Episode 27: Harper Reed
“They told me they cleared my schedule for a visit from a VIP. This literally never happened. It had to be important, but who could it be? And then I see them bringing this person into the office…”
From the Episode
Hugs with the Prez
About Harper
Harper Reed is a technologist that predicts the future for a living.
How does one predict the future? Well, a good track record certainly doesn’t hurt the odds. And neither does looking like an oracle. And frankly, the variety of his experiences does give him one hell of a boost.
Harper was born in Greeley, CO, a Denver suburb known for its arts scene, its churches, and abundance of craft beer. His childhood home didn’t have a TV, but it did have an Apple IIC (two-c), and that little 1 MHz CPU with 128 KB of RAM would be the beginning of his love affair with technology.
After tech stints in the publishing and creative industries, Harper became the CTO at clothing company Threadless, where he pioneered crowdsourcing and grew the company from a 12 person startup to a multi-million dollar enterprise.
In 2011, Harper joined President Obama’s reelection campaign as CTO and assembled a team of engineers from the likes of Google and Twitter to build Project Narwhal, which powered everything from the network of campaign supporters to Obama’s poll watching software.
Having successfully leveraged APIs to defeat the GOP, Harper founded mobile startup Modest, which was acquired by PayPal, where he spent a few years as an Entrepreneur-in-Residence, guiding teams into the thrilling future of e-commerce.
And now, Harper is the CEO of General Galactic Corporation, a web3 company building software for the new internet.
He also sits on the advisory boards for IIT Computer Science and the Royal United Service Institute, and is a Director’s Fellow at the MIT Media Lab.
Somehow, Harper has also found a way to hack the space-time continuum. At least, that’s the only explanation for his ability to find the time to create four patents and become proficient enough at juggling to open for Sir-Mix-a-Lot.
When he is not juggling, creating patents, working on the future of web3, or traveling the world, you can find Harper hacking on personal projects and enjoying life in Chicago with his partner, Hiromi and their beautiful and bizarre poodle, Lulu.
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Max:
All right. This is Moral of the Story. Interesting people telling their favorite short stories and then breaking them down to understand what makes them so good. I'm your host, Max. Today's guest is Harper Reed, a technologist that predicts the future for a living. How does one predict the future, you might ask? Well, A good track record certainly doesn't hurt the odds, and neither does looking like an oracle. And frankly, the variety of his experiences does give him one hell of a boost. Harper was born in Greeley, Colorado, a Denver suburb known for its art scene, its churches, and abundance of craft beer. His childhood home didn't have a TV, but it did have an Apple IIc. And that little 1MHz CPU with 128KB of RAM would be the beginning of his love affair with technology. After tech stints in the publishing and creative industries, Harper became the CTO at clothing company Threadless, where he pioneered crowdsourcing and grew the company from a 12 person startup to a multimillion dollar enterprise. In 2011, Harper accepted his hire calling, joining President Obama's re-election campaign as CTO and assembling a team of engineers from the likes of Google and Twitter to build Project Narwhal, which powered everything from the network of campaign supporters to Obama's poll watching software. leverage APIs to defeat the GOP, Harper founded mobile startup Modest, which was acquired by PayPal, where he spent a few years as an entrepreneur in residence, guiding teams into the thrilling future of e-commerce. And now, Harper is the CEO of General Galactic Corporation, a web 3 company building software for the new internet. He also sits on the advisory boards for IIT computer science and the Royal United Service Institute and is a director's fellow at the MIT Media Lab. Somehow, Harper has also found a way to hack the space-time continuum. At least, that's the only explanation for his ability to find the time to create four patents and become proficient enough at juggling to open for Sir Mix-A-Lot. When he is not juggling, creating patents, working on the future of Web3, or traveling the world, you can find Harper hacking on personal projects and enjoying life in Chicago with his partner, Hiromi, and their beautiful and bizarre poodle, Lulu. Harper, welcome to the show.
Harper:
That's all true.
Max:
All true, which makes it that much more amazing. So you're here to tell us a story. Do you wanna set the stage and talk about anything we need to know before we get into the story itself?
Harper:
Yeah, I think the stages, it's 2011, maybe 2012. I am the CTO for the Obama campaign. I am dealing with a lot of imposter syndrome, dealing with a lot of fear. I wouldn't say a lack of confidence because I mean, I think that's just part of those two things, but it's mostly I was very afraid of making a mistake. The Job was a very big job. I had never done anything as important as this. I'd never done anything that I felt more connection to, like just a raw connection. I mean, I made t-shirts, which was really fun, and I really enjoyed it. That was my previous job for this, but I'd never done something that if I messed up, I would end up in the New York Times, right? Like there was
Max:
Right.
Harper:
a lot of pressure there where it was a very different experience. So the setting is... a lot of kind of existential dread, but also complete excitement and hope and want to be successful with a wonderful team, working with just all of these incredible people. I often compare it that, you know, like a gazelle is born to run. These people are like that, where they are doing this one thing that they are so good. It's like working with a pro athlete.
Max:
Yeah.
Harper:
Like I sometimes felt like I was the high school quarterback amongst a bunch of NFL people. where I
Max:
Yeah.
