I’ve made a career of working far from where I live. I’ve generally considered this a significant pain – there are disadvantages and inefficiencies in being geographically separated from coworkers. Hence I’ve endured horrible commutes and frequent travel.

Lately, however, I’ve been reconsidering. My office is about 30 minutes from my house, but I end up not going in more and more these days. The 1 hour roundtrip is simply wasted time, and the traditional 9-5 is an artificial constraint on both work and non-work activities.

The turning point, not surprisingly, was technology driven – earlier this year I was working on a shared presentation and document with 2 colleagues. We met in person twice, and the third time we used Google Wave (rip) for shared document editing and iChat for voice and video communication.

I was shocked at how much more efficient the third session was. I despise video calls, but in this case it was background, mainly to see who was paying attention and who was tuned out. The shared document with real-time edits worked fabulously well – one could write stream of consciousness thoughts, and before finishing the paragraph have his work edited and polished by the other two.

These days I find my most efficient working relationships require little in-person interaction. What they do require is a host of enabling technologies we take for granted.

I’m still a huge believer in the value of in-person interactions – the best ideas generally pop up over lunch or other informal settings. But in-person interaction doesn’t require the traditional office setting and trappings.

The work style adopted by startups today will make its way to large business, and the services that are the lifeline of that style will become the dial-tone of business. As Paul points out this will drive the creation of a number of significant companies to provide those dial-tones. And with any luck I’ll have an opportunity to invest if a few of them

We have to let go of this notion that for [us] to win, [our purported competitor] has to lose. We have to embrace the notion that for [us] to win, [we] have to do a really good job. And if others are going to help us, that’s great. Because we need all the help we can get. And if we screw up and do not do a good job, it is not somebody else’s fault, it is our fault.

His blog is fantastic, and I quite often agree with his advice.

That’s why I found it odd that his The Best Entrepreneurs Are Hyper Competitive & Hate Losing struck such a dissonant chord with me.

Shuffling through the successful business people I know and trying to gauge whether they would be the type of people who are obsessed with winning, even in a family game of scrabble, I don’t come to a clear conclusion. I know hyper competitive people, but I also know plenty of people who are able to separate their business behavior from their personal behavior. And not obsess with beating the competition.

Maybe that’s what’s not sitting well with me – Mark’s definition of winning seems to be beating the competition.

Some of the best entrepreneurs I know don’t obsess with the competition. They obsess with their own behavior.

Here’s a contrived example – look at Apple. Do you see Jobs competing with the others in the industries he enters, or do you see him trying create the best possible product, distinctly separate from what his competitors are doing?

Frankly I have a hard time picturing a lot of these guys stressing out over scrabble or Guitar Hero.

Mark’s a very successful guy and his approach has certainly worked for him, but I disagree that you need to be obsessed with winning in the way that Mark describes it.

Look at this way: you could destroy all your competitors and still not win. You could also win without destroying any of your competitors.

First, pick the right game. Then, pay attention to playing that game as best it can be played. Competing may be an important tactical part of playing the game, but it’s probably not the part to obsess over.

First, I think Google actually does want the web to be faster and better. They recognize that the web is their platform and any improvement to it has an eventual benefit for them.

But Google DNS also provides other benefits. It’s true that there is an advertising opportunity in hijacking mis-typed domains and displaying ads against them, as OpenDNS does. This is potentially a large market – domain squatters, for example, make a tidy living doing something similar. I don’t think Google will actually do this. At least not anytime soon – it’d just be too creepy coming from Google.

What Google is really after is data. In particular, traffic and usage data.

By using Google DNS you effectively tell Google exactly what sites you’re visiting, when. Google gets access to your browsing patterns without having to install a toolbar or spyware on your computer.

How valuable would usage data be to Google? Knowing exactly what sites you visited, when, and how frequently?

Extremely valuable. They could use this information to develop refined models of your interests and behavior, and use it to better target ads to you. Nice.

However, their privacy policy states that they won’t do this.

What they will do is use the data to form a better model of the web.  They’ll know, for example, how popular sites really are and how much traffic they get. They’ll also be able to build user and browsing pattern models – eg. people who use facebook are also likely to use sites X, Y, and Z. They’ll use this data to improve search and advertising.

Look for Google to start offering its DNS services for free to internet provides, corporations, or anybody else with large amounts of users. Instead of paying ISPs for access to their usage logs, now they can get their own, and it’ll only cost them the overhead of running a large scale DNS service.

Peter Norvig’s message has been that more data trumps better algorithms. Google DNS is a beautiful way for Google to get a tremendous amount of data with very little intrusion while looking (and behaving) like saints.

First step is to look up the person on the web. Since I’m looking for a technical person I’m expecting a blog, contributions to open source projects, a twitter presence, etc. If I don’t find them, the candidate becomes less attractive.

If I do find a blog or twitter feed, I take some time to read them. You can tell a lot about a person with just a short overview – for example, even a delicious feed can give you a very good feel for how good someone is technically.

Hopefully the person has an open source project or two they’ve contributed. If so you can dive right into the code and get a good sense of their skills at work. I love this – you can see great coders almost immediately. And of course bad ones.

