Can Shmoop 3.0 Transform the Way We Learn?

The quirky company’s new CEO Andy Rahden is taking the popular study tool to a whole new level of fun and function.

INTERVIEW | by Victor Rivero

Nothing gets Shmoop’s esteemed head honcho Andy Rahden pumped up quite like digital learning and educational technology. Before hopping aboard the Shmoop train, Andy was the Vice President of the Pluralsight Creative, Design, and Engineering business unit. Armed with his passion for democratizing education, Andy built teams at Pluralsight from the ground up to forge strategic partnerships and create a world-class customer experience.

“I’m a builder. I’ve always been interested in building teams. And this introduction to what Shmoop was doing in the marketplace was extremely interesting to me.”

Since his early days as a Mechanical Engineer at Baker Hughes, Andy has always enjoyed building things, from mechanical stress tests to Marvel-worthy teams of super-employees. Prior to Pluralsight, Andy made his way as an all-rounder at Autodesk, where he directed sales teams through all elements of improving customer experience. He has also worked for the largest SolidWorks reseller, where he provided in-person training, worked with customers on implementation, and provided guidance to companies transforming their design process.

Victor: So congratulations on the new—relatively new role. About a month?

Andy:  Yes, in the middle of transition; signed a bunch of documentation and just recently joined. I made the transition out of Pluralsight and then moved over to Shmoop. Super exciting move, a lot of work to do and we’re really excited about where we’re going.

Victor: About your association with David and Ellen, what prompted you to make the jump. You have quite an edtech background for starters. You must have known about Shmoop from years back, even as an outsider—did you personally know David already?

Andy: No, I actually didn’t. We met as we progressed, it wasn’t really early on, but late in 2018, I think it goes back before then. But I started my career as a mechanical engineer. I was completely outside of the edtech industry. When I was at Autodesk, we had some pretty big challenges with the product development that we were working on, and how fast we were releasing products into market. And trying to educate or help people understand the new features and functions that we were releasing month over month, week over week.

That started to expose me into some of the need in the edtech arena about a decade ago. That introduced me into my direction that I went at Pluralsight. I spent a few years previous to joining Pluralsight in exploring some concepts with the founders of Pluralsight on how we could help people really learn technical skillsets that they needed in order to enter the workforce. Or maybe progress their career in the workforce.

I started working with Aaron Skonnard at Pluralsight in developing some concepts about how we would take stuff that was outside the arena of what Pluralsight was currently working on, which was like C++ development and things like Java and IT practices. And how we could introduce things that were focused on products like Adobe, Autodesk, and a variety of other technical but non-technical solutions. Things that were a lot more entertaining to what they had started working on.

So I went and started Pluralsight Creative LLC, which now makes up half of Pluralsight’s content on the platform. So I had to learn how to build teams to actually create video-based training content, which was not the easiest; nothing had been—it had been done before by some people—but not in the way that we were really thinking about doing it. As I progressed through that, the team continued to grow. The market continued to digest. And we moved into public offering in late 2018, which brought me to my introduction to Dave and Ellen.

As I started to continue to think about my career and where I would go post IPO, it really—I’m a builder. I’ve always been interested in building teams. And this introduction to what Shmoop was doing in the marketplace was extremely interesting to me. So after being introduced to Dave and Elle, we met all the way through to the end of 2018 into the beginning of 2019 and very quickly determined that Shmoop had a lot of opportunity for expansion into things that they weren’t even investing their time in at that point in time. We talked about how Shmoop could expand its presence into—not other markets, but in other ways in forms of learning for the current user base that they had today. And also some different branches or other people that were using it that we could more effectively create content for.

My introduction was really late 2018.

Victor: You’re really a mechanical engineer at the core—I think they’d make great CEOs. It’s interesting that you’re coming from that sort of background because there’s some real technical expertise there. There’s a certain mindset or a thinking that a mechanical engineer brings—

Andy:  Problem solvers. Yeah, yup.

