Deep Dive with Amir Nathoo

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This is a podcast episode titled, Deep Dive with Amir Nathoo. The summary for this episode is: <p>Tune in to The Daily Bolster as Matt welcomes Amir Nathoo, the founder and CEO of Outschool, an ed-tech platform that inspires kids to love learning.&nbsp;</p><p>As the two dive deep into Amir’s journey, he shares his lifelong desire to start a software company. His career path started at IBM, where he built up experience and knowledge before leaving to start his first company. This episode is packed full of valuable insights on professional growth, the scaling process, the importance of founder-market fit, and more.</p>
The beginning of Amir's professional journey
03:31 MIN
Exploring different roles
05:52 MIN
About WebMind
03:17 MIN
Scaling Conduit
03:26 MIN
Scaling the business
02:58 MIN
Becoming the product leader at Square Payroll
02:22 MIN
The most important lesson Amir learned
01:46 MIN
POV on Jack Dorsey running two companies
02:18 MIN
All about Outschool
09:08 MIN
Sitting on another company's board
02:02 MIN
The through-line of Amir's career
01:41 MIN

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Amir Nathoo. Amir is the founder and CEO of Outschool. Outschool is an EdTech platform that inspires kids to love learning, which as the parent of three teenagers, I can say is sometimes a tall order, but a very important and worthy mission. Amir, welcome to The Daily Bolster.

Amir Nathoo: Thanks. It's great to be talking to you, Matt.

Matt Blumberg: Yeah, so let's dive in. So you are a three- time founder. I'd love to start at what at least LinkedIn says is the beginning of your career. So I don't know if you did anything before what you recorded on LinkedIn, but five years at IBM doing software development before you started your first company. So IBM, one of the largest companies in the world, one of the sort of most venerable, and at different points in time revered companies and feared companies in technology, but a very different place in the 2000s than it was in the second half of the 1900s, the 20th century. So we'd love to hear just a couple of minutes about what that experience was like, and how you got from there to, " I want to go start something." Like how you get from the multi hundred thousand person company to the raw startup.

Amir Nathoo: Yeah, happy to share my journey there, and in some sense it was really the other way around. It was almost that I always wanted to start a software company from a young age, and at the time IBM seemed like the best path to get there, and it was really because I wanted to get into software. And at the time in the UK where I grew up, as you can probably tell from my accent, there wasn't many places you could do serious software development. And so when I was graduating, knowing this ambition of getting into software and probably going and starting my own business in software, IBM had a software development lab. It was very highly regarded, a large one in the south of England, in a place called Winchester. And so I definitely approached my time at IBM saying, " I want to get into software. This is a great place to start, and I want to learn as much as possible about software, how it's built, the business of software, as possible." And the inspiration for that, just wanting to get into software was I was very fortunate to be exposed to computers very early. First through games, my parents would buy me a BBC Micro as a toy, and then teaching myself how to program and getting support as a kid for that journey. So software was the staff and IBM was the starting point in my career. And it was foundational in many ways. I joined the software development group in level three support, which was kind of the engineers who are tasked with, once it's established there's a bug going on and maybe a live production system that's down, and it's a problem that can't be worked around, it needs a bug fix, someone needs to code up that fix and address the problem. So it was a combination of software engineering and customer support. And I really enjoyed it because I established that I was actually a hacker, and instead of having to actually develop things to the normal process, you'd be up at 2: 00 in the morning, hot patching a live banking system. I don't know where any other company where you could end up with a 20- something- year- old, responsible for delivering a live patch and not going through any of the normal QA procedures, but just trying to get a live production system.

Matt Blumberg: It's like the equivalent of being a triage nurse in an ER or something.

Amir Nathoo: Yeah. No, it was a lot of fun. Honestly, in retrospect, I didn't fully understand the stakes at play for the people on the other side, but I guess maybe that was a little bit of a help. It was more like a fun game, like, " Let's get this patched as quickly as possible and move on."

