Deep Dive with Jerry Colonna
INTRODUCTION: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.
Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend, Jerry Colonna. Jerry is the founder of Reboot. Reboot, if you don't know it, is one of the premier, if not the premier leadership consulting and coaching firms in the world. Jerry has had a great career spanning publishing, venture capital, and coaching, which we'll talk about a little bit more here today. And Jerry's also the author of a book called Reboot, like his firm, and the forthcoming book, Reunion, which we'll also talk about today. So, Jerry, thank you for joining me.
Jerry Colonna: Thanks. Thanks. And thanks for that introduction. And I like the fact that you leave out that I was once an investor in your last company. Okay.
Matt Blumberg: Okay. Well, I said you were a top investor.
Jerry Colonna: Yeah. I was a good investor.
Matt Blumberg: So, of course, you would invest in top companies. And we'll get to Reunion, the new book, we'll get to coaching, but I'd love to start a little bit about with your professional career. And I actually should know this, but did you do something before CMP? Were you a reporter?
Jerry Colonna: Yeah, I was a assistant manager in a bookstore and I was a locker repair guy, that's a whole nother story. But no, I started working for CMP when I was a junior in college.
Matt Blumberg: Okay. This is a silly question, is CMP around anymore?
Jerry Colonna: Yeah. Through a bunch of different acquisitions some of the original publications are still operating, but I forget which company actually owns it now. It might be United Business Media, UBM.
Matt Blumberg: Right. I'm trying to even think how to put that in context for people who are newer in their careers and have never heard of it. It's like TechCrunch of 25 years ago.
Jerry Colonna: Yeah. Well, maybe longer.
Matt Blumberg: 30 years ago.
Jerry Colonna: Yeah. Yeah. I mean, we were a technology publishing company. Our competitors at the time were IDG, which is still doing well. Ziff- Davis
Jerry Colonna: And we all published this printed magazine thing that would come out every week. And I was part of the team that oversaw the transition to electronic publishing. We actually had a business unit that I headed up called the Electronic Media Unit. That's how odd it was.
Matt Blumberg: That's suitably 1990s.
Jerry Colonna: Yes. Yes. 1994. Before many people who are listening to this were even born.
Matt Blumberg: And you ended up as publisher just of electronic or overall of-
Jerry Colonna: No, I was the editor. So, I was never on the publishing side.
Matt Blumberg: Oh, okay.
Jerry Colonna: So, I didn't do sales.
Matt Blumberg: Okay.
Jerry Colonna: But I was the editor of a magazine called Information Week, where I'd started as an intern. My former boss, Michael Leeds, used to joke that I started in the daycare center, because that's how young I was, and I became the editor of the magazine at a relatively young age, 24 years old.
Matt Blumberg: And that's very young to be editing anything.
Jerry Colonna: Yeah. I was not just editing, I had a staff of about 40, most of whom were significantly older than me. So, I learned a lot about, " How do you do that?" And then eventually-
Matt Blumberg: How do you do that? That's a good question.
Jerry Colonna: Carefully.
Matt Blumberg: Well, look, we advise, and I'm sure you advise founders all the time, " You should be hiring people better than you. You should be hiring people more experienced than you." So, how did you do that your first time around the block?
Jerry Colonna: I think the benefit that I had... Well, first of all, I had a boss who was older, Leighton McCartney, who's a wonderful person, and then Becky Barnett before that, who then became the publisher. So, I wasn't the ultimate boss in that way, but I think the thing that I had, that I gave, was a vision for what the magazine could be. And I did a lot of dry erase board talks about what the magazine could be. And in building and working with the staff, the goal was actually to put that together, to make that happen. And I was a good editor, but I definitely relied upon those with more experience than I had, to actually do the leadership management, the leadership piece of the business, of the job.
Matt Blumberg: Right. So, you're the editor of Information Week at the dawn of the internet and middle of the computing revolution. It sort of makes sense that you would move into venture capital, because why not?
