The missing miles in education

I like to think of learning as a series of journeys. Those journeys have starting points which could be an interest “I love penguins!”, inspiration “I have an idea for a rocketship”, goal “I want to be a doctor” or challenge “my math skill is holding me back”. The journeys needn’t have fixed end points and some legs may be slow meandering explorations, others straight-line sprints.

An ideal education system would meet a learner wherever they are and help them get to where they want to go next, using their preferred means of “transport” and on their schedule. Schools are like intercity railroads linking the major hubs. They should be complemented by a huge network of roads and vehicles since few journeys just go from hub to hub.

Outschool is building that network to complement schools. We aim to fill the first miles of motivation and pre-requisite skills and the last miles to achieve a goal, get a job, finish a project, or get to a natural closure of a motivation or interest. We want fill in all the middle miles of possible journeys and schedules. We want to be every kid’s second school.

Could we build an education system that helps any learner on any journey? An analogy to modern transport makes me think we can. Our first vehicle type is small-group classes that meet over video chat. Teachers create the learning journeys they’re excited to share. Together, we’re filling in many missing miles in education.

What I learned from my father

My father, Manusurali Hassanali Nathoo died in 2015 from Parkinsons. He was my hero. He was gentle, softly spoken but strong in his convictions and reaction to life's hardships. He was a great listener and a man of few words. It turns out I'm a lot more like my Mum!

He was adventurous. He was Indian by origin but born and grew up in Kenya. He moved to England to get his PhD in Physics and then married my Mum - a fellow expat and physicist from Czechoslovakia. He became a businessman then a science teacher. He visited California and had a soft spot for San Francisco. He was proud of his family and achievements but felt betrayed by some of his brothers.

I valued his advice enormously. I wish I had dedicated more time to him and our relationship when he was alive. I learned so much from him directly through what he taught me, but also through how he acted and who he was. 

He gave me a set of mental and emotional tools that I use so frequently I'm probably unaware of most. Here are some snippets of advice that I can remember:

  • Write the first sentence. Get started now, you can always revise it.
  • Courage isn’t lack of fears, it's continuing despite them.
  • College is for finding a wife.
  • Business is risk.
  • Being bored is your own fault. There are so many interesting details if you just look closely.
  • Why be happy with 9/10 when you could get 10/10?
  • Your preferences aren't set in stone, you get to decide whether you like vegetables or not.
  • You get to decide whether you're happy with what you've got: I only need a cup of tea and a book.
  • Don’t judge a book by its cover: I was robbed once by men wearing suits.
  • Beware of people who seek power over others.
  • Protect yourself. Just because something is unlikely doesn’t mean you won’t be unlucky.

There's more that I take as advice by trying to follow the example he set: be kind; be happy; be different; you may need to move around the world to find a place to make your home; tell a story; tell a joke; invest in learning; don't rely on others.

As I write this I find it impossible to convey the depth of meaning to me without the context, remembering the colors, his voice, how it felt. I guess to truly learn something you have to be there and experience it for yourself.

My journey to founding Outschool

I was recently interviewed about my career and journey to creating Outschool for the alumni magazine of St. John's College, Cambridge. This led to a lot of fond reminiscing and hopes for the future of learning.

What did you study at St John’s and what are your abiding memories of the college and your time here? 

I graduated in 2002 with a MEng in Electrical and Information Sciences. I actually started out studying Maths, completed Part I and then switched to Engineering for Part II. After a gap year at IBM and seeing engineer friends building robots, I was itching for the creative and practical aspects of engineering. 

I remember the intensity and focus needed to keep up with the academics while juggling myriad other interests. I learned to row with the college boat club, to fly with the University Air Squadron and to ballroom dance competitively. I remember excitement of so many new experiences and people. I found friends I'm still in touch with who liked the same ridiculous, nerdy jokes that I did, and made me feel like I belonged. At the same time, everyone seemed so smart and ambitious I felt constantly challenged to raise my game.

What did you take from your degree that has remained with you in your professional life?

After graduating I went into software development at IBM. I've been in software ever since and that isn't something I studied formally at college - I'm a self-taught programmer from a young age. Although I haven't used much of the maths and engineering topics I studied, there are many other skills I took from my degree that I have used.

