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Episode 155 February 19, 2019 | 34min

What Harper Reed Thinks: A Conversation With Obama’s Former CTO

Techno-futurist hacker Harper Reed reminisces with Paul and Rich

Show Notes

A Creative Path to Find What’s Next: Harper Reed could have listed his many accomplishments on the historical monument he installed in his parents’ front yard. It could have said that he founded Modest, a mobile retail startup eventually acquired by Paypal, or that he was CTO of Threadless and the 2012 reelection campaign of Barack Obama. Instead, he and his brother Dylan chose to commemorate their exploration of Uranus.

It’s no wonder Rich often hears Paul say “I wonder what Harper Reed would think.” In this episode, the pair talk to Harper about his dad’s Apple IIc, coming of age during “the most rapid capital expansion in the history of the universe,” political tech, mobile commerce, and what comes next for the defiant technologist.

Harper Reed The real reason—the real thing is we couldn’t figure out a name, and so we called it Lunar Technology Company. Cuz we were like, “That’s a fun name.” And I went to a conference and I had this badge that said Lunar Technology Company and this guy says, “Ah!!! You’re one of the people that are mining the moon!! There’s a group of you over there! You should go meet all the rest of you.” And I was like, “We need to change the name of this company.” [Paul and Rich laugh, music fades in, plays alone for 18 seconds seconds, ramps down].

Rich Ziade I met this individual . . . I think it was three years ago.

Paul Ford Uh huh.

RZ Maybe around then. And for about seven minutes.

PF K.

RZ And it felt like I just got introduced to a kaleidoscope.

PF Yeah.

RZ And it was a bit of a tornado and then, for some reason, [music fades out] I found out my jacket was on backwards and then he left.

PF Let’s be clear! Technology is an interesting industry that doesn’t always inspire the most exciting people to join it.

RZ And passionate people.

PF Yeah.

RZ Uh.

PF Like people who are a little weird and a little off kilter and [yeah] a little punk rock don’t always go into global technology and scalable horizontal technologies.

RZ Correct. And then every six months or so, we’d be talking through some problem or some opportunity or whatever it may be, and Paul would say, “I wonder what Harper Reed would think.” [Laughing] Like every few months. Like, “We should get his opinion on this.” So we have Harper Reed today. And Harper, before we get into it I just wanted to do a little homework and you have this timeline—I think it’s harperreed.com [yup] is that correct?

HR Yeah, that’s correct.

RZ And it’s very entertaining. You should go through it. It—it goes—it dives deep into sort of, “Oh I took a walk,” and then swoops upward into [Harper chuckling], “I’m doing stuff for MIT.” And it’s really entertaining.

[1:50]

PF You know here’s where I’m at with Harper: he ran a big chunk of the Obama campaign on the—on the tech side.

RZ Uh huh.

PF And he also started a merchant focused startup that was acquired. He’s a—he’s really a serious tech player but he also wrapped, with his brother, he wrapped his parents’ car in a—in like a zebra wrap . . . while they did—as a prank.

HR Oh yeah. That’s not even the good one, I think.

PF What was the good one?

HR [Chuckles] The good one was when we—we—I’d been going to London a lot for work and I noticed all these houses had these like plaques on ‘em that said like, “Boyhood home of some famous person I hadn’t heard of,” or like, “Jimi Hendrix lived here,” or whatever. And I always—I always thought that was cool, like it was neat to see the history in a normal neighborhood, and so my parents went on a vacation and we put a monument in their front yard.

PF How big was the monument?

HR Well it’s on about an 800 pound rock right in the front yard and it says, “The boyhood home of Harper and [Paul chuckles] Dylan Reed, the first astronauts to explore Uranus.” [Hosts laugh]

PF Wow. So both incredibly complicated, difficult, operationally frustrating and then unbelievably immature.

HR Unbelievably and it’s so funny because, of course, my father comes home from their vacation, they see this rock, they look at it, they chuckle, and then my dad goes to lift it to take it to the backyard and it’s just like nope. It’s gonna [Paul laughs wheezily] be there.

RZ [Paul continues laughing] Is it still there?

HR Yeah! It’s gonna last 60 years based on the spec of the plaque.

PF What does your father—when you’re—when you do something like this to your father and mother, how do they—what is the first thing they say?

[3:22]

HR Well, it depends. When we wrapped the car, they were also on vacation when we wrapped the car and—

PF Ok and tell—tell the people what you actually did here.

