Sherry Walling of ZenFounder interviews me about my mental health and inner entrepreneur

I usually interview entrepreneurs about how they built their businesses but today I have something a little different.

If you’re an entrepreneur who wants to understand the inner entrepreneur, this will be a good interview. In this episode Sherry Walling, a clinical psychologist, interviews me for her podcast ZenFounder.

We talk about my mental health and happiness, what motivates me, how I grew up, and why I am the person I am.

ZenFounder is a podcast where Sherry talks about startup family life: how to work well, how to stay healthy, and how to be in relationships that are healthy and happy.

Sherry Walling

Sherry Walling


Sherry Walling is a clinical psychologist and creator of ZenFounder, a podcast where she talks about startup family life: how to work well, how to stay healthy, and how to be in relationships that are healthy and happy.


Full Interview Transcript

Andrew: Hey, everyone. My name is Andrew Warner. I’m the founder of Mixergy. You know that I usually interview entrepreneurs about how they built their businesses. But just a few minutes ago, Sherry Walling finished an interview of me. She interviewed me for her podcast, which is called ZenFounder. Do I have that right?

Sherry: Absolutely. Yeah.

Andrew: I just lost my notes. I don’t know what I tapped on my phone, but all my notes disappeared, which is fine. Sherry Walling is a clinical psychologist, and she has a podcast where she talks about the … I was going to say you talk about the inner entrepreneur, the mind of an entrepreneur, but you do more than that. Sometimes you get a little tactical about running a business and running a life, right?

Sherry: Yeah. We try to talk about startup family life, so how to work well, how to stay healthy, how to be related, how to be in relationships that are healthy and happy.

Andrew: So you did an interview with me where you talked to me about my mental health and happiness and understanding why I grew up and why I am the person I am. I thought, “That was such an interesting interview. Are you going to publish the whole thing?” Like a pro, you said, “No, I actually edit the stuff down. I only want the good pieces, and I want it to make sense.” And I thought I like that you’re a pro, but I’d like to go raw. I want no pro. I don’t want you to edit out the fact that I said I want to fuck more.

Sherry: That you want more sex.

Andrew: Yeah. I’m a little embarrassed that I just introduced it that way. Anyone who listens to this in the interview will realize I said it because I was confident and I was going to be saying it, and then I also backed off of it as a little bit intimidated by that. But I liked that you got me to places where I felt a little bit excited and willing to open up and also a little bit raw and a little wondering whether I’d gone too far.

I think that if you’re out there listening to me and you’re an entrepreneur and you want to understand the inner entrepreneur, this is a good interview where Sherry just got into how I got here, what my motivation is, what keeps me going. If you’re someone who’s just been listening to my interviews for years and you’ve heard me talk to other entrepreneurs and you say, “Who is this guy?” I think this is going to give you a trip into who is this guy. Sherry’s really good at that.

I’ve known about your work for a long time, and I really admire how you’re willing to get to that with your interviews on ZenFounder. I appreciate you saying, “Hey, Andrew, take the whole raw thing, post it on Mixergy.” If anyone wants this interview in an edited format or wants to just listen to other entrepreneurs, including one person who she just told me cried in her podcast. I’ve never got anyone to cry in mine, but I also don’t have your warmth. I have much more of my raw, New York aggression, which no one is going to cry from.

Sherry: You make people afraid, maybe.

Andrew: I do believe that. Even as a kid I kind of intimidated adults, because there was like this steely determination. I don’t know what else is there. I think it’s going to come out in this interview. So, guys, this is a role reversal where I’ll be interviewed. I really think it’s so good that I’m proud to have it up here on Mixergy, and I appreciate Sherry letting us do it. If you want the more edited version or want to actually listen to other entrepreneurs go through Sherry’s get you open process, more of a therapy session than an interview session, I really recommend that you check out her podcast, ZenFounder. All right. Here we go.

Actually, one other thing before we get started. My sponsors are counting on me telling you that this interview is sponsored by the company that will help you hire great developers and designers. It’s called Toptal. And by the company that will help you sell more, it’s called Pipedrive, but I’ll tell you more about those later on in the interview. All right. Now, officially, let’s start.

Sherry: I think my first question for you … I mean you essentially at this point make a living by helping people tell their stories. I guess I wonder why you think personal stories are so important. You’ve spent so many hours interviewing people. Why does that matter?

Andrew: My parents always had people over to the house Friday nights, Saturday nights, Sunday nights. They’d do cards for friends. I hated their friends. They weren’t bad people. They were just annoying people. They would have dinner conversations around food instead of interesting topics that I was curious about. They would do the same old jokes about, “So how’s your girlfriend?” when I was 11 years old. It was just like that’s not the life for me.

As soon as I could escape the table, I would go downstairs into the basement that wasn’t even finished or anything and I would sit on a folding chair in the middle of an empty room and I would read books. At one point, I discovered business biographies. Until then, I kind of had this entrepreneurial instinct, but I didn’t fully know. Then I discovered business biographies, and I started to see the world of possibilities.

I started to see that Malcolm Forbes used to get in freaking hot air balloons, cross the country and set records for the fastest way to cross, and you’d read these stories about guys like him who would do that. Was he gay or wasn’t he gay? Was he gay and kind of living his life but also being heterosexual? Nobody knew. Here’s the thing. He kind of I was going to say thumbed his nose at the world, but maybe he gave the finger to what you thought about it.

He used to cross the country, as I said, in the fastest balloon possible. But he had this train of people, essentially, following him on the ground and in the air, and people would say, “Hey, it’s unfair. You’re basically using your money to beat everyone else.” He said, “Yes, that’s the point of my magazine. You can do anything you want in business. It opens up these doors. We’re not limited in your rules.”

