Before David Sifry, who spoke at the WIT Conference, founded Offbeat Guides, which brought him into the travel industry, he planted the seed that became Technorati, the blog search engine. He was also on the founding board of Linux International and a technical advisor to the National Cybercrime Training Partnership for law enforcement. 

Offstage, WIT caught up with David Sifry to talk about the hidden dangers of the growing social web, his concerns about growing patent applications by companies like Google and Apple and why open standards are the way to go. Imagine a “wikipedia for places” and oh yes, Offbeat Guides in Chinese.

Q: In your 20 years in the IT industry, would you say this is the most exciting time to be alive (as it were)? If so, why? If not, which was the most exciting time?

It’s a marvelous time to be alive, and to be working in the IT Industry. I think the opportunities are nearly endless, and there has never been a time when technology has been in the hands of more people, which means that the opportunities to make people’s lives better couldn’t be bigger.

Q: What are the opportunities and perils of the growing social web?

First off, you’ve got to recognize that what you thought was private is now public, or can be made public with one click. Marshall McLuhan spoke about the “global village” also meaning that it would be a gossipy village. I think a lot of people are learning in real-time how to build and manage an image of themselves with social media.

What this means is that the opportunity to completely reinvent yourself goes away – we’ve got a web now is both personal and that has history, and I suppose that’s both a good thing and a bad thing. What happens now that everyone’s famous for 15 minutes? What do you put online, and what happens when the moments formerly thought of as private now can become public at the click of a smartphone camera shutter?

Does this inspire independence, or conformism? Does it inspire self empowerment or self aggrandizement? Maybe it is some of both, but I worry about the increase in information overload and how that provides incentive to people who are willing to be more and more outrageous and polarized. Is this better than mass media today? Are people’s perceptions warped because of the self-aggrandizement?

I have a strong faith that when we give people the opportunity to have a voice and to get their voice heard, that it is enormously powerful, and provides a incredibly democratizing force in the world. What I worry about is the amount of unintentional disclosure that happens as people live their lives more and more on the web, and we trust only that companies will “do the right thing” when it comes to the aggregated information that people publish about themselves.

I’m actually quite optimistic about social media – but I worry that we aren’t thinking carefully about what we’re giving away when we make so much of our lives public.

Q: Given your background in Open Source Development, what are the good things that are happening, and the bad stuff that’s out there?

I’m really encouraged by the growth of open source and open standards out there – so much of the web just simply wouldn’t be possible without the technology sharing that has occurred with open source software – Linux, Apache, MySQL, Ruby, Perl, Python, PHP, Memcache, Hadoop, the list goes on and on. And what is encouraging is that the leading companies are continuing to contribute and give back to the movement.

The next frontier is around Open Data. For example, no one has perfected an open “wikipedia for places” yet. Some folks are working on creating open maps, which is fantastic but for example, we don’t really have an open identifier system for location information. Right now, we’ve got a few really large data providers, and getting all of that data and keeping it updated is very expensive.

I’m also a big believer in Creative Commons licensing and in the growth of user-generated content and users becoming authorities. We use a lot of Creative Commons-licensed information in our guidebooks to help keep them up-to-date and as comprehensive as possible.

4. What are your thoughts as an entrepreneur on the actions of companies such as Google and Apple (latest being to patent mobile travel apps)?

Overall, I have tremendous respect for Google and Apple, and they employ incredibly intelligent, ambitious, and hardworking people. There’s an enormous amount of innovation coming out of large companies like them. But I’m quite concerned about the proliferation of software patents, especially at their breadth and obviousness.

The issue is that at least in the United States, there isn’t enough funding to make sure that really qualified patent examiners have enough time to do the research into obviousness and breadth of the patents that are filed. This ends up becoming anti-competitive, and stifles the market.

I think we need to remember why the idea of patents were created in the first place – they are there in order to provide incentive for innovation. But in the world of software, the costs are so low and the rewards are so potentially great, I don’t think we suffer from an investment problem in innovation, so I think that software patents are, by and large, a bad idea. Unfortunately, because it is the way the world works today, companies feel the need to reach for as large a patent portfolio as possible, even if it is purely defensive. This actually acts as an innovation tax.

Q: What’s the hardest thing about being an entrepreneur – starting up, maintaining or doing the exit? With Technorati, what was the experience like?