Victor: Yeah. Interesting. And with Shmoop—as opposed to maybe some other companies, even companies you work with, there’s more personality there. Look, there’s a lot of personality in any company, but Shmoop is like an old-time CliffsNotes but with a lot of personality and in the Digital Age—a fair characterization? Certainly there’s more to offer; content will stay fresh; you’ve got videos. And that’s something that you’ve worked on in the past. Is that an area where you have quite a bit to bring that Shmoop probably hasn’t gone into in as much depth? As you’ve said, they have a lot more potential…

Andy: Yeah, absolutely. Right now Shmoop is engaging content for the learners that we’re aiming toward, which is teachers, students. I like how you said, it is an all-current solution, or it can be something that’s placed in the classroom. Today Shmoop is really a cost effective solution for schools and districts with content that’s been provided from some of the best in the industry—some of the best minds on the planet, from students and teachers from Princeton and Stanford. We really provide advanced academic credentials into any school that would use the product. We’re really democratizing that learning today.

What Shmoop is providing is entertaining and it’s awesome, but it’s also extremely meaningful. It’s one of the reasons I decided to make a move here. When you think about investment in learning today, the B2B space, businesses are spending hundreds of millions of dollars. If you add then all together, they’re spending over a billion or 2 billion dollars in the industry per year for their employees. Shmoop is bringing that investment into the classroom. We’re really investing in the generations of tomorrow before they enter the workforce.

What Shmoop has done up to this point in focus on things like literacy, math, sciences, and bringing that to the classroom; there’s also opportunity for us to expand into practical skillsets for things like career prep. That could be targeted for anyone who wants to learn a new topic or a new industry, or move into a new field. There’s a lot of opportunity for us to keep that engaging entertainment factor that Shmoop today provides. Then there are also a couple things that we’re really focused on as we progress forward in providing more to the industry.

Today, we’re really investing in our product and our user experience. We want to redefine learning delivery through updating our technology like no one else has really done before.

“We want to redefine learning delivery through updating our technology like no one else has really done before.”

If you think about how learners learn today, in the classroom and outside, we really want to change that and make it more progressive. We’re going to update our product experiences early next year to provide the most effective content curation. We have really exciting plans to release a progressive new user interface as well as updated learning methods for tomorrow. Both inside the classroom and outside. So there are a lot of things for us to work on.

Victor: When you say progressive are you talking about in terms of technology? Or, how so?

Andy:  Yeah, in terms of technology and the content. When I say “progressive” there’s a way that a learner comes into the platform today and might digest something. It might be Shmoop’s platform, it might be any learning technology’s platform. There’s a way that you walk into a classroom setting today, and you sit down, and you learn from a teacher. Schools have spent—and teachers have spent— hundreds of years perfecting the ability to teach information to a learner.

One of the benefits that I had when working at Pluralsight is we started to learn how people digest content. We worked with MIT Learning X’s platform, as an example, to understand how many topics should be taught per second in a video and how long somebody will stay engaged in a video.

So in order to communicate information, the platform that is providing that information has to be able to communicate that and curate content in such a way that a teacher could insert that into their curriculum in a really easy way. If it’s not easy, the teachers won’t use it. We want to improve the product experience to be able to be, quote, “progressive”—in the way that a teacher would integrate that into the curriculum, and the learner would digest it.

Even further, from a content perspective, Shmoop has the true foundational principles that we need already today from a literacy, math, and science perspective. We want to bring into the scope concepts of, specific topics around career preparation. If students are prepared to enter the workforce out of elementary school rather than out of high school or out of university—well, the concept is:

When I was a student and I had to go enter the workforce, I was not ready for what I needed to know when I first started working as a mechanical engineer. I did not know the things necessary to be effective in my position. It would have been a lot easier for me to decide, “Hey, I wanted to go into mechanical engineering or into something else,” because I only ended up being a mechanical engineer for a couple years. And I worked in the mechanical engineering industry for a few more, and I’ve completely changed my career direction.