So I would read these stories of people who were really living their lives and knowing that upstairs from me was a room full of people who were going to ask the same question about whether I liked my rice green or yellow with vegetables or with a little extra oil and butter. This is not my life, the upstairs. This life of stories, this is what I want.

It opened me up to all kinds of ideas, opened me up to saying when I graduated from school, I don’t have to get a job. I could just be an entrepreneur right away. I know that it’s weird to go through college, to aim for grades and I did. I graduated magna cum laude or summa cum laude, whichever laude is the highest.

Sherry: The best laude.

Andrew: What is it?

Sherry: The best laude.

Andrew: Yeah, the best laude. I had the most laude. I’m not too embarrassed to admit that I had to go to Professor — I forget her name — and say, “Look, you gave me a B+. An A- would get me over that hump and I’d get the most laude. Would you do it?” and negotiated with her until she finally said yes. I’m not too proud to admit that it took me a lot to get that. But I didn’t want to use it. You can’t use it as an entrepreneur. No one’s going to buy from me. No one’s going to work for me because I had more laude than they did. So I still said this is a weird thing to do. It seems a little dangerous, but I’m coming from a perspective where it’s not dangerous and I’m going to start a company.

When you get exposed to stories like that, they dig inside of you. They become a part of who you are. I know I do interviews with entrepreneurs and a lot of people take notes. I like that they take notes. I’m a notetaker too. But I think they’d be surprised by how the structure of the stories that we tell by storytelling in general, how much it just sticks to you and you can’t get rid of it.

So they don’t have to worry about the message sticking with them. They just will come through the way that stories about Malcolm Forbes, the way the stories about his father, B.C. Forbes, who in many ways was more interesting and tons of other entrepreneurs stuck with me.

Sherry: So those early entrepreneur stories were the contrast to the boring dinner parties that your parents had and you wanted to live in those stories.

Andrew: Yeah.

Sherry: It sounds like you are living in that story, but you also are telling that story over and over with different entrepreneurs, different conversations.

Andrew: I am. Yeah. It’s also my way of learning. I bought the CDs that Tony Robbins used to sell on infomercials and I listened to them. He has all these assignments in them. I don’t know that I ever finished all 30 CDs, but I got pretty far with them. Frankly, they didn’t help me that much. But I remember he also had this interview series and I said, “Screw it, I’ll buy the upsell. I’ll buy the interview series.” He had this collection of interviews. Some of them were pretty crappy and useless.

One with Jay Abraham stuck with me. I still see to this day people are trading bootleg copies of the Jay Abraham interview with Tony Robbins. One of the things that he said that he recommends to business people to do, he said — I don’t remember if it was once a week or once a day, but he said on a regular basis, find a business person who’s completely outside of your world and just talk to them. Tell them what you do and how you solve problems, ask them what they do and how they solve problems, and really just let yourself learn from them. I thought, “I’m going to do that. Everyone says they’re going to do it. People are going to listen to this and say they’re going to do it. I’m going to do it.” I never did.

I had a greeting card company. We had the 12th floor of the 575 building in Manhattan. Up and down that building were businesses that I could have studied from, that I could have gone in and said, “I’m up on the 12th floor. I rent the whole thing myself. We’re like each other. I want to know more about who’s in our building. Can I sit down for coffee with you? Can I just pop in?”

I’m sure they would have loved it. I was an internet startup. They would have loved to find out what this internet startup was. I didn’t have the guts to do that. I didn’t have the time to do it. I didn’t have the momentum to do it. Now I get to do that on a regular basis. I think I learn a lot from it and I know they learn a lot from it too.

Sherry: So you’ve painted this picture of yourself as somebody who at least as a kid would go in the basement, separate yourself from the irritating, boring adults and sort of read books and kind of dream about what the possibilities of life might be like. I don’t know. Maybe say more about who you were as a kid. What kind of kid were you?

Andrew: It depends. I feel like we go through different stages as kids. There was a period in elementary school where I had a lot of friends and I liked my friends. Then there was a period in high school where I couldn’t relate to people. I remember that we would sneak beer off and drink it and I thought, “Who cares? My parents gave me beer when I was three years old. It’s not that big of a deal. I don’t want to sneak off and drink beer.” What I got really fascinated by was like some random stuff, but nobody would want to talk to me about it.

Sherry: What were you fascinated by?

Andrew: Like I was suddenly fascinated by The Beatles and I had to listen to every song they had and discover how great it was. I’d get suddenly fascinated by the early Mötley Crüe album and have to find someone to talk to about it. No one got it. I remember more specifically getting into two things — Republican conservative politics, very borderline libertarianism, if not over that border, and business. I just want to go and sit and talk about that and read about that and start a little company. Nobody cared about either one of those. Nobody cared about them.

I get it. I feel like the Republican stuff just kept getting all kinds of arguments. I would constantly get into arguments with people. I feel like I was telling them why they were wrong, and I was proud of my arguments. But at the same time, I said, “It doesn’t really matter. What do I care if Jonathan in high school is persuaded that I am right about the true form of government? He’s not going to do anything with that. Even if he does, one extra person, the benefit to me is too small versus ruining a relationship with someone who I’d want to be friends with forever.”

But I would ruin that relationship. Jonathan wants nothing to do with me. It’s totally fine. I’m not hurt by Jonathan not doing it. I’m hurt by myself saying, “You see that this is not helping you. Why do you have to keep yapping about it?”

Then the other part that I thought was helpful was studying business. I would read The Wall Street Journal every chance I got. It was so weird at first to read The Wall Street Journal. It’s like who are you to pretend to be a real business person like these guys? You don’t even know what a stock is. I read it and I would learn. I would read books on direct mail marketing.

Sherry: This is high school. So this is 15, 16, 17.

Andrew: Right.

Sherry: Okay.

