The Exchanges

Q Jerry, you're that person that many speak to today in terms of having that extra person outside of their team to speak to. When did kind of mental health and wellness become so prominent for you?

A Well, it's been a challenge for me all of my life. I grew up in a household where my mother was mentally ill and my father was alcoholic, and so it's kind of hard to pinpoint a time when it became An important issue of mine. I think it became something that I no longer ran away from. First, after a suicide attempt at 18, I entered therapy, and then later again, as I've shared a number of times in my late thirties, when the depression came back. And I would argue that it was only at the time when I was in my thirties that I began to get at the roots of what it was that was behind that phenomena for me, behind the depression.

AI assessment note: “hard to pinpoint a time when it became An important issue of mine.”

Q Jerry, you're that person that many speak to today in terms of having that extra person outside of their team to speak to. When did kind of mental health and wellness become so prominent for you?

A Well, it's been a challenge for me all of my life. I grew up in a household where my mother was mentally ill and my father was alcoholic, and so it's kind of hard to pinpoint a time when it became An important issue of mine. I think it became something that I no longer ran away from. First, after a suicide attempt at 18, I entered therapy, and then later again, as I've shared a number of times in my late thirties, when the depression came back. And I would argue that it was only at the time when I was in my thirties that I began to get at the roots of what it was that was behind that phenomena for me, behind the depression.

AI assessment note: “First, after a suicide attempt at 18, I entered therapy, and then later again”

Q to ask, we, we did speak to Brad earlier. You mentioned Brad, obviously there was the bootcamp and pre-interview. We asked him, what questions would you like to ask Jerry in the interview? And he wanted to ask you two questions in particular. So he wanted, these are from Brad and In around, we're calling Brad's breakout. So, what should VCs be spending more time on today, do you think?

A I think that VCs would benefit from spending more time looking at their own behavior, looking at the ways in which they are complicit in creating the conditions they say they don't want. So, for example, one of the big complaints that VCs get is, uh, give me, is that, uh, entrepreneurs don't trust them, and so they don't tell them everything what's going on. So there's two ways that you can look at that. You can say, okay, what's wrong with the entrepreneur that I've backed? Or what am I doing to make it unsafe for that entrepreneur to tell me the truth, right? Because how do you sit in the seat of being an investor or a director without understanding better the conditions that's going on? So that's one thing. Another thing is to really look at your, your own sources of anxiety, your sources of your own distress, and think about the ways in which you, you're bringing that forward. Be conscious about it. Until you make the unconscious conscious, it will direct your life and you will call it fate. Why do I keep investing in the same kind of entrepreneur? Well, that's a great question. What's happening?

AI assessment note: “spending more time looking at their own behavior”

Q to ask, we, we did speak to Brad earlier. You mentioned Brad, obviously there was the bootcamp and pre-interview. We asked him, what questions would you like to ask Jerry in the interview? And he wanted to ask you two questions in particular. So he wanted, these are from Brad and In around, we're calling Brad's breakout. So, what should VCs be spending more time on today, do you think?

A I think that VCs would benefit from spending more time looking at their own behavior, looking at the ways in which they are complicit in creating the conditions they say they don't want. So, for example, one of the big complaints that VCs get is, uh, give me, is that, uh, entrepreneurs don't trust them, and so they don't tell them everything what's going on. So there's two ways that you can look at that. You can say, okay, what's wrong with the entrepreneur that I've backed? Or what am I doing to make it unsafe for that entrepreneur to tell me the truth, right? Because how do you sit in the seat of being an investor or a director without understanding better the conditions that's going on? So that's one thing. Another thing is to really look at your, your own sources of anxiety, your sources of your own distress, and think about the ways in which you, you're bringing that forward. Be conscious about it. Until you make the unconscious conscious, it will direct your life and you will call it fate. Why do I keep investing in the same kind of entrepreneur? Well, that's a great question. What's happening?

AI assessment note: “VCs would benefit from spending more time looking at their own behavior”

Q Jerry, who coaches the coach? Who coaches you? How does that work when you need coaching?

A To be clear, I have worked with the same psychoanalyst for 24 years, and I often quote her in one form or another, um, and I have never stopped working with her So she's my first coach. I've also had other coaches over the years, but the most important people, um, who work with me in that way are actually my partners here at the firm. One of the things we do is we work with each other. Um, and so a lot of the values, cause remember that whole inner and outer and making sure they map. Well, this is the way we actually run a company and people who come to the bootcamp, see us working with each other. Um, right there, right there in person, right in the moment. So I have a few coaches.

AI assessment note: “I have worked with the same psychoanalyst for 24 years... So she's my first coach.”

Q So then how do you assess, then, when you look at it and look at the venture ecosystem as a landscape today, how do you assess the current crop of VCs in terms of kind of integrating that kind of inner self and then the outer self?

A Well, I'm actually super excited. You know, Brad Feld is our partner in doing the VC version, the investor version of the bootcamps that we've been doing there for a few years, and we have our second coming up in January, and we designed them to have 15 slots, and not only did we sell out, but we actually expanded this one in an experiment, and we're taking it up to, I think, 23 or 24 people, and I just want to pause and recognize that. You've had 15, even though it's very well known that you come and you hang out with Jerry and Brad and the reboot team for a couple of days, and you were going to cry, and you were going to laugh, and you're going to be challenged, just the way Alex Blumberg was, uh, on that, that podcast, and you're going to look in the mirror at your shit, and that camp sold out, because I think people are realizing that the current way of doing things isn't necessary.

AI assessment note: “I think people are realizing that the current way of doing things isn't necessary.”

Q Jerry, who coaches the coach? Who coaches you? How does that work when you need coaching?