Jerry Colonna: Well, there was an interim step between. So, I left that position, stayed with the company, and then headed up our efforts to figure out publishing on this weird new medium called the web.
Matt Blumberg: Right.
Jerry Colonna: And so, it was actually that experience that was most relevant to being a venture capitalist.
Matt Blumberg: Right, because presumably that experience you're meeting all the tech founders that are building the publishing infrastructure on the web.
Jerry Colonna: Yeah. Well, this is even before there was such a thing as publishing infrastructure. We were only the third entity to ever sell advertising on a website. That's how early it was.
Matt Blumberg: Right.
Jerry Colonna: And so, I think what led the folks who recruited me to join a newly forming venture capital firm, what they saw in me was someone who had a vision for how advertising supported media was going to be delivered through this medium, and that, what was the potential for this medium to become? So, one of my earliest investments was a company called Lycos, which was arguably the first ad- supported search engine out there.
Matt Blumberg: Yeah. God, Lycos. Do you remember the search engine wars when inaudible.
Jerry Colonna: Mm-hmm.
Matt Blumberg: There were four or five, six different search engines, probably none of which exist anymore. Only Yahoo. Yeah.
Jerry Colonna: Yeah. Yeah. Yahoo.
Matt Blumberg: So, you move. You start Flatiron Partners.
Jerry Colonna: Well, there was a venture firm before that.
Matt Blumberg: Oh, there was a firm before that? Okay.
Jerry Colonna: Yeah. Called @ Ventures. And that's where I went from CMP to CMGI, which was no relationship, but was a direct marketing firm that had invested a lot in building internet companies, and they launched a venture firm. That's where I was recruited. And then, I went from CMGI @ Ventures, which was our venture unit, to joining Fred Wilson to form Flatiron Partners. And that happened in 1996.
Matt Blumberg: In'96. Okay. And so, Flatiron had a five- year run. It was certainly the premier early- stage tech investor in New York, or internet investor in New York and probably one of the top ones anywhere in the world. When you reflect back on those five years, which were crazy, right, those were crazy, crazy years-
Jerry Colonna: Totally crazy.
Matt Blumberg: ...what are some of the big learnings you had in those years?
Jerry Colonna: Well, I mean, there are a lot. I mean, I learned a lot about myself. I learned a lot about the venture business. I learned at the side of probably one of the smartest guys in the business, Fred. I learned the value of building teams and how to do that. So, in some ways it prepared me for coaching. But I think that among the many experiences was to live through a boom and bust cycle, because we went from everything we touched went to gold, to everything we touched went to shit. The other thing that happened during that period was I developed some of the most important relationships of my life. My friendship with Brad Feld, for example, my friendship with Fred, which both continue deeply to this day. And then, of course, we invested in Return Path, your pharma gig. So, we learned a lot. I learned a lot. But the emotional ride of the rollercoaster ride of up and down, I mean, it was hard for me, and I think it contributed to the depression that led me to leave the venture business and wander in the desert of, " Who the hell am I? And what do I want to be when I grow up?" Kind of thing.
Matt Blumberg: When you think back on the investments that you led over those years, what's one that stands out as like, " Yeah, and that was just great."? And what's one that in the rear- view mirror you're like, " Oh, how how'd that happen?"?
Jerry Colonna: Well, there were a lot of investments around which I was proud in that way. GeoCities was probably the one that was the biggest outlier, both in terms of return on investment, but also because of, it was the fruition of what I saw was possible. And to be clear, I was first exposed to GeoCities when I was working at CMGI @ Ventures. We provided the first outside capital in to make that happen. But being a participant in the creation of that, felt like participating in the creation of what I would say is the entire, what we now call creator.
Matt Blumberg: Oh, that was Web2 during Web1.
Jerry Colonna: Yeah. Everything from blogging to Instagram to everything that we see now, to all forms of social media could trace its roots back to GeoCities and its couple of competitors at the same time.
Matt Blumberg: Yeah.
Jerry Colonna: So, that was the biggest one. I think there were a couple of... I won't name them because those folks are still around, but there were a couple of like, what the hell was I thinking in terms of the prices we paid?