Matt Blumberg: Yeah, no, that's interesting. And I love your point about sort of went the other way around, you wanted to start something but you wanted that experience first. So you were at IBM in the UK for five years. What was the signal that you were ready to start something or was it just that you had the idea, and then you made a big move geographically at the same time?

Amir Nathoo: Yeah, totally. And I guess the trajectory there was kind of a process of getting sucked in, and then finding impetus to pull myself out because when you're at the start of your career and your first job as I was then, obviously you have very little context. So there was a time I thought, " Oh, this is cool, this is going well. I'm doing well. Maybe actually I stay at IBM for a period of time and explore different roles." I did explore different roles. I spent some time on the consulting side, I got them to put me through their sales school. I was the only kind of person coming from an engineering background going through the IBM sales school, which was very highly regarded and intensive course at the time. And so I was getting sucked in. But one turning point for me was when IBM acquired a company based in Silicon Valley, and span up an engineering team in the UK to partner with that startup company to share knowledge, and I started to realize a bit more about the structure of what was going on here. It's like, " Oh, the innovation is happening outside of IBM in these startup companies." IBM's buying them and putting them through this awesome scalable QA system and global sales system. But actually the kind of exciting part from working with that, I thought was on the other side, and that reminded me of my original aspirations, and made visible to me both the advantages and limitations of being in a big company like IBM. And so it crystallized for me, and also the realization that five years have passed, and I had the belief which has maybe softened a bit, that if you're going to do this, you better do this soon, life is short. You have a lot of energy when you're young. And I read enough books, I was thinking, " Crap, sure, I've learned a lot, but isn't this just a crutch now that I'm five years into IBM, and I'm not yet done it?" And a mentor also pointed this out to me. It's like, eh, most people who do it do it young, and obviously anyone who's been through the process of leaving a stable job and starting a company knows the psychological pressure that can come, and the realization that it was that was holding me back, not a lack of idea, not a lack of financial resources. I came from a very modest background. I had barely any savings, but I eventually concluded that none of this was a blocker to leaving and starting a company. And so I left with an idea, and a friend who left shortly afterwards to join with, and we funded ourselves by consulting on the side, consulting part- time, which worked quite well, it was very interesting, it was unsatisfying in terms of how quickly we could learn and develop the startup. And so we started looking for funding. And in the UK at that time, no one had made money investing in the internet, whereas in Silicon Valley, lots of people had made money investing in the internet.

Matt Blumberg: Right, right, right.

Amir Nathoo: And so it was like pulling teeth, trying to extract a few tens of thousands of dollars from angel investors in London. And we happened to come across Y Combinator in the early days and said, " Oh, we'll throw in an application." And they invited us for a interview, and 20 minutes later offered us a$20, 000 check. That was just an incredible experience. Now it's like, " Well, that happens all the time. This is Silicon Valley." But back then from founding a team coming from the UK it was like, " Holy shit, does money grow on trees in this place?"

Matt Blumberg: I think the answer to that is, yes.

Amir Nathoo: And now I know some of the reasons why and the whole business model behind it obviously. So it was very eyeopening, and we came over for three months for the Y Combinator program, and I both fell in love with the ecosystem in Silicon Valley from a work perspective, and San Francisco and the Bay Area as a place. Came back to the UK, told my wife, " We should move."

Matt Blumberg: How did that go over?

Amir Nathoo: Well, I wasn't very polished at change management, let me put it that way, back then. I'm still not particularly polished but very unpolished. It was more like, " I have this idea, we should upend our lives and move to the Bay Area." But it was funny, it took a while both from a visa perspective and just a life perspective, and persuaded my wife this would be a good adventure. What did it was a three- week vacation to the Bay Area, where we did a road trip around the inaudible, it was beautiful. Obama got elected, this was in 2008, and it was just a fantastic vacation. And my wife, Kirsty, woke up one morning and said, " You know what? I'm down for an adventure. We're not ready to settle in life, and just be who we are right now." And so it was fundamentally that desire for adventure that even underlies any kind of professional aspiration. And we framed it initially as a one to two year adventure, and now we've been here, several companies later and 14 years later, American systems, two American kids. So it did turn into an adventure.

