As Seth Godin puts it, Dave Balter has delivered a personal account of what it means to be a tech entrepreneur. Books like this are rare indeed and you won’t soon forget it. Today, I’m joined by Dave Balter to discuss the inspiration behind his new book, The Humility Imperative: Effective Leadership in an Era of Arrogance.

Dave shares with me how he learned these lessons the hard way through his own successes and failures in the tech industry, and why it’s so important to find the balance of humility in an industry that also demands self-assurance.

Nikki Van Noy: I am joined today by Dave Balter, the author of the new book, The Humility Imperative: Effective Leadership in an Era of Arrogance. Dave, thank you so much for joining me today.

Dave Balter: Thanks Nikki, happy to be here.

Nikki Van Noy: I am looking at the cover of your book right now, which has a chicken on it, and it’s making me very happy just looking at this image as we speak.

Dave Balter: I actually am not an expert in fowls but it may be a rooster. I actually don’t know. Do we know if it’s a rooster or chicken?

Nikki Van Noy: I will take your name for it, I have a two-year-old who could probably answer that question authoritatively for us.

Dave Balter: Someone just asked me about it, they called it a chicken too, so maybe let’s go with the chicken, that’s good.

Nikki Van Noy: Thank you for sparing my ego on that one, Dave, I appreciate it.

Dave Balter: No problem.

The Balance

Nikki Van Noy: Dave, let’s start by giving listeners an idea of who you are and what you’ve done that led you to want to write this book?

Dave Balter: Sure, well, I’m currently CEO of a company called Flipside Crypto. It’s a startup in the grandest of terms. Venture capital-backed, 25 employees, focused on analytics for the crypto industry, but much more important than that, this is my 7th company. All of them sort of in that same vein, take an idea, shape it into something, build a team, raise some capital, if all goes well, exit the business. I’ve done that a few times and I am also involved as an investor into startups. I have 50 portfolio companies and I sit on some boards and things like that.

I don’t know what that makes me anymore, but I suppose knowing enough about how startups get from A to Z is probably the best way to put it.

Nikki Van Noy: It sounds like it makes you very knowledgeable and frankly, it also makes you sound like someone who could fall into arrogance, just because you’ve seen so much from so many different, I would think.

Dave Balter: Even talking through my background, as I’m saying it, I’m like, this is arrogance. The one reason I put this book together like–okay, let’s reframe it entirely. I built a company and I’m learning every day about how to work with employees, et cetera, et cetera.

The problem is, I’m supposed to be articulate in my history and what I’ve done. Even as it flows out, it just sounds super arrogant. Well, the problem is as you do those things and you talk about what you do, that’s the way you continue to grow other companies, or to get investment, et cetera. So, there’s always this conflict between I should be a humble leader, at the same time, I’m supposed to be arrogant enough to express my accomplishments.

Nikki Van Noy: You know, that’s interesting, from my vantage point, I didn’t get that at all. What I took away was how much experience you have and how it sounds diversified, but having said that, you do raise an interesting point. I find myself getting very vague about my background in certain moments for that same reason, which is an interesting impulse and one that I haven’t really thought through until right now.

Dave Balter: Yeah, it’s constant conflict, you know. I think I’ve gotten to this point mainly because I had so many knock-me-off-the-pedestal moments or failing due to complete hubris, and having to take the time to learn to listen to others, and be reflective. Even once you come through that awareness curve, you’re still pushed as an executive or an entrepreneur to go and have to express why you are going to be better than somebody else.

When you go raise capital from a venture capitalist, they need you to say, “Oh, I’ve done all this, and I’ve accomplished this, and here’s why this is going to be the best company in the world,” and all these things. The wind is pushing at your back–oh no, no! Keep acting bigger and bolder and maybe less humble in a way. All the while, you’re going yeah, jeez, to really be successful, humility is at the cornerstone of everything. How do you balance those two things?

I find that conflict rife in everything I do every day and I struggle with it frankly.

The Era of Arrogance

Nikki Van Noy: I love the humanity of that, first of all, especially with someone with your track record. I’d love to dive into your view because I’m fascinated by the lens of your book. I’ve talked to a lot of people who have written books about leadership, but I haven’t talked to anyone who has written about it from this angle.

First of all, the subtitle of your book is Effective Leadership in an Era of Arrogance. Talk to me about the era of arrogance and how you see the business environment currently?

