Understanding mental health in Silicon Valley, with professional coach and former investor Jerry Colonna

Extra Crunch offers members the opportunity to tune into conference calls led and moderated by the TechCrunch writers you read every day. TechCrunch’s Connie Loizos recently sat down with VC-turned-professional coach Jerry Colonna for a chat about founder mental health, his less than predictable career path and his new book Reboot: Leadership and the Art of Growing Up.

After years as a successful venture investor, Colonna found himself confronting his own personal struggles with mental health. As a result, Colonna shifted his focus towards coaching founders and executives through the tensions that exist between personal happiness, mental health and traditional leadership practices.

In his book and in his conversation with Connie, Jerry discusses how one’s previously developed standards of success can impact their ability to lead and realize fulfillment from their work. Jerry elaborates on why many Valley executives encounter mental health pressures as their careers evolve, and details advice he gives to his own clients to help them re-engage with themselves.

“First, to unpack that ambition itself, is not a negative. It’s just ambition. But when we don’t understand the context of that ambition, what is it that’s driving us forward? Is it fear? Or is it excitement and enthusiasm about what’s possible?

Generally, it’s about both, right? When our ambition is primarily unconsciously driven be our fear, the likelihood is high that we’re going to drive the people who work for us crazy. Because nothing that they do, is ever going to make the fear go away. No matter how successful our ambition makes us.

Because the underlying motivation is fear. I am looking to become safe by what I’m driving towards. Now, if we were to flip it and say the thing that is really driving the ambition, is dreaming of a world that is possible. “I can’t imagine how cool it would be if this company were X.” Well, I may still act in a way that’s driven, but I don’t necessarily have to drive the people around me crazy.

And so by understanding the complicated nature of that word ambition, we get to, as I say, dial up the positive aspect of it and release a little bit from the less healthy more negative aspects of it.”

Jerry and Connie dive deeper into how media coverage impacts founder psyches and how it has evolved amidst an increased awareness around mental health. The two also discuss how external pressures are changing for younger generations of founders, as well as how society as a whole can truly tackle widespread mental health issues.

For access to the full transcription and the call audio, and for the opportunity to participate in future conference calls, become a member of Extra Crunch. Learn more and try it for free. 

Connie Loizos: Jerry, it’s a pleasure to be talking to you. We’ve been talking for many, many years. I’m afraid to say how many years…

Jerry Colonna: It’ll reveal how old we are.

Loizos: I know exactly. But I do remember you starting Flatiron, with Fred Wilson, many, many years ago and then going on to JP Morgan and I know that many of the listeners on the phone right now probably have traced your story because you are one of those characters of great interest in Silicon Valley. Can you talk a little bit about how you decided to leave venture capital and become a full-time coach?

Image via Getty Images / sorbetto

Colonna: Well you have to read my book. No, just kidding.

Loizos: I have read much of it, it’s great.

Colonna: I’m teasing. The short answer to that question is that somewhere in my mid-thirties I began to develop a deep and profound depression that led to the realization that I was not living the life that I wanted.

Loizos: And it’s interesting because I have heard you say that this sometimes happens in your thirties specifically, which I want to get to, but let’s start a little bit with the book itself which I think probably again, some of the people on the line have read. If you haven’t, I can’t recommend it highly enough. It’s a very personal story and so it’s less tactical, but it felt very moving and inspirational.

You start out by laying out your childhood. Your father drank too much, your mother suffered from mental illness. They had seven children which was, you say, “more than they could afford financially as well as emotionally.”

Give us background by way of explaining why you came to see money as the one true thing that could provide some safety from the chaos. And that’s partly because your grandparents made you feel safe and they had some money. Can you walk us through those formative years a little bit?

Colonna: Sure. I think you did a great job summarizing a lot of it… I had an anguished childhood. And it did give me a perspective on money, where I saw not just money as a place of safety, but I saw my grandparents’ house as a place of safety and security.