Matt Blumberg: Yes, I always tell people, not quite as far away, but I grew up on the West Coast, I'm in New York. I always tell people I'm on year 35 of my two- year plan too. All right, so what was Web Mind all about? It looks like it was about a three- year run, and then it looks sort of date- wise like it either had a successor company and Trigger, or you sort of went straight from one to the other. So would love to hear a little bit about your first couple of companies, which are very, very different in nature than what you've landed on at Outschool.

Amir Nathoo: 100 percent. And technically it was one company, but it was a hard pivot that could easily have been a separate company, in retrospect it probably should have been. So it's fair to frame them as two different companies and even pre Web Mind, there was a kind of quagmire of ideas in the early days of YC that turned into Web Mind. But what Web Mind was was a way to save and access your entire browsing history and use it to personalize your search, because back in those days Google search was obviously a big thing, but things like Google Drive and local search hadn't really been developed. So searching across all your information, including behind logins and on your personal computer was obscured. And so the concept was a browser extension that would record your activity, including behind logins. And then when you did searches took over the right- hand side of Google and display search results that Google couldn't possibly display, from your own information and from your browsing history. And this was an intriguing concept to the same kind of people who maybe used Delicious, if you remember that service or people who like organizing their information.

Matt Blumberg: That was Albert, right? That was Albert Wenger.

Amir Nathoo: Yeah, no, that's right. And Joshua Schachter was the founder. I don't know Joshua, but inspired by that kind of thinking. I worked with content management systems, enterprise content management systems at IBM. And so there was continuity with that idea of methods of content management, methods of retrieval and organization. And we stumbled upon this business model where, " Hang on, we're taking over the right- hand side of Google for these search results." Well, that's really valuable real estate, affiliate links and ads is the obvious place to go. Then in retrospect, probably given the size of the audience that was interested in that kind of tools, we probably should have gone freemium as a route. But we explored that for a while and we got to some decent size of revenue. The problem with the business I think was twofold, one that I've already alluded to. I think there's a limited number of people who are truly geeking out about that kind of information retrieval and really organizing their information. It's a limited market. And we also learned, we saw the companies like Conduit, which at the time this big browser toolbar company, and the motions you had to exercise in order to get this toolbar distributed and then monetized, end up being super sketchy. I mean I think it was all legal, it's just like it turned our stomach.

Matt Blumberg: Yes.

Amir Nathoo: inaudible i. e. toolbars, and then secretly replace the Google page with your own search page to carve us ad revenue. I mean, sure that could work, and I guess it's legal because companies did it, but it wasn't the way we wanted to make money and create a business.

Matt Blumberg: And then how'd the business do?

Amir Nathoo: So a relatively small scale of revenue, we raised a little bit of money, it was survivable, but we decided to pivot because we didn't see a path to scale, and or the path to scale were not what we wanted to do with our time. So basically we as founders lost faith that this is what we wanted to do, and the size of the opportunity. But what we had built in the process of building Web Minds was infrastructure that allowed us to create these toolbars that worked on multiple browsers at the same time, without needing to code them multiple times. And at the time we were thinking about pivoting, mobile platforms were taking off. So the app store, Android, the Google Play Store, and mobile development was the hot thing. That was the area everyone wanted to build it. And the realization occurred was that the same problems that we had addressed with toolbars were present with mobile applications. And we realized we had this framework which could be applied to mobile apps to say, " Code once using this framework and set up APIs and build service, and we'll create you native iOS and Android apps and potentially other platforms down the line." Faster speed to support more platforms. And so we pivoted and changed our name to Trigger. io, which was a framework and cloud build service for developing native mobile apps while coding in JavaScript. And that was a better startup and a better attempt where we got to a greater scale because it definitely met the moment in terms of user needs. And it was a very different business though because we'd be operating like a consumer business with a added affiliate business model. And now we were doing small business and increasing like enterprise sales while building dev tools. But our empathy for the problem, our connection with the problem was much closer because we'd experienced it ourselves. So we were nearing, getting more towards founder product market fit and having successfully identified an urgent need, which was in a much more visceral way than our first attempt.

