Chris Winfield interviews me about what I’ve learned from 1000+ founders

This interview is a little different because this time I’m the one who’s being interviewed. What you may not know is that over the years, I’ve taught others how to interview. I do that because I think the best way to learn something is to teach it to someone else.

Some of my favorite students are people who I’ve interviewed on Mixergy who said that they wanted to learn interviewing from me to see how I got them to be so open, how I got them to understand themselves better through interviews. When I meet someone through an interview, I get to know them better. We create a bond and they want that.

Well, today’s interview is someone who I interviewed years ago. His name is Chris Winfield and I first had him on Mixergy back in 2009. He was running a search and social media marketing firm back then. So he was ahead of the curve when I had him on.

Well, in 2016 he signed up to learn how to interview from me and soon after, he said, “Andrew, I’m an interviewer now. I want to interview you for my site.”

The reason that I want to post it here is because somewhere towards the middle of the interview, Chris said, “Andrew, you did all these interviews. What did you get out of them? Sum it up for me. What’s the point of it all?” And he drew some interesting ideas and understanding that I didn’t even realize I had from doing all these interviews. I want to share it with you. If you’re a fan of Mixergy, if you’re learning along with me, then I think you’ll get a lot of that.

Chris Winfield is an entrepreneur, writer and coach in New York City.


Full Interview Transcript

Andrew: Hey, it’s Andrew Warner. I’m the founder of Mixergy, where I’ve done over 1,300 interviews since 2008 with proven entrepreneurs who I have on here to ask about their experiences. Well, this interview is different from all those because this time I’m the one who’s being interviewed. What you may not know is that over the years, I’ve taught others how to interview. I do that because I think the best way to learn something is to teach it to someone else.

Some of my favorite students are people who I’ve interviewed on Mixergy who said that they wanted to learn interviewing from me to see how I got them to be so open, how I got them to understand themselves better through interviews. Sometimes they do it because they just want to have the kind of experience they see me having. When I meet someone through an interview, I get to know them better. We create a bond and they want that.

Well, today’s interview is someone who I interviewed years ago. This is Chris Winfield. I first had him on Mixergy back in, let me look, January 8th, 2009. He was running a search and social media marketing firm back then. So he was ahead of the curve by a lot. I had him on then. He in 2016 signed up to learn how to interview from me and soon after, he said, “Andrew, I’m an interviewer now. I want to interview you for my site.” And I said, “Sure.”

The reason that I want to post it here is because somewhere towards the middle of the interview, Chris said, “Andrew, you did all these interviews. What did you get out of them? Sum it up for me. What’s the point of it all?” And he drew some interesting ideas from me that I didn’t even realize, some interesting understanding that I didn’t even realize I had from doing all these interviews that I want to share with you. If you’re a fan of Mixergy, if you’re learning along with me, then I think you’ll get a lot of that.

And then what Chris did was he said, “Let me give you a few interviews that you may not remember what you did. Tell me what you learned from them.” I thought that ended up being really insightful. So that’s what this interview is about, Chris interviewing me. You’re going to hear a little bit about my backstory, which I think you’ll already know. Then you’ll get an understanding of what I got out of these interviews and what you can too if you listen to 1,300 interviews. Let’s consider it a shortcut to that.

And since it in the podcast feed, Sachit Gupta, who sells our ads here at Mixergy, would be really upset with me if I didn’t mention that this interview is sponsored by HostGator. Everything that Chris, by the way, is doing, posting interviews on his site, you can do on HostGator. Just go to HostGator, click that one-click install to get WordPress up on your new site and you’re good to go. You can publish interviews. You can publish blog posts. You can sell. You can create a community, the works.

The great thing about HostGator is that because they’re a sponsor of mine, they’re going to give you a big discount if you sign up. All you have to do is go to the special URL. They’ll give you 50% off and that URL is If you hate your hosting company, you should switch to HostGator because you’ll freaking love them and you’ll thank me for it. Go to for that 50% off discount.

All right. Here’s Chris interviewing me.

Chris: All right. Andrew, thank you so much for being here, the original freedom fighter himself, Andrew Warner.

Andrew: Yeah, man.

Chris: Thank you. So, Andrew, when someone asks you, “What do you do?” what do you tell them?

Andrew: You want to know something? I make up something really boring, something like if it’s a doctor, I say I’m a reporter, kind of tell them, “Watch out.” I rarely say entrepreneur, publisher, anything like that. I try to be as boring as possible because I don’t really get much out of meeting people in person and trying to show off. I get a lot more out of having them drop their guard and having them tell me more about themselves.

And then if they’re interesting and if we can work together, then I give them details about how at Mixergy I run a site where entrepreneurs teach and we get proven founders like the founders of Airbnb, the founders of Wikipedia, Y Combinator. That’s when I do it. Otherwise, I try to be as low key as possible.

Chris: How do you describe Mixergy in one sentence or a couple of sentences?

Andrew: It’s a site where proven entrepreneurs teach through interviews and courses.

Chris: Oh, you can do it in one sentence, very nice.

Andrew: Yeah.

Chris: All right. So, before you built a business around interviewing entrepreneurs, you and your brother had a company that you grew to $30 million in revenue, correct?

Andrew: Yeah.

Chris: That you eventually sold. I’m just curious to hear that story a bit. Even if you want to go back further, were you an entrepreneur? I know you do want to call yourself an entrepreneur.

Andrew: No, I do. With work people, I absolutely am happy to. I always considered myself an entrepreneur. As soon as I found out there was a word for what I did, I just loved it. I called myself an entrepreneur even back when people didn’t know what it meant. I had these little businesses. Like one business I remember studying for the SAT and thinking, “This is a long time to prep for the SAT. All I want is like the one evening lesson with a lot of the cool tricks that help me out.”

I had this one teacher who taught me math for the SAT and he said if you clip out the right corner of one of the SAT pages and mark it up, you can use it as a ruler, which will give you an advantage with some of the math questions. I thought just, “Dude, just give me an hour of that and I think I can do pretty well. The rest I can figure out on my own. The rest I can just sit and learn vocabulary words endlessly on my own.”

Anyway, so, I had this idea for a cram session for the SAT. I got this teacher who was so good on board to teach it. He was committed. My brother and I drove through Queens, New York, putting up ads around schools trying to get people to say yes to sign up for this and I couldn’t get anyone to sign up for this, not one.

