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Takeaways from coaching CEOs, founders and VCs (leowid.com)
533 points by LeonW 5 months ago | hide | past | web | favorite | 111 comments

> “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 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.

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, uncovering some of the deepest trauma I'd seen someone go through when they were 4 years old. From there, everything shifted and things took a very different direction. It's those kinds of insights, when as you say "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 in order to anything really 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.", once we really get in touch with our inner world, things shift dramatically and what has meaning to us changes. That doesn't mean that we don't want to to continue having a meaningful contribution to the world, but the sense of ego-striving that is often just a mask for our wounds can gently fall away and allow us to walk through life a little more freely.

My learning has been whether you get to the billion dollar level or not, the untouched wounding eventually comes through and takes its toll if it stays unaddressed. It's stories like yours and the one I've described that make coaching the most meaningful thing I've done in my life to date.

Cheers for that.

> the untouched wounding eventually comes through and takes its toll if it stays unaddressed

This nails it, and I think a lot about this in the context of the very public cases of "unicorn" CEO falls-from-grace in recent years.

> That doesn't mean that we don't want to to continue having a meaningful contribution to the world, but the sense of ego-striving that is often just a mask for our wounds can gently fall away and allow us to walk through life a little more freely.

Very nicely put, many thanks.

Great book on this topic is I Don't want to talk about it by Terrance Real

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 lower levels of the hierarchy, such as fulfilling their "safety needs" (e.g. employment, health, etc).

I would therefore argue that the "untouched wounding" remains buried for most people because they are never in a position to address it, and the "ego-striving" remains essential part of their survival toolkit. There is simply no "salvation" in this regard for most people and it's quite sad.

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.

There are a lot of rich people out there who have all of their Maslovian needs met but who are absolutely miserable. What happens is that they never really figured out what they wanted out of life, they just assumed that having money would allow them to get it, and they'd figure it out later. But then they get money, realize that they are still miserable (because they still don't really know what they want) and then sink into deep existential despair because if you have a billion dollars and you're still unhappy, now what the fuck do you do?

Ron's second law: the hardest part of getting what you want is figuring out what it is.

This is a prime example of survivor bias. Most homeless people don’t make it back to the top.

I tried to be clear that I wasn’t “homeless” in the sense of living on the street.

I just couldn’t make rent (ironically I had to Airbnb out my room) or easily afford food/bills, so needed to sleep at parents’/friends’ houses for a while as I worked to get back on my feet.

Plenty of people go through this, due to a business/career/relationship breakdown, and recover to a good life, and it’s very common for people to start focusing on their emotional/spiritual wellbeing when they hit rock bottom (e.g., join 12-step programs, counseling etc).

People who are chronically homeless are in a different category, but it’s widely accepted that chronic homelessness is usually linked to mental illness and/or addiction (which is a form/symptom of mental illness after all).

I’ve spent a lot of time thinking about how outcomes for chronically homeless people could be improved if they had access to the kinds of support and healing techniques I’ve used. Given the opportunity, I’d be very willing to support research into this in the future.

Invoking concepts like “survivorship bias” is unhelpful in a discussion like this; my story is obviously anecdotal, not an academic paper or claim of scientific evidence. But that aside, “survivorship bias” in this context would require the existence of a whole lot of people who attempted the same approach to emotional healing that I did but failed to improve their lives, and there’s no evidence for this.

I couldn’t disagree more. I think free healthcare, aides for rents, food, etc. when you can’t afford it should be a human right. Some people manage more than others, and we just blame this on mental illness.

> Some people manage more than others, and we just blame this on mental illness

I agree, but I don't accept that this has to be immutable, and it would be a very bleak world/future if it did.

Rather than a world in which a class of people just has to accept a disempowered existence with basic services and resources provided, I hope for a world where effectively everyone can have agency over their own life, and aspire to good health, good relationships, and a reasonable level of material wealth.

That hope is part of what keeps me determined to explore the possibilities in this field; to see what kinds of improvements I can attain in my own life, then think about how these approaches could benefit others, including those who are currently written off as "mentally ill" (which I have been at certain times in my life).

