North Star Leaders Podcast

Lindsay Pedersen

The world needs what only your business can bring. And as a leader, it's your job to deliver. But where do you focus?

Where do you direct your time, your team, your budget, and your emotional energy? We're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that they make to create audacious economic value while also realizing their distinctive purpose.

I'm Lindsay Pedersen, brand strategist, author of Forging an Ironclad Brand, and host of the North Star Leaders Podcast. Let's get to it. Today, I am really happy to be joined by Andrew Grauer, CEO of Learneo.

Learneo is a platform for learning and productivity, including brands you know like CliffsNotes, Course Hero, and QuillBot, among others. Andrew, welcome to the show.

Andrew Grauer

Thanks for having me, Lindsay.

Lindsay Pedersen

So good to have you. To start us off, Andrew, what is the most energizing part of your job that others would never guess from the outside?

Andrew Grauer

I think being able to see how fast our team is being able to discuss an idea now and actually not just determine what the product requirements are going to be, but actually be able to visualize it, get a mock-up, get a prototype and ship it. Like the iteration cycle now is just wild. And so I think just like cutting down on the time of, hey, what can we do to actually shipping it to production is just like, that's that entrepreneurial energy that is just amazing to be close to.

Lindsay Pedersen

I love that. It's like a shot of oxygen. Like you just immediately get feedback.

You immediately get to see the fruits of your labor.

Andrew Grauer

Yeah, that zero to one feeling is always just, you know, so powerful you can't get when you start to get into optimization mode and it's more incremental. You got to be careful because, you know, you need to be able to optimize and go deep and just be talking to customers and making those improvements. That's where like the real magic is and the real differentiation.

But it is amazing now what's happening in terms of just the speed of going from idea to prototype in production.

Lindsay Pedersen

Is there an example of that you can share or is all this super secret right now?

Andrew Grauer

No, we're actually launching this just live, like literally day by day, week by week, month by month right now, especially at Quillbot. We've been launching all new feature sets, like moving from our writing tools, which is like generally in the paraphrasing grammar checking space to now we had a total of about eight tools at the beginning of this year. We've now shipped over 15 new tools into the space of like AI chat, AI search, a bunch of PDF related tools for people who need to convert PDFs to Word, PDF to PowerPoint, PDF to JPEG, a lot of image generation tools.

We've already got our new image generator tools out in production. We've never been in the space beyond text to text transformations in Quillbot. And so we've been moving into generative AI, like AI chat, been moving into multimodal communication with speech to text tool, a text to speech tool, and then the visual space here, PDF related tools, visual templates are coming out.

We've got image generation, image editing. And so there's a huge transformation happening right now over the next six to 12 months for us as we move from just being in kind of Quillbot's world of competing with Grammarly to now competing in the world of Canva. And, you know, literally day by day, week by week, month by month, we're literally shipping into this space.

And it's not just in our heads, it's actually getting to production literally in the course of just the last two months, we've just shipped these over 15 meaningfully new tools.

Lindsay Pedersen

Wow, how rewarding. Since we're talking about product development, you have as a huge value for you is empathy, and that you think of empathy as empathy for the student, in particular, and for the educator, as the thing that drives product creation. Can you talk about empathy?

And like, how do you use empathy? And how did you know that empathy was like the key to unlocking what you wanted to unlock?

Andrew Grauer

Empathy is probably highly correlated to understanding people and customers. At the end of the day, maybe the luckiest and most important thing that we got right, and Lindsay, when we worked together on Course Hero, is it's highly related to finding an actual real pain point, a real problem. And if you can empathize with it, it's much more tangible and explorable than doing user research in an academic or intellectual way.

It just shows up different than in metrics, whether it's quantitative or qualitative. I think you can even explore those metrics a lot more. And so, you know, just getting real about it, it's like when we were working together on Course Hero, I'd be like, let me really understand that stress of a student, the anxiety of the student, the context of why is homework or a test or a paper so stressful?

What's causing that? And then you can really explore the solutioning much better. In the world of Quillbot, it's been quite similar, both for students, but since we're also really building for professionals in a huge way, it's nice that I've also been growing up.

I can now empathize as well of what does it mean to be a professional? And what are the different functions across a company and across the economy? Because customers that we serve in the market, and we want to serve better, if you can actually also feel it and empathize with it, I think that's just really, really powerful.

