How Cheezburger founder’s inner chatter affected his company (before he turned things around)

If you’re stuck or you feel like you’re failing to achieve one of your big goals and you can’t figure out why, this interview is for you. I want you to consider that maybe the road block isn’t outside of you. Maybe it’s not lack of funding, maybe it’s not a problem with the site. Maybe the road block is really inside your head.

Most entrepreneurs wont talk about this topic but today I’ve got a guest who will.

Ben Huh is the founder of Cheezburger Inc, which operates a network of incredibly viral sites including, icanhascheezburger, meanbase,, knowyourmeme, and failblog.

His latest product is the Cheezburger app where you can find all his funny sites and express your own sense of humor.

Along with him, and this part  is exceptionally different for us,  he has his business coach, Khalid Halim. He is a partner at Reboot, a coaching company that helps entrepreneurs improve by acquiring practical skills and by learning radical self inquiry.

Ben Huh

Ben Huh


Ben Huh is the founder and CEO of Cheezburger, which is behind hugely popular blogs.


Full Interview Transcript

Andrew: Hey there Freedom Fighters. My name is Andrew Warner and I am the founder of, home of the ambitious upstart and I’ve got a very different interview for you here today. If you’re stuck or you feel like you are failing to achieve one of your big goals and you can’t figure out why, this interview is for you. I want you to consider that maybe the road block isn’t outside of you. Maybe it’s not lack of funding, maybe it’s not a problem with the site. Maybe the road block is really inside your head. Maybe you’re your own worst enemy. Or your own obstacle.

Now, most entrepreneurs will not talk about this topic but today I’ve got a guest who will. Ben Huh is the founder of Cheezburger Inc, which operates a network of incredibly viral sites including, icanhascheezburger, meanbase,, knowyourmeme, and failblog. His latest product is the Cheezburger app where you can find all his funny sites and express your own sense of humor. To make your friends laugh go get the Cheezburger app in the App Store.

Along with him, and this is the part that is exceptionally different for us, here today he has got his business coach. Khalid Halim. He is a partner at Reboot, a coaching company that help entrepreneurs improve by acquiring practical skills and by learning radical self inquiry. This interview is sponsored by Toptal. If you need a developer I guarantee that you will find the perfect developer. I mean, seriously, if you’re not happy with the developer that you get with Toptal, they will give you a refund. If you go to

Guys, welcome. Thanks, for doing this interview.

Ben: Thanks for having us on, Andrew.

Andrew: Ben if I was in college, if I didn’t know you, know you and just saw you from the outside, awhile back, what would I have seen?

Ben: You probably find somebody who laughs a lot. Who is probably enjoying his life very, very much. You would probably find somebody that on the outside doesn’t act or look like your typical CEO. Yeah, that’s probably about right.

Andrew: What about this? A guy who raised $30 million? A guy who had over 370 million page views? A guy who was on Bravo? A guy who was on Mixergy to talk about the success of his company. I mean a bigger accomplishment, I can’t think of. But seriously, these were big accomplishments, right?

Ben: Yeah, I mean, we had a reality TV show on Bravo, we won multiple Webby awards. We’ve acquired companies. We’ve raised now closer to $40 million. So we’ve done all of that stuff. Yeah.

Andrew: So frankly, I see that. I can’t imagine having a single problem. It seems like everything is going great. Everybody knows Cheezburger or has seen the site, it feels like. Very few people have achieved as much as you have. What on the inside would we have missed if we saw you?

Ben: You know there’s a famous philosopher said, “More money, more problems” and I think that is absolutely true. We raised a lot of extra capital and that is a lot of expectations. And I think one of the traps that we fall into, is that we’ve realized that we have something to lose. And it’s probably true. But what got me here was acting like I didn’t have anything to lose. I think that’s a real important distinction. That as we start to actually generate money and get investors, that we forget.

Andrew: Give me an example of something that you did because you had or you felt like you had nothing to lose?

Ben: I would say what was on my mind. I would actually just go out and be like, “Hey let’s try this.” I wouldn’t have a filter. I would just get out there and do what I needed to do to get the job done. And it’s almost like watching a kid who doesn’t understand that he can fail. And I think that’s really important when you are an entrepreneur.

Andrew: Well here’s one that I remember. Didn’t you go after, or didn’t you write a note about the Guinness Book of World Records people? What was that?

Ben: A long time ago their website had a little button that said “break this record” next to every single one. So like, you know the man who ate the most cheeseburgers in one sitting. Break this record. They also had a listing for the world’s most deadliest terrorist attack. And there was a link that said “break this record.” And so we called them out on it. And we sometimes do it in a funny way. So mine was to actually reply to a take down notice link in The Guinness Book of World Records saying, we would like this photo removed and I basically said “Go *F* yourself.”

Andrew: Well you showed a photo of it on your site and they said, “Hey take that thing down. We don’t give you permission.” and you said, “Yeah, go *F* yourself.” That got you a ton of publicity and I can see how if you have nothing to lose of course you go for that.

Ben: Why not?

Andrew: When you change things around, give me an example of what was going on in your head there and how it impacted you?

Ben: You start to get defensive instead of offensive. You start to actually think about while these are the things I want to protect, here are the things that I have. And I think that in start-ups the analogy that the best defense is the best offense is absolutely true. You think that you are in a mature market when you really are not. You barely found product market fit. You need to continue to excel at that and continue to grow that market fit, to grow the business that you have. But once you start to think that I have something to lose, then you start worrying about defense versus of offense.

Andrew: And when you think, I have something to lose, what’s a defensive thing that you did that kept you from growing?

Ben: I started putting filters on what I would do. I started thinking like a CEO. And I don’t mean that in an entrepreneur way, I started thinking like, well this is my reputation. This is what people think of me. I have made it here so far, so maybe I need to start making myself look good. All that stuff.

Andrew: What do you mean? Do you have an example of something specific that you did that held you back or something that you didn’t say to somebody that made you feel like…

Ben: Also, this is kind of funny. So I forgot what year this was, I think that it was 2010. GQ put me on the list of, I was number 10 in the list of worst dressed CEOs of the Silicon Valley. First of all, I don’t live in the valley. But that’s beside the point. So here’s this list with like Steve Jobs and Mark Zuckerberg and me and Reed Hoffman. And I am like, holy crap, this is amazing.