Matt Blumberg: Right.
Jerry Colonna: And I remember one investment we put like$ 20 million in, and within the year it was dead. And in the end, I mean, I'll say this, I should have paid attention when due diligence showed that the CEO was more interested in the exploration for extraterrestrial life than they were in building a viable business. And I'm not kidding.
Matt Blumberg: Yeah, you got to put that on the due diligence checklist.
Jerry Colonna: Yeah. I know.
Matt Blumberg: Yeah. I mean, look, business building in 1995, 6, 7, and 8, and venture capital in'95, 6, 7, and 8 were both very undisciplined relative to what they are now. So, talk about the wandering in the desert part for a couple minutes. So, Flatiron winds up toward the end of'01. You and Fred and Bob are managing the remnants of the portfolio for a while. You didn't start Reboot for many years.
Jerry Colonna: Right.
Matt Blumberg: What was the journey you went on in those years?
Jerry Colonna: Well, the journey was a kind of early midlife crisis in many ways, and I detail this in Reboot the book, it was also more coming to grips with, let's call it the disordered parts of my personality that really stretched back to a childhood that was marked by depression and alcoholism, my father's alcoholism, and violence and deprivation. It was a tough, tough childhood. And it all came to a head, if you will, when I was 38. And some people think, " Oh, well, he didn't really want to work in the venture business anymore." And there was a part of me that didn't want to do that. But the real reason I didn't want to do that was because, as I often say, the internal me did not map to the external me. And that the resulting depression, which had plagued me almost all of my life, was no longer bearable. And when you find yourself with constant suicidal ideation, you need help.
Matt Blumberg: Yeah.
Jerry Colonna: And you need help. And so, the first few years of the wandering, as I put it, was mostly me sitting on my ass confronting stuff. And when I say that, I mean it literally. I would sit on the meditation cushion. And really dealing with the thoughts and feelings that were coming up. And then I would do a tremendous number of personal development work, as well as traveling the world. I mean, I went to cross the polar ice cap in Greenland. I traveled throughout Patagonia. I visited places. I went to the Grand Canyon three times during this period. I was looking for something. I got into coaching really almost accidentally in the sense that the way the unconscious tends to work is waking up one day and realizing that that's actually what I really want to do.
Matt Blumberg: And what was the spark? Was it that you had gotten the value out of introspection yourself and wanted others to get there?
Jerry Colonna: No. No. What it was, was a young guy had come into my office, kind of lost himself, and I found myself... Right. He was coming into network his way into a startup, and I was kind, and I went and took a meeting, and had nothing to gain from it. I don't even remember his name. But I remember asking him why he had become a lawyer in the first place, because he wanted to leave the firm and he wanted to join a startup. And then he started to cry. And I then gave him a couple of books to read and responded really from my heart. And then I said, " I love doing this. I love being fully present, being real. No bullshit." The books I gave him were books that had helped me. And I realized that I had a gift, and that part of the depression that I had was that I was not actually living into my vocation. And by vocation, I mean its root word, calling from the divine. A few weeks ago, Fred and I had lunch in Manhattan, and he made me cry because he said something to the effect, he said, " You're a great investor, but now you're doing the thing you were born to do, and it shows." So, anyway, that's more information than you asked.
Matt Blumberg: No. No. I always tell people when they ask me for career advice to look for the intersection of the thing they're great at and the thing they love. And I fear that most people never find that, or many people never find that.
Jerry Colonna: Right.
Matt Blumberg: And sometimes it takes a career or two careers before you find that.
Jerry Colonna: Or four.
Matt Blumberg: Exactly.
Jerry Colonna: Right.
Matt Blumberg: So, let's shift gears a little bit and talk about your new work, Reunion. I was lucky enough that you gave me an advanced copy, so I read it. I could try to summarize it. Why don't you do that? Because you'll do much better than I will. So, give us a sense of what it is and how it came to be.
