After Shark Tank: Unpacking Packback

Running off resilience, backed by a billionaire, a rising-star edtech company finds its way.

INTERVIEW | by Victor Rivero

CREDIT Crains Chicago Business screenshot.pngThe stories that are rarely ever told are the ones of grit, failure, hard work, and perseverance leading to success,” says Kasey Gandham, co-founder of Packback, a Mark Cuban-backed edtech company launched in 2014.

Kasey, who with co-founder Mike Shannon appeared on Shark Tank back in March 2014 and was subsequently featured in EdTech Digest, says that the company exists “to awaken the fearless, relentless curiosity inside every student.”

When a student is highly curious about what they’re learning, it also means they’re intrinsically motivated to succeed.

The same could be said for the co-founder himself, who describes in detail what it took to rise above the challenges and make a way forward despite obstacles.

“We believe all students have the potential to change the world when they become lifelong learners,” he says. “Right now, graduation is often treated as the end of education—when graduation should really be the start of a lifetime of learning. Students are taught to answer questions and follow directions, but don’t always learn how to question their world.”

If students are given the opportunity to be “bold, curious and confident enough to start questioning their world, everything changes,” says Kasey.

Empowering students to ask big questions sets them up to go on to become the next great innovators in their fields after graduation, according to Kasey, “whether that means creating a name for themselves in the art world, building up a new business, taking on world hunger, or turning their telescopes to the sky to discover water on Mars—our job is to help wake up students’ fearless curiosity. Where that curiosity leads is entirely up to them.”

Looking back on our first interview, I didn’t ask how it was working with Mark Cuban.

Kasey: He’s a total machine and he’s been really great to work with.

You had something like a million viewers—the most traffic in the history of the show?

Kasey: 8.1 million, yeah.


Kasey: Which, at the time was the most watched. There have been others that have since surpassed that. I graduated college in 2013. We launched around the same time that we aired on Shark Tank, in spring of 2014.

Six months later, we started working on what we do today.

A lot can change in a short time.

A lot can change in a start-up within the first six months of inception and launch, but we always had this hypothesis that once we had students on the digital medium of a book, we could actually be doing so much more to adding value to the actual value of the experience.

The relationship with a user with a textbook is pretty transactional.

We speak to our users every January and August.

The book experience itself was really a PDF replica of a print book. We always believed that, once we had a student on our digital e-reader, could we actually start innovating on the e-reading experience—most notably, by building this second layer of a community where students could engage with each other, and ask and answer questions to each other.

That was the initial hypothesis that led us down the road of what we do today.

Instead of taking this route from books to communities—as we started building these learning communities, we build Artificial Intelligence that looks to quantify difficult-to-measure student success metrics—metrics like critical thinking and curiosity at scale, and a new assessment type for instructors.

Instructors use Packback today as a core part of their grade and a core part of their curriculum, and as a result of that, we improved student engagement.

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We gave instructors the capability to not only assess, but improve, critical thinking skills and higher level learning skills, at scale.

We realized going through that process instead of going from books to communities, we were adding so much value in what we did with communities.

We made the full pivot in 2015 and went all-in in what we do today.

Through that process, I think, what’s been really awesome about Mark [Cuban], just to close the loop on that one, is Mark, he said something along the lines of, “I invest in the Packback team because of their perseverance, which is what’s required to win in education.”

We’ve had a lot of good discussions with him on that. He’s been really, really great and operational for us, even through the pivot—helping us bring us to where we are today.

He’s similar on and off camera, in his advice, I would imagine?

Kasey: Oh, yeah, I would say so. He’s been, he’s pretty straight up. Yeah, definitely.

I know he’s been at ASU/GSV, very involved, has a deep interest in edtech. Regarding AI, is that something he actually brought to the table and said, “You need to pursue this harder,” or were you going down that road anyway?

Kasey: We were going down the road. Mark has a lot of respect for what we decide. He will tell us straight up, like it is. He will tell if he thinks we’re wrong or if he disagrees, but if we go a specific path, he understands and we have a great relationship in that regard, too.

Just like I would expect from any investor and any great employee, frankly, in challenging each other—that’s very much the relationship we have with Mark and that’s what’s been awesome about it.

He certainly has had a big interest in the field. We’ve met up with him at ASU/GSV and he’s been involved in several meetings that we’ve organized with him there in the past, too.

As great as an advisor, mentor and backer can be, they’re not there 100 percent of the time—but you are. You’ve had to hold your own. What advice do you have for edtech startups? Persistence is part of the successful formula, any other key elements?