Dave Balter: Well look, regardless of your political views, you could probably say we’re in an era where they leadership of our country appreciates, or is intentionally on a position of arrogance. Said in whatever non-humble way I can. We’re watching leaders puff out their chest and use arrogance as a weapon, maybe that’s a way to put it. We’ve come through a history of, whether it’s executives like Jeff Bezos or politicians, these are idolized individuals that say, “Wow, they’ve accomplished so much!” and leadership comes from these massive accomplishments. For you to be a leader, you need to embody this greatness.

Now, when you start peeling that back, there are many micro-moments in our lives, as entrepreneurs and executives, where it’s the humble side of that which actually creates the true leadership position, even though this guise of arrogance may be all around you. Putting that into color, I need to articulate my successful outcomes of selling companies or advising companies. But in the day to day of working with employees or inspiring a coworker, you need to come at that by listening, and by being thoughtful, and using other people’s approaches, and getting rid of all that arrogance.

Putting that all together, you still have to be an effective leader, but you’re living within this bubble of arrogance that is all around us now.

Nikki Van Noy: That’s really interesting. Hearing you talk about how you sort of have to switch back and forth between those two modes, depending on what function you’re doing at any given moment in time.

Dave Balter: That’s entirely correct. We just closed around the capital for our company from venture capitalists, and the whole process is a game of, “Why will this crazy idea work and why am I the person to make it work?” You can’t show too much humility in that process. You need to show bravado and, you know, to get from A to B–this is what I’m going to do, and how I’m going to hire the best team, and use the capital the most efficiently, and beat all the competitors, et cetera. Meanwhile, I’m talking to my cofounders like man, gosh, how do we figure all these out? Let’s be honest with each other, this is really hard, and what are we going to do? You’re faced with it at every turn.

I do think I should just say for a moment, venture capitalists have become extremely cognizant of some of this as well. The right ones expect some level of humility in the presentations and the discussions. Because they know that the best entrepreneurs don’t have all the answers.

That still doesn’t mean you should let your guard down all the time and that makes it complex.

Nikki Van Noy: Absolutely, that makes a lot of sense. Humility seems like a specific topic to me, simply because I don’t hear about it on a regular basis. I’m curious if there’s anything in your own career or experience that drew your attention toward this facet of leadership?

Dave Balter: Well, there’s a whole chapter in the book that’s dedicated to this idea. I’ll give you the story of what brought this about. I founded a company in 2000/2001 called BzzAgent. It was a social marketing business, pre-Facebook, pretwitter. The model was, we would give away free product to any consumer, any individual, and by the very nature of them receiving that product and trying it, they will go tell others about it. We all know how word of mouth works, if they tell others about it, even if negative at times, that creates sales.

We started this company, 200 investors told us that they were uninterested in the business, so we built it on the backs of customers. Our first customer was actually a publisher, Penguin Publishing for a book called The Frog King, and that book broke all of its sales targets with our campaign.

We grew the business to about 3 million in revenue, we raised a whole bunch of venture capital, we ended up on the cover of the New York Times Magazine, we were the cover story. We became this thing, we became bigger than ourselves. I mean, I thought I was a god among men–I’m on the cover of the New York Times Magazine, people are calling us geniuses, but by the time 2008/2009 rolled around, when we were growing incredibly fast, social media showed up. I was sort of too good, too smart to know that Facebook could have an impact on our business.

The recession hit–our revenues were cut in half in 2009, out of the blue. When I turned to the people around me, a lot of them started saying, “Well, you’ve always said you have all the answers. You didn’t really listen to any of us,” and, “Your hubris is what got us here. You thought you can beat everybody else, and your competitors would never catch up.” It took a real breakdown of my own ego in order to come out of this.

I joined a CEO group. They were not light on me in teaching me a bit about how to learn from others. I had to let go of two-thirds of my staff, and I had to hear from many of those people but, over time, I’ve started really understanding that as I embraced the nature of learning from others, my business began succeeding again.

Going through that war, I came out on the other side and any CEO, any individual, any entrepreneur who believes that they have all the answers, everything is about them, eventually, there’s a reckoning that will come. Not to bring back politics, but maybe that will happen soon.

On the other side of that, that is The Humility Imperative in a nutshell, which is to really let go of your ego, and transform your thinking through the engagement of others, and you will find success follows.

It took a lot, and it was a very painful couple of years.

Nikki Van Noy: Yeah, I mean, that story is almost cinematic in scope, listening to it.

Dave Balter: Yeah, it was a time, and there’s still people today who they’ll say, “Balter 2.0.” I say, “What do you mean? What are you talking about?” They say, “You know what it was like to work with you back then? Man, you were a terror.”