And I associate that safety and security with the wellbeing that my grandfather could provide, and so it became the pursuit for success in business, really became in effect the pursuit for the same kind of safety and security that I felt growing up at my grandparent’s house.

Loizos: And so you were this very smart child, and you in fact got a scholarship at some point when your parents could no longer afford your tuition, is that correct?

Colonna: Yeah, but to clarify, my parents didn’t pay the tuition — I was paying tuition in college. And you’re referring to the fact that I couldn’t pay for it anymore. But yes, go ahead.

Loizos: Okay. Great. Well how did that scholarship come about?

Colonna: Well, I walked into my advisor’s office. I was going to Queens College, and at the time tuition was $750 per semester. If anybody’s paid tuition lately, they know that it’s not $750 a semester. And I couldn’t afford that.

I was weeks behind on the bill. The bursar kept mailing me letters, because fortunately they didn’t have email at the time or text messaging. And I broke down in tears in my advisor’s office and I said, “I can’t afford to continue.”

And he said, “not on my watch”. And it turned out that he was the sole judge in a program that was awarding a scholarship that would pay the tuition of the recipient. And he said, “I’m giving this to you”, and with it came a summer job at a magazine called InformationWeek, which is still around in some form or another. And within a matter of months, I found myself as an intern at a journalistic enterprise, making trouble.

Loizos: And what did you want to do after you graduated?

Colonna: I thought I was going to be a poet. And I thought I was going to be an English professor. I did not think I was going to be a journalist, although in my heart of hearts, I did want to travel the world, live out of a backpack, and so I did have this belief that maybe in some life, I could be a photojournalist.

That’s what I was thinking I would be. Fly into war zones, and take pictures, and that sort of thing. It’s all very adventurous. But instead, I became a technology journalist, which is not what I anticipated when I was in college.

Loizos: Yeah I can say the same. But still, I just wonder at what point did you realize — I think you say in the book, you thought about being a poet, you thought about being an academic, but you sort of recognize at some point that you wouldn’t be valued by some people in the same way as if you were in job where you made money. Is that fair?

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Colonna: Yeah, I realized that I was attracted to the external approbation. I was attracted to the external validation early on. And it started to make me feel better about myself. It made me feel that, “Hey, maybe I’m on to something.”

I winced even still though when you said I was a smart kid. I suppose I was, looking backwards now, and I look at the rise — I went from being an intern to editor of the magazine in three years. I guess that was a fast rise. At the time it just seemed, “Okay this is interesting, let me try this”, “Oh, okay, let me do this”. 

Loizos: So you went from being a technology journalist to actually investing in tech companies and you were very good at it.

Colonna: I was good at it. I was always attracted to the, first and foremost, “wouldn’t it be cool if this existed” phenomena. You get an entrepreneur walks into your office with a business plan, or as in many cases, a business plan comes in over the transom, and you start reading it and you say, “This would be really interesting if this thing existed in the world, let me see who this person is”, and then you meet the person and you say, “Hmm, this is a really interesting person, I would love to hang out with them.”

And those were my early criteria in investing in people like Seth Godin, at Yoyodyne, which was his first company. Or David Bohnett at Geocities, or Steve Kane at Gamesville. It was, “This is an interesting product, service, idea, who is the character behind this. Wow, that character is a really interesting person. Let’s go have some fun together.”

Loizos: That’s great. And frankly, I think that’s why a lot of journalists love covering these same people, because they’re so interesting. At what point did you decide that it wasn’t satisfying? You sort of tie this to the terrorist attacks of September 11th.

Colonna: Yeah. So, somewhere around late-1999, there was this bubble atmosphere to the web 1.0 experience. Where, sh**.com was making money, and all of the sudden you started to feel that there was a lack of substance to what we were doing, and what began as, “wouldn’t it be cool if this thing existed,” became taken over by what felt like grifters at the time. And that was the first inkling that somewhere inside things were shifting for me.

2000 rolls in, the markets start behaving really, really wonky, but there’s still this big, big push to get companies public and it was just like the year of the grifters. Markets start to collapse, it started to become awful.