Matt Blumberg: And by the way, founder market fit is huge.

Amir Nathoo: Totally.

Matt Blumberg: It's so important. It is one of the things that we're very fortunate we have at Bolster. We have a whole team of scaled senior executives helping other companies drive teams of scaled senior executives. And it's way more meaningful for us than running Return Path, and a lot of us did both companies, even though we loved Return Path, it was a great company, a good business, but none of us ever used the product. The product didn't mean something to us personally. And that's a big, big difference.

Amir Nathoo: 100 percent. And I think going into startups, it was more like the first mission was, I want to found a company because I want to be successful and creative and take a different path. And then with Trigger, it's more like, " Yeah, I still want those things, but we need to solve a problem here. We don't want to be off the sidelines. We want to be doing something valuable for people." And we've identified something that seems to be valuable for people and have the proof points to do that. And we have some experience of why it's valuable because we've experienced the problem ourselves. So it was kind a different mentality. It's that hard pivot.

Matt Blumberg: Yeah. All right, so you're three years as Web Mind, a hard pivot, three years at trigger. io. And so how did the second three years go?

Amir Nathoo: So it was a lot of fun, and we made a lot of progress. We raised more money. In retrospect, we should probably have done a hard reset and just done it as another company because there really was... We could have built it all from the ground up with learnings, but at the time it felt kind of scarier to do that and easier to persist with the corporate entity. But we raised more money. We went off to this opportunity. We scaled sales, initially by targeting other startups who were busy, a lot of new startups building mobile development apps. And we built a team larger than before and we got PR, and we scaled revenue further than we had before. Two things came to light in the journey that started to make us concerned about scale actually gradually top out at a certain point. One was a market reality. Part of the thesis of Trigger was that there was going to be consolidation in how mobile app developers developed the front end of their apps, and that consolidation was going to happen via some kind of cross- platform development mechanism. And we wanted to be the one. And one thing we observed is that did not happen. Mobile web developers used a variety of different frameworks including no framework at all, and actually no framework at all was the central competition. And another organization was while we identified a real customer need and urgent problem and concrete ROI, the front inaudible was almost regarded as so important. That's not clear. You kind of outsource elements of it, and get help is almost like it's so important you want to use the best, which is NATO, and invest. So you're always playing this uphill battle. And that's in contrast with the backend where you saw all these backends as a service rise, and there to be much more consolidation on the backend. And one thing I learned through that process was that, yes, it's important to identify a real tangible customer need, but you also have to think about the barriers to buy. And you don't necessarily want to go for the hottest part of the need first because it could be so important to the customer that the barriers to get started will be so high, it's sometimes better to go after a real need, but that's kind of easier to outsource. Just a typical, like an example I used to use at the time was logging. There were these platforms of service that started doing ridiculous revenue from inaudible, you're doing logging, is that really a need? It's like, well, you need to do it. It's considered a hygiene feature. Is it the most important thing? No, it's not the most important, but you kind of just need to do it. And no one really wants to be spending the energy there. So it's easy to go to a vendor and say, " Please provide me infrastructure to improve logging."

Matt Blumberg: And all of a sudden it's Auth0 at Okta.

Amir Nathoo: Yeah. And then expand from there. And it's like, " Oh, just because you found a critical customer need, it doesn't actually mean it's the right strategy to go head on at that need." And actually that influenced a lot of how I think about the strategy at Outschool, because kids' education is obviously a very high stakes decision for parents, and that was a key part of it. We also made some execution mistakes, intentionally slowing down our growth because it felt out of control in terms of our ability to deliver on the demand, which I now realize is a standard evidence of product market fit. And you don't want to go too far out of control, and there are stories about startups that take that too far, but actually that's something to lean into. And we slowed growth more than we should have, and we never recovered momentum. And that made me conscious much more about the momentum and management behind growth. And just because, I don't know, things are feeling uncomfortable inside the company and in how you're able to deliver and in support, it doesn't mean you slow down. It means you fix as you go along and you have to find the right velocity to manage through. So that was a key execution learning I took from that.