I still have strong opinions and that’s an important part. Having humility doesn’t mean you aren’t strong in your convictions, and I will find ways to articulate them, and inspire people and do all those things but before, the edges were on everything. The sharpest of elbows. I would tear people down in meetings or I would just completely disregard their thinking. Yeah, Balter 2.0. I don’t know what that is. I look forward to it.

Nikki Van Noy: Who knows.

Dave Balter: Who knows, yeah.

Nikki Van Noy: I am so impressed with the frankness of the way that you can talk about that. One thing I want to point out, and this is me extrapolating, looking at your author picture, but I’m guessing that you were very young when this first success hit, is that correct?

Dave Balter: Let’s see if I have this right, I was 33, 34 when starting that company. Yeah, young in the grand scheme.

Nikki Van Noy: New York Times Magazine cover, I mean, that is a pretty extreme form of success and especially because, placing ourselves back in 2000/2001, things were so different then. You really were on the cutting edge it sounds like.

Dave Balter: Yeah, there are a couple of funny lessons from that. The first is when they told me–when they interview you for stories like that, they don’t tell you you’re going to be a cover story. When they told me, which was three days before it was coming out, by the way, this is the cover story, my first response was, “Oh, are you putting my picture on the cover?” Such a non-humble question and, I will never forget the reporter laughing and saying, “No, that’s for really important people.”

I’m like what? Looking back, of course, I’m just some startup guy that caught a big idea and made something of it. Then I looked at all the other covers and there are all these very famous, really people who’d changed the world, that type of thing. Yeah, that was tough, and I remember once I was at a dinner and someone turned to me at the dinner and said, “Hey, this social media stuff must be really impacting your business?”

Facebook was sort of coming online and brands could either use something like us and maybe this Facebook thing. I said, “What are you talking about? What do you mean?” We had just a great quarter, and I shut this person down. I remember they were sort of taken aback and then I went home, and I thought, why would he say that to me?

I was so in my head, I was humble, but not to him. And then our business just fell off the cliff and many customers said, “Well, I can get for it free on Facebook, what you’re offering.” It was different but I understand now why they thought that, but you know, the approach should have been, really, “Why would you say that? I haven’t thought about that, let’s have a discussion.”

Because I clearly missed at that moment what he really meant, and I should have paid attention. I would have saved a lot of employee’s jobs and the company would not have gone through some real pain to get to the other side.

Burn Out

Nikki Van Noy: That’s interesting to hear. I mean, obviously, over the long term, you’ve done fine, but you do think that your personal history and the history of your business could have been different if humility was at play?

Dave Balter: Look, if I look at it in reverse, we sold because we had to. What I mean by that is after 10 years of running the company, my board pulled me aside after a board meeting and said, “It is time to sell.” I said, “What do you mean?” And they said, “Well, you’ve gotten the company back to profitability but something is missing, and that was the worst board meeting you’ve ever had.”

I couldn’t see it at the time. I was burned out, I was tired, I just came through in the past year laying off a bunch of people, rebuilding with an iron fist in some ways, and getting us to a point of stability. Enough where we could actually sell the company, but I couldn’t even see that I wasn’t leading anymore. I was just trudging through this thing. I think we left a lot of value on the table. I think we could have built a company that could have been era-defining and we didn’t find our way there.

We did fine, I shouldn’t be griping. We did fine, and we loved who bought the company and we love being part of that company, but we missed, I think, what could have been possible. Back in the early days of BzzAge, I used to be called on a lot to give speeches because I was this young buck who created this company. Anyway, so I go do these speeches and I thought I was really good. I will never forget I went to one speaking gig here in Boston and the guy in front of me, Frederick Markini I think his name was, just completely destroyed the audience.

I mean to a point where it was like, when I got up there, it was crickets. I was tapping the microphone, because people are laughing, they are doing all of these things. This is the first time that it had ever been like, “Woah, I am not that good.” Afterward, I called this guy and I’m like, “What did you do? How did you do that?” He’s like, “Come over, I’ll teach you my tricks.”

So, I go over and he said he did two things, which stuck out to me and they showed the story of the capacity of a great leader. Anyway, the first is he went and found the person who won the world’s speaking competition–a competition to do speeches. I mean this guy won and he showed me the videos of this person. This guy is doing push-ups on stage and has all of these sayings. He said, “I went and trained with this guy, okay?”

So, there is commitment. The second, which I thought was awesome, is he said, “If you want to learn humility, I did standup comedy.” This guy wasn’t a comedian by any stretch, and he said, “I stood up there at the comedy connection in Boston and you know it was painful and horrible but you learned to not step on your lines.” I will never forget him saying that and I said, “Yeah, you’re right. I do, I like to run over everything, run over, run over.”