And then I’m like, they are criticizing me for wearing cat T-shirts. Right, this is part of my job. This is part of my identity of the company. And I had a funny response back to them, challenging them to a fashion duel. Which they actually took on and then backed out of. But also I started thinking, maybe I should dress better. Maybe their criticism is right.

Andrew: Oh, I see. And that translates to maybe I should also act differently internally. Maybe I should also be thinking okay. So at what point do you start engaging with the Reboot?

Ben: I started actually working with Jerry Colonna who is Khalid’s partner in New York. I want to say 2013. That sounds about right.

Andrew: And what was going on in your business that led you there?

Ben: My investor Brad Feld recommended that I do that. That I find somebody who is in my corner that doesn’t have a financial stake or business stake in the company, who can look out for my performance and well being as the CEO. That was the starting point.

Andrew: Khalid, at that point you guys starting working with Ben. Do venture capitalists sometimes not just make introductions like this but require it? Like say “Hey look if you want an ongoing relationship with us, you have to talk to Reboot.”

Khalid: Yes, they do and we usually don’t work in those engagements. We need to be there on behalf of the entrepreneur and it’s always a little bit of a warning sign to us if the venture capitalist calls and says, “Hey can you go fix this, entrepreneur.”

Andrew: I see.

Khalid: It’s a little bit different with somebody like Brad Feld and his relationship with most people in this portfolio. At Reboot we work with a number of them. It comes out of a general concern. Not, “Hey go fix this person.” But, “Hey you really need somebody that you can talk to that doesn’t have a financial stake in what you are doing. So they’re really in your corner.”

Ben: So what is an entrepreneur going through when they really need somebody in their corner? What’s going on internally that they can’t share with the rest of the world?

Khalid: What isn’t going on internally? That is my first reaction to that. I think that fundamentally, you’re dealing with people who are often CEOs for the first time. And so you know we talk about it a lot. It gets a lot of air time, but this idea of imposter syndrome. This feeling of what if everybody finds out that I’m just making it up as I go along.

And there are a number of variations on that theme but you can’t stop at a board meeting and go, “Hey guys I am freaking out. And I don’t know what I am doing.” But often times it’s that not knowing what they’re doing, or as Ben really made a good point of earlier. It’s not having anything to lose that does make them successful. But it’s also that that creates the fear.

Andrew: Ben did you feel that at the time you had imposter syndrome? That you felt like maybe you’re not ready for this?

Ben: What’s fascinating is that when I started the business and I felt like that I couldn’t lose, because there was no down side, I didn’t know that I had imposter syndrome. I probably did. And then somebody put a label on it and it’s like, it’s real. Right? I feel like I started to understand the imposter syndrome as like it’s almost like somebody else in the room with you all the time when I started reading about it. So unfortunately, in order to get over and get through having the imposter syndrome and to accept that you have it, is to recognize that it is there. But I was actually doing pretty well at ignoring it until I couldn’t anymore.

Andrew: You know what I’ve noticed that we don’t recognize that we have these voices in our heads or as Jerry Colonna, your co-founder partner, Khalid says, “the monster in your head.” So if we don’t recognize that we feel like we are an imposter we’re not ready to do this. Ben, what did you notice?

Ben: Can you rephrase the question?

Andrew: I’m wondering about how it manifests itself. What is it about your experience that makes you say, you know what? There is a problem here. You may not recognize that you are feeling like an imposter. You may not recognize that you are feeling not quite up to this. But you do recognize that there is something that is the problem. What is that?

Ben: So you’re a frog in a pot. What happens is that the heat gets turned up little by little and so you’re fine. You’re comfortable and then you’re a little bit less uncomfortable. And then you’re a little bit less uncomfortable in that. And things go wrong and your team screws up and you waste a million dollars out of the 10 million you got. And you are like that’s okay you have nine million more. And your product launch doesn’t go right and your software doesn’t work. And your marketing sucks and then you are like, you know it is really getting hot in here. And then by the time you jump out of the pot and you’re looking for help, you’re about fried. Right?

Andrew: I see. And so what you recognize is, I’ve lost money and so I have lost control of my management of the business not necessarily, there’s something going on in my head. So Khalid, you guys are experienced entrepreneurs. I know you were, we’re not here to talk about your story, but you are an experienced entrepreneur, right? What was the business that you built and sold?

Khalid: The business that I built and sold was a private catering company. And then I spent two years as a turn around CEO for a private investment firm.

Andrew: Jerry Colonna, a well known, former venture capitalist. Why not sit down with Ben and say here, let’s restructure your company. Let’s talk about who needs to be the CEO. Let’s talk about who needs to be the COO. Let’s talk about a couple of ways that we can set up a weekly meeting for the team and give you practical business advice. And save the therapy for a therapist whose couch you will set on after you have sold your business for $150 million, minimum. For now we have some serious work to do. Why not take that more practical sounding direction?

Khalid: That’s a great question and one we get all of the time. And Jerry has this great phrase called “Taking your seat.” And what that means is, there are a number of books that you can buy on how to run a company. There’s a myriad of blogs, podcasts things like that. At the end of the day you have to perform. And the performance comes from you. The metaphor that I often say is that I would never give you a book on golf and then think that you knew how to play golf. You still have to play the game. And you have to play the game with a coach.

What a coach does that you can’t do, is that I can watch from the outside, what’s going on. I can get curious in ways that maybe you can’t get curious about. You made this move; what was going on there? What was so important that you were trying to protect it, in that way? Or so scary that you were trying to avoid it in that way? And through that building of awareness and the coaching relationship, Ben and other entrepreneurs that sit with us at Reboot then have the tools to understand how they make decisions. Which is if you sit down with a mentor and they give you a blueprint for a reorg, as soon as things go off course, you don’t have a blueprint any more. And if you don’t know how that was constructed from internally, then you can’t adapt on the fly.

