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Episode 12 May 10, 2016 | 33min

A Little Chat about Terrible Failure

Our co-founders define and discuss failure in business, tech, and life.

Show Notes

This week, Paul and Rich try to define success and failure in business, the tech industry, and their lives. The result is part topical conversation (Apple, Yahoo, the penetrating gaze of Theranos founder Elizabeth Holmes) and part therapy session. “I don’t know how to feel successful, personally,” Rich admits early on. Paul eventually matches him, announcing, “I think that everything I do and everything I touch is a failure.”

Rich Ziade: Hi everyone, and welcome to Track Changes, episode #12. I’m here with my co-founder —

Paul Ford: [impressive trumpet noise]

Rich: Oooh.

Paul: That’s a little trumpet sound to announce podcast #12.

Rich: Yes. We’re doing it.

Paul: All right. My name, Richard, is Paul Ford.

Rich: And I’m Rich Ziade.

Paul: Here we go!

Rich: Welcome.

Paul: What do you want to talk about today?

Rich: We need to take it down a notch.

Paul: Oh yeah. You know, we talk a lot about things that are great.

Rich: Yeah. How great we are.

Paul: How superb the internet is and how wonderful the web and technology can be and how they can change your life.

Rich: Yeah.

Paul: But the reality is that most things that you build, and this includes you and this includes me, just don’t actually work out that well.

Rich: They fail.

Paul: Success is not the norm. And yet, honestly, if you go and you look at how people talk about technology, you really would think that it was.

Rich: Well that’s because they go and they do the profile at the end of the, the news broadcast about, you know, the Uber guy.

Paul: Right, or Zuckerberg.

Rich: Yeah. I just saw two days ago the Chobani guy. Chobani tastes like liquid styrofoam by the way. But the Chobani guy, who’s made billions, gave 10% of the company to the employees of Chobani. Did you know this?

Paul: Uh, no, I did not know anything about —

Rich: Because he’s successful!

Paul: First of all, wait a minute —

Rich: And that’s success.

Paul: —why do you hate Chobani?

Rich: Have you tasted it?

Paul: Sure. You get, it’s got a little pocket on the side, it’s like a pair of jeans. You got a little, you know, like, walnut dip in there, and you smear it into the…the Chobani…

Rich: I don’t know, that’s Fage. Fage, that’s right. That’s the wrong one.

Paul: That’s Fage?

Rich: Yeah.

Paul: Well wait, doesn’t Chobani occasionally have the little —

Rich: Chobani, let’s clarify. Chobani is Greek yogurt, but it has a weird, plasticky taste —

Paul: I feel that this is some Lebanese thing, where you’re just —

Rich: It might be Lebanese.

Paul: —you’re really uptight about yogurt.

Rich: Bringing it back around, he’s wildly successful.

Paul: So this is the thing, so you’re basically —

Rich: They’re not prof —

Paul: You’re telling me Chobani’s garbage, but it’s made billions of dollars.

Rich: It’s made billions of dollars. It’s because Greek yogurt came out and Danon was caught flat-footed.

Paul: It’s true. Danon’s really bad.

Rich: Well, it’s just regular stuff.

Paul: All right, look. OK, so Mr. Chobani…

Rich: Anyway, so he made, he’s a huge success. And we talk about successes. We don’t talk about failures that much. You profile success stories. They end up on the cover of Fast Company.

Paul: And everybody tries to hide — you don’t, nobody is like, “Hey, Fast Company, come profile my failure.”

Rich: Correct. Now look, every so often The New Yorker will profile a failure.

Paul: Right.

Rich: Like, deeply. They’ll go back into childhood as to why the thing failed. And those are fun to read.

Paul: That’s the outlier. Your typical business story —

Rich: Yeah! It’s about success, right? And that’s tough. That’s tough. Well first off, we’re saying success as if there is a clear definition of what success is.

Paul: What is success to you?

Rich: To me personally?

Paul: Yeah, to you personally.

Rich: Do you think people would be interested in hearing —

Paul: Sure!

Rich: —my —

Paul: We’ve got to start somewhere. They want to know what our biases are.

Rich: I don’t know how to feel…successful, personally.

Paul: Oh really? You don’t?

Rich: No. I just keep running. And that’s OK, because I’m actually generally happy, but I don’t know if I’ll ever reach a, “Oh, I’ve arrived. Everybody relax.”

Paul: Right, you like to stay, you need a certain level of stimulus…

Rich: Uh…I do, and I think my mindset is really geared around not getting hurt, strangely.

Paul: I see.

