Ad Ops All Stars: John Shankman, Hashtag Labs

by Jason Dobrzykowski, on Jan 26, 2022 10:00:00 AM

john shankman headshot

John Shankman, founder and CEO of Hashtag Labs started his dive into Ad Ops while on his lunch break selling to a Hoover's competitor in the early 90s, right when the blogosphere was starting to blossom.

John's interest in buzzwords, jargon, and where the internet was heading in "Web 2.0" lead him to start researching the topic and eventually landed him a job doing ad sales for early online brands like TechCrunch, Mashable, and Business Insider.

Listen in to learn more about John's journey,  his approach to the ad ops ecosystem,  and the continuing evolution of the industry.

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Jason D.: Hello. Welcome to the Ad Ops All Stars Podcast. I'm your host, Jason Dobrzykowski and my guest today is John Shankman, Founder and CEO of Hashtag Labs. Welcome to the podcast, John. Hey, John, you there?

John Shankman: Hey, what's up?

Jason D.: Hey, John. How are you?

John Shankman: Good. I'm good. How are you doing?

Jason D.: I'm good. How's your day.

John Shankman: Oh, great. Can't complain. How's your day?

Jason D.: It's going well. I'll do a little intro real quick and then we will jump right into it if that works for you.

John Shankman: Yeah. Let me just get my frames set here and we'll be all set.

Jason D.: I like that background by the way. That's a nice little staircase.

John Shankman: Thanks. Yeah. I've been digging it honestly.

Jason D.: Is this a new home?

John Shankman: Yeah, it's my house.

Jason D.: Nice.

John Shankman: Yeah. So the stair, it works. Normally, I like, I don't know, wouldn't want to show it off, but-

Jason D.: No, I think it's great. Sweet. Cool. So, you let me know when you're ready and I'll kick it off.

John Shankman: All right. We're just getting right into it. Yeah, ready. Go ahead.

Jason D.: Awesome. Welcome everybody. My guest today is John Shankman Founder and CEO of Hashtag Labs. Welcome to the podcast, John.

John Shankman: Thanks for having me, Jason. It's great to be here.

Jason D.: Awesome. So, one of the questions we like to start out with is how you would explain your job to a five year old.

John Shankman: Five year old or basically anyone not in ad ops?

Jason D.: Probably not anybody in ad ops is probably the best place to start.

John Shankman: Yeah. The most basic big thing I try and do is ask people what websites they read and say you know those boxes that have the ads in them, we really work on those systems that get the ads to appear in those boxes is basically what I try and explain. So, if you go to or Vice or any blog and you see a display ad, we are the service and technology providers behind those boxes.

Jason D.: Right. So, maybe for everyone that's listening, explain a little bit about kind of your career progression and kind of how that led to Hashtag Labs.

John Shankman: Yeah. Happy to do that. Thanks for the question. I got into the business, frankly, because I like blogs actually. I got into the professional world in the early 2000s. I was selling a technology product. I was selling access to a database actually to date myself a little bit. I'm getting old enough [inaudible 00:04:51], one of those guys who's like, I'm going to date myself here. I was selling access to like a Hoover's competitor and it was okay. It was a good job. But on my lunch break, I was starting to discover the blogosphere things like Deadspin or honestly, even like ESPN's page two with Bill Simmons and earlier Hunter S. Thompson, this kind of like giving a voice to the fan publicly kind of like getting beyond access journalism in sports.And the idea that you could publish content professionally or not professionally really, even more from an innovative perspective, not professionally and reach a large audience. That was exciting to me in a number of different ways, not only from a reader perspective, but a writer perspective. And I got really into it, kind of spent my spare time reading it and maybe trying to write something once in a while. And eventually one day at work, some random dude was like, "Shank, you should work on the internet." And I was like, "That's just the smartest thing you've ever said, Nick." I didn't know actually how to go and work on the internet. And so, what did I do somewhat ironically, I went to a bookstore and tried to find some books about the internet. And one that I found was about Google written by John Patel. And I really enjoyed that book and there was some information about John who's pretty iconic, digital Web 2.0 Figure. I think you maybe even coined the term Web 2.0, frankly or maybe not. I don't know, maybe.

