The problem with choosing the size and shape of an electronic device – what’s commonly called ‘form factor’ – is that it’s inevitably an act of compromise. Make something big enough for a keyboard and sizeable screen, for example, and it’s too big to pocket. Make it little enough to cart around, and there’s simply not enough space to squeeze in a keyboard and resonably-sized display.

Some devices – iPhones or tablets – try and work their way around the problem by faking one element for another: the screen doubles as the keyboard and the mouse. Others – like the new Droid, with its slide-out keyboard – approach the problem like origami, looking to tuck elements behind each other when not in use.

And, invariably, those approaches suck. Another approach – voice recognition – sucks, too. But it sucks in different and complementary enough ways that, when paired with the indigenous suckiness of a device’s design, it often hugely improves the overall experience.

That’s certainly the case with Dragon Dictation, a new app for the iPhone. The idea is simple: you speak into the iPhone, and, within a second or two, the phone uploads the data, transcribes it to text, then displays it on your phone. You can use the iPhone’s software keyboard to tweak any mistakes, though, to my surprise, the accuracy of the translation, even in noisy settings, is surprisingly good. Then, with the touch of a button, you can transfer the transcribed text to an email, text message, or to the clipboard for pasting somewhere else.

For the first time, I can now enter an entire email’s worth of content in less than ten minutes of laborious thumbing.

Which isn’t to say that voice transcription will be replacing my laptop keyboard any time soon. While the human ear scrubs out the ‘ers’, ‘uhms’, and non-grammatical structures that populate at least my own speech, Dragon isn’t nearly so kind. And, similarly, while conversational speech tends to move only forward, typing is usually full of long pauses, and even regressions, moving backwards to edit prior fragments.

The writing I can do with text-to-speech, then, is well less than perfect. But, as compared to what I can accomplish with the iPhone’s keyboard, it’s an improvement nearly impossible to overstate. And, at the moment at least, the price is right: download it for the introductory $0 price, and give it a whirl yourself.

[Nota bene: You may see a lot of negative reviews on the iTunes site, mainly from people unhappy that the app uploads the names of your contacts to the Dragon servers. I suspect this is a tempest in a teapot, as Dragon uploads only the names, not any further info like emails or telephone numbers. If you have a Facebook account, you’ve already given up way more information to a company that’s repeatedly proved itself to be way less competent in respecting privacy concerns. In the end, it turns out most people are willing to give up a little privacy for a lot of functionality – Dragon can spell the names of your friends and colleagues right if it has a list to help educate guesses – and for most people that’s a reasonable trade.]

[Another of my VC newsletters from 1999, this one waxing on about a piece of technology I’d just picked up at the Consumer Electronics Show in Las Vegas: a RIM 850, the very first Blackberry.

Using it around New York, the response from my friends at investment banks, hedge funds, and law firms was unanimous: clearly, nobody outside of the world of high tech would ever, ever carry something like that.]

Yesterday, I received about two hundred email messages. To most normal people, that seems like an ungodly number. But from many people involved in internet businesses, the response is “yeah, that’s about right,” or “only two hundred?” Of those two hundred, three were spam and about twenty were newsletters and other updates. But at least half required some sort of timely response.

Regardless of the number, email has become central to my way of business. And most people that I talk with say the same thing. Many executives of internet firms even prefer sending email over talking on the phone. The difficulty, however, is that phones are available to executives on the go; email, by and large, isn’t.

I recently, however, discovered a solution: the RIM 850. About the size of a standard 2-way pager, the RIM sports a slightly larger than usual screen and a tiny Qwerty keyboard. But packed into the small black gadget is a lot of functionality. The RIM is a PDA, sends and receives email, and browses the web.

While the PDA is fairly simple, it does everything I need. And despite the keyboard’s small size, typing emails by thumb is surprisingly fast and comfortable. Unlike the Palm VII, coverage is nationwide, and because the 850 runs on a pager network, building penetration is quite good. The 850 is also better than the Palm VII for three other reasons. First, the 850 can check your existing POP account, instead of requiring a special yourname@palm.net address. Second, the 850 checks mail continually, and, like a pager, notifies you instantly, by tone or vibration, when you receive new mail. Third, the 850 is priced on a flat fee, equal to the Palm VII’s second cheapest plan. My two hundred messages would more than burn through an entire month’s worth of the Palm’s top plan in less than a day.

The little web browser is also surprisingly good. The GoWeb browser strips everything but text from pages and then compresses them for faster transmission. You can check headlines, stock prices and sports scores, get driving directions, and even search the yellow pages from the palm of your hand.

The best part, however, is that, by your instant responses, you appear to be a workaholic. You seem to always be waiting by your computer, when, in fact, you could be anywhere at all. Which is why I was glad to see that the RIM network has full coverage throughout Hawaii.

[My old Sharkbyte partner, David Fischer, recently emailed to say that one of his current tech companies is launching a newsletter, and to ask if I’d saved any of the similar newsletters I wrote back in my tech VC days for inspiration.