I think I understand what you mean with that and agree with it in principle. However you should keep in mind that you are a person with a "business mindset". There is plenty of people out there who may well have something valuable to contribute to this world, but have no chance of getting an economic return out of that. This can be due to a lack of economic mindset/understanding/education or also just due to the type of value one is able to provide not fitting any monetization model. I believe that a modern society can and should afford to relieve their members from existential fear related to biological needs. That is not about taking away aspiration and agency.

The combination "something valuable to contribute to this world" and "have no chance of getting an economic return out of that" sounds like a market failure, and something that could/should be fixed, both for the benefit of the individual and for society.

There are indigenous Australians in remote communities, who grew up and remain living in cultures that have little familiarity with modern commerce, but who produce artworks that sell for thousands of dollars on international markets. The proceeds are invested back into those communities for their future benefit. This happens because systems have been established to make it happen.

So I'm not convinced that there is an immutable state in which a certain class of people, while providing valuable contributions to society, cannot reap any economic benefit or improve their own lot in life.

Can you describe an example of this situation that you've observed?

... in other words: based on personal observation, I believe that the correlation of personal wealth and value contributed to society is not strong enough (which doesn't mean there's none) to justify making one's existence dependent on it - in a sophisticated society which could easily afford otherwise.

To add to this, when your ego mind drivers lead you to success giving you potentially unlimited resources - money and time, it is easier to maintain coping mechanisms of distraction - unless there's some traumatic or stressful enough event that "cracks" someone, causing an impetus and necessity to explore change.

Western philosophy starting from Ancient Greeks has offered a variety of coherent life philosophies that both help with untouched wounding and ego-striving. The books provide cheap and accessible salvation which is just not in demand by most people and it is quite sad.

Wow. Thanks for that.

When Airbnb popped up on my screen I was in Siberia having my website rewritten from scratch after 8 years of spaghetti code.

It was the same thing and Airbnb which was just designed better (in 2008).

When a couple of years later I finally realized they destroyed my business it took me some time to admit I didn't really miss a chance: I had none to begin with.

I just don't have what it takes to grow a business to those levels.

In my case it's probably not an emotional issue, but it has still a lot to do with personality.

I guess my takeaway is: not everyone can be a CEO of a unicorn and this is fine.

> I just don't have what it takes

Try not to put yourself down like that; it might just be that you were already grounded and emotionally centred enough that you didn't need to chase the riches and fame :)

I guess you are right. I think my biggest block to success was that I was just to happy! :) The very reason I had started that business in 2001 was because I wanted to travel full time.

I managed to do that and I was already in a "too good to be true" state of mind.

The happiness and fulfillment I got from those years are now my own "essential oils" for the occasional hard times. When something goes wrong I just have to go back, smell a drop of that, and I'm back on my feet in no time.

I wasn't just looking to grow the business, it was a mean to an end.

Thanks for sharing this, if you don’t mind to elaborate, what aspects of personality do you think have more weight? Have you consider partnering with someone who complements those aspects?

My anecdotal opinion - pure tech people don't usually make good founders because they are too realistic and grounded.

A company needs a visionary, someone who is at times even blinded by their optimism and vision. You pair that visionary with a strong grounded realist, and they balance each other out. There are times when both are needed - to either take a leap of faith (risk) or mitigate/avoid risks.

But this dynamic will also only work if these founders have good communication and respect towards each other, otherwise friction can turn into bitterness and resentment.

I think we should not force ourselves to become something we are not.

If you've got the Unicorn CEO personality, go for it as it would be a pity to be stopped by fear.

If you don't have it, why chase the social norm of the day? You won't make it and you'll be miserable.

Again, not everyone has to be a CEO.

You can be great at something else but you need to be blind to the social requirements of your age.

What is cool today wasn't cool 20 years ago and won't be cool in 20 years time, anyway, understand this and you are free.

Maybe we will look back at the "be big or go home" days as a skewed approach to business fuelled by VCs need for high returns.