Spring 2001 happened, the collapse in the market starts to happen deeper, and deeper. And then finally, one of the companies was an investor in, the Industry Standard Magazine, suddenly went bankrupt. It was an awful summer.

I then went to the Grand Canyon for two weeks and kind of disappeared. And came out convinced that I was going to go ahead and leave Flatiron and join JP Morgan, one of our backers, and just as I was making that decision, the 9/11 attacks hit.

And that knocked me on my ass. It just really rattled me. It scared me. It made me obsessed about whether or not my family was going to be safe, and it made me feel personally connected to the people who died. Because it felt like my city was under attack.

And looking backwards now, I see that I was particularly vulnerable, because the structures of my life were starting to fall apart, as is often the case in the thirties. And I was moving into midlife, didn’t realize it at the time, then February 2002, I hit a second rock bottom in my life where the depression was so bad that I was suicidal, and I had to make a choice.

And I made a choice to live, which meant also making the choice to leave the venture capital business.

Loizos: Had you been seeking therapy before this time?

Colonna: Oh, sure. I had had a life-long relationship with depression, or as I often say, a life long friendship with depression. So, I had been in and out of therapy in my twenties and starting around 1993, I went back into therapy with the same psychoanalyst by Spring of 2002. Exact, P.S. spoiler alert, I continued to see that therapist, Dr. Sayers, really until she died two years ago. She was still working with clients until she was 93.

Loizos: That’s amazing, and I’m sorry for your loss, but it’s obvious that you yourself are a very good therapist, so I was wondering when you started learning some of the skills that you’ve developed over time.

So, Jerry, you did the self-exploration, with the help of the therapist, and then you decide that you’ve got to reach out and help other people that are going through similar challenges. How did you create a business out of that?

Colonna: Well, I did. And I created the business slowly. It was really in response to one young man who came into my office really lost. Telling himself that he was there to network his way to a job in the startup community.

And I asked him a series of questions that had him reveal that he had become a lawyer to please his father. And he then started to cry, and when that happened I said, “Okay, you are doing something different right now. What are you doing?”. And it was that moment that led me to seek out training as a coach.

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Image via Getty Images / Feodora Chiosea

The minute I began training, people started coming to me, and over the course of about a year, I designed a solo practice that had me, maybe, seeing clients two days a week. And in the meantime, I continued to serve on a bunch of boards of directors and do my own work.

And slowly, slowly over time, I built up a solo practice. Which felt perfectly sufficient at the time, but eventually, starting about six years ago, I realized that it wasn’t going far enough, it wasn’t where I wanted it to be.

Loizos: And that you needed to scale it up?

Colonna: Yeah, I needed to address the fact that… most successful coaches will launch a coach training program and train other coaches to be like them. That really wasn’t interesting to me.

I was much more interested in finding a way to get more people to have the benefit of what it was that I and a bunch of other folks are doing. And that’s how we ended up designing the company that is now Reboot.

We began with these immersive multi-day experiences called “boot camps”. And then ended up with a company. Literally five years ago this week.

Loizos: Oh, congratulations. I think what you’re doing is so interesting but it does seem like it requires some external help. Going back to that first client, do you think most executives are trying to impress their parents ultimately?

Colonna: I think that most of us are in an interesting dialogue with the belief systems we developed as children. And I think most leaders are shaped, consciously or not, by those early belief systems. So for example, if you believe that the world is a dog eat dog world, where everybody is out to get their own, then you’re going to build unconsciously an organization filled with people that are self-optimizers.

Then you’re going to call a coach and say, jeez, why isn’t anybody trusting each other? It’s like, well, you’ve unconsciously built an organization that is built around this notion of fiefdoms, right. Because you’re reiterating the belief structure of your life.

Now for a lot of folks, one of the most important forces in any child’s life are their parents. And they shape, positively and negatively, our whole world view.

Because they give us a sense of love, safety and belonging. They give us our sense of worthiness as human beings.