If I don't live it myself, then I think it does take a ton of time to actually go figure out a way to talk to people. But you somehow have to get it much deeper of your understanding than something where you're reading a report, or just doing surveys, or just looking at amplitude dashboards. Otherwise, it's like hard to get the right intuition about what to do with it.

Lindsay Pedersen

This is so powerful. It's like for running a business period, let alone product, all of the aspects, product creation, communicating, pricing, distribution, all of that. But just as a very fundamental activity and mindset to actually just be inside the world of the person you're trying to serve, kind of like customer out rather than an out in.

And I imagine a very noticeable result is that you're not missing the problem, you're actually solving an actual problem. So it's not a square peg round hole. We've got the solution, let's jam it into what's the problem, which is way more efficient in creating the right product to begin with.

Andrew Grauer

I'm curious for you, you have to do this in so many different problem areas, so many different market areas. How do you dive deep into these different markets or customer segments, product solutions, and actually get that intuition to build up from talking to, I know you talked to tens of, if not hundreds of different customers whenever you do an engagement. How do you end up building that pattern recognition and intuition to say, okay, I looked at the data, I look at the results, but the data by itself doesn't tell you what to do.

You still have to put then a hypothesis on top of it. How do you do that?

Lindsay Pedersen

This is a deep question. I didn't know I was going to be asking questions here. Let's see.

I think in a lot of ways, being on the outside alone creates a huge advantage because psychologists call it the curse of knowledge. Like the closer you are to something, the harder it is to imagine not being close to that thing. So the closer you are to a product, then the more that you know about it, the harder it is to imagine not knowing about it.

And since most of the audience is not very close to your product, like it's just one of many, many, many, many things in their lives, having an outsider do it in some ways is like a better proxy than if you're on the inside and you know too much and that gets in your way. I actually think you can work with that though. Like if you're on the inside, just to be aware, like this is like the Buddhist beginner mindset, like I don't know anything.

I am just here and all my humbleness and curiosity to feel what it's like to be this person. And it's an advantage to be on the outside. But if you're on the inside, you can train yourself to think like that.

And it's sort of like you have to put aside how proud you are of your product and go to this person doesn't actually care about your product. They care about what's happening in their life. And by the way, they care about things in their life that have nothing to do with even the domain of your product.

You know, if they might care about their role as a parent more than they care about their role as a student or as an educator or as a professional. And so not really asking questions about your product until the very end and just understanding them kind of like human to human, animal to animal. What's it like?

I mean, that's a trained skill in a lot of ways, but I think anybody can do it. But the rewards are massive because you're actually serving a person. And if you think that way, as opposed to peddling a product, and it just creates more of a energizing feedback loop when you do it that way.

It also so happens that you create better products when you're not focusing on the product, you're focusing on the problem. How did you get me to talk so much? I want to hear from you.

Andrew Grauer

I want my audience to hear I love it because I remember us going through our brand strategy work and the evolution at Coursera from understanding like the functional use cases, but then really understanding the context of, you know, a traditional student, a commuter student, a parent student, a first generation student, and understanding when to be talking about for a brand and a product. What are we doing functionally? What specific pain points are we solving in a given moment?

But then how does it ladder up to like, what's the aspiration? You know, I'm trying to get a minor, a major, I'm trying to get a degree, I'm trying to graduate the most high level. It's not like I'm just trying to graduate a program or a school, but I'm trying to achieve something.

I'm trying to get a promotion in my work that I'm already in as I'm working in school, or I'm trying to get a career. It's some sort of transition more like abstractly, like to graduation of my skills, of my capabilities, or like the next stage of my life. And I've been thinking about that, that work and that process we did as we've been evolving now, building Quillbot for this next transformation and evolution and going from where we've been, just exploded on the scene of how do you innovate on writing refinement and amazing writing tools that had built Quillbot to serving over 30 million people every month to being known.

I mean, right now it's known for how we can help you paraphrase your content, grammar check your content, spell check your content, check for AI content or plagiarism, content authenticity related tools. And it's been actually like super powerful to understand how that can happen in a student context or a professional context. It's been helpful to understand how it's particularly powerful for English, non-English native writers and speakers.

That was something that was not intuitive and it just was something incredibly important to how the product helps with confidence or lack of confidence in communication. And in this area, we've really been going deep over the last few years. And now with just so much advancements, it feels like daily in the world of AI, there's so much more availability of generative AI capabilities.

We realize that there's this huge opportunity for us to serve people with not just writing refinement related capabilities, but to help them not just do text to text transformations, if you will, but go to visual communication and creation. Why are we just helping with text? But we can be helping with fonts.

