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The Community Podcast #16

The Life and Times of Harper Reed

Harper Reed is an American technologist, known for his role as the Chief Technology Officer for Barack Obama's 2012 re-election campaign, his involvement in pioneering online crowdsourcing company Threadless, his hairstyle, and many other weird and wonderful projects he gets involved in.

Severin met Harper at MIT’s media lab in Berlin, in August last year. Being a fan of Harper’s work for many years, he took the opportunity to ask him about what Harper calls his life waves: periods in his career when he quit everything and said yes to any new opportunity that came his way.

Like this interview. Or building one of the first crowdsourcing communities on the internet. Using social technology to get a president elected. Or predicting the future for a living. All this, and more, including sirens and pan flute recitals, in episode #16 of The Community Podcast.

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*We got a little help from a robot to type this transcript, so please forgive the possible typos still left in the text. Quotes we love are highlighted in red.

Severin: Harper, very happy to have you here. How are you today?

Harper: Wonderful. 

S: To start with, tell me about your life. I saw on your website you basically just started what you call the third wave, or third chapter. What is that?

H: Well, every few years–I don't even know if it's years really as much as it is experiences–every experience, I like to break up with a very elaborate break. I don't even know how to describe it other than I try and quit everything and then see what happens. I left my job in April and I've just been saying yes to strange things. Whenever someone says “Hey, would you like to do this?” I try and say yes. If I can't say yes for some reason I try and help in some meaningful way, and if I can't help in some meaningful way, I try and connect that person to someone who can. I find that this kind of engagement is really interesting and it really opens up a lot of doors and it makes, it just makes the world smaller, which is I think one of the goals, trying to get it as small as possible. Eventually I think I want to start another company or join a cool team or something along those lines. Right now it's leaning towards starting another company, but I'm not trying to force that or find that answer immediately. I think there's a lot of things in life where we know what we're looking for in an approximate form. Like I say, I want to start a company, but we don't know what it actually discretely looks like. And yet sometimes we just really want it so bad that we forget that we have to get there, that there's a journey to get to that place where the discrete form appears. And right now, I don't know if it's just because I've done it a few times or if this is, this is my third time of doing this, or if I'm just a little more fatalistic at this point, or if I just have a little bit more privilege and can take some time off, but I'm enjoying the process.

S: Tell me about the first and the second wave. What happened at the first wave, what happened at the second wave?

H: The first wave was in maybe 2004-5. I was working for an ad agency and I got laid off. I was happily laid off. I had a little bit of, um, I just didn't like the job. I enjoyed my coworkers, I liked some of the work. But that was when I discovered that I am interested in one product and working on one product. In that way I'm kind of a serial monogamist. I Just want to work on one thing and work on it really well. Instead of having a lot of clients, you know, with a capital C, I want a product with a capital P. That was a good discovery. And so I got laid off in like June, so I had a summer. It's like the best time to be laid off, especially when you're young, you know, there's not a lot to lose, and I traveled a little bit, I spent some time with some friends. I was a podcaster actually, for a vodka company, so I went to clubs and podcasted, it was very bizarre, I worked a little bit with Seth Godin. And eventually, through a lot of synchronicity and random experiences, I got hooked up with Threadless. And so the first kind of break was leading into Threadless and I had no idea what I wanted to do. I just knew I wanted to work on something that I felt was really cool, that fit my personality, that was interesting, and Threadless just kind of appeared out of nowhere and I'm really happy that that worked out. Eventually I became the CTO at Threadless, that was a lot of fun. And then the second one was when I left Threadless in 2009. I just knew I was done. You know, I remember describing it to some friends as if I was at a big dinner party and the dinner was over. Like you just kind of get up. There's no hard feelings. It's just like “Okay, I'm done with that.” We'd done a lot of really neat things. I was really proud of the work that my team had done, that I had done, that we had done as the collective Threadless. I felt like in some ways we'd created something that changed the Internet, which was exciting. But I needed to figure out what was next and I felt, um, stifled is the wrong word, but I knew there were bigger things, and I didn't know what those were. So I spent about two years, honestly just kind of screwing around. We would have some kind of collaborative event at coffee shops in Chicago and I would email friends who had companies and say “Hey, I'm going to be in, you know, New York for a week, can I hang out at Etsy” or whatever it might be, hung out with a lot of kind of strange people doing strange things. And eventually the co-founder of my company, Modest, Dylan and I, we decided to kind of start a company and we started to play around with starting a company and then out of nowhere the Obama came, Obama campaign swept and picked us up and we did that. But it wasn't planned, it wasn't, um, we had no idea.