Andrew: Yeah. I think the stuff that other people were into, like sports, I couldn’t get into it. I would try. A lot of the business books would even say — I would read business books for women and they would say pretend to like sports and they would teach you how to pretend to like sports. I’d say, “I can do that. All I have to do is read. I love reading. I’ll read the sports section every day.” I couldn’t do it for two days straight. So that was the fascination.

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Sherry: It’s a pretty unusual developmental trajectory. So much of what you’re supposed to do as an adolescent is figure out how to be in relationships with other people, like form your identity, usually through relationships with your peers. It sounds like you formed your identity somewhat in isolation.

Andrew: Yes. Books got me into it.

Sherry: Okay.

Andrew: Books got me to the group of people that I thought were really my peers. I didn’t think the idiot who was trying to score beer on a Friday night and pretend he was cool because he was at a party, I didn’t think that guy was my peer. I thought he didn’t even know himself. I thought he didn’t even know why he was there. He was doing it to kind of be able to show off to himself, if no one else, that he was drinking beer. Whoop-de-doo. He wasn’t even getting drunk from it. It’s not like you could say the high of the beer was doing something. They were sipping their beer like proper British ladies who drink tea, right?

Sherry: It sounds like you had at that age like a really unusual perspective on the future.

Andrew: Yes.

Sherry: You got the game.

Andrew: Yes.

Sherry: Then you were already kind of planning for living your adult life.

Andrew: I was. And you know what? Today, I think that would be a lot more acceptable. Today, because entrepreneurship is so celebrated, I think some people might be going towards it even though it’s not really for them. But today, you go into school and suddenly, luck of the draw. If you’re an entrepreneur at heart, you’ll find people who talk about entrepreneurship nonstop. Many of them are just posers. They pretend that they care about it. They pretend they know about it. All they really want is a quick score. It’s not who they really are.

So today, if you’re artistic, maybe you’re the odd man out who feels like a loser because what you like to do is actually be in a band and what high school kid anymore dreams of being in a band? If anything, they want to be the sole rock star like Beyoncé. They don’t want to be like Destiny’s Child. They don’t want to be like Mötley Crüe.

I think the bigger thing that I had to accept from that was who am I and forget all these other people. You can’t really find … you can’t hope that the school is going to drop you in with a room full of people who get who you are. No teacher understood and respected my need to be a business person. If anything, growing up in New York, you’re really surrounded by the liberal agenda, which is business is bad. By the way, I’m completely apolitical now after going through this like Rush Limbaugh stage. Even when I met Rush Limbaugh, I was too nervous to shake his hand, to give you a sense of how far I’d gone in that direction.

But it wasn’t supported. Meanwhile, it’s very possible that today, if you’re into music, I don’t know what the school system is like. I have a three-year old now, so maybe I’ll discover in the next few years. It’s very possible that if he’s into music, they’re going to laugh at him for being into music, “Do that in your spare time.” I don’t know.

But I do know this. They randomly throw you in with a group of people who are your surroundings. It’s very hard to bust out of your surroundings and the way you could do it is to open yourself up to people who are doing the things that you feel more connected to. If you can find that thing, you are so freaking lucky.

I used to think everyone should find it. If they could get serious and spend some time with themselves, they would know exactly what they’re about. I don’t think that anymore. If we are lucky enough to know what we’re into, if we’re into music, into art, into business, if we’re into athletics, if we found that thing that we are lucky enough to be into, I think it’s totally worth sacrificing everything for it. Most people don’t know who they are, don’t know what they want. It’s a tough thing to do.

And if you are lucky enough to do it, you can’t ever lie to yourself. I could never pretend, “Hey, I never wanted to be an entrepreneur anyway. I’m going to do this other thing.” I couldn’t. I’d like to. There are times when it’s so hard that I think, “No one else is going to know. I’m going to say I’m going to take this job over here that’s a boring job that I could just chill out in. No one’s going to know.” But I would know.

Sherry: You would know. Did your parents get you?

Andrew: Did my parents get me?

Sherry: Yeah.

Andrew: I do think they did, yeah.

Sherry: They were able to support you becoming who you were. They didn’t stand in the way or block you becoming who you needed to be.

Andrew: I think so. Thankfully, I come from a Middle Eastern family. There isn’t this tradition of going to college. I was kind of weird for going to college. Frankly, I probably shouldn’t have gone to college. I do think they got me. I think that I was so serious that if you met me, I would have beaten you over the head with who I was. Like my personality when I walked in the room would have told you in 10 seconds what I was about. If anything, I had to go to therapy to learn how to chill that out a little bit, to not be so much me.

Sherry: To let other people have a personality in your presence?

Andrew: No. To adjust my personality to them. I always was comfortable letting people have their own personality. But imagine I’m here, I’m ready to talk business. Then I go out dating at 29 when I finally say, “Work’s going well, but this other part of my life is not.” I start dating. What the hell do I talk to people about? How do I understand when somebody tells me at dinner that what she’s really interested in is world travel? World travel, who the hell cares about world travel, lady? Go get serious and work. That’s what I would say in my head.

Actually, I would accept that that’s who they are, but I would accept that I would want to travel. Imagine my girlfriend would go to dinner with me, want to travel and I can’t accept that I’m going to learn how to travel because all I want to do is go to work or go do something else. I had to learn how to do that. I didn’t even feel comfortable dressing for non-work. I would go to work in suits, and then when I thought I was casual, I would wear khakis, a button down shirt that was tucked in. No one is fucking me like that, right?

I had to go into therapy. The therapist looked at me and said, “Look at how you’re dressed.” I said, “I’m dressed down, lady. I’ve got khakis.” She had to say, “No, actually, you’re not.” It took me a while to understand it. I had to learn how to be more like the people around me so I could be more with the people around me.

