When he was 17, the south Londoner sold his news app Summly to Yahoo for $30m. Now his latest app Yahoo News Digest is being developed for the Apple Watch. Where did it all go right for the millionaire Oxford teenage undergraduate?

You taught yourself to code and built some apps, then sold your work to Yahoo! for $30m … easy-peasy?

We did IT at school but it was just PowerPoint and all that stuff – coding wasn’t on the curriculum. But once I started downloading iPhone apps, I began to teach myself the Objective-C coding language with the specific goal of building apps. I just saw a massive opportunity and I had lots of ideas. Every app I developed was like a learning exercise and I’d get better through trial and error.

Were you entrepreneurial at school, flogging Mars bars to your classmates?

No, I wasn’t into any of that. But when I put my first app on the App Store, it made £79 in a day. And that’s when I realised there’s a material element to this.

When you launched Summly, which led to the deal with Yahoo!, how did it feel to be compared to Larry Page, Jeff Bezos and other Silicon Valley billionaires?

I see myself as a work in progress, so there’s no point evaluating those kind of comparisons now because they don’t mean anything.

Facebook Twitter Pinterest The Summly app, which prompted the $30m deal with Yahoo

People like Ashton Kutcher, Wendi Deng and Stephen Fry became investors in your company. Did you feel nervous doing meetings and being responsible for their money?

I was nervous for my first TV interview and when I met Li Ka-shing [the Hong Kong billionaire who invested $300,000 in Summly in 2012] but I also saw that I had absolutely nothing to lose. I was making it up as I was going along, and I still am, because that’s how it works in the startup world. And so in that sense it’s liberating. And I could always go back to school … basically, this is better than homework.

The News Digest app you have created for Yahoo! builds on Trimit and Summly, your previous news summarisation apps. It provides users with 10-12 summarised news stories, twice a day. That’s quite a newspapery model?

We had three quite radical dogmas with this product. It should be twice a day and not live; it should be finite, instead of infinite streams of information; and it shouldn’t be personalised – it is definitive, so we all read the same digest. There is this visceral moment where people throw away newspapers, which was totally missing in digital. And there’s also like a wider sense of people wanting to be in the know and intelligent, and if you’re reading personalised information you can never be assured that what you’ve read is important in a wider scheme.

Facebook Twitter Pinterest Yahoo News Digest, which was created by Nick D’Aloisio.

Does that sense of completion work only for people brought up on newspapers?

To me it was very natural. It’s all about use case. I don’t mind being overwhelmed with social media because it’s addictive and exciting for different reasons but something about news consumption, I think a lot of people may see it as a chore, something they need to do and don’t necessarily want to. And so for these utility-like behaviours, it’s really good to be in and out. So the simpler you can make the experience, the better, so that’s why we constrain it.

Is the summarisation done purely by algorithms or are human beings involved?

We realised very quickly it’s optimal to have a hybrid of editorial and algorithm. The two areas for human involvement are proofreading for the coherence, because no one’s solved the problem of natural language. And the second thing is the selection of the stories in the digest because, we can’t have any false positives – if things that shouldn’t be in the digest are, people will stop trusting the service.

So do you think the summaries are improvements on the original stories? A story from a news service like AP or Reuters is already supposed to be pretty definitive and free of bias.

Even an AP story is longer than it needs to be. We’re trying to kind of take the best bits from multiple sources, and that’s quite a hard thing. We’re still learning how to do it that’s why we still rely on editorial as well as algorithm. I think that’s a real benefit. Also it’s not just a textual summary, we augment the story with atoms of information such as Wikipedia entries, Tweets, maps and links to related stories. You can assimilate more information because a lot of it is visual rather than text.

Do you see what you do as part of the “explanatory journalism” trend, like Circa or Vox?

Yeah a little bit. I think it is very educational, people are preparing for Oxbridge interviews using the app, especially PPE students. It used to be the Economist, now it’s Digest.

You’ve talked about the “pseudo-gamification of news”. What do you mean by that?

We wanted to have a reward mechanism, so there’s a motivation for reading more stories. At the moment it’s pretty low key, so as you read the stories, a little circle of check marks marks your progress. If you read all the stories you unlock a little bonus piece of content. It could be factoid or a might be a quote. We’d love to introduce some more reward elements; that’s been happening in games forever.

Isn’t it a bit depressing that you have to give people tokens to make them read more news?

We’re not paying people, we’re just giving them bits of ancillary information. Knowing that there’s something else is a good motivator, and a lot of products do that ... and it’s fun.

You’re developing News Digest for the forthcoming Apple Watch. How many words could you get on an Apple watch?