S: Maybe before we go into the Obama campaign, because I have a lot of questions about that, you mentioned two elements that I'm really curious about. One is Seth Godin, the other one is Threadless. Seth Godin for me has always been an inspiration and I think he's one of the few people who keep on delivering year after year and coming up with useful stuff. How was it interning with Seth Godin and what did you learn there?

H: It was a little bit of a nontraditional internship because I was, I don't know, 25 or something. I was on my second job, I was kind of early, mid-career and I took a chance, because colloquially it seemed internships where for people that are coming out of school, you know, coming out of like trying to get started and I needed a way to disrupt my path, and it did. Seth is an amazing thought leader. He's an amazing marketer. He has a vision that is very interesting and thoughtful. What I find interesting about Seth is that he had a lot of mystique. Like there was a lot, like I remember he brought us out to New York to do a website that he pitched us on that first day, and the next day he was like, “Just kidding, this is what we're actually doing.” And it was like he was doing it just to kind of see what our reaction was, like how we would handle it. It was very interesting. I have found Seth to be an inspiring individual. I have not read any of his books, but what I really liked about Seth is that he is a machine. He's a factory, in almost the Andy Warhol sense of creating opportunities and outsourcing as much as possible to be very positive. And all this stuff he's creating is really interesting, so it's pretty cool to see him just keep trucking. You know, I remember hanging out with him during that summer, learning a lot about what it takes to build a company, what it takes to build a business, how you build up an advisory team, how you build up a team. It was really helpful for my career, but I bet I didn't notice at the time how helpful it was, and only when I started my own company I reflected on “Oh wow, like this was a good preview.”

S: What happened then at Threadless? I remember Threadless being a pioneer in crowdsourcing. And I think, as much as I know, it happened a little bit by coincidence, but when I worked back at my company in around 2007, 2008, we started crowdsourcing as well, produced books with photographs from our community. And Threadless was a big inspiration because you guys just did it so smoothly, and I loved the language and loved the way it looked like. And you know, I think, looking at the landscape today, we have so many marketplaces, Airbnb and Kickstarter and Indiegogo and so many other places that I think built a lot on the principles that, you know, sites like Threadless developed. So in hindsight, how was it working on Threadless and what did it mean?

H: Well, Threadless was interesting because we really truly–well I don't actually know if it's actually true, but we seem to have invented crowdsourcing in a meaningful way for the Internet. And that's confusing because we really truly were just trying to make cool shirts, we weren't trying to do anything fancy. We just knew that the coolest shirts weren't going to come from us as individuals, they were going to come from this community. And so “How do you build a community?” is the question we were trying to answer. And it was actually difficult at times because we believed so strongly in the community that we stopped listening to ourselves sometimes. And I think that's where, um, I don't know if Threadless went wrong, but I think that's where we started to lose sight of what we were doing. It needed to be a collaboration between the community and the curators of the community instead of just the community. We felt ourselves as shepherds of the community, but we didn't necessarily participate in the community. We felt ourselves as these folks that needed to make sure the community was happy, but we weren't actually listening. We were just, we were just listening to the reactions. We weren't proactively listening. So Threadless was really interesting, especially interesting when you look at it in the history of the Internet. At the time we were honestly just screwing around. We were, you know, I mean it was making money, things were working out, everyone loved tshirts, especially the tshirts that Threadless made. It was really fun and really cool, it taught me a lot about ecommerce, taught me a lot about community. But I kind of wonder sometimes where we all went wrong, in that crowdsourcing was this very special thing, and one of the magics of Threadless, I think, was that it actually was pretty small. Now, the number of tshirts we sold was not small, but the community itself that created those shirts was small. And it really, the challenging thought that I always have is: if you grow a community, does the quality stay? When you look at the early community of Vimeo versus Youtube, Vimeo had the better quality, but Youtube was growing way better. And even today, if you look at Vimeo, it's a much smaller, but it seems to be a much more vibrant and better community. Whereas Youtube has a very good pop-y kind of viewership, but the long tail is just a bunch of really weird, weird videos that I don't understand, because anyone can upload. And so I just think a lot about, if we were to build Threadless today, would you want to create a more exclusive community to ensure quality or would you want to have a bigger community to have better crowdsourcing or bigger crowd? I don't know the answer and I don't know if we found the answer at Threadless because the Internet changed so drastically, kind of underneath us.