HR So, my parents went on vacation; they just got a brand new Ford Flex and they were really proud of this Ford Flex. So, they went on vacation maybe two months after they got it, they drove somewhere. And so my brother takes the car, goes to the sign shop, that we pre—that we talked to and they wrap it like they wrap the whole thing as a zebra, zebra-striped. And we went through a lot of iterations on how—

PF Like a plastic wrap, stuck to the car.

RZ Wraps are hot!

PF Yeah.

HR Yeah, like, you know, you see the cars on the street that have advertising or they’re—

RZ Buses. Yeah.

HR Yeah, exactly. I think that—that’s where I got a lot of that inspiration was it’s actually not that expensive. I mean it’s a couple thousand dollars but painting the car seemed—

PF But the look on their little faces is worth it.

HR No, no, that was exactly it. So we wrap it, we put it in the garage, we put a couple Dropcams up around, and then we wait for them to come home, and it was nerve-racking because we didn’t know exactly when they were gonna be home but we wanted to be able to see the reaction.

RZ Capture it. Yeah.

HR Eventually they got home, my father just opened the garage, saw his zebra car, and shut the garage. It was just like [Rich laughs], like, “Maybe—maybe if I open it again, it’ll be different.” [Rich laughs] He got it. And my brother made one flaw which is he left the Dropcam boxes on the kitchen table. So my dad immediately knew there were cameras. And then he called me and just said, “Revenge is a bitch,” then he hung up.

PF Wow.

RZ [Laughs boisterously] Your da—your dad’s been watching action movies [laughs].

[4:54]

HR Well—well, it’s funny because—because I think actually they really like it. I think they—I think they kinda look forward to it because it’s fun and it’s funny and—

RZ Wait, they peeled it off though?

HR Well they kept it for about two years until they hit a deer [hosts laugh]. Yeah so they drove around in this [chuckles] Ford Flex for two years as a zebra and my—my dad would get really angry—we’d be driving and he would just be like [through clenched teeth], “Why is everyone looking at me?!?” We’d be like, “You’re in a zebra car.”

PF Ok. So—

RZ Wait, wait, so—

PF No, that’s fine—

RZ For those that don’t know Harper, the [stammers] narrative should go to, you know, Harper keeps borrowing money from his parents cuz he’s gonna make documentaries.

PF [Chuckles] Yeah.

RZ But that’s not what happened—is it, Harper?

PF He’s actually—he’s actually a very serious technology leader [Rich laughs boisterously].

HR I was just gonna say [Harper], there’s—there’s websites for all of ‘em.

PF On that note, what was your first computer? How’d you get into this business?

HR My first computer was an Apple IIc [pronounced two-c] [ok]. I had that—I had taken a kind of college for kids type of Apple programming logo, of course, and then [mm hmm] my aunt who is only seven years older than I am, went to summer camp for Apple computers at the local college and I kinda looked over her shoulder, and then one thing led to another and somehow my father got two Apple IIcs and my brother and I set ‘em both up.

RZ That’s so cool.

PF Ok, so, did you stay sort of like a technology person or did you like start a band? What was your—

HR Well, I started a band with the technology kids.

PF Perfect, actually.

[6:16]

HR Yeah, I mean I didn’t have a choice. Like, computers just drew me in. I mean oftentimes I find there’s a tension here. You know, those of us who grew up during this age, where you have an Apple II, and you use computers your whole life, I think there’s many of us where we just didn’t have a choice, this is just what’s was going to happen: we were going to use computers; and we were going to do technology. When we talk to young people today they just don’t have—we can’t—there’s—we can’t identify with them, it’s an incommensurable experience. Where when—

PF [Interrupts] It’s not just that. We also came of age during the most radical capital expansion in the history of the universe, right? So it’s sort of like, wherever you went, if you had this raw set of skills, there was kind of something for you to do that would be useful and interesting and could probably make you money.

HR Right. And I worry—I worry that the kind of the trope of, “Let’s teach kids the code,” I think it’s good because it’s good for people to have, like, general skills in logic, et cetera. But the idea that this is going to give them the same kind of experiences in capitalism that many of us had, I don’t think is true. And I worry that—

PF No—

RZ No—

HR—we’re setting up a path to factory worker.

PF There’ll be some new color, like ‘grey collar’, or—

HR Yeah.

RZ I think the distinction here is that you could go places you weren’t supposed to go on those old computers. It wasn’t [yeah]—like Minecraft, God bless it, but it was—you’re in that world and it’s pretty—you know, it’s shrink-wrapped, and you’re gonna be inside that box, whereas I, you know, when I first opened up a Hex editor, I didn’t understand, “Wait a minute, I can go into the Hex code of my game?” I didn’t know why I wanted to be in there and I wanted to screw around. And that sort of open endedness, I think, you know, breeds creativity.