Sherry: Was there a single moment or experience that led you into therapy?

Andrew: Yeah. I wasn’t dating. I really said, “This is a part of my life now that I want to explore.” I went out there to try it, and it didn’t work right. It didn’t work right. It’s a very challenging thing to do. I always thought I get rich enough, the solution will come to me. I get rich enough, I’m going to dress well, I’m going to be at parties. Someone’s going to dress me and that’s how I’m going to dress well when I go to parties. People are just going to know by my business success.

Look at Sumner Redstone. I’ve never heard the guy speak. But he’s not the most dashing looking guy. He’s not the most charming looking guy. He’s the guy who ended up running Viacom, CBS, he bought those companies and so many others. Paramount he bought. But look at the women who ended up dating and marrying, the women in his life.

So I said, “I love Sumner Redstone. He’s a hero of mine. He focused on his business like crazy. He became successful. The relationships happen.” I said, “All right, I’m successful. Where are the relationships?” They didn’t come. So that was something that made me finally say, “Let’s go into therapy.”

Sherry: “I need a relationship expert to help me out.”

Andrew: Yeah. I got a team of them, like all the resources I can. The only thing I didn’t do is go to the pickup artist guys. That is not me.

Sherry: You just needed a therapist and personal shopper.

Andrew: Yeah. I got the personal shopper. I spent like $25,000 on one shopping experience with this personal shopper. Boom. Everything is dressed. Now I learn I don’t even care about that.

Sherry: Well, now you have a wife, right?

Andrew: She does not want to dress me.

Sherry: Mission accomplished. What was your first entrepreneurial endeavor?

Andrew: Actually, speaking about clothes, what I ended up doing after going through therapy, I got the personal shopper, Catherine. I can’t remember her last name. I got her. She took me out and what’s cool about a good personal shopper in Manhattan is all these stores that you go to, you don’t realize there’s a next level in those stores. Maybe you go to the Armani store and walk around and go, “This is beautiful.”

What you don’t realize is there’s another section of the Armani store you’re not allowed in unless you’re the next level up client for them. Once you get in there, they bring you champagne. You don’t have to pick out the clothes. They bring you the clothes in there. They dress you. They tailor stuff to you.

You just are sitting and enjoying yourself, and if you’re comfortable with someone looking at you with your underwear, which I wasn’t, then you’re going to enjoy the experience. I wasn’t comfortable with them all looking at me in my underwear and bringing clothes in and out for me, so I would keep going behind the curtain like a scared little girl, and then I would come back out with my clothes.

But then what happened was I went for L.A. — is this helpful at all? Is this what you’re going for?

Sherry: Go for it. I’m interested. I’m a shopper.

Andrew: I feel like we’re just chatting here. I hope this is helpful for somebody. Then what happened was I went to L.A., and I said every night, six out of seven nights, I’m going to push myself to go out and talk to people, talk to women to see what happens. What I discovered was I just went through all these experiments. It wasn’t the clothes I was wearing. It wasn’t any of that.

It was do I feel comfortable with myself to start a conversation? It wasn’t about having the ideal lines. It was just do I feel comfortable with myself in a conversation? If I do, I may not take someone home. Frankly, I was not comfortable taking random people home. But I would be able to strike up some relationship every night with someone. Maybe it leads to good friendship and some of them ended up at my wedding. Maybe it leads to dating. Maybe it leads to something else.

What I learned was that the clothes that I thought were important weren’t. The success that I thought was important wasn’t. It was being able to have conversations.

Sherry: Your mindset was important.

Andrew: Yeah.

Sherry: And the clothes helped with that, it sounds like, or at least got you started on that path. It sounds like you practiced a lot.

Andrew: Yes.

Sherry: It sounds like you practiced a lot. Do you remember the moment of being afraid that you would fail?

Andrew: Yes, I do. I remember — in business or. . .

Sherry: Either way.

Andrew: I’ll go relationship with you, because I think relationships actually help power up my business, help me force myself to work. Yeah. It was around kissing. There was a girl I was dating. I was in high school. We didn’t kiss, and she thought I didn’t like her. The reason we didn’t kiss was I knew in my head I’m worried that I think I’m the man, but I’m also kind of scared, what happens if I kiss her and I’m a bad kisser and she’s going to talk about how much of a bad kisser I am or she’s going to see that I’m a bad kisser. So I didn’t kiss her because of that. There are little things like that that happened in my life that don’t seem like that big of a deal, but they are.

Sherry: Well, you were afraid of being seen, of being found out for potentially not being good.

Andrew: Yeah.

Sherry: It’s always better not to take the risk.

Andrew: Yeah. Exactly. I didn’t explicitly say that to myself. I think if I would have explicitly said, “Better not to take the risk,” I would have pushed myself to take the risk. I’m not aware of it. I wasn’t aware of it. I think you did an interesting episode about the voices in your head. I think what’s interesting about them is — I obviously have them. We all do have them. I think some of us have pictures in our heads, pictures of disaster, pictures of greatness or pictures of whatever. Others think through voices.

I know that we all have it differently, but I don’t think that I was aware that they were there. When I would hear people say, “We all have voices in our heads that are guiding us,” like our mom’s voice saying, “Go out there with a sweater,” or dad saying, “You have to be more aggressive,” I would have thought that’s for idiots and for psychopaths. I didn’t recognize that’s the way I was thinking too, that stuff was in my head and it was.

So there I didn’t recognize it. I think I also didn’t recognize it. So after I had this business success, but I also wanted to run this company, this greeting card company that I had in my 20s, I wanted to run it for the rest of my life. Look again at Sumner Redstone. I don’t mean to use Sumner Redstone as my idea hero entrepreneur. I think if anything, B.C. Forbes and Malcolm Forbes were much more so, back when Forbes was the thing that changed the way people thought about business.