Harper:
was just sitting there and I was like, I know the game, I'm pretty sure I've done this before, but the way y'all are doing this is way different. So that's kind of the setting of this kind of, I felt out of place and we were good, but I still felt like I was the amateur. And so I was struggling, but I needed, that was it. That was the setting. I mean, I felt that way the whole time, but that right at that point, I remember this very specifically.
Max:
Stakes make for a good story. Let's do this.
Harper:
I think so, I think so. So as I mentioned, this is 2011, 2012. I don't actually remember the day, but working at the Obama campaign, you had so much just weird stuff happen. Like you'd get an email that would say, Harper, a very important VIP, which is a funny, a very important VIP. Like that's like two VIs, right? It's VI,
Max:
Little redundant.
Harper:
VIP is going to be in the office on Tuesday or Wednesday or whatever. Can you spend 15 minutes talking to them about the tech and the platform and all the stuff you're doing? And this also is built on this huge amount of media training that I had had where I was a tech person. I mean, I really was a pure tech person. I still am today. I program all the time. They would say, OK, well, you have to talk about the technology, but you can't mention technology. You can only talk about Barack Obama or the work that you like, the great work that he is doing. And so it's like this thing of like, what kind of database software would you use? And I'd say, well, you know. Barack Obama has this very amazing idea of around grassroots organizing. And so we just looked at that and used software that matched his perspective on how that, you know, whatever, whatever. So like,
Max:
Yeah.
Harper:
so keep in mind that like, it's a lot of bullshit. Like there's just a lot of stuff where you're just like making things up, trying to get this though. And everyone knows the game. So the VI VIPs, they would say Harper, this person, this surrogate is coming in and it could be anyone like John Cusack, it could be, you know, anyone. Anyone, Aaron Carter, like anyone. You never know who it is, who's gonna show up. It could be like the NBA star, the actor. It could be Barack Obama. Like it could be literally be anyone. And they don't really tell you who it is going to be. I remember one time they were like, Harper, some very important people are coming tomorrow. Just be aware. They're gonna just stop by everyone's office and say hi. Just tell them a little bit what's going on. And it was like Anna Wintour and a bunch of models. Like, it's just like weird. Like you just never know who
Max:
It's
Harper:
it is
Max:
crazy.
Harper:
going to be. And so this one day I get this email and it's like maybe a Sunday. I get the email and you got, I mean, it's 24 hours, seven days a week kind of job. So I get this email on Sunday and they're like, Harper, we've cleared your calendar for Monday afternoon, which is not something that anyone did. Um, because every work was important. So if they cleared the calendar, you're like, Oh boy, what's happening? We have a VI VIP coming in and we just want you to spend some time with them. And I was like, great. Um, and so I'm sitting there and we're kind of waiting. with beta breadth trying to figure out who is this person, who is this, it literally could be anyone, Bill Clinton, you never know who it's gonna be. And so you're thinking like, who is a person that is important enough, and important means like either politically important or funding important, but important enough where they're going to clear your calendar. And so we're really just like me and Michael Slaby, who is my boss, we're just like, just struggling to figure out what was going on. And it was, they cleared my calendar, like Michael was along, Slaby was along for the ride, but like, they're very specific, he wants to see you Harper. Okay, this is weird. So I'm sitting there, what is, who could this be? And then across the way, and keep in mind, we're in this giant open floor planned office, I mean, gigantic, a thousand people on one floor boiler room, like just giant, not a place for productivity, but we made it happen. Like you read any book about how to design an office. It's the opposite
Max:
Yeah.
Harper:
of what we had. Um, and it was just this, so across the way, I'm at like the far corner from the entrance, I see. Um, one of the admins, these, these assistants that we had, who were just like some of the most talented, incredible people I see them. bringing this person, like trailing this person who's kind of jogging and really coming over very quickly, trailing a couple looking like business people. And I'm just like, what is happening? And so I just know. You know when you have that feeling? You just know, you're like, that's who's coming to see me. And it gets
Max:
Yeah.
Harper:
closer, I recognize it, it's this guy named John Maeda. John Maeda was the president of RISD at the time. And his path at RISD was really interesting. RISD did not like him. And so he did a lot of stuff to figure out how to make RISD, the faculty and the students like him. And I'd done a little bit of work with John when I was at Threadless. And so we casually knew each other, but not actually. We didn't like, there wasn't like a lot of, like if I would say hi to him, he would probably say hi to me, but we didn't have a lot of camaraderie. And just, we just didn't know each other personally. And so he kind of jogs into the office. And for anyone who knows John Mayday, he's pretty frenetic. Like he is hopped up, he's ready to rock. And so I'm just like, okay, cool. They're like, well, this is Harper. You know, you guys wanted to chat. And I'm like, okay, this is the guest. Like, first of all, it's weird because I like John a lot, but I didn't think he was a VI, VI, VIP that would clear
Max:
Yeah.
Harper:
the schedule. So I'm just
Max:
Yeah.