PF That’s pretty—that’s levels down, too. There’s also like Photoshop taught you how [yeah] color and photography and light work and—and like you would pirate these wonderful tools and then you’d see how adults lived in the world and did things by playing with the software.

[8:02]

RZ I got obsessed with the 4K demos in the beginning of the pirated . . . games.

PF Right.

RZ I—I loved what they were doing with such little information, it was so cool.

HR Yeah.

PF So, fast forward: one day Harper, who was somebody who was kind of extremely online, who we all knew, was running tech for the Obama campaign.

HR It was a surprise to us all, to be honest.

PF Ok. How did that happen?

HR So I was at Threadless and I decided I was done. You know that feeling when you’re—I described it then as when you’re at a dinner and you’re just full. That’s kind of my feeling about Threadless. I was like, “I’ve accomplished everything I wanted to accomplish. The problems that they have aren’t interesting,” like et cetera, et cetera. So I just kind of peaced out and then I—I just went to coffee shops and hung out and kind of screwed around Chicago for awhile. And, in retrospect, what I had done is I had made myself incredibly open to new ideas and new opportunities. And so one of ‘em was a friend of mine who happened to be Republican said, “Harper, you should talk to this guy, Michael Slaby, who is CTO for Obama’s 2008 campaign and he’s looking to build up a team, you might be able to help out.” And what I had done is I just met up with Slaby at a coffee shop, we just chatted a bit, and I was like, “Hey, I have a team,” because I kinda had been collecting these people because I knew I wanted to do something and I wanted to do something big and I didn’t know what. So I had a team of designers; and programmers; and user experience people that were just kind of waiting in the wings. And he’s like, “Great! We definitely need all those folks and we also—we also need a CTO type person.” And I was like, “I have—I have—Great, I have some of those, too,” and so I recommended a few friends that I thought would be great CTO type people. And introduced them and then I kinda stepped off and just was like, “Ok, cool, continue doing what I’m doing.” But then one thing led to another and I um—and Slaby was like, “Yo, you gotta talk to this guy, Jim Messina, who’s a campaign manager,” and Jim Messina is a pretty—he’s an imposing figure. He’s just kind of insane. He seems like a TV character, really. Um and so I’m talking to Jim Messina and he gets a phone call and he was just like, “Just a second,” he answers the phone call, he’s like, “Hey, I gotta call you back, I’m in—I’m currently in an interview with a CTO candidate,” and I’m just like looking around my shoulder, trying to find where the CTO candidate is because I had no idea at this point that I had been [chuckles] interviewing for CTO for probably like a month and a half. I just didn’t know. It was like my confidence wouldn’t let me know that. And then I talked to my friends afterwards and they were like, “Yeah, dude, what’s [chuckles]—what’s wrong with you? Of course you were interviewing for CTO,” and I just didn’t know. Like I really didn’t know [Rich laughs]. I never previously said that. But at that point, once that happened, then it became real serious and it was like I find that there’s a bunch of points in my life where if it was filmed it would be that point where they zoomed the camera in and pull it back at the same point or whatever, like in a horror movie, you know? Where it’s like, [in spooky voice] “Oh no!!! I’m gonna get a job!” [Hosts laughing] And so then I’d been saying no to so many opportunities and so then the thing was, “I don’t think I’m good at this. If they give me this job, I have to say no.” And then they ended up giving me the job, they said, “We want you to be CTO,” and I was just like, [sing songey] “I don’t know.” And my dad was like, “You’re gonna be the CTO, I signed the papers already,” like my—Hiromi, my partner, and my father were like, “What’s wrong with you?!? Of course you’re gonna do this job!” And I just didn’t have the confidence. I truly—this was a true confidence issue. I just didn’t have it. And then one of the reasons why is . . . I kinda knew the job was gonna be different than Threadless. But, at Threadless, they had said, about a year before I left, they were like, “Harper, I don’t think you’re doing a good job as a CTO. We need—” And then they gave a catalogue of things that they needed that I was not providing. And I said, “Well, I thought a CTO would do this and I gave a catalogue of all the things that I was doing very well.” I’ve later seen that both are right. I was just a different type of CTO than they needed and the campaign was 100 percent of the things that I wasn’t doing at Threadless. Like it was really funny, actually, cuz I was like, “I’m never gonna do Excel modeling. I’m never gonna do budgets! That stuff’s stupid. I’m wanna program computers.” Then at the campaign it was like I never programmed computers once, you know, I couldn’t—they wouldn’t let me because I’d screw it up but, more importantly, I was doing all this modeling, most of my time was in email and Excel, doing meetings—kinda what amount to board meetings. It was actually an incredible experience but the beginning was a little bit Dick Cheney-like in that I didn’t really know I was being considered until suddenly I was the CTO.