Kasey: Yeah, totally. Education’s just a hard industry to break into. Most edtech companies actually fail not necessarily because of technology, but because distribution is really, really hard.

It’s very hard to break in and align with multiple stakeholders; the buyers not necessarily being the end users, and everything in between.

It’s challenging. It is its own kind of beast. There is resilience, persistence, and grit required to win in education. Frankly, we’ve had some very dark times as a company. I will not be afraid to talk about that.

There is this perception about start-ups. We read about the big success stories or numbers that go up and to the right, of rapid growth.

There’s always a great story about resilience behind the scenes. If you peel back the onion, those are the more interesting stories.

The reality—and maybe it isn’t articulated that way in the press—but for many start-ups, that is not necessarily the case.

There’s always a great story about resilience behind the scenes. If you peel back the onion, those are the more interesting stories.

In education in particular, we see a lot of that.

That is what’s required to make an impact in education.

The more gratifying part of it is, the work we do is really meaningful.

One of the last things I’ll say to answer your question, which is a great one, is:

You really have to be purpose-driven, because it’s hard work.

The impact is something that’s really special and beautiful.

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In our branding, we like to say, “Packback exists to awaken fearless, relentless curiosity in every college student.”

But interview any one of our team members and ask them why they work with Packback, just informally, they would all tell you, I guarantee, “because there is nothing that I would rather be doing than awakening fearless, relentless curiosity in every college student.”

You’re not just being a tough taskmaster on them—that’s authentic?

Kasey: Right. They wouldn’t go through the grind and education if they didn’t believe it. It is truly hard work. There are a lot of easier things that we could be doing, probably, as entrepreneurs, but the most rewarding, gratifying and impactful things are never easy. That’s my perspective on edtech in general.

I’m curious—you don’t have to advertise the gory details, but you mentioned ‘dark days’ for the company. Were you looking at closing up?

Kasey: We were college students running a startup. You’re probably familiar with companies like Kno and CourseSmart, other e-book suppliers.

Basically, we were trying to do the same thing that companies like Netflix, Spotify, iTunes all had to do in their respective industries in licensing digital content from our content providers.

The difference was, they were multi-million or multi-billion dollar companies. We, at the time, were three broke first-time entrepreneurs and college students.

We didn’t have the luxury of paying movie studios up-front, multi-million dollar guarantees, like Netflix did when the first got started.

We were literally hustling and cold-calling publishing CEOs, VPs—doing whatever we could to license content.

We were actually quite successful in doing so, but that was by all means not easy.

At the same time as raising capital, because it is a capital in business in e-books.

Raising capital through that, licensing the content through that, and then growing the company—and then we pivoted the business six months after the launch.

Well, through all of that, as you can imagine, there were—and each one of those things I mentioned are—seemingly impossible tasks.

You did some record industry independent label type work?

Kasey: This was in high school. I was in a band through high school. We were signed to a kind of big indie record label.

Did a couple of East coast tours and all that.

And then I separately did some work with the label that we were signed to managing some bands, social media, things like that.

But the fun part, impacting what I do today is, as a band, similarly people might have false perceptions of the success of artists.

There are a lot of parallels between starting a business and scrapping together a serious music group for the first time.

We would go out there and play shows to five people in a basement but still make sure that we gave it 110% so each one of those five people would bring two more people the next time around.

[For our band,] we were getting email lists out and doing email marketing before email marketing was a thing.

That taught me a lot of good lessons about entrepreneurship actually and I view it very analogist to playing, making an emotional connection with every single person in the audience and really caring about that, and staying after the set to talk to people.

This is very similar to a lot of what we do today; the service aspect of working with educators, connecting with every single educator, making every connection so emotionally worthwhile.

There are a ton of parallels.

But, yeah. It was a fun experience.

And a fun thing that we do in our office today is—what we found was people that want to work in education are often times highly creative individuals that are very passionate and have a lot of creative passions.

And in startups in general, too.

Unfortunately, a lot of those creative passions are sidelined due to the intensive demands of work.

So we actually host an open mic—an artist showcase.

A lot of our team members perform at it. We do it once a month at our space, which is a pretty fun thing. We just had it yesterday.

Wow, nice!

Kasey: Our co-founders all performed doing different things. My co-founder Mike, he raps. He does free style hip-hop. My co-founder Jessica, she does a lot of poetry. I played in another band yesterday, too. So yeah, it’s fun.

Who would have known? From your LinkedIn profile, I was looking at Hellogoodbye and In Your Arms.

Kasey: Yeah.

And the song’s video was a case of ‘the nerd gets the girl’.