And so my lesson of that–first of all I thought that was hilarious and this guy was so good at what he did, but my lesson was you have to learn from others. Everyone is learning from someone else, but that stuck with me. It still sticks with me.

Nikki Van Noy: That’s hardcore. Comedy is not forgiving, and Boston is not that forgiving. If you put those two things together you are really ready to be humbled.

Dave Balter: Yeah, anyway I don’t know where that guy is today, but I probably never told him. Frederick, if you are listening, thank you. That was useful stuff.

Nikki Van Noy: Absolutely. Switching gears here a little bit, you have written this book as a series of essays, and I would love to hear why you choose that tactic?

Dave Balter: Yeah, so, two reasons. One, you know I could have written the book as the journey from a young buck who doesn’t know his way around the world, and the lessons of pain, and all the way through the natural crisis and out the other side. I think we’ve probably all read books like that. I have read many that are great, but it’s been done. So that was one.

The second is much more important, which is I find humility is truly in the eye of the beholder. It is through all the people that surround you, not my one journey. So, as an example, when we search for new people to join the company, sometimes we write these job descriptions, which are what I actually want to say about a person. Not, “Knows Excel, and 10 years of history building product,” but in my words, this is what they really should be doing and it can be very witty and a little bit spicy.

The reason for that is really important, the person who reads that has the humility to laugh at what they do for a living or, maybe understand that there are different approaches to the world or has a sense of humor even. That they would read these things, and the people who reach out reflect that. And so some chapters are just the job descriptions.

We need to talk about the people, and everyone you touch on your journey, and how they perceive the individual through that journey, to understand humility. It is not my story, it is all the people that end up along the path, and all of the different touchpoints that happened with them. So, the 37 chapters really resonate through that. There are even a few chapters on my interpersonal relationships with my wife, and now my ex-wife.

I have a current wife, but my ex-wife is in there, and my current wife is in there and those are all moments of humility. Going through the journey of building something, through the eyes of them, is very much as much part of the process as it is through your own eyes. That is why we chose to put it together this way.

Nikki Van Noy: Yeah, you know Dave the one thing that keeps running through my mind as I am listening to you is this idea that a lot of leaders talk about the importance of learning from your failures, but a much smaller percentage of leaders actually share their failures so openly. That to me seems like a very differentiating factor with you.

So, with the understanding that this is a book about leadership, and it is not a memoir, it sounds like, in the process of writing this, you had somewhat of a memoir experience probably, looking back over your life and how things played out. Is that accurate?

Dave Balter: I am chuckling because there is an article in here, or chapter, that came from an article I initially wrote, which is “You Can Be an Entrepreneur and Not Get Divorced.” Why I’m laughing is when I got divorced, I wrote the first version of this. I wrote this article, which basically walks through what a mess I was to my wife. I was disconnected from child-raising, I was leaving half-eaten pretzels around the house while looking at my Blackberry.

I did all of these cruel things to really wreck our marriage, and I wrote this article and I wanted to publish it. I went to my now newly ex-wife and I said, “I want to publish this article,” and she got really mad at me. “You can save that for your memoirs,” she said, and I will never forget I was like, “Memoirs? I don’t even–why, oh god.” I was so fragile.

Anyway, I didn’t publish it and about two years later I went back to her and I said, “Hey, I really think this will help a lot of people. A lot of entrepreneurs come to me now and say, ‘My marriage is falling apart, you’ve been through this. Do you have any lessons?’ and I really think this would be really helpful. Can you let me publish this?” We are now quite close friends. She said, “Sure, you could publish it.” So, I published it. It went into Inc. Magazine, the version of the book is a little different, but that went out and right after I called her and I said, “Is it okay–are you okay?”

She said, “Yeah, it turned out okay.” I said, “Well, what do you mean?” She said, “Well, you got your article published and I got four dates out of it.” So, yeah, but the statement about ‘you can save that for your memoirs’ will stick with me forever. I thought, “Oh my god.” Even there, she was saying you are so non-humble. You lack the ability to see yourself, said with such vitriol, ‘You can save that for your memoirs,’ you know? So, these are my memoirs but there are some stories about getting through all of that stuff.

Nikki Van Noy: So as you look back at this stuff, how did that feel to you? What was the experience like?

Dave Balter: Well, it was mixed. I mean, there is catharsis. I got through this time in my life where I wrecked a marriage and rebuilt from there. There is certainly a bunch of reflection, you know, there is a chapter on how to break up with employees.