[12:03]

PF And it helped you knew that it was gonna end.

HR Absolutely! In retrospect, I don’t think it actually matters. I think maybe emotionally there was something there but you jump so far into that type of thing that you cannot get out. Like it doesn’t matter if it’s two weeks or 18 months, it’s just you’re so deep it could—you could be there for four years and never know.

RZ I don’t wanna go off on tangent but I gotta ask this question. Obviously over the last ten years, technology has rendered itself integral to politics and campaigns . . . Gimme your perspective on this, now that we’re looking back.

[12:38]

HR Well, it’s actually—I think it’s actually pretty straightforward. You just look at the—the year, the presidential election years, and you think what technology was popular then. If you look at when social software happened, that’s when it starts to get interesting. So, 2004, social software was then. Right? There was a lot of stuff happening . . . but for the most part it was really um, you know, Flickr, et cetera. It wasn’t meetup—it wasn’t . . . there wasn’t a lot of communication socially. It was still private kinda little groups and networks. For instance, IRC was still a relevant thing for tech people to hangout on. But 2008 is when things started to change: Facebook was there. And you could use that for organizing in some ways. Facebook pages were kind of created because of Barack Obama’s Facebook account had too many people. Android had just launched. The iPhone [stammers] apps had just launched. Twitter had been around but was kinda still for just hippies. You just had like all these things that were so nascent. And then four years later, in 2012, everyone was using these things. You know, my parents were using these things. They had matured to a point where they were normal. And so I think the narrative is just it trails four years behind regular technology, maybe two years, but there’s a couple of other things that happened that I think is really weird. In 2012, when we were building all the stuff we were building, we were looking; we were scouring the earth, looking for cool ways to connect technologies to organizers, et cetera. That kind of vibe. And we looked everywhere. I remember thinking, like, “Here’s a catalogue of the things that we have found from ad agencies, from cool brands, from, like, you know, to influencers to startups to whatever,” things that we—things that are influencing us. And then we had built things based on this. And when we came out of that, we were like—like I remember talking to an ad agency and they were like, “How did you think of all this stuff?” And I was like, “Well, actually, we just looked at ad agencies,” and they were like, “Yeah, but no ad agency does this stuff.” And so I don’t know how this happened; how we looked and we thought we were reflecting back things that other people were doing, and then it turns out that we were inventing. Because we all thought we weren’t inventing. We purposefully said, “We’re not inventing. We’re trying to win. This is not about innovation. This is about trying to win.” You don’t win through innovation. You win through consistent experiences and, you know, and very, very solid experiences. But, you know, in retrospect, we’d—we’re innovating. And I think that kinda happens in every one of these campaigns, where they say, “No, no, no. We’re just trying to win. We’re gonna use only this thing because we don’t have any money or what have you.” And then that itself is innovation and that’s where it deviates and seems innovative. I’m sure if you look at Brad Pascalli [Parscale] or however you say his name and the Trump stuff that the work they did on ads on—on landing pages and all that stuff just was kinda—they just needed to do it because they—they didn’t have any other toolset. In the same way that social software and community software was my toolset, this was Brad’s toolset, and so that’s what they did. Now that seems like it’s part of a playbook but I don’t think it started out as saying, “This is part of a playbook,” you know, I think it’s just kind of by any means necessary.

PF “I found a hammer on the floor.”

[15:33]

HR Yeah. Yeah. And—and the thing [yeah] is is every person that runs technology finds a different hammer. So Steph from the Hillary campaign had a different hammer than I had a different hammer then Slaby had a different hammer; Joe Rosebars had a different hammer in 2004. Like it’s like all those kinda things that you have different hammers and I had a very strange, strage, strange, strange conversation with Karl Rove once which is a weird thing to even say, where he was describing his hammer is direct mail.

PF He had a direct mail company at one point.

HR Right! And they—he talked [yeah] about how they used analytics in the same way that we use analytics, the same way that 2016 used analytics, to target people but with direct mail. And so it’s—your hammering analogy is perfect. It really it whatever hammer you have is the one you’re gonna use and if you win then suddenly that’s how you do it. And I think that’s the silly part is how oftentimes the playbook is written by the winner. And I think David Axelrod has a really good kinda statement as this which is, “You’re never as dumb as they say you are when you lose and you’re never as smart as they say you are when you win.”

PF Right.