Rich: So I’m, that’s just gonna be the game for me, and I’m OK with that. I…what are we gonna do? I become depressed, if I’ve reached success and I said, “OK, you know what, I’m just going to buy a Playstation 4 and just sit around in my shorts because I’m successful.” I will become fully depressed.

Paul: You think — how long do you think you could do that before you got depressed, though?

Rich: Probably a couple of weeks?

Paul: That’s what I think. I think I could get, I could get really, I want to play that game, “The Last of Us,” where they are like, zombies and you’re running across…I just —

Rich: Yeah. You’d find a little mission for yourself, isn’t that the thing?

Paul: I’ve missed the whole Playstation scene, like Playstations 3 and 4.

Rich: Yeah. Exactly. There’s a lot of great stuff in there.

Paul: I would love to just experience that. But I think, like you, after three weeks…

Rich: It becomes sad.

Paul: Well then you’re like, “I gotta…I gotta…why am I wearing underwear, it’s two PM?”

Rich: And you could argue that this is a fatal flaw, right? Like, I know people who have travelled to retreats where they do meditation and then they reset themselves, and they come back and they have this weird smile on their faces, and they explain to me that, “You’re running around like a rat in a…”

Paul: [weary sigh] The smile fades, though.

Rich: What is it, hamster wheel? I’m in a hamster wheel, and…

Paul: I like to work.

Rich: “You don’t know how to become happy.” How to be happy.

Paul: I like to work. Look, my life is —

Rich: How to find your center.

Paul: My life is very imbalanced, there’s no way around that. I have an imbalanced life. But I know about myself that even if I can get things balanced, I need a certain buzz of activity going straight into my brain, or I get very depressed.

Rich: I need it to be out of reach.

Paul: Yeah.

Rich: I need to see that Men’s Health abs guy to know exactly how I will never be. Is that weird?

Paul: No. I mean, for me success comes when…you’re just never bored.

Rich: Yeah.

Paul: Success comes when you can, like, just get the signal into your brain from…I love New York City for that reason.

Rich: Yep.

Paul: You’re never bored walking down the street in New York City. It is shenanigans all the time.

Rich: Right.

Paul: If you have a vague interest in the world, and you’re like, “Oh my God, look at the Brooklyn Bridge. That took a lot to build. People died building it.”

Rich: Right. There’s not a lot of lifestyle businesses in our industry. There’s not, like, you —

Paul: Well, there are, but they’re despised.

Rich: They’re despised, and also they’re just not viewed as successful.

Paul: No, I know.

Rich: They’re viewed as, “Oh, they get by.” I know a couple of —

Paul: We should define what a ‘lifestyle business’ is for people.

Rich: A lifestyle business is, you know, I make enough money, I’m not looking to grow 8x, or 5x next year.

Paul: It’s what you would call a small business almost anywhere else.

Rich: No, it could be a large lifestyle business. It’s just, I think your aims are just different. A successful coffee shop that a family runs is a lifestyle business, I think. Look, I know of SaaS businesses, a few SaaS businesses —

Paul: Software as a service.

Rich: Yes. They’re hosted services that a company can sign up for and they have five million in revenue a year? Ten million in revenue year. Some of them have fifteen million?

Paul: That’s a really large, kind of wonderful amount of money.

Rich: And they view themselves as failures.

Paul: [long sigh]

Rich: They view themselves as unable to hit the stride and really do the thing, because they’re looking at Salesforce as the mark of success.

Paul: Which is multi, multi-billion-dollar company.

Rich: Just a monster, right?

Paul: You know, the thing is, though, I remember when I was a younger person, I was starting out, you know, I’ve had two careers, one in technology and one in writing.

Rich: Yeah.

Paul: They’ve always gone parallel. And I can remember how anxious I was about my writing career, and then I got a job editing at Harper’s Magazine, and then suddenly I was less anxious, and it’s very easy for me to get on the other side of that, having passed the test, having gotten into the, you know, the secret chamber of editing.

Rich: Yeah.

Paul: And to look out at everyone and go, “Dude, no big deal. Just relax. Don’t — ”

Rich: And find satisfaction in, even those moments, like, right, of —

Paul: Right. But I mean, we go out and you go, like, “It’s no big deal. You should stop striving for that.” But you always do it when you’re on the other side.

Rich: Yeah, exactly.

Paul: The hardest thing to do is to go, “Actually, that truly is a meaningless measure of success, even though I haven’t attained it.”

Rich: Yeah.