I realized years later that the reason I couldn’t get one person to sign up was I was doing this at night like a thief. I was walking around after dark when there was no one out there sticking up these signs trying to get people to sign up because I was too much of a wuss to say, “I have this thing to sell.” That was the last time that I ever punked out of selling. I always, always, always said, “I’m going to stand up and sell in the future.”

Chris: So, how did that lead into the business that you and your brother started?

Andrew: Then we started doing all kinds of stuff. We saw that online telephony–this was like early, early internet days when you couldn’t hear any radio online. This was before You couldn’t see video online.

My brother found a way to do online telephony in this weird like CB radio way, where you record on your computer, then you let go of the record button, the audio automatically goes out to your friend, your friend hears it and then they click the button to send the message back to you and you’re kind of talking but only one at a time and each one of these little messages is going out as five-second .wav files or something like that.

So, we did that and a bunch of other little ideas. We just tried to sell them. Almost all of them sold really well, but nothing was a killer hit. We just kept looking for a killer hit. It wasn’t until we said, “Let’s grow our mailing list,” and then tried to find a way to grow the mailing list that we hit on the thing that became the explosive growth, which was online greeting cards.

Chris: Where did that–I guess that inner fortitude or drive to keep going even though you didn’t have the hit, did you both have that?

Andrew: Yeah. I don’t know his. I actually still to this day don’t know what Michael’s motivation is, beyond that he just likes doing cool stuff and I think I gave him some direction that channeled all his engineering and creativity. I know mine. I believe that I’m nothing unless I’m something great. It’s not enough to just do okay. It’s not enough to have a good happy life. I have to do something absolutely great. So, I just kept taking my swings, just kept waiting for my grand slam. I had to just do that grand slam. So, we kept experimenting.

If you think that you’re nothing, that you’re worthless unless you get something big, you’re just going to keep trying. I didn’t want to be worthless. I wanted to do something big.

Chris: Whose judgment of great is that? Is that an internal thing?

Andrew: No. It’s like an external measuring myself against other people. I know that some would say that’s not healthy, but you know what? I don’t care. I don’t give a rat’s ass about them. I give a rat’s ass about people like Andrew Carnegie, who left a huge legacy, both in business but also with the books and ideas that he left behind. I give a rat’s ass about people like Napoleon Hill, whose quote you know that I liked as a kid.

There are some people who just had huge influence on me. I want to measure up to them. I don’t want to just breathe in and out here in this life. I want to do something big. So, that’s where it came from.

Chris: You read Napoleon Hill as a kid?

Andrew: Yeah. I had this hugely bad insomnia. So, I’d go to the library and look for books and audio books that would keep me going while I try to fall asleep. I ended up seeing this cover for “Think and Grow Rich.” And I thought, “Queens Library doesn’t want anyone to get rich. They just want us to keep reading books, like you finish a book and you’re supposed to read the next book. What’s this thing about grow rich and how the hell did it end up here? By accident, it must have been.”

So, I took it out and then I realized hey, I’m not the only person who has this deep ambition. There’s a line in that book where he says, “Everyone who learns about money wants it,” something like that. It’s the kind of thing that a school teacher would say is disgusting or a librarian would want kicked out of her library, but somehow it was in there and it spoke to me and to me, that’s who I am.

There are some people who they see a penis and they say, “I’m gay. I should have been gay my whole life. I don’t know why I didn’t allow it.” For me, it’s like that. I looked at that and I said, “I’m an entrepreneur my whole life. I didn’t know. This guy gave me a word. This guy gave me a sense. This guy gave me this whole culture that exists and I want to be a part of that.” Everyone else was trying to tell me I should be happy with what I am, that I should read and enjoy books for the sake of the education and culture. No. This is what I wanted. And I still do.

Chris: That quote that I read that I know that is one of your favorite is, “Whatever the mind can conceive and believe, it can achieve.” How has that been true in your life? I’m also curious from both sides, the negative and positive. I think it works both ways.

Andrew: Yeah. By the way, the thing that really got me with that sentence is that he actually could sum up his whole book in a phrase that rhymed. It’s really hard to take a whole book, a whole core philosophy and sum it up like that. You see how hard it is. You’re interviewing entrepreneurs. It’s hard for an entrepreneur to sum up what the business is about in a single sentence and this guy took his whole philosophy and he said, “Basically, here’s what I’m about. If you focus your mind on something, you will achieve it.” But as you said, it’s both a positive and a negative.

Chris: It’s such an interesting–actually, beyond just the whole book, it’s all of these interviews, 100+ interviews with the most successful people in the world and summing up all of their philosophies in that one sentence, which is pretty amazing.

Andrew: Yeah.

Chris: How has that worked for you?

Andrew: I think there was a period there where I believed that I was going to be a millionaire or that I believed that I was going to and all I cared about at the time was money. I didn’t even care about a legacy.

So, it didn’t–when someone offered me $1 million for something–I specifically remember the person. I’m not going to say what it is because I don’t want to embarrass her. I said, “I think you need to give me $2 million.” I still in my head believed that I had this sense of greatness. So, because I believed it, I wasn’t flattered to be offered $1 million. I wasn’t happy that that’s all you should get. I said, “I think I’m entitled to more out of this life.” So, that’s where it came up.

Chris: Did she give you $2 million?

Andrew: Yeah. I have a copy of the check somewhere. Actually, I lost the check because I decided to go and disappear from the world from a bit, but someone else at the team at the company I worked with, one of our employees had a copy of all the checks. So, I got a copy of it a few years ago.

Chris: Gotcha. With your company with your brother, I read somewhere where you basically burnt out and then sold out. Does that . . .

Andrew: Yeah. I tend to do things all the way until I burn out.

Chris: So, what happened?

Andrew: I just didn’t love it anymore. I felt like I couldn’t be creative, actually. That’s the thing. I couldn’t come up with creative solutions. That’s when I felt stuck and I felt like everyone else was enjoying their lives and I wasn’t.

I remember this one guy specifically said he sold his company and now he’s going to enjoy putting his feet in the beach of Marina del Rey. And I had never been to that part of the country, but the idea that this guy was going to put his feet in the sands of Marina del Rey after he just started his business not too long ago, I thought, “Why does that guy get to do it and I don’t get to do it? Why am I not getting to relax a little bit?” So, that set me off on a different course.