In the third year, one of the courses involved working in pairs to design and build a compression algorithm. We competed with other teams on who could come up with an algorithm which resulted in the best-looking compressed images given a file size constraint. This was great practice for doing technical work in teams and working to a deadline in a competitive environment. We ended up winning and my lab partner, Kirsty, is now my wife.

Half of the credit for fourth year engineering came from an independent research project - I worked on modeling "grey box" control systems. The project involved long-term independent work on a speculative project with uncertain outcome. That sounds a lot like the startups I've been involved in!

Switching from maths to engineering was tough. One of the first engineering modules I took was designing electrical circuits. I kept trying to determine the optimal circuit design and prove that it was "right" rather than using heuristics to quickly find a design that satisfied the requirements. That switch helped me understand that different domains need quite different ways of thinking.

Tell us how you came to work in the field that you’re in and what you worked on before this.

I'd enjoyed writing software as a hobby since I was 5 when my parents bought me a BBC Micro computer to play games on. When I graduated in 2002, the software industry and internet seemed well on their way to transforming business and society as we knew it. Despite the 2001 dotcom bust, I thought the industry would change the world in much larger ways than it already had. As Marc Andreeson of Netscape later put it - software would "eat" the world.

So after graduating I joined IBM first working in software development and then consultancy. I spent 5 years there but I'd always had the itch to start my own company and eventually found the inspiration to do it in 2007. I left IBM with a colleague, James Brady, and we teamed up with a friend, Patrick Buckley, who I knew from his year at St John's with the MIT exchange program.

We sought investment for our product ideas and were surprised when this came quickly from Y Combinator, a seed investment fund that was just getting started in Silicon Valley. They were far faster and less risk-averse than the British investors we were speaking to - they flew us out and wrote us a $20K cheque after speaking with us for 20 minutes. We attended their program in Silicon Valley for 3 months at the start of 2008 and I quickly fell in love with San Francisco. By 2009, Kirsty and I had moved for what we thought would be a 1-2 year adventure. We're still here now with no plans to move.

After many twists and turns, we ended up building - a mobile development platform that allowed web developers to easily create mobile apps for iOS and Android using Javascript. It's a solid small business but didn't achieve the growth we were looking for as a startup. So, in 2013 we did a deal with Square - a larger startup that has now gone public on NYSE - to acquire the team in exchange for stock. I spent 15 months at Square as they grew from 400 to 1,200 employees and approached IPO. I worked as a product manager there, founding Square Payroll, a new product line for the company.

Tell us about Outschool – what the organization does, when/why it was founded, its successes so far.

I founded Outschool with Nick Grandy and Mikhail Seregine after leaving Square in 2015. Nick had previously been the first engineer at Airbnb and a product manager at another education startup. Mikhail had helped build Amazon Mechanical Turk and Google Consumer Surveys. 

Outschool's mission is to inspire kids to love learning by providing them with innovative learning opportunities outside of the regular classroom. We're doing that by creating a marketplace for live online classes for kids - you can think of it as an "Airbnb for kids' classes". The classes are offered by independent teachers and take place in small-groups over live video chat with assignments and feedback between the live sessions. 

Families use Outschool's classes to accelerate their kids' learning, catch them up in core subjects, or to pursue interests in subjects that are not typically offered in regular school. We’re an alternative to expensive private school education, personal tutors and other extra-curricular programs.

In 2016 we released an early private beta product at and raised $1.4M in investment from Y Combinator and a fund backed by Sesame Workshop, the makers of Sesame Street, as well several other Silicon Valley investors. With our private beta release, we brought on tens of thousands of families across all US states and 24 countries. We launched publicly this summer and are now growing fast after the back-to-school rush in the Fall.

In what ways is Outschool a pioneering organisation?

Rather than just using software in the classroom as a teaching tool, we're looking to use it to transform the nature of the education system itself. We're doing that by offering a new format for learning with a marketplace-based approach.