Paul: And so you get that, I can hear it with those lifestyle businesses, like, by any objective reality, they should be able to look around them and go, “We’ve achieved material success. I have a large number of people who are employed. We have clients who like and respect us and I can see a five- or six-year horizon where things are still going pretty well.”

Rich: Yep.

Paul: That is absolute success by any standard.

Rich: It really is.

Paul: I mean, it should be celebrated. It’s not.

Rich: It’s not. It’s not.

Paul: It’s not. It’s literally of great value to the republic, right? It’s good for this country to have lots of businesses where people have jobs instead of, like, some company with eleven people that’s worth $40 billion for those eleven people.

Rich: Yeah. You know, I think, because technology, you know, frames itself as defining the future?

Paul: Right.

Rich: I think there’s a different level of pressure than, like, the fashion industry, or, you know, the…

Paul: It’s always very permanent, right? So the fashion industry knows that every year’s going to be the same thing, but different.

Rich: Yeah.

Paul: The truth is actually that’s true of the technology industry, except that there’s this bizarre straight line with Moore’s Law, where you can just do more and more processing for less and less money over year to year, and so, which means you can show ten times as many pictures.

Rich: Yeah.

Paul: Or you can show a movie on a phone.

Rich: Right.

Paul: Before you could just make phone calls.

Rich: Right.

Paul: So as we talk about it, we talk a lot about the past of technology, and it almost always, when people tell stories about how things were in the eighties, nineties, early 2000s, they’re exactly the same. They’re doing the same things. But they didn’t have as much computing power and they didn’t have as many users.

Rich: Right.

Paul: And so it’s a bizarre industry that way because there is an actual fundamental change that occurs almost every eighteen months, where you can do something radically new for the same amount of money, that you used to be able to do something, you know, that was simpler.

Rich: You know, I’m a baseball fan.

Paul: Mmmm hmmm.

Rich: I’m less of one today. And one of the things that always fascinated me was why the fastball has gotten faster over the years.

Paul: OK.

Rich: I’m thinking maybe we understand diet better? I mean, there’s no way we genetically improved, like we didn’t evolve in the past fifty years —

Paul: I think we understand —

Rich: —so the fastball went from 50 miles an hour to 100 miles an hour.

Paul: It’s just, it’s possibility, right?

Rich: To your point, the bar just keeps moving. And it doesn’t stop.

Paul: Right, so now what you have are people coming out of, like, good colleges deciding to go into start-ups who feel that they’re not going to succeed unless they earn $100 billion.

Rich: Entrepreneurs, you mean.

Paul: Yep.

Rich: Well, that’s the framing, right? The money drives that, right? I’m not going to fund you if you’re just going to make me twice my money, or five times my money. You have to be the lottery hit. And I think that —

Paul: I think it’s hard for people —

Rich: —kind of pressure, changing the world, I mean there’s also, they mask it in terms of —

Paul: —it’s hard for people to understand how the story of venture capital guides the story of the technology industry.

Rich: It’s fundamental, right?

Paul: It’s about exponential gains.

Rich: It is.

Paul: And disruption and all that stuff. And so the little lifestyle businesses —

Rich: Yep.

Paul: —they really don’t fit inside of that narrative.

Rich: No, they don’t at all. Like, I’ve seen successful businesses, I mean, profitable businesses try to raise money, and they’re just told, look, you’ve got a nice business here. You’re not for my game. I’m going to fail — I’m the VC for a moment. 95% of my investments will fail. So every so often, I need two or three to just be such break-out successes that it nets out that I’m making money for my investors. That’s the game, right? And so, I’m not looking for middling stuff. I’m not, if I want middling stuff, I’ll just go invest in, you know, AT&T and IBM. What I’m looking for is the lottery ticket here, that’s going to make it all worth it. And so, here, I made a list of things that are now supposedly failing.

Paul: OK, tell me about these failures.

Rich: OK, recently Apple reported that people aren’t buying as many iPhones.

Paul: [very dramatic sigh]

Rich: OK.

Paul: They’re garbage.

Rich: They, they —

Paul: What a garbage company.

Rich: Their quarterly earnings, just to give you context, this might be the most extreme, ridiculous example. The stock went down, it was viewed as, this is the beginning of the end of innovation for Apple, of real growth for Apple, right? And their quarter was $50 billion.

Paul: [disgruntled noise]

Rich: Right?

Paul: God, they suck.

Rich: [laughter] I mean look, the value of Apple today is based on what it is going to pull of in the next three, four years.

Paul: But that’s the thing, my issue with all this is, like, it’s just narrative, right? The actual value of Apple compared to anything that a human being can understand? You can’t figure that out.

