“If you want to build a ship, don’t drum up the people to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”
– Antoine De Saint-Exupery, author of The Little Prince

Get What You Pay For

Here’s something I’ve learned in years of running companies: people know exactly how much they’re worth. For every dollar you over-pay them, they give you back several times more in value; for every dollar you under-pay them, they find a way to stiff you by an equal margin.

Find the very best people. Then pay them very well. It’s a much easier, and much more effective, way to manage.


“A corporation is a living organism; it has to continue to shed its skin. Methods have to change. Focus has to change. Values have to change. The sum total of those changes is transformation.”
— Andrew Grove, Chairman and former CEO, Intel Corporation

I met Jess on Friendster. Which, for those of you too young to remember the web ten years ago, was at that time a successful predecessor to Facebook. Famously, Friendster turned down a sizable Google acquisition offer, as the social network market seemed wide open in those early days, and Friendster’s CEO didn’t see any serious competition.

By now, Friendster has long since been relegated to the dustbin of history, Facebook having eaten their lunch. But the object lesson remains. Being the first, or being the biggest, is often a substantial competitive advantage for a startup. But as markets mature, it’s rarely a sufficient one. Competition for customers (and for employees) means a company needs to continue to innovate, to adapt to the realities of a changing world, to find a way to continue capitalizing on that early lead. And at the same time, pressure on management (who perhaps confuse brains with a bull market in explaining their growth to date) often makes it tempting to simply double down on the exact same strategies that previously worked, this time with an increased eye towards cost-cutting to hang on to earlier margins.

I’ve been watching that happen of late to a business near and dear to my heart, though one where I’m now ill-poised to prevent what’s clearly the early stage of a slow-rolling disaster. I can already play out what’s likely to happen – stalling growth, the gradual departure of key personnel, the eventual decay of customer-base eventually leading to the company’s fixed costs collapsing the entity under its own weight. I’d love to jump in to help. And, indeed, I still might be able to find a way to do so. But there’s also the reasonable point that, in many cases, it’s just about as easy to build a Facebook from scratch as it is to keep a Friendster in its early lead, especially when a market is still young enough to have huge room for growth.

Don’t Sweater the Small Stuff

Each morning, I get out of bed, and look at the morning’s temperature. And, each morning, I have no idea what to wear as a result. Thirty-five years in, and I still have no sense at all of what different temperatures feel like, of when I should switch to long sleeves, of what ‘sweater weather’ is precisely, or of if I need to throw on a light coat. This morning, it’s 61 degrees. What do I put on?

Of course, I realize the temperature/clothing relationship is relative. In the fall, coming down from summer highs, perhaps 61 is cool enough to warrant a fleece; in the Spring, after months of snow, frost and freeze, I’d gladly head out in shorts and a t-shirt. Or consider regional differences: when my parents come in to visit from California, in weather in which I’m still wearing just a sweater, my mother has broken out scarf, gloves and hat.

Still, as with other basic skills I somehow missed early in life (cf., locating all 50 states on a map), I always feel like I should be doing something about the situation. So, in total loser style, I’m taking a ‘quantified self’ approach here, and have begun spreadsheeting the weather, what I wear and how it feels each morning after I walk Gemelli. With enough data, I might finally crack the code of what 61 degrees means, to me. And, in the process of noticing and tracking it every day, I suspect I’m far more likely to actually internalize the result.

Granted, knowing when to put on a sweater doesn’t really justify this much data-keeping; but nerdy, obsessive record-keeping comes naturally for me. You might even say it’s dyed in the wool.

On Fundraising

“I advise you to apply to all those whom you know will give something; next, to those whom you are uncertain whether they will give any thing or not, and show them the list of those who have given; and, lastly, do not neglect those who you are sure will give nothing, for in some of them you may be mistaken.” – Ben Franklin



Every morning, Gemelli and I head to Riverside Park for a walk. Before 9am, dogs are allowed off leash there, and Gem is wild with freedom. As much as he’s thrilled to explore, and to look for ladies (in human years, he’d be in his late teens, making chasing tail his primary hobby), what he really wants to do is poop in privacy.

Normally, he stays fairly close to me, rarely wandering more than a dozen feet from my side. But once we hit the Riverside Park Promenade, he takes off sprinting. A hundred feet or so ahead, he ducks behind a tree, and drops a morning deuce.

Frankly, I understand. After the embarrassment of pooping at leash’s end the rest of the day, the luxury of going solo seems well worth the effort.

Recently, however, a handful of squirrels have taken up residence in the trees above Gem’s favorite poop spot. I assume they must be harvesting the acorns, though they’ve been at it for at least a week, and I can’t imagine there are enough acorns still in the trees to sustain the effort. Nonetheless, if you’re under those trees, a regular barrage of acorns comes dropping down around you. I’m not certain that the squirrels are trying to hit you, but the proximity of the drops seems pretty suspect.

Gem seems more interested in observing the tree squirrels – occasionally barking at them, considering ways of reaching them ten feet up – than in pooping. After five minutes of chasing bouncing acorns, we move on. But it isn’t until I put his leash back on some twenty minutes later that Gem seems to realize he still needs to go.

On that final stretch of the walk, Gemelli looks at me repeatedly with a mournful expression. And then, somewhere close to home, he crouches and squeezes out an unhappy poop. He won’t make eye contact while he’s doing it, or for the rest of the walk home. Clearly, he’s been robbed the high point of his day.

To Have or to Hold

Born in ’79, right on the divide between Gen X and Gen Y, I’ve spent a fair amount of time considering the differences between the two.

One area I’ve noticed in which the two generations diverge is their desire to own stuff, rather than simply have access to it. Gen X’ers went from collecting tapes, to collecting DVDs, to collecting MP3s; like me, many I know have giant iTunes collections. Gen Y, instead, is on Rdio, Spotify and Pandora en masse, uninterested in owning any music given that they have access to all of it. Or consider car ownership – something many of my Gen X friends willingly suffer through here in NYC, but which seems nearly inconceivable to my Gen Y friends, given Zipcar, Uber and Lyft.

In the office, I’ve noticed the same thing play out in the way the two groups manage documents. The paradigm of Microsoft Word (as well as Pages and its other desktop substitutes) is one of owning docs. I make a document on my computer. I send you a copy of the doc. You make changes to that document, tracking them perhaps, then send another copy back. We can loop around endlessly, each time creating new documents, each time owning the unchanged originals on our own hard drives. But nearly all the Gen Y’ers I know vastly prefer collaborating via Google Docs. There, though I may have created a doc, I don’t actually own it; in the act of sharing and co-editing it, the document itself changes. The Gen Y’ers see this as the very point: why keep out-of-date copies at all, unsure whether the one you’re looking at reflects the most current collective thinking? Whereas Gen X’ers seem vaguely anxious about the process, unmoored without an immutable earlier version in their possession.

Going forward, apps and platforms in a slew of areas seem to be puzzling through the own vs share question. Take your photos, for example, which you might want to back up in your desktop photo library and then back up further in turn to Dropbox or Picturelife; or you might be fine tossing them directly into Facebook albums, straight from your mobile device, without a saved copy anywhere outside the social network cloud. A lot of entrepreneurs and investors are placing bets on both sides. And, in that calculus, they probably need to think more carefully about the market demographic they’re hoping to target. Because, for the balance of their respective lives, I suspect Gen X and older will think about owning in one way, and Gen Y and younger will think about sharing in another.