Startup Savants Podcast: Interview with Co-Founders of Nook

In this episode of the Startup Savants podcast, Marc Gingras and Chadwick Carlson speak with hosts Annaka and Ethan about their adventure in founding Nook, a free calendar app and scheduling tool that holds the promise of helping busy professionals use their time together more efficiently. The entrepreneurial duo opened up about the meandering path to their current product, choosing team members, and much more. 

What’s the basic problem Nook was designed to solve?

Marc: “We were all living in the pandemic. And what ended up happening was we started to see people saying, hey, when should I come into the office, when should I not? And then trying to figure out who was coming in, who was not. And we’re like, this is an actual problem that people are having. And then looking at the space, people are going to say, hey, I probably don’t need as much space for people to come into the office. So we start to say, hey, maybe there’s a market there for telling and trying to figure out when your colleagues are coming in. So we built a solution for that, actually sold it to a few companies. Even the Canadian government started using it, Immigration Canada and stuff.”

So your current product is the one used by the Canadian government?

Marc: “No … as we were building that, we started to figure out that the main problem is actually around coordination, and where coordination happens is around the calendar. So then we said, you know what? Let’s build a really better calendar app for people that work in a remote environment, and that’s where Nook Calendar came to fruition.”

Nook Calendar is your final, finished product, right?

Marc: “Actually, no … as we were building our calendar app … we noticed a much bigger opportunity where people are using so many different applications, and they live with a scattered brain that they’re trying to figure out ‘What’s the important information? What are my to-dos?’ And so we’re actually pivoting yet again because of this bigger opportunity. And this product is still not out, it’s going to be out in the fall, and [we’re] super excited about what we’re working on right now.”

How do you explain changing focus twice in just a year or two of operation?

Chad: “Yeah, it’s been a really interesting journey. And I think the one thing that makes the team special is how eyes-open we are to the opportunities and not being fearful to change direction as needed … I think we’re onto something now. It took maybe a few turns along the road to get there, but this time as the foundation and calendar elements still come into play … I think we’re getting to the root of the problem … this chaos and lack of clarity is a really big thing when you’re either stuck alone in your basement or on Zoom calls all day.” 

What inspired these pivots?

Marc: “It started with us feeling the pain even more. So, as a small [company] we started to see that we were trying to keep track of what we needed to focus on, and what we needed to work [on], and our to-dos, and all that stuff, and everything was spread everywhere. And then as we were getting feedback from users as well, they start to indicate very similar trends, users of our calendar app. So as a small company, you have to go for the stars. And sometimes you have to wonder, ‘Am I climbing up a tree to get to the star, or am I building a rocket?’ And we figured that maybe we were on a plane, but we needed to be on a rocket, and that’s why we decided to pivot towards that.”

How did you get to the point of founding a startup together? And did you both always want to be entrepreneurs?

Chad: “Marc and I have known each other for 20 years. He’s always been a mentor to me … One of the first jobs that I had was at a smaller startup. Marc was there in a leadership role, and I ended up reporting to him … So we worked together for a while … and that startup got acquired. We went our separate ways, always kept in touch … and then over time, eventually the stars aligned again. I was unhappy at a current job at a larger company. Really missed the startup environment, the smaller team, the ‘get things done’ attitude … Marc reached out to me, I saw the posting for the startup that he was at with Foco, really liked what I saw, we connected — happened within a few days — and rejoined each other there in a product management role … [then] we were going through the pandemic, all these new problems started to appear or surface and the entrepreneur in Marc and the product guy in myself saw an opportunity and assembled a really good team of people to join us, and I think that was ultimately what made the moment right. It was timing and people driven by the pandemic, I suppose, but probably would’ve happened anyways based on the type of guy Marc is.”

Presently, many calendar apps are available. What is it about the Nook Calendar that sets it apart?

Marc: “So the calendar app itself, how it’s different is really around how you communicate, and you interact with your close people that you work with the most … You may be working mainly with 10, 15 people at most … how do you make those interactions with these 10, 15 people better? Whether it’s knowing where they’re working from, whether it’s making it easier to schedule meetings with them, whether it’s easier to share your status of what you’re working on. So those are things that I think are rooted in the calendar and that’s what I think makes our calendar app much different. So it’s really focused on the people that you interact with the most. And how do you coordinate stuff with them?