And yes, today I look for partners who can complete me, as I have millions ideas but I only enjoy the first part, where you go from 0 to 10, growth 10 to 1000 is boring for me and I'm not good at it.

BTW, if anyone is good at it, I have great ideas in the Vacation Rentals (Airbnb) market, my contacts are in the profile.


I agree. In my case it's not ethics as I enjoy working hard, but as it gets less interesting and goes in growth phase I'm already chasing the next idea.

I was just kidding btw. The AirBnB founders just got lucky.

They knew the right people to get into Y Combinator. Their original idea for air mattress rental is a really dumb idea. It's a miracle that they got accepted into YC.

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 are kinda brutal.

I always think back to being 8 years old and running with my friends. Some kids were just faster, others were slower. No one was training or working at it, no one was reading up on techniques at night. Some kids were just better. 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’m confident there’s a way it can become encouraging.

Learning the skills (programming, design) to build an early stage web/mobile product is not hard; many many people already have done or could do that.

Equally, plenty of people can easily identify political or social problems that just need a confident and capable leader to drive reform.

The temperament/emotional side seems more innate and immutable, but only because broadly accessible ways of transforming one’s temperament are not widely known or deeply researched.

This is one of the main reasons I’ve gone so deep on the topic; beyond just the self-motivation of improving my own life, it seems like it could be quite significant if many more people in the world were able to overcome their inner obstacles and achieve better outcomes in whatever they were seeking to do.

Temperament definitely changes with age at least, the timescale for personality shifts is just so long that it’s difficult to manufacture or steer them.

> 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 was a mid pack racer, but that mentality, of focusing on personal growth was huge.

You define success for yourself. And by your measure, others may be more successful on your own measure, but they are not you.

I'll also add the trite: "hard work will be talent if talent doesn't work hard." My brother was a natural racer, but he hated to practice and got beat by riders who were better conditioned all the time.

He never had to beat them, he just had to beat himself.

Wasn’t that kind of op’s argument? You can focus on beating yourself all you want, if yourself isn’t the best, then you will never win the Tour de France.

If you don’t have the potential to win The Tour, then should you even be trying to? Sounds like a lot of effort, might wanna invest it somewhere else or redefine your cycling goals.

I run marathons and I don’t beat myself up about winning because I don’t have the potential to be a world class marathoner. Even if I trained twice as hard as Kipchoge. I just don’t have it.

Same with boxing. I train 4x/week because I enjoy the exercise and mental relaxation. Punching people in the face is fun. But I don’t compete because I don’t have the talent to make the pain of competing worth it.

But when it comes to writing software and running a business, you bet your ass I’m giving it all I got and want to “beat” (hard to define) everyone else. Because there I do have the potential.

What kind of bike racing was that? Because road racing is quite the opposite, the other competitors are everything while the properties of the course are just a minor influence on the all-defining question of which wheel to suck when. But those coach words are still wise and apply even there, if your goal is not to maximise winning but to maximise motivation and happiness (which would actually help winning long term, but the ratio between winners and losers is so bad in that game that you should focus on happiness nonetheless)

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“.

I think life is incredibly unfair, more so than people care to admit. Personality, disposition, early-childhood parenting, where you grow up, physical appearance, intelligence, family, surrounding, even country you're born all are determined outside your control. Yet these factors are what more or less determine how successful you are going to be.

The way I look at it, if you're posting on HN, you've mostly likely been dealt very favorable hands in grand scheme of things. So I try to be thankful for what I have.

For all each success stories like AirBnB, there are hundreds of not-so-successful ones with equally competent and gifted team. Luck plays a huge part.

Interesting approach and I feel the burn of this quite often. Peers of mine have much greater hands dealt and I've worked quite hard to get where I'm at... I get bitter sometimes because theirs nothing I could have done to set up greater nets for myself or anything like that.

The disparity of equality and seeing the top after coming from the bottom makes you realize just how unequal things are and how it might just never change and get worse.

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.