Rich: But is that failure?

Paul: No!

Rich: Are they failing?

Paul: Of course it’s not. It’s a convenient story that people can jam into the media, that they can jam into a couple column inches or turn into a big, you know, trend piece about the downturn in technology. You need that stuff in order to keep the sort of larger narrative around tech. The reality is, like, Apple is its own moon.

Rich: Yeah.

Paul: They’re seeing this, and they’re like, [under his breath] “ah man do we gotta…” Like, to Apple, the public markets are, like, one of the entities that it deals with along with China.

Rich: Yeah.

Paul: You know, pollution. These are things, Apple’s thinking at these meta terms —

Rich: Yeah.

Paul: What do they have? I mean, they have an unbelievable amount of cash on hand.

Rich: Insane amount of cash.

Paul: They’re good for fifty years. And we talk about them —

Rich: But that’s not —

Paul: We talk about them like a bodega that might go out of business.

Rich: Yeah, because the bar is where it is, right?

Paul: But that’s crazycakes.

Rich: All right. Let’s keep going.

Paul: Apple’s going to be here — until you and I are dead, there’s gonna be Apple.

Rich: Yes. There is going to be Apple. And that’s a classic example of, you know, growth has slowed. Like, Google had a good quarter, actually.

Paul: Yeah.

Rich: A very good quarter. But the day is coming where —

Paul: I think the entire finance industry’s such a —

Rich: Doesn’t everything slow down at some point.

Paul: They’re all such babies. You know?

Rich: Yeah.

Paul: Did you read, there was this interview with Obama where he’s talking about, he actually said something like, it was something light, like, oh, um, we have to watch out for fat cats on Wall Street. You know, and then all of his —

Rich: Do people still say ‘fat cat?’”

Paul: Yeah, I mean, Democrats do.

Rich: Yeah.

Paul: And you know, the investment community’s like, “This is like when Hitler invaded Poland.” [laughter] And you’re just like, you are such babies. Rich people hate when you say mean things about them.

Rich: Well, I mean…

Paul: And you and I are doing fine and people are saying mean things about us on Medium. I kind of like it, actually. I don’t know what’s wrong with people.

Rich: Yeah. Well I think the narrative that they kind of latch onto is that they’re misunderstood.

Paul: I know —

Rich: There’s a lot of —

Paul: Because they’re making so many jobs. They’re so good.

Rich: Right. Which is true. I mean…

Paul: Is it? Is a hedge fund guy making so many jobs? Are the hedge fund people who are just, like, constantly invading Yahoo —

Rich: This could be a whole other podcast, but I have a lot of questions about this stuff which would only confuse us even more, so.

Paul: All right, so Apple is…

Rich: Yahoo.

Paul: —fail…wait, Yahoo’s got…problems.

Rich: Well, I mean…isn’t it, I think, still the most visited home page in the world?

Paul: It’s just, it’s accounting is all weird…

Rich: I go there every once in a while, by the way, and it is really strange. You go to yahoo.com?

Paul: Rarely.

Rich: You don’t go that often?

Paul: Not so often.

Rich: First off, the colors, and just, the whole scene is pretty intense. So is Yahoo a failure? Is Mari — I mean, really specifically, people love to talk about Marissa Mayer.

Paul: I think, again, this is all about narrative. Right? She’s —

Rich: Yeah.

Paul: Who can really know, objectively, if this thing is a failure or a success?

Rich: Well what’s fail — what’s success? Let’s pause for a second. What’s success? Apple’s success is you have to keep growing exponentially.

Paul: You know what, you know, actually, that is, you’re —

Rich: What’s success.

Paul: There’s this big article in BusinessWeek. One of the things that Mayer truly, truly wanted to do was create great products, in particular mobile products?

Rich: Yeah.

Paul: And they don’t crack the top fifty on the iTunes Store.

Rich: Right.

Paul: So by that actual measurement, Yahoo currently is not able to ship great, global-scale, exciting mobile products in any way.

Rich: Right.

Paul: It’s really hard.

Rich: It is hard.

Paul: But they’re a giant company with huge resources.

Rich: Yes. And they can’t seem — so that’s success.

Paul: That was defined by her as the goal.

Rich: Oh, so she defined her own success. All right, that’s meaningful. That’s helpful.

Paul: That’s right.

Rich: OK.

Paul: But meanwhile, the way the market defines success around Yahoo is crazycakes. Like, they own Alibaba.

Rich: That’s where all their worth is.

Paul: And also, in Yahoo Japan. They have all these sort of like…they have a huge amount of ownership of non-core Yahoo organizations.