Chad: “That scheduling piece, that’s a really important component, especially when everyone’s remote. It’s easy to meet, but it’s also too easy to meet at times. So everyone’s schedules are really full and complex. So one piece that we did add that we think was a table stakes item now for the calendar, is this whole concept of the scheduling page so that you can publish that to external people. They know when you’re available or able to book your time, see your calendar. And we incorporated that directly into the calendar application as opposed to being a sidecar or an additional subscription service to the calendar, because we think it’s evolved to the point where the calendar needs that by default.”

How do you know when you’ve landed a true product-market fit?

Marc: “To me, it’s all about the metrics. Are people opening the app every single day? Are they using? It’s all the usage metrics that you may want to get. What’s the retention rate and stuff like that? So those are the things that we bank for when we’re looking at product-market fit.”

Are the metrics ones generally applicable to business or are they specific to Nook?

Marc: “So there are the usage metrics — how many times are you using the app, are you booking meetings … and every app will have their own little active metrics that they need to follow. But I think there’s also another metric that people often forget … how naturally is your user base growing without having to invest from a marketing standpoint? And if you’re seeing that there’s word of mouth or there’s some virality component to it, where your user base is growing, your daily active users are growing naturally without you having to invest in marketing, then you’re hitting product market fit. If it’s just staying stable, while staying stable is actually not bad, but if it starts dwindling down without some marketing push or AdWords and so on, then you haven’t necessarily hit your product market fit. So to me, you’ve hit it once you start seeing a natural pull for your user base to start increasing.”

Are pivots inherently painful or is there a way to architect them correctly where they’re either A, not painful, or B, you can get your user base excited to move forward with you?

Chad: “I think the first challenge is actually internally getting over that mental fear of making the decision to do it. That’s a big decision internally considering users, of course, but also the internal mindset, the shift. Takes a lot of consideration, and a lot of thought, and a lot of confidence to do that. And I think that’s really important to make the decision, but also then start to do it very swiftly at least internally. And that’s part of the pivot process I think, is to make up your mind, don’t waver on it because that becomes completely chaos if you start to do all these little second guesses along the way, and that’s a big part of it. And in terms of product, there’s always going to be some fallout from it. What we’re hoping we’re doing though, is we’re actually taking the best of breed from what we’ve learned and transitioning it into the new product. And that’s really what the focus is.

We’ve listened to a lot of users, feedback is key. We know what the majority or the larger pain problem is. And we think that everyone will see that when presented with the solution. And that’s really what we’re trying to do. We know we’re not going to make everyone happy, but we do want to solve a real problem. And I think usability and functionality, but also solving the right problem are important. And I think people naturally understand that. They realize where the value in the solution lies. If it can make their days easier and more efficient and ultimately are accepting of that, even if it means maybe losing a few minor features along the way. 

But something with a calendar is pretty interesting. You have this calendar grid that’s pretty standard de facto. What we want to be is something that lives alongside that. So at the end of the day, if we continue to add supplemental value to the calendar or to your work, that’s really what we’re at. And we believe people see that and the pain point is pretty low … it definitely leads to a better solution for everyone in the long run.”

Pivoting involves sunk costs. How do you justify those wasted resources?

Mark: “So, I’m a strong believer in sunk cost. And sunk cost is you always make the best decision for the future, independent of the investment you made in the past … the point is when you look at companies, and our strategy, and our products, and all that, we always figure out what is the best investment for us for the future. And that’s where pivot comes in. And so, that also allows us to make these transitions super quick. So when you decide, hey, this is probably the best bet for us in the future, you just turn the ship super quick around. We’re not the Titanic, that’s the whole benefit of being a startup. So when you switch it might be painful for some people, but that’s where we believe the future is and you just do it.”

Originally, your company was called ‘Get Working’ — the pivot changed that to Nook. What was it that led you to make the decision to change not only the product offering but the name and essentially everything that went with it?

Chad: “For me, a lot of it was linguistics. Get Working was offered … in Canada, so we have to support both English and French … [Get Working is] obviously a very English name, but also doesn’t really roll off the tongue like Nook does. We find that Nook is very much a memorable name and the branding that came along with it really helped as well…”

Marc: “Yeah. And I had a co-founder in a previous company that believed that if you have a lot of O’s in your name, you’re going to be successful because you think of Facebook and Google and all that stuff. So we figured we’d go down the same frame and call ourselves Nook that had a lot of O’s because Get Working has just one O and it’s not good enough.”