Andrew: Ben’s nodding the whole time. You can’t see him because we’re on a three way Skype call. He is nodding the whole time that you are talking. But Ben, what if he didn’t give you a blueprint for how to reorganize your business but instead said here’s how we think about structuring the business. Here’s how we’re putting this reorg together for you. Now that you understand the model, get out there and get a COO and make sure that you are on top of your finances. And make sure that your launch… now Khalid’s smiling… what’s wrong with that way of thinking? Why is that naive? What am I missing there?

Ben: So we got here by really, really good by taking orders and executing against it. Right? And I mean that we got here positively, as in we were able to become entrepreneurs. And also we got here negatively, as in we fucked up. Right? Because we’re so good at getting shit done, that we didn’t actually go out and say, “Oh this is the right thing to do, therefore I must do it.” The problem with that approach is, it’s not my answer. It’s not the right solution for me. I have to make that determination.

If you are going to tell me that’s the better answer or you suggest that I do it. Why should I be CEO? Somebody else is running the company. Right? I know my business the best. And it’s not just coming from an ego it’s also coming from the other direction, which is you are going to go tell your team, “Hey I am going to replace my team, here is the new org structure.” They are going to ask you why. What’s the answer?

Andrew: The thing I am getting at then, is why not spend time, and I’m with you on this, I’m not challenging because I don’t agree. I’m challenging because I don’t know how to exactly how to articulate it and I don’t know your perspective on it. But we have two different approaches. One is to teach the practical business skills. The other is to teach the mental inner game. Why the focus at all on the inner game? Instead of teaching the business skills so that you know how to make decisions. So that you know how to run the company. So that you can explain to your team the direction that you’re going and why you are doing it. Why is the inner mental game even important?

Ben: So my advisors and my investors and my peers tell me that. I get that information from them all the time. That information is readily and freely available. Best practices have been written. And in fact, there is so much of it, there is a phenomenon called advisor whiplash. Right? You should fire that guy. No, you shouldn’t fire that guy. You should give him a raise and a promotion. What of this is the right answer? And if you are center is not there, if who you are and what you believe in is not strong, then you’re going to make world class decisions that are not very consistent.

Andrew: I see. And the only way to get your center, is to understand who you are. What is really going on in your head. And if one of the things that is going on in your head is, “I have imposter syndrome” if Khalid, one of your clients comes in and you help them understand. Actually how do you help someone understand that they have imposter syndrome? And then what do you do to alleviate that pain?

Khalid: I want to be clear about one thing. The place for practical skills. We in the startup world, there is so much uncertainty that it is worth spending the time to learn the stuff that you actually have control over. Right? How to hire, how to fire, how to recruit. So there is a place for that. But the large majority of things that you’re going to run into, when you are in the business of creating a future, is stuff that nobody’s ever seen before.

So to answer your question, how do work with somebody that has imposter syndrome? So nobody actually comes in and says that I have imposter syndrome. Usually the way it shows up, is some situation where they’ve acted out of fear, to protect being discovered. And that’s going to show up with a number of… the number one place that shows up is I am fighting with my co-founder. Right? Or I just haven’t written my board deck or given my investor… I haven’t sent an investor update in three months. I mean there are cues.

Andrew: Things that they’re avoiding or conflicts that they’re creating and that tells you that there is something underneath it and it could be a sense of feeling out of place.

Khalid: Yes, exactly.

Andrew: How do you get them to recognize that?

Khalid: So one of the things that entrepreneurs are really good at is moving really, really fast. And my partner Jerry Colonna has a lot of super powers. And just so people know Jerry mentored me for a year in coaching. So I actually learned a lot of what I bring into coaching from Jerry. And what I would say is one of his main superpowers in to not allowing you to run past an emotion. If you’re ever talking to Jerry and you hear, stay with that emotion, just for a minute. You know that tears are right on the horizon.

Andrew: I see.

Khalid: Because often what we do is we act out of anxiety to avoid an emotion. So what we will do in coaching is slow the action down. We have them pause and reflect on that moment before they took that action. And what was it that they were feeling.

Andrew: I see. So if I tell you, I just stormed out of a meeting because everybody in there is an idiot. I need to fire them all. They don’t know what they’re doing. And I just yelled at them and I left the meeting. And I don’t know how I can go back and fire them or work it out with them. How do you now get me to stay in the emotion that draws out my sense of feeling out of place?

Khalid: So the most important thing to understand there is that right before you stormed out you had a feeling that created that. Usually I would use the phrasing as, okay rewind the tape. Tell me what was happening right before you stormed out? And how did that make you feel? There are three sets of beliefs being run all of the time. The belief about ourself, right? A belief about other people and a belief about how the world works.

And in that configuration of three beliefs, they didn’t care about me or they were attacking me. Or I felt really disrespected. Or most people who storm out work in a zero sum game, which is a belief about how the world works. But we would look to uncover those beliefs under the emotion that created the storming out. The storming out is a symptom of something much deeper.

Andrew: And by understanding what I believe about what led me to have that emotion, that led me to have that outbreak, how does that help?

Khalid: We operate through a series of mental models. And this isn’t therapy but a lot of them were formed when we were very young. And family systems, how we figured out we belong in the world. And when Ben was talking about, I realized that I had something to lose. One of the things that we realized first is oh no, I am in the cool kids club. I belong here. But I don’t feel like I belong and so I am constantly afraid.

Andrew: And that’s why you think that you are going to lose your access to the cool club because you don’t think that you belong and that helps you understand, I don’t feel like I belong here. Okay.

Khalid: We have created a series of mental models to belong. And as soon as one of those are violated we have an emotion. And that emotion response is usually either fight or flight. So you’re either going to yell or you are going to storm out. So we just look at that and so your question of how do uncovering the beliefs help. If we all of a sudden take something unconscious like a mental model and make it conscience, we have the opportunity to reconstruct that model.

Andrew: Okay. So once we are aware of what the model is we can reconstruct it, understand what is underneath it. And then what makes it go away? So if I say “Hey I don’t belong here.” Frankly, you know what I am going to be honest with you Ben. You make me feel sometimes like maybe I don’t belong in front of the camera.

First of all. Look at the backdrop that you bring with you, Right? Cheezburger backdrop. We meet at a party. I immediately go over to talk to him and comment on his glasses because he had glasses that were really striking. That anyone in the room would have noticed. And I feel like, I’m the kind of person that can walk over. There is a way that you dress, a way that you carry yourself.

