I coached 101 CEOs, founders, VCs and other executives in 2019: These are the biggest takeaways

I went through my calendar recently to count all the clients I worked with in 2019 as part of my coaching practice. The answer: 101 powerful and extraordinary individuals. Wow, I was blown away, I had no idea that it would be this many. The kinds of people I had and continue to have the privilege to coach ranges tremendously in their backgrounds: I’m coaching VCs in and outside the US, CEOs on their 3rd or 4th company, founders that have been through YCombinator, founders with billion$+ valuations, founders that are just starting out, filmmakers, radio hosts, people with other, varied backgrounds. About 60% were men, 40% were women. Some of these people were part of the CEO group coaching programs (I ran 3 this year) and all of the rest were in 1:1 coaching. 

Since most people find me through word of mouth, I haven’t found it important enough to update this website, and frankly, I’m a bit embarrassed about what it looks like today. Instead of fixing the said website, I thought it more helpful to type out some of the biggest takeaways these people have shared with me. I believe it is rare to have access to the inner world of so many brilliant and extraordinary people. And I thought sharing some of the inner workings could be helpful to many. Here we go:

Note: Since I operate with an agreement of confidentiality, all of the below is anonymous and in parts abstracted: 

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

I love this insight a successful CEO told me after one of our sessions. When I ask people what the most difficult thing is about being a founder, CEO, VC or otherwise high-achieving individual, some answers are this: hiring, fund-raising, sales, building the team, etc. What I’ve learned time and again this year especially, is that this is not the case. 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.

As part of my training as a trauma therapist and having spent almost 2 years living in a Buddhist monastery, I employ most of my tools from that time to support people in how to find peace and harmony with what’s presently alive, no matter how difficult it is. And eventually, to even have fun with it. I’d argue that this is 60-70% of my work. All my learnings as an entrepreneur (I co-founded a startup called Buffer) and angel investor come way later and frankly, tend to be much less important than helping folks with their inner workings first.

To that point, people have heard me say that I think it quite reckless and silly for founders and other executives to go through their life and business world (when you can afford it) without a trusted mentor, coach, advisor or therapist. The demands on the psyche of this kind of work can’t be overstated and acknowledging it and meeting it head-on with outside support has been my own best life and business decision. And I’d like to think the same is true for those that I had the privilege to work with.  

I couldn’t agree more with how my friend David Cancel put it in this Tweet: 

Power comes with the ability to receive a “no”

We often tend to think of CEOs, VCs, founders and other successful people as being powerful. Coaching is fascinating because it evolves around the aspects of their lives where they have forgotten or lost access to their own sense of power and agency. Case in point, several founders talk to me about how to improve their relationship with their investors. They’d like some tips and advice on what to say to them and how to communicate. And then, regularly, I point out that this is not about their investors at all, but about how scared they are and how they perceive their own power in that relationship. And sometimes I say that right now, at this moment they are bringing up that question, they are beggars, asking me to help them in how to plead and beg more convincingly. That can be very irritating to hear from me, but that very irritation often also stokes something within them that brings them to an insight to see things differently.

What I’ve learned is that most of our problems occur when we don’t see our own power anymore. When we’ve become small and think we’ve gotten the shorter end of the stick. “Well, but they are the investor, they got the money, I gotta do what they say!” is one version of that. And then we go to work, and dismantle that statement, to see that that is not the case at all. That said investors are humans, with their own fears, insecurities, dreams and losses. And that what they want more than anyone else, is a founder that acts from their power, because that is how they will be most successful too. 

The question I often like to ask then is: What do you have to accept to step back into your power in this moment/relationship? Frequent answer: That the answer might be “no”. That this investor might not give you any more money in the future. That they might be upset or irritated or scared. Once we get to that, once we’ve slowed down enough to embrace that whatever they are attempting, coming from their deepest dreams or wishes may be met with a “no”, things tend to shift. A new freedom often opens up, that a simple “no”, as scary as it was at first, upon closer inspection, isn’t so bad after all. 