Marina del Rey does not have the best beaches, by the way. He must like have said that because he was going back to his mom’s house or something and maybe she had a beach house in Marina del Rey. Even though the specifics of it weren’t right for me, the idea was exactly what I needed.

Chris: What did that set off?

Andrew: A long period of just going and losing myself. A lot of people just never find themselves in life. I found myself really early. I knew who I was. I knew what I wanted. I knew I wanted to be an entrepreneur. I knew I cared about certain things. I needed to lose all that. I needed to go and let life carry me for a little bit.

I remember one example of that was I was out with these two girls and we were having a good time and we stayed out so late and they said, “Why don’t you just sleep on the floor of our house?” Now, the past me would have said, “I don’t sleep on floors. I need the best bed out there. Let’s go find the best hotel,” or would have said, “They think so little of me that they don’t even want to sleep with me. They want me to sleep on their floor.”

What I needed to do was be the person who I became, which is the person who said, “Yeah, let me try it. Let’s hang out and see what happens.” I ended up with a really good bonded, close friendship that lasted and still does for years. It’s partially because I’m just willing to go along and experiment and see where life goes. That’s not fully me. I’m not the sleep on the floor person. I really aspire to do more. But now I like that I could do whatever I need.

Chris: It was really just breaking out of that shell or I guess even a rut that you might have been?

Andrew: Yeah, there was a bit of a rut. I needed to learn how to relate to people outside of business. I could talk to you about selling to you. I didn’t know how to talk to you just to talk to you. I needed to figure it out. To actually get together with people and to care about them, you have to lose a lot of your hang-ups.

Chris: Yeah. It’s so much with the ego in terms of being able to listen, which I guess became very important to what you decided to do with Mixergy. Where did that come from and how do you go from where you were to saying, “I want to start interviewing lots of people?” What was that like?

Andrew: There was this great A&E “Biography” of Andrew Carnegie. There’s a bunch that’s fantastic about it. I remember watching it and seeing all the other people in the rich series ended up with kids who basically lost their money and had sad lives, like the Vanderbilts were a good example of sad lives or the Gettys, horrible lives even though they kept their money.

But the Carnegie kids and grandkids ended up with really happy lives and largely it’s because he decided to give away his money and force them to find their own lives and make their own way in the world. So, I took that from it. I also just took his determination and ambition. This was a guy who came to the US from Scotland with nothing. His dad couldn’t hack it here and basically wished he couldn’t come here because he was a failure here.

But Andrew Carnegie as a kid started out shoveling coal and then built up this business, became a railroad guy, then became the prince of steel, they called him, then sold his company and became the richest man in the country.

But the thing that stuck out for me about him was someone found an old desk of his and in the drawer, he had his next big goal for his life. It was something like, “In the next five years, I will give up this business and devote my life to reading and writing.” He expressed it in a very childlike way, but you understood within the context what he wanted to do was be in the world of ideas, of learning from other people and be in the world of sharing his ideas with the rest of the world.

When his family found it, I think in that documentary they said he never got to do that. I realized I always postponed that too. I always postponed having love in my life and I always postponed leaving a legacy. So, when I hung out after that company and just went out dating and was willing to sleep on someone’s floor, I discovered how to like people and love them so I could love them too. Since them I had gotten married.

I also always postponed leaving a legacy. Like Andrew Carnegie’s Carnegie Steel is gone. You can’t look up Carnegie Steel and go look at their factory. But years, decades after Andrew Carnegie died, Warren Buffett gave one of Andrew Carnegie’s books to Bill Gates to talk to him about where he saw philanthropy in the future and in their lives.

As a result of that and other similar ideas, the two of them decided to give up their fortunes and have deep impact of the world for the good. It’s because he spent a little bit of time thinking about what legacy he wanted to leave, a little bit of time leaving his ideas behind. And he never got to complete that. He never got to really spend time on that. He spent more time golfing than he did with that because he postponed it for too late.

So, that’s a long way of me saying that’s when I decided that’s what I wanted to do with this part of my life. I want to stop and actually leave a legacy of ideas. The way I’m doing it is through interviews. I believe very deeply that 100 years from now there will be someone listening to my interviews and learning from these entrepreneurs and learning from the way that business was done in the early part of the internet. I think that person will be changed dramatically because of these interviews.

I know for many people that sounds silly. They think everything is going to disappear. We’re living in a world of very disposable ideas. Everybody’s blogging, lots of content, I get all that. But Johnny Carson had this same belief in his content. The guy was just a comedian. In a world where all the stuff was so disposable, some of the material back then literally was deleted, like they’d use the film to create new shows on top of, but not only did he believe so much in his stuff that he decided to own his material, he to his day has all of his old shows in what is it, a salt mine in Nevada because the salt will keep the air from causing damage to the film.

That’s how much he wants to preserve his stuff for all time because he believes that his jokes will outlast him. There are a lot of times you see the lost episode of something, “The Honeymooners,” or the lost episode of Howard Stern, a guy who also has a lot of self-appreciation. You don’t see the lost Johnny Carson. He made sure you will not lose any of it. He saved it. You still see Johnny Carson on YouTube, on Twitter. I saw it just yesterday on John Gruber’s Twitter account. That’s the way I see my stuff, lasting beyond my life, having more impact than comedy ever could. Comedy will not hold up, business will.

Chris: So, how did you decide, “I’m going to start interviewing people?” What was that progression? Was that just like a lightning bolt?

Andrew: I just started doing interviews on my site as like side content, just an exploration and then I discovered it. I think anyone who’s listening to us who hasn’t thought about, “How do I leave a legacy?” is really robbing themselves of today. You do it for the legacy and you end up having dramatic impact today on people.

Chris: What does that mean to you? I think for a lot of people when they hear that–I could be wrong, but they think, “I’m not known all over the world,” or, “I’m not super rich.” What does that mean to you when you think about leaving a legacy? I know you just kind of explained it in terms of 100 years from now. But for somebody else out there, why would you encourage them to really think about that?

Andrew: I could get excited about bots recently, messaging bots. I wanted to try a software. A lot of it was just inaccessible because it was still beta. Some of it was kind of weird. There was this one that I really liked by a guy named Mikael. It was called ManyChat. I wanted a little bit more out of it than I was getting.

