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.

For me, focus is simply about depth over breadth.

If you want to do high quality work and enjoy it, you need to clear up your schedule to give a particular endeavor the time it deserves and then some. You do this by shrinking the scope of what you're working on down to something manageable, something you can do a stellar job on in the time allotted. That requires saying no to everything else, even things that are promising. You can get to those later.

If you want to do mediocre work, then take on huge projects with a ton of responsibilities, and try to work on them all simultaneously. Not only will the quality of your output suffer, but as an added bonus, you'll earn a packed calendar.