Harper:
like, okay, what's going on? And he sits down and he just gets right into it, which those of you who've interacted with John know that this is how it goes. He just gets right into it. So we sit down and he's like, this is my consultant who works with me to help figure out the politics of RISD. And Harper, I'm guessing you are dealing with a lot of lower P politics. That in the big P politics, there's a lot of lower P politics. And I was like, yeah, that's true. There's just a lot of politics. Anytime you're so close to power, anytime you're so close to truth, all these things, there's a lot of politics. People are just trying to do the best job that they know how to do, a little bit by any means necessary. And sometimes that means stabbing some people in the back. It's a complicated space. And John is just like, yeah, I bet you're dealing with a lot of politics. And I was like, man, it's so true. He's like, I'm dealing with a lot of politics. And he's like, I want to show you how I deal with the politics. And so he goes through and he shows me these, gets out a deck of cards first. He basically just shows me these different visualizations of the politics at RISD. He's like, I have this deck of cards. He writes names on everyone. Here's it so I can rearrange them to figure out what are the different cohorts, different power structures, all this stuff. And I'm like, okay, cool. Like I can picture myself doing this. And he's like, it doesn't work. I'm like, okay, I won't do that. And then he goes, and this is like this protracted presentation. Like he's doing a presentation. It's like a sales presentation for me about this. I don't know what's going on. I'm like, they canceled my meetings. We have a very, very important person, which is this person that I kind of know. And like, I just, what is he talking about? And then he goes on and he's like, well, he talks about how he was at media lab and he did all this amazing computer vision or visualization stuff. And so he shows me that how he visualized his visualizes his political relationships. And he starts, here's how I measure it. All this stuff. He shows this amazing visualization on his laptop and he's like, this doesn't work. And I'm just like, what is happening? And finally he says, the only thing that works is for you to look at your inbox and look at your outbox. And if you want to solve politics, little P politics in your organization, you have to ignore the inbox and only pay attention to your outbox. because you're in a position where you are doing service for others, you're building things for others, you're building things for stakeholders, you're building things for customers. And oftentimes, those of us who are in positions like this, we only pay attention to our inbox, and that's a mistake. You have to pay attention to your outbox. And he's like, you have to manage by your outbox. And he talks about how he had a similar situation where people didn't trust him. And he's sitting in this world where no one is trusting him, no one is looking at what he's doing as positive. And he's trying to figure out why. And then he realized that he just wasn't emailing anyone out. He was waiting for the email to come in. And so the emails that are coming in were complaints. Emails going out were status updates or what have you. But he just was waiting for this to happen. And so all of these people felt like they didn't have or he wasn't bought into their program, that he wasn't helping them. And in this world of like leadership, I think there's a lot of us who sit here with these giant egos waiting for people to talk to us.
Max:
Mm-hmm.
Harper:
And if that's good or bad, I don't have a judgment on that. You know, I've been in both sides of this. But I do think that if you're trying to defeat or get further in that world, you have to be the one that emails out. And so he talks about how he learned from Larry Bacow, who I think was the president of Harvard, about this, where Larry Bacow said, managed by your outbox. Like if you're trying to maintain positive interaction, you have to manage by your outbox. So he tells me this, and then he basically gets up and he leaves, he runs off. This is probably 45 minutes. The whole afternoon was canceled. Like 40, just leaves, jogs off. And me and Slavy are just like, what the fuck? What was that? How did that, how does that even, what is going on? So I had like a couple of days to think about this and I was in this particularly rough period where we were trying to ship this big product and a few of the stakeholders were really frustrated and they were really, really frustrated. And during this time, there were a bunch of people who said, you know, who thought I should be fired. And it was a really stressful, stressful time. And I thought to myself, you know, what could go wrong? Let me try this wild trip that John made is kind of put me down. So I started sending these emails and the emails would be super simple. It'd just be like, Hey, you know, so and so, you know, here's a quick status update on what's going on. Um, just thought you'd like to know. That was it. Like very simple, just a touch point. I get this reply back. That was like, thanks. Also, Hey, thank you for the email. That really meant a lot. And I realized when I got that first email that I had messed up this entire time. that the fact that they thanked me twice, once for the information, but also for the email, shows that that really mattered to them. There was a before and after to this advice. Before, things were really stressful, things were really hard. After, things were still stressful and hard, but I felt like we had more buy-in from the stakeholders on what we were doing. We had more people who were with us instead of against us. We had more people who were willing to go to bat for us. And this really... changed how I thought about communication in general, whether it's communication with my investors, whether it's communication with my employees, customers. I look at this, every single thing I do, I often am thinking, okay, how do I, if I take a peek at my outbox, what does it look like? Okay, my investors are frustrated. Well, let's take a peek at the outbox. Have I kept them up to date? Customers, you know, these customers frustrated. Have I, did I tell them about the change that was gonna happen or did we surprise them? Surprise is never good. And I have this theory. I was talking to a friend and I was saying, what's the thing that aligns all of your companies that are successful, the big investor? He was like, well, I don't think there's a thing that causes them to be successful, that's one thing, but I can tell you that all the companies that are successful send investor updates.
Max:
I'm going to go ahead and close the video.
