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 Trigger.io - 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 outschool.com 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?