There’s nothing wrong with that, but it might have been helpful for me to know exactly what I was interested in much earlier on. I probably could have made a lot more progress in career and in my life if I would have known that much earlier on. It took me years to figure that out.

If we can get started with those students earlier by providing them those tools inside of an effective product, and also the content that relates to what they’re interested much earlier on—then that, to me, is “progressive.”

Victor: Thanks for clarifying that. I think that’s interesting to bring into the earlier grades some real practical, workable, common sense kind of stuff that’s future relevant. That’s great.

Andy:  It’s real, too. My kids have already rapid-prototyped stuff in our house. That’s something that I didn’t do until I was 25 to 30, you know? They’re ready for those things. We just maybe don’t treat them like they are.

Victor: Alright, well good! Evolution at work. Very nice. On the brand itself, all brands would love to be different, and I think Shmoop does this very well—just because it is, well, different. Any thought on the voice of Shmoop and keeping it consistently quirky? How hard is that especially when it was one guy’s voice to begin with? Part of the story was that David [Siminoff] was just writing blogs and it grew.

Andy: It’s a challenge that we’re facing head-on right now. We’re actually in the process of creating our first video-based technical content by keeping the voice of Shmoop alive and active. It is something that we’re going to continue to do. And we really feel like we’ve found solutions of how we scale that so that we can get involved in other aspects of content. Dave’s voice has been present in most of our content that we’ve delivered today. But we also realize that we want to be able to scale across additional segments or other areas without Dave’s involvement.

We started dabbling in our first videos months ago on how we could utilize other authors and other experts with the feel and concept of Dave’s voice and the Shmoop voice. So yeah, we’re absolutely going to keep that. We feel like an aspect of keeping our content engaging and humorous in the delivery of it is something that keeps people watching.

The first time you watch one of Dave’s videos, it might be a topic that you’re not even necessarily interested in, but you might watch it and you find yourself extremely engaged in that “Shmoop voice” that we’ve provided. So yes, that is absolutely something that we’re going to continue, and we feel like we really mastered and figured out a way to actually bring that to market.

Victor: Wow, sounds like there were even a few meetings on it.

Andy:  Yes, yes.

Victor: There’s been hard work and sweat.

Andy:  Yes.

Victor: There’s always a bit of hard work and sweat that goes into what’s seemingly “easy” to pull off, but not necessarily.

Andy: —at all. To keep a user engaged, and also not interjecting too much; it’s not just a video full of jokes. You’re really getting across specific points of information to the learner. And balancing how much information is coming across to the learner mixed with keeping it engaging, mixed with keeping that voice or that band alive, becomes really challenging—but we’ve been able to master progressing that forward.

Victor: So, where’s it all headed?

Andy:  Business was launched in 2008, today we have 10,000 videos focused primarily on literacy, math, sciences. 400 courses. What we want to be able to do with that information is we want to be able to take that, curate it, and organize it. There’s a lot of information all over the web today. There’s tons of information just on What we want to be able to do with that is curate it accordingly so that it can be utilized from a few different personas.

One, the teacher.

Another, the learner, and that learner could be a student, it could be an individual changing career path.

And then also we want to think about from a data perspective. So that data persona could be a district, it could be a state.

As we take content and curate the content, we need to be able to organize that content in a sensible way to be able to provide delivery of the content in the most appropriate format.

We want to be able to overcome the technical challenges that Shmoop has historically faced in order to deliver content more effectively to the market.

One of the challenges I think we’ve had over time is product development.

We have brilliant content, but we need to improve the way that we deliver that content through our product. That’s one of the big challenges that we started to take a look and overcome. And that was one of the big value points of me coming into Shmoop; understanding how to do that and understanding how to make that content digestible, which is an important challenge. We faced the same challenge when I was at Pluralsight.

“We have brilliant content, but we need to improve the way that we deliver that content through our product.”