Harper:
And this goes into this idea of just managing by your outbox of even if you're failing, And every Friday you send a note that says, hey, we're losing money, we're losing money, we're losing money, we're losing money. And eventually you get to zero, there's no surprise. But if you don't send an email and then you send one final email that's, hey, we're at zero, everyone's gonna be frustrated because they're not gonna know what the hell's going on. And so it's this idea of just really, it just really changed everything about how I communicate. And sometimes I'm good at it, sometimes I'm bad at it. But I always have that metric, that place to measure. It's like, how am I doing? How am I doing as a CEO? Look at the outbox. How am I doing as someone who's raising money? Look at the outbox. How am I doing preparing to go to a business trip to wherever? Look at the outbox. Like that's the measure, that's how you manage. And that really changed like everything. And I'm really thankful that whatever admin cleared my calendar because I thought this was really important that I don't know if they knew that this was gonna happen but this is truly one of the most important pieces of advice I've ever received.
Max:
Do you really think that they did not know what he was coming in for, or do you feel like they set that up because they kind of saw what you might have been struggling with?
Harper:
Um, I don't think they knew, um, mostly because everyone was kind of running by the seat of their pants, everything, everyone's hair was on fire that there wasn't a lot of like, meta, meta, meta, like, as we would say, this is not a place for career development.
Max:
Yeah,
Harper:
The
Max:
yeah.
Harper:
career development is you no longer work here, you probably should get another job where they'll develop your career. Like that's the career development. So there wasn't a strong, that wasn't there. With that said, you know, I think this goes to a little bit of just the insight that people like John May to have where he was able to just see this from, you know, a million feet away. He was not involved. He was able to see this and probably, you know, maybe he had a conversation with someone and they said, oh, you should come and talk to Harper. Like I could imagine that. But I don't think it was this like super deliberate thing of like, hey, this would happen. I just think he has this specific insight. And I've had a few people like this in my life where just he's just able to tell his own story and kind of be like, yeah, well, if this is important to you, great. But if not, I'm gonna go. You know, and there's like the zooms off. Um,
Max:
You're like, what just happened?
Harper:
it was, that was the funniest part about this whole thing is it's one of these things that during it, I was like, this is all very interesting, but like, I got to go, like I got stuff to do. Like I'm, I'm happy you're here. And he might've been a big donor. I don't know. He, you know, he, he might've been, um, he's obviously an important name and important person and has a lot of influence. So like he is a VIP in that regard by most of the majors, the campaign find important, but. You know, we were both sitting there like, this could literally be Bruce Springsteen. We don't know. You know, and then John Maeda from RISD just shows up who we both know. And we're like, okay,
Max:
I mean,
Harper:
cool.
Max:
the crazy thing about that is I feel like there are times in your life when somebody will enter your life and they will say something that you might not be ready for at that moment. And it is a sign of real maturity that you are willing to sit on that information until you are ready to process it without writing it off, which is exactly what you did.
Harper:
Yeah, I also think that you're like we were in a war zone and like you would use literally anything like the person he could have said like what I what worked for me is I ate a bunch of hot dogs and I would have been like, fuck it. Let's go see if that helps. You know, because
Max:
Try to
Harper:
because
Max:
eat hot
Harper:
we were
Max:
dogs.
Harper:
willing to try everything. And what was really interesting about this was that kind of horror movie view where they zoom in and pull the camera out or pull the camera. You know, I'm talking about where
Max:
Yeah.
Harper:
it has that weird parallax kind of thing
Max:
Yes.
Harper:
where it's like and it's like, oh, no, like that's That's how I felt after I received this email from my friend who was like, thanks for the email. That's how I felt reviewing all of my previous communications. You know,
Max:
Yep.
Harper:
where I was like
Max:
Yep.
Harper:
waiting for the feedback and it's like, why didn't I just email and be like, yo, what do you think? Like that would have solved the whole controversy. Like so much time was wasted because whether it was ego or lack of time or just lack of focus, I just didn't do what I needed to do there. And this was a very... It was such a good lesson.
Max:
You know, it immediately made me think of a time when I was just getting started in commercial real estate and I was working for this guy named Craig Castle, who will be the first to tell you that he's not the smartest guy in the room, but he's the one that works the hardest.
Harper:
Mm-hmm.
Max:
And more importantly, I think he has an incredibly high EQ. And... We were working in the suburbs at the time and doing leases in the suburbs and he got a big project with Sony to sublease their space in, uh, I want to say it was Itasca and he couldn't do it. Like it was just hard. And every time I would talk to him, I'd be like, how's the Sony sublease going? And he'd be like, terrible. Nobody wants to see the space. They're asking too much money. They're inflexible. And I go, aren't they worried about that? Like, aren't they telling you that? need to step up or they're gonna find somebody else because so many people are calling them he goes here's the thing I email them every single week and I tell them what we've done and I give them a status update and I think they
Harper:
Yeah.
Max:
can see that I'm working my ass off and that's why we're still here and I was like that is such simple and underrated advice like
Harper:
Yeah.
Max:
people don't want to be surprised he just want to know what's going on they want you to be proactive about it and you just, different people learn that at different parts of their lives, you know?
Harper:
Yeah, it's hard. And some people do this and they over communicate and it becomes annoying.
Max:
Mm-hmm.