By the way, since someone has already asked (and I generally get requests for more info when I write about this stuff here) people are welcome to contact me if they want to know more about techniques I’ve used for emotional healing.

I’m working on some written material to share my learnings with others who may benefit from it, so if you get in touch I can share it when it’s ready.

Email address in profile.

Thanks for sharing your story.

My own story has some similarities to yours -- I joined an elite startup accelerator straight out of university, thought I had a bunch of pretty damned good business ideas to work on (and looking back, I did -- I had a pretty good understanding of business strategy, engineering, product design, etc) -- but then ended up bouncing between jobs and quickly-aborted startup attempts, before crashing pretty hard around age 26-27. Meanwhile plenty of my peers steadily moved forwards while a few others shot off into the stratosphere.

I actually knew Leo Widrich, author of the article, back in university! Two guys had set up the "Internet Entreprneur Society" at our university in the British midlands, I was helping them run it as they were about to graduate. Leo was an Austrian business student with lots of passion and just starting to learn about tech startups. He ended up working with one of the two guys I mentioned (Joel Gascgoine) on some tweet scheduling app which is now apparently worth about $80m :) Small world!

As for myself, after several setbacks in my late 20s, I realised I had a whole bunch of psychological/emotional issues stemming from an unstable childhood. What's surprising is that with time and effort all these problems were, in fact, fixable... and through lots of reading and self-work I've managed to fix 80-90% of these issues. Like you, my desire to build a startup business empire has diminished greatly, and, nowadays, after learning all the things I've learned, I've rethought my career plans, and figured out a new direction to go down which ties together the various things I'm interested in, and which I'm very confident I can succeed at. (I'd rather not go into details in a public forum, but's it essentially a path that combines intellectual and technological projects).

(For those in a similar situation, the best books I read were: "Adult Children of Emotionally Immature Parents", "Running on Empty: Overcoming your Childhood Emotional Neglect", "Complex PTSD: From Surviving to Thriving" and "Psychology of Self-esteem". I also recommend the post "What is a central purpose in life?" (plus comments) [1] for a discussion of how to integrate one's career values).

[1] http://aristotleadventure.blogspot.com/2008/05/what-is-centr...

Fantastic, thanks for sharing.

“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.

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.

They had Amy who was a trained psychotherapist during both 2015 and 2017 when I went through. Anyone could schedule time to talk to her at anytime but it was generally used for resolving founder conflicts. She went off to be an executive coach but I am sure they still have someone like that.

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

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

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

Tom, could you please share how you've worked on your emotional wholeness? This is an issue I recognize in myself, but do not know how to begin to heal.

>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 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.

I feel also one has to realize that he can't have it all in life. I think its almost impossible and out of our nature to be able to achieve greatness in all fields. You might be the most successful CEO in the world and having the most money in the world but that doesn't mean that you are going to have and lead a successful family life as well.

Same way you can be successful at having a nice family and a loving partner etc but that requires time, time which you'll not be able to invest the time that being a CEO requires.

Thats my personal take from life so far - you have to decide what you want to be.

This has to be one of the best comments I've read on HN.

I've failed many times in my life on different adventures and it has always been because I couldn't see what was really going on due to frustration, emotional traumas, etc. Of course hindsight is 20/20 and I can see that a lot more clearly now that I turned 40.

Thanks for sharing that personal insight.

My career is far from the place I want it to be and I've emotionally dealt with the setbacks by changing how I interpret failure.

I used to think of failure as lead bricks I'd collect and forever lug around whenever I didn't meet a goal. An infinite burden with no purpose.

Now I think of failure as a heavy work out. Rather than bearing a burden of failure, I fill the experience rips/tears with knowledge protein. It's a semi-silly analogy, but it's really helped me. Knowledge + experience = wisdom.

PS. Adioso is great.

What really resonates when reading your excellent post here is that Marcus Aurelius was really on to something with this brand of stoicism. Reading Meditations is difficult because of the style and just translating from 2000 year old language rather different from English but it seems very relevant to the life of a founder, any leader, or really anyone.