Jerry Colonna: So, one of the core animating theses of Reboot, my first book, and even the work that we do, is that better humans make better leaders. And that's a simplistic way of saying to lead well, you have to do this inner work, and that if you don't do your inner work, you run the risk of spreading toxicity throughout an organization. And that is true and valid. What I came to realize, and it was during the pandemic, and it was during the protests for George Floyd's murder that I came to realize that that was insufficient. And like so many things in my life, the thing that propelled me to see that most clearly was my daughter, my daughter, Emma, who's 30 now. And there's this moment in the summer of 2020 when like so many of us, I was freaked out about COVID. And I live in a nice farm outside of Boulder, Colorado, and it's really, really protected by 40 acres and all of this stuff. And my daughter was protesting. And one night she's trapped on the Manhattan Bridge between a phalanx of cops coming from Brooklyn and a phalanx coming from Manhattan. And there were probably 5, 000 people on the bridge, but she's texting me about what to do if she gets pepper sprayed. I said before that this is a vocation, I realized that God gave me a gift, that I can speak in a way that I can be heard. That in addition to the privilege and power that comes from this body, this cisgender, white, straight body with all its power and privilege, I have a moral and ethical responsibility to lean into hard questions and to speak up. And the result is Reunion. And what Reunion basically says, the animating question of Reboot was, " How have I been complicit in creating the conditions in my life that I say I don't want? Yeah, yeah, yeah, you say you don't want to be busy, but you fill your day with meetings. What's up?" Really important question. In this case, the corollary question is, " How have I been complicit in and benefited from a world I say I don't want to see?" See, we don't want to see gun violence as the number one cause of death of children. Nobody wants to see that. And yet, Americans continue to buy guns, far outpacing anybody else. What's up with that? And I would argue that so much of the behavior that we've seen, so much of the behavior that we see even now at this time, Matt, where a fucking beer company gets protested because of having a trans woman as a spokespersons. What the fuck? So much of what we see about the world right now stems from this profound fear of the other person. And so, hopefully people will find, what I tried to do with Reunion is to provide a hopeful way of encountering, because Reunion implies that there was a time when we were actually not divided. And this isn't some Pollyanna bullshit, like, " Oh, let's all just get along and sing Kumbaya." This is like, no, we actually have to do this real work. Just like you have to do your work as a leader, you have to do your work because we have all been complicit in what is referred to as systemic othering. So, that's Reunion.
Matt Blumberg: Yeah. I don't know if you coined that term or if I just hadn't run across it-
Jerry Colonna: I hadn't coined it. I first encountered the word through the works of a Berkeley professor named John A. Powell, who is a law professor, and he runs the Othering and Belonging Institute at the University of California Berkeley.
Matt Blumberg: Yeah. So, it's a really powerful word and construct that really resonated with me, and I think it works in lots of directions or on lots of levels. Right?
Jerry Colonna: Mm- hmm.
Matt Blumberg: Certainly, racism has always been othering. Right?
Jerry Colonna: Mm-hmm.
Matt Blumberg: I mean, go back thousands of years. That's maybe a new term, but that's not a new concept. But when I take a look at what is happening in our country now, it feels like it's nothing but othering. And some of it is in the politics. Right? Like, if you say A, then I have to say not A, right? And how the two principal parties have gotten just further and further and further apart. But some of it's also, I find it sometimes even in well- intentioned identity politics, and-
Jerry Colonna: We're always making the other of the other person.
Matt Blumberg: Right.
Jerry Colonna: Right.
Matt Blumberg: So, I think one of the points you make in Reunion, and you just said it a couple minutes ago, is that people who are leaders of anything need to be thoughtful about the lack of belonging or othering, and think about what they can do to change that.
Jerry Colonna: Right.
Matt Blumberg: And I'd love ... Go ahead.