If the person is still looking good it’s time for a review of the resume and their linkedin profile.

By the time I followup with the person I have a very good sense of who this person is, what they’ve done in the past, and what their real-world coding looks like. The people who make it to the interview are so well filtered you almost can’t go wrong.

It’s very time consuming, but if you’re as fanatical about hiring good people as I am it’s worth it.

Contrast this with the old pile-o-resumes approach, or the recruiter-filter-by-keyword approach, and I think we’re in a much better place.

Now if I could only find a recruiter I could trust to do the technical deep dive I’ve described here and be ingenious enough to find diamonds in the rough I’d be a very happy man.

Why is it disturbing?

It’s important to understand that Google doesn’t directly make money on email. Think of it as a loss-leader of sorts.

Yes, I know there’s advertising on there. I also know a bit about advertising systems.

Gmail brings in a relatively a much smaller amount of revenue than Adwords and Adsense, and the margins are much lower. You have to pay for all that Gmail infrastructure, and click-thru rates on email ads (or ads placed next to most other compelling content) are very low.

Google is smart enough to know where their money comes from, and they go to great pains to ensure their search remains superior. They invest a lot in search.

But what do you do with properties that make money, but at small amounts and with much lower margins?

For example, Yahoo Finance, Small Business, My Yahoo, and many of the other businesses are nice, profitable business, but not large enough or high-margin enough to get a lot of love or resources.

You neglect them. You put resources on projects that move the top or the bottom line.

My concern with Gmail is the trend that looks like neglect. It’s a relatively large property for Google, but it’s been experiencing problems. I know fail happens, but I also know that if Google put their mind to it they could make it much more available than it has been.

As Google branches out into more new and different products, it needs to be very mindful of neglect. Rot at the edges of your systems deteriorate the overall perception of your offerings. And search market share is very dependent on perception: witness the studies that removed branding from Google, Yahoo, and Microsoft search results and found nearly identical user satisfaction scores. 

So Google’s outlook has to be: if we’re going to do something we’re going to do it extremely well. The apple philosophy.

And if we’re not doing something extremely well, we need to fix it or shut it down. 

It’s a tough balance – how do you foster innovation and allow people to quickly create and launch projects, while maintaining a commitment to long term maintenance of quality?

It’s crucial to identify your core offerings, mark the rest as alpha, beta, “labs”, or any other label that signals the service might go away, and be absolutely fanatical about the quality of the core offerings on a continuous basis.

Here’s hoping Gmail gets its act together so I don’t once again have to switch providers.

What most people don’t know is that Britannica was actually a tremendous innovator early in the days of the Web. Harold Kester, a very smart guy, a good friend, and later CTO of Websense, ran the advanced technology group here in San Diego. His team was smart enough to spot the importance of the Web very very early (we’re talking NCSA mosaic days, before Netscape existed), and make fantastic advances, particularly in the field of search. I was lucky enough to work with them.

Unfortunately Britannica’s core business, selling encyclopedias door-to-door, was getting killed by this CD based encyclopedia from Microsoft called Encarta. Who would pay over a thousand dollars for something you could get practically free?

Britannica’s business model didn’t survive the age of the CD, but the company did manage to transform itself and leap to the next technology, the Web.

Then it ran into this thing called Wikipedia.

All of this nostalgia is stirred up on reading that Microsoft has decided to close down the Encarta business. A technology and model that killed a long-running, well established business itself killed by a newer, shiner model.

A little while ago I left Yahoo! to go full time on yet another startup, Xpenser. Xpenser is expense tracking and management simplified: record and manage your expenses from any device, any time. As soon as you get out of the taxi, call and say “Taxi $27 office to San Jose airport”. Your expense is recorded and you can forget about it.

Or you can email “Lunch $35.13 with Jack”. Or SMS it. Or iPhone it. IM it (Yahoo, AIM, MSN, GTalk). Twitter it. Use the browser search box. The FireFox plugin. Or, believe it or not, the Web.

As you can imagine this was born of personal need – I travel a lot, and expense reports have been the bane of my life for as long as I’ve worked.

Xpenser is an expense management tool built by someone who hates wasting time on expense reports.

The site has been growing wonderfully, with a bit overy 20k users, and in Nov/Dec was featured in Consumerist, Mashable, Lifehacker, Stepcase Lifehack, BNet, and even briefly in the Motley fool. The users are passionate, the feedback is great, and all the metrics are off the charts. 

In short, it was an obvious move.

My 4 years at Yahoo! were fantastic – I was fortunate enough to work on make-or-break projects with a group of very smart, very dedicated people. I learned a lot, am very thankful, and continue to root for Yahoo! to make its way back to the top. Keep fighting guys!

So, back to the startup world for me, and I couldn’t be more excited. I’m also advising a few other startups and investors here and there, so I’m fully in it. This is actually a fantastic time to do a startup if you’re planning to build a real business.

Needless to say, if you see opportunities for Xpenser in your network, do let me know ( parand at xpenser dot com ). And if you’re around San Diego or LA drop me a line and we’ll grab coffee and catch up.

2009 here we come!!!