When you came into Pluralsight’s platform six, seven years ago, in order to find something you had to hit “Ctrl” + “F”. You hit “Ctrl” + “F” on your keyboard and you would type in what course you were looking for and you were only able to search by word.

Same kind of challenge here; we have a much better platform, but we want to improve the way a teacher can curate the content on their own. So drag and drop courses into a format of being able to put that into a curriculum, take assessments, and utilize them in a classroom. And this is a challenge that schools are facing more and more.

There’s a school in Utah that has integrated online curriculum. They still have teachers in the classroom that are teaching, but the amount of online content that they provide in the classroom is much higher than what they are using from a textbook, for example.

The challenges have been in those classrooms at that school; the school has found itself really challenged to be able to help the learners actually digest content because they haven’t mastered the ability of doing so. The reality is, a lot of students actually left that school and went to other schools because they were challenged.

The way that learners learn is not the same. We don’t all learn the same, and you can’t overly box in how somebody digests content. There are six, seven, eight different types of learners and you have to be able to really morph your strategy to meet each one of those learner’s needs. We’re thinking about those things in depth and how we actually formulate our product for the future. Not just early this next year, but also five, ten years down the road.

Victor: Okay. So I can go to and there is also Shmoop specifically for schools—looks like a few things going on. Will this be radically overhauled, or just tweaked? Will there be a “Shmoop 3.0”?

Andy: Yeah, I’d say it’s going to be radically overhauled. It’s going to be kind of a Shmoop 3.0 version of what we’ve provided. We’ve done a brilliant job with the content that we’ve created up to this point. I think we could do a much better job with how we deliver the content through our product.

That becomes really important to me—our learners, in order to effectively gain progress in any of the topics—that we would be providing to our learners—that would be a big point.

Victor: Back to some really broad general questions here. What is the state of education today?

Andy: I’ve always felt like, I think there’s certain—it’s a tough one to answer. Because in certain ways, education is very progressive. Meaning, they’re kind of ahead of the curve in how they think about their learners. If you think about it from a teacher perspective, I think teachers are progressive. They care. They want to do better for their students. They want to see their students succeed. Every teacher that I’ve ever had for my own children has been progressive. You know? And, that’s really positive. The process though, the states and schools and districts that they work in are not as progressive.

Now, that’s not in all cases. I don’t see that universally.

I’ve seen certain districts really thinking about their learners five, 10 years out, and thinking about how they can be more progressive. But there’s still a process behind it. They’re still controlled in a certain way and influenced in a certain way. And we feel like they could probably be much more progressive.

And so, if we can get the tool in the hands of those schools and districts, we can allow the teachers to spread their wings, so that they have aspects of learning engagement of tomorrow, even with our current product today, to be able to facilitate more progressive styles and aspects of learning for the students.

Education has a way to go. If you look at the overall process and the system of education, I think they have a long way to go. At the same time, if you look at all of the individuals within that process and the institutions, those people are probably more progressive. And, they’re hungry for things that Shmoop is offering.

Victor: ‘Progressive’ is really a loaded word, it’s also a word that’s had different meanings over the decades, if you think of Dewey, or current political intonations. So, let’s explore that word a little bit, get a little bit more clarity on that.

I’m hearing—correct me if I’m wrong—you want to get out of a ‘river of molasses’ status quo stuff, unworkable status quo—and you want to move it so that a person isn’t slow-motion ‘running’ in the river, but they’ve been freed to really run in the direction of learning that works. Is that a halfway decent characterization?

Andy: That’s exactly right. And the fact that, with every learner learning in a different way, sometimes you have to customize solutions to the learner’s needs. My son has had additional needs in school so this is where we needed an additional helper. He needed to learn in maybe a different way or needed to step back six months and maybe teach him some of the things that he’s missed and if you can customize some of that learning in the classroom from a recovery standpoint, from an assessment standpoint, you can really get miles ahead by helping that learner progress and the teachers need that flexibility and freedom to do so.