We can be helping with emojis. We can then be helping with image, voice, visual capabilities, generative capabilities. And how does that speak in the world of somebody's live and association with a brand to move from what we've been known for to then expand the capabilities in what seemed like a natural order to us and through our conversations with people, with users, but then to build that brand authority, to build that brand association.

And what does it stand for functionally? What does it stand for aspirationally to help people be able to not just write, but communicate not just write to think better and think to be able to write better. But we see this association with thinking and creating in all sorts of formats.

And so we were super excited about this transformation, but it's going to be an evolution. And I've been thinking about our work and our framework that we did in terms of how do you break down the functional versus the aspirational and what's the right bridge and ways to do that in an authentic way?

Lindsay Pedersen

I love that. There's something, I don't know if it's counterintuitive, but there's this, when people think about meeting the customer or the user at different levels, like sometimes it's very functional, sometimes it's more emotional, sometimes it's very granular and concrete, that a mistake that leaders make is in just staying in one of those, like staying really concrete or staying really aspirational and not kind of traversing those with the customer.

It's like all of those are important depending on the moment for the customer and depending on the customer that it's like this multiple truths. Yes, you're serving them when they're about to take an exam and they need X, Y, Z pain solved. You're also helping them step into their own power in the world by doing this, right?

You're doing something much more, all of those things are operating together. And I think like the mistake, an easy trap is to get stuck in one of those and not to kind of embrace all of those in the way they dynamically affect one another.

Andrew Grauer

Yeah, I think it's a real struggle, as you say, especially if you get deep into it, how do you like keep it simple, stupid, you know, like, how do you see the forest through the trees and just like come up with a simple recipe? And like, the more you get into it, it's like, there's so many different options and different paths. Now, for us, like there's so many, again, like the ability for us to now ship new things that also anybody to ship new things is just game changing.

And in some sense, it's like super exciting. You know, you can take this backlog of priority they want to ship based on insights from talking to customers and what should we build in what order and like just start shipping them at the same time. Then you're thinking about, okay, like out of all of these possibilities, like which one do I do in what order?

And then how do I make sure that I'm building with craftsmen like love to still have like great quality product. There's this tension between like, first and foremost, like how much to go deep in terms of like, we've gone so deep into building amazing grammar checking, amazing world leading paraphrasing. We've also led the charge in terms of multilingual capabilities based on the insights that we can really help multilingual users, multilingual people.

And that's like, we've generally gone so deep there. And then now we can go and add so many more functionalities and generative AI and multimodal capabilities. Then we have this tension as you go more horizontal, like do we balance between going wider and continuing to just go deep and build products that people love at the same time as being this place where we can do so much for people.

I think that's a really interesting problem space to engage and have tension with on literally a, you know, a week by week basis.

Lindsay Pedersen

You're pointing to something. It's interesting that at the same time as these tools become just wildly powerful and compelling and fast, something that remains is the need for a leader to prioritize. Even if you're prioritizing every day instead of every year, you still have to, well actually tell me if what I'm saying is true.

Do you still have to prioritize even in the age of infinite gen capabilities? It seems like you still have to prioritize.

Andrew Grauer

Oh, critically you do. And the question is like, through what dimensions are you prioritizing still? But critically, you absolutely do.

I think that's probably one of the most important parts of any leadership role. Anybody who owns some sort of roadmap where it's associated with like people working on it, resources allocated to building things. From my perspective, the number one job and skill is prioritization.

Lindsay Pedersen

Wow. What are the constraints or guideposts that you have for prioritizing as the CEO of Learneo and as the CEO of Quillbot? What are the things that you look to?

Yes, we're inbounds. No, we've gone too far.

Andrew Grauer

First conceptually, I love maybe keeping it a framework that is independent of a topic area. And in that sense, I think a prioritization framework can be if I'm going to work on a given initiative or a given investment, these are just synonyms. I'm going to work on something and I'm going to allocate resources, time, capital, people.

I need to consider the following. If I work on this, what period of time am I looking at? Like what's the time horizon for this particular investment?

In that investment, if I work on it, what's the chance of it being a success? And I think that's an important kind of binary question to ask oneself. If I work on this, will it be a success?

Will it not be a success? With what probability? Two, if it is a success, what's the magnitude of the win?

What's the magnitude of the success? And I think if you're multiplying those two together, that's why you're either implicitly and hopefully explicitly investing in that area. And then I think you're then looking at the cost of that investment, like the opportunity cost of doing this versus like the million other things that I could be doing.