What did the original product do and how did it morph into what you’re doing now?

Marc: “The original product has nothing to do with what we’re doing now. The original product was really about, hey, I’m coming into the office. Let’s say there’s only a hundred spaces that I can come into the office because there’s only a hundred desks. Let me reserve one space, and then if you were at number 101, you couldn’t reserve it anymore. That was Get Working. What we’re working right now is on the problem of dealing with all the information that you have across all of your apps and your to-dos are across everything, and so they need to be centralized. And then we’re also adding context. Anyways, very different problem set, very different users, very different everything just because we believe that there’s a much bigger opportunity there with that one.”

Calendar apps are ubiquitous and are used in a conventional way. How do you encourage Nook to be used in an unfamiliar way as well? 

Marc: “It’s a fine balance. One is you have to understand what is the core that people are looking for and where do you want to innovate. And that’s where you spend your time on the innovation part of it … you’re going to reinvent the entire calendar. And so like I said earlier on, you’ve got the grid, and not much innovation will happen there. Look at it in 20 years, it is going to probably look very similar. But there’s a lot of things around that. What’s the information in the calendar event, can a lot of information be put there, are there more interactions that can be done? Can you share more statuses with colleagues and stuff, collaboration, and things like that? Those are more hidden things where you can innovate quite a bit. But the grid, don’t spend a lot of time because that’s what visually people see and won’t change. So that’s where we decided to strike the balance between the areas of innovation and where you can change things quite a bit, to the areas that you cannot change things.”

Chad: “And I think one way to look at it is there’s the UI component of the user experience, but there’s also the data that lies within, and being able to connect valuable things together to give a better overall experience becomes really important as well. And I think like Marc said, those are the areas for innovation. There’s certain parts that are just too familiar, too standard, and quite honestly probably work well, but there’s always room for improvement on some of those surrounding areas just to make the process of using a calendar more efficient, more clear. Because it’s really about time management and that’s a very important thing for everyone. And the calendar sits at the center, maybe of that with a few other core apps.”

You have been listed on Product Hunt as the number one product of the day. How was that accomplished?

Marc: “So kudos … go to the marketing team. They really put in a lot of effort and planned it very well from the onset. So a few areas that they focused on. One was building a little bit of a following before so that we had people that knew what we were doing, ready to support us, we had a product that people liked. So that was really important, getting them to say they’re willing to come out the day that we launched to support us. There was also making sure that we had a good hunter to help us push the product out. And then also all the collateral around the videos, the product demos, all that stuff. And then on the day of, a whole lot of hustle. Rounding up all our contacts and all our people that we knew, friends, families, ex-colleagues, everybody. We reached out to people we haven’t talked to in 15 years to give us support for that Product Hunt launch. So again, big kudos to our go-to-market team held, led by Sench on our team to make that happen.”

What is a hunter?

Marc: “A hunter is someone that’s willing to post your product the day that you’re launching, and they typically have a following already. So when they say, ‘Hey, here’s a product that I’m promoting to launch,’ then their followers are all notified, and they know about it. And that helps start the ball rolling. It’s like pushing a snowball down the hill, you want it to get bigger. So it starts your ball a bit bigger than starting small.”

Did the Product Hunt listing pay off the way you thought it would?

Marc: “It did. I think one, it gave us users, which is fundamentally what you’re looking for, and users that have opinions that will give you feedback on your product. Which is exactly what we want it for. Second, I think it gives you credibility for your product. So if you can get product of the day, or product of the week, or month, or whatever, I think it gives you credibility that it’s not just you saying this is a really good product that there’s a community behind it. So yeah, I think it was totally worth it.”

How is Nook making money?

Marc: “Quite simply we don’t. And simple being is that we’re so early, we’re still trying to get to our product market fit. We’re trying to get a product that people are going to love and talk about to their friends. We know how we want to monetize it, which is going to be the freemium model. Basic product is free, and then if you want some additional capabilities, you pay for that. And then from there, there’s also an enterprise version if you want to start administrating for a bunch of people. But we’re not even focused on that yet, we’re trying to build a product that solves the critical problem that we’re trying to solve.”

How do your investors feel about the current lack of profitability?

Marc: “It’s about aligning your strategy with the right investors. Some investors are all about ‘Show me your proof points in terms of revenues,’ others may have other priorities. And so if you know as a company getting revenue right now is not the right thing for your business, get investors that believe in your strategy or else you’re just going to have conflicts all the time. And my previous business that I eventually sold to BlackBerry a decade ago, was also in the calendar scheduling space, which was the Tungl.me business that we talked about earlier.