And that’s why I find it fascinating when I’m doing leadership development and leadership coaching work, to really understand the early structures of a person’s life. Not so we can spend the entire time therapeutically going through it, but so we can have a context for the things they may be struggling with right now.

Loizos: Right, right. It’s fascinating. Well, going back to the thirties, you said sometimes managers realize that the coping skills that they developed as children and that enabled them to succeed, become impediments right around then. Is that because they are becoming parents, you mentioned for yourself it was facing middle-age suddenly. I’m just wondering, why do you think these coping skills become problematic at that age?

Colonna: Well, all of our structures, all of the coping systems that we develop as children have a positive and a negative attribute. What happens, though, is that as we age, the systems which were designed to keep us safe, so yay to those systems – they did exactly what we wanted them to do which was make us feel safe – they start to run out of steam because we become adults.

A perfect expression of this might be somewhere in our thirties we might enter into what could be the first major life relationship or love relationship of our life. And so, all of our belief systems about what does it mean to be in relationships start to get tested in a deep and profound way.

And all of the sudden, that person whom we thought we were going to spend our life with, we’ve been living with or being in a relationship with for five to six years, we’ll look across the table and say, “You’re not who I thought you were,” because they are their own person. So their systems start to collapse.

Same thing happens with our careers. All of the sudden we’re in our thirties and we find ourselves living a job, being in a job, and we go back saying, “What happened to that kid in college who said he was going to write poetry for his life?”

Well what happens is that he was successful. He became a reporter. And then he became an editor. And then he became a manager. And then he became a venture capitalist. Well, wait a minute. What about that guy? What happened to that guy?

Loizos: I wonder if you found that also those learnings, you have to reassess when you have your own children. So you’re sort of weighing the values of them and wondering if you may encourage your kids to move in a different direction.

You also talk about ambition being multi-faceted. And you encourage leaders to dial up the better parts of it and dial back the negative aspects of it. Which sounds fascinating but complicated. Can you explain what you mean?

Colonna: First, to unpack that ambition itself, is not a negative. It’s just ambition. But when we don’t understand the context of that ambition, what is it that’s driving us forward? Is it fear? Or is it excitement and enthusiasm about what’s possible?

Generally, it’s about both, right? When our ambition is primarily unconsciously driven by our fear, the likelihood is high that we’re going to drive the people who work for us crazy. Because nothing that they do, is ever going to make the fear go away. No matter how successful our ambition makes us. Because the underlying motivation is fear. I am looking to become safe by what I’m driving towards.

Now, if we were to flip it and say the thing that is really driving the ambition, is dreaming of a world that is possible. “I can’t imagine how cool it would be if this company were X.” Well, I may still act in a way that’s driven, but I don’t necessarily have to drive the people around me crazy.

And so by understanding the complicated nature of that word ambition, we get to, as I say, dial up the positive aspect of it and release a little bit from the less healthy more negative aspects of it.

Image via Getty Images / Ja_inter

Loizos: After this next question, I want to give some of the listeners a chance to ask some questions.

So you say what enables you to succeed may also make you a poor manager. Again, I know it’s sort of a broad question, but can you maybe, give us an example of what you mean there?

Colonna: Sure. One of the most complicated challenges of any leader, is what I would refer to as conflict avoidance. If I grew up in a household with a lot of yelling and a lot violence, I may have successfully developed strategies to quote, keep the peace.

Which then became a very foundational component of the way in which on the playground, in high school, and in college people gravitated towards my leadership. Because I was very good at figuring out what everybody needed. Because I was afraid of conflict.

Now fast forward to a larger organization and start thinking about challenges like, how do we innovate? How do we make choices? Someone’s always going to lose out when organizations have to make choices. I have an agenda, you have an agenda. Your agenda wins. All right.

If we have an organizational technical debt, for example, of conflict avoidance, then what you end up with is lots of people going along to get along, but the best ideas don’t necessarily surface, because the organization hasn’t learned how to deal in a healthy way with conflict.

Loizos: Right.