And what's the one, two, three things I'm doing? And what is the sum total cost of that? The time, the energy, the capital, the cash capital, the human capital.

And I think that's the one, two, three framework. There's other necessary conditions to consider. I've got my brand.

And if there's any brand constraints that I have, any necessary conditions that I need to maintain or improve upon, that's another constraint. But those are the four in general, whether it's at the company level, at a business level, at a product line level, any particular roadmap, whether it's in product design, engineering, AI, it's these four. If I work on it, what's the probability of success over a given time horizon?

If it is a success, what's the win? Because they have different risk reward ratios. What's the cost of that over that period of time and any necessary conditions to hold constant or improve?

And in general, I think that the internet is a beautiful place to make bets where you've got enough excess capacity to be taking swings at investments that have the chance of being a hundred X win, a thousand X win. In addition to saying, I'm going to have higher probability singles and that I'm racking up. But if you make enough of those and you can take riskier swings that the higher chance of failure, but if it does work, you've got a symmetric upside.

I think that's a nice thing to be allocating against in your portfolio of investments. So that's generally maybe as a framework that I think is more helpful for thinking through kind of anybody who's in charge of a roadmap or people working on something. I think that's a nice framework in my mind.

Lindsay Pedersen

Yeah, I love it. What do you do as a leader or what do you do as a person to refuel when you're not working? How do you make sure that you have the best brain when you are working?

Andrew Grauer

I mean, that, first of all, is an ongoing challenge to engage with. I think it's super important from a whole host of perspectives. I think one of the ways I come at that is I don't want to burn out.

I think being engaged and loving one's work and being able to do it over a long period of time and compound the results of that is impactful. And there's actually my year 19 building, PoolBot and Learneo and Courserao and the rest of the Learneo platform. And I think having that framework, how do I practice that?

Because there's lots of different stages of life and taking the time to understand oneself and what do I really care about and how do I make that happen? What goes through my mind? I think first and foremost, maybe I do need to think about my own health.

So I think when I'm doing my best, I'm thinking about things like get eight hours of sleep, please.

Lindsay Pedersen

Yeah, basics. Yeah.

Andrew Grauer

Truly basics, like making sure, like thinking about sleep, thinking about what I eat, getting time to walk. If I'm doing better, I'm this year, actually for the first time in my life, doing actual weight training. I'd never really done that before.

Doing, I mean, I'd call it, I wish it was walking and running intervals, but it's more like call it jogging and walking intervals at this time so far. So I think personal kind of health, what I'm eating, that's the shape of that. And then next most, just thinking about my wife and our relationship and then my family and closest, you know, and kids, my nuclear family.

And like, that's what means the most to me. But I start with health because I need to, I need to be healthy myself to be able to engage the world and understand what I want and actually even serve others. Like that combo, I think being selfish about, I got to be healthy is still the first place I start then family and then work.

And then probably broadens from there, you know, whether it's friends and community. But I think about it when I'm doing my best thinking in a structured way, hierarchically like that, or concentric circles like that. And so then, you know, enough times I'm grateful for remote work in the sense that I get to be home and closer to family, especially since my kids, you know, are five and a half and three and a half and 20 months.

So like, I love that sort of opportunity. Our business is actually remote and distributed. And so I love the benefits that come with that in terms of being able to be more, think about my own health, my family, and then how I can do my best work in an integrated way.

I feel super thankful for that. Those are some of the thoughts that go through my mind in terms of how can I actually do my best work or accomplish what I want over a long period of time is thinking through those different areas.

Lindsay Pedersen

Introspection and again, prioritization, being aware of your own body and your immediate needs, your family's needs, what's making them flourish and prioritizing, just good old fashion prioritizing. It sounds like, yeah, this is a big theme of this whole conversation, actually.

Andrew Grauer

Yeah. And it's a practice and it changes over time, right? So I think like figuring out when to revisit that and what are changes that I need to make.

But I think that's kind of critical for any of us to take time to do that. But I also find that like overthinking and just is actually problematic. And just like acting is like so much better for my stress levels.

And like when I'm feeling like I'm actually making progress is don't overthink.

Lindsay Pedersen

Stop thinking and just do like, let there be a room for decisive. Just go.

Andrew Grauer

Yeah, I think so. At least for myself, I found that having more of a bias for action, taking more action mentally and physically makes a difference for me. And I think engaging much more, even though everybody said it, I personally couldn't like truly connect with like, love the process, enjoy the process.