So now I am aware of what I’m thinking that Ben is really a showman. Right down to his heart. Makes me feel like what if I babble here? What if I’m just not looking right? And that kind of thought in my head while I’m talking will distract me. Will have my questions come across as insecure gobblygook. I’ve recognized it. I mean obviously, I’ve gotten past it here. But what do I do if I recognize it but I can’t get past it? What’s the next step for eliminating that so that it doesn’t get in the way?

Khalid: The first step is always what is the fear? So what if Ben doesn’t acknowledge you? What happens? Stepping into that. Noticing in that moment what’s at stake for you.

Andrew: I see almost like questioning it.

Ben: So Khalid, you and I can real play this. So I just posted on medium, a blog post about a show that I want to do at Cheezburger where I invite people to smoke weed and we talk about funny stuff. So Khalid, I was really, really scared about posting that post. And I’m like should I really do this? Because this is really interesting and it’s funny. I think that it can be a lot of fun. It creates some positive momentum in the conversation about how to let loose. And things like that. But I had this fear. So Khalid would probably ask me, “Why do you have that fear”?

Khalid: And the question is, usually what we fear is we fear loss. What might you lose that you value.

Andrew: Okay.

Ben: I’m afraid that people will think that I am just a fucking pothead.

Khalid: And if they think that, then what happens?

Ben: Nothing. That’s the weird part.

Khalid: He’s been working with me for awhile so.

Ben: That’s like opening the bidding at auction at $2000 and somebody goes $10 million.

Andrew: I see. So eventually you do get down to nothing. Here it just happens to be quick. He might something like no investor will want to put money into you. And then you say, then what happens? And so on.

Ben: We usually get to broke and destitute on the streets and no one will ever hire me again or work with me again.

Andrew: I have felt that. Every entrepreneur must feel that. How do you solve that?

Khalid: Through a lot of coaching, but also realizing the value in taking that act. One of the things that we work on in coaching is having anything that you do, the success of it, be determined by the action. Meaning if I have the courage to have a conversation with somebody, that I gauge my value and my success on the courage to have the conversation. Because I can’t control how they’re going to react.

Andrew: Okay.

Khalid: So this is that part about going to inwards. How do you want to show up in the world? What kind of CEO do you want to be? Look most start-ups fail. We can’t guarantee the outcome. But what we have control over is how we play the game.

Andrew: What about this? You are teaching Ben. You are his sensei. You guys at Reboot, you can’t obviously work with everyone. Frankly you are expensive, you’re too expensive for most people and you don’t have the time. So have these bootcamps where multiple entrepreneurs come in. And they can help each other, they can get into a safe place where they can be this open. You got in there one evening. Tell me if I got this story right? Jerry stepped aside as he was trying to help someone, you stepped in and started to help them and as you were talking and helping them. Somewhere in the middle you thought, what?

Khalid: This is a great story. This is from our last bootcamp. And it’s important to note that Jerry is my mentor. Because I think that I know the story that you are talking about. I stated helping them and there was a moment where I realized that if I performed at the level of my mentor or better, not saying that I could. Even that statement, I am hedging. Right? But that everything was at stake for me. And so I pulled back and I made a joke.

Andrew: And so instead of continuing where you were really helping someone you were in a groove with them. You were showing them something about themselves. And you were being the person that you worked with Jerry to become and express, you suddenly pulled back. So if you can’t do it, then what kind of role model are you for me and for Ben and for everyone else?

Ben: Yeah Khalid? What the hell? Oh my goodness.

Khalid: Yeah, exactly. So I will say one thing. I have both a coach and a therapist to work on these things. But at the end of the day, I think that it’s in demonstrating that I’m a human too. Right? That we all have our issues. We actually brought that into the room the next day at the bootcamp and had it be an experience for everyone.

And I would say that the most important part of the bootcamp happens on the first night. Where everybody fills out an application about their fears. And we mix them all up. We have different people read different ones and every single person goes I could have written that. I could have written that. And so it’s really important for me as a coach and one of the reasons why me as an operator, Jerry as a BC, I think one of the real things that we offer is when Ben comes in and says hey I have to fire somebody. I have the experience in my body. The emotion of what it was like to fire somebody. In that fear, I can use that as a gateway to help my clients. I’m not supposed to be the expert as a coach. Those are mentors and advisors.

Andrew: I would even say, I sometimes say well if that coach is imperfect, then he is not really a coach. Then he is a fraud. And that is what keeps me from learning from that person. And on the reverse end, if I’m not perfect, then how can I give somebody direction in the company if I just screwed up. And what I was trying to get you to say, and interviewing is a horrible way to get someone to say something. It’s much better to just say, here’s the way I feel about it and get you to tell me what you think.

I feel that that mistake or that issue, I don’t even know if it was a mistake. It was you being human and you accepting that it wasn’t the end of your coaching career. And it didn’t have this big message to Ben and to me and to everyone else and to yourself. Is what makes you the kind of person who I would want as a coach. Because we all have these, what one of my past interviewees called, butterfly thoughts. These thoughts that just come through. But if you attach significance to them and hold onto them, then they’re corrupting. If you recognize them, that’s the skill.

Khalid: That’s right. That’s right. And I would say that having that experience and then having… the beauty of having partners at Reboot is that they are all coaches, so having over dinner that night. Looking at it in that way, I would say that we emerged from that as a stronger partnership because of it.

Andrew: Because of you being open?

Khalid: That is what we brought into the room the next day is that learning.

Andrew: Ben, you did a pre-interview about this and I was so amazed that before you got here, you didn’t just do a pre-interview. But you weren’t hedging. You talked to April here on the Mixergy team and you said things like, “If my business is a failure then I am a failure.” And I underlined that and I made it big in my notes because that seems like a healthy thought. You know, if my business is a failure then I’m a failure. It means that I have to really work my tail off to make sure that this business is not a failure or else I have let too many people down. Including myself. So that makes you fight harder. Isn’t that a better… isn’t that good thought? Isn’t that a helpful thought?

Ben: It is helpful until you make it a terrible, terrible thing for your life. It is helpful in motivating you to work hard. But it actually can get to a point where it is so overbearing that you can make terrible decisions for the business. Or you end up paralyzing yourself making decisions.