But I forget what I was going to say about Sumner Redstone. I started falling in love with like B.C. Forbes all over again in my head and Malcolm Forbes.

Sherry: You were talking about how you weren’t aware that you had this set of voices in your head. You wanted to run your company for the rest of your life.

Andrew: Right. I wanted to run it for the rest of my life, and when I couldn’t, when it just couldn’t keep growing and I sold it to everyone else it was a success to me, I knew it wasn’t like a big financial success from the sale. The money came from profits in the business. Thankfully we had profits. But when it was time to close it, it wasn’t this huge exit. I didn’t even want a huge exit. I wanted to stay on forever.

That was the first big failure in my life, in a thing that mattered to me. In anything else, if I failed, I thought, “But I’m really good at business. I’ve been studying it forever. If you believe in yourself, if you work hard, you can do it.” Then I had that failure, and it rocked my world. It just changed my perception of business.

I didn’t realize how much I — when people said that I was successful, how much I clung to that self-definition, how much I clung to that, that, “All right. This is who I am. They always saw me that way. I definitely want to be seen that way. What happens if I launch something and I fail? What happens if I launch the next thing and it doesn’t go very well?” So, there was another place where I was definitely afraid.

Sherry: And that wasn’t really a possibility in your head until that point, until you had to sell the company.

Andrew: Right. I really did grow up listening to the self-improvement gurus who said without a doubt, as long as you believe in yourself and really see the vision, you will make it, especially those older guys. They had this belief that when you want something and the world says no, you should just keep going after it because that’s how you succeed.

There’s a story that Napoleon Hill used to tell, the author of “Think and Grow Rich,” where he was working with a salesperson who wasn’t closing enough sales, and so he gave the guy one of these horns that I guess at some point people used to put up to their ears when they were deaf or hard of hearing. He said whenever you try to sell someone, if he says no, put it up to your ear and say, “I’m sorry. I can’t hear you, but let me tell you a little bit more about why you should buy this life insurance.” He did work with a life insurance company to help their salespeople.

This was indicative of how they believed you need to continue. As long as you don’t hear the no, you will get to the yes. As long as you believe in yourself, you will get there.

Sherry: That’s not always true.

Andrew: No.

Sherry: So how do you say it now? How do you think about yourself now in that success/failure category?

Andrew: I don’t know that I consider success/failure. I do consider living up to my vision of myself versus not. I do think that I’m not living up to it. I want to definitely be a lot bigger in every way.

Sherry: What do you mean bigger?

Andrew: Bigger, much more money than I have. My wife asked me the other day, “How much?” I said, “I’ll always want more,” and she said, “Really, you want more?” And then she knew to drop it or thought she should drop it. I don’t think she should have. I think I’ll always want more. For sure.

Sherry: What’s the point of more?

Andrew: So she dropped it and then she said, “Let me share what I would like.” She said, “I’d like to travel.” She talked about traveling and she and I both love traveling. In my head, I thought, “How much traveling is enough, Olivia? If you travel to 10 cities this year, would that be enough and then will you finally drop this? How about if you do it for the next five years?”

There is no enough. You always want to see another place. You always want to experience more travel. If she reads a book every night, I would never say to her, “How many books are enough, Olivia?” She’ll always have a book going, always paper, never digital. Once in a while, if she has to read a book, she’ll do Kindle. It’s the same thing with money — more.

Sherry: The money isn’t about the number, it’s about the experience of getting it?

Andrew: And the number. I like the number.

Sherry: Okay. You like big numbers.

Andrew: Yeah. I don’t even like doing stuff with it. It’s kind of a fun thing to pursue. I definitely want more of that. I want more fame. I don’t like that I’ve been doing interviews and — I love that when I’m San Francisco, people know my work. I love that people who I sign up for their software will suddenly say, “No way, Andrew, I’m a big fan of your work,” but I have to be honest with you and say that’s not enough. I’d like much more attention, much more recognition. I like all that. I want it all.

Sherry: Is that what it would mean for you to be really living your life?

Andrew: No. I think I’m pretty set there. I’m really living my life.

Sherry: Okay. That’s where we began, your reflections on your parents’ friends and their conversations about food that were just so boring and the sense in which maybe they’re wasting some space, wasting some option.

Andrew: Let me tell you something more about this more stuff, this mentality I have. I was just on a call with a group of entrepreneurs who came to me for some help. One of them said, “Andrew, I need to just finally launch a site.” I said, “How much is it going to cost you to launch it?” He said, “Well, I’ve got a friend who’s going to do it.” I said, “If you had to hire someone, what would it cost?” He said, “$500, but I have a friend. By the end of the day, because I talked to you, Andrew, you lit a fire under my ass, I’m getting it done.”

I said, “How much would it cost you?” He said, “$500.” I said, “What’s your email address?” He gave me his email address. I PayPal’d him $500. I said, “Now you have belts and suspenders. Go to UpWork if that’s what you think you’re going to get for $500 for your website, go and get that site up.” So now he has two different approaches to get the site up. One way or another, he’s got to have this thing up so that he can continue his presales.

After we got through that conversation and he stopped beaming at the way I responded, he said, “Andrew, how do you keep yourself motivated? How did you do it back in the old Bradford & Reed days?” I get it. He’s in a good position. He’s a smart guy. He’s got a good job. He doesn’t need all this agita. He doesn’t need to keep pushing himself to have two different nudnicks out there trying to build his site and demanding more stuff from him. He doesn’t need that.

So I said my answer was I got in touch with everything about myself, including all the things that I didn’t have and I wanted. I think we’re supposed to pretend it’s okay. I think we’re supposed to look out in the world and see there are people who are in Paris. Forget about wanting to be like everyone else. No, we’d like to go check out Paris. We’d like to go and hike the Annapurna Circuit or whatever it is. We know that we’d like to do this stuff, but we don’t give ourselves permission to want it because we’re not supposed to. Just be happy where you are is what we tell ourselves.