Kasey: That’s funny. Yeah, that was one of the bands that I worked with as a project. But, yeah. That was in high school so that was quite some time ago.

I really admire the way you actually pull together anything from your past, it could be so seemingly unrelated to what you’re doing now, but you take it and make it a part of your intensity and your passion and commitment for what you’re doing right now. Nothing is lost. That’s an entrepreneurial trait, a startup mindset; a valuable thing.

Kasey: Yep. Yep. Totally. And it’s funny in music, in all the parallels, the customer and emotional connection I was talking about, even getting signed to a record label, not too different than in edtech, too; just a lot of funny parallels. Yeah.

What do you think the state of education is today?

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Kasey: Our education system is really one that has the foundations that still exist in strong part today, designed at a time of the industrial revolution and was never really changed much since, unfortunately.

In the Old World, when a lot of these foundations were created, we had to optimize our workforce and our students for a workforce that had fixed, defined roles. Clear inputs and outputs.

As a result of that, it reflected a curriculum based around rogue learning.

Memorization, regurgitation.

Are you familiar with Bloom’s taxonomy?


Kasey: Yeah. So Bloom’s taxonomy, it’s actually the basis for how we built our product and how we, and everything that we do.

But, using Bloom’s is an example.

Remembering—the bottom two levels of Bloom’s are remembering and understanding, basic orders of thinking that we typically might assess through multiple-choice exam or fill-in-the-blank.CREDIT Trinity University.jpg

That was commonplace back then, because it needed to be a curriculum reflecting the world that we lived in.

Unfortunately today, our curriculum hasn’t really changed much.

The majority of education still optimizes for the bottom levels of Bloom’s, remembering and understanding.

And to understand why, but really in a world where in, to solve problems— fundamental problems of the 21st century—we really do need a workforce that is optimized for creative, competitive thinking that are autonomous, self directed, critical thinkers who are highly curious in nature.

These are the traits that people interview for today, right? It’s not something that’s coming. It’s already here.

Are we effectively preparing our students for that?

I don’t necessarily think so.

The reason for that is, I do believe it’s an assessment problem—an assessment challenge.

We tend to teach what we only have the means to measure—and for decades, it’s been bubble tests of scaled, multiple choice, fill-in-the-blank, low-level Bloom’s.

That’s totally scaled.

Especially if you look at a big wave of what I believe the future of education holds.

In all my learning, improving access and affordability for the masses—actually online learning is hamstrung arguably the most, due to this assessment challenge.

This is a very challenging environment from a standpoint of student engagement, but also from assessment; what more can be done?

At the top of Bloom’s, we can climb up the ladder applying, analyzing, and evaluating what we typically otherwise might assess through, like writing, writing an essay, having a thoughtful discussion, doing a case, all of which are assessments that are really hard to scale with consistency.

We look at this issue of these performance metrics, test scores not necessarily equating to learning outcomes, like critical thinking, curiosity, etc.—this issue that we tend to teach only what we have the capability to assess.

You really have to be purpose-driven, because it’s hard work.

When we create standards from the top down, and the people that are in charge of creating the standards from the top down, we tend to cheat a little bit on the standards because these learning outcomes can’t be assessed at scale consistently.

And therein, I think this creates a big trickle-down effective of many of the problems we see in education today.

So, getting to the root problem, I believe that it’s an assessment problem.

I believe we need to create students that have, and are optimized towards focus on higher-level Bloom’s, because we live in a search-engine culture today and we can outsource fact-finding to Google—but we can’t afford to outsource the student’s critical thinking skills to a search engine.

Sorry. That’s a long monologue there but, yeah.

Excellent, Kasey. I talk to some of the brightest minds in education and technology, some very interesting people over the years. Reminds me, I talked to Alan Kay a long time ago.

Kasey: Cool.

Also, I was going back and forth with some of the people behind a Finnish edtech company you’ll hear more about, CLANED.

An interesting point from both was the idea of fluency, which is right up there at the top of the taxonomy with create.

Kasey: Yep.

If one is able to be fluent—like with a language, but not just language—with anything one might do. If you’re fluent in it, that’s where the fun is, where the ‘zone’ is, where things happen. That’s really life. The lower you go, it’s not so lively.

Kasey: Right.

So it’s interesting to see you address that. This shows the genius of your company, the commitment that you have toward education, and why somebody like a big shark would actually jump on what you’re doing. Having seen it all, they tend to be keener in recognizing value. Their eyes penetrate the surface to see what’s really there—and with your company, there’s quite a bit there. So, very cool talking with you! With that, what do you think technology’s role in education is or should be?