Jason D.: For the record, I feel like I dropped those terms too, like Web 2.0. And like, to your point earlier, like dating yourself, I feel like sometimes when those ones, those are the terms that I say, and it's like, I look around and no one knows what I'm talking about. I'm like-

John Shankman: Well, Web 2.0. I mean, we're in the midst of the rise of Web 3.0. So, Web 2.0 is somewhat prevalent. Web 3.0 is super buzzy. Honestly, I'm going to stop this story and just tell you, you know why I got into this business, because I love buzzword and jargon. It just really drives me. So, not kidding. Anyway, I read John Patel's book. I had some sales experience. I ended up getting lucky and getting well, I discovered federated media, I researched it. It was a early blog network, a really [inaudible 00:07:32] sales house for the first independent publishing brands on the internet, brands like TechCrunch, Gigaom, even Business Insider and Mashable, their first [inaudible 00:07:43] were federated media. So, I got into the business there selling ads and that curiosity about how things worked on the web that I really discovered early on continued. And again, being an ad seller is good and it's cool and honestly, a lot of times it's lucrative if you're successful, but you don't always understand how things get from point A to point B.And I was always curious about that and that curiosity frankly led me to a couple of different stops along the way, one being HuffPost and then the next one, a smaller organization, but really one that had a great editorial brand called the All Network and that was around 2010 and or maybe a little later, 2011, 2012. And at the All Network, not only was I ad seller, I really became an ad operator and learning about things like ad servers, how to monetize ads that you don't sell or inventory that you don't sell directly. So, that's when my journey as a ad operations person began.

Jason D.: So, that's when you started to get your MBA in ad operations in real time.

John Shankman: Yeah, exactly. Which I think is sort of how all ad operations professionals get their MBA in ad ops because frankly there is no school to go to. It's really are you curious about how things work and if you are, here's a lot of documentation

Jason D.: Here's a crash course.

John Shankman: Yeah. I mean, well, I'm kind of alluding to the idea that a lot of times you have to read [inaudible 00:09:25] of Google Help Center documentation and you have to read it like 10 times to really parse what exactly you need to do and what button need to be pushed. I think ad operations is a challenging discipline. It's an exciting discipline too, because it's really the intersection of web engineering and like the business application of web engine.

Jason D.: Yeah, for sure.

John Shankman: It's like that Venn diagram is perfect for engineering and business dynamics. It's like, if you're an ad ops professional and you want to be successful, you need to have your foot in both of those worlds.

Jason D.: Yeah. And to your point, I mean, it's a dynamic position because just how you described it, the different groups that you're required to work with, like from engineering to product, to monetization, to customers, to like all across the board, it's you have to have all those considerations with every decision you're kind of making or how you're interacting and that intersection of all those places. It is truly an interesting role but to your point the education around it is real time. You're not going to school for it. You're you're living and breathing it to better understand it and to be able to do it.

John Shankman: Yeah. I mean, I think it's a great time to be curious, I think for a number of different reasons, but mostly because technologies are evolving so fast right now and ad ops is a good place to exercise curiosity about engineering with a real application. And to your second point of your question, like what does Hashtag Labs do? I mean, that's kind of what we try and do is like drive down this lane of having a really core understanding of web engineering and not letting the nuances and business details of digital advertising get in the way of sound technical decisions and implementations. And so, yeah go ahead.

Jason D.: I was going to say to your point, I mean, you talk about the team at Hashtag Labs, how big is the team there? And when you think about ad ops and goals, how are you working to kind of measure that across your team and creating those measurable goals for the team as a whole, what's your process for that?