Victor: We just ran a piece with an academic specialist who was talking about what adaptive learning really means. One point she made was that really good adaptive learning allows a child, a student, or any learner—to be able to have the choice of how they want to learn something.

Andy: That’s exactly right. The concept of adaptive learning and the fact that you’re adapting to a specific student’s skillsets—I think people generalize the term so much and I don’t use it as often, but the concept of being able to say, “Hey, this person knows A, B and C that we learned in the classroom this year, but they didn’t learn E and F and they also didn’t learn Z, to be able to customize solutions, to be able to bring them up to speed. A teacher can’t stop teaching what they teach in the classroom today, they have to just keep moving forward because you’re moving with the flow. And I know it’s frustrating to teachers today that they can’t stop. If they stop, then they have to do it either after hours, but if they have technology that can help that student while the curriculum continues to progress—this is where a teacher really has that need to be “progressive”—but the system, or the flow of how they operate doesn’t allow them to do so.

Victor: What is technology’s role in education?

Andy:  It’s not a replacement for a teacher. Our content and our platform is most effectively provided to the student by a teacher or integrated into a curriculum by a teacher, or to a parent that wants their students to be improving ACT or SAT scores or prepare more for an AP exam. And so, the delivery of the content; we want the content to be able to be delivered independently, meaning: somebody goes into the platform, they pick an area that they want to improve on.

But we also want to be able to utilize technology and we see the use of technology side-by-side with the teacher.

The concept isn’t that we’re replacing a current process or current individual, but what we’re trying to do is enhance people’s ability, the learner’s ability to progress in their knowledge much faster than they would have any other way.

“The concept isn’t that we’re replacing a current process or current individual, but what we’re trying to do is enhance people’s ability, the learner’s ability to progress in their knowledge much faster than they would have any other way.”

And we feel like technology is just part of what we do just like you pick up your phone in the morning, whereas, if you think years ago when you wanted to get somewhere in Los Angeles you’ve got to get you a pull out your Tommy Guide and you had to go through the process. It took much longer to get from point A to point B with that Tommy Guide than it does with maps on your phone. It’s a lot easier if you can just integrate technology into the classroom to gain the progress and we’re really making the world 10 times, 20 times smarter than yesterday’s generations by doing so.

Victor: I know what you mean; just finished some spring cleaning and had my hands on a couple very large, oversized Rand McNally atlas printed roadmaps, the kind that give you squares of city streets in say New England, Boston area, I thumbed through and looked wistfully at them and then I tossed them. I thought about keeping them, but they don’t serve any purpose now except as possibly relics or artifacts, so yeah, I tossed them.

Andy:  [laughs] Yeah, I mean—now you use your phone and when you’re driving down the street, if there’s an accident, or there’s traffic ahead, it will tell you to go a different direction. We want our tools to do the same thing for our students, for our learners. If there’s something that we start noticing through giving them an assessment as they’re going into this learning journey, we might want to redirect them. So, those warnings and those kinds of signals can be given to a teacher and vice versa. The teacher starts noticing something they can point the student in a different direction with the technology. And so we feel like it just needs to go hand in hand.

Victor: You’ve worked with a lot of serious companies, with a serious number of employees with some serious funding and revenue. Shmoop, they might be seriously fun—and I’m not saying they’re unserious—but they’re quite a bit smaller. What’s your vision for the next few years with Shmoop 3.0 or whatever iteration you might want to call it—are you going to bring on lots of employees? Increase the revenue stream? Make it more of a corporation? How’s that going to roll?

Andy: We don’t want to become a corporation quite yet, but we want to grow and we are hiring employees, and we are investing heavily in our future. The reason that we’re doing so is so we can drive additional revenue into Shmoop. We can use that money to invest further in our product and really create a much better platform, and even better content as we progress towards the future.