Two or three sentences at most. We’re thinking very closely about what’s the optimum length of information for a watch. Our hypothesis is that we expect there’s going to be an extremely high frequent number of sessions, hundreds and hundreds of sessions. But micro length, so like five seconds, two seconds, 10 seconds. We’re trying to think of what’s the most novel news experience you can have, that’s very much focused on the time and tempo element of the watch and the small screen. It’s amazing working with Apple on that stuff.

Facebook Twitter Pinterest Apple CEO Tim Cook speaks during the launch of the Apple Watch. Photograph: Stephen Lam/Reuters

Are the visions of AI outlined by film-makers in movies like Her pretty good guesses of where we are heading?

I think Her is a pretty good guess. Not in terms of how it ends but the stuff about a virtual assistant which has a personality and can adapt around you. I think it won’t be as great as what it is in Her, but the Siri is now a very primitive example of what it can be. My dream is an assistant who would teach me about things around me. I think that’s coming in the next 10 or 20 years.

What do you mean by that?

So as I’m sitting at this table, it’s explaining about convection currents and the heat. It’s telling you what calories are in that chocolate eclair. If you say something I don’t understand it explains what that word means. It’s aware the whole time.

Sounds like more information overload.

I guess it is but it’s relevant information. Basically it’s a virtual brain. I would love that.

So we’re 10 years from a virtual brain?

I don’t know about the singularity but I think predictive systems are getting better at determining what you want to learn or what you want to ask.

The virtual brain knows what you want before you realise it yourself?

No, but without me having to actually input “what’s the weather like”?, it can tell from sensory data that my body temperature’s changed, and therefore I might be wondering why has the change happened. So it’ll tell me that the weather’s just dropped or whatever. There’s a lot of things you can do with prediction based on the sensory stuff. The Apple Watch is a great example of prediction through biometrics.

Elon Musk and Stephen Hawking have made alarming predictions about AI…

I think they’re overestimating the power of it. When I say virtual, I do not think there’ll be a sentient cognitive brain that’s as good as a human. In specific domains the AI will get very strong. But this kind of generalist view that it’s going to be a brain as good as a human being – that’s almost impossible to see happening.

What are the technical barriers to doing that?

A lot of it is around learning. It’s easy to teach a computer how to recognise a mug or something, because you send it lots of information and it can build its own image of what a mug is. That’s possible because it’s a physical object ground in the physical world. But if you try and teach it an abstract concept, like God, how do you even begin to do that? Because a lot of what God is is grounded in what people’s own weird conceptions are, which are continuing to morph over time. It means something different to everyone. No one knows how to ground these very high level abstract concepts in a machine.

Don’t you think AI could be dangerous in fields such as warfare?

Obviously I think any automated technology has got potential danger but human error is worse.

So would you rather be a passenger on an aeroplane piloted by a human or by a robot?

I’d want both, I would want a hybrid. Not one or the other.

I imagine you’re looking forward to completing your computer science and philosophy degree so you can move to the Valley full-time?

I’m not at Oxford for the degree. It’s more just environment, you’re meeting others, really intelligent people who have completely different interests. And what I find refreshing at Oxford, compared to somewhere like Stanford, is that computer science is seen as very theoretical or mathematical, it’s not seen as entrepreneurial. In the Valley everyone cares about making money; at Oxford they’re the opposite.

What will be an important trend in 2015?

Anonymity’s back in fashion – which is very much like the original web. A lot of people are scared of giving away their data, they want to go back to a very basic form of the internet. Similarly people are getting bored of streams of information and personalisation and they want to go back to simpler user interfaces. So products that are distilling and simplifying are going in the right way.

If users are withholding their valuable data what’s the business model?

It’s a great point. They’re going to have to come up with new ideas. But I think there needs to be an overhaul in monetisation, the advertising model is getting old, people don’t want to opt in. And ads are difficult to do on smaller screens, so they’re going to have to re-think the model now.

Could you summarise this interview with your software?

Algorithmically, it would be quite possible because there’s a question and answer structure. The algorithm could begin to look at the first few sentences of each answer, and trying to tell them which are most important. But I wouldn’t want to summarise an interview in that way. I would think it’s better the human does it. In the end it’s like there’s no point in doing AI for the sake of AI, it’s only when there’s a practical need. In the case of news information, because there’s such an abundance of articles, so much redundant duplication, it doesn’t make sense for humans to be paid to sift through it all, because you can do it algorithmically. In the case of a Q&A, because they are rarer and because the person who’s conducting it is a human, it makes more sense to have an editor who’s human.