11 ms·

Takeaways from coaching CEOs, founders and VCs

533 points by LeonW 7y ago

jonnym1ll3r 7y ago
"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?
- LeonW 7y ago
  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.
  - prox 7y ago
    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.
- cryptica 7y ago
  >> 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.
  - majos 7y ago
    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?
- DenisM 7y ago
  >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.
Roritharr 7y ago
"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".
- prox 7y ago
  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.
  - Roritharr 7y ago
    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?
    - prox 7y ago
      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.
  - Pandabob 7y ago
    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/ https://startupclass.samaltman.com/courses/lec14/
kaushikktiwari 7y ago
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.
cryptica 7y ago
I'm surprised when I hear that big CEOs have success coaches. How can people who became successful through the manipulation and exploitation of humans understand the dark side of human nature so poorly that they don't see these coaches for what they are?
- kristianc 7y ago
  Put another way, do you really feel there is nothing you could learn from someone who grew a SaaS business to 20M ARR?
  - cryptica 7y ago
    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.
    - kingludite 7y ago
      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.
    - digitaltrees 7y ago
      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.
kingludite 7y ago
Thanks for updating the website Leo and yes you should be ashamed of yourself. Ill tell a funny because I cant help myself. My (I would say fruitless if I didn't have so much fun) conversations with money-men always end up in the same pattern. First I explain that if they were entrepreneurs they wouldn't be investing in anyone else. They are going to be wrong as a rule when judging one. Then when I have them unbag the emotional state of "wwwhat???" I explain they are just in the game for the game, they try to make more coins from the many coins they already have because that is all they know about life. I want investing in my business to be as fun for them as retirement since that is what I'm really competing with. Fun as in building a better world with happy people, healthy food, a nice green environment and the crazy profits + world domination as a close second. After this they explain they are not looking to have fun, they just want more money then roll their eyes. (One said my plan was so much fun he'd be dead in 2 years.) I change the topic to some horrible things going on in the world and joke how people only care about money. We could design a better land mine or beam advertisements into peoples heads! Imagine the money to be made! If you are hungry the free market waves a sandwich in front of your nose and goes "I have a sandwich! na na naa na!"
JacobAldridge 7y ago
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.
itronitron 7y ago
this is a decent first draft but I feel it would benefit from a major revision that removed the worn cliches
tomhoward 7y ago
> “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.
chiefalchemist 7y ago
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.
spodek 7y ago
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.
- snawster 7y ago
  > 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...
- dd36 7y ago
  And what are those few exercises?
  - jt2190 7y ago
    Take a peek in the user's profile: https://news.ycombinator.com/user?id=spodek https://news.ycombinator.com/user?id=spodek
throwno 7y ago
This is why diversity is important. If the entire batch of YC founders suffer from White Fragility it's going to reduce the chances of success.
black_13 7y ago
This is not the right question.
xchip 7y ago
what a pretentious headline :/
- canada_dry 7y ago
  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.
  - xchip 7y ago
    If you really coached so many CEOs you don't really need to brag about it. This guy is just advertising himself
JunkDNA 7y ago
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.
F_J_H 7y ago
Skimming this brought to mind some of the best advice I received as a co-founder: "get over yourself".
bryanmgreen 7y ago
Thank goodness the coaching advice comes from a founder that has created legitimate success and isn't just some random author/coach/guru.
loceng 7y ago
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-passed-away-yesterday#disqus_thread 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-today-my-birthday 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.
Zelphyr 7y ago
"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.
- haecceity 7y ago
  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.
turk73 7y ago
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.

533 points by LeonW 7y ago

"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?

LeonW 7y ago
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.
- prox 7y ago
  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.
cryptica 7y ago
>> 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.
- majos 7y ago
  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?
DenisM 7y ago
>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.

Roritharr 7y ago

"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".

prox 7y ago
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.
- Roritharr 7y ago
  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?
  - prox 7y ago
    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.
- Pandabob 7y ago
  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/ https://startupclass.samaltman.com/courses/lec14/

kaushikktiwari 7y ago

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.

cryptica 7y ago

I'm surprised when I hear that big CEOs have success coaches. How can people who became successful through the manipulation and exploitation of humans understand the dark side of human nature so poorly that they don't see these coaches for what they are?

kristianc 7y ago
Put another way, do you really feel there is nothing you could learn from someone who grew a SaaS business to 20M ARR?
- cryptica 7y ago
  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.
  - kingludite 7y ago
    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.
  - digitaltrees 7y ago
    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.

kingludite 7y ago

Thanks for updating the website Leo and yes you should be ashamed of yourself. Ill tell a funny because I cant help myself. My (I would say fruitless if I didn't have so much fun) conversations with money-men always end up in the same pattern. First I explain that if they were entrepreneurs they wouldn't be investing in anyone else. They are going to be wrong as a rule when judging one. Then when I have them unbag the emotional state of "wwwhat???" I explain they are just in the game for the game, they try to make more coins from the many coins they already have because that is all they know about life. I want investing in my business to be as fun for them as retirement since that is what I'm really competing with. Fun as in building a better world with happy people, healthy food, a nice green environment and the crazy profits + world domination as a close second. After this they explain they are not looking to have fun, they just want more money then roll their eyes. (One said my plan was so much fun he'd be dead in 2 years.) I change the topic to some horrible things going on in the world and joke how people only care about money. We could design a better land mine or beam advertisements into peoples heads! Imagine the money to be made! If you are hungry the free market waves a sandwich in front of your nose and goes "I have a sandwich! na na naa na!"

JacobAldridge 7y ago

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.

itronitron 7y ago

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

tomhoward 7y ago

> “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.

chiefalchemist 7y ago

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.

spodek 7y ago

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.

snawster 7y ago
> 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...
dd36 7y ago
And what are those few exercises?
- jt2190 7y ago
  Take a peek in the user's profile: https://news.ycombinator.com/user?id=spodek https://news.ycombinator.com/user?id=spodek

throwno 7y ago

This is why diversity is important. If the entire batch of YC founders suffer from White Fragility it's going to reduce the chances of success.

black_13 7y ago

This is not the right question.

xchip 7y ago

what a pretentious headline :/

canada_dry 7y ago
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.
- xchip 7y ago
  If you really coached so many CEOs you don't really need to brag about it. This guy is just advertising himself

JunkDNA 7y ago

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.

F_J_H 7y ago

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

bryanmgreen 7y ago

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

loceng 7y ago

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-passed-away-yesterday#disqus_thread 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-today-my-birthday 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.

Zelphyr 7y ago

"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.

haecceity 7y ago
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.

turk73 7y ago

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.