Live online classes are a new learning format that have been made possible by the evolution of group video chat technology and the bandwidth to support it. They offer important benefits over other online and offline options:

Accessibility – Classes are accessible anywhere with an internet connection and the cost is split between families offering a lower price point than private tutoring.

Collaboration – Learners interact with a teacher and peers rather than studying on their own. Social experiences enrich learning. Nothing can replace a great mentor or exploring ideas with peers.

Choice – Families choose their teachers and their classes based on their needs and interests. They choose from teachers across the world and are not limited by the offerings of their local school or community.

Online community marketplaces, like Airbnb and Etsy, are amongst the great innovations made possible by the web and we’ve applied this model to live online learning. By letting learners choose their classes and teachers we deliver on the promise of personalized learning to adapt education to individual needs. Other models are inherently limited by a fixed curriculum and faculty.

Is digital learning the future of education?

Online learning is poised to play a much larger role in kids' education. We see a future where in-person learning is enhanced by online learning to offer a breadth and depth of educational opportunities not possible today. Most schools can't offer a broad enough range of classes to allow kids to pursue all of their interests and meet all of their unique educational needs. 

Individual creativity, differentiation and directly observable skills are increasingly valued over standardized knowledge and credentials. So the future education system will have to deliver “mass customization”, and I think that's best delivered by an ecosystem of many different institutions. Schools will play a part and so will new, online options.

Give us your take on the importance of independent learning, including any interesting stories or encounters you’ve had that relate to the topic. 

My own experience with independent learning transformed my life. I taught myself to code from age 5 because at the time you needed a lot of technical knowledge just to start a computer game up from a command prompt. I aspired to write my own computer games but no schools at the time had coding or computer science courses. Seeing my interest, my parents found a retired economics professor who had started teaching computer studies on the side.

Today, coding classes are relatively commonplace, but what's next? What are the things that seem like niche toys today but will turn into the powerful tools of tomorrow? Standardized curriculums are extremely important to provide a core base of knowledge but I think kids will need more than that to be successful in the future with technology driving fast change in the economy and workplace. The parents of young kids now have grown up with the internet and they know that following a "standard" path is no longer a sure thing. 

Independent learning outside of regular school isn't just about acquiring niche or vocational skills. It's also about meeting and collaborating with others around a shared interest. At Outschool, the most inspiring moments are when we see learners join a class from diverse locations like California, Georgia, Utah, Ohio, Canada, Russia and Australia. They learn with each other and explore a shared interest led by a passionate teacher. In the current political environment in the US, connecting learners from different backgrounds, cultures and views seems more important than ever. Luckily for us, we see this everyday.

What are the challenges of running such an organisation?

Our biggest challenge is awareness. As awareness of Outschool's offering grows, we’ll be able to attract more teachers and classes, which in turn will attract more parents and students to fill more courses. And as we grow, we’ll need to work to make more traditional institutions see live online courses as a way to enhance in-person curriculums.

In a big company you can use the existing brand and credibility to open doors, get attention and acquire customers. With a startup you only have the vision, the quality of your early product and ability to move fast. You compete on your merits with limited resources. People have described building a startup as like trying to fly an aircraft without an engine, and frantically trying to build and attach that while plummeting to earth! It's challenging but I love it. With 10 years of experience building technology products and teams I feel in my element.

What are your hopes for the future of Outschool?

Our goal is to reach millions of families worldwide and have them learn and connect through live online classes. To do that we’ll keep recruiting teachers and have them bring their creativity and passion to our marketplace. It is the quality and range of the classes offered that brings families to our site. I'd like to see interactive online classes become a standard format and Outschool become every kid's second school.

What advice can you give to new graduates who are entrepreneurial? 

There is a lot of advice online on building businesses and some of it is quite good. If you think you want to try a startup, as opposed to building a different kind of business, read Paul Graham's essays starting with Startup = Growth, and watch the videos in Y Combinator's Startup School series.