Rich: Right. And it’s a brutal scene, right? Like, the talent just leaves. Anybody that can go to Google goes.

Paul: Or Facebook.

Rich: Or Facebook, or whatever. So it’s just a rough, rough environment, where…

Paul: Well, I mean, you’re asking people to create start-ups inside of this organization.

Rich: It’s a vicious cycle.

Paul: Well, I mean, you’re in — look where you are. You’re surrounded by well-funded start-ups.

Rich: Yeah.

Paul: So psychologically that’s got to be a very challenging place to be.

Rich: Right. Exactly.

Paul: So that one probably is, by its own definition, failing.

Rich: OK. So, this is helpful. As we go down the list. Apple: not failing.

Paul: No, but there’s a narrative of failure, because people have to keep selling newspapers.

Rich: Right. OK. Yahoo: failing.

Paul: Yeah, not so good.

Rich: OK. So there’s this company out in the Valley, also, called Theranos.

Paul: Oh boy, this one.

Rich: Yeah. This company’s worth billions, based on the amount of investment that’s gone in.

Paul: Is that the one that has — it’s the woman with very intense eyes.

Rich: And like, the really strong turtleneck.

Paul: Yeah. Yeah, she’s in charge.

Rich: And here, we should give background. Theranos promised to…

Paul: Revolutionize blood testing?

Rich: Like, with a pin-prick, you could take a drop of blood and run a gamut of tests for a fraction of the cost of what it takes to run tests today, and time.

Paul: This is billions. Anything with healthcare multiples immediately, right? So…

Rich: Immediately. So she’s a Stanford drop-out, came up with this idea. And I don’t, whether she is well-connected or what-not, but got some very powerful people —

Paul: People were very excited, yeah.

Rich: But not just that. I think Kissinger’s on her board.

Paul: Oh, great guy! Really great guy. Good —

Rich: So I mean, you just need different perspectives.

Paul: Can we get him on the Postlight board? And maybe also just Satan? Can we get Satan on the board?

Rich: [laughter] All right. So…

Paul: Like a little dog? And a…some…and just burn it all down?

Rich: [laughter] Raises a ton of money…

Paul: Uh huh. Great.

Rich: And then it turns out, there were a couple things happening.

Paul: See, I’m done. Kissinger on the board?

Rich: You’re not buy —

Paul: Burn! That’s it. To hell with that company.

Rich: OK. So.

Paul: Did they do something bad?

Rich: So the Wall Street Journal does this big exposé.

Paul: Like destroy Cambodia? Did they do that?

Rich: They ruined a Far Eastern country, right. It turns out that they still use the old blood test machines.

Paul: Oh, so it’s like when you buy a USB hard drive from China and then you open it up and there’s no hard drive inside, there’s just like one little flashdrive with the two gig — like there’s all these ghost things that are out there in the world.

Rich: Something along those lines.

Paul: Yeah.

Rich: So it was already, there was already sort of a sense of —

Paul: So they were using old tests. They were saying, like, give me that pin-prick, but they were using the old system?

Rich: Yeah, and their answer, their response to that was, well we’re still working it out.

Paul: Ohhhh.

Rich: [laughter] Or something along those lines.

Paul: All right. So that was bad.

Rich: And in addition —

Paul: Like, the alarms start going off right then.

Rich: It was a bad reveal.

Paul: Are you sure Kissinger’s on their board?

Rich: Yes, I’m pretty sure he’s on their board.

Paul: [long sigh]

Rich: Or involved in some way…

Paul: Why is he doing anything? Like —

Rich: Kissinger’s semi-retired, dude.

Paul: I know.

Rich: This was interesting.

Paul: But his job is to feast on babies. Like, that is his only real responsibility.

Rich: Do you view him as very evil?

Paul: Kissinger???

Rich: Yeah?

Paul: You don’t think he’s got some problems.

Rich: Was he secretary of state?

Paul: Yeah.

Rich: You can go down the list of every secretary of state, and they all have dead babies on their hands.

Paul: Mmmmmmmmmm….not like….

Rich: Pretty much.

Paul: Cambodia?

Rich: [sigh]

Paul: All right. Let’s move on. We’re talking about technology. Not genocide.

Rich: Is Kissinger a failure?

Paul: Yeah. Yeah, I would say that our overall strategy as a country engaged with Vietnam and Cambodia? Probably not optimal.

Rich: OK. So we’ll add him to the list.

Paul: OK.

Rich: All right. Apple: not failure. Yahoo: failure. Kissinger: failure.