RZ You feel like these amazing tools, which, you know, I feel like four years ago, five years ago, three years ago, were viewed in a very optimistic light, as empowering and—and—and just really a positive pivot in the world of politics is gone to a dark place or a—a place where, you know, all sorts of ethical questions get raised and the like.

HR Yeah and I think it’s—nefarious is the wrong word but I don’t know better. I think it’s a little more screwed up than that. Because in 2012 we did a lot of the same stuff that Trump’s team did with Facebook, you know? We made cool Facebook ads for targeting people and we used all this neat stuff and we used all this technology and we used all their targeting stuff but since we won and largely tech people are progressives, everyone was like, “This is great! Harper, you’re a genius! Your team is amazing,” but then as soon as you lose they’re like, “Oh my gosh, this is the worst thing in the world.” And it really struck me that although we didn’t do the same thing that—that the Trump team did—like because there’s four years difference and we all know how technology changes, we definitely set the foundations.

RZ Sure!

HR And if we look at some of the complaints we have right now, about the 2016 election, you know, outside of Russia and all that nonsense, outside of Trump being a Nazi and all that stuff but more the specific parts of like how technology was used to trick people online, you know, I think we have to address all sides of this. Because it really is—the thing that bothers me the most is that we are very against it if we were tricked—if we feel tricked and by tricked I mean if we lose. But we’re very for it if we win. Now I think that’s fine as humans but if we’re trying to make a regulation or something, we should just be thoughtful about what that actually means and what that means about how we’re going to impact things.

[18:11]

PF So 2020 is something to look forward to.

HR Yeah, we’re all—we’re all fucked. I know we’re not trying to say that word [music fades in] but I think it—it’s important right now [music plays alone for six seconds, ramps down].

PF Hey Rich, lemme interrupt this podcast and ask if you needed [music fades out] to get a big, scalable web platform with applications built on top of it, who would you call?

RZ I would call Postlight.

PF I would too. And I don’t just say that as the CEO of Postlight.

RZ And I don’t just say it as the President [laughs].

PF I say that because, you know, just as we sit here and talk about this on the podcast every single week, that’s what people do here. Like we care and think about software all the time.

RZ It’s a great group of designers [yeah], engineers, product leads working together, by the way, there’s no throwing it over the wall. It’s a collaborative process and we—we’re designed and we’re tuned to ship.

PF Collaborative with our clients, too. A lot of Slack channels. Like right now I could turn my head around and there’s like ten Slack channels open [yup] where people are talking directly with the clients all day, getting this thing right.

RZ And clients are saying things like, “Wow!”

PF [Chuckles] Yeah they’re saying—[Rich laughs] Sometimes—sometimes we send the animated GIF, and then sometimes you know you’ve succeeded when the client sends an animated GIF back.

RZ Yes, it’s a wonderful thing.

PF So if you wanna send us an animated GIF expressing your happiness with how—how hard we’ve worked for you, you can just send an email to [email protected] Let’s get [music fades in] back to the podcast [music plays alone for eight seconds]. Let’s fast forward, right? Because after [music fades out] the—after all the politics are done, you decided to do something relaxing which is do a startup [Harper chuckles] focused on ecommerce.

[19:50]

HR That was—that was such a mistake. I—I—

PF What were you doing?!?

HR I find that I’m really good at being like like right now I’m not really doing anything, I’m taking a break, I’m trying to figure out—well, it’s giving myself space to figure out what the future holds and right after the campaign, we jumped right now. And I know why. But we jumped right in. And there was like a couple, like, weeks where we didn’t really know what was going on but we jumped right in.

PF And what was this called? What was this thing?

HR So, we—I have a friend who’s a domainer and she’s wonderful. And um I pinged her and I was like, “Hey, you know, we are looking for a new name brand for our company, you know, what do you got?” And she sent me this list of domains that was incredible and modest.com was there and so we bought modest.com. And then we went to Fuzz Co., a cool branding agency, and we said, “Hey, can you help us brand this?” And then they helped us brand it and it turned out to be—it worked really well.

PF How much did Modest[.com] cost? Do you remember?

HR Uh probably about 40K.

PF That’s actually—I mean for a name like that that’s great.

RZ Cheap!

HR We—and the reason we named it Modest, the reason why it fit so well is because from the very beginning we talked about how to make a big impact in ecommerce you didn’t have to do a lot of work, you just had to do really good work. And so we’d say, “We’re just trying to make some modest changes.” Um which is kind of silly and funny and then the logo was just a gradual slope and so that was this idea of like, “We just wanna make things better by making some small changes to ecommerce. We’re not trying to do this—like a bunch of crazy stuff.” Um—

PF Wait, what was it? What was it? People need to know.