Kasey: Yeah, totally. So, it’s a great follow up because, so here’s what’s interesting.

A lot of what I’m talking about you’ve probably heard from, it’s by all means not something, these aren’t original, unique, groundbreaking, ideas. These are things that have been talked about for centuries, actually.

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Back to Aristotle, to Martin Luther King, to Henry David Thoreau and a lot of the other folks that you’ve been referencing.

The challenge, again going back to education, is two things:

One, from a technology standpoint, it’s been really easy.

It’s been too easy to create technology that optimizes for remembering and understanding and it’s been easy to make a quick buck around that, just of optimizing towards helping students better memorize or regurgitate information kind of embedding into the existing culture that already exists.

There’s technology reinforcing a lot of that.

When actually, it should be actually scaling the higher-level orders of thinking on Bloom’s.

There’s no doubt about it, everyone can agree; with the future of education, how technology impacts it is, you know technology’s capability to now personalize the learning experience for students and adapt to the needs of learners.

You’ve probably heard of adaptive technology for, I don’t know, more than 10 years now.

The question that not many people ask though, is what type of learning are we personalizing?

And that’s the unfortunate part.

We get caught up in the hype of personalized learning or adaptive learning.

But when we break it down into, “What type of learning are we personalizing?”—then a lot of the stuff that I see out there in the market today is reinforcing or personalizing a learning experience to lower-level Bloom’s.

I don’t think that is in itself a huge issue.

But reinforcing the fact that there is a huge need and necessity for higher-level Bloom’s and doing that, whether it’s in a non-scalable way just through focus of curriculum.

And [such a] culture needs to exist in academia or through a scalable way, through technology—which is what we hope to focus on.

Okay, good. Now let’s talk a little bit about your features. You have your books and your questions. How are you addressing some of what we’ve been discussing?

Kasey: Definitely. So we don’t do anything with books anymore. They are not a core part of who we are and what our value proposition is.

In reference to the whole discussion we’ve been having about the state of education—what we’ve essentially done is created a new assessment type that does scale into higher-level Bloom’s. And this is a fundamentally different way of how people are assessed.

Our technology—what we’ve essentially been building—is the capability of analyzing a student’s written questions and essay answers.

We can really create insight and a window into their mind.

Basically by propelling students into higher orders of Bloom’s through our curriculum of what they’re focusing discussion around, we get a really great window and insight into their mind by analyzing their written questions and answer essay responses.

We then apply that core technology of understanding where a student is on their critical thinking and curiosity and where they could be.

We apply that then to driving really great, sophisticated discussion. Truly rigorous academic discourse as we like to say.

As a result of that, our AI that backs our discussion, looks to basically serve and emulate a digital TA, a digital teaching assistant if you will.

So we do all the quality control in moderation to guide a great discussion.

We coach students in real time, so instead of students getting feedback after the fact when they hand in an assignment, we give them feedback in real time as they’re writing.

Lastly, we optimize visibility of content on the platform to maximize engagement—very similar to how Facebook would think about optimizing a newsfeed in order to improve engagement.

We think about solving a lot of those same problems and how we model better behaviors from students by surrounding them with content that can actually influence them and impact them in a meaningful way.

Through all of this, between the moderation, quality control, the engagement that we drive, the feedback that we deliver to students through a lot of coaching, whether it’s via email or in the platform itself as they’re typing—the last piece of what we, what it ultimately does is, again, we grade the students, too.

And we do all that at scale for the instructor.

We’re curriculum agnostic, so we do every subject except for math and engineering right now. Math and engineering is very focused on right and wrong answers, whereas, Packback is not about right and wrong answers by any means.

It’s about academic discourse and, in fact, in many regards we encourage students and our professors encourage their students, to take risks and use Packback as a safe place to explore the depths of their intellectual curiosity.

So it is by all means not about right and wrong answers or about extra help. It’s about actual discourse—which we ultimately use to assess and encourage critical thinking.

What’s the cost?

Kasey: Students pay an $18 per-course, per-term subscription.

So very similar to that of a bio lab or textbook, but what we also see is a lot of instructors that have either replace their textbooks with Packback or other course materials.

We’ve seen the movement of open source books being far more prevalent, too.

So yes, it’s a subscription for the students.

Why not, say, $100? Where’d you come up with that number?

Kasey: You mean what was, how did we come to 18? Is that your question?


Kasey: We’re conscious about the cost and affordability and the value that we bring. That was the price point that we felt very confident in. And one thing that we do really rigorously here is we drive a lot, so our retention is really good right now. That’s why we’re growing.