Colonna: Because we’re avoiding it at all costs. So this is an example of how it’s very successful initially, but it starts to run out of steam. And starts to become a problem internally. Surfacing that, and maybe even loving it and laughing about it, and saying “Okay, here we are, uh oh. Are you okay? We’re going to have some conflict right now.” We make a joke, make it a little easier.

Caller Question: Hey this is Garry. Thank you so much for joining us, really looking forward to the book. I had a question, are you noticing any difference in the leadership culture between, let’s call it the millennial, or gen-Z generation from some of the younger entrepreneurs. Is there any difference in how they lead their companies?

Colonna: I think that one of the challenges of being in that generation, and I think of my children who are 29, 26, and 21, so they’re in that space, I think one of the challenges of that generation is that the propensity which we all have for constant comparison to our peers, is intense.

It’s one of the unintended consequences of social media. And I think that where that shows up in that generation of leaders, I think of a client, for example, who successfully raised $3 million for their start-up at 19. And seven years later is bemoaning the fact that the company only generates $30 million in revenue. 

And he’s surrounded by other CEOs who have had unicorn sized exits. Now, if we could just remove all of that constant comparison and just say, okay, after seven years you’ve developed a profitable business that does good work in the world and generates $30 million dollars a year in revenue. Can you just enjoy that experience? And the answer is no. And I think that of that generation, that constant comparison is worse than I see in any other segment of leadership.

Loizos: You know, Jerry, to that point and question, do you think you can be a good leader without some serious challenges as a child? And I ask this because there are widespread concerns that parents are doing too much to coddle their children, now.

I remember talking to the author of “How to Raise an Adult” who said over the course of 15 years she just saw children that were sort of a chronological age, but emotionally not growing. Incapable of negotiating relationships with their teachers with their roommates. I was just wondering if you were seeing any of that. And again, whether the lack of challenges, can hamper their leadership skills.

Colonna: The question is can you be a good leader without having had adverse childhood experiences. Which is an official term “A-C-E”. And the answer is, yes, of course. I think the larger question that your touching upon, is can you move into adulthood in a way where you are not necessarily working with the wounds of becoming human. And I think that the answer to that question is no.

Meaning that the definition of adulthood that I carry isn’t chronological. And it isn’t what a lot of folks refer to in their twenties as adulting. Do I know how to pay my car insurance on time? That’s an adulting skill. But, the fully actualized adult needs to as Carl Jung said, “Not only walk with God, but wrestle with the devil.”

And the truth is, I think it’s really, really hard to be born a human, without experiencing some sort of existential wound. Clearly some wounds are more intense than others, but we all experience some kind of wounding.

Loizos: Sure, and it’s still hard to know from the outside looking in, what those are. I mean, somebody would have looked at your career, for example, as the successful venture capitalist and probably never would have imagined that you were feeling such depths of despair.

Jerry, before we go, you know a lot of what you talk about is radical self-inquiry — looking within one’s self to ask, for example, “What am I really afraid of?” Which sounds great. But it also sounds like a challenge to people who may not be accustomed to thinking very deeply about themselves.

Do they need to have outside help with this process? And if not, are there any sort of tips and tricks that you could offer listeners right now to do better self-examinations?

Colonna: It is hard. But it may make it easier if you think about it as a practice. That’s something that you just consider every day. And that’s why one of my most famous questions I ask people is, “How are you?”

And I fight that as a radical self-inquiry question because I think it’s very, very rare for us to wake up, settle over ourselves at breakfast, pause, that is don’t look at your phone, and sit there and say, “How am I doing? I’m tired. It’s been a long week.”

And when I use the term radical, it’s somewhat tongue in cheek because what makes it radical is how rare we actually pause and ask ourselves questions like, “How am I? Am I enjoying my life? What’s getting in the way of that enjoyment if I am not enjoying my life? What would I change?”

It doesn’t have to be, in what way was I wounded as a child, it could just simply be a simple little pause that says, “What kind of leader would I like to be? If people left my company, what would I like them to say about their time working with me?”