And when I was doing my Series A, we weren’t about making revenue, we were about building our user base. And so I did speak to a lot of investors and a lot of them, they were like, okay, what’s your revenue model? They didn’t understand the reason why we weren’t looking at making revenue. They weren’t the right fit, and so we didn’t even pursue them. We ended up finding the right investors for the business, and that makes it all better in the long term. So aligning your strategy with the investors is super important in my opinion.”

You did a friends and family seed round. Why didn’t you tap the VC community for funds?

Marc: “So we were — and we still are — pre-product-market fit. If I go to a VC right now — and by the way, there is a VC that’s part of the friends and family round because they’ve invested in previous companies, but they understand that it’s a friends and family round. But if you go to do a real seed round or [Series] A round, there’s a certain expectation of where your business is, and we’re not there yet. And so that’s why we said, ‘Listen, let’s do a friends and family round because we had friends and family that actually wanted to participate into the business and be part of the journey with us.’

So, we did a friends and family round at a good valuation for the investors and for us as well. But knowing that there would be future rounds in the future. So because of the stage where we were, which is pre-product market fit, pre-revenue, it didn’t make sense to go raise more money. Even though I think we would’ve been able to, especially a year ago, maybe not now, but a year ago.”

Is there a point where you will consider VC money or will you continue to go it on your own? 

Marc: “We want to build this to be as big as possible, but we want to build it on solid financial fundamentals for the business. So I think it’s important for us to start figuring out how we’re going to generate some money, have some proof points there, but if we can figure that out and build it, then raising the funds to exponentially grow is definitely in the cards for us. So my take is it’s a bit of both. So we need to prove our business model, we need to prove that we can get to break or show high growth, even if we don’t raise. But then raising the money to bring us to a whole other level.”

Chad: “Yeah, I agree. I think a lot of it at the stage we’re at right now, where we are looking for product market fit, building a product that we think adds value. Once we’ve built a product that provides value, the rest ideally falls into place, and we decide our pricing model, our go-to-market approach, and those types of things. But the stage out right now is really we’re walking into the fog a little bit. We know where we want to go, we think we know where the road will lead. We’ve been down this path before, and it’s really just a matter of executing it.”

Chad, you’ve said that you need to have a strong mentor and a team without an ego. Can you explain those remarks further?

Chad: “That really means combining the right people. It can’t just be a bunch of people who you work well with. I think you need someone who’s maybe a little more experienced, and can give a little more guidance, and is willing to teach … You’re putting a bunch of doers in a room … and I think that’s the important thing, but you do need a little bit of guidance and finding the right person to deal with all these opinionated, strong minded, passionate people is really important. And I think that’s where the mentorship comes into it, mentorship/leadership.

And that really makes the difference to keep everyone going in the same direction because a startup can move so fast, everything happens quickly, all these great ideas being focused and keeping that direction is really important. And having someone who has the ability or the mindset to manage that, but also the experience to help ensure that the path is right is critical. You can put all the right people together, and the good things may happen eventually, but if you’re able to put someone there who can keep all those people focused, you’ll probably get there a little bit faster.”

Marc: “And on the ego side of things. Let’s face it, as an entrepreneur, you have a big ego because you basically think you can do something better than someone else and so that’s why you put your hat in the ring. And so I like to think about how do you deal with ego when you actually have a big one. And so I love the saying that Ryan on our team, one of the co-founders has, which is, ‘We have strong convictions that are loosely held.’ So you’ve got to really believe into what you’re doing, but you got to also know that you can be wrong and change your mind. And so that’s the balance that’s really hard. Having those strong convictions that are loosely held and that’s, I think, what sets our team to a path where we’re not afraid to challenge each other, and to be challenged, and to change our mind.”

How does this approach to governance affect the hiring process and the candidates you hire?

Chad: “It’s really about finding the people who fit that model, have the attitude, maybe have done a startup before so they know what’s involved, to understand the effort, the passion. And I think that’s a big part of it is really passion and drive. Skills can be learned along the way but if you’re not of the mindset to be able to come in and, ‘I really want to build something great. I want to be part of this team basically with a good head coach,’ like you said. But there’s also good teammates around you who you can learn from. And I think that’s what differentiates people. Looking for curious minds learners who just want to do things and build a cool product.”