John Shankman: Yeah. I mean, so the Hashtag Labs team is just over 20 people now. We have people in different roles, the company, again, we're like an eight year old company now, which in our time, it like I meet these companies that are like, we were founded in 2017 and they seem so established and stuff. And I'm like, man, we've been in business for longer. So, we've been around for a while now. And Hashtag Labs was originally a tech enabled services company for ad operators. And so, if a publisher needed a boutique systems integrator for Google Ad Manager or pre-bid, we knew how to do that, if they needed programmatic kind of biz dev or optimization things, we did that. And we also did direct deal trafficking. And so, the team was originally a very customer, and it still is like customer service, world class customer service is one of our core values.So frankly, customer happiness and satisfaction is probably our number one driver. If a customer is upset, that goes to the front of the pack. Thankfully because great team, our customers aren't upset too often, but things happen here and there. And so, customer satisfaction is really the number one driver because we are a bootstrap company. And so, this other thing I read recently is like, your customers are your early investors and we don't have any investors, but I mean, that really is true. And again, there is a very strong value exchange going on. We're offering our ad tech expertise and our ad ops services in exchange for essentially that money or that analogy investment. But so I mean, customer satisfaction's the number one thing. And then the number two thing is kind of just like features, understanding, making sure that we are up to date on the industry. And depending on what section of the business you're looking at, that kind of means different things like how do you optimize a direct deal campaign for viewability is much different than the implications of upgrading pre-bid from version four to version five.And so, for the size of our team, we do have a kind of different, for the size of our overall team, we do have a number of different teams within that. Whether it's the engineering team who's working on our software products or our technical account managers who are service seeing our direct deal clients. So, the metrics kind of vary, I guess.

Jason D.: No, that's great insight. It also sounded like you being in business for eight years, obviously you see a lot, but there's also evolution I'm sure that takes place in terms of where you guys started and where you are today and how those focuses change and shift over time. Maybe talking a little bit about some of that evolution and some of the shifts that you've seen in the landscape as a whole and how that's also driven how you've not only managed the team, but driven the organization into places that are like, "Hey, this is what's coming around the corner. This is where we want Hashtag Labs to be."

John Shankman: Yeah. I mean, the easiest way I've been thinking about it in the evolution of ad tech is really can be understood by where the creative is hosted, right? And so, we call it programmatic today, but for a long time it was called remnant, right? And so, when we're talking to publishers who aren't customers yet, you really want to understand the first thing you kind of like, there's kind of two things you ask, like maybe you ask how much traffic you have that's interesting. But even more so than that, it's do you have direct deals or are you monetizing programmatic exclusively or do you do a combination of both? And so, in that question, there's sort of this idea that direct deals are different than programmatic. And when you think about that breakdown, what's the big difference technically speaking?Direct deals, the publisher gets the creative tag directly and they hosted in Google Ad Manager. Programmatic the creative's coming over the supply path and is in that programmatic request and response architecture [inaudible 00:16:30]. And so, where I think the industry seems to be heading is that direct deal creatives which were traditionally hosted in the publisher's ad server is migrating over to being hosted on the DSP side. And so, as the industry evolves, publishers really need to think about what technologies are we using to get direct deals programmatically? And you have to understand the supply path really well. And you have to have this kind of inherent ad tech engineering expertise, whether that's through someone on your staff or through a platform or software platform, software product that does it for you.I think accessing those premium direct dollars are migrating from being hosted, the creatives are migrating from being hosted in the publisher's ad server to the advertiser's DSP. And so, building products that will support that notion is really what we're doing today on the product side and trying to help educate not only our current customers, but the marketplace.

Jason D.: That makes a lot of sense. You talked a lot about there in terms of like the journey to the team is making the journey that the team is supporting for all of your customers. It's a lot, right? Just in general, it's a ton for anyone in the space. And we all know for folks that are in ad ops that burnout can be real. When you were dealing with your team, maybe this is a two part question. So one, when you're looking at bringing folks on, what's your hiring process look like, but once you've got folks in, you've got a team there, how are you working to make sure that they don't hit burnout out? What are the things that you're doing to make sure that the team internally is staying pumped and motivated knowing that I mean, we live in a world of like everyone on call and like ad ops is probably one of those fields where it's like, you're always on call because of all the tools that exist and the methods that exist to get in touch with folks.So, maybe shed a little bit of light on that in terms of your strategy for hiring and then how you make sure that you keep the folks happy and understanding that burnout piece.