“Maybe this isn’t what 1:1s are about. Maybe it’s about really listening…” 

This was from a very successful founder who came to this insight around what it means to be a manager. Most of his entrepreneurial career he was the one pushing the boulder up the hill. And he got incredibly good at it, world-class in fact, I would say. As his organization added more and more layers of management, he became stuck. Then, something clicked and things fell into place. Being a manager wasn’t anymore about pushing the boulder up the hill and carrying others with him. What came to him was the scary and yet powerful idea of leaning back, of making space for his team and others around him. 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. 

As much as we can read about this concept in books, it is something else entirely when it comes as a deep insight from our own direct, inner exploration. When people dare to make this move, of leaning back, especially after they’ve become somewhat successful already,  it tends to come with the deep inner fear that doing so will mean that they will now lose it all. Because they’re no longer leaning forward and doing and that is the posture they have associated with success. It requires a great deal of courage to lean back and I often invite people to experience this physically in their chairs and notice the difference of being forward or rested back on the back of their chairs. And once they do, magic seems to happen. Things don’t fall apart, they don’t lose it all and surprisingly, quite the opposite occurs often: Others have the chance to step up and to create and achieve. That is, what I believe great leaders and managers have learned and can execute on. 

Learning to manage your focus, not your time 

Frequently founders show up to sessions with a plea for help. Their schedule is too full, their calendars are packed, they are overwhelmed. Do I have some advice on how they could manage their time better? My answer is always a version of “no, but I don’t think time is your problem, focus is”. When most of us set out to become entrepreneurs of any kind, it comes with a wish for freedom, for doing what is our deepest inner calling. Yet, soon enough, after a few months or years and even some success, many find themselves in that same trap. Their calendars full, reacting to email after email, bogged down by meetings. Where is that freedom now? 

In moments like that, I like to remind people of something bigger: Why are you here? Why have you started this company in the first place? What are your 3 most important values for doing what you do? When we recalibrate to that, we also place back the sense of power and agency onto ourselves. We can step out of the victim role that we’ve assumed in relation to our company and calendar. And we step back into the role of the powerful individual, often quite literally the CEO of a company that has the ability to shape her life however it is good and right for her. Which of these meetings and calendar events are not serving you? Which of these relationships are not serving you anymore? Which ARE serving you and really underline the focus you want to have for yourself and your company? Coming from that place, they rarely need my help to make the changes required to be on top of their lives instead of it being on top of them. They step into that fear of the unknown, of possibly being met with upset or irritation, but also coming from their own clarity and peace of mind. That is real power. 

Detachment is not non-attachment 

Since Buddhist and Stoic concepts have become quite popular in the tech world and with the CEOs, VCs and founders I coach, there’s an interesting thing that I started to notice in my coaching sessions. As founders become more successful and they hear more demands from team members, customers, the press and so on, some of them come back with the idea that they now need to practice non-attachment from all those things. When I ask them what they mean with that is that they want to somehow find a way to not let these things bother them, to have them fall off of their armoring so they won’t be impacted by it. 

My response here is that that kind of approach is not non-attachment, but rather detachment. Or put more provocatively, a form of numbing. Non-attachment, on the other hand, is a different journey and process. It is about becoming like water, learning to let these emotions come to you, agreeing to them and then letting them leave. Whether it’s fear, anger or hurt, what I started to practice with my clients is to let these things come and as they come, notice how they don’t want to stick around if we really agree to them:

• The sadness wants to become tears and flow and become tender thereafter
• The anger wants to punch, ball hands into fists and then fizzle out through the arms and legs
• The loneliness wants attention, to be held, embraced and just sat with.
• The fear wants to be felt, receive attention and permission to flow through the body, only to leave a trail of energy and aliveness behind.