Matt Blumberg: And what was the ending?

Amir Nathoo: So ultimately we plateaued based on these observations, and we decided that this wasn't going to become... We're hyper ambitious, this wasn't going to become the breakout success. And so it makes sense to find some kind of exit. And also the realization, and it comes back to kind of founder fit. It's like we might've been a fit in terms of understanding the problem space and skills needed, but it wasn't actually our passion. So actually when looking for an outcome, it was actually like we don't actually want to, we want to do it right by our team. We want to do right by our investors. We actually want to craft an outcome here that we don't have to work on developer tools for the next two to five years. So it was quite intentional to go somewhere that would value what we built and the experiences that we gathered along the way, but be in a completely different domain. And so we ended up doing a deal with Square to acquire predominantly the team.

Matt Blumberg: Okay. That answers my next question. Looking again at your profile here, my question was going to be, how on earth did you end up as the product lead for Square Payroll, before being a founder? So presumably that's the quick answer. What was the experience like at Square?

Amir Nathoo: It was a roller coaster ride, a hell of a lot of fun. At this point I'd spent what, six plus years feeling like, in retrospect making a lot of progress and learning, but at the time feeling like I was banging my head on a brick wall, trying like find initial, find a product market fit and get scaled to get involved in a company that was busy scaling and expanding, and then realize, " Oh, I could use all these learnings and skills that I developed as a founder to really hone my craft in a product in particular was fantastic." And this was a time at Square where they went, and in my time there from 400 people to 1, 200 people in 18 months.

Matt Blumberg: Right. That's so interesting.

Amir Nathoo: Coming through the back of a big fundraise, expanding out of their core. And the reason they were interested in bringing founding teams on was because they were doing a lot of expansion and looking to scope out new areas of business development. So that's how I ended up founding the Square Payroll product within Square. This was a new area of expansion that I'd come in and identified. There was a lot of existing thinking, a lot of existing advantages they can use. It was a wild ride to be at that stage to see the chaos of the startup. And this was my first experience of a growth stage startup. So it felt completely chaotic, and I was like, " What the hell is happening here? This is a terribly managed business." And now I'm kind of running a growth stage company. I have a lot more understanding and empathy for the leaders at Square during that time, but it was just a mind- blowing experience like, " What? This is the level of disorganization and chaos." But you can't argue with the results. I learned something from that in terms of what seemed to me the right ways of working and structure and organization, and actually skirting the edge of chaos. It's kind of almost what you need to do in order to grow fast.

Matt Blumberg: What's the most important thing you learned?

Amir Nathoo: Well, I learned about myself that if I'm going to be in a growth stage startup, I better blooming well be running the thing.

Matt Blumberg: Yes, right.

Amir Nathoo: I didn't last that long, I came in with the best of intentions being, I don't want to be one of those kind of jerk founders who comes in and just leaves after a relatively short amount of time. I really want to learn from the people. And I did learn, but I also had my eyes open to how much I could do, and I didn't really appreciate the skills that I had developed, because when you're a founder, it's hard to reflect. And then I came in then I realized I could do all these things, like not being afraid to pick up the phone to a customer as a PM and not bother having to go through other teams, being more self- sufficient and all of that. And honestly, I think my learnings from Square were a little bit in retrospect, almost in contrast. I'm not sure I fully appreciated the experience at the time, but one of the key ones was around change and the uncomfortableness and rapidity of change, and well, I guess relearning some of the experiences I had with Trigger, which is that uncomfortableness, chaos, even misalignment is a symptom of fast change. It doesn't mean you're doing anything wrong as a business, and if you're pushing hard enough and if you're moving fast enough, that's going to happen. And the work is just to keep working towards alignment, towards organization, towards that sense of control until you change it all again before you get there. And that's the startup journey, and so seeing that was a key learning for me.