S: Very interesting. I also have some thoughts on that. I worked at a photo community, we had 22 million photographers on our app, and we also started selling photos, on the stock market. And at some point we made an analysis to see which of these photographers actually make the most money on our site. And we realized out of 20 million people, it was a thousand, you know. So we also thought, okay, should we only focus on these thousand people? But we realized these thousand people might make the most money because they take the best pictures, but there’s another large group of people that enable these photographers to do what they do, because they are the people who like everything, who comment on everything, who are super passionate–that the super superstar photographers don't have time to–and they’re equally important. So I think every community has different actors with different roles. And it's not always the people who produce quality who necessarily provide all the value.

H: Yeah, I remember we did this analysis at Threadless where we looked at the community and we looked at the people who were creating the actual art and then we looked at the people who were buying it. And none of them ever mixed. You know, the people creating it didn't really participate in the community as much as we wished. The people in the community never bought anything. And the art, it has never bought anything. So we had like three distinct communities. We had the people that created, we had the people that hung out, and we had the people that purchased. And then the thing where we may have lost it was, there were very few people inside of Threadless that were part of any of those communities. In the beginning, we were all part of those communities. We all spent a lot of time participating on the forums, Jake and Jacob, you know, they were wearing the shirts, they were buying the shirts, they owned it, you know, they were like really owning everything about it. There were participating on the forums. Everyone was, everyone should submit a shirt, everyone should try out the process, everyone should hang out. It was very collaborative in this very interesting way. And then as we got busier, as we got more serious, as we've got some investment, as we hired more executives, that disconnect started happening where we weren't participating in that community. And I was guilty as much as anyone else. I never wore Threadless especially at the end, I was interested in a different style of shirt. And I think that's what kills a community, if the founders, if the leaders, if the collaborators, if the people who are the stewards of that community stop participating, I think that's when the community starts to die. Not a true death. They just lose the leaders. They lose the inspiration, they lose that kind of, that beacon for why they are there.

S: I think that's a very nice transition to start talking about the Obama campaign. I read a few things, other interviews that you've done and I read about your thoughts on what you've done there when it came to data, but also how it's connected to leadership and to culture and what you achieved through the combination of these. Maybe you can give us a quick roundup of your memories of working at the 2012 Obama campaign.