Andrew: So what did you do with that thought that you felt it needed to be changed?

Ben: I am not my business.

Andrew: But what happened? Did it lead to a problem in the business when you are associating yourself so closely with the business that when it failed you failed? What is an example of a problem?

Ben: I would correct the language there. Which is it wasn’t if the business failed, I failed it. It’s that if the business failed I am a failure.

Andrew: Ah, even bigger.

Khalid: What you did there was actually correct posture to take. If the business failed. I failed. But that gives you the opportunity to be a success next time. When you go all the way down the dark, dark hole to “I am a failure,” when you personify it, that’s when end up in a negative place. But what we work with in coaching is because you failed, all that means is you failed. Not that you are a failure.

Ben: And there’s a really interesting, kind of beautiful, kind of dramaticness to being kind of a martyr with your business. Right, like if I fail and I’ll go down with the ship. Nobody wants you to fucking go down with the ship. Go start another company. The thing that we want you to do, is take all of the money that you have spent, that you have learned from. That you create a business out of that experience and take more of our money, go do the next one. Given that you are a sane better educated human being at the other end of it.

Andrew: I see. And when you think that I am a potential failure here then it hurts and wears away your sanity. Ben you were on Mixergy about five years ago and you talked about the pre-Cheezburger business that failed. That setback led you to depression. Right? Which kept you from being effective. That’s what you were trying to avoid. And when you were going through depression what kind of leader were you?

Ben: I didn’t leave the room. I wasn’t even able to go out and by food to feed myself. Right? That’s a level of depression that is very unhealthy and that could cause death. The type of depression that we’re talking about in the business is the one where you delay making decisions. You don’t own up to the hard choices. That you waste time. Time is the number one killer of businesses. And so what we have to do is fight the time and get more done. Find the right answer by using the time wisely. And if you’re depressed at your business, you can’t use your time wisely.

Andrew: You were also if you needed to have some layoffs at Cheezburger and because layoffs equal setback or potential failure. And potential failure of the business means potential, well it means that you are a failure too. What did that cause you to do about the layoff decision?

Ben: You know luckily thanks to my board members and coaching I was in a much better place this time around. And what I realized is that I am paid to do what is right for this business. I am paid to do what is the best decision that I can make as CEO. And there is no emotional attachment to those decisions. The emotional attachments that I have is to the people who worked with me. And that is a separate problem.

I can go out and help them find a job. I can go out help bring recruiters to help them. I can go out and send their resumes out to my network. That is a different problem to solve than having to cut expenses from my company. And what happens is, especially in our industry, we don’t understand how privileged we are. With the vast majority of people that we will let go, will probably go out and find a better job. Right? And so we are looking at not a terrible choice here.

Andrew: How about you took on money, you burned it. Here is another thought that you told April. You said that your inner chatter said, “I wasted my investors’ money.” So were you starting to linger on that?

Ben: Yes, I think that I spent this year period on the road helping sell advertising for our sales team. And I was hardly ever in the office. And it wasn’t to say that I wasn’t doing work. Clearly I was out there just busting ass trying to do this. But the company was missing its CEO from being in the office. I was overly emphasizing the one thing that I thought I needed that would also take me out of the office.

So I was kind of running away from the problem. I think that my board members recognized that and said, “Look you are doing good work but you need to balance this out. You need to be in the office because they want to see you. You are their leader.” So that kind of decision making gets really clouded when you are depressed.

Andrew: Were you depressed?

Ben: You know, I was nowhere near where I was before.

Andrew: You mean as the previous company.

Ben: I wasn’t happy. So Khalid and I worked on this for awhile of what makes me happy. I have all of this guilt because I shouldn’t deserve happiness because I suck.

Andrew: What made you say that you sucked?

Ben: I lost all of this money. I used up all of this money from these investors and we were spinning our wheels.

Andrew: How did you lose the money? Where did it go?

Ben: That’s a really good question. You know on paper it went to salary. That’s what most technology companies do. We really used up the money because I didn’t make the right decisions fast enough. And a lot of the money went away because we had some bad luck. The market and personnel circumstances, things like that, affected our ability to execute. And that happens. Those are things that are just facts of life. It’s not something that you can control. All you can do is move forward.

Andrew: The facts of life were someone was ill, market went…

Ben: Yes, our chief revenue officer, who basically ran the business. And we knew that she had cancer coming in. Her name is Amber Dawn and a few months after she joined, I mean she was a phenomenal person. People loved her. She helped our company grow from $5 million in ad revenue to $50 million. She led that team. And her cancer came back strong. She had it, not in remission but under some control. She entered the hospital and she was in there for four months, trying to work out of her hospital bed, taking chemo.

Andrew: Amazing.

Ben: So, I don’t know how to sell ads. Right? Like that’s the kind of thing that people don’t realize. Just because you are CEO doesn’t mean that you know how to do everything. Right? That’s why you hire good people. And the good person that I hired wasn’t able to work. What do I do?

Andrew: I see.

Ben: Well we were running out of money and so we had to lay off the team that we had just hired. We had to layoff somebody I think that was just two months into their job or one month into their job. We had to lay off the woman who was in the hospital with cancer. And that’s the kind of stuff that really you don’t expect. It kind of catches you out of left field.

Andrew: Khalid, the model that I have in my head for being a tough man is the fake coach that I sometimes hear, “You better man-up and it doesn’t matter what people think. And just stop thinking about it and just get back in the game.” Is that a better way to deal with things? Why aren’t you advocating that? Why aren’t you saying so what people sick just get back in there?

Khalid: I would just start by making the comment, Ben was in my office last week and from what I can tell Ben’s investors love him. Right, even though he feels like he let them down. And that gets to the question that you’re asking. You have to ask ourselves what promise are we actually making to our investors and to our employees. And the promise isn’t that you are going to man-up and be tough and pretend that it isn’t hard when it’s hard.

The promise that you are making and what Ben was alluding to with time and decisions is that you would show up every day and make the best decisions that you can. And some days you’re not going to feel like making decisions and I think that what we work to in coaching is, you’ve worked to hire the best team you can find. And when the going gets tough we often isolate ourselves. Right?