That same question was asked to me when I moved from Autodesk to go start Pluralsight Creative, as to working there; Pluralsight was close to the same revenue that Shmoop was when I started, and the concept of us growing it, investing in it is definitely something that we’re doing moving forward.

Victor: There’s quite a story there with Pluralsight—I mean, it’s not small anymore.

Andy: No, and I still look at it and I still think it is small—just because, the amount of opportunity. When I look at the opportunity space in the edtech arena, or really, in education, that market—it follows maybe a five, 10-year trend of where that investment goes. There’s a lot of investment that has started to be made in the space, but we have a long runway ahead of us as far as how technology is used in the classroom, and how investment will be made in the future generations of tomorrow. One is through government, through entities of the school system, but as things continue to progress and people continued to utilize technology, the way people learn is changing. And Shmoop is going to lead the forefront of that effort as we progress forward. So yes, we definitely are looking at growth that way.

Victor: There are a lot of other founders, really innovative people working in edtech. Any words of wisdom for them from what you’ve already learned?

Eddie: Yes. The reality is, when people are building businesses there are always a couple of different avenues that individuals can take. We can look at this as all these different education companies are moving into this space, you can look at it as a very competitive arena, who’s first to win in this space or who continues to move forward? I really feel like, through my career at Autodesk and even Pluralsight—was, one of the concepts of us all working together to progressively create the future rather than looking at companies and in each other as competitors; [but] looking at us as a unified go-forward, let’s go create the best innovative technology for tomorrow’s generation. That’s what has always driven success for me at different companies.

When I was an Autodesk I worked with some of the biggest competitors that we ever had. And sometimes there is just borderline hatred towards those other competitors. But when you put those things aside and you sit down and think about how the technology can integrate together, how the tools can actually formulate, then you end up with a real powerful go-forward motion—and everybody ends up succeeding as a result of working together and progressing together in the process.

“…you end up with a real powerful go-forward motion—and everybody ends up succeeding as a result of working together and progressing together in the process.”

So, there’s a lot to be learned for all of us in how we utilize technology to push our own kids forward, to provide them the skill sets they need for tomorrow.

Technology is a part of everything that everybody does in the workplace. However, our students are still utilizing a textbook and so there’s a lot of progress that we need to make together there.

Victor: Well put. Reminds me of Red Sox vs. Yankees fans, but everybody loves baseball.

Andy:  Exactly. Everybody loves baseball and everyone gets to the stadium together and when the World Series happens everyone comes together for one of the two teams.

Victor: Any other message you’d like to communicate regarding Shmoop in 2020 and beyond—anything else you’d like to add or emphasize that we haven’t really touched upon including emerging technologies?

Andy: Just couple of last words. In the future, we want Shmoop to be in every classroom. We want it to be in every parent’s hands for their children. I want anyone who needs to build skill sets for tomorrow and is preparing for possibly entering a new field to be able to use Shmoop. We would like to see the reach of the tool broadened much further than it is today.

We really feel like we’re changing the future of learning—and Shmoop will lead the industry in delivering the most engaging content and the most effective tools for delivering the content. And we’re really excited about our future. We’re busy creating it as we speak.

Victor: All this, just excellent. And, by the way—this your first stint as a CEO?

Andy:  It is yes, my first stint as a CEO. My last role, I was the CEO of Pluralsight creative LLC, but it was still wholly owned by Pluralsight and we still operated with in the walls. So we had our own finance, marketing sales, content, and product teams—I ran that for about two years but really referred to myself as a General Manager of that portion of the business. That was a good stepping stone moving into my first official role as a CEO; that’s the history there.

Victor: Well, this is really exciting, I’m excited for you. Best wishes and we’ll be following your work, Shmoop’s work, and how it all goes. And I am sure that you’re going to make it go very well! Thank you for your time today.

Andy:  Awesome! Thank you so much. It was a pleasure to meet you—hope you have a great rest of the day!

Victor Rivero is the Editor-in-Chief of EdTech Digest. Write to:


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