Jerry Colonna: Yeah. I'll say two things. One is, I'm happy that you saw what I was trying to build, which is a through- line, that there is a connection between antisemitism and anti- Black racism. That there's a connection between our obsession with guns and a nativist anti- immigration stance. That when we deny human and civil rights to women and their right to determine their own body experience, that there's a relationship when we deny gender- affirming care to a trans teenager. That this is all actually part of a larger experience going on. And I was really struck during the three years that I was working on Reunion, two- and-a- half, by an Elie Wiesel quote. And Elie obviously is a great teacher as it relates to the Holocaust, but even more our own experience with that form of othering. And of course, he said, " Neutrality always favors the oppressor." And we're at a funny moment right now in business leadership because we tell ourselves our version of, " Shut up and dribble." That pejorative exhortation to an athlete who might take a knee, " Shut up. Just do the thing you were supposed to do." But if I believe, and I do believe this, that we are humans before we are CEOs, then our neutrality, " Shut up and dribble. Just focus on the business." Favors the oppressor.
Matt Blumberg: That's a really powerful quote. I've read a lot of Elie Wiesel, and I don't recall that, but that's a really powerful one. And you take that into the realm of geopolitics for a second and you look at the major countries that are remaining neutral in the Russia unprovoked-
Jerry Colonna: The land war in Europe.
Matt Blumberg: Yeah. Unprovoked war on the Ukraine. And they're calling it an internal dispute or a territorial dispute, and they're not aligned. Right? That is not doing anything to favor the Ukrainians, let's put it that way.
Jerry Colonna: Right. Look, my father was in the army at the tail end of World War II. He didn't see combat. And when he and his unit went through Italy and into Germany, it was towards the end, but my uncles did. And they were imperfect. The United States was imperfect during that time. Ken Burns' documentary on America and the Holocaust is very, very clear. But what if we had shut up and dribbled then?
Matt Blumberg: Well, there were some moments where we did-
Jerry Colonna: Yes.
Matt Blumberg: But when it counted, at the end, we didn't. That's right.
Jerry Colonna: That's right. That's right. That's absolutely right. But what if that was our policy forever and ever and ever? Okay. I mean, for God's sake, this is what's at stake. The number one cause of death for children under the age of 20 is gun violence. Gun violence. You have children. I have children. I was writing this book when the shooting at Uvalde, Texas happened.
Matt Blumberg: Sadly, you were writing the book when thousands of shootings happened.
Jerry Colonna: Exactly. Because every day. So, what's it going to take for business leaders to stand up?
Matt Blumberg: So, let's double click on that, and maybe we'll make that the topic we riff on to close, because I love these conversations to have practical takeaways for the CEOs who listen.
Jerry Colonna: Mm- hmm.
Matt Blumberg: What can the CEO of a startup, a scale- up, 50- person company, 200, even a 500 person company, what can that person do? What should that person do? And this is the thing I struggle with personally as a CEO. How do you think about making decisions and public stances where you are likely going to alienate half your employees and half your potential customers in a world where everyone's the other? So, what can a CEO do? What should a CEO do? I guess, the other way around. And how do you think about dealing with such a polarized world?
Jerry Colonna: So, I gave you an organizing question, which was, " How have I been complicit in and benefited from?" The corollary question to that is, " What am I willing to give up that I love and value in order to see the world that I want to be?" And you said in your imagined scenario that you're going to alienate 50% of your employees. That's the fear. That's what I'm suggesting you need to be willing to confront. Now, the truth is, you're not going to alienate 50% of your employees. Study after study after study shows that our employees want us to take stance. But you may alienate some. But here's the thing, Matt, you could do a lot of things to generate profit. You could sell methamphetamines, you could sell fentanyl, you'd generate a lot of profit, but you would violate your core values and principles. So, you're not going to do that. By the way, not every leader has the same values. Some leaders are perfectly happy running Ponzi schemes. We know this. So, what you're really saying is, should I really lead with an articulated consistent set of values that says, " Belonging is one of the most important principles at this company."? Now, imagine you make a statement like that, and 10% of your employees say, " I'm out of here." Goodbye. Good riddance to bad trash. Okay? Come on. Now, the real fear is what happens to my stock price? What happens to investors? Now, I'm not suggesting that you take your eye off the ball in building the business, but we can walk and chew gum at the same time. We can be really good at running the container of the business profitably, thoughtfully, being good stewards of capital, hiring and firing people as necessary, and live according to values.