They just want to be felt, heard, acknowledged and then move on. This often happens very viscerally, with the body trembling or shaking, sometimes tears running down their cheeks. All of that is fine and welcome. That is the idea of us not attaching to our emotions, without however shutting them out or detaching from them. As a byproduct of practicing with that, a lot of founders and executives reported that they have in return been able to listen more deeply and more closely to their team, customers or their friends and family. 

The paradoxical approach to dealing with successful people’s biggest fear

There’s a paradoxical secret of coaching successful people. And a good chunk of the people I coach has been way more successful materially than I ever was as an entrepreneur. That paradoxical secret is, that for them to keep growing, to keep living even more deeply and authentically into what makes them come alive, I invite them to risk what brought them to where they are today. This might sound like a common quote from Instagram, but in reality, this can be brutal and powerful. What this brings up for all people, is the deepest fear most of us carry, which is to lose it all, after we’ve accomplished something. And yet, that is exactly where some of the biggest insights come about after we go there. 

In one session I invited a founder with a million $ company on this journey with the words “Your company has gone bankrupt, I’m sorry. What do you notice?” He described that letting himself go into that brought up a fear so vast that he felt as if he was being swallowed up in a giant brick of concrete. Staying with that, I invited him to notice what it’s like to be fully stuck in it, with all the pain and unpleasantness. Then I asked him what he wanted to do. His answer clear as day: “I want to break out of it.” And so he did, viscerally, arms and fists swinging, in controlled motions breaking out of the cement block. As this passed, he said that it is as if he’s a new person, free to do whatever is right and helps him come alive. The steps he took from there to help his business grow were some of the most inspiring I’d seen to date. 

The question that remains for me after this is: 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?

Life is not an endurance exercise

When I think of the beautiful conversation that this insight and transformation sprang out of, my heart and eyes light up. In the session, we uncovered a belief that life is an exercise in endurance. To be tough and strong, to swim through the rough waters, no matter what waves are being thrown at us. And to keep going, no matter what. 

Most successful people carry a version of that belief with themselves around and I too have for the longest period of this life (and I’m sure some layers of it are still there!). This belief is powerful, it gets many of us to accomplish things that most people only dream of. Yet, there comes a point where that belief has served its time. Where we’ve become so tired and exhausted from all the enduring, that a quiet voice dares to ask: Is that really what it is about? What I like to challenge that belief with is this: What if life is not about endurance? What if it is about love, freedom, doing what’s fun and enjoyable? When I throw that out there, the first reaction is often one of disbelief and irritation. When we go deeper, there then tends to be a period of grieving and tears, of all the hardship and bracing from the time we’ve endured that’s now flowing out of us, making way for a gentler, more loving and at the same time more powerful lens to see the world through. 

Enduring gets us far, but I don’t think that’s what life is for. To let go of that belief and to allow a new one to emerge, often one rooted in love and joy, is scary and takes courage. Especially when endurance has helped you build a massive company or another successful thing. When people still decide to step into that, I’m in awe, I sometimes do dance parties after sessions alone in my apartment, simply to celebrate their lives and insight and willingness to continue to dare becoming more true to who they really want to be. Ask yourself those same questions and even if the reactions are painful within you, see what happens if you keep going with it. 

“I’m realizing it is boundaries that create connection. Now everything has changed.” 

Here was a brilliant founder on his 3rd company, all of them successful, that had yet landed in the “pleasing people trap” for most of his life. He had thought that his job was about being agreeable, listening to everyone coming to his office, and helping people solve their problems. I suggested that he’s not looking at this from the angle that serves him and other people most. I proposed to him that we do one thing only in response to this: We work on his anger and rage and let that come up in his life. From my trauma therapy training I know that when we’re trapped in victim or pleasing mode, it is often because we don’t see our agency in creating healthy boundaries that protect us. And the key to creating those is our anger and healthy aggression. 