[21:18]

HR Yeah, so um Modest was a platform for mobile commerce, right? It was mobile only. So, conversion rates were pretty good on it. It had all the experiences you would normally have in an ecommerce experience. So the idea was we would go to a boutique, we would go to, you know, someone who’s selling online and they would use our platform to power their mobile side. Mobile web, apps, and then we also had some really fun stuff like, you know, direct from email conversions, all sorts of kind of fun things where you’d click on a link and you’d just—you just—it’d just say, “You’re done. You’ve checked out.” Because we were—we were like—we thought—there was this funny thing and Dylan, my cofounder, Dylan Richard, he always talked about how sil—how silly it or how defensive and technology and ecommerce is specifically every time you go to check out it’s always like, “Are you sure you want to?” It’s like someone is trying to stop you from checking out, that’s basically what ecommerce is on the internet. They’re just like, “You don’t wanna do this.” You know, you put something in your cart [Rich chuckles] and they’re like, “Are you sure you wanna do that?” You go to like, “I wanna buy this.” And they’re like, “Are you sure? Why don’t you enter your address four times to prove that you wanna buy this?” Um and that was basically the interface and you see this still today. I mean, I think Shopify is probably the best right now. And even Shopify, there’s a lot of steps that I do over and over again, and it’s like, “You know who I am, Shopify. Why don’t you just make this easy?”

PF You built this—you built this nice company and then one day some of the friendly, young people from PayPal came by . . .

HR [Chuckles] We were at this point with the company where we were either going to have to change a little bit how we were running things, meaning we were aggressively a product team and we needed to move towards being more of a sales team, and we needed to raise money, and like a lot of just market forces were—were on us, and we’d been very close with Bill Ready who had run Braintree and then when Braintree was acquired by PayPal was at PayPal and him and were just talking and he was like, “Well, you know, we’re actually thinking about building something like this.” And I was like—and I’d been complaining about sales. And he’s also like, “Well, you know, also, we have a big sales team.” And so it was this funny thing where, first of all, I never thought that we would sell the company. Like I don’t say that in this kind of silly like, “Oh I’m not here to sell the company,” I was there to sell the company, I wanted to make a lot of money but I didn’t think it would happen because we—when you’re inside of a company it’s hard to see the shine because you only see the patches [right, right], you only see the—the places that are screwed up. It’s hard to see the shine and it was this kind of nice thing of like,”Woah! This actually—there actually is a space for us and a company that is kind of doing similar things, that has an interesting need of this specific thing,” and then this kind of led to an acquisition. And it was—it was—that was a wild thing to do. I—I loved it. Selling the company. I thought it was a lot of fun.

PF Oh really?

RZ Oof! God bless cuz usually it—it starts—it goes to the bankers and the lawyers and it’s like, “Well, what about what about that chair?”

HR So I loved that! That right there.

RZ Did you really?

[24:09]

HR I loved it. It was so much—it was so interesting to see what—like there was this point where we are talking and um there’s a lawyer talking about IP stuff and um they’re really pinnin’ this on this one file. They’re like, “Where’d this come from?!?” After this IP scare.

RZ It’s amazing, isn’t it?

HR And like just diggin’ in and it was just like, “This came from eBay. Like, y’all wrote this. This [laughing] is your file. What’s wrong with you?” [Rich laughs] You know? You know, so it was things like that, I just thought it was fun because it’s a little bit like high school debate, you know? Where you’re—it’s [oh yeah]—but at the same time, there’s so much at stake, the pressure’s really high, and I love that feeling. I love the feeling of like, “If we don’t get this, we gotta go home and I don’t wanna go home.”

RZ Part of the—the—the—this sort of process can be—part of it could be grinding you down [oh yeah] so that they’re continuing to chip away and then you’re just out of exhaustion like, “How do we get this—just, please just end this.” You know my business was sold a few years ago and one of the things I told the president of the company that acquired the business was, “I just need to be able to call you.” [Yeah] Like, “There’s all this nuttiness and I just wanna be able to call you when it just gets so crazy, so you can stop it [yup] and then we can keep going.” And if I didn’t have that, I would’ve just been in rooms with just reams of paper. And that was terrifying.

HR I think that’s actually a really important, important point for anyone who is thinking about selling a company or in the process of: you have to have a champion.

RZ Absolutely!

HR So when things get a little gnarly, you can just be like, “Look, why are we doing this?” And they’ll—they can step in say, “Look, this may not matter.”

RZ Yeah. Yeah.

HR I loved the strife though. I—I have to admit that I love the—

RZ Interesting.