My own startup tips are:
  • Start soon. Startups are hard and need a huge amount of energy and inspiration to be successful. You have the most energy when you're young and it takes a long time to build a significant company from scratch.
  • Keep your personal expenses low. If you become addicted to a high salary it will become increasingly difficult to start a company. Many people take high-paying jobs thinking they'll save up to do a startup later, but by the time they feel they have enough savings, they've become too comfortable with an expensive lifestyle.
  • Network with the right people. To build something people want, you need to meet potential customers - people who have urgent problems that need solving and money to spend on them. And building a company is easier when you have relationships with creative, energetic people who could help you as co-founders or partners. 
  • Be original. You don't necessarily need to have a new idea in order to make money in business. But if you go after an audacious goal in an original way, more people will be inspired to help you. And if you're going to put all that effort in why not aim to do something new that you can be proud of?

Outschooling in the Bay Area

Homeschooling is interesting because, if some new approach is going to disrupt the current education system and change it radically for the better, it seems likely it would come from outside the system.

By necessity, parents who homeschool must try new approaches in order to find something that works for their child. With 1.77M homeschooled students in the US - 3.4% of the school-aged population -  this is the community where experimentation / iteration amongst educational approaches is happening the fastest. As a result the future of education is likely to come out of this community.

Yet it is an overlooked community. For various reasons, the mainstream regard homeschooling as a niche approach suitable only for the weird or the wealthy. That’s a prejudice that doesn’t reflect the reality of the growing movement I've observed in the Bay Area.

What I found

I first became interested in homeschooling several years ago after a friend with six kids began homeschooling in San Francisco out of necessity - the public school system wanted to send each of her kids to a different school. Instead of hiring six Ubers each morning she decided to start homeschooling her kids herself.

What she told me about the experience was very different, and much better, than what I expected:
  1. It only takes 2-3 hours of study per day to keep up with the regular school curriculum since the kids were able to study when they were best prepared and motivated. No time was spent on bureaucracy / classroom management.
  2. The kids could deep dive into their own interests, thus learning self-direction and creativity without the requirement to stick to a fixed schedule and curriculum largely driven by logistical concerns
  3. A lot of basic material could be covered through online courses, such as those offered by Khan Academy
  4. A lot of learning occurs outside the home and is social
The last point was the biggest surprise to me. Especially in the Bay Area, there is a wealth of group learning activities that are offered outside of regular school. The Exploratorium, Academy of Sciences and Museum of Craft and Design, to name but a few, offer tours and classes. New microschool startups, such as QuantumCamp which offers one-day per week science programs, are popping up. Parents group together to informally organize their own classes.

For example, one parent organized “Thinkering Day,” where one day per week for 12 weeks, up to 12 kids run through a program of literature, debate and art. The day starts with actors from the SF Shakespeare Festival helping the kids explore literature and drama together - Shakespeare intended his works to be performed, not read and dryly studied out of a textbook. After lunch a parent facilitates a classical debate class. Finally the kids explore art using iPads in a session run by teachers from a startup that specializes in teaching mobile art.

All the activities happen in the beautiful setting of a mid-peninsula park. I observed part of a session and the whole thing seemed like an idealized scene of childhood out of a movie. The parent put together the curriculum because it was something she wanted for her own kids, but she wouldn’t have wanted to hire the tutors just for her own family. As well as that being much more expensive than sharing the costs with other parents, it would have been a worse learning experience for not being a group.

Seeing this, I connected with more parents and interviewed them to find out more. A common vision of homeschooling is of kids studying alone at home and being shielded from outside influences. But that vision doesn’t fit with what I found through those interviews. All the families I spoke with had found or helped create rich group learning experiences outside of regular school and outside of the home. More like "out-of-schooling” than homeschooling. So I started calling it Outschooling for short.

As well as exploring how families Outschooled, I asked what pushed them to try it in the first place.

Why do parents choose to homeschool / outschool?

My interviews with homeschooling parents in the Bay Area uncovered the following three reasons:

     1. Normal schools can’t personalize the curriculum and so deal poorly with asynchronous learners.

Asynchronous learners are students who are gifted, but may develop at different rates in different areas. The balance may well change over time since interests / neurology changes as they grow. That sounds like all of us to an extent. It seems unlikely that most of us can progress at a range of subjects at exactly the same speed, and moreover the same speed as the curriculum is written for.