John Shankman: Yeah. That's a good question. Yeah, ad ops, I mean, what I've said, like ad ops is the bottom of the hill, right? And I think in the beginning of Hashtag Labs, especially our core customer for a long time has been the head of the long tail maybe, I don't know if that makes sense. But makes sense anymore but it's basically independent editorial driven high quality publications. Their first and primary product is their content and related to that, the content management system. And so, ads are important obviously, but are there enough resources at an independent publisher to take care of the CMS in the way it needs to be taken care of and ad tech in the way it needs to be taken care of? And forget about our customers, I think just at large within our industry, ad ops at those sorts of publishing organizations and really even bigger ones, it's always been like this, whether there's one person or five people, it tends to be a challenging place because you really need these engineering skill sets to truly understand it.And the engineers are strapped in, so they can't come in and understand the exact application. And everyone will admit, advertising is a little bit wonky and sometimes arbitrary and there's a million different systems. And so, it becomes very complex quickly to understand, so the engineering team doesn't have the cycles to understand it and the ad ops team doesn't have the engineering skills to make the changes they need. And so, it becomes a very frustrating place to work because people don't have the time or they don't have the skillset or the resources.So, Hashtag Labs got lucky or whatever. We basically were a tech enabled ad operations shop. And so, what ended up happening was we would bring in our own people and we would train them up. And then we would be the ad ops company for these really wonderful publishers. And it ended up kind of being a good place to do ad ops because you could learn and you weren't the only person there. You had the resources to support you. So, it became a really nice place to do ad ops when traditionally ad ops was challenging. And so, one of the things I'm most proud of is we really do have a large number of people who've been with the organization for 5, 6, 7 years. I mean-

Jason D.: It's amazing.

John Shankman: Yeah. I mean, again I'm the CEO and founder, so I'm biased, but I think it's a nice place to work and do ad ops and the track record kind of speaks for itself. I mean, and I try not to be too, there's a kind of like, this is people's livelihood. This is our customer's livelihood. It's real. Again, it's just advertising, but it's also people's livelihoods like I said. And so, we take that very seriously and we get back to people on time and I try not to create too much internal pressure outside of that. That's kind of enough internal pressure. So, outside of that, we have a pretty [inaudible 00:22:32] environment.

Jason D.: Yeah. I mean, it sounds like you've got a crew that it's almost like when, like folks that you work with or the folks who work for you, they put enough pressure on themselves knowing what they're trying to accomplish, what's in front of them. And adding more to that mix is the approach that you take because of also how you've hired the folks you've brought in the culture you've built. You've got people there, seven years, that's incredible. I mean, having folks continue to stay, which is really awesome in terms of what you've built.

John Shankman: Well, yeah. And I'll say too, just like it's about, I mean, I think because of the nature of ad ops we talk about which is kind of like a self-taught discipline, at this point, we're trying to hire pro like people who have experience, which again is few and far between, like we just hired James Strang who has incredible publisher side experience and that's been a massive hire. But prior to that, we were training our own people. And so, it was really more about, are you curious? Honestly, that was our number one thing. Like, do you want to learn a new skillset? And we were actually hiring out of these engineering boot camps, because they had sort of like a technical introduction. And then we were like, "Oh, this is where you can apply those skill sets because ad ops does have an engineering background." So, most of the team is trained internally, but now we're starting to hire people with more experience.

Jason D.: Yeah. It's interesting you say that. I in a previous life worked in for Millennial Media and AOL and we did things similar at that time back in call it 2009, 2010, where we were also looking, we were looking at financial analysts. It's like we needed an analyst, but we were just looking at people that worked at financial institutions that understood numbers and had a drive for just being curious and hiring folks that had never been in the space at all, but were great. They had a curiosity to hunger and they were great humans. They were just good people and they were natural drivers. And I feel like a lot of that in some cases, because you don't graduate from whatever university with an ad ops degree, you're looking for people of all walks of life that can kind of bring it all together.

John Shankman: Yeah, exactly. And we've been fortunate enough to find those people and retain those people. I mean, the team, I love the Hashtag Lab. Again, biased like yeah.

Jason D.: That's okay. You're allowed to be. I mean, you started, you built it. So, what does your day to day look like? I mean, in terms of where your areas of focus are kind of across the business and where you find yourself spending the most amount of time?