Matt Blumberg: So one other question. I'm not sure if the year you were there was one of these years, so the answer might be you don't know, but I've always been fascinated by the notion that Jack Dorsey was the CEO of two very high profile large companies at the same time for a few years. So I don't know if that happened when you were there or after you left, but do you have any insight into how that worked?

Amir Nathoo: It's funny. I don't actually remember whether that was the overlap, but the thing that I do remember and actually was, and now I remember was a key learning for me. I feel like I didn't work for Jack directly, but I interacted with him and saw him, and he was always very high- level. And so it's not actually surprising to me that he'd be able to do that. And his superpower was as a visionary and a salesperson, and me and my co- founder that we brought in, we sat at the back of weekly debriefs, and Jack would be doing this, like his inspiring spiel. And one part of us would be like cynical Brits, " Yeah, yeah, yeah." But we couldn't help but be taken along, and we just couldn't help it. He was just that kind of, he would paint that picture, even though the voice inside you said, " That's unbelievable. That's crazy, how are you even going to do that?" inaudible so well that another part of you was brought along, and that kind of made me think in terms of how I realize that you might hear these cynical voices inside yourself or from others when you're painting this picture what the future could be. But that shouldn't stop you doing it because you are bringing people along. And yeah, you're going to encounter some cynicism, and yeah you're going to encounter doubt when you're trying to shoot off the big things, but that shouldn't hold you back. It's a useful and necessary part of trying to do great things.

Matt Blumberg: Yeah, for sure. Sure.

Amir Nathoo: So he did that really well. But I have some questions then about how that was translated into execution. But I think the other thing that I saw from Jack was just he brought on brilliant people around him, and so successfully kind of filled in for the other parts, where maybe he wasn't so focused.

Matt Blumberg: Yeah. Well, and presumably he had really some strong operating executives or chief of staff or a COO or head of HR or whatever, that kind of kept the trains moving on time while he was being the visionary.

Amir Nathoo: Totally.

Matt Blumberg: All right, so let's move to your current chapter. So 2015, you start Outschool with a mission of inspiring kids to love learning, which I absolutely love. Talk about Outschool, how did you get there from Square Payroll?

Amir Nathoo: Well, multiple influences. And by that point I'd also gained the confidence to say there's certain criteria about picking what you might do next, but it doesn't necessarily have to be anything related to what you did before. There's some underlying criteria. And I didn't necessarily want to start another startup. I was aware of how hard it was, so I more framed it as taking a break and pursue projects. I was very intent on only starting a startup. It was kind of pulled out of me by customers, by my own enthusiasm, and being very conscious of not forcing it, because I felt I forced it trying to chase some kind of dream or success in the past, whereas this was like, " Yeah, I have ideas, but this has to be something the world needs," and this kind of pulled out of me. And I was also conscious of really, I mean what we kind talked about about founder fit, starting with my own motivation. And at the time I did not have kids, but I knew I wanted to have kids soon. And I was also very conscious like, " Hey, if you're going to do a startup and have kids, that's tough, but what if I could combine my next thing with my life and make it relevant."

Matt Blumberg: Ruthless efficiency.