As leaders, how do you shift your mindset towards delegation rather than just wanting to do it all yourself?

Marc: “That’s why I like to think of it as being the head coach. I know Michael Jordan. I can’t do what he does on the court and same thing with my team members. They’re better at what they’re doing. I have certain skill sets that I can bring but to me is recognizing that I can’t play all the stuff and I’m not the best person to play all the positions. And so having the right people to play the positions that they’re in and to challenge me and what I’m doing is to me, how you build an all-star team, and that’s what we’re trying to do.”

Chad: “And I think I heard this saying somewhere, ‘If you want to go fast, go alone, but if you want to go far, go together.’ And I think we’re in this to go far. And a lot of it is getting the right skill set. There’s a group of people, and everyone’s going to be very specialized, you can’t know everything about everything. And being self-aware enough to know where your strengths are, and maybe where your weaknesses are, or where you’re in the middle is really important because then you can focus on the things that you’re really good at. And if you have people who can do the things that they’re also really good at, that’s important. And that doesn’t mean that you’re not capable of doing something, but it’s also important to realize that this person can do it faster, better, and that’s okay.”

What’s next for Nook calendar?

Marc: “So as we mentioned earlier, we’ve pivoted into what we’ll call just Nook for now, which is a way for people to centralize their notes and their action items into one central place because we know they’re using so many different apps. They’re using apps like Slack, they’re using Teams, they’re using email, they’re using calendars, they’re using all this stuff, and all these stuff are telling them stuff that they need to know and stuff that they need to do. But what we are then doing is taking those notes that you’re putting into our system and then putting more context around that. So I’ll give you an example of a perfect use case.

We’re about to have this podcast together. We’ve had some email exchanges before, we’ve had some other calls, we’ve had some stuff you may have taken some notes. Your notes may be in Notion, your notes may be on a Google Doc. Our calls are linked to this thing, it is all spread. Just before the meeting, you’ll have in our application a beautiful join now button, you’re joining it. But as you’re doing that, it brings you all your context related to the call that we’re about to have. So if you shared some Google Docs between yourselves, if you shared emails with us, you would have it all there in context for you to then be able to use while you’re having that conversation, then you can take your own notes of it. And those notes are then available for you to see in future times. So that’s really what we’re building right now with Nook.”

What is the biggest roadblock you’ve had to overcome while launching and scaling your startup?

Marc: “For me, the biggest roadblock is you’re so eager to get something out and sometimes you want to market it a lot more than what it’s ready. And so being patient to really go through the steps and the iteration that you need to build something that people are going to want and not to proceed that because we’re all eager to get something out and we want the people to use it.”

Chad: “I support that statement. I think having a metered approach to things is very challenging. You feel you’re there and maybe you’re not as there as you think you are. A lot of what we’re doing is very much user interaction driven. So a lot of UI and UX iterations where this metered approach is really important because you do need that feedback to go to the next step, next set of users, next cohorts, build out that functionality. And I think the patience that comes along with that and being able to deliver quickly, but also set very specific targets along the way becomes very important as opposed to boiling the ocean, a common statement, you really need to go in and focus on core deliverables that help achieve that end goal.”

What is your number one piece of advice for aspiring entrepreneurs?

Chad: “For me, based on where I’m at in my life cycle, very much a personal insight is it’s never too late. If you’ve gone your whole career at various startups, either as an employee going through big companies, but ultimately if you have a passion for it and you feel you have the right team, the right people to work with, do it. It’s fun. You’ll learn a lot. If it fails horribly, you’ll learn more than you’ve ever learned before. So go for it. And if it’s not the thing for you, there’s always other opportunities. It’ll happen. Especially if you’re the type who’s considering going into do a startup on your own, you’re probably the type who’s going to be able to find employment elsewhere if it comes to that.”

Marc: “And then for me the advice I would do, one we’ve talked about earlier is, first focus on the people and the what. But once you figure that out, you’re running a marathon and not a sprint. And so taking care of yourself, sleeping is important. Probably the most important thing because it keeps your head straight, keeps you more productive. People talk about work/life balance, whatever but to me, it’s about making sure you’re in a good head space. And you’re going to work long hours, but if you’re enjoying what you’re doing and you like the people with it you won’t feel it. But also take time to do the stuff that are outside of that. Spending time with your family, sleeping, eating well, exercising, doing those things, super important as an entrepreneur.”

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