circles, which is unfortunate given how critical communication is to our jobs.

It has really made a positive difference in how I deal with people though. In listening to people, and I mean really listening to them (with intent to understand and not just to reply) you learn so much more about that person. You notice things about them that you hadn't noticed before. You come to understand them at a deeper level I feel. This kind of listening is definitely something I'm trying to continue.

I also acknowledge your reference to your own coach. It amazes me (and I’ve been doing this since 2006) how many other business coaches I meet who don’t see the value in having their own coach. That says a lot about a career (I wouldn’t call us a profession) that is loaded with unqualified shonks.

I look forward to re-reading this piece many times. Thanks.

[1] An artefact of my clients, who are generally $2-$20M ARR with limited prior business experience, and my own business model which engages leadership teams more and longer, more regular coaching sessions.

What I had been holding onto, for hope, for distracting my mind, was hope for my very ambitious projects. The first difficult lesson in letting go was ~4 years ago; I really haven’t kept track of time, there’s no value in that I’ve found. I was developing a platform for the yoga community and successfully launched with decent number of yoga instructors actively using it, and was ready to scale - with the help of my then girlfriend and business partner I brought on when platform was ready to scale, who mainly was tasked with outreach and support. I struggled for a few months to find a way to keep this project alive and growing - I couldn’t. Perhaps fortunately design is where my skill development lead me, and so over the last few years a main focus I had was redesigning the platform of which I completed 80-90% of the new version, however I let go of that many months ago now - I just can’t handle managing or arranging for the next steps for such a relatively complex project; I know the market better than most, the new updated model if implemented would scale very quickly - I am certain if I could write an executive summary to explain the game plan I could convince anyone the vision will be successful, except there’s no point because I can’t execute or guide the execution of it.

All around the same time as struggling to keep the project alive, to scale: the relationship with my then girlfriend fell apart primarily due to my difficulty coping with the pain I could no longer be the stability she needed, I had to fly back from our outreach in Silicon Valley to watch my father who had requested euthanasia - but denied it - suffocate, drown to death in his hospital bed due to his body being weak and him catching pneumonia (pneumonia his lungs) in the hospital - watching along with my mother and sister; https://mattamyers.tumblr.com/post/120321181606/my-father-pa.... It was ultimately the grieving of my father’s death that reduced my available tolerance for the difficulties of the relationship to zero.

As I say, my first project has always been myself - trying my best to organize the next treatments, to try to problem solve what else may be going on. Healing myself has been difficult on its own though with my executive function being greatly disrupted due to the pain, and though I have tried again at different times - mostly after when significant healing has occurred, I still can’t handle the normal stress of moving a project forward, of hiring and managing others. I don’t know if I will ever be able to handle any normal life stress - whether for what I consider my life’s work, writing a detailed book of my journey, moving my projects forward - a network of health-wellness differentiated platforms to help shift society toward a healthier path, friendships or more - I simply am stuck from moving forward with all of this; this has difficulty psychologically of course. It is rare that the conditions are right that allow me to stream of consciousness write like this, where I write everything in one go, which allows there to be some organization inherently in the thoughts - otherwise I’m generally unable to organize a longer story from pieces written at different times - a part of mental organization tied to executive function.

The turmoil from not having a stable foundation for my brain, or perhaps mind to stem from, to develop patterns of behaviour, autonomous nervous system habits, executing thoughts toward behaviour allowing me to move forward without being constantly interrupted by physical pain, psychologically has been varying degrees of hell on Earth.

Two years ago it seemed I was better able to trick myself, delude myself, into thinking that I would soon reach the tipping point where enough pain would be healed where my executive function and life could begin to be rebuilt; https://mattamyers.tumblr.com/post/160104127401/on-days-like.... It’s however been 2 more years of stem cell treatments with unimaginable difficulty day to day, week to week, year to year, of struggle trying to cope - cycling through patterns and attempting to maintain a routine to provide as much stability as possible for myself.

When I write something long like this I wonder if it will be the last coherent piece I write to share my story. It feels cathartic to share my story, as we’re designed or evolved to story tell to pass on knowledge - however it is the rare time where I am able to compile something as clear as I feel this is, and so unfortunately it can’t end up part of my routine. I step carefully to not touch on details of my journey including near constant occurrences of incompetence, abandonment, lack of adequate support to not too strongly trigger emotions, stress including post-traumatic stress, that my nervous system just can’t handle due to the constant injection, sensitization of my nervous system.

I no longer care to actually share my vision for my projects, it isn’t useful to have hope - in fact optimism increases the contrast creating higher peaks and valleys with the pain, reducing how stable or flat foundation is possible. I could be hopeful, optimistic - I’m not broken that way - however ultimately I’d need the help of others to move my projects forward and that doesn’t happen, no help for me day to day or organizing treatments or someone problem solving for me what else could be going on with my nervous system, and no help for me for my projects; I can’t even ask for help any longer and don’t want to because the thought of moving forward engages executive function, your mind and thoughts lead to the body preparing itself for action - which for me, my body trying to engage triggers, tries grounds into the pain — aversion. It seems everyone has difficulty understanding just how locked up I am with moving forward in life, most everyone - especially doctors - not willing to read anything long form like this either.

So currently I am in a very dark place, more calm today after the storm that this past week has been. I do have another stem cell treatment middle of January already booked and organized, that at least today, I feel like I’ll make it to. A month ago I found out after doing a microbiome test I have an h.pylori infection - probably for many years now, that if treated may or may not reduce pressure on my body and reduce symptoms. It took me until a few days ago to order the supplements the doctor wanted me to take for a few weeks before starting antibiotics for a few weeks. There are other treatments and other diagnostics I still need to try organize. I normally share the actual incidents and causes of physical injury, though I don’t care to at the moment, and I am getting mentally exhausted now so my writing will start to fall apart if I continue trying to add to this and would start adding exponential more stress if I tried to push.

I don’t expect anyone to read this - though a thank you to other commenters who inspired me with their openness, and to LeonW’s thoughtful responses that let me feel this would be a safe space to share. And apologies if anything is incoherent, too mentally exhausted now to proof read what I wrote.

For exame, given the first point (we're emotional) a comms void can often be fill with false assumptions. Going forward is going to go sideways.

Yes. We can improve our inner selves. But sooner or later we need to interface with others. That innerface is comms.