Amir Nathoo: Yeah, it's just like, " Well, it's hard so I better be damn efficient, and it better be useful and integrated with my life." And that way reflected on education. And I don't know honestly why I hadn't reflected on education before. I guess obviously the thought of having kids got me thinking about it. Both my parents were teachers, and I realized I had some strong views about education that I developed, and I hadn't really thought that through until I've really thought, " What do I want for my kids?" And I was like, " I'm not sure what I had for my kids, all the elements of what I had that I do want for my kids." And I started realizing the things that I've used and the skills that I developed and needed as an entrepreneur, how much did I really get that from traditional schooling in college? And even though I had the most fantastic education that you could get in the UK, and I started to realize so much of what I used was because of my parents and things I had pursued out of school. And that's where the name come from, out of school learning. And in particular, just like my interest and love of software, and the fact that my parents supported that interest, I started to realize there's a discrepancy here. It seems like I'm sensing a discrepancy between what traditional education is designed to deliver and what I think has been important for me, and I'm reflecting on the future and what I'd learned about the changes in the world through technology, and like, " I think this discrepancy is going to get worse, and I think there's going to be more parents of young kids like me now who are going to sense that discrepancy and want something different or additional." And that's what led me towards, a set of motivation that led me towards education, led me towards thinking about out of school learning, going directly to consumers rather than selling into the traditional system. Also, another observation was technology had not really transformed education in a significant way. And there were not big exits, and there were not big success stories, really transformational inaudible. Sure, there were some IPOs selling into the existence, but it was not a well- regarded or hot area. But I had the sense that there was this discrepancy growing between parent satisfaction with traditional education, but behavior hadn't changed yet. And I sensed that there's going to be a time when there's going to be a seismic change, because when pressure builds up like that, when dissatisfaction increase and behavior's not changing, that's pressure building up, and there's going to be some catalysts. And if you can get the timing right, there's going to be a change here. Could you accelerate that change, could you time it right? So I thought if the timing is right, if the model is right, this could be a massive opportunity. Key risks are market and timing, but I thought, " I'm patient, I've had enough success at this point, I don't need a fast exit." So again, found a fit. It was like, " I'm willing to be patient here and plug away at it and try and work on things that were far out." Again, Outschool, far out of traditional education, because everything that had been attempted closer into traditional education hadn't got that breakout success. So we're going to go really far out, and we're going to be very patient, and we're also not going to be arrogant. So when you say the mission of inspire kids to love learning, I can go more into what that means. We didn't start with that. We started with, " Hey, we're going to build a marketplace focused on consumers, and we're going to target home schoolers because that's where there's a lot of innovation happening and people have an urgent need, and we're going to learn, and we're going to spend multiple years just doing that. And then we're going to form our own opinion and submission, because a lot of people coming in from tech into education were like, "We know how to solve this. We've learned everything from Google. All you need to do is just apply this technology learnings to this new field and it'll work." And it didn't. And there'd been plenty of flame outs in education I think for that reason. Whereas we came in and were like, " We're explicitly not going to have a very big vision. We're going to have a broad marketplace. We're going to learn from this initial audience." And that's how we got started.

Matt Blumberg: And is it working?

Amir Nathoo: Yes, to an extent. I mean, I think that's to a extent bit is a subject of any point in stuff, it's always to an extent. Had you asked me when we started we'd be where we are today, I would've been like, " Awesome. It's great." It's been a rough ride to get here. The kind of key surprises along the way, were first discovering the live small group, live online format. And when we started we were offering a marketplace of classes. We experimented with in-person class, we experimented with content. And we saw some of these home schoolers get together with teachers on Skype, and get into small groups to learn. And we thought, " Well, that's kind of like a really, really small niche, but hey, why don't we throw live classes over video chat up in the marketplace and see what happens?" And that part of our marketplace just took off, and we started to realize, " Oh wow, this new format is actually, we thought it'd be a bunch of tech issues, it's actually not as bad as we thought. People are familiar enough with this format." Zoom was just starting to grow. And so the technology was just good enough. The adoption was good enough. And we started to realize, " Oh, there's big advantages to this in that it combines the best of in- person interactivity with online availability and convenience." And that parents could pay less for learning experiences and teachers could earn more than other formats, because the cost of the teacher's time was split amongst the group. And you didn't have to pay for an in- person location. And so the economics, but no one had scaled it because it was only just possible. And it was hard to scale because you've got a marketplace, you've got live classes. But we succeeded in scaling that once we fully focused on it from 2017, because we'd picked the right early adopter audience of secular home schoolers who had an urgent need. There were enough of them to solve the initial chicken and egg problem that you have in a marketplace, and it had sufficient schedule availability to create enough liquidity in the marketplace to start scaling. So that was a big surprise. The second big surprise was COVID. We didn't found this company or decided to do live online classes because we expected there to be a global pandemic. But when the global pandemic hit and the schools shut down-

Matt Blumberg: It must've blown the business up.