H: In some ways, just from my memory perspective, it almost seems like the Obama campaign was longer ago than Threadless, when obviously it wasn't, it's just, it was such an intense experience, it was so amazing, it was so terrible, it was so incredible, it was so hard. Afterwards I started joking that, when someone says “That was a very rewarding experience”, that was just code for it totally sucked. But you can't say it sucked because it was so important. And that's kinda how I felt about the Obama campaign. I really enjoyed it. I look back at it fondly. I look at pictures fondly, but I also kept a journal and when I read the journal, it's a journal of just frustration, of like anger, and the reason was because it was for the first time in my life, I was doing something that I knew I couldn't fail at. Tshirts, what happens when you fuck up tshirts? Like someone just doesn't get it for Christmas or their birthday or what have you. You know, it's like the worst thing that can happen is your tshirt is a couple days late. And it's 20 bucks. You know, that's not bad. But when you're at that level, the Obama campaign level, when you mess that up, it really messes things up and it can be really bad for a lot of people. And so the pressure was just unbearable, but every day you would go in and you'd think, this is really stressful. And then you'd see all these amazing collaborators that you are working with, these people that were the smartest people in their industry, whether it was grassroots organizing or raising money, they were truly the smartest people that had ever been invented for that role–as your collaborators, as the people that were sitting next to you, as these people that we're teaching you how to do your job. It was amazing. It was such an amazing experience. I sometimes get asked, you know, would you do it again? And it's like, I would absolutely be the CTO of the Obama campaign in 2011 to 2012, absolutely. Without a doubt. Would I do it again in the future with a different candidate? I don't know, because my drive, like we talked about in the beginning, I'm very product focused with a capital P, which means that I have to have the candidate, the candidate has to be amazing. They have to be this person, this beacon, they can't be just some random person I'm sort of interested in, because I want to give 100%, 200%, I want to give as many hundreds of percents as I can give. And I want to make sure that when I'm calling all this network that I've created over the last 20 years and say “Hey, will you join me on this crazy quest?”, I'm doing it because it's something I believe in, because I often think we make the mistake of believing in the thing that we know is not quite what we want to believe in, but we're like, well, I believe in the salary, or I believe in the perks, or I believe in the fact that this company is going to go public and I'm going to make money, but you don't believe in the company. Like I don't want that. I don't want that. So when I think about the Obama campaign, it was such a good example of this thing where even though it was very hard, the hardest thing I've ever done, even though it was so stressful, the only time I've ever been super stressed, I didn't mind inviting 100% of my peers into this thing and say “Help us out”. It was the right thing to do, it was the thing that mattered. Now when you think about what we did, there was a lot of software we built. There was a lot of technology we built. There was a whole bunch of stuff that we invented, brought to politics. Many of it, you know, in some ways paved the way to 2016. You know, our use of Facebook, our pioneering use of social media, but many of it were so drastically different than what politics is now. I just start to wonder like, why did we do it differently? An example is, we were so proud of what we did that every single thing we did, we attributed to the Obama campaign. There were no secrets, there was no hidden anything. We were just like, “This is what we did!”. We were so proud, almost nerdy, you know, like we're just so excited about what we did and we just were, we weren't trying to hide anything. And I think about today and what we see on the Internet, you know, there's a lot of misinformation all over. It doesn't matter what country you're in, what political side you're on. It seems to be misinformation everywhere. And oftentimes it's obfuscated by who is creating it. What happened, where did we lose this? I don’t know.

S: One thing that comes to mind is, you mentioned in an interview, and that relates to product with a capital P, that, after the Obama campaign in 2012, a lot of people talked about how data won the election, right? And obviously that came to you, “Hey, you were the CTO of the Obama campaign, how did you do that?” And you kept mentioning that it wasn’t data that won the campaign, it was Obama, it was the leader, it was his charisma, it was his leadership. And the products that we've built would have been fundamentally different if we would have built them for Hillary or for Trump or whoever. So that means the technology that we use is heavily influenced by the people who direct it and the values that they probably put into that. What do you think about that?

H: I think everything is aggressively dictated by the leadership of whatever organization you're in. Culture comes from the leaders, from the founders. I believe that really strongly. When you look at some of these great organizations to work for, it's probably because they have good leaders. If you look at the places where people are like, wow, that place is just terrible to work at, it's the same, and the products fall from the same tree. When you have a very strong, very positive, very charismatic, optimistic leader, you'll have products that will reflect the same. And I just don't want to work on a pessimistic product, a product that is predatory, a product that is assuming bad intent of the user. And we're at an interesting time of the Internet right now. When I think about what a product like that looks like. We’re so thoughtful about user experience, but oftentimes it's defensive, we’re so thoughtful about how do we make the best, most inclusive experience for our users, but really we're just like, well, it's like a tree of “if” statements: if they have a mobile app, do this, if they have this, do this. It's not really inclusive in a real way. It's just forking in these different paths. And I think our capital P product decisions are the same. And I think a lot of that is because we really don't have good leaders in many of our products, and I don't know what happened. I don't know why this is and maybe this is just me kind of yearning for an Internet of old, being an old person. I don't know what that is, but there is this aspect of like “What happened?” There's a group of us, all of these, that kind of founded companies are built things in 2004 to 2010, we were looking at each other and we're just like, what happened? How did it go so wrong? And then at the same time, maybe this is us just getting old. Like maybe this is us just kind of the thing that we thought was going to happen didn't happen. I remember when I first started reading Jaron Lanier’s books, I really disagreed. I really thought, you know, maybe I think this guy's wrong. I think he just saw the same thing we're seeing now where now we're meeting my peers who’re reading his books and who are like, yeah, this is actually really appropriate, maybe the Internet isn't the right thing. Maybe it is causing more problems than it is causing good. But I still have hope, or I would do something else.