John Shankman: Yeah. I mean, I talk to a lot of publishers. I'm basically the front of the house for the company still. We're trying to build that out this year, but I'm sort of the initial touch point for publishers. So, I talk to them about what we do and how we do it. I'm thinking a lot about software, right? I think, I partially got into this business because I was reading TechCrunch when it launched and all these other sites and kind of started watching Steve Jobs YouTubes before YouTube came out. So, I don't know where I was watching those, but I've always been interested in technology and building software and I think Hashtag Labs again, we've grinded it out because even prior to Hashtag Labs, our technical co-founder and I were doing apps together at the earlier organization.And so, we've been doing this for over 10 years together. And so, we really have an understanding of the application. And so, now and more importantly, we have a really good understanding of the pain points that publishers experience. And so, we're in this position where we can hopefully build tools that automate and make publishers lives easier. And so, really thinking about not only how do we offer the right talent to our publishers, because that's not going to go away. I think the idea that publishers don't have enough talent in the ad ops department is correct. And it's because that talent doesn't exist and it goes back to the whole idea that it's a niche application and the education just isn't there. And so, these little organizations or big organizations like Hashtag Labs that have this specialty knowledge are born. And right now what we're trying to do without limiting access to our talent, is build platforms and tools that allow us to scale that access to that expertise.So, we have three products right now that we're bringing to market. The first one is free. It's called HTL Debug. It's basically, I don't know, again, other people besides me say it like the most comprehensive and one of the best ad debugging extensions available. It's for free on our website,, or just Google it, it's D-E-B-U-G ,that's free ad debugging extension. We also have HTL BID, which is really an ad tech automation platform. You could just call out a prebid automation platform, but it does a lot more. And then we also have a new product that frankly we've been working on for over eight years. The tightest implementation yet is about to come out and this is also an automation product. It's going to be a very efficient, a very tight tool for getting all of your data from the first party sources into one location. So, pull down your magnet data, pull down your index data, pull down your Google analytics data, whatever have you, and kind of put that into one centralized location at a great price.So, thinking about that, thinking about how to evolve our business models to support that, how to explain that to our current customer base, all that sort of stuff. So, really thinking about that automation future for publisher ad tech is where I'm spending a lot of my time.

Jason D.: There's a lot going on there. No doubt.

John Shankman: Definitely.

Jason D.: As you kind of look back on your career, who was someone that had a huge impact for you and why in terms of either, it doesn't have to be necessarily career wise, but just understanding who in your life has given you impact in a way that has helped drive you?

John Shankman: Yeah. I could go with the super cliche one, but I'll pass that one. But so, I'll imagine like Federated Media, honestly. Federated Media was my first job in the industry and they really valued independent content on the web. They built out a really great operation around that. And it was really my introduction to the business side of digital publishing or digital advertising specifically. I mean, you can't mention Federated without mentioning John Batel. Chaz Edwards was a fabulous sales leader there and someone who's affected or influenced is actually the word not affected, like is it influenced my thinking a lot, is James Gross and he has a business partner named Noah Brier who they kind of, they are now working on this idea, like software product data as to inform your sales and marketing and go to market efforts. So, those are some people who helped me along the way for sure.

Jason D.: Actually, you mentioned you actually just mention that software and had me thinking too, like one of the things that I didn't ask before was what are the tools that you guys use internally to keep on track like, just keep on top of all of the things that are kind of moving along and moving around inside of Hashtag Labs?

John Shankman: Yeah. I mean, HTL BID is an incredible tool for managing your ad tech. So, I mean, even our internal people manage our customers ad tech through HTL BID. HTL BID is probably our most used tool. It's customer facing now. Outside of that, we also use Zendesk. I'm really happy and pleased with our Zendesk implementation. What else do we use? I mean, I'm always like amazed at kind of these, what is it, like accounting solutions whether it's NetSuite or QuickBooks, like those cloud based things that are incredible. On the software tip like Segment. It takes a minute to wrap your head around what Segment is doing in terms of passing data downstream to other services. But once you wrap your head around it, it makes a ton of sense and they offer a ton of efficiencies. Yeah. So, those are some of the tools that-

Jason D.: How much time do you find yourself in like, I mean, with the evolution of tools like Slack and messaging and also like getting customers in those tools for quicker response times, obviously you mentioned Zendesk, but how much time do you feel like, and or has the time allotted evolved over your career in terms of time that you spend in messaging tools versus email and your inbox and managing that? Because obviously there's a lot of moving parts. Some people prefer one to the other, but I know that it's just interesting to hear how others kind of use the dynamic of messaging and email to basically get it done.