Harper:
And some people do this and they under communicate and it becomes annoying. And some people communicate perfectly and it becomes annoying. Like it's very hard to feel. It's a little bit, I think like cooking. Like anyone can cook in the same way that anyone can communicate, but only certain people are really good chefs. And you don't become a good chef. You're not born with that. You become that way by practicing and listening. And every time I join a new organization, which... strangely more often than I imagined as a young person. It takes me a while to figure out how that communication structure works. And in the case of emailing Sony, I'm sure they really appreciated those weekly status updates because they're wondering where their money's going, where their time is,
Max:
Mm-hmm.
Harper:
why are you wasting this time? And if they see all the work, that's very clear. But you don't want it, like an investor doesn't give a fuck about your weekly progress, right? They
Max:
Yeah,
Harper:
don't wanna know that. So
Max:
it's
Harper:
it's
Max:
true.
Harper:
like this funny problem of reading the room. But it really is, I think, about managing. In the same way that managing an employee is different from employee to employee to team to team, it really is about management and focusing on that, how do you manage by the outbox? How do you manage by your own sending? And it could be blog posts, I don't think so, but I think it's emails. This is why I'll never, never not believe in email. Like everyone's like, this is an email killer, and I'm like, yeah, right. Like I don't believe it. I don't believe it. I mean, I'm in the I'm in hella chat groups and you know, all that stuff group
Max:
Yeah.
Harper:
group texts, groups, all that shit. And it's like, they're all great. But when I need to connect with someone about something or I have a problem with an employee or they have a problem with me, like emails, the way that we document it for many reasons. But that's really interesting. It makes me think a lot. And I don't think I'm complete. You know, that's the other thing about this advice is it's not definitive.
Max:
Mm-hmm.
Harper:
It's not like, oh, if you paint everything red, everything's great. You know, it's just like
Max:
Yeah.
Harper:
It's like, here it is. It works differently for everyone. Keep trying, keep iterating, keep asking for feedback. See if it works.
Max:
Well, I mean, it's the chef analogy is fantastic. It's a really great way of looking at it. I think it's an evolution, right? I mean, what I think it was Ray Dalio that said, whenever you solve a problem, you just unlock the next level. Right? So you have been given the tools to solve this problem of why am I struggling? Why are people dissatisfied? And that has allowed you to unlock the next level, which is, okay, I have this skill now and now I can, now I have, now that's just another skill that I have in my toolbox, right? Another tool that I have in the toolbox. What is the moral of that story?
Harper:
I think there's a couple of morals. I think the main one is like the brick to the face moral of like managed by your outbox. That's the main one. But there's a couple of subtle ones that I think about a lot, especially when I'm telling it, which is don't underestimate people's advice. Like you might get this wacky person that's gonna come in. It could be anyone and like, you could be like, fuck, I really wish I have work to do. Why am I spending my time here? Like I could have told them, no, I can't meet with this person. There's so many actions I could have done. that would have stopped that from happening. And it's just kind of like just being open to what happens to whatever's gonna happen. Like just letting yourself, I always think of it as letting things happen to you, obviously within safety. But people once, recently I was talking to some entrepreneurs and they asked me how I think of new things to start a company around. And I'm like, I never do. I just sit there and wait for it to happen. Like, I don't know, like I don't have a process. I know some people do some friends of mine have like processes they go through and they do some very lean startup things or whatever. I literally just kind of sit in an office. Like we have a live office studio space near my house and I just kind of sit there and build weird shit and just try and just honestly just play around and stuff happens. And I feel like that is a similar idea of just like, how do you just let something happen? So rather than me saying no to the admin or the assistant who's like, Hey, we have this VIP coming in. We want to spend time with you. Um, I could have said, no, I can't do that. I have time. I need to focus on this other stuff. I was just like, okay. I don't think that's really the best idea, but you obviously think it's good enough to send me a note about it. Let's see what happens. You can't get time back, so be careful. But at the same time, this literally changed my life. I'm happy I did it. So there's that part. I think another moral is just, you never know where advice is coming from. And it could be in line at Chipotle talking to the person that's dishing out your beef or whatever. Or it could be some fancy person who's the president of RISD or is now head of AI design at Microsoft. Or it could be just a friend that's like, hey, I was thinking about this.
Max:
There's a distinction though, there's a very important distinction to make if we go back to why you start companies, not by using the lean startup methodology per se or having this very dogmatic process you follow. The key distinction is you have to be a you have to have the skill of recognizing an opportunity and being able to evaluate it because if you don't have that then being open to something and not recognizing it when it smacks you in the face is the same thing as not being open to it at all right like
Harper:
Mm-hmm.
Max:
understanding that you want the feedback, but not being able to recognize it when it's being offered to you is The same thing as not being open to it And so I think it's interesting you described as a brick to the face because they were like
Harper:
Yeah.
Max:
We're not gonna take the chance of you not recognizing this we're clearing your calendar. This is a VI VI VIP
Harper:
Yeah,
Max:
right
Harper:
yeah. And it happened often, but it was never advice-based. Like this was the only time that it was advice-based where most of the time it was a song and dance where I would get
Max:
Yeah,
Harper:
up there and
Max:
yeah.