Thanks for sharing Tom. I enjoyed your recent LI post about some of the recent successes you’ve helped create in multiple businesses - it really seemed (with all the social media caveats) that you’ve been focused and continue to create enormous value around you.

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 doing what I need to do to make a living along the way, and doing what I can to keep the ball moving forward towards some fuzzy long-term career outcome and/or life purpose.

And yep, it does all seem to be yielding some solid results, but if it looks like I've been focused, well I think that's a happy accident :)

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.

I guess, as a consultant, for me working on multiple projects or with different businesses is just part of life.

To actually be shipping outcomes: that takes focus.

And I’m glad to hear the ‘source’ project is also progressing strongly.

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.

Thank you for this. It made a whole lot of difference today.

Very interesting that your batch recognized that the emotional strength and stability was the important part, rather than the idea.

I doubt that the whole batch had some sort of collective epiphany that made them consider "emotional stability" a key metric. The way I read the story they voted impressed by variety of seemingly unrelated things that all made them stand out in very pragmatic ways that tomhoward only much later identified as sharing a root cause in emotional stability.

"Who are you willing to continue to become, even after you’ve accomplished some success? What are you willing to risk, to continue going in the direction that is calling you?"

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?

I'd like to reframe this, I think there's only one way to know if someone is a good fit for you - to have a proper, real, deep coaching session. As a software founder I have the idea of a "trial" baked into me, so I think this is no different here. I sometimes coach people for weeks at a time (there's no payment), so that both of us know whether this is right for us (I have the privilege that money is not an issue for me). So that I think is the most powerful, because at that point someone can truthfully commit and go all in and I think for a coaching partnership to be successful, that's the only way in my mind. When someone asks me I often say "let's coach and you can make up your mind after...", this really takes the pressure off, which can otherwise dilute a process that I think is honestly, holy in my book. In other words, if there's a coach you think could be helpful, ask them for a free, full-on coaching session so you can understand if there's a good fit.

And the most effective means to tune in in my experience are simply finding ways to slow down. Pausing, in talking, in walking, being in places that are less crowded. Tuning in during a walk in a park is much easier than in a busy restaurant. And pointing things out that you notice if someone is really charged about something, although that is a delicate process of course. But that's where I'd start.

I really loved your article. In software we are accustomed to constant progress, and we are sometimes on this perpetual hype train. Which creates this stress of the next thing you need to learn, stay ahead of the game, I wonder if in software we should more focus on calm as a counterbalance to hype. A recent HN article I liked for instance focussed on calm apps that instead of constantly bugging you, they quietly do their job.

>> This is a really provocative and powerful post

Agreed, success can be a lonely journey. That's why it's important to have the right kind of support. Courage is not something that comes from within, it comes from the confidence you gain as a result of feeling nurtured and supported by your peers.

It's important to think of success not as a destination, but as a means to a more meaningful end. Because success gives you the necessary tools and momentum to drive even more positive change in the world. As a successful person who has proven the value of their skills, it's your duty to leverage your past successes to maximize the positive impact that you can have in the world through more successful ventures. It's important to not let that raw innate talent go to waste because it is a rare and precious resource for all of humanity.

You must keep pushing forward knowing that your success is directly correlated with the good of society. At times, it may not seem that way, but if you look at historical evidence, there is a strong correlation between wealth inequality and the well being of society as a whole. As a successful person, you are the product and a symbol of a healthy society and your duty is to continue on this never ending journey to inspire others and to drive positive change in the world.

The best way to help the rest of the world succeed is by furthering your own success.

"Be the change that you wish to see in the world" - Mahatma Gandhi

You need to learn to trust the system which allowed you to succeed in the first place and rest assured that others who share this level of trust and commitment will also succeed.

If you're currently struggling to follow your inner voice and you feel like you need some guidance, don't hesitate to get in touch with me via private messages. My fees are reasonable.

I’m confused about how you can give this advice so generally. It seems like you are saying that financial success always indicates a good process and is always a good outcome for society.