John Shankman: No doubt. I mean, listen, we're in Slack, Slack is big. I mean, customers like Slack too, especially in the implementation phase of things, really having a Slack access is really good. So, I think for implementation, Slack is great for chatting about things. Yeah. So, I mean, PMing, DMing, whatever, like G-Chatting, it's been going on forever. I love it. Slack is cool. Me personally, I'm a huge email guy and there's this kind of general wisdom, which is don't write long emails, people don't read them. To a certain degree, I basically don't do that. I write, I think at this point there's like a Shankman type email, which is this really long-winded over explaining a lot email, but again, in ad ops, I feel like that's almost like Hashtag Labs' thing, right?Translate these super technical wonky details of why this can or can't be done and translate that into something that a fast moving executive can understand quickly. And sometimes you need to, like communicating those things are very important in ad operations. And I think that's really, frankly my role. I'm not an ad tech engineer, but I've been fortunate enough to work with really good ones. And I think my main thing is turning around and explaining again, it's not okay, but it's very detailed, dense, wonky things in a way that a business executive wants to understand it. Obviously anyone can understand if you have the time, most people don't have the time. So, it's like how do you boil it down? And often that's sort of you expound on it in an email.And so, I find email to be very effective for that still. And so, whether it's a kind of a proposal or something's going down related to billing or why isn't this ad rendering correctly, like email is where I go to for that. Or now with the Zoom world, definitely let's hop on a Zoom too.

Jason D.: Yeah.

John Shankman: It's definitely a bit.

Jason D.: No, I definitely hear that, especially with the accessibility of jumping on a call too. I mean, it also goes back to the core of customer service and support and the world that we live in. So, second and last question. So, if you could go back to your younger self, is there any advice you'd give to yourself just in terms of what you've learned?

John Shankman: I would read O'Reilly's HTTP book earlier. The idea of requests and responses is so endemic to what we do that understanding it is so important. I read that book recently and it was just so applicable. It was mind blowing. The other mind blowing thing was that it was written in 2000 and so some of the things they mentioned are out of date, but essentially, the protocol is exactly the same. So, it's fascinating. Yeah. So, I would say read that book earlier and just stay curious. Time plus pressure equals diamonds. If you want to be something, it doesn't happen overnight. You got to live through it. You got to do it. You got to experiment and yeah, just be a good person. And if you're a good person, you shouldn't have any anxiety, something like that.

Jason D.: That's good advice, that is good advice. So, the question that we like to end on and you talked a hit on a lot of people, not only throughout your career, but even today that are doing awesome work. Who is someone that you think would make a great next guest in the space that could come and share and talk about the things that they've learned and share their view of the world?

John Shankman: Yeah. I mean, so one subject that I think is fascinating right now is supply path optimization or what I would call supply path management. So, as a publisher, I think you need to be careful because supply path optimization in my opinion is really a term that's coined on the advertiser side. And so, SPO as it's known or supply path optimization is not always in the publisher's favor, but it's happening and I think it's also important for the publisher to understand how are ad buyers, whether they're direct advertisers like Netflix, or sort of like downstream middle men who are just buying and reselling inventory, accessing the publisher inventory? How are people getting bids and winning bids on my page? Trying to understand that as much as possible and what games are being played around that on the publisher side is super interesting and super important.I did an ad week panel in Q4 last year with Chris Kane of Jounce Media and the prep for that and thinking about that and talking about that with my team really helps solidify a lot of my thinking about where the industry is going and how publishers can prepare themselves for the future and really protect themselves in the future. And so, I would recommend Chris Kane from Jounce Media on the topic of supply path optimization and how that pertains to publishers.

Jason D.: Awesome. Well, we will definitely work to get them on and we appreciate the recommendation.

John Shankman: Yeah. You got it. Yeah. Hope he gets on the show. It's always good to hear Chris talk.

Jason D.: For sure. Well, listen, John, I really appreciate you taking the time to sit down with me today and walk through kind of your experiences and sharing with the world what we all know, love, and breathe, which is ad ops and more about Hashtag Labs and kind of the founding there, but just wanted to thank you for the time and we definitely appreciate you coming on today.

John Shankman: Yeah. Thanks so much for having me. Honestly, I'm proud to be an ad ops person. Hopefully people are okay with me qualifying myself as an ad ops person, but yeah, I'm proud to be an ad ops person. It's great to be a part of the podcast and thanks for doing it. Looking forward to seeing you out there in the industry.

Jason D.: Absolutely, John. We appreciate it. You have a great rest of your day.

John Shankman: You too. Take care [inaudible 00:40:02].

Jason D.: Bye.

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