Harper:
be like, look at my dance. Here's my tap shoes or whatever. But one of the things that influenced this for me was hearing Brad Feld talk about his meeting with David Cohen when they started Techstars of, you know, David Cohen, someone who kind of was a nobody to some extent, or at least to Brad Feld who... kind of convinced his way into a meeting with Brad Feld and pitched him on this idea of Techstars. And now Techstars started, which is obviously
Max:
Yeah.
Harper:
a huge deal and has generated just gobs and gobs of unicorn companies, wealth creation, et cetera. And it was just, Brad Feld took a chance on some unknown guy to listen. And in that frame, his perspective is about... entrepreneurship and whatnot. But it doesn't matter what you are, like taking a chance and listening, I think is the key. And listening with an open mind and not listening just to say no. Because
Max:
Exactly.
Harper:
sometimes I find myself that way. I used to joke that I was a CT no, instead of a CTO, because it was so easy to say no.
Max:
Yeah.
Harper:
But you have to say yes sometimes.
Max:
Totally, and if you're gonna use your time, then you might as well listen like it matters, right? What do you think makes that story so good? In other words, what makes it work from a structural storytelling perspective?
Harper:
Hmm. I think I don't believe in stories without a narrative arc. So I think you have to have a narrative arc. You have to have a conclusion. Um. D. there's some mystery, because you're like, what is happening? Like both,
Max:
Yup.
Harper:
you know, and I think it's also coupled with like a... If a junior engineer was telling the story, no one would care. And so there's this reality of when you're telling a story from authority, like it doesn't matter who you are and it just matters who your audience is. Like I have the privilege and luck and luxury to have done that job. And we have the, you know, I'm very thankful that the voters voted to elect Barack Obama or the story would be very different, right? And so there's a lot of luck that goes into this being a good story. Because I have a lot of stories of advice that I probably incorporated into my life from when I was an engineer, just an individual contributor. And those stories, you know, I typically don't go on a podcast telling those stories because they're not, they might be as impactful, but they're not, it's not the same story. And so I think it matters less on what kind of accolades you have or how senior you are or how much success, it just matters that your story has a little bit of a... of authority. Like I'm telling this story because it's like, yeah, it changed my life. I started communicating differently. And then it's like subsequent success. I can show was led to that. You know, like the fact how we sold our last company helped, you know, managing by my inbox helped with that and so on and so forth. And so you can kind of say like, here's this narrative arc, there's a little bit of mystery. There's this this kind of problem that I have.
Max:
Mm-mm.
Harper:
But it's also not like the moth story slam where I'm like, I was sitting in my office and I was trying to figure out how to communicate. And then, well, let me go back to the beginning. My name is, you know, it's like not that kind of
Max:
Yeah.
Harper:
so formulaic. It's just a little bit of just like this. Here's what's happening. It's wild and crazy. There's a simple setting. Um, there's a problem to be solved. And then there's some mystery.
Max:
I also like how you used visual elements in the story to help the listener really imagine what it looked like through your eyes at that moment. That's really powerful.
Harper:
It's a very, um... I actually think it's interesting right now to think about this stuff, because with all of these large language models around AI, all this stuff, we're starting to think a little bit more about descriptive language. And there's this theory that I have that all of these folks who spent their time reading or writing or studying at schools that focused on reading and writing and not engineering or what have you, liberal arts college grads. people who are really good at hip-hop, like all these people who are just their whole vibe is about describing things visually or describing things cross-modal. So like I'm using my audio to describe something visual or I'm using text to describe something audio, you know, like you can do these
Max:
Yep.
Harper:
things. I think those people are going to have a lot of success and I really value that my ability to do that in some regards because, you know, telling stories is fun. That's really fun. But if you can get people bought into the atmosphere.
Max:
Yeah.
Harper:
That's the key. You know, and the atmosphere in these places are, you can talk about the smell. Like
Max:
Yeah.
Harper:
I'm sure the tech, like they used to call us Occupy Campaign because we were all a bunch of gnarly, smelly dudes. And it's like this whole thing of like, building out that visualization and such shortcut language that allows people to be there. And I really admire some of those best storytellers as much as I made fun of Moth. They do such a good job of that. of like really leaning in and bringing people along and giving them the hook. And they have that pattern. The reason the pattern is there is because it's a really great pattern.
Max:
Yeah. And you get engagement that way because people are like leaning forward in their seat.
Harper:
Mm-hmm.
Max:
So you talked about storytelling in general. How do you use storytelling in your life, whether it's personal or professional or whatever the case is?
Harper:
I only tell stories. I don't actually do anything. That's all I do with my whole life. That's how I fundraise or have fundraised thus far. I think it'll change as our company progresses, but I don't think it'll change that much. I really do believe that the best way to be successful is to be very good at telling a story that people can buy into. Because, and I'm sure you see that in real estate, where if you're able to get them to buy into a narrative that includes them in the space or in their success within this thing, then the deal is over. It doesn't matter if you're raising money. It doesn't matter if you're selling a house or an office. It really doesn't matter. It's like, I can remember once, good friend of mine, Dan Line, I don't know if you know Dan,
Max:
Yeah,
Harper:
at
Max:
it's CB.