Sherry: We want to protect ourselves from disappointment.

Andrew: Right. And from feeling like, “I want all that and I’m not there, so look at how much my life sucks or how I’m not there.” So I told him I like to get in touch with who I’m not and what I want and really be bothered by it. So I’m comfortable, perfectly comfortable saying to you, Sherry, that I would like more attention, I’d like more money, I’d like to fuck a lot more, and I’d like to have more time with my kids, not in that order. Is that okay to curse like that?

Sherry: Absolutely. Which order would you put them in?

Andrew: The kids are kind of separate. I didn’t think that I would enjoy spending time with younger kids because what do they do, swing? I love it. I took the day off two days go to just go be with my three-year old. We went to the indoor playground. Do you know the stuff that gets these guys riled up with excitement? Go into an indoor playground. It’s great.

Sherry: Usually it’s like the pieces of small rubber that are out in the indoor playground, at least for my kids.

Andrew: What is?

Sherry: The little pieces of small rubber on the ground.

Andrew: Right. They want to play with that.

Sherry: It’s not even the swings or the tools, it’s like the dressing.

Andrew: And by the way, I love that it’s all rubberized. It makes me feel better. A three-year old, if you let them climb a building, they’ll climb a building from the outside. At least in the indoor playground, everything is rubbery, everything is soft. Yeah. So I want more time with them, especially now at this age because I can actually blow their minds with like indoor playground. How great is that? I want it all.

Sherry: How do you deal with the space between what you have and what you want? What does that space feel like? Is it angsty? Is it driven? Are you calm about it? What’s the emotional quality?

Andrew: It’s a little bit of all of it. I think for me, it’s a little bit of all of it. Sometimes it’s definitely angry, like really, am I going to end up at the end of my life not having gotten all this stuff that I want, all these achievements that I want, all these experiences that I want? Then I think that’s actually not bad. If I end up just like this, I think it’s not bad. I really enjoy my life. I really feel like I’ve at least attempted — here’s what I think about with that.

When I was I think it was senior year of high school at Brooklyn Tech, they said anyone could be student body president. I was really into politics. So I said, “This is an opportunity for me to learn about politics.” So what I’m going to do is I’m going to apply. I even took whatever class they wanted you to take to learn about politics or about civic duty and then you can run for president. I ran for president and I lost.

I lost big. I didn’t just lose big, but I think I came in fourth place. But I went and told everybody that I wanted them to vote for me. Even Jonathan, who didn’t like me, I said, “Would you vote for me?” I went and asked them all. I put signs up all over the school to the point when they told me to take it down. I remember when I failed, I didn’t say I humiliated myself by showing everyone how much I wanted it and letting them all say that I didn’t do it.

I remember how proud I felt. For once in my life, I went all out without any fear of failure, without any embarrassment. I do not look back on that experience and I say to myself now saying I wish I had done this one extra thing. I did not look back and say, “I wish I had the guts to ask my friend Henry to vote for me.” I do not look back and say, “I wish I had the guts to put up a poster in our social studies class.”

I just did it. So the feeling of even failure at that point is so much better than the feeling of success in other places, to know you’ve given it all. There’s a Vince Lombardi quote that I don’t remember about leaving it all out on the field and how it makes you feel. That is what it is.

So when you say to me, “How does it feel?” It feels good. It feels at times like really painful in my stomach. My stomach churns over the last few days, especially because I’m taking on so much. It feels sometimes a little bit scary. It feels sometimes very exciting. But overall, I want to feel like that kid who gave it all to try to be class president, even though he didn’t get to be class president.

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Sherry: You’re proud of the effort, you’re proud of the guts that it took to do that?

Andrew: Yeah. Imagine to not look back and say, “If only I’d done this one other thing,” right? There aren’t a lot of experiences in your life where you can say that. I started this company back when I was in school that did — there’s this teacher who taught the SATs — by the way, I’m trying to read your eyes. I like that we’re doing video. I’m trying to read like am I on track for what you’re looking for in the podcast or not.

Sherry: Just talk man, you’re fine. That’s a psychologist problem.

Andrew: Is it? I think also, you’re such an easy person to talk to and we’ve met in person, I’ve heard you. So we’ve got some background. I’ve also heard about you from people. I’m just enjoying this conversation in a way that I don’t usually get to. I think most people don’t listen to me the way I listen to them in my interviews. I don’t know. I just don’t enjoy talking to people the way I enjoy talking to you here. I want to make sure that I’m not getting carried away enjoying it and not giving you what’re looking for, because god knows, there are people who are listening and we’re here for them.

So I took this SAT class. There was this guy, he was so good. Yes, he taught you the good stuff, the stuff that would take forever to learn. But he also would teach you things like, “Hey, look, they’re going to tell you that you need to figure out a way you need to measure this triangle. Let me show you how you take a corner of a piece of paper off of your sheet and use that for a ruler.” He had all these quick tips.

So I said, “Imagine if this guy just gave somebody who was kind of hard up, a little scared they’re not going to hit their numbers, give them just an hour and a half of just those tips, just those things. That would be huge. I’m going to create the cram session for the SAT. If you want to cram, this guy’s going to give you all the techniques.”

So I made an agreement with him. We were going to split the money. I was going to get people for him because I sucked at the SAT, but I loved business. I went out there and under the cover of darkness, I posted signs all over the bus stops near the high schools — I must have been in high school at the time — trying to get people to sign up for this thing. I did it at night. I didn’t talk to people. I was too chicken to actually put myself out there with this, and all I got were people who were just kind of calling the number, seeing it was voicemail and hanging up because I set up a voicemail number on it.