Because I do Mixergy, I was able to reach out to someone who knew him and get an introduction to him. Mikael, the creator, was a fan of Mixergy and was working with me and saw my issues, dealt with them, improved the software, helped me out, talked to me on a regular basis to give me a better experience. I gave him something through Mixergy and other people in the community through Mixergy. Now my life is impacted for the better.

I don’t just start at a blank slate when it comes to software. I don’t start at a blank slate when it comes to being in a new country. I literally was in wine country of Argentina, didn’t know anyone, wanted to go to this restaurant, couldn’t get to the restaurant, the guy happened to be a fan, heard I was in Argentina, invited me to his freaking house to look at his winery to have an asado with his family. I’m talking about that.

I don’t think you could just get that by being the person who just says, “Here’s this crazy thing that’s going on today,” and getting a lot of attention today. You could get it maybe for a minute, but you can’t get it in a meaningful way.

I think it’s kind of like running. I do long distance runs. You cannot finish a marathon if you say, “I wonder if I can even do a mile.” You have to get your mind not even to say, “I’m going to finish 26.2,” but in your mind to say, “I can do 30,” in your mind to say, “I can do 27.” I want to have so much impact today that I have to say, “I’m going to have 100 years of impact.”

Chris: It’s a really interesting way to think about it because many times when I hear somebody talk about their legacy, I think that’s where the legacy and you really just bring it more even to today. I’m thinking like from my daughters like what’s my legacy going to be for her, but it’s really interesting to think more in terms of right now what’s my legacy, what’s my reputation. Is that more what you mean?

Andrew: Yeah. I think we should be thinking long term. Maybe this is just me being nutty, but I want more and wanting more means I want it to happen after my death. Now, Mikael, the founder of ManyChat, he’s not doing this. So, you don’t know his software.

I went and did a lot of research to find other bot software, people aren’t writing about his bot software. They’re writing about the competition. They’re writing about Chatfuel. They’re writing about all these other apps. They’re writing about Maya because he’s not saying, “Here’s what I believe the future of bots are. Here’s what I believe the business should be like.” He’s not doing that and he’s missing out because of it. I think it’s not enough to just say, “Here’s where I think it is today. Go try my software.” You have to say,” Here’s the vision for the future.

Chris: Did you bring that up to him?

Andrew: I did a little bit, but I don’t want to tell people in person who they should live their lives. I don’t want to be like Larry Sanders. Every episode he thinks that everybody from the receptionist to the dentist office to the people at HBO need to listen to him and redo their business like him.

Chris: Larry David.

Andrew: That’s a good show. Larry David, right? What did I say, Larry Sanders?

Chris: Garry Shandling.

Andrew: Different show, great show too.

Chris: Yeah, that was another good one. So, Mixergy starts off and you start interviewing people on the side. What’s the progression? That’s 2004. One of the things I think of with Mixergy is the idea, Jim Rohn’s quote, “You’re the average of the five people you’re around the most.”

Andrew: Yeah.

Chris: How much of that were you trying to increase your average a little bit came into that?

Andrew: I definitely get that. I didn’t think of that, but I get that because of this.

Chris: So, 2004, you start doing that.

Andrew: Actually, it started sometime like 2009, I think. I never really was clear about it, but 2004 maybe when–no, Mixergy started as a company, 2006. I know I looked it up today. I was at the bank.

Here’s a weird thing, by the way. I went to the bank and said, “I need $500.” I want to dramatize something. So, they gave me 500 crisp dollar bills. That’s not the weird thing. The weird thing about it is I said, “I don’t keep the ATM. You guys give me an ATM. I never need cash. I just rip it up. I cut it and I toss it in the garbage.” They said, “Okay.”

I said, “I don’t have ID that shows my name. I changed my name to Andrew Warner. So, that’s what I use for work and that’s what you guys set me up with on the account. So, I have my driver’s license but it doesn’t say Warner as my last name.” And the guy said, “Okay. What’s the tax ID number?” I shouldn’t be saying this. Based on the tax ID number and the fact that he’d seen me in the bank a few times, he just said okay. I never needed my account with him. He said, “Okay,” and he just gave me $500. Is that something?

Chris: It’s amazing. I do a lot of these experiments around New York City and actually around everywhere to see what people will let me do based on just sounding like I know what I’m talking about. You get away with–

Andrew: I think that’s exactly it. If you act like you deserve it and you know what you’re talking about, they’ll find a way. They’ll just assume that’s what it is.

Chris: I’ve rented cars with no license.

Andrew: I’m not supposed to get into this building. Sorry?

Chris: Exactly.

Andrew: I’ll give you another one. I’m not supposed to get into this building without ID. I have scotch night in the office a lot. When someone doesn’t have ID, they often will get stuck downstairs. They especially check for ID in the morning. I hate carrying another thing with me. One day I said, “I’m going to take a picture of my ID for the building and I’m just going to show them the picture on the phone so I don’t have to carry it. Let’s see what happened.” I couldn’t keep myself from smiling. But I showed it and they let me through. I could Photoshop that freaking thing.

Chris: Yeah. I think so much of it is just about the way that you come across and it sounds like–I do the same thing with security here. I never have a license on me or anything because I live in New York. I don’t need one. I’ve never been turned away. I’m not saying that in a bragging way.

Andrew: I’m going to do this because what do I have to lose here. I’ve actually been robbed in the office before. I have a really nice office and still someone stole my Social Security card, activated a credit card with it. It was bad, but it wasn’t the end of the world, so I’m comfortable saying this. If anyone comes here for scotch or for a meeting with me, it’s 201 Mission Street, 12th floor, strut right past reception like you own the place and walk upstairs.

The reason I could say this if you want to experiment is that if you fail, all you have to do is call me and I will let you in the building. I will come back down and say it’s fine. You can experiment, but if you walk through with confidence, they’ll just let you do it. If you assume something, they let you have it. Anyway, that’s kind of a sidetrack and I think I’ve just helped people get into the building.

Chris: It’s all about experiments. So, how do you wind up where you are today?

Andrew: I loved the interviews. I loved the interaction that I had with people. There was woman, Rosalind Resnick, who I worked with for years. She bought a significant piece of our business when I was done. I interviewed her. I realized I had known her a lot but I didn’t know her nearly as well as when I could just have an interview with her and say, “Where did your idea come from? What was it like? Did you know what you were doing? What was it like when you took your company public?”