At the risk of looking either naive or mean: is this parody?

>What are some of the most effective means for encouraging your conversation partners to start listening and tune in?

Couple therapy? There is an abundance of counselors, and since you're the one doing all the work anyway it will hardly matter they have no startup expertise.

As a coach to similar-level people and professor/coach to elite students at NYU and Columbia Business School, I'm also impressed by how much the social and emotional challenges can be overcome with a few exercises that teach social and emotional skills.

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 read your blog a ton back in the day! Good to see that you're still around. Whenever people start talking about introverts vs extroverts I still think "it's only a model!"

Hey, unrelated to this message but, I think you don't wanna miss this https://news.ycombinator.com/item?id=21941170

And what are those few exercises?

I haven't found writing them in internet forum conveys them effectively. It's like telling people how to play a scale or hit tennis ground strokes. You generally need some demonstration and practice, which most people forego.

I wrote a couple up in my blog with examples and video to illustrate. Since the original post mentioned inner monologue, copying just the action from http://joshuaspodek.com/effective-self-awareness-exercise

1. Carry a notebook or a few sheets of paper for a week or two

2. A few times each day write your exact thoughts — not the general

3. Note the following

- What prompts each instance

- What emotions relate to it

- How the instances relate to each other, what categories they fit in

Each time you write will probably take a few minutes. The whole exercise will take about an hour over a week or two.


Another example is how to make a meaningful connection: http://joshuaspodek.com/meaningful-connection


Each exercise is valuable on its own, but their greatest value comes in building to others, as scales lead to playing musical pieces and ground strokes lead to playing tennis. Practice and rehearsal in any active, social, experiential, emotional, performance-based field leads to self-awareness, self-expression, mastery, and freedom.

The first one sounds similar to a daily mood log ..

Take a peek in the user's profile: https://news.ycombinator.com/user?id=spodek

> perpetual, ever-recurring loop of mental chatter, difficult emotions and body sensations

I find this interesting to read because I don't know what such a loop feels like - "blank" is the most common content of my "mental chatter" and "blank" is the emotion I feel most often - only rarely anything else, mostly just when provoked by emotional music, or during times of high stress.

Edit: I guess the "mental chatter" part is simply because I don't think in words, only impressions or concepts, maybe that is why I don't know this sensation...

There are well-researched emotional intelligence tests that give you a scientific measurement of your abilities (e.g. EQ-i 2.0 model). In fact, they have been personally very helpful to realize that I went through life being unaware of the majority of my own emotional states. I started a game to label how I feel for a few months and that led to some in-depth life changes that I had to make and closed some gaps I had in understanding how others feel.

"Learning to manage your focus, not your time"

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".

One thing I recently learned: Talking about "impact" rather than "importance" makes prioritization easier.


"Importance" pushes you to think about less tangible value judgements, including anxieties that your brain wants to escape from thinking about. "How important is it to write a clear Definition of Done for a junior engineer?" -- "ummm...kinda ...very? (I am a good manager...right?)"

"Impact" pushes you to think about more tangble events, including risks that your brain can concretely imagine their cost. "What is the impact when you write a clear Definition of Done for a junior engineer?" -- "It prevents them from misunderstanding the goal of a task so they're less likely to go down a rabbit hole. It enables them to execute more quickly by strengthening thier brain's 'you're doing the right thing, keep doing' motivation signal. It spends an opportunity to teach them how to identify a clear Definition of Done. It spends some of my time."

Because the cost/benefit of a task's impact is more imaginable, it is easier to decide to spend more resources to do it right or to cleanly abandon the task.

I had the pleasure of working with a brilliant owner of this media company, and what he did was this : he only gave me one task to focus on. Even if I asked if anything more was coming up I was told not to worry about it. He made sure everything worked out right, so truly a manager / leader in spirit. The great thing was it created a peaceful atmosphere in the company. Focus is great, and fully agree with the article.