And so it’s not man-up. It’s, where do you need to make a request that you’re not making the request? And that gets back to imposter syndrome because making a request of somebody means you don’t know. Right? And that gets into the fear and all of that. And so what we challenge our entrepreneurs who work with us to do is to bring the emotional soup that is going on underneath the behavior. Manning up sometimes means saying, “I don’t know what to do. I’m scared”.

Andrew: I’m scared. And by doing that, by saying that I am scared then we are more likely to deal with the problem. And say well… actually why if I am recognizing that I am scared wouldn’t that be more, less likely to go talk to a friend. Say, “Hey Rand Fishkin I am having trouble selling ads. You’re really good. You’re a buddy of mine could you give me feedback”? If I am scared of doing that and I am now becoming aware of my fear, how does being aware alleviate it?

Khalid: You can’t actually act with anything that’s transparent to you. So the awareness gives us an opportunity to interact with it.

Andrew: So unless I’m aware of the fear I can’t handle it. If I’m suppressing the fact that I’m afraid, it’s controlling me and I can’t squish it. I see.

Khalid: You’re probably yelling and storming out of the conference room. To use your earlier example.

Andrew: The analogy that I had in my head, was if somebody was punching me in the face the whole time I was doing this interview and I didn’t acknowledge that I was being punched in the face, I couldn’t put my hand up to stop them. But if I acknowledged it, then I could move away. And I could stop them or I could do something. And you’re saying the same thing. That there is some monster in our head that is jabbing away at us and unless we recognize it, we can’t put our hand up and stop it and deal with it.

Khalid: And the other piece is that when we acknowledge the existence of something, it takes some of its power away. Right? When I go, if I said, “Look, I’m really nervous to be on this interview today,” then the nervousness instantly drops. And you will see speakers get up and say, “I’m really excited to be here and I’m really nervous.” And they’re actually trained to do that. I don’t know if you were ever coached to do that. But it takes it out of that dark shameful place. And makes it available to then work with.

Now I am not encouraging people to get in front of their company every day and say “I’m scared, I’m scared, I’m scared.” Part of being a leader is being able to show people the future that you want to move towards. But there is a time and a place where it’s appropriate to lean on the people that you’ve hired because they are experts. You don’t need to have all the answers.

Andrew: Ben you were going to say something?

Ben: I think part of the problem with the advice culture in the technology world, the entrepreneurship world is that we deal with the veneer. Here’s the problem that I have which is like this tiny, tiny little tip of this iceberg. Right? And what we try to find out in our coaching sessions is, where is the iceberg? You are seeing the tip of the iceberg, what is deep down inside? So that never happens again. That what are the tools to solve this class of problems, not just this specific problem. That’s why the advice isn’t prescripted.

Andrew: And the tip of the ice berg is, “I should have let that person go and I haven’t. And it has been a month and I am a procrastinator.” The iceberg is that I am not letting them go because I don’t want to hurt their feelings. The iceberg is that if I let them go then everyone will know that I made a bad decision in hiring them. Right? So that’s what we’re trying to understand ourselves to get at and once we understand it’s much easier to act.

Ben: The tip of the iceberg is that every time I go in front of the audience, in front of my company, I keep telling them how scared I am. Right? What’s the underlying problem?

Andrew: I see.

Ben: I don’t believe in the market. I don’t believe in our product. Okay, well why do you not believe in that? Well okay, I feel like we don’t have a good technical team. Whatever the answer is…

Andrew: Did you not believe in your product at one point?

Ben: No, I believe in our product.

Andrew: And you always did? You never got to that place?

Ben: I never got to that place but I didn’t believe in the execution. I didn’t believe in our ability to do it in a fast enough time. Because the product is actually pretty evident to me in the numbers. I actually have a relatively easy product to understand because people show up they laugh, they leave. It’s not like a complicated enterprise software. But what’s difficult about it is, how do you know what the next step is? When you have something that has that many users, there’s a lot of ways to screw it up.

Andrew: I am on Cheezburger C-HE-Z

Ben: C-H-E-E-Z

Andrew: C-H-E-E-Z excuse me. Double E-Z burger. This is an app that you came out. Was this part of the struggle? Getting this app out?

Ben: That took three years to get out.

Andrew: Why?

Ben: And the thing was, we actually went for the web version. We struggled with the framework of the technology. We had a turn over in the technical leadership. One of the really difficult parts of a start-up is that when things are great, you kind of pave over problems with money or success or additional fundraising. But when things are going bad, all that collapses upon itself.

Every problem becomes a problem that is insolvable without some other problem being solved. It’s like when the problems all of sudden become moved from tactical to structural, you face this terrible problem, which is, where do you even begin that doesn’t cause everything else to collapse?

Andrew: So can you give me an example of this? So what would you want to do that would lead you to think of another problem? Because in my gut, I relate to it but I can’t picture myself there.

Ben: Sure I will give you an example here. So let’s say that you run a media company and your traffic is growing. If your traffic is growing, your advertising revenue is growing. If your advertising revenue is growing then you can hire more people. And those people can create new websites. Which will create more growth. This is a very beneficial cycle.

Now remove one part of the equation. Our traffic is growing but our revenue is falling. So your server bill is going up so you can’t afford to hire any more people. Well if you can’t hire those people you can’t build more websites to continue your growth. Then your traffic starts falling.

Andrew: And how do you fix any one of those things without knowing unless you fix it all it’s not going to get better. Without thinking that unless you fix it all it’s not going to get better?

Ben: Well hopefully you have some money in the bank, number one job of CEO is to make sure that your team has the resources. Then you start to take it apart. Let’s retract our ambition and figure out what part of this market we can go get easily. What is being ignored by others? What is our competitive advantage? What are we really good at that other people aren’t? What do we know that other people don’t? And you start out with a small win and you start to build that success into something bigger.

Andrew: You know, if it wasn’t you saying it, I might think that this is some Stuart Smalley stuff. Look for a small win. Look for something that you know that you can do and remind yourself in the mirror that you’re good enough and you will do it. What makes if different? What makes it practical that keeps it outside of the realm of the new age. What do you think it is, Ben?