     2. Learning should be more child-led and less test-driven. Schools kill creativity.

Unschooling is an educational philosophy that roughly says children should learn by living in and interacting with the world normally rather than being contained within an artificial and prescriptive environment like school. The idea is to create self-directed, life-long learners. 

Not many parents take this to the extreme of zero learning structure, but all the parents I spoke with held this view to an extent and wanted their kids to have a less structured learning environment.

     3. Kids with special needs are poorly catered for in regular school.

Dyslexia and other learning differences, especially when combined with the child being very gifted in other ways (“twice exceptional”) make normal school an even worse fit. Large class sizes and static curriculums prevent the personalization that would be needed to give a great education for the individual. If you’re very different from other kids, not only will you suffer academically, but the social environment is also likely to be pretty terrible.

Looking at those three reasons, none seem too controversial. I think the first two would resonate with most parents. And yet homeschooling / outschooling isn’t mainstream. This is because most people have an out-dated view of what learning outside of regular school can be, and because of the practical difficulties of opting out of the current system. It was a full-time job for all the parents I spoke with.

If the outschooling alternative was better understood, and more infrastructure was in place to alleviate the practical difficulties, I think many more parents would opt out of the regular school system.

Outschooling and Future Education

Sending your kids to school today involves them attending the same institution each day in one physical location, working through a curriculum and standardized tests that are planned centrally, and years in advance. This is industrialized, mass-produced education that reflects the era in which the system was created. The curriculum aims to standardize quality, and dealing with one institution is logistically simple (relatively) for the parent who has somewhere to drop their kids off while they go to work.

But the world of the future will value individual creativity, differentiation and directly observable skills more than standardized knowledge and credentials. The future education system will have to deliver “mass customization”, and I believe this will be delivered by an ecosystem of many different institutions - much more like the outschooling I discovered interviewing parents.

Learning experiences will come in several different types:
  • In-person group activities
    • Teacher-led classes, similar to standard school classes
    • Social, interactive, broadening learning experiences e.g. park days, museum and company tours, craft workshops
  • Self-study 
    • Consuming content such as Massive Open Online Courses (MOOCs)
    • Self-directed research and experimentation
  • Online group classes in real-time, allowing for student interaction and teacher-led learning
We can expect MOOCs and online group classes to play a much larger role in the future, displacing some in-person group learning. These elements may even take up half a student's learning time, especially for older students, if the experiences of the homeschooling early-adopters are anything to go by. There are already many EdTech startups building technology and services to support this trend.

There are also startups looking to transform in-person learning through incorporating technology into the classroom. But I think the big opportunity is to look for ways to use technology to transform the existing school system, rather than just sell technology into it. We know that improved communications technology allows us to handle complex, real-time, physical world logistics (Instacart, Lyft) in a way that we couldn’t before. Online marketplaces have reduced transaction friction, increased liquidity and enable efficiency through the use of spare capacity (AirBnB, FlightCar). We can apply these capabilities to in-person group learning.

In the future I believe that we will see the school system unbundled as a marketplace of classes. 

Imagine an “Airbnb for learning activities” where parents and kids assemble custom curriculums from a mixture of institutions and individual teachers, both professional and amateur. They collaborate to crowd-fund and crowd-source activities together. Tutors may play a role, but the aim is not to create a marketplace for 1:1 tutoring - small group activities are better value and better learning experiences. Public schools would still provide classes for free in this system, but would offer them course-by-course instead of bundled.

Why now and what next?

The parents of young kids now have grown up with the internet. They have seen first-hand how fast the world has changed and how following the standard path is no longer a sure thing. They know that to be successful, their kids will need to be lifelong learners able to respond to change fast, and will need to cultivate differentiated skills. The current school system isn’t keeping pace with the new requirements and capabilities.

As a result, more will choose to opt-out of regular school and start outschooling. To accelerate this trend, new services are going to be required for:
  • Logisitics: such as transport, family calendars. How will parents and students plan their week, how will they coordinate between multiple institutions and how will kids be able to move between physical locations if they're not always in the same place?
  • Content: normal schools will eventually start offering unbundled courses, but in the short-term it's likely to be school startups, independent professionals teachers and parent / grad student amateurs who provide the activities.
  • Discovery: how will people find the activities or be recommended them, how will they be able to assess quality / suitability, how will enrollment work?