I remember Keith Rabois describing this to be key to Peter Thiels management philosophy at PayPal:

"So I am going to argue that you need to spend a lot of time focusing on people. This is something I learned from Peter Thiel actually. He used to insist at PayPal that every single person could only do exactly one thing. And we all rebelled, every single person in the company rebelled to this idea. Because it's so unnatural, it's so different than other companies where people wanted to do multiple things, especially as you get more senior, you definitely want to do more things and you feel insulted to be asked to do just one thing." [1]

[1]: https://startupclass.samaltman.com/courses/lec14/

Interesting read! And this is exactly what I learned. On the other end of the spectrum I’ve worked at companies that gave me three jobs, and a manager constantly bugging me, switching goals, scope or priorities (often after a call with a client) . And while I could certainly do it, it wasn’t very pleasant and created a stressful environment.

How meta were those tasks?

This sounds really interesting but I have a hard time imagining the structure of command/task organization. Can you elaborate?

My work was mostly webdev, some front-end and back-end. So I’d get a project to do, and a deadline where applicable. He also really didn’t care how I did it, as long as the work got done. At first there was somewhat more briefing, before he knew my skillset, but as he learned how I worked he just trusted me to do the job. Structure was very flat : quite a few projects worked by one person, and small teams 2-4 depending on the size or scope. When there was a specific skill we didn’t have, that task would be outsourced. In general I guess he was just very good at optimizating for outcome.

It's interesting to read the original post, your comment, and the responses to your comment. There are many different uses of the word "focus" and its relationship with saving time.

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.

Think of your different pursuits and interests as games. Game of your relationship, of making great product or game of making money.

For each of those games you can think about what optimal move is right now. You may not know the truth but you can decide what you think it is.

Now the problem is that if these games are different, then inevitably, by definition you'll come to a point at which given move is great in your game A but sucks in your game B.

And that's The Game. I could write whole lot more about it because I've spend a long time thinking about it, but I think most HN readers can take it from there.

But that's how I see focus. You feel great when you focus on a single game. Then you don't have all those nasty conflicts (which are really the only problem you have in life - not a bad situation - a problem). It's rare though. There are games like social status etc. that you may not even know you're playing.

I would be interested to know more about this, because for me time isn’t the problem, it’s my lack of focus.

During my recent holiday, I took a different approach, and instead of telling myself to work on something from 9am to 12pm. I just woke up naturally and kinda did what I felt doing. Most days this was going to the gym in the morning, and then going to a coffee shop. I probably spend less time working on my project then I usually do, but I managed to complete so much more work, mostly because my time was extremely focussed and I wouldn’t drift off.

Lately I listened to some talks of Jordan Peterson.

There is a lot to say about his work but there is always a recurring theme: take time to think things through.

And I believe in this time of constant distraction it is very hard to do this.

But when you do you order your thoughts and it becomes much easier to communicate your thoughts.

Can you point to a specific text/video of his, that particularly and concisely addresses this point?

Here are some:



He talks mostly about goals in life but I believe the principles are the same.

Search keywords: jordan peterson goals

I find these videos to be what I experienced as typical Jordan Peterson ramblings. A clearly above average affluent, above average intelligence speaker, who goes off with what feels like very little preparation or direction. Does very little for me, specially when it comes to the specific topic of "taking time to think things through" that i was inquiring about (but also anything else, really).

Well in the second movie he explains what happens when you set goals without much thought.

It could be it is not your thing but I believe he has some authority when it comes to psychology.

"He dared to ask what would happen if he were to truly listen and hold space, without jamming the meeting with his ideas on what to do and how to solve things."

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.

Sirrah I'll teach thee a speech. Mark it, nuncle:

  Have more than thou showest,
  Speak less than thou knowest,
  Lend less than thou owest,
  Ride more than thou goest,
  Learn more than thou trowest,
  Set less than thou throwest;
  Leave thy drink and thy whore,
  And keep in-a-door,
  And thou shalt have more
  Than two tens to a score.