That’s why we doubled our user base since the last term. Professors are not only retaining but they’re referring as well. Typically, what happens is one professor sees great success in a department and then it spreads.

And pretty quickly, organically after that.

That wouldn’t happen without student success.

Our retention is very driven by the student success demonstrated learning outcomes and how students feel about it.

There are a lot of learning products out there that reinforce memorization and regurgitation.

And it might be okay if students feel negative about that, but it’s just part of the course work, it’s part of the textbook, it’s something that’s been expected for some time.

Experience with Packback is very different.

It’s very new.

It definitely pushes students in their comfort zone.

It’s actually, it’s work that they have to do, but it’s work that they enjoy doing—and that’s what success and the platform actually is all about.

We are shifting a student.

When a student is highly curious about what they’re learning, it also means they’re intrinsically motivated to succeed, as opposed to extrinsically motivated.

We actually show that intrinsic motivation in our data.

This relates back to your question on price.

We hold ourselves on pretty high standards on, at promoter score surveys and what we viewed in a space was unfortunately a lot of trends in education around people that, I think you mentioned this firsthand before.

But yeah, it’s, we’re creating technology that buyers, the buyer’s not necessarily the core end user — and we’ve seen a lot of tech out there that maybe optimizes just for the professor, optimizes just for the university administrator—but we wanted to create, we knew that the success of our product around critical thinking and intrinsic motivation is predicated on a student actually feeling really good about it.

So, that price point is reflective of that and the value that we know we can deliver today.

However, we have a lot of vision for what we know we can do moving forward and that, in the future, if we did ever change price, which I’m sure we may at some point in time, we would do it if we felt very confident in the value that we were delivering at that price point driven by a lot of data around that promoter score and etc.

So that’s our perspective on price and what it means to us. It’s directly related to impact.

Anything else you’d like to discuss, issues or areas that you feel strongly about?

Kasey: Yes. We are excited about working with University Ventures more closely. And the only other thing I’ll leave with is that we appreciate education, as it is a world unto itself, and there is a lot of shared learning required in order to navigate it at a quick speed.

One last question: AI will play a “huge role in the future of education” says Mark Cuban. The future of education is developing “independent and critical thinkers,” he says. And he invested in the Packback team because of “their resilience and relentless focus on student success outcomes – this is what it takes to win in education” So, what’s your take on AI in education—we talked about adaptive learning—do you have some future forward thoughts that you’d like to share to round this out?

Kasey: Yes. I think we’ll be able to create a lot of, anything is possible in terms of what can be, there’s a lot of interesting things that we can create from a standpoint of technology out there in the market.

What’s been beautiful about the work that we do is we have the amazing opportunity to work with educators that are really at the forefront of driving innovation and change.

Consistent to what I had mentioned to you, today, with a lot of the mainstream­—I’ll call it “adaptive technology”—centers around, I take a multiple choice assessment, I get the answer wrong, I jump to a chapter of the book where I can read the right answer—and then back to my assessment and I fill out the correct response.

And it is adaptive, but it’s adapting to lower level Bloom’s.

And I think that change, that the catalyst for change really comes from technology companies showing what’s possible, which is what I hope we do, but also really from an educator’s standpoint, I think what’s been beautiful about the work that we do is we have the amazing opportunity to work with educators that are really at the forefront of driving innovation and change.

I do believe that the change happens from the bottom up in education, and that it needs to.

Instructors are really driving forward a lot of this.

In terms of what technology will be able to do, the verticalization of AI is something that’s really fascinating on helping take hyper-specific approach; demonstrations and utilization of AI to make for really great outcomes, in our case, education.

That’s really fascinating to me.

And I’m really excited to see more applications of very specific utilizations of that in specific verticals.

The other really exciting thing for us to see, especially in education, is human-assisted AI.

And we’re not, we’re by all means not replacing an instructor—but we are making them 50 times more impactful and more effective, and we are enabling them to personalize the learning experience at higher levels of Bloom’s.

So that trend is really fascinating to us as well.

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As technology and as this change from the bottom up, really does happen—the shift is about changing the focus on how students should fundamentally be assessed, that is, what does success actually look like now that we actually can measure a learning outcome, as opposed to a performance metric?

This aligns the hiring industry and the recruiting workforce, recruiting initiatives for the workplace with education—one of the biggest gaps that exist today.

There’s a lot of HR tech and tools out there that talk about ‘personality assessments’ and different things like that.

If education could be directly aligned with the workforce as opposed to being indirectly aligned as it is today, we would see monumental change in both industries.

And in thinking about that question of how should people fundamentally be assessed in education?—that is something that we’re excited about in the future.

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


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