Harper:
CBRE. Yeah, he hooked me up with this, my last company, with this office space. Hit at this building downtown, huge skyscraper type building, like the whole thing. We had a half a floor and it was so cheap. And he was like, you gotta get the owner of the building to buy into your story. And so we sat there, I sat with the owner and I told him the story. And it was like, it was like that thing where I needed like a shot of charisma before I went in. And then I had to put on my charisma clothes and I had to like amp myself up. It was like a peacock. I'm like a peacock walking into the Starbucks downtown trying to like, you know, get myself that one
Max:
Yeah.
Harper:
right on, on Randolph or Ride by Randolph or whatever. And I'm sitting there and it's like, it's... This is interesting for me because I think about this a lot. It was, we had the story, I told him the story, all this great stuff, it was wonderful. But then I found out that the person was gonna go to Turkey and I was like, oh, I have some friends in Istanbul, I'll hook you up with them. And it's like, that was actually the clencher. The narrative helped, but the clencher was just offering this thing that he needed, this simple, simple thing. And it was this funny thing of just like, you can't just rely on just the story.
Max:
Mm-hmm.
Harper:
If I just offered the hookup to Istanbul, we never would have got to the hookup to Istanbul if I wouldn't have been telling the story. And I really truly believe my advice to startups everywhere, whenever I see a pitch, it doesn't matter how good the pitch is, it's always like, make sure you land the narrative arc. Like you have to land it. It's like a ski jump. You shoot off, it shoots straight in the air, you're flying through the air, there's an apex, natural apex, and then you're going down. And if you go down and everyone on the call is like, great, cool, thanks, like you're fucked, you're done. But
Max:
Totally.
Harper:
if it's like, if you're going down and it's like, they're great, cool, thanks, you can still pull it off. You can still pull off. You could be like, oh, I'm gonna be in San Francisco next week, let's meet up for coffee. You know what I'm saying? Like you could do
Max:
Yes!
Harper:
whatever, like you could pull anything out there. So it's really a funny thing of, I think about narrative arcs, like the arc part so often. And I think it's so important. And when I, for instance, we're probably gonna be fundraising shortly for my company. And I was telling my co-founders the other day, I was like, I think I got the arc. I think I got it. And metrics are there, of course. Metrics are important, but I think metrics are less important than the narrative. People want to believe in dreams. They don't necessarily care about numbers. Now numbers are what you care about when things are going bad.
Max:
Mm-hmm.
Harper:
So you have to have the numbers so you have those people there when it's good and bad. But when it's going great and everything's gangbusters. You know, it's, I mean, look at the stories about early Facebook. It's all about this narrative about Mark Zuckerberg. You know, look at the stories around OpenAI right now. It's all about Sam Altman.
Max:
Mm-hmm.
Harper:
Like Sam is new to OpenAI. Like it's funny that that's the narrative. The narrative is about these boy wonders, all these things. And you can fall into that, you know, and you have to also be careful what the narrative means. Like what is the bad part of the narrative? And this is why I do think people should invest in media training if they can,
Max:
Totally.
Harper:
because you wanna be able to pull out of that narrative. I think it's a little too gnarly.
Max:
Well, you know, I think when storytelling is used as a means to an end, as a tool to create connection, that's when you're at the next level of it. because you created a connection with the landlord that set him up to be receptive to your offer to hook him up with people in Istanbul. When
Harper:
Mm
Max:
you
Harper:
hmm. Mm hmm.
Max:
are talking to investors about fundraising, you tell them a story, the intent of which is to create a connection with them. Right. So I think once you get to that point, that's when it really sort of levels up the game. So with that in mind, what advice would you give to, uh, to those that want to learn the craft of storytelling, besides media training.
Harper:
I think you need to be really comfortable with your own story. I think that's the first thing. And, um, I've been very lucky to have a broad, broad story. Um, what I started to do is I found that there were a few things that were in my world that I was just forgetting about everything. My main problem is I have recency bias, really bad recency bias problems. So if someone were to say like, Harper, here's an avocado. All I can think about for the next day and a half is avocados, it's terrible. Luckily, I surround myself with things that trigger things that help my company. But I was just forgetting all these things. And so I was finding that I needed to figure out how to tell the Harper story that was a broad, I think a lot about literature. You don't want the very thin character.
Max:
Mm-hmm.
Harper:
You want that character that has a lot, that's a robust character that has a lot of life in it. And I believe every person. has a magical thing to tell the world. I don't believe every person needs to tell the story. Like those are two different things. People have something they can tell if they want to. And so the first thing is like, figure out if you want to. You don't have to. You can certainly find people who are good at storytelling and just hang out with them. Like you don't have to be the storyteller. But if you do wanna be the storyteller, just start quantifying it. Just start writing down all the things that are important. If you go to my website, harper.lol. If you go to that website, there is a multi-page timeline of where every time I remember something I've done that I think is fun, I'll put it in there. And it stopped at 2021 for some reason. I was just thinking, I should add more stuff there. Because it's not like I stopped doing stuff. But that, what that did for me was start quantifying a little bit of those stories and putting them together into that thing to try and make. And this is to remind myself more so than it is to remind others. I think it's a funny way to show a bio. It really is about just like trying it out. I hung out with a lot of comedians and performers when I was younger and I went to a comedy writing class and they were talking about all these functions that they have and one of them is like the callback. And there's all these like comedic things that they do to like make sure their stories are really good. And it's like, I think that's a great investment but you can just
Max:
Mm-hmm.