Isn’t that an interesting question? And you don’t need a professional and you don’t need a coach to answer that for yourself. You just need to take the time.

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Image via Getty Images / vasabii

Loizos: Right. I think that’s such great advice. I mean, people are so strategic about their companies, but they’re not really strategic about themselves.

Caller Question: Jerry, a question for you, what’s the most effective approach to improving a leader’s capability? How do you transition from, maybe you’re not a bad leader, but you’re just sort of mediocre. How do you turn into a great leader over time?

Colonna: Great question. I think that the first step is to be honest to yourself about where you’re struggling. 90% of my work is getting clients to cut through the self-delusion and the pretending. I often start with can we stop pretending that we’re all crushing it all the time? Because we’re not.

So that’s step one. Step two is to actually surround yourself with, not necessarily coaches or therapists or consultants or anything, just some peers. John Donne, the poet, in his blessing for a leader says, “May you be surrounded by good friends who mirror your blind spots.”

So, have you ever considered a 360-degree performance review? Why don’t you ask the people with whom you work, what are your strengths and weaknesses and what could you do better? And that takes bravery.

And then, the most important part of that, is to develop what I would call a personal professional development plan. These are the things I’m going to work towards. These are the things and skills and characterological structures I’m going to work towards. And I’m going to surround myself with accountability buddies.

People who help me. Who say, “Hey you know, you made this commitment to growing in this way, and I see that you’re back to doing that thing. Is that what you want to do? Because it’s going to result in the same place you were in a year ago.” And that kind of honest forthright feedback is essential to that growth.

Lastly, what I would say is do not compare yourself to the projected ideals of all these great leaders. As I like to joke, you are not Steve Jobs, you never will be Steve Jobs, stop looking at Steve Jobs, look at the work that’s in front of you. Take from Steve Jobs, and Bill Gates, and Larry Ellison, take from them the things that are worth taking, but jettison that which is not you. And then lead from that place.

Loizos: I feel, again having been in the industry for quite a while, there was no talk of depression on the part of founders until maybe a handful of years ago it started to become slightly more public and that’s grown. Do you think that the industry has come far enough on that front?

Because obviously, starting a company, being an executive, is hugely stressful, so much more so than people realize at the outset, since you know, entrepreneurship has been so glorified in the media. I’m just wondering how you would rank the industry on a scale of one to ten in terms of our handling of this issue?

Colonna: I think the industry has allowed itself to speak about things. Elders such as myself or Brad Feld who have been very open about our struggles, I hope, have made it easier for those who struggle to come forward. Normalizing the human experience is key to destigmatizing and that destigmatization allows people to get help. I think that that is happening.

But I think you can’t look at the question of the industry without looking at the question of the society as a whole. And the society as a whole still struggles with trying to come to grips with the fact that we struggle as a species. And we somehow see the fact that somebody might be struggling emotionally as evidence of their brokenness or weakness.

And nothing makes me more furious. Because as long as we hold that point of view, as long as we socialize our children to hold that point of view, then we’ll have the statistic, which is I believe, suicide is the number one cause of death in men 35 – 60 years old.

As long as we stigmatize this and we do this bullshit approach where people are expected to be perfect and feel perfect all the time, then people are going to die. And that makes me angry. If you want to know what motivates me, you just hit it.

Loizos: Well, I think that as a business reporter, I could do a better job, I know my colleagues could do a better job, and the industry could do a better job at shedding light on this as well.

Jerry, such a privilege to talk to you. Thank you so much for making the time for us. The book if you don’t have it is “Reboot: Leadership and the Art of Growing Up”. Jerry, thank you so much again. And thank you for being Extra Crunch members, we really appreciate it.

Colonna: Yes, and Connie, thank you for doing this. It was really a delight. And thank you, to all the listeners, it was a different way to have this dialogue and I really appreciated it.

Loizos: Oh, great. Thanks Jerry. Take care, and I hope to talk to you soon.

Colonna: Take care. Bye.

Loizos: Bye.