Matt Blumberg: What do you think the role of the board is?
Jerry Colonna: I think it's the same thing. I think it's absolutely the same thing. What is the fear of the board? In a public scenario the fear of the board is, "Oh my God, we can't have ESG values, environmental and social governance values." What? Why?" Because our stock price is going to go down? What about the investors who buy the company because they like that? Oh, you mean you have to actually work hard to sell the relationship between behaving well and doing well? Okay. It's hard. Newsflash, being a CEO, being a board member is hard anyway.
Matt Blumberg: Are the values of the company, the values of the CEO, the leadership team, the owners? They're all different people. They all have different values. How do you reconcile that as-
Jerry Colonna: Do you reconcile it now, Matt?
Matt Blumberg: Sometimes it's easier than others.
Jerry Colonna: Yeah. Oh, you mean, you use conversation and discussion and respect to come to a unified view of how we're going to navigate conflicting commitments and values. I mean, this is why in some ways, this is natural work for me because the tools that we teach, " Listen well to your employees." Right? That's a value statement. The tools that we teach are the exact same tools. Whether you choose to do a DEI program or not is up to you, but what is not a choice is neutrality. How you want to manifest your values, it's up to you. Nobody calls into question Chick- fil- A's decision to close on Sundays because of their values. I mean, some people do, but nobody really... Right? They don't get dinged in the stock market because of this. But somehow, a value system that's rooted in empathy is somehow an anathema. That's silly, and worse, that leads to death. And I don't mean to be overly dramatic, but look at the statistics. The number one cause of death for trans teens is suicide. And we're debating whether or not they can see a therapist. What? Where's our compassion?
Matt Blumberg: I think one of the most poignant quotes in the book, and maybe this is a good thing to end on, is that, " The business of business is belonging."
Jerry Colonna: Glad you liked that one.
Matt Blumberg: And it's a riff on Calvin Coolidge or whatever, right? " The business of America is business." " The business of business is belonging." So, do a very quick unpack on that and then we'll wrap up.
Jerry Colonna: Sure. And I don't mean to say in opposition to the business of business being to generate enough profit so that there's a tomorrow. I think that that's critically important. But that's-
Matt Blumberg: Otherwise, there is no business. Right?
Jerry Colonna: That's right. That's right. So, the container of the business needs tending to. Always has, always will. But the why of the business. There's something expansive and generative about going beyond generating profit for profit's sake and into generating profit to foster a sense of community with your clients, with your employees, with the employees' families. I mean, look, I know how you run the business. Right? If you had an employee retreat day, I bet you all the kids of your employees would be there. Why? Because you got values. You were asking me about CMP. CMP was one of the most admired companies in the country because it had an onsite daycare system. And my oldest two children benefited from their dad changing their diapers every day and feeding them strained peas at lunchtime. It was a better place to work because they wasted money on an onsite daycare program. Okay? We know this is true. This is not debatable.
Matt Blumberg: Not everyone knows that's true, but it is at the root of an employee- centric culture.
Jerry Colonna: That's right. That's right.
Matt Blumberg: A people-first culture, which is what-
Jerry Colonna: People- first culture. That's right. That's right. That's right.
Matt Blumberg: Jerry Colonna, thank you for the conversation. Thank you for Reunion.
Jerry Colonna: Thank you.
Matt Blumberg: And thank you for teaching everybody so much about the things you've learned in your journey and how all of us can do a better job making the world a better place.
Jerry Colonna: Amen, brother. Thank you for having me.
In this deep dive episode, Matt Blumberg and Jerry Colonna chat about Jerry’s time as a VC, how he redirected his career journey, and the meaning of vocation. They also discuss Jerry’s new book, Reunion, and what it looks like to examine our complicity in our circumstances.
Jerry is the founder of Reboot, one of the premier leadership consulting/coaching firms in the world. Don’t miss this thoughtful episode.