That whole thing was just exciting for me because I loved success stories and also it showed me I could get to know the people in my life better. I realized if I do an interview and no one listens and I get to talk to people I care about in this way, I’m good. I had dinners with Rosalind for a long time, for years. We’d had meetings. We talked on the phone and I didn’t get to know this stuff about her. This is a way better way to get to know people.

Chris: I read somewhere where you talked about that one of the big turning points came from a conversation with Neil, our mutual friend Neil Patel, where you were a little bit or maybe very hesitant about sharing more personal information. Just walk me through that a little bit.

Andrew: Neil Patel said, “You should be talking more about yourself.” And other people had too. I thought, “No, I’m an interviewer. I’m supposed to be talking about my guests. It shouldn’t be about me.” Neil really pushed me. He said, “You ran this company. I know what your revenues were.” I don’t remember how he knew it. He said, “Let me see it.” I said, “What do you mean?” He goes, “You said audited financials.” I said, “Yeah, I had it audited by Ernst & Young. I paid them like $20,000 for it.”

He said, “Let me see it. Let me show it.” I said, “No. No one cares.” I said, “All right, Neil, I trust you. I know you. Here’s a copy of it.” I handed it to him and he published it on his site and I think to this day you can still see it on his blog, QuickSprout. I think that it opened me up to talk more about myself because it natural brought up questions about how did you do it, what else did you do.

And the more I talked about myself, the more I realized that people do care. I don’t want to be someone who only talks about himself, but I do need to remember to talk more about what’s going on in my life, I think even to the point where it’s a little bit off. Once I started doing interviews, I went back to read about Johnny Carson. He might be the most successful showman in all of television, maybe, maybe actually since then, of his time, for sure. But he owned his show. He made tons of money.

There was this piece there about how Ed McMahon started talking about his weekend and his family and showing photos and Johnny Carson was listening and then said, “Okay, now stop boring me. We have a show to do. What are you doing telling me about your family?”

And the author said Johnny Carson was smart enough that of course people need to know who his sidekick his, a little bit about the sidekick’s life to care, to have something emotionally invested. That’s why he brought it up. Then he knew also to cut it off. I realized I need to do that too. I think everyone listening to us needs to also think more about how can I talk about my life, the personal stuff that I don’t think people care about, but frankly we all do.

Chris: Was that uncomfortable at first?

Andrew: It was very uncomfortable, very. I actually thought after that I would get kidnapped. I think we were going to Argentina, but those kinds of thoughts came in my head. But frankly, there are way bigger fish to go after than me. Second, I thought people would just be bored and not care. They weren’t. They care. They care more. We care about people like that. I care about what someone’s house looks like, frankly. There’s no substantive reason for me to care about it.

Chris: What about the flip side of that in terms of sharing the times when things didn’t go right or the failures. Is that something or do you focus more on the other things?

Andrew: I do. I care about that too. I think that it humanizes us. One of the people I really admired was Dale Carnegie because he wrote about how to influence people, “How to Win Friends and Influence People.” I went and knocked on Dale Carnegie & Associates’ office. I got an internship working for them. I said, “I just want to work for you to do anything for free,” and they gave me a job.

One of the things I learned there was if you want to tell someone they’re wrong, you should start by saying what you did wrong. So, if I wanted to say to you, “you didn’t tee up this question right,” it would be so much more effective if I said, “Chris, when I started, I remember asking a question and the person just looked at me. He just said, “Okay.” And I said, “Yeah, so?” And he goes, “So what? What’s the question?” I realized I didn’t ask a question. I just went long-winded. That’s when I knew I have to be more directed in an interview than I would in a conversation.

I noticed you doing that a little bit where you didn’t ask me a question and that’s why I was stalling. This is not true in our conversation, but if I wanted to tell you if you weren’t being clear, it would be more helpful if I pointed to myself and said how I didn’t do it. People are much more receptive that way. Same thing is true in interviews, same thing is true when you’re running a company. You want to be able to show a little bit of vulnerability so people don’t become defensive. They care about you.

Chris: Gotcha. I’m trying to be very clear about all of my questions from now on.

Andrew: I wish I had a better example of something you actually had done and I could bring it up.

Chris: That’s perfect. The funny thing about this show is it’s called Deconstructing Success. Where this really started from was over three years ago when a company I had failed.

Andrew: What happened with that? I’ve got to interview you about that at some point. Why did that company fail?

Chris: We wouldn’t have enough time to go through everything right now, but I will certainly. . .

Andrew: You’ll be open about it.

Chris: Of course.

Andrew: You had cofounder issues.

Chris: We had a lot of issues.

Andrew: Will you talk about cofounder issues?

Chris: Sure.

Andrew: Okay. Will you get on with your cofounders on a conversation with me and one or two of your cofounders or do you guys hate each other that much?

Chris: I don’t think that’s going to happen.

Andrew: Because you guys can’t talk to each other at this point.

Chris: Yeah.

Andrew: Wow. I can see you tensing up. Your throat just tensed up when you said yeah.

Chris: Yeah. That’s a whole other story.

Andrew: Okay.

Chris: But actually that’s a part of so many different stories in how I’m able to help relate to other people because you bring that up and they’re like, “I had the same exact thing.” So, let’s shift a little bit to over 1,000–and not shift because of that–but you’ve interviewed over 1,000 different entrepreneurs. What I’m really curious about is taking a few of them or a bunch of them–I handpicked a good mix–

Andrew: Oh, you pulled out a few? Good.

Chris: Oh yeah. So, I just want to hear something, a lesson, a takeaway, anything. This will be part test for you that you learn from them. Let’s start with Seth Godin, bestselling author, one of the probably greatest marketing minds alive.

Andrew: The one thing that I got from him was how to build a tribe. He said to just focus on your message and then wait for the tribe to come. At the time, I was too much focused on my analytics and why my numbers were pretty junky. I kept seeing people with tens of thousands of hits a day and thinking, “Why am I even doing this when I can’t get 100 people to come to my site a day?”

So, he told me the story of Barack Obama starting out running for president and the only person who was with him in the car was this one photographer who ended up writing a piece about the experience in The New York Times and there was no one following him. There were no crowds, no nothing.