Ben: Everybody knows this feeling. It’s the crazy part about all of this and the really crazy part about the blog post that I wrote a medium about my redemption with this new app. So many people came up to me that said, “I have the same story.” It’s not this metaphysical that only a few of us experienced. This is a tale that is powerful because all of us have gone through it. And so if all of us have gone through the problem, why the fuck is no one talking about it?

Andrew: You know what, I will tell you why. I have talked about it a little bit. About my insecurities about sometimes I will sit down for an interview and I will be nervous. And I feel that it doesn’t communicate strength to people. On the other hand I take a look at one of my friends Ramit Sethi. He always seems invincible. He always acts invincible. He always communicates so much confidence in public that you can’t ever say, well the guy doesn’t know what he’s doing. Right? And meanwhile if you look at him and you look at me, and I’m admitting that at times I’m nervous about sitting in front of an interview. I’m admitting that at times I don’t know, that I’m not happy with the design of the site.

If you’re an outside person looking at two people, and you say well look at this guy he seems to have it all together. He is communicating with great confidence all of the time. And this other guy just keeps trying to wrestle with his look on camera and he is paying attention to the fact that he doesn’t have the cool glasses. I don’t think that I want to be around that guy.

So by standing up, not just you Ben, I think that you can get away with anything. But by standing up as entrepreneurs and being open. Normalizing this problem the way that Jerry Colonna has. Where he says that, “We are all feeling it.” The way that Ben just expressed it here. We need to start talking about it. Don’t the first few people that start talking about it really get hurt? Don’t the first few people who talk about it really end up looking like wimps in comparison to the people who are invincible?

Ben: I do have to say that having plenty of communication is a big factor because there is a very big difference between a man who goes up in front of his team and says, “I’m scared” and another person that says “We’re all fucked.”

Andrew: I see.

Ben: It’s a very big difference. Like how you deliver that same feeling has a huge impact on how the audience responds. The second part is who you believe you are despite all of that, comes through. Something that I coach people here in the company to do is, when you are having a difficult discussion, model yourself so that the other person will model after you.

When you are talking to someone and you are acting nervous and fidgeting you’re hands and you’re feeling insecure and that insecurity shows. The other person that you are having that tough conversation with will get the cues and they’ll respond correspondingly. If you are calm. If you are professional. If you are intelligent and you are caring. The other person will usually reciprocate that.

Andrew: Okay.

Khalid: And this comes down to the intent that you are holding in the conversation. If you’re having a conversation with a person and you are nervous. You’re probably holding an intention of, I want this person to like me. I want this person to be okay. If you are holding the intention of internal measure of the success of the conversation, which is I really care about this person. Sometimes letting somebody go is an act of care. Right? Then you’re going to show up really differently and what Ben was describing was what we call mirror neurons. That you’re going to couple to whatever I am feeling. And that is actually a gift because it is a pathway into connecting with other people and what they’re experiencing.

Andrew: I see. So what you are saying is that if I start to get nervous and jittery then the other person is going to pick up on that and react similarly. Am I right? But it’s actually more. It’s deeper than that.

Ben: It’s way deeper than that. Khalid said it much better.

Andrew: Actually, Khalid, did say it much better than I did. The idea that if I’m walking into a conversation saying that I want this, even to myself, I want this person to like me. Then what I communicate will not be as strong. Not be as clear. Not be as professional as walking in and saying I want this person to do well and I need my company to do well too.

Khalid: If I went into every coaching session worried about making the other person feel a sad or negative emotion, I would be a terrible coach. Because mostly what we do is we have people step into emotions that they don’t want to step into outside of the coaching office. And in that, there is a real opportunity to learn. In every emotion there is a ton of information. What I hold is an internal posture of, I deeply care about this person, so I will take them into those places. If I was worried about what they were feeling I would start freaking out the second I saw them starting to freak out. I would go, I am hurting them. I am hurting them. Let me stop.

Andrew: I see.

Khalid: To bring it back, that is part of what was going on when I pulled back in that coaching session in front of my mentor, Jerry. I was thinking about how Jerry might feel if I performed in that way. Or thinking about what other people might think about me or Jerry. I just got outside of… I got into everybody’s emotion except my intention which was to sincerely help this other person. And it completely shut down the conversation.

Andrew: You’re not a public person. You came over for a drink here at the office. You’re also not a drinker. But I did what everyone does. I started Googling you. I start looking around and I couldn’t find anything except what’s on which is a well designed site. But didn’t give me that much insight into you. You’ve said that you felt a little nervous sitting here to do this interview. You didn’t give into that nervousness the way that I have frankly seen other people who are new. Because it sounds like its because of an intention that you had internally that you set for this conversation. Can you share that publicly? What’s the intention that you walked into this conversation with?

Khalid: So I said it before we started recording. Two intentions. One in regards to the people on this call. I am Ben’s coach. I wanted to show up as Ben’s coach. I didn’t get into, I want to show up as a coach that’s great and amazing and everybody should work with me. I wanted to show up as his coach. And so my intention was for the wellness and well being of Ben on this call. The second thing is, that Jerry and I are completely full. We both have waiting lists. So the other intention is for everybody that I’m not going to be able to coach. Right? And to show up in a way that I can be helpful to them.

Andrew: And if you’d walked in here with a different intention, one of I am going to show Andrew that I am the greatest guest he has ever had. I am going to show everybody that Ben he was lucky to be paying me whatever he paid me. From what I understand the prices are pretty expensive. Would that have led you in the wrong direction? Or is that another way of setting a strong intention that’s helpful?

Khalid: So 100% of the success of that intention depends on everyone but me. So for me to show up as the greatest coach ever I would then have to interview you then after the call and ask you if I showed up as the greatest coach ever? And then your answer determines my success. For me to show up caring about Ben and caring about all of the entrepreneurs that may be listening, 100% success of that intention, depends on me. And that’s where the calm comes from.

Andrew: I see. Because you can control what you do. You can’t control what I do. If you set yourself out to control what I do then you create a crazy experience for yourself. That’s crazy making. Ben you started something with this medium post. I was so moved by it, I said to everybody at Mixergy, “Let’s find a way to get Ben on here.” What do we do differently now? We all can’t go and frankly hire Reboot. Some of us will end up at the bootcamp, but we can’t all possibly be in there. You have an intention for the entrepreneurial community. What is that intention? How do we react to what we’ve learned here?