Paul: K.

Rich: Theranos. Now there’s criminal investigations taking —

Paul: Are you sure it’s Ther-AH-nos, and not THER-a-nos?

Rich: Uh, I don’t know.

Paul: It could also be, like, [a Greek accent??] TER-a-nos.

Rich: I don’t think it’s a gyro joint.

Paul: I don’t know. We’re talking about Chobani. Could it merge with Chobani? [laughter] Could it be Theranos/Chobani?

Rich: Uh…

Paul: You just put a prick of blood into your yogurt.

Rich: I would — I think there’s something interesting to talk about with Theranos.

Paul: [very dramatic Greek accent] Theranos!

Rich: [ditto] Theranos! Is that —

Paul: Funny accents are problematic, I just want to state that.

Rich: She could’ve proven this out with a hundred million bucks.

Paul: Sure.

Rich: Or fifty million.

Paul: Sure.

Rich: That’s a lot of money. You get some PhDs, you get going, and you prove out your promises.

Paul: You just get, like, one guy and prick the shit out of him, and then you see if he survives.

Rich: Instead she —

Paul: The plot of Dune.

Rich: [laughter] She raised an outrageous amount of money because success, like, essentially she decided to draw the goal line way, way out, which is, I’m going to change the game.

Paul: Ah yeah, OK.

Rich: So I’m not gonna lie: I’ve seen pictures of this —

Paul: She’s an intense person.

Rich: Intense person. Kinda freaks me out.

Paul: I’ve seen some videos with her. She expresses herself while looking directly through the camera, into the back of your head, where your brain starts to actually catch fire.

Rich: Yeah.

Paul: From the pressure of her eye…sockets.

Rich: And this raises something else, dude. We like to gawk at this stuff.

Paul: Aw yeah. This is a hobby!

Rich: Stuff slips up. When Yahoo slips up, when this one slips up, there’s a scandal behind it and whatnot. It’s sort of the flip of it, right? You were talking before about how success is, we’re out of our minds —

Paul: But this is different.

Rich: Defining success —

Paul: This is different, this is different. If you’re, like, a ten-person, or five-person, or one-person start-up, and you give something a go for eighteen months, and you gave it your best, you gave it the college try, and it blows up, and you sit there — see, that’s the weird thing, because that’s who sits there in a room going, “I don’t even know how I’m going to go on. I hate my life. I failed completely.”

Rich: Yeah.

Paul: And then there’s this sort of thing that happens at very, very large scale, where there’s always a narrative where it’s not a failure. Like, if you get up to, Marissa Mayer, you know what happens, they always —

Rich: Is it Meye-er or May-er?

Paul: I have no idea. It’s Theranos.

Rich: OK.

Paul: These people, I love it when, like, really high-powered CEOs, something goes terribly wrong, and then they go off and they do the next project?

Rich: They just leave.

Paul: They leave, and then they’re like, they can’t go get another CEO job right away.

Rich: Yeah.

Paul: You gotta get out in the wilderness a little bit.

Rich: Yeah.

Paul: Like when editors get fired from big magazines, typically they go teach at Columbia Journalism School.

Rich: I see.

Paul: And then they get another job. Or like, when Al Gore —

Rich: They take a hiatus.

Paul: Yeah. You go, you go somewhere.

Rich: Right.

Paul: So they go and they build that app, or they build that company, and it’s always a disaster. It will always sort of be like, “Oh it’s a social network platform.” Or, you know, it’s audio recognition, but it lets you communicate with cats.

Rich: Right.

Paul: Something like that. And then they, because they’re not surrounded by their people anymore, and they’re going to express their true selves.

Rich: Right.

Paul: It’s like when that guy from Groupon went and made an album.

Rich: That’s right. It’s funny — there’s an irony to all this. We had Dean Hachamovich on here a few weeks ago, and he was telling us that he likes to boot up his Mac with the console up. You know, the OSX is spitting up all kinds of errors as he’s booting up probably one of the most buttoned-up, or if not the most buttoned-up operating systems in the world.

Paul: You’ve got gigs of software.

Rich: Gigs of software, widely used, pretty pristine stuff.

Paul: Apple knows that it ships a broken operating system every time. I love those updates, too, you get, where it’s just like, “Improves the security and stability of you system.”

Rich: Yeah, exactly. Meanwhile they’re plugging a big, gaping hole.

Paul: Yeah, exactly.

Rich: That’s been bleeding —

Paul: —your credit card information.

Rich: Right. Into Eastern Europe for months.

Paul: Those guys are great, though.

Rich: Yeah.