I'm very much trying to engage the present and the feelings and don't be fearful or defensive about the feelings, rather like try to lean into them as opposed to being like, really connecting the dots between inputs and outputs and outcomes and saying like, this is what we have to do probabilistically to achieve these outcomes by this point in time. That's not wrong, but I love the idea of what is more of the craftsman like approach to doing the best we can in any situation, but like from a place of like liking that process, whether it's good, bad, or really ugly is something I'm practicing.

Lindsay Pedersen

I love that. That's such a subtle but powerful point of not resisting the things that come up, the feelings being there as you're building. Oh my gosh, what a mind blowing conversation.

Thank you so much for all of us. I have some rapid fire, like one word type questions as we finish. Are you ready for that?

Andrew Grauer

Let's do it.

Lindsay Pedersen

Okay. What is a favorite guilty pleasure TV show or movie?

Andrew Grauer

The latest one, myself and my family had just gotten obsessed with K-pop Demon Hunters. Love.

Lindsay Pedersen

Okay. If you did not live in the United States, in what country would you want to live?

Andrew Grauer

I mean, I love the lifestyle of Italy. I do too.

Lindsay Pedersen

Okay.

Andrew Grauer

I was just hearing from a number of my teammates that there's a place in Italy. They said like, this is the best combination of lifestyle, food, cost of living, just everything where people would want to retire. And there is some consensus, which I was surprised by them.

My teammates live in Germany and the Netherlands, and they say, it's in Italy. And it's south of the Dolomites, north of Venice, east of Lake Como, anywhere in that area of Italy.

Lindsay Pedersen

Like Verona, Bolzano. This is, I'm no longer in rapid fire territory, but I really want to know. I've got Italy on the brain.

Andrew Grauer

All you have to do is just pull up the map. I'll just look at the map. Look at that area of the map.

Lindsay Pedersen

Just go there.

Andrew Grauer

Just look at there.

Lindsay Pedersen

Just drive there. Okay. What is your favorite salty snack?

Andrew Grauer

Probably right now, bacon. Awesome.

Lindsay Pedersen

Love that. Okay. What's your favorite way to spend the Monday of a three-day weekend?

Andrew Grauer

I would love it if I had time to do some sort of activity, whether that was, right now, probably pickleball or squash. Get the heart rate up. It seems like somehow my heart rate just gets up to like 170 to 185, which is, I don't know, seems like super high for such a low-intensity sport, relatively speaking.

But yeah, I would love to get that activity in. Would love to not feel stressed about the next date so much that I had time to like go to the pool with the kids. Our kids just like will stand literally 10 hours straight in the pool.

I don't know what it is. A kiddie pool, a real pool, the beach, like whatever it was.

Lindsay Pedersen

Water. I don't know.

Andrew Grauer

It just blows my brain how much that can keep them entertained for literally infinite time.

Lindsay Pedersen

And then they're tired, so they nap or they sleep hard.

Andrew Grauer

Yeah. And then, you know, probably have a review and destructure for like, what do I need to accomplish the next day and the week?

Lindsay Pedersen

Yeah. The vitamins, too. Okay.

And last but not least, what was your last splurge purchase?

Andrew Grauer

Okay. My favorite last splurge purchase is a wagon bike. You look up like a bunch bike, best purchase post-COVID.

It has like a bucket in the front. I feel like you could see these in like the Netherlands.

Lindsay Pedersen

Yeah.

Andrew Grauer

It's a motorized bicycle, big box in the front, a couple seat benches in there. And, you know, all three kids can get in. We could stuff the dog in.

My wife's even gotten in sometimes, but that's a struggle. So it's usually one, two or three of the kids in there, and we just go around town. And I love it.

Lindsay Pedersen

Oh, my God. That is a fabulous splurge purchase. This has been so great, Andrew.

Thank you for taking the time. If folks want to learn more about you or Learneo or Quilbot, where should we send them?

Andrew Grauer

Check out Quilbot.com and see if we can help you out with any of your writing and now generative and multimodal needs. Feel free to connect with me on LinkedIn. And yeah, thanks.

Lindsay Pedersen

Thank you so much. Thanks for listening to this episode of North Star Leaders. Make sure you don't miss an episode by subscribing on your favorite podcast app.

If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com. Also on that website are show notes, transcripts, and a way to sign up for our monthly newsletter. I hope you join us again for another episode of North Star Leaders.