That’s the way that I don’t want to go down. I’d rather go down like the kid who tried to be class president and wasn’t the kid who wanted to just sell SAT cram sessions and couldn’t even like go and talk to people.

Sherry: How do you relax? You’re an intense guy. What does recharging look for you?

Andrew: I am kind of intense lately. Recharging used to be reading a book and just kind of relaxing. I can’t do that so much. I speed-read books now. Didn’t you do a session on speed reading? I didn’t get to listen to it. You might have.

Sherry: I don’t know if we did. Maybe Rob did. Oh yeah, he just did one about how to get the most out of books, but I wasn’t part of it. Go ahead.

Andrew: So, because I do interviews with authors, I’ve learned to read really fast and prepare fast. So I do that. I just don’t get that much out of it. What I do to relax is I like to run long distance. I like to cycle. Now that I have kids, I don’t want to be away from the kids for a long time, so when they go to sleep, I take a bike in the backyard. We’re so lucky in San Francisco, we have a nice-sized backyard. I have a bike with a smart trainer, and I attach the bike to the smart trainer. The smart trainer connects via Bluetooth to an iPad that I attach to the front of my bike and I use an app called Zwift, when I cycle fast in my bike, this character on Zwift cycles fast.

So if I have like an hour of downtime at home or hour and a half, my wife knows I’m out there, I’m watching some stupid thing and Zwifting like crazy and trying to get up the mountain in Zwift as fast as possible. My fastest king of the mountain, if anyone’s out there listening and using it, is 39 minutes. So I’m not super fast, but that took a lot of effort and I’m very proud of it.

Sherry: What happens to your mind when you’re cycling? Are you thinking? Are you planning? Are you scheming, or are you off?

Andrew: A couple of different things. It’s either vegging out and watching something like “House of Cards” or I say, “I actually can push myself to do 150 watts right now,” that’s the way they measure output. I can push myself to get to the top of the mountain before Olivia calls me in because I need to do bedtime with the kids.

If I really hustle up on this thing, I can actually get to the top. Even though the Tron bike, which is what they give you if you do intense miles going uphill in this thing. This app even tells the smart trainer this guy is going uphill. It’s hard to get uphill. The smart trainer is so smart. So I do say, “You know what? I think I can do it. I think I can push myself further than I thought, a higher level than I thought.”

Or I just kind of lose myself sometimes in the virtual world of it. Not so much when I cycle, when I cycle, I definitely will spend way too much time looking around, which is why I never finish fast. I will spend time looking around and cycle, getting lost in my audiobook.

Sherry: Observing.

Andrew: Yeah.

Sherry: How has being a parent changed you?

Andrew: In a lot of different ways. It forced me when my first child was born, I knew I wouldn’t be able to spend as much time on work and things couldn’t collapse as often. So it forced me to systemize my company, to turn it into a real company and not just a thing that I did. That gave me a lot of free time with him. He and I spent a lot of time walking through the neighborhood. I’ve changed so many diapers. I have no issue with any of that. He can cry. I see parents get upright about it when their kids cry. I just love it. Bring it on. I’ll do something goofy, and he’ll love it. I got a lot of that from it.

Then when my second child was born, I started to think about — this was about nine months ago — I started to think about what would happen if I died. I never had these fear that all these parents have, which is what happens if the baby dies in his crib? I knew he would be fine. And if he would, no baby monitor is going to save them and everyone worries about it, so I’m not going to worry myself about it. I could feel comfortable letting them stay in bed, leaving them there and getting them there.

Where I started to worry is what if I die. It’s that Malcolm Gladwell book, that latest one that he put out there that got it in my head. What is that book called? You’re looking it up, it looks like.

Sherry: I don’t know the most recent one.

Andrew: In one of his books, his latest one, he talks about how many successful people had fathers who died, specifically fathers, really interesting. He said this actually can push a kid to extreme levels, but also it could be incredibly damaging. It’s such a traumatic thing for a parent to die.

That reminded me of Jeff in my elementary school, whose dad died. I remember a specific incident where people made fun of him. I was going to say we all made fun of him, but I was an observer on that. It didn’t hit me, “Why would they care? They make fun of everything. We all make fun of everything. Who cares?” I just kind of took it in from an interesting, “Why would he care?” not even like putting him down, just taking it in.

He cried because his dad died, and someone made fun of him. It just kind of stuck with me. Then when I read that book, I thought, “That could be me.” There’s a tiny chance my kid could grow up to be president because of this traumatic experience, but there’s a much bigger change that he could be starved and damaged by that. Then what else, what other damage would I end up doing?

Like J.P. Morgan, I forget who it was after J.P. Morgan died who saw he really wasn’t so rich. Interesting. Like there’s so many things that you could not be able to do. Maybe I don’t leave enough money for the family. Maybe I don’t leave enough of myself with the family. So I started to work a lot harder to figure out what I need to leave just in case I die. I don’t mean just money, though money became such a needy thing. I wanted to get my will in order and all that stuff.

Sherry: But you want to make sure that there’s enough of you to sustain your kids so that they’re not damaged by — or you’re minimizing the damage that would happen if you weren’t there?

Andrew: Yeah. It became more dramatic, the concerns that I had. It flashed to — I recently heard an audiobook about Joseph Kennedy. What a tough womanizer he was according to this book, and he was never at home. But when JFK as a child was sick, he would just go and sit next to him. And I thought to be able to do that for your kid when everything is going on in his life, to be able to say, “Yes, it’s all going on and I’m very important,” and he was important to the economy, to the world, to his businesses, but for him to then say, “It’s more important that I sit here with my kid and to have the freedom to do it knowing that things aren’t going to collapse was really important.”