Paul: If you’re gonna get hacked…

Rich: But you know, I think that’s the chase, isn’t it? Like, software’s sort of a reflection of our own flaws, right?

Paul: Ah, it’s —

Rich: It’s all broken.

Paul: It’s a garbage tornado.

Rich: It all could be rewritten. I don’t think I’ve ever met an engineer, who, if I’ve asked them to take a look at someone else’s work, has come back to me and said, “This is great. I just want to change a couple things.”

Paul: No, typically what they say is, “This is a war crime.”

Rich: This is a war crime. Give me three weeks.

Paul: Yeah.

Rich: And I’m gonna re-do this for you.

Paul: If this was written by an animal, I would euthanize the animal.

Rich: Yeah. And I guess it’s the human condition, right?

Paul: And the other thing, too, right — so I had this experience. I was the editor in charge of the website for Harper’s Magazine for five years.

Rich: Yeah.

Paul: And when I went in, I went in in 2005, and the web was in a different place from when I left in 2010, and I built this big archive, and I did it, there were very few resources, and I did it entirely by myself.

Rich: OK.

Paul: So I wrote all the code, and I wrote it, and I used the wrong database. I made a lot of bad decisions.

Rich: OK.

Paul: So I left and I was kind of lingering. I was there kind of part time, no one could figure out what to do. And this guy came in to replace me. His name was Jeremy Keehn. And I didn’t want to talk to Jeremy. I didn’t want to deal with him. I didn’t want to deal with my replacement. But he’s like, look, I’ve gotta normalize what you’ve done. And he wasn’t as technical as I was. They hired an agency. They did it right. Or as close to right as they could afford to do.

So I was like, “All right, just whatever questions, just ask.” So what would happen, at first the questions were kind of like, “Ugh, what have you done?”

Rich: Yeah.

Paul: And over time, and I would explain how I’d come to this conclusion, and over time, he and I developed this friendship where, at a certain point he’s like, “As I’ve learned to expect, there’s always an eminently reasonable answer to why ended up in this situation.” And sometimes it was business, sometimes it was technology, sometimes it was just my ignorance.

Rich: Yeah.

Paul: And I would be like, “Oh, I didn’t know what the hell I was doing.”

Rich: Yeah.

Paul: Or, something would just slip, or whatever. It took, like, almost six months, but over that time, I was able to justify myself, but also explain, like, I’d gotten into this without complete knowledge, and this is how it ended up that way? And we ended up building a really, like, a good friendship.

Rich: Well, you’re an exception.

Paul: But I was still in the room.

Rich: Nine out of ten times there would’ve been a PR campaign by that person to cover up the bad and really emphasize the good. That’s how it works. We do this our entire lives. I mean all of LInkedIn is a coverup of all the crap I did wrong.

Paul: True.

Rich: The whole thing. I mean, the resume is the highlights of the good. We should have mirror of LinkedIn of all the screw-ups that each person has done throughout their lives, because that, if we’re willing to embrace those kinds of mistakes and flaws and shortcomings, you know, I think we could be happier.

Paul: See this is the thing, too, there’s this sort of very easy-to-make criticism that you can’t define success or failure by money, right? People say that all the time.

Rich: Yeah.

Paul: That it’s happiness and so on. And I get that, and I respect that, but —

Rich: The Atlantic every two years taps me on the shoulder and explains to me why I’m not happy.

Paul: Yeah, that’s good.

Rich: [laughter] Every two years.

Paul: Or you’ll be happy if you have kids, or people without kids are actually happier, whatever. The issue, to me, is that failure and success are oddly meaningless categories.

Rich: Hmmm.

Paul: Some things really do succeed in the most obvious possible way, like, you know, Facebook is a big social network that makes lots of money. It’s a very easy story to tell.

Rich: Yes.

Paul: But the reality is, you know, the work I did at Harper’s was weirdly successful.

Rich: Yeah.

Paul: When it was inherited, it became a failure, because it was so hard to work with. It wasn’t malleable and —

Rich: Did you feel successful, did you feel like, today, when someone asks you about that —

Paul: I feel like everything I do and everything I touch is a failure.

Rich: Which is probably what motivates you.

Paul: Yeah. I want to get, I want to get there.

Rich: That probably explains a lot of your success.

Paul: Oh, without a doubt. I’m never happy. I’m never going to be happy, ever.

Rich: And that’s the story, isn’t it?

Paul: That’s one of the things, I think that’s tricky, it’s one of the things I’m learning since we started this company, as a manager, I’m trying to keep that from leeching into the water supply.

