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Takeaways from coaching CEOs, founders and VCs

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Re: Takeaways from coaching CEOs, founders and VCs

#61

> “We’re all just big, complicated bags of emotion walking around.” 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 bat…

Thank you for sharing so openly! My career and business life has been at best mediocre by most common measures. The inner journey though has been immensely rich.

Re: Takeaways from coaching CEOs, founders and VCs

#63

Earlier quoted context omitted.

Oh thanks for that. Funny for you to observe that I've seemed “focused”. I've often though that to an outsider who isn't right beside me on this journey, I'd seem incredibly unfocused; since leaving my startup I've worked on almost 10 different projects or contracts. But what I've actually been doing, mostly very privately, is undertaking a highly focused project/experiment in deeply healing my mind and body, whilst…

Any chance you can point to the starting point for your project/experiment? Such as did you find a book that helped you to start asking a set of questions about yourself. If so, what questions seem to being making the biggest impact? Also, just wanted to say thank you for posting about this. I realize this really private stuff and I'm trying to find my own process for something similar to this.

https://news.ycombinator.com/item?id=21884667

Re: Takeaways from coaching CEOs, founders and VCs

#64
post #29

Earlier quoted context omitted.

I'm touched by your vulnerability and openness. It reminds me of a client who had built a billion dollar company and wanted my help building his next one. My immediate sense was that that was not really why we were talking or why he was here. We kept going and eventually I challenged him asking whether he had really built a billion dollar fortress to never need to be vulnerable. He broke down and we went deep, uncove…

Isn't this just essentially just a reflection of maslow’s hierarchy of needs? I mean, everybody has their demons, and the founder of the billion dollar company has the time and resources to face those demons by receiving top quality professional assistance, leading him/her closer to some kind of self-actualization. Whereas a large majority of the population (even in developed nations) are still struggling on much low…

No. Emotional healing became my top priority when I was effectively broke and homeless. I mean, I was crashing at my parents and friends’ places, but it was a profoundly miserable (and low-Maslow) state of existence.

Founders of break-out successful companies don’t just voluntarily embark on emotional healing practices once they reach the pinnacle of business success. They generally do that when they suffer a humiliating fall from grace. E.g., Early-career Steve Jobs and Jack Dorsey.

Also, Maslow’s model isn’t really broadly accepted in mainstream psychology, certainly not in any linear sense.

Re: Takeaways from coaching CEOs, founders and VCs

#65
post #57
post #53

Earlier quoted context omitted.

I always wonder if some place like YC could use a resident therapist/psychologist. Someone who meets with founders as needed or on a weekly basis. Might be helpful.. After watching the Showtime show "Billions", the idea seems like a pretty interesting innovation.

It’s a sweet thought but there would be far too many conflicts of interest for a single therapist to operate ethically.

Maybe.. there's probably a way to make it work though.

Re: Takeaways from coaching CEOs, founders and VCs

#66
post #59

Earlier quoted context omitted.

It is difficult deciding if this is inspiring or discouraging. The way you describe the Airbnb founders it feels like they had some intrinsic ability or talent. I think I have always viewed failure as not working hard enough, or smart enough, almost getting there but just not quite getting it right. Reminders that you may be failing because you might just not have ‘it’, and that no amount of work will get you there a…

> Are most of us just the kids in the middle trying to be the fast ones? Is self-acceptance, tempering of expectations and emotional growth a road to happiness or the silver medal of people who were just not good enough? I used to race bicycles competitively, and our coach grilled into our heads: "It's you vs. the track. The other racers are just obstacles in your way. You are not racing them, you are racing yourself…

I agree but it’s also worth noting that you should also be able to step back and consider how much of your self worth you want to define by how fast you ride a bike. There’s good reasons to set goals and “beat yourself” but also good reasons to not worry about it too much and “accept yourself“.

Re: Takeaways from coaching CEOs, founders and VCs

#67

> “We’re all just big, complicated bags of emotion walking around.” 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 bat…

I had a psychotic break and almost torched my career and I had a similar epiphany that emotional stability trumps everything. My only critique is if you frame emotional stability as a foundation to achieve all these other ambitions then to some extent you’ve circled back right to where you started. The emotional stability is it’s own reward and worth infinitely more than a successful business.

Re: Takeaways from coaching CEOs, founders and VCs

#68
post #57
post #53

Earlier quoted context omitted.

I always wonder if some place like YC could use a resident therapist/psychologist. Someone who meets with founders as needed or on a weekly basis. Might be helpful.. After watching the Showtime show "Billions", the idea seems like a pretty interesting innovation.

It’s a sweet thought but there would be far too many conflicts of interest for a single therapist to operate ethically.

It didn't even operate particularly ethically in the TV show either... still, seems to have been effective

Re: Takeaways from coaching CEOs, founders and VCs

#69

> “We’re all just big, complicated bags of emotion walking around.” 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 bat…

“when you really have it together yourself, you have plenty of positive energy to share with others.”

That’s a really important point. I tend to think about is an emotional gas tank. When it’s full, it’s much easier to be generous and help others. On the other hand, if your gas tank is empty, you are busy enough to keep yourself going and have no capacity for helping others or even for compassion.

Re: Takeaways from coaching CEOs, founders and VCs

#70

> “We’re all just big, complicated bags of emotion walking around.” 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 bat…

2 minutes to twelve, but definitely a candidate for best comment of the year.
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