Then eventually in that campaign, there were crowds of people and people were fainting and he became this celebrity to the point where I think he was running against McCain at the time and McCain said, “Do you want to hire a celebrity to be your president or someone who actually has the experience?” He started out with his one person following him.

So, it took my eye off of analytics a little bit and got me to focus back on what my message is. You can actually after Seth Godin’s interview see me come back and focus on the message. I think we should all take a step back and get to that, like what are we here to do? And take our eyes off the analytics a little bit.

I’ll give you one other example. Mike McDerment of FreshBooks bootstrapped it. I asked him, “When you weren’t making money with this, how did you get by?” He took his eye off analytics for a bit and he said, “The way I measured success was how people said thank you in email. If they really appreciated it, then I knew I was on the right track.” So, he went back to making it matter for people instead of being upset that he didn’t have as much revenue as others.”

Chris: The other good point from the Seth Godin interview is how well he can tell a story to make a point. So, using that Obama story rather than just–

Andrew: Yeah.

Chris: It’s such a good point, I think.

Andrew: I never thought of that, but he really is so good at that.

Chris: He’ll pull out any seemingly random story that makes perfect sense. Barbara Corcoran, “Shark Tank,” Corcoran Realty?

Andrew: I love how she flirted with me, not because I needed the emotional pickup from that, but because I realized the pros are so good at doing interviews. It’s so much easier to interview someone who’s a pro, pro storyteller, pro showman, pro television star.

She was so easy to interview. I realized at that point that if I was interviewing entrepreneurs and getting them to tell stories and getting them to be interesting, then it was like running with a 50 pound vest on and I think if I ever got to do interviews with more experienced celebrities, it would be like taking that 50 pound vest off and having someone help me for the run.

So, it was a real good indication that it’s not just about how good an interviewer I am, but also how good is the person I’m interviewing. If I’m doing this well without a lot of celebrities that when I get people who are experienced, I can really kick butt.

Chris: Kathryn Minshew from The Muse?

Andrew: The thing that stood out for me was I never heard of The Muse. I wouldn’t have even interviewed her about The Muse. What the hell is The Muse? Then I started doing research and realized the revenue this business had, realized the strength, the size of it, it really humbled me. There are so many businesses out there that we don’t know how big they are. This one was right there, I should have known. I should have known because it was public. There are so many private companies that we just don’t know about.

Chris: I love that. Brian Chesky, Airbnb, the exact opposite where you knew about them?

Andrew: There are a few things. I didn’t, actually. I turned him down. I have emails where I turned him down. But he was a fan and he kept saying, “No, I should be on.” This was him just getting going. What was cool about him was he didn’t just say, “Andrew, I need to be on. You should have me on.” I’m pretty shocked too. He said, “Here’s what I can teach your audience,” and was really clear about what he could bring, really clear. He didn’t just say, “Come on, you should.” He said, “Here’s what I can bring.”

I still have that email. That shows so much about how he works, that he says, “I know what your need is and I’m not going to push my need. I’m going to show you how giving me what I want gets you–the best entrepreneurs I’ve interviewed are just like that. They’re so good at that. I should find that email.

Chris: Please do. Jason Fried, you mentioned before, from Basecamp, 37signals?

Andrew: There are two things that stand out for him. The first, no one knows this, no one would have noticed it but to me it’s really big–at one point when I interviewed him, he said, “Don’t you think what you’re doing is good?” I said, “No, this is so junky compared to where I want to be.” I saw this look of disappointment on his face. I always wanted to talk to him about that, but it’s been so long there’s no way he could remember.

But it stuck with me that he sensed that I wasn’t appreciating what I was doing enough. In my head I’d sometimes argue with him over the years and I say, “Jason, you don’t understand. Here’s the big thing I want to do,” and of course this is tiny. I’m just doing a small blog, a small podcast. But I also knew that’s not the right way to approach it. I mostly said, “What is he trying to say there?” I realized I didn’t appreciate what I had.

I see these little pissants with nothing going for them who really talk up what they have. They talk up their book, as they say on Wall Street, and it makes me appreciate what they have more and it makes what they have more powerful. Here I was with something really powerful. Brian Chesky, the Airbnb founder is trying to get on because he appreciates it and I don’t appreciate it. I had to take a step back and say you have these grand ambitions, but here’s a thing. I leave it at that, actually. There’s so much more I can say I learned from Jason.

Chris: Salman Khan, Khan Academy?

Andrew: That he was in his closet and he was recording back then. Today he’s got this huge company, but he was in his closet. Again, I think if you’re in your closet, you’re still small-time, but he wasn’t. But then he was nonprofit. I say, “If you’re nonprofit, how much impact could you have?” But he had tons of impact. Then I think if you’re a nonprofit, you’re always going to have this boring approach. Look at what he’s got today. He’s got a real education business that’s not a business, but an education machine there that’s helping students in schools.

Chris: Leslie Bradshaw, JESS3?

Andrew: That I did a crappy interview with her. I think it was okay. I think what I didn’t get was that she and JESS3, Jesse, the cofounder of the company JESS3, that they were on the outs. I don’t think I fully got that in the interview. .It wasn’t until after I published the interview that I realized how much of an issue there was with Jesse, the cofounder.

I’d love to at some point explore that, even if it’s over drinks. Sometimes I regret that. Sometimes I feel like how could I have published it? There’s so much more that I’m missing. Someone who really knows them knows how much more I’m missing. I have to really work on myself with that.

Chris: Yeah because what about the majority of the people who have no clue and they got something what you did get from it.

Andrew: Yeah. And I also just can’t publish unless I’m okay with some of the stuff not being great.

Chris: Jimmy Wales, Wikipedia?

Andrew: So, Jimmy Wales was not that into me. I could tell he was packing while we were on the interview. At the time I was really grateful for it and I still am, but years later if someone did that to me, I would have taken it as a slight. I’m glad that with him I didn’t take it as a slight. I remember saying to him, “You guys intentionally made the editing box on your site hard to use so you could only have the smartest people use it.” He said something like, “That’s the stupidest thing anyone’s ever said to me,” something like that.

What he was saying was he just used what he had. He just used it. I think it’s a crappy box to this day, but it was especially horrible back then. They weren’t using HTML. They were using some weirdo thing. But it’s just what he had. Speaking of just publish with what you have and be proud of it, he was and he published it. He was proud of it and even years later when I put it down, he was proud enough to push back on me to slap me down. It’s a small thing that I don’t know a lot of people picked up on the interview, but I did and it meant a lot to me.