[25:42]

HR Um—it’s one of my favorite memories—

PF You keep going back in!

HR [Laughing] I know! It’s terrible but some my favorite memories on the campaign is when everything was just totally bonkers. Like, during a debate, like we raised the most money during a debate; crazy things happened during the debate like one of co-leaders of the campaign threw a chair once during the debate, you know, and it was cuz he was so frustrated he couldn’t figure it out. And I just love that strife. But I also love it’s like, “Everything is failed. All your database servers are gone.” And I’m just like, “Well,” it’s just like there’s a clarity. Like all the noise disappears, the people who can’t hang, leave. Which is fine, I think there’s just different [Rich laughs] roles. Like two or three of us stand up and we’re like, “Well, I guess we gotta fix this.” It’s just, you know, when you were talking hammers before, I think one of my  hammers is—is when everything is screwed, I can probably help. That’s my hammer.

PF Good hammer! I like that hammer.

RZ It’s like—it’s like you open a first aid kit box and there’s a hammer in it.

PF It’s just Harper!

RZ [Laughs] It’s all the Harpers! [All cross talking and laughing]

PF And you’re like, “I’ve lost—I’ve lost five fingers,” and you pry it open and it’s just Harper like, “Heyyyy!” [Rich laughs] Alright, so you got a hammer. What are you gonna do next?

HR So, I left PayPal. I was at PayPal for a couple of years. And it was really interesting and I really enjoyed—what I liked about PayPal it’s a global company and they do a lot of things internationally and I really think um I think we’re at a big change right now where US dominance is going down and we’re starting to see other players pop up. And some of the other players are just incredibly fascinating. I mean I—there’s so many other places that I got to see through the eyes of PayPal and then—and then separately through the eyes, the independent eyes of myself, you know, Southeast Asia, Indonesia, for instance. Just incredible commerce things happening there and love—I love that. I just love seeing that and so when I left PayPal I think things were more confusing than they were clear. Whereas when I left the campaign it was clear, “We’re gonna start a company. What is it? Nobody knows but we got funding.” Here it’s like, I have no idea. I’m so confused. It’s so—there’s so many things out there that are interesting and I also keep saying to myself that I don’t wanna do commerce because I’ve done it so much. But I don’t know if I can—if I have the choice in the matter, it was just kinda—things seem to just happen.

[27:52]

PF Everybody wants to do something different than the thing that they’re truly good at.

HR [Chuckles] Right, right, right—

PF [Laughing] I mean it’s just you know—

RZ If you have the opportunity to, that’s amazing, right?

PF No, but—but how many musicians wanna do standup? You know?

HR Usain Bolt—isn’t Usain Bolt a football player now? Soccer player [Paul laughs wheezily]. But I don’t know—this is actually a really um what is next is really hard for me right and I think there’s two reasons for it. One: I’m antsy. When I look at my path and when I’ve taken breaks and I’m done—this is my third time I’ve done this, taken a little pause in my career. The first one was a summer; the second one was about 18 months; and this one has been about seven months so far.

RZ That’s a long time! Whaddya—whaddya doing?

HR I actually rolled back a few steps and I’m trying not to do a lot of tech things. Because my whole life is tech, everything I do is tech—

PF Sure.

HR My house is a computer, like everything is tech [yeah]. So when I look at drones I’m just like, “Eh,” but like analogue photography is very interesting and it’s hard and it’s really, really, really hard and I’m not good at it and I love that feeling. Like I—I—I wish there was a word for—you know mouthfeel around words? Or how [mm hmm] something tastes? I wish there was a feeling for the vibe in your head when you’re doing something, like the word for that. Like cuz I could just say, “When I’m doing analogue photography I feel—like this is what’s happening in my head.” It’s like a mix of confusion and excitement and anger [chuckling] when it doesn’t work but also hope that it’s going to work, all at the time and I just lo—love it. There’s also this like this idea that I can fix a few things because technology has changed since the 1970s and so that’s—that was my goal is to fix a few things. And then the other thing that I’m doing is I’m doing a lot of speaking still on the speaking circuit but also if someone says, “Harper, here’s a good conference. You should go. You might meet some good people.” I’ll go. Every time. I really enjoy . . . meeting people and I—I always think about . . . kind of the—the idea that you never know what’s gonna happen. Like if I didn’t—if I just didn’t follow up with my friend Jason’s introduction to Michael Slaby, I would never have done the Obama thing. You know, if I didn’t go, honestly, clubbing in the early 2000s, I never would’ve met the Threadless guys. Like all these things that are very optional and so how do you increase the options? I always think it’s—I’ve been thinking about this, I think it’s really stupid to say but I’ll say it anyway which is like everyone talks about how they have great ideas in the shower but no one’s out there just taking showers all the time. And so it’s like what do you do to create this opportunity to find weird shit to—to find what’s next? And because there hasn’t necessarily been straight continuity between my career segments, it’s a little harder.