Harper:
practice. That was the other thing. They just practice dumb ass stories all day long on one another. and just like see how it lands. And if it works, it's great. I tell the dumbest stories all day long to my partner. She's just like, this year, you're an idiot. I tell them to my friends, I try out jokes. Like I will try out, I will literally try out jokes. But there's other things. Here's an example of one of the story parts that we told when we were raising money. We were raising money for this JavaScript SDK for video. So we put widgets on our screen. One of the widgets that I built was a heart rate monitor. So you could see my heart rate during the pitch. It was right on my screen. And so we would do this video, these pitches, and this was early 2021. So no one was leaving their house really. And we were doing these pitches and my heart rate monitor was there. And one of the reasons I wanted that there is because I wanted to show a that our product was very versatile. But I also wanted the people who were talking to the know that they had a physiological react like impact to my life.
Max:
Oh, cool.
Harper:
And I wanted this and I would talk about this as a thing. And there's a little bit of a story there, but that's not the main story, but there's a little bit of a story there, this little narrative there of like, hey, like don't be a dick. Like there's a power imbalance between me and you. And I want you to know that if you fuck with me, like my heart will raise and that will hurt me. And that's not what I want from partners, et cetera. And so like, I want you to be able to acknowledge this with a very visual thing. That was fun because
Max:
That's
Harper:
you
Max:
fascinating.
Harper:
know, you kind of say that stuff and it's like. You're starting the beginning of the story in that process. So I think really it is just about trying. I think it really is put in and doing things that fit you. Like I wouldn't recommend that for everyone, but like do the thing that fits you. I have a friend that does Toastmasters and loves it because they don't have a natural way to like tell a lot of these stories. I don't understand the thing. For me to be very honest, where I got really good at this was I did a lot of street performing in the early 2000s downtown Chicago. and working in front of an adversarial audience, someone, people who don't want to talk to you and don't want you in their way, et cetera, that really teaches you to be very efficient and very good and very quick.
Max:
What kind of performances were you doing?
Harper:
Mostly juggling, we're doing
Max:
Oh yeah.
Harper:
juggling. Yeah, it's fun. If you ever saw jugglers at the water tower place in downtown Chicago, right by that little sidewalk area, that was probably us.
Max:
That's amazing. You know, you said something earlier that got me thinking. You have to know your own story and be comfortable telling your own story.
Harper:
Yeah.
Max:
I think people lose their own story for a time. when they're in their late teens, and then some portion of their 20s, depending on the person. And then once they get older, they revisit it and they become more comfortable with it. And
Harper:
Yeah, absolutely.
Max:
one thing that, what made me come back to that is when you talked about comedy, Kevin Hart has a phenomenal autobiography. And he talks about how at first, his jokes were these sort of arms length jokes that he thought other people would find funny, and he did fine.
Harper:
Yeah.
Max:
somebody that was like, you got to tell your own story man because
Harper:
Yeah,
Max:
that shit's funnier than you think and
Harper:
it's really
Max:
Once he
Harper:
funny.
Max:
started being more authentic and true to himself. That's when his career took off
Harper:
That is, I think that's absolutely correct. And you, everyone is really interesting. I love hearing people's stories. Like I know there's like two types of people. There's one, the people who talk to Uber drivers and there's the people who don't. I always talk to the Uber drivers that you can imagine.
Max:
Same.
Harper:
And
Max:
Same.
Harper:
like, I love hearing about people and people love being asked about themselves.
Max:
100%.
Harper:
And so like, if you don't have a story to tell, just be, make sure you're the one asking for the story. Like it's okay to not have that story to tell. I do think that it has helped me quite a bit, but I know lots of friends who have not used narratives to raise a boatload of money and make
Max:
Mm-hmm.
Harper:
very successful companies. So it's a little bit like. You know, smoke them if you got them, but it's okay if you don't.
Max:
100%? Yeah, I think it's interesting. It's, you know, when I thought about starting this podcast, I thought about the thread that runs through all of the things that I've done from real estate to video production and all of this, it's storytelling. And then when people ask me, oh, well, so did you start this podcast because of storytelling? And I thought, I wanted to engage more in story listening because I think that people just need a venue. They just need a stage. to tell a really interesting story and not making it into anything more than it is, but just tell the story
Harper:
Mm-hmm.
Max:
and just have somebody who's listening, you know?
Harper:
Yeah, for sure, for sure. I think that's absolutely correct. Absolutely correct. Well, thank you for providing a space.
Max:
That's my pleasure, man, my pleasure. Well, that does it, my friend, Harper Reed. Thank you for being on the show. For show notes and more, head over to mosspod.org. We're on Apple Podcasts, Spotify, Amazon, wherever you get your podcast on. This was Moral of the Story. I'm Max Drapofsky. Thank you for listening. Talk to you next time. All right, man, let me stop recording here.