So I don’t want my legacy to collapse if I have to go and spend who knows, a week, a year, five years with a kid who’s sick. I want to be able to keep it all going. So all that disaster, all those collections and disaster thoughts came into my head and …

Sherry: Changed the way that you organize your business and your life.

Andrew: Yeah.

Sherry: The kids don’t care how important you are if they don’t feel that they are important to you. You want to be able to sit there.

Andrew: That’s never a concern that I’ve had, that they don’t think they’re important to me. The concern is even not so much — like leaving them financially well off is important, just also leaving a legacy now for our kids, one way or the other. It could be a legacy of fakeness that we’re putting out on social media, could be a legacy of really world-changing ideas that we’re getting to leave out there. I think that’s important. It can’t just disappear.

Sherry: Do you think there’s — this is a question that Rob and I talk about a lot. We are certainly much more financially well off and stable than either of us were as children. So our kids are growing up in this life where they’ve been to Paris, they’ve spent a month in Thailand. They’ve had all these kinds of experiences that our wealth has made possible. Sometimes I struggle with the challenge of how do you then infuse them or let them go through the struggle of being hungry for something and the drive that comes with that.

Andrew: One of the only good things that Steve Forbes did for the Forbes empire — so it was B.C. Forbes, then Malcolm Forbes, then Steve Forbes who came and took it over, and I think Steve Forbes let it go to pot and now it’s like anyone can put any crap up on But one of the things he did was he created a magazine called Audacity.

Audacity was about tremendous wealth through the ages, historical wealth. And it did this piece about kids who grew up under tremendously wealthy families and how they were raised. Audacity Magazine should be in libraries and should be accessible to everyone forever. It’s just a work of brilliance.

There were lots of different approaches, everything from, “We were given everything and we didn’t appreciate it,” to, “We were given everything and we did appreciate it,” to this one girl who said, “My parents made us pay for anything because they didn’t have anything when they were growing up. They had us pay for things like the dentist. It was all great that we had a sense of responsibility, but in the middle of the night, we worried how to pay our own dental bills.”

So the reason I’m bringing that up is I know there are problems there, and there’s no easy solution. If these people who moved worlds couldn’t come up with the perfect answer, I’m not going to pretend I can. I’m not even at that issue with a three-year old. It’s not much of a problem. It’s like do I give him chocolate once a week or once a month or never is the big question we have.

But I will tell you this, even though I can’t solve that, the opposite problem is much worse. How many times do you see families fight over money? Even if it’s not a fight over money, it’s a fight because someone is stressed and the stress is coming back to money. I would gladly take this problem over the other set of problems if I had to. This is not an easy problem to solve, right?

Frankly even for ourselves, I realized just this year, when I have any need, I just go to Amazon and I get something and I solve it, any little need. I think I can always return it if I don’t need it, but I never do. It piles up. That’s definitely an issue that I have. So I’m not going to say I can solve it for my kids if I haven’t yet solved it for myself. I don’t mean to minimize it is what I’m saying, but I’d definitely take this problem over the other problem.

Sherry: Absolutely. So there’s some gratitude. What do you feel most grateful for?

Andrew: That I have a chance to live the life that I really want, the stuff I really wanted. I used to love the library in Jamaica, Queens. It was the big library. It was in a bad neighborhood, but it was great. It had all the books it felt like. Unlike the ones in Manhattan, you could actually get access to them. You didn’t feel like you needed to make an appointment and it was meant for scholars. This was meant for you. You get to go in there.

I remember being there one time waiting for my turn to talk to the librarian and looking behind the sink and saying, “Can you imagine? This guy’s going to have to go and wash his hands after.” Imagine he has to go poop, and then he has to come back out here, has to wash his hands with everybody looking at him because that’s where their sink is. “That’s not going to be me.” Then I said, “What if it is me? What if the circumstances of life force me to live things to that level to the point where I’m not happy with it?”

You never know. You never know what life can push you into. How many people were rich and then World War II came up and then suddenly they had to live hidden or crappy lives and be happy they’re alive. You never know. I thought all these books that I’m reading can’t protect me from — forget about washing your hands with everyone looking at you after you poop, but some unusual circumstance where your life isn’t your own, where your life is forcing you to do things even on a day-to-day, mundane level that you don’t want to do.

I’m really glad that I don’t have that. I actually have the opposite of it. I get to dream it and not live it entirely the way I’d like to. I’d like more, as I said. But at least I get to be the master of my own story, the writer of my own story. That means the kid who loved reading biographies gets to create biographies. The kid who was dying to learn how to talk to girls or talk to people, now I feel totally comfortable doing it.

You and I met at Converted 2016 when you sent an invitation for me to come here, you said, “Hey, we were in bed together,” with a little smiley face or something because we were. It was like you me, Rob, and I think other people crammed in to the bed in my hotel room. It was a joke for a photo, right? But I felt comfortable suggesting this weird thing. I felt comfortable saying, “Let’s all do this wacky thing.” I felt comfortable saying, “Everyone at this conference come to my room because we’re going to do a scotch party,” and I felt comfortable knowing that it’s not going to be awkward with just one person or no one showing up.

It’s not going to be awkward because I won’t know how to talk to these people. It’s going to be great because I’m going to get to meet new people. You and I had a chance to talk. I’m going to get to connect with old friend in person again. I’m going to get to have a fun night and enjoy myself.

So that’s it. I’m proudest of the ability to not stand on the sidelines and wish I got to do this stuff and wonder if I could ever get out of my shell and talk to people, but actually be able to do it.

Sherry: Not be afraid.

Andrew: Yeah.

Sherry: Cool. That’s a good place to leave it.

Andrew: Yeah.

Sherry: Thank you.

Andrew: Thanks for having me on.

Sherry: It’s fun to talk to you.

Andrew: Same here.

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