You’re a much ‘purer’ coach than I am, in the sense that I provide a lot more business advice and fewer questions [1]. Even so, I wholeheartedly agree with your observation that it is the personal fears and self-work that is most impacting these leaders and their businesses.

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.

Thank you for this write-up. I recently (last ~3 weeks) started working with a coach for the very first time in my career. I think I've been nibbling around the edges of a lot of what you address directly here. What I'm only now starting to have the haziest notion of is how many so-called limitations and struggles might actually be almost total fabrications of the emotional part of my mind. I wish I had been working with a coach a lot earlier in my career.

this is a decent first draft but I feel it would benefit from a major revision that removed the worn cliches

Thanks for writing this, it’s a great end of the year reminder. Enjoyed your focus on sensations! I did a 10 day silent Vipassna retreat and the importance of sensations was such a revealing insight they drilled down on.

Thank goodness the coaching advice comes from a founder that has created legitimate success and isn't just some random author/coach/guru.

I don’t want the struggle anymore. I could handle it when my nervous system was stable, when my ego mind had solidified logical pathways to bypass physical, and likely emotional, pain that had started when I was 4 or 5 years old - the full extent of which was masked, hidden, until my journey towards holistic healing practices lead me to Ayahuasca ceremonies - which dissolved my ego and reintroduced me to the intolerable level of physical injury below. I still haven’t been able to find stable footing, I struggle day to day, even though over the last 3+ years I have successfully healed a significant amount of physical pain with stem cell treatments allowing me to get closer to grounding, still a significant amount of pain remaining preventing me from ever fully grounding, the aversion from pain, unknown how much of the pain I will be able to heal.

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.

It took me a decade of tackling no projects at all to get back on a (different) horse.

Healing takes as long as it takes and you cannot predict the person you will be on the other side.

Interesting. I was surprised there was more talk about the value of communication. It seems to me plenty of friction rests from different forms of comms - professional asw well as personal - gone astray.

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.

Skimming this brought to mind some of the best advice I received as a co-founder: "get over yourself".

This is not the right question.

what a pretentious headline :/

You're being downvoted, but I agree.

I also find it highly convenient that "I operate with an agreement of confidentiality, all of the below is anonymous".

I would imagine odds are decent that several of the "101" he's coached are regular news readers and would pipe up saying how much they benefited from Leo's guidance, yet I don't see any comments as such.

Why wouldn't you get permission from some of your clients to use their name's? Surely out of 101, five percent would agree to be noted.

If you really coached so many CEOs you don't really need to brag about it. This guy is just advertising himself

I'm sure that's where the money is, but I can't really stand being around psychotic people all the freaking time. C-level execs, puke.


Put another way, do you really feel there is nothing you could learn from someone who grew a SaaS business to 20M ARR?

I don't think so. The funny thing is that most people who grew companies to such level of success did so without a coach, but now that the hard part is decidedly over, a coach has become indispensable.

I can’t comment on your last post because it was flagged but I wanted to at least reach out to you with this:

Some of the best coaching I received was from people that may have been deemed less successful, powerful or intelligent than I am but because they took the time to know me and saw my blind spots, they guided me to amazing insights. It was about a connection and relationship. I am forever thankful for their commitment to me. Many of these coaches are selflessly giving to others after having received coaching themselves, so my experience with coaching is different than you seem to imply.

Lastly, I hope you don’t harbor a belief that all success is based on the dark side of human nature; that all CEOs and leaders merely exploit others. That is clearly disproven from so many examples of amazing leaders. Honestly that sounds like a bitter, resentful existence that will make it hard to collaborate with others.

The person to have the idea is not the one ideally fit to execute it, the person to execute the idea is not one ideally fit to run the company. But one can learn. If one was good enough at the previous step there is some wiggle room.

I also hear that people who at one time used a coach of some kind are helped by doing it again.

Possibly because they have a more optimistic and less cynical view of the world than you.

BTW, I also wonder if even the coaches see themselves for what they are. In which case it's disturbing to think that that someone can spend years meditating in an ashram in India and come out still knowing so little about themselves that they don't understand their dark motives.

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