S: I would say that right now, with this notion of, okay, the Internet is broken and this is not what we wanted, the biggest hope on the horizon is blockchain and decentralization. I think you also have some very strong opinions on that. What do you think about this new generation of people building on blockchain, building decentralized networks and hoping to break the monopolies and reinvent the Internet?

H:  I really love decentralized, distributed networks. I think it is so cool. The technology that blockchain is based on, some of the stuff that's built with blockchain is very, it's very future. It feels good. It looks good. It's neat. You're like, this is crazy. There's this thing about it that's just, it's just such an amazing new thing. But part of being a new thing is that people who are excited about are like “I got my new hammer, I'm going to hit all these nails” and everything's a nail and you're just whacking blockchain on everything. The difference between blockchain and all this kind of new crypto stuff is that it is very, very different than anything else we've seen. For the most part it was just like the web and we iterated on the web, and maybe blockchain is the new web. Maybe that's the new thing, but when you look at blockchain and what you can do, it is so drastically different than anything we could possibly have done with the Internet in ‘99, 2000, whatever. When you think of the innovations that happened in the Internet in that time period, you had Joshua Davis doing amazing things with Flash. You had inventing ecommerce, you had all these folks that were doing, you know, document management. Like these were huge topics. People had PhDs in document management, you know, but now you think about document management and it's like, oh, whatever. So I think that's where we are now. We're going to start seeing, we have, I mean, Bitcoin's been around for almost 10 years, we're going to start seeing crypto currency solutions that are actually going to work. We're going to see blockchain solutions that are actually going to work. No longer are people going to just say, oh, I have a blockchain database for this stupid project, like blockchain for pets or what have you. We're gonna start seeing actual application. And there's a lot of haters about blockchain. And I think that the warning for us all who have hated on blockchain is, we're going to be left behind if we don't just kind of get a handle on it. That doesn't mean you can't hate. It just means that, you know, none of us want to be Cliff [Clifford] Stoll. Cliff Stoll was a physicist and he famously wrote a book about how ecommerce is never going to work out and newspapers will survive. And he was just plainly wrong. Yet he's a very smart person and he was very well respected. And I think the word is “was”, because he made such a giant statement that was like, the Internet will not work. And it's like, I think a lot of people are going to be Cliff Stoll in this blockchain kind of world. With that said, right now it's fun to be that way. It's fun to talk shit. It's fun to make fun, a lot of people have made a lot of money with it, but I think we're on the cusp. I don't think we've seen what it can do. I've set a bunch of times, I think the only use for bitcoin is buying drugs, or laundering money, which I think is true. That's the biggest usage of it. But that doesn't mean that's all blockchain solutions are, or all cryptocurrency is. I think there's some big problems with how we go about looking at that. And I think there's some huge issues with regulations in that, which is funny to say, but we just have to, we just kind of have to figure that out. And so personally, my view on this is: how do I create an environment where people can innovate, where people feel that they can do exactly what they need to do on blockchain, but also create a skeptical environment. So how do you have the role of a skeptic without shutting down every opportunity, without shutting down innovation? Because when we came up with the Internet in the 2000s and the late 90s, there were a lot of people that were skeptical, but no one told us we were bad. No one told us we were doing bad things. But right now with blockchain, a lot of people are saying, this is bad, this is stupid, you shouldn't do this. No one told us that, and we invented amazing things. So why shouldn't we let them have their time?

S: Going back to where we started with you starting the third wave in your life right now, and taking this process and kind of just looking where you go, in relation to technology and the Internet, which I think has accompanied you for at least the last 20 or 30 years – do you see your role maybe as someone who has seen a lot, has built a lot, who is now getting into a position of advising and stewarding the next generation, do you see yourself a little bit in that role?