A To be clear, I have worked with the same psychoanalyst for 24 years, and I often quote her in one form or another, um, and I have never stopped working with her So she's my first coach. I've also had other coaches over the years, but the most important people, um, who work with me in that way are actually my partners here at the firm. One of the things we do is we work with each other. Um, and so a lot of the values, cause remember that whole inner and outer and making sure they map. Well, this is the way we actually run a company and people who come to the bootcamp, see us working with each other. Um, right there, right there in person, right in the moment. So I have a few coaches.

AI assessment note: “I have worked with the same psychoanalyst for 24 years”

Q Now, I'd love to start today by hearing a little bit about you and how you made your way first into venture and then came to be known as the CEO Whisperer. So what was the journey for you?

A Oh, uh, I haven't told the story of becoming a VC in a while, so that's kind of fun. You have to admit and imagine that my face is getting all, like, watery as I flash back and remember. Way back. I'm in my early twenties, and I'm a technology reporter for a magazine called Information Week. Didn't expect to be a technology reporter. Expected to be a poet and writer. That was life. And I'd spent a As a reporter, then eventually news editor, and then eventually editor of that magazine, and then I became director of editorial technology, which put me directly in the path of trying to figure out what our non-print strategy was to be, and this is probably back when you were in grade school, so it was in 1994.

AI assessment note: “I'm in my early twenties, and I'm a technology reporter for a magazine”

Q but in terms of those earlier years, in terms of kind of the psychological challenges and the alcoholism that you mentioned, I think the hardest thing I find for me with my mother's MS is becoming a carer so much earlier than I thought that I would as a child back when I was. How did you deal with adopting that responsibility so much earlier than you thought you would?

A Well, to answer your question directly, I'll go back to you for a moment and just acknowledge what you just said, because I think that that's incredibly important. At a much earlier age, perhaps, than you were prepared for, you were thrust into a position of being a parent, taking care, being a caregiver. And that's an important statement that you just made, because while it's not the only root cause of mental illnesses, such as depression or anxiety, it can be a contributing factor, because you experienced, and Tracy will recognize this, because of our mutual friend Khalid Halim, my partner likes to call it early promotion. You experience this phenomena being thrust into early onset adulthood when your emotional body may not have been prepared for it. The positive attribute of that is that at a very young age, you experienced grown-up success, if you will. For me, the phenomena was very similar in the sense that each of my siblings and I were responsible for each other and for ourselves. The way it expressed itself for me was that I started stepping out of the household at about age 13 and spending a lot more time out in the world at large. And so we each respond to the pressure of growing up early and being responsible for our parents differently. And it can contribute to the loss of a sense of self as a consequence.

AI assessment note: “I started stepping out of the household at about age 13 and spending a lot”

Q but in terms of those earlier years, in terms of kind of the psychological challenges and the alcoholism that you mentioned, I think the hardest thing I find for me with my mother's MS is becoming a carer so much earlier than I thought that I would as a child back when I was. How did you deal with adopting that responsibility so much earlier than you thought you would?

A Well, to answer your question directly, I'll go back to you for a moment and just acknowledge what you just said, because I think that that's incredibly important. At a much earlier age, perhaps, than you were prepared for, you were thrust into a position of being a parent, taking care, being a caregiver. And that's an important statement that you just made, because while it's not the only root cause of mental illnesses, such as depression or anxiety, it can be a contributing factor, because you experienced, and Tracy will recognize this, because of our mutual friend Khalid Halim, my partner likes to call it early promotion. You experience this phenomena being thrust into early onset adulthood when your emotional body may not have been prepared for it. The positive attribute of that is that at a very young age, you experienced grown-up success, if you will. For me, the phenomena was very similar in the sense that each of my siblings and I were responsible for each other and for ourselves. The way it expressed itself for me was that I started stepping out of the household at about age 13 and spending a lot more time out in the world at large. And so we each respond to the pressure of growing up early and being responsible for our parents differently. And it can contribute to the loss of a sense of self as a consequence.

AI assessment note: “I started stepping out of the household at about age 13”

Q So then how do you assess, then, when you look at it and look at the venture ecosystem as a landscape today, how do you assess the current crop of VCs in terms of kind of integrating that kind of inner self and then the outer self?

A Well, I'm actually super excited. You know, Brad Feld is our partner in doing the VC version, the investor version of the bootcamps that we've been doing there for a few years, and we have our second coming up in January, and we designed them to have 15 slots, and not only did we sell out, but we actually expanded this one in an experiment, and we're taking it up to, I think, 23 or 24 people, and I just want to pause and recognize that. You've had 15, even though it's very well known that you come and you hang out with Jerry and Brad and the reboot team for a couple of days, and you were going to cry, and you were going to laugh, and you're going to be challenged, just the way Alex Blumberg was, uh, on that, that podcast, and you're going to look in the mirror at your shit, and that camp sold out, because I think people are realizing that the current way of doing things isn't necessary.

AI assessment note: “people are realizing that the current way of doing things isn't necessary”

Q Now, I'd love to start today by hearing a little bit about you and how you made your way first into venture and then came to be known as the CEO Whisperer. So what was the journey for you?

A Oh, uh, I haven't told the story of becoming a VC in a while, so that's kind of fun. You have to admit and imagine that my face is getting all, like, watery as I flash back and remember. Way back. I'm in my early twenties, and I'm a technology reporter for a magazine called Information Week. Didn't expect to be a technology reporter. Expected to be a poet and writer. That was life. And I'd spent a As a reporter, then eventually news editor, and then eventually editor of that magazine, and then I became director of editorial technology, which put me directly in the path of trying to figure out what our non-print strategy was to be, and this is probably back when you were in grade school, so it was in 1994.

AI assessment note: “I'm in my early twenties, and I'm a technology reporter for a magazine”