Amir Nathoo: I mean, there was this moment in February 2020 where the CDC issued this notice saying, " We think schools might have to shut if this gets bad," and they're going to have to move to internet- based tele schooling, is the phrase they used. And I locked onto that phrase like, " What the hell do they mean?" And I was like, " Oh, shit, they mean what we do." And at that point I realized we had more experience than any other company or organization in the U. S. at how to run these classes. And we started doing things like offering free webinars for schools and teachers, but it was a drop in the ocean. And when school closures hit, so many parents came to us. Our business grew 15 X in 2020 in revenue, not just usage from a multiple dollar starting point. So it was a crazy ride. So just keeping the wheels on the wagon during that time was tough. So that's what I mean about, it's great obviously that we were able to help and it was great for the business, but it was a tough time. And then of course as schools reopened, we had a reset in our business, predictable but hard to get through. And now we're back onto a more steady growth trajectory.

Matt Blumberg: A sustainable path.

Amir Nathoo: So very, very happy with how it's going. And many of our hypotheses have played out, but been a roller coaster to get here.

Matt Blumberg: Well, I wish you a lot of luck with Outschool, it's a tremendous mission. Let me shift gears and ask two more questions. So the first one is about your role as a board member. So you're an independent director of someone else's company, not Outschool, Scribe?

Amir Nathoo: Yeah, inaudible

Matt Blumberg: So my question for you about that, because I talk to CEOs all the time about the value of sitting on someone else's board. So I would love for you to give just a super quick answer of, what is the best thing you get out of being on someone else's board?

Amir Nathoo: The change of perspective. Obviously as a leader, you always try and see things through other people's eyes, but to actually be in a different seat, looking at a different company that you care about but aren't as attached to as a founder, just provides a greater level of understanding and empathy when dealing with your own board. And I've learned a tremendous amount through it. I would say it's not something to take on lightly because there's a lot of responsibility, time and commitment that comes with it. And I want to do just as good a job for that company as I do for Outschool. And so it's a big investment, but at the same time, on a personal level, and for Outschool, I think I've gained a tremendous amount by being able to see another company up close and yet with a certain amount of personal and emotional distance. So I guess I'd recommend it if and only if it's the right time for you personally and the right time for your company, for you to be able to take that time. But I think it really is a win- win. I would never consider having more than one board seat while also operating my own company, but I really do see it as a win- win because of that learning and that change in perspective.

Matt Blumberg: Right. So my last question for you, as you sort of think about the arc of your career, everything we've talked through today, is there a through line you can point to, one thing that's held it all together? Because I love hearing the experiences, and like A which led to B, which led to C, which led to D. But is there sort of one learning or driving force or driving principle that goes from finishing university through scaling Outschool?

Amir Nathoo: I think I've had a very varied career, and in some ways a very non- traditional journey. But I think the through line, which some might frame as risk- taking, but I might call more naive, jumping in at the deep end. At every turn I've taken a harder path or a path that in retrospect seemed completely foolish, but in aggregate works for me, and has taught me a lot. So I mean maybe learning actually is a thing because that's what you get as the end result of jumping at the deep end, faster learning at the expense of your own comfort.

Matt Blumberg: Well, look, I think most successful founders would agree that having a learning mentality and a growth mentality is a very healthy driving force. So a great note to end on. Amir, thank you so much for spending time with me today. I love what you're doing at Outschool, and I'm glad to have a seat somewhere in the arena to see what's going on with it. So good luck getting the business through a growth stage.

Amir Nathoo: Thanks so much, Matt. It's been a pleasure talking, and really glad to work with Bolster.


Tune in to The Daily Bolster as Matt welcomes Amir Nathoo, the founder and CEO of Outschool, an ed-tech platform that inspires kids to love learning. 

As the two dive deep into Amir’s journey, he shares his lifelong desire to start a software company. His career path started at IBM, where he built up experience and knowledge before leaving to start his first company. This episode is packed full of valuable insights on professional growth, the scaling process, the importance of founder-market fit, and more.