RZ Sure!

[30:22]

HR Cuz I don’t know what’s next.

PF You know—

RZ Well also I—I—you’re not gonna take a job.

HR There’s a lot at like—if the team was good. If they were a very, very good team building a product was really like it would be hard to say no. But I probably would.

RZ Ok. That’s—that’s a big deal. Ok.

PF You know—you know Alan Kay at Xerox Parc?

HR Yeah.

PF He used to—he used to joke cuz they asked him this. They had 20,000 dollar Dorado and Alto machines on everybody’s desk. And he was like, “Look: you’re paying me to think, spend a thousand dollars and get me a shower.”

HR Right [chuckles], right, right.

RZ Psshhhhh [chuckling].

PF And they wouldn’t do it, they wouldn’t do it. Like, “We’ll get you a nice—we’ll get you another Alto.” [Rich laughs]

HR I just think it’s really funny because you—you—you—I think about all of these time when I have had inspiration and how do I increase those times? And it’s not—it’s not sitting in an office, for sure. I was talking to a friend the other day, he was talking about his time that was similar to what I’m going through right now and he said, “When I got an office, everything changed.” He said he just got the cheapest office he could find, put a couch in there, a huge whiteboard, a big stereo, and a desk. And—and then it was this idea of like he would go and have a context switch to figuring out what’s next, instead of me sitting in my basement looking at my record collection or my Nintendo Switch or like my solid gold couch or whatever it is.

[31:34]

RZ That—I mean you may wanna try this out. I mean it might expand [laughing] the possibilities of what you’re thinking about here.

HR I’m a little—I’m a little concerned, a little bit. I had a—I had an executive coach that Media Lab gave me a for awhile and—and [chuckles] he was really funny cuz his name is Gunther Weil and he’s really great. It was ah—wonderful experience and um he actually made me think up a mission. Like what is Harper’s mission statement? And he pushed me really to define this which I thought was such an [stammers] I love that [that’s very cool]—I love that. I always love like I think people should have strong brands, I think people like individuals should have like board of advisors—I think all that stuff, so having a mission statement was great but the [chuckles] other thing he kept saying, he’s like, “Have you thought about acid?” I was like—

PF Woah! [Rich laughs]

HR I told my partner, Hiromi, and she was like, “No. No. No.”

PF No, no, no.

HR “No, not an option.”

PF She’s like, “I have enough to deal with. Don’t—don’t do that.” [Rich laughs] Harper. Ok. Many thousands of people are listening to you talk right now. Hopefully, hopefully they’re not just downloading and subscribing but actually listening, and you’ve just increased your optionality in the universe quite a bit, what do you wanna hear from? How do they get in touch? How do they reach you? What should happen now?

HR Well it’s very easy to reach me. Um my email address is on my website, harperreed.com, or just hit me up via Twitter. Looking for, you know, I don’t necessarily think advice is helpful but if someone wants to hear kind of my story from the frame of reference of their problem then um, you know, I would love to chat about startups or about commerce or selling your company or what-have-you. But, also, if you’re in Chicago, we should just hangout. Or really anywhere. I’d also love to hear good pranks. My brother and I need a new prank. I can tell you some of our—our—our drafts, if you want, but, yeah, we need a new prank.

PF Alright, that is a perfect invitation to the world.

RZ Yeah, they’re comin’.

HR And one thing to keep in mind is that billboards are pretty cheap in smaller towns.

PF Thank you [Rich laughs]. Harper Reed, thank you for coming on [music fades in] Track Changes.

RZ This was great.

HR Oh good. I hope it was helpful.

PF Hey Rich?

RZ I hate talking to people who are more interesting than me.

PF Guy’s got a lot goin’ on but nonetheless! We do a lot too. We get a lot done.

RZ What do we do, Paul?

PF We build platforms, we build [Rich laughing] apps on top of them. You know, if you were—if you wanted to build something like the five or six hundred thousand things that Harper’s built in his career [Rich laughs], you might come to a company like Postlight and we’ll help you get it done. Uh anyway, it’s—it’s good to talk to an old friend, and if you need to talk to us, um you can tell us about your pranks too. [email protected]

RZ Have a great week.

PF Bye [music ramps up, plays alone for five seconds, fades out to end].