H: Yeah, I mean, yes, I think so. One thing that I really love, I always love connecting people with companies where they can get a job. I love that so much. It's my favorite feeling, when you are able to connect someone with another person and they are able to work together in a meaningful way where both of them are very happy and rewarded. I just love that. I also really like helping people in any way I can, especially on the startup side, just because it's so hard, and oftentimes, when I had my own company, I was like, I just needed as much help as possible, and if I can offer just a small amount of help, it feels so good to just see something come to fruition, even if it's just as silly as, like, “Talk to this person” or “You're doing fine” or “Let's just go for coffee or ice cream”, you know, like just hang out, because sometimes that's all you need. So yeah, of course I do feel, I actually feel that those of us who've done things really have a responsibility to be good advisors. But we also have to make sure that we're not just using what we think should happen in the future as our advice. We should only be using what's happened to us in the past as our advice, because what's happening in the future, we don't know, and it's gonna be totally different than what we did. And so if we're thinking, oh, you should do this, that's bullshit advice. But if you're saying “Oh, I did this when that came up in my company”, that's good advice. And I think that's one of the biggest problems that we have. Oftentimes, especially as startup people, we think of startup advice, we just say it. And what we're really saying is these are the lottery numbers that worked for me. This is how I won the lottery. And it never works for anyone. It's like so silly. It's just like, oh yeah, use my numbers. Here they are. You know, this worked for me last time I won. And it's like, that doesn't actually work. But what does work is telling stories about your experience because people can derive the little nugget that works exactly for them, for their experience. And this is where empathy is such a big important thing, especially for advisors. And I also think for startup founders, when you're thinking about users, you have to have empathy. I think that's the one thing that's missing from tech. Maybe that's how we screwed up the Internet, it was just not focusing on empathy. But right now I'm thinking a lot about empathy. I'm thinking a lot about what does it mean to start an empathic company? What does it mean to have that as part of your core? We tried that with, at my last company, Modest. We spend a lot of time thinking about empathy within hiring, thinking of building the team. And it worked out amazing. We had such an amazing team and they were so thoughtful, they were so user-focused. Every move we made was exactly for the user and it was the right thing to do. And it was a great team of people who thought differently. It wasn't a monoculture. We could have done better in certain ways, of course, we could've done worse in a lot of ways as well. But I was really happy with how everyone not only got along and felt like we were headed towards the right place, but also they were very thoughtful about it and in a way that I wasn't. And that's the best part about a team. That's the best part about advising. That's the best part about creating a platform where everyone is elevated.

S: Final question. If someone comes to you and is about to start a company, wants to do something, what's your advice? What's your no.1, no.2 and no.3 advice?

H: I have boring advice for people who are starting out. The first thing you do is you got to get a really good lawyer. It's just this funny thing, like I’m probably on the side of the people that's more creative, which usually means that organization is not a priority, being organized etc. But the thing I learned with my last company, Modest, was making sure you save all the files in the right place, making so you can find every single little bit, whether it's a freelance contract, or an NDA, or a lease, or whatever. Make sure you have all those saved, scanned, archived in such a way where you can find it at a moment's notice. So often we get so caught up in the product, so caught up in running the company and programming and building and designing and whatever it might be, that we forget to do the simple stuff. When we sold our company, from pretty much first contact about acquisitions to closing it was about six weeks. And the reason we were able to do it so fast, which was actually really nice, was because we had our shit together. We had a very good, document repository with 100% of everything about the company, our IP, our employees, our leases etc., and we started that on day one. So day one, we started creating a folder structure that allowed us to know that stuff. So if I had a new employee start and I needed to know the new employee agreements, they were right there. If I had a contractor that we really wanted to hire and we needed to move fast, they were right there. We didn't have to like search or tread water or wait in any way. Because I think one of the biggest things that I learned about starting a company, this is probably number two, is that speed is everything. It's not necessarily speed, like you have to go fast, it's just that you don't ever want to let something drop. So if you're doing sales, it's always about, like, make sure you're always following up. You never want to take a weekend, take a week off of that. And that's with everything, hiring, building etc. You just need to be on all the time, which is probably why startups are terrible. The third one and I think this one is, I think I forgot it actually. Maybe there is no advice. Maybe that's the only two advices you need. Just be prepared. I think that's what it is. Be prepared, be ready for stuff. You know, I think when I think about hiring sales people, for instance, the best salesperson is the prepared salesperson. It doesn't matter if they're outgoing, if they're an introvert, extrovert, it doesn't matter. If they're prepared, it's great. And, uh, yeah, I don’t know, there's so much. This is like the problem with startups. There's literally so much, and I just broke my own rule, by just giving advice without examples of my own past. So I think that's time for me to go.

S: Thank you very much, Harper.

H: Thank you. It's been a pleasure.

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