I used to break up pretty poorly with employees. I always find this strange. You work side by side with someone for five years and then it’s like poof, see you later, you know? See you on the interwebs. And you think, “But we used to have lunch every day.” We are now unable to have a relationship. So, the reflection–I look back at that and I think that the interpersonal is much more important than the little thing that is business. Looking back is, how do I keep my eyes open? Every day you get caught up in that.

We just let go of someone at the company that I run now. I realized that I don’t talk to this person anymore and what should I do? So, I look back at this and I think, “Wait a second, I just wrote a whole chapter on this.” I reached out to him a week later. You have to be reminded. So, putting this on paper helps remind me.

How Things are Changing

Nikki Van Noy: I love that. A little earlier on, when we were talking about this sort of era of arrogance that we’re in, as you speak with other leaders and maybe watch emerging leaders, do you see signs that we’re moving out of that or are there any mindset shifts or anything you see happening?

Dave Balter: That is a big, big question. I’ll reflect on a story that still troubles me to this day. I mentioned the CEO group I was part of before, and there was a CEO in there who was just completely out for himself. Now, he’s been very successful, this is not in the book, but it is a thing that stuck with us. The other CEO’s,  we were very open with the CEO and said, “Man, you are really evil. You know, you will not only let people go, but you also won’t even be in the room,” and we just came down on the guy.

Anyway, we called it the “assaholic syndrome,” and the reason we did is that he was an assaholic, which he recognized, but he was really successful. Folks like me were thinking, “God, I wish I could be like him. Why can’t I be more of a jerk to others, and more inconsiderate of the pain in order to get to the goal?” You know, you’re set up to be, “Can I make a billion-dollar company?” Or whatever, right? How can I be tougher? And I always thought about that.

There is a level of arrogance that ends up being more of what we would call assaholic and my problem with it is this gentleman, and many others that I know, some of the best execs I know, are just like this. They almost lack a gene that makes them care enough. They can get rid of an employee. You know I fret–I mean gosh, when it comes time to get rid of anyone, no matter how many times, I try to find any possible way to save them. I have all of these conversations, do all of these things, and someone like this is like, snap their fingers, done, you’re gone, okay? I struggle with that.

To get to your question, in today’s political environment, you are seeing a lot of lessons. Do I believe that the pendulum is going to start to swing in the other direction? I do. There is still a lot of power being wielded by someone with a lot of arrogance, and a whole load of assaholicism, regardless of your political views. It sucks to know that that’s what my children look up to.

Nikki Van Noy: Yeah, seriously.

Dave Balter: I just lost a whole bunch of readers possibly, but I am not coming down on any one side. Let me just say that. I am just saying I would like a leader that treats people with less arrogance.

Nikki Van Noy: I am personally finding this conversation very therapeutic, for what it’s worth. The last thing I would love to ask you, it seems to me as someone who is admittedly not involved in the tech industry, but a lot of successful entrepreneurs are becoming younger and younger. I would love it if you would just take a minute to talk directly to them, and about how maybe they can avoid some of these lessons, or bring humility into play earlier to their own advantage.

Dave Balter: Yeah, I think the most important thing is to know who you want to be and to aim for that early. You know, there is no story without a crisis, we know that, and so maybe you want to go through the crisis moments in order to learn from the pain of what comes out of that, but I would tell you, if you can, skip that part. Skip the story and focus on the stuff that really creates outcomes. Outcomes being both financial or business-oriented, but also emotional and growing as a person.

I would think a lot about that today and, frankly, a lot of the methodologies, they are so public now. Like how good is my Snapchat game or my TikTok game? Or am I really good at Tweeting pithy things that people follow? Those are superficial to the end result of how am I going to treat people around me and how am I going to establish good leadership qualities? I would just say it can be really hard because you see a lot of things coming at you.

If you look at any Twitter stream, it feels like everyone’s got it all figured out, but they don’t. If you just focus on what you do and how you treat people, I promise you the outcomes will be a whole lot better.

Nikki Van Noy: Beautiful. Dave, you’re such a pleasure to talk to and I am especially happy to talk to you today. The book again is The Humility Imperative. Dave, where else can listeners find you outside of the book?

Dave Balter: There is a website called It actually serves as a forward to each chapter. So, there is a lesson in each chapter, which you could probably glean by reading it, but if you want to know exactly what the humility thread to that chapter is, the website does that. There are some pretty fascinating pictures that come along with it. So, check that out,

Nikki Van Noy: Excellent. Dave, best of luck with the book and again, thanks so much for joining me.

Dave Balter: Thank you, Nikki.