Backed By Angels, SiteSimon Launches To Turn Your Browser Into An Intelligent Assistant

When New York-based SiteSimon first emerged from Entrepreneur Roundtable’s accelerator program last year, it was as a social browsing tool that aimed to automate the process of finding and discovering personally relevant content on the Web — not unlike StumbleUpon. A good idea, to be sure, but co-founder Steven Gutentag tells us that, in fact, users were less interested in new destinations than they were in finding better ways to filter and discover content from sites they’re already visiting.

The team listened to its users and is today announcing a pivot and re-launch of SiteSimon, which sees the startup turning its full attention to the browser. SiteSimon is, for now at least, a Chrome extension that seeks to transform your browser into an intelligent assistant, locating the content that it has deduced will be most relevant to you — in near realtime, within whatever site you happen to be visiting.

Right now, SiteSimon is Chrome-only, and Gutentag tells us that the team is focused on building an awesome product, focusing on Chrome due to its traction among early adopters and its (comparatively) stellar developer tools. The team wants to build comparable add-ons for Firefox and Safari, but only if and when the Chrome extension is in fighting shape.

So how does it work? The extension integrates with Chrome and crawls your browsing history, learning as it goes, identifying patterns in your clicks, and directs you right to the content it thinks you would find interesting and relevant. “We are trying to create an interest graph for the user,” Gutentag says, in that, as you surf through TechCrunch content, for example, SiteSimon pulls in data as pages load, parsing data and analyzing metadata, titles, and keywords, before serving you relevant suggestions.

These relevant suggestions appear in a sliding sidebar — and this is what’s really cool — the team is trying to reduce the annoyance factor, so that it will only make recommendations if it has ones it thinks you’ll like. If there aren’t any good recommendations, the sidebar won’t appear on the site. If you click on its recommendations, the extension gets smarter.

And, for those who have recently cleared their browsing history, you can import your history from Chrome and set SiteSimon on its way. Generally speaking, it only takes a few minutes before it’s recommending you content, although there are exceptions, something the team is working on.

Of course, news sites tend to be far richer when it comes to metadata, which means that it’s recommendations really shine on content sites, blogs, and the like, but it still works for others, like Yelp and YouTube, for example. As it’s powered by learning algorithms, SiteSimon tends to work better if you have a lengthy browsing history. I do on Chrome, and it’s been working like a charm.

Some might say that it’s not worth spending the time it takes to train the extension to know what you like and what you don’t like, but that’s the thing — once you download the extension, it lives in the background and gets smarter just by hoovering up all the activity from your browser. It analyzes keywords and patterns in your browsing, the frequency, how long you spend on the site, and then offers three recommendations for you — no categories, no overloading you, just the three best recs.

You can think of it like the personalized results TechCrunch had in its side bar alongside Trending Posts for awhile, or for those who’ve visited Business Insider, a less annoying version of those pop-up recommendations that appear at the bottom of the page. The team likens it to an intelligent personal assistant for your browser.

And considering Google and others are busy collecting and using your history for their own purposes, whether nefariously or not, SiteSimon wants you to take back control of your browsing data, insofar as that goes. And, to that point, Gutentag stresses the fact that the extension “discreetly” analyzes your browsing patterns — just as any app or extension that pokes around in your browsing history should.

While it may sound creepy, the service is completely secure, 100 percent private, and automatically turns off on any personal sites. Once you’ve signed up for a free account, you can go to “Settings” and type in the sites you don’t want SiteSimon touching, although it already filters out all “https” secure domains and adult content.

Again, the extension is still in the early phases, but the concept is appealing. If you’re on a large content site, like TC or ESPN, it’ll recommend new articles, or if you’re on Yelp or Seamless, new restaurants. Best Buy … products. Brands and sites, if they’re paying attention, could get behind the idea, because it doesn’t take you off site, it finds what you want and personalizes your experience once you get there.

In my eyes, Google is already using bits and pieces of your Chrome activity to personalize your experience, some transparently, and some likely not. So, if you’re going to have all this data sitting there collecting, why not have a relatively noninvasive, smart recommendation tool that travels with you as you go?

At this point, SiteSimon isn’t focused on monetizing, just on building its user base and honing its technology. But, in the end, this is the type of tool that every browser could benefit from integrating right out of the box, and you can see why that’s in the back of Gutentag’s head. Right now, it still has a ways to go before it’s ready. It needs to offer an easier way to shuffle recommendations. If it keeps serving the same three, press a button and move on. Makes sense, right? And learning can be slow. It’s still evolving, but the concept here is sound, and with some help, this could be a really valuable tool.

Last year, SiteSimon raised $500K from angel investors, which included contributions from Ken Cron, the former CEO of Vivendi Universal Games and former president of CMP Media, John Ason, an early investor in,, and, as well as and Zeel co-founder Samer Hamadeh. The startup will likely begin going after more capital this summer.

What do you think?

For more, check out SiteSimon at home here.