Chris: Ryan Hoover, Product Hunt?

Andrew: With Ryan, it was not so much what I saw in the interviews, but what I saw from him outside of the interviews, I think because he has this very childlike photo of himself online. Forever I thought of him as this teenager who was just goofing around looking for something, never taking anything seriously. But there was some stick-to-itiveness with him, some tenacity. Dammit, the guy found something that’s really big, that’s really successful now with Product Hunt.

It’s just impressive that an ordinary person like him–I can’t think of frankly in many ways, this might be an insult to him, but I don’t think it is, anyone more ordinary, more regular guy than him. Any kid out there who’s listening to us could be what Ryan Hoover was before he started Product Hunt.

But he was trying these different things, always from a place of real genuine curiosity and genuine expression and he created Product Hunt with this junky looking software. I’d call it junky, but I shouldn’t call it junky. It’s basic off the shelf software to share people’s favorite products in a world where I thought I had enough products.

Who needs more product discovery? But he found people who were diehard product sharers and he was authentic with them and as eager with them as he was with me and he created this community. I don’t know how much he raised from Andreessen Horowitz. It’s not about that for me. It’s that the best venture capital firm in the country, the ones willing to say what they mean believe in him and his ideas. I think that’s really interesting.

The other thing that stands out to me is I asked him, “Where are you going to get revenue from this business? Where’s the business?” I saw how disappointed that I would even ask it. You can see it on camera if you look. The other thing he said was if you get a lot of people who care about products coming to your site, of course you can monetize it.

I think that’s very much a Silicon Valley response and I’m still waiting to see how this show ends, where does he find that revenue or is this going to be another company saying, “I defer the business model to later and never getting it.” I don’t know. I think he’s smart enough to find it and I think Andreessen Horowitz is too. But I’m so eager to see how that plays out. And I’m addicted to his site every day.

Chris: A couple more, Laura Roeder? You interviewed her four times.

Andrew: Did I?

Chris: Yeah.

Andrew: Laura was someone who just–you know how when you go to a conference and you see someone so eager to be at the conference that they’ll raise their hands to participate and you think, “Come on, dude, don’t take yourself so seriously. This is just him presenting. What are you doing?” She’s the one who would do that, who did do that, who went to the front of the class and asked for feedback and took that feedback to heart.

And then she created a course that she did using nothing but screen capture software, screen flow and showed people how to do social media. She did well with that. That’s when I knew her. I didn’t know her back when she was at her go to the front of the class and get feedback from the conference leader. I knew that it played out. So, I could just really respect that she would do that.

Then she had this audience of people that she started building when she was selling ScreenFlow courses, courses she created using ScreenFlow software. She messaged them and said she had this new software she created. Now she’s got a really successful software company because she just–this is the ultimate bootstrap, using basic software, teaching. My first interview with her, she went into the how to of it. I think it’s really good and underappreciated.

Chris: One more, Gary Vaynerchuk?

Andrew: There’s so much I wish I asked Gary Vaynerchuk. My last most recent interview with him was good but there’s so much I wish I asked him. I hate living with that because I don’t know that I’ll ever get a chance to do it. I’ll tell you what always sticks in my mind with Gary. When he was a real hit, he was always supportive of me. He even did my live event for free knowing I was selling tickets to it.

But what stood out to me was after my first interview, I said to his assistant or someone on his team, I said, “If you need anything let me know and I can make the change.” His response was, “No, Andrew, you’re the pro. We trust you. You got this,” something like that. What blew my mind about that was this wasn’t Gary. This was someone else who worked with him, that he was so good that even the people around him had Gary energy in him.

I tend to be a cynical person. I think a lot of people are bullshit artists. So, I don’t believe in what many people say. So, I would have been skeptical about a lot of the people who are on Mixergy, except when I interview them and get to know some of them after the fact. I get to see what they’re really like and it’s so heartening to see it match up.

Chris: What do the most successful people have in common? Have you noticed any traits?

Andrew: Empathy. Empathy is the number one thing, most underrated. Empathy, by far. If you could acquire one thing, it wouldn’t be the tenacity of Napoleon Hill, it would be empathy. Here’s what I mean by that. The guy who worked with Gary Vaynerchuk empathized with me and knew that I felt a little bit like grateful to have Gary on and the team and understood how I felt and he reflected it back and made me feel good about myself.

You talk about Brian Chesky. He had empathy. When he tried to be on Mixergy, he empathized with me to get what he wanted. He also empathized with his users. He told me famously how he flew to New York because that’s where the majority of his customers were and he stayed in their homes and he got to know them. One of the people there said, “It’s nice you let me rent out the floor of my house or spare bedroom, but really, I want to rent out the whole place when I’m tour with this band I play with.”

He had to empathize in order to pick up on that, to care to ask about that and then to find a solution within the software and he did. He said, “We’re not going to be about air mattress and breakfast,” that’s what it was, air mattress and breakfast, I think. “We’re going to be about a whole place.” So, they started actually going beyond the air mattress in your house and letting you put up your whole house.

Empathy, empathy, empathy–it’s the number one thing and it’s so hard. One of the challenges with it is that when we’re in business, I think coming on here, how do I do a good job so I don’t look like a failure here? I think, “How do I make sure that I come across as charismatic as I am in private or as I’d like to be or as the people who I interview?”

It’s really hard to take a step away from that and put that need aside and to say, “First of all, what is Chris looking for? How do I do a good job for Chris?” Not how do I do a good job of Chris, that comes back to me, but what is Chris looking for. What is he about? And then take it one step removed and say the person who’s listening to what Chris is recording, how do I know them? How do I care about them? What do I do to let that person into my mind, into my heart a little bit?

It’s really hard. The good people do that. Like Brian knew how to do that. He didn’t just say, “What does Andrew want?” But, “What does Andrew want and what do his listeners need? What do they want?”

Chris: Is that something that people can learn?

Andrew: I think so. I think you can follow in the footsteps of some of the people who have been empathic. Look at Brian. He lived in his customers’ lives. You say okay, Brian is a guy who lived in his customers’ lives because he had an Airbnb company. That’s what his company was.