You can already see this starting to happen: Shuddle is a startup that is like Uber specifically for moving kids around between activities. QuantumCamp is a startup school offering a one-day per week science curriculum and you could imagine it become a national subject-specific brand.

Discovery is big missing piece though. There needs to be a marketplace for learning activities outside of regular school with great search, subscription for updates by subject, location etc., consistent enrollment and tools for organizers. I have started to work on this and am calling the project Outschool.

Agree with me and want to contribute? Get in touch!

Mental model for product management: a way to classify features

How do you decide what features you should build next?

A lot of startup and product management advice says that you should decide this by being obsessively focused on listening to your customers’ needs. But at the same time you shouldn’t listen to what they say literally. So how do you interpret what they say?

Here is a mental model I use for classifying features that helps me with that interpretation.

[Thanks to James Brady, Justin McKay and Kirsty Nathoo for reviewing. ]


Hygiene features make people dissatisfied with your product if you don’t have them. But will never make people love it, or even necessarily use it, no matter how many of them you build and however well you build them.

[Thanks to James Brady for ideas for examples.]

A repeating schedule feature in a calendar app would be a hygiene feature. Customers won’t appreciate your calendar because of its repeat option, no matter how well it works, but if you don’t have it you can expect a lot of complaints.

And that’s the great thing about these features: people will tell you about your product’s obvious deficiencies as they use it. They’ll come in through support tickets, your sales team, social media and user forums. If your product is targeting an existing market, you can also just look down the incumbents' feature-lists. So it’s easy to find these kind of features and justify spending time on them.

They may not be obvious from user-testing of prototypes alone though - people may not think to look for a repeat option when examining mockups of a calendar since they’re not using it for real and don’t have the same concerns as if they were actually using it for work.

If you only build this kind of feature, at best your product will be the same as all the others. 


The more performance features you have the more customers will like your product, up to a point. These “features" are often actually considerations like speed and simplicity that cut across other features.

The fewer steps it takes to deploy a new instance, the better people will like your PaaS product. The higher the camera and screen resolution is on smart phones, the better people seem to like them. Up to a point.

But it has a 100 gigapixel camera

Performance features often start life as differentiators. Someone makes a technical break-through that makes something possible that wasn’t before “Hey, we can now put a good-enough digital camera into a phone. That means people can do more with fewer devices!” An industry forms around the breakthrough, and companies compete by providing more and more of the same in each generation of the product. And they become really, really good at doing that - and sometimes not much else - which opens them up to disruption over time.

You can find these features by asking customers what they value when choosing a product in your area. And they’ll be prominently referenced on competitor’s homepages along with comparative or superlative adjectives.


Differentiators make your product dramatically better for a group of customers in ways that are difficult to replicate or non-obvious. And yet, when they’re not present, customers won’t notice the lack or tell you about them directly.

It isn’t obvious that making the photos ephemeral would be a good feature of a photo messaging app. But Snapchat has shown that feature dramatically lowers the bar for social sharing amongst teenagers.

Offering software over the internet, so customers don’t need to install it, and charging a subscription rather than up-front license, so customers only pay for what they use is clearly a better model for a lot of enterprise applications. Incumbent enterprise software companies find it incredibly hard to replicate because of their cost structure based on traditional sales - they’ve mostly had to rely on acquisitions to compete at all.

Discovering these features is hard, and this is where product management becomes creative. Famously, customers can't help you here.

     “If I had asked people what they wanted, they would have said faster horses.” - Henry Ford

So how you do discover these features? I try to think about applying learnings from one context to a different one. I try to let curiosity guide me and to purposefully explore very different ideas even if they seem crazy, or not useful, or like toys. I try to train myself to have brain that can go anywhere and to not shy away from difficult ideas.

Ultimately the only way you’ll know that you’ve correctly identified a differentiating feature is by building it and seeing if people want it. 

Thanks for reading

This is just one lens through which to view the features of your product. As with any tool you choose to use, be wary of this one’s limitations!