Indeed I had. As my ‘bleeding edge’ thinking from 1999 now seems painfully quaint, I thought I’d reprint a few of the editions here over the next few days. First up: the inside scoop on a brand new search engine, Google.]

When users open their browsers, they’re largely doing it to gather news and information. In fact, according to recent research by e-Stats, 87.8% of users engage in information gathering, while around 80% are involved in the loosely related activities of research or surfing. The next categories, like online gaming, chat, and shopping are considerably less popular – 30% or less of web users engage in them.

The common thread in the top three activities – information gathering, research and surfing – is a need for search. Users start out with a vague idea of what they’re looking for, and usually (about 85% of the time) they head straight to a search engine to find what they want. Most of those searchers head to Yahoo, others to Excite or Lycos, while particularly web savvy searchers sometimes head to Metacrawler, which aggregates the results of the top search engines. All of these searches, however, have the same shortcoming – they only search based upon the “relevance” of the page – in essence, the number of times your search terms appears on the page.

Enter Google. Google, along with relevance, uses quality in rating pages. A Google search, then, doesn’t just give you some pages that contain your search terms – it gives you the best pages that contain your search terms. Of course, the web is much too large to rate every page for quality, so Google uses a fairly clever strategy – start with a collection of quality web sites, and define a quality site as one linked to by other quality sites. It might sound circular, but the results are surprising. They’re so good, in fact, that Google has an “I’m feeling lucky” button which takes you directly to the first search result. The algorithm works so well that the first result actually has the information you need the vast majority of the time.

No, we don’t own a stake in Google. But we do watch the web very closely – that’s our job. After seeing how many of our friends still use older search engines, we decided to pass on what we’ve learned. It just might save you a bit of time and sanity.

I enjoy immensely the large number of TV commercials explaining that television is going all-digital at the end of the year, which refer anyone with an analog-only TV and no converter box to various web sites for more information.

Because, really, the vast majority of people with antique bunny-eared black-and-white TVs also have computers with fast broadband connections right nearby.

“IF U LOVE ME AS I LOVE U
THEN I & U WILL MAKE 1 OF 2”

This quotes is:

1. A text message.

2. A Prince lyric.

3. A verse by Vermont’s Ebenezer White, written in 1782, as a marriage proposal to Lucy Packard, his future bride.

Yes, number three it is.

Which seems to me a reasonable counterpoint to all of this ‘IM and text shorthand is killing the English language’ alarmism.

Turns out, we’re not nearly as original or influential as we’d like to think.

While Will Hunting may think an Ivy League degree is “$150,000 wasted on an education you coulda got for a buck fifty in late charges at the public library,” it turns out, he’s wrong. By now, in fact, you don’t even need the buck fifty. Because as of a few months back, Yale has put a handful of its best-loved courses online.

I’ve been taking advantage myself for the past week or two, downloading sessions of RLST 145 – Introduction to the Old Testament – to my iPhone, and listening on my way to work. But there are several others that look good, too, and two classes that I can highly recommend from past experience: PHIL 176 – Death, with Professor Shelly Kagan – which I much enjoyed my sophomore year, and PSYC 110 – Introduction to Psychology – a great survey course now taught by Paul Bloom, my favorite professor of any at Yale.

Extended warranties are a crock of shit.

Sure, short-term warranties make sense, protecting you from manufacturing defects that appear only after a few weeks of use.

But any product used longer before needing an initial repair is invariably just hitting the first of many stops along the slow and painful road to total malfunction and breakdown.

I say this based not just on past experience, but on current. Because, in the last six months, my MacBook Pro had had its logic board, video RAM, left fan, right fan, hard drive, and display replaced. Essentially, the only thing I have left of the original computer is the chassis and keyboard. And, still, the damn thing crashes every ten minutes.

By now, the time wasted waiting for each of those restarts has added up to hours of lost work worth many times over the cost of a new computer. But with AppleCare extended warranty in hand, I’ve been loath to give up completely.

As my computer has frozen twice while drafting even this short posting, however, I think I’m finally biting the bullet and upgrading. Or, rather, cross-grading, as I’ll be replacing the MacBook Pro with an essentially identical (albeit 0.2GHZ faster) MacBook Pro. Some of us never learn.

“The ship wherein Theseus and the youth of Athens returned [from Crete] had thirty oars, and was preserved by the Athenians down even to the time of Demetrius Phalereus, for they took away the old planks as they decayed, putting in new and stronger timber in their place, insomuch that this ship became a standing example among the philosophers, for the logical question of things that grow; one side holding that the ship remained the same, and the other contending that it was not the same.”
– Plutarch

Yesterday afternoon, I picked up my laptop from Tekserve, after it had spent a week at Apple Service Headquarters.

Or rather, I picked up a laptop. Because, while the shell was still original, the logic board, video RAM, left and right fan, hard drive and screen had all been replaced.

Still, mine or not, for the first time in months, at least the damn thing works.