I interviewed someone who was an info marketer who literally went and stayed at his customers’ homes. You could hear me in the interview saying, “Why’d you stay in their home? Are you too poor to afford a hotel? Maybe this whole thing is a scam.” He said, “No, Andrew, I went to their homes and I saw what they were really like. I understood how they absorbed information.” I said, “Give me an example.”

This was a few years, but not too long ago. He said, “I went to their homes and I saw they had on display in their bookcase CDs from courses they bought. They wanted those little things, those little physical things I don’t care about because I’m a digital person. I want as few things in my life as possible.” By living with them he got to understand that.

I want to do as much of that as possible. There was someone who earlier today was supposed to get on a call with me to just get feedback from me who backed out because he said he didn’t want to waste my time and things aren’t going badly for him, so why bother me. He doesn’t understand that’s not a bother for me. This is my way of getting into his life. I’m not physically living in his house and his bedroom, but I’m emotionally living in his problems when I get on a call with him.

Yes, I’m doing him a favor by hearing out his problems, letting him think it through out loud, giving him feedback, but I’m doing myself a much bigger service by understanding what he is like and empathizing with it so I can express those problems in my interviews and allow my interviewees to address those problems, to create a product that actually doesn’t just entertain, but solves people’s problems because it starts by empathizing with them. So, the number one thing by far is empathy.

Chris: You brought up with that guy and that’s really like an invisible script, saying that I’m wasting this person’s time. How do you overcome those types of things for yourself?

Andrew: In myself?

Chris: Yeah.

Andrew: One of the people in my audience is a guy named Troy Dean came to the US from Australia with his wife. I know what wives are like on these situations. My wife, whenever she does anything business with me, everyone ignores my wife. They don’t even ask her name. So, I wanted to take an interest. She turned out to be a therapist, worked with people who had deep problems. They think literally people are out to get them, like she is out to kill them.

And I said, “How do you solve that when the voices in their heads are saying that to them?” She said, “You solve it by not battling with them, by not saying no. No one here in the hospital wants to kill you. You solve it not by dismissing it and talking about the weather. You solve it by asking about it, by giving them some room to vent it. Then you address the world as they have it and then you try to give them another perspective.”

So, coming back to this, I think the first thing we want to do is you call it invisible script, I call it countermind thoughts, these thoughts that just counter everything we want to do, they’re in our own heads. I think the first thing we want to do is what she does with her patients and just bring it out, just bring it out. What is it that is going on?

So, if this guy would have asked himself why not and been a little open with himself, he would have realized that he’s a little intimidated. He’s a little afraid to talk to me. He’s worried he’s not important enough, not ready yet to have a conversation with me. I think that would have allowed him to say, “Wait a minute, I’m not ready? Of course I am. This is what Andrew does. Of course I am, I’m a customer of Andrew’s.” Then we can start to deal with it. But we have to recognize it and we have to acknowledge it.

Chris: How do you deal with information overload? You interview all these people, you read all these books, questions. How do you know what to take action on?

Andrew: Remember the story I just told you about Seth Godin and how Seth Godin told me the story of Barack Obama? I didn’t take notes about that. You didn’t take notes about it. Our listeners didn’t take notes about it. I bet you they remembered that and they remembered the point of it and it sticks in their heads.

One of the best things that I got out of going to work for Dale Carnegie is people think of it as the “How to Win Friends and Influence People” company. They actually and Dale Carnegie, from the time he started to today, long after he’s dead, they teach public speaking first and the things they ask you to speak about are how you related to people using some of the ideas that Dale Carnegie came up with.

One of the things I learned was they only give you two minutes to speak and they force you to tell a story so you won’t have to have a script with you and it sticks in people’s heads. So, when I interview a guest, I intentionally ask them for stories. Seth Godin is an easy one to get a story from, but every single guest who came on Mixergy has been worked with by me or someone else on the site to get their stories, to not just get the facts, not get the lesson, but get the story because if we tell a story with a compelling useful point to it, my audience won’t have to worry about information overload. They won’t have to take notes. The story will be embedded in their heads.

I guarantee you, a person who’s listening to me will test it out, five years from now, when you think to yourself, “How do I get a tribe when no one is even watching my stuff? I can’t even get 100 people. I can’t get one person.” I guarantee you you will remember the story I just shared with you from Seth Godin. I guarantee you the stuff will stick with you. That’s how you deal with information overload. You look for stories that are meaningful and compelling and have a point that’s worth remembering.

Chris: Perfect. Last question–what’s the best piece of advice you’ve ever received?

Andrew: It’s not even for me. I don’t have a best, but I have one that stuck with me a lot over the years, especially as I go public with my ideas, with my site, with my interviews. It was what’s that one with the guy from This American Life?

Chris: Oh, Ira Glass?

Andrew: Ira Glass, thank you. There’s a piece in front of his editing deck and he’s talking about how when we get into this business, we do it because we have taste. That’s why we want to do more of it. We have a certain aesthetic, certain message we want to get out there. We start producing and our first stuff stinks. It doesn’t live up to our taste, the taste that drew us to this. We think we’re pretty junky and we want to give up at that point. What we have to do is stick with it until our abilities live up to our taste.

Forever, whenever I want to publish something or say something, the only reason I’m speaking to you is there are people whose ideas I really respected and admired. I can’t when I started speaking live up to their best of tapes that are in my head. I have to just remember I have to keep doing it until I get as good as I can be, as good as they were and then even better. So, that’s the thing that stuck with me. That little bit of video was really useful.

Chris: I love it. Where can people go to learn more about you?

Andrew: I think the best way to do it is to go to the iTunes Store or the podcast store in Android and sign up right there. Then you can go in, subscribe, listen to my interviews. Some of them you’ll love, will have impact on you for the next five, ten, fifteen years, you’ll share with your kids and the messages will part of your family and your company’s culture. Some you’ll hate. The reason I encourage people to subscribe is so if you don’t like one, you’d feel comfortable moving on to the next until you find one you like.

Chris: So, go to the store and type in Mixergy, correct?

Andrew: Yeah, Mixergy.

Chris: All right. Perfect. Thank you.

Andrew: What was that?

Chris: Lightning.

Andrew: You guys have lightning in New York now?

Chris: Thunder. I guess it’s finally about to rain. Andrew, thank you so much for spending time with me and thank you for sharing all this.

Andrew: Thanks for having me on.

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