Ben: I think that what is really important is that people start to find the reality that is in our lives and in our business. And reality as in not the numbers, but what is the truth about the world that we live in. And so if I think to myself, that if I fail, I’m going to end up on the street homeless, that is not the reality. And it causes us to make sub-optimal decisions. If I tell myself that if I can sell this business for a billion dollars then I will be the greatest business person ever on this planet. That is also not true. Right?

The reality is somewhere between those two things. The better we are at seeing the reality then the choices become pretty clear for us because we are the types of people who want to get things done. Then that makes the job of communicating with your board, with your employees that much simpler. Because the pursuit of the true reality.

Andrew: I see. So you want us to dig in and really see what is going on inside of us?

Ben: I want you tell me that when I see you next and I say “How are you doing” and you say “Hey we are doing good” and then we will sit down and have a drink. And then I will say, “Hey how are you really doing?” I don’t ever want you to tell me, “I’m good.” I want you to tell me how really are.

Andrew: And that…

Khalid: And Ben brings up a good point, like you said not everybody can hire Reboot. And we do have the bootcamps and that’s great but at the end of the day it has to be about entrepreneurs having really honest discussions and supporting each other.

Actually one of the things that we have found is the most powerful outcome of the bootcamps is the communication, the email of the attendees afterwards. And I am going to do a quick little plug. Which is in response to that in the next week or two we are going to be launching CEO peer groups because we have seen the power of exactly what Ben is describing. Sit down with another entrepreneur a group of entrepreneurs and talk about what’s really happening. Not the TechCrunch or media of I’m killing it and everything is fine.

Andrew: You curate the list though.

Khalid: What?

Andrew: You curate the list? The group. So the peer group, it’s not me with whoever happened to sign up three persons ahead and two people behind me.

Khalid: No, no. We will be curating the list. Starting with bootcamp alumni because that is the natural place to start. And then we’re looking at a number of other factors. Putting in groups of six to eight people. And then actually facilitate it. So you will have someone trained in helping guide the conversation to go deeper.

Ben: And I also have to say that not everybody is ready to do this. Not every entrepreneur is ready to do this. In fact when I went to go see Jerry in New York, I wasn’t ready. I kind of knew that it was beneficial but I really wasn’t ready. And when Jerry ended up trying to make more time in his schedule to do things like the bootcamp. He said, “Ben I don’t think that we can work together anymore.” That is when I was like oh shit, I am ready. Right? It’s funny how as soon as he took that away I was like, it was actually really valuable even the few times that we met. I actually want to do this. I really do. What can I do?

Andrew: Why weren’t you ready?

Ben: Like all pivotal decisions in your life you have to make that choice to make that progress. And while I know that Brad, let’s go back to the same conversation about when the board tells you that this is the best practice about how to structure your organization. But you don’t necessarily believe in it. You’re not going to do a good job. So when Brad said, “Hey you should go work with Jerry. I’m going to pull a bunch of strings because I know that Jerry is full. I am going to get you in there because I know you need it.” And I say, “Yes, I do need it.” but I went there and I wasn’t sold. Also Jerry scared the hell out of me.

Andrew: He’s not a scary guy. He is like a Buddhist Monk almost.

Ben: You sit on his couch and he makes you cry in the first 10 minutes. You’re like how the hell do I get out of here?

Andrew: You cried the first time you were on his couch?

Ben: Oh yeah.

Andrew: Wow.

Ben: Khalid, that’s his superpower isn’t it?

Khalid: That is. He makes you hang out with emotions until you feel them. And then you can actually do something with them. But yeah, it often shows up as crying. I think I cried in the first 10 minutes as well.

Andrew: Wow, that’s amazing. I had no idea. You know what, I got so excited about an interview that he posted, that I sent him an email with a curse. I said I think that I am such a tranquil guy and I just used the F word in an email with Jerry. He responded right back. He was fine with it. So I guess I have a different view of him because he never made me cry.

Ben: Oh yeah, Jerry curses all the time.

Andrew: Yeah, he does. He does, but I guess that it is outside my way of seeing him. I do see him as a Buddhist Monk somehow who can see inside your soul.

Khalid: Well, in that email sometimes the best way to express something is with a good swear word.

Andrew: Well this is so… I’m so glad that Ben… appreciative that you have the guts to talk about this publicly. I never recognized these thoughts in myself until they caused problems. I mean I remember with my first company. I was going through these feelings of lack of self worth and I wasn’t aware of it. And if I would have been and questioned it I would have realized that we are not doing as bad as in my head that I think we are. And if I’m reacting to it like I think that we are doing so terribly then I’m causing what I am thinking about. Anyway, no one talked about it back then.

I’ve tried to get entrepreneurs to talk about the inner game. What’s going on in their head’s. It’s hard to get them to do it unless they come over for scotch. I’ve said it before and I think that I am a little over scotch. It is very hard to keep drinking with people just to get them to finally be open. And I’m glad that guys at Reboot and you Ben, are pioneering these kinds of conversations. I’ve always wanted to have them. I am so glad that you guys are starting it. I hope that it won’t just start and end with people who are touched by Reboot. But it goes to people who are touched now by Ben and people who are seeing others start talking about this publicly. It’s too important.

Like I said at the top if you are stuck and you are feeling like something’s wrong, maybe it’s time to look inside. You’re not seeing the problem outside, maybe it is time to look inside. Ben, thank you so much for doing this.

Ben: Thank you, I appreciate it.

Andrew: Khalid, thank you so much for doing it. For coming on here and I think this is your first public interview. Am I right?

Khalid: It is my first public anything. Other than my Twitter feed which is mostly retweets of people I care about. I have not written or interviewed publicly at all. This is a first.

Andrew: Well thank you. It means a lot to me that you would trust me and come on here and have this kind of conversation together. The website is In fact forget that go under the app store and look for the Cheezburger app and check it out. See what has come out of all this hard work. And check out You guys do great work. Thank you both and thank you all for being a part of Mixergy. Bye everyone.

Ben: Thank you.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.