I think the hardest part is figuring out if you’re really doing the right thing. Life is short, and starting a business is always an incredibly expensive thing – if not always in cash, it is certainly expensive in time, and in terms of opportunity cost – in other words, what you’re choosing not to do.

I’m also a person who really really hates to lose, and who hates to quit. But sometimes you’ve got to walk away from a market, or walk away from a product you love. Those decisions are always the hardest for me.

I’m lucky in that I just love getting businesses started, building the first products, finding great teams who believe in the vision, and inspiring them to go beyond the original idea and make it a shared vision. When I started Technorati, I built it because I just wanted to know whenever anyone, anywhere in the world, talked about me.

What it has morphed into, first as a search engine for blogs, and then as an advertising network for social media, is way beyond my original vision, and the success we’ve had is really a testament to the team and what they’ve built – it’s not about my personal vision any more – they really deserve all the kudos and credit.

Q: Tell us about your latest start-up, Offbeat Guides? What gave you the idea? What pain are you trying to solve?

Offbeat Guides is a company that builds up-to-date personalized travel guides for over 30,000 cities around the world. We put in just the information that you want, about just the places you’re visiting, and add in events, festivals, and all the interesting things that are going on during the dates of your trip.

I started it in 2008, and it came out of a core problem that I had – I was traveling a lot, both for business and for pleasure, and I found it incredibly difficult and frustrating to put together a trip plan that was tuned to my trip and to my interests.

There’s actually a lot of information out there on the internet, but it’s just incredibly hard to ferret out the good from the bad, the reliable from the unreliable, and then put it in a format that is easy to use when I’m actually on the trip. So, I created Offbeat Guides originally to scratch my own itch – to give me a good travel guide that I could customize, to keep it automatically updated, and to make it so that I could get it on the go.

We’ve found that a lot of people also have the same problems, and because of that Offbeat Guides has been quite successful. It’s fun!

One of the best parts of it for me has been to see what other people have done with it, especially as we’ve opened up our API for outside companies at http://apiwiki.offbeatguides.com/

Having the opportunity to get integrated with big OTAs like Expedia and fantastic companies like Starwood and their Preferred Guest program has been wonderful. I think there’s a lot of creative opportunities to provide airlines, hotels, OTAs, and other companies with a compelling value for their customers – and there’s a lot of ways to make money with them at the same time as you’re providing a unique service to their customers.

Q: Someone once said, content wants to be free. But now it seems, content needs to be tamed? What’s your view on where content is headed?

I think the original quite was “Information wants to be free. Information also wants to be expensive, too.” I think that a lot of people miss the second part of that quote. But the reality is that for most information, there’s just an incredible glut of information supply. There’s a real need for a trusted agent to curate and make recommendations on what information has value. In that sense, you’re not really paying for information itself. What you’re paying for is a whole lot of saved time, and you’re paying for the convenience of getting it when you want it, how you want it.

Q: What implications will devices such as the iPad have for content creation and content delivery? The Flipboard for example has tremendous application for travel, don’t you think?

Yes, I agree. But I’m not so sure that tablets will have as much of an effect while you’re on your trip as they do when you’re still planning or figuring out where to go. A lot of people who purchase traditional travel guides are armchair travelers – they want to enjoy the fantasy of going on that around-the-world trip to exotic places for the price of going out to dinner. And that’s a very valuable place where the “sitting back” experience of a tablet like the iPad gets you. I think that combining that with more dynamic mobile experiences while you’re on your trip make a hugely powerful combination.

Q: You have worked in Japan. What’s your view on the digital media scene in Asia? And will we see you move into this region with Offbeat Guides?

There’s been a huge burst in local innovation over the last 20 years all across Asia, not just in Japan. In a lot of ways, us folks in the US are learning how to do mobile right by looking at Japan, Korea, China, and the other countries in the region, and the growth of virtual goods, for example, was really pioneered en masse in Asia, and then made its way back to the USA.

I think that one of the issues that we see with Offbeat Guides is that for the last few years, we’ve really been focusing on building high quality guides in English, because that’s where we can currently ensure high quality control. But I think that China, in particular, is going to see a huge boom in tourism outside of China, and we’re actively looking at partnerships with companies that can benefit from our search and packaging technology and combine it with great local expertise in content.

Featured image credit (Computer and internet icons seamless pattern): Ockra/iStock