Slowly, he started to change how he was available to others and when and he took charge again of his time, his space and ultimately his life. Of course, there was a tremendous fear – now that he was setting up these boundaries and took charge of his life, would people react with rejection? Rejection is no joke, it is our ultimate social fear – to be ostracised from our tribes would surely mean we would die just a couple of thousand years ago. To his surprise, they didn’t, they were grateful that he had become firm and clear on his boundaries and what served him because they too wished for more of that in their lives. This moment of honesty created a whole new connection with his co-founders and team, one that was way deeper before. 

When we allow ourselves to create our boundaries and learn to state them firmly, we are able to live our lives in peace and relaxation. This is because we can now trust into our boundaries to protect us, with a good dose of healthy aggression when we need it. And we can let down our guard for the moments where that isn’t necessary and create deep connection with other humans. 

“For the first time I can feel, it really is about sharpening the ax before chopping down the tree.” 

Most all of us struggle with resting, with really honing our sense of inner emotional resilience. This YC founder had seen and done most of it all when it comes to startup journeys, now working on his 3rd company, but with a family and in a new place. What he’d often bring up was a duality of his life, on the one hand, his startup, and the emotional rollercoaster and on the other his family and private life. How to handle it all? 

What I challenged him to see was that these seemingly opposite aspects of his life, are in fact not opposites, but one and the same. When he was playing with his daughter, spending time away from his computer, he was serving his dream and purpose of building this company deeply. And when he was working on the startup, the same was true for how he modeled and supported his family and friends in working on something of value and meaning to him. The hours he spent recharging, vacationing, coaching, those all as he put it, aren’t just helping him personally, but everything he was touching and wanting to accomplish as a whole. 

There’s an insight into self-care here, that I think is easily overlooked. And that is that self-care and accomplishment are inter-dependent. They are like good friends holding hands and one without the other is a sad story. The center here is also not self-care or accomplishment, but the human being that lives in between. Both are there to serve us on our journey to a fulfilled and meaningful life. Self-care is not a means to work even harder. It is a servant to us in our humanity, in the same way, that our work is. 

Gratitude to all those that danced with me in 2019

If you’re reading this and we’ve worked together in a coaching capacity in 2019, I want to thank you from the bottom of my heart. I’m so grateful for your courage and ability to step into your fears and power and coming into the arena with me. I often don’t get enough time in sessions to go into detail around how you have impacted me. How your ability to show up, to be vulnerable, to be scared, to allow yourself to trust in our connection builds my own trust and confidence to keep doing so day in and day out in my life.

I once sheepishly and guiltily admitted to my own coach that I feel that my clients are among the most inner layers of my community. I was scared she might rebuke me for bringing work and life this close together. Instead, she encouraged me, smiled and cheered me on, saying with her eyes “You understood!”. So I want to share that with you, I don’t take that you’ve come into my life lightly, in fact, quite the opposite. I see it as one of the most meaningful signs of love and openness to allow yourself to be seen by me in the ways that we have together in our sessions. Thanks again and to the many of you I’m continuing to work with in 2020, I’m so excited about what’s to come, even though I have no idea of what that will be exactly, something tells me that it’ll be epic.

Final words

I love coaching, it’s the most fun and exciting thing I’ve ever done in my life. I get to meet people in their deepest confusion, only to see them emerge with their crystal clearest insights and wisdom. To witness that, over and over again, frankly, I would pay THEM money to get to do it. That it’s the other way around is just the cherry on top. I hope some of this is helpful to you on your journey to becoming your own best version of yourself, achieving your dream of being a founder, investor, CEO, executive or otherwise successful individual contributing to life meaningfully. 

If there’s just one thing these incredible people have taught me from the hundreds of sessions this past year, it’s this: Learn to embrace all aspects of your humanity, particularly of your emotions and I guarantee you, if you stick with it, you’ll have everything you ever dreamed of. To me, this is not an empty promise, this is science, clear as day. When we are able to trust, agree and embrace it all, over and over again, we arrive at a place of stillness, with the possibility for powerful action. And that, repeated over time, creates the life we want. 

Thanks for reading,
love, Leo.