Rich: Yeah.

Paul: Because we have lots of people who are dissatisfied with the work they do. They always want to be better. We definitely hire strivers, right?

Rich: Yes.

Paul: I know this about you, and I know this about myself, like, I’m not satisfied.

Rich: [sigh] I mean…

Paul: The experience that I want, the things I want technology to do, the power that I want it to distribute out into the world, is not yet accessible.

Rich: Yeah.

Paul: I should be able to take ideas I have and distribute them in new and exciting and novel ways. I’m talking at this very high level of abstraction —

Rich: Yeah.

Paul: —but that’s where my head is. I’m not feeling that yet.

Rich: Yeah.

Paul: Out of the world of tech. And so I kind of roll my eyes at a lot of people running around telling me how great something is, when the fact is, I can see, and I’ve been able to see since I was a kid, and if you go back to the sixties and seventies, people could see these very empowering, augmenting devices, and we’re nowhere near it. We’re nowhere near what technology could do to make human beings smarter.

Rich: Which is probably why there’s this chase, right?

Paul: Yeah.

Rich: I’m going to change the game. I’m going to change the way you get a cab.

Paul: I actually don’t even need to be the one to change it, I just want to be there. I want to see it.

Rich: Fair.

Paul: I want to see how this turns out.

Rich: Yeah.

Paul: Because I feel we’re in the middle of a giant landslide.

Rich: See, I thought the outcome of this podcast would be, everybody needs to chill out, pour a glass of wine, and just be happy.

Paul: Screw that. Screw that.

Rich: But it turns out that we’re just in the part of the game where there’s such massive potential that we just can’t help but chase it. We always feel like we’re behind.

Paul: Look, I mean, one of the things I talk about and think about a lot is how can we go faster? How can this company go faster? And not glossing over things, but when you meet good programmers, you meet good designers, they’re people who focus on ways to do the same thing again more efficiently.

Rich: They’re also such a source of energy, right?

Paul: Yeah.

Rich: And that’s…inspiring, and that’s motivating, and…

Paul: That’s right.

Rich: And you’re like, wow, let’s get in a room and just whiteboard this for a second. And then the excitement just kicks in.

Paul: Really smart people just accelerate everything.

Rich: Yeah.

Paul: And that is fine, and we are kind of back to what we were talking about, which is like, we need a certain amount of stimulus, we need a certain amount of engagement to feel success. We’re chasing it.

Rich: I don’t know if that stops.

Paul: The balance is the hard part. I don’t think it’s about us sitting on the Riviera drinking glasses of wine and thinking about the sunset. I think it’s us, you know, you’re doing good, you’ve started going to the gym more regularly, I think you’re finding a little more balance. I’m not there yet. I got real deep in, and now I’m trying to figure out how to pull it back a little bit —

Rich: Balance it out.

Paul: —and find a little balance. Yeah.

Rich: Yeah.

Paul: Because I don’t, I wake up and I go to sleep thinking about the company.

Rich: Yeah. I just love that this podcast turned into a therapy session. I feel better. I don’t know how you feel.

Paul: I feel like I have to go out and do something right now to change the freaking technology world again.

Rich: Let’s go.

Paul: Let’s do it!

Rich: All right. Ironically, I think this has been a success.

Paul: This episode?

Rich: I’m not gonna specify.

Paul: Uhhhhhh…I could think about five or six ways it could be better. No, I’m not gonna list them. But every time we do this…

Rich: I grow, as a person.

Paul: [laughter] I grow frustrated. I just want to…I can’t help it. I can’t help it. There’s always a way to do it better. I feel that I, you know, I have this public voice. It’s a little bit soothing.

Rich: Well you’re so ego-driven, that’s why.

Paul: Yeah. I’m just a narcissistic lunatic. [laughter] But I have this public voice and it’s, I’m very soothing, I’m like, “Hey you can learn how to code,” and so on and so forth. And at some point I also really do want to tell people, like, “No, you’ll never be satisfied. It’s never done. You’ll never learn enough.”

Rich: Yeah.

Paul: Anyway, we should, we should probably go.

Rich: On that note.

Paul: I’ll…let’s walk back to the office, get some work done.

Rich: Let’s do it.

Paul: Everybody out there, thank you for listening. You know, if you want to, rate us. If you don’t, if you just want to keep listening, that’s chill, too. It’s all good.

Rich: [email protected].

Paul: [email protected]. We’re getting a lot of questions together, and we’re going to answer them all at once real soon.

Rich: Thanks everyone.

Paul: Thanks. Talk to you later. Bye!