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.


A bit more than a year ago, I recommended Mailbox as the best iPhone email app. But while many of my younger colleagues use their phones as their primary email devices, I send nearly all of my emails from my Mac. So I’ve used Mailbox mainly for triage, and less for actual communications.

Last week, Mailbox started rolling out a beta of their OS X desktop app. Like the sadly defunct Sparrow, it’s minimalist in style, and blazingly fast. It also lines up well with how I use email – an emphasis on reaching ‘inbox zero’, and on archiving / searching rather than filing.

Like the mobile app, Mailbox on desktop allows you to ‘snooze’ messages, pushing them out of your inbox to reappear at a time you can actually reply to or act on them. And like the mobile app, Mailbox on desktop badges the total number of messages in your inbox, not just those unread.

I’ve previously found that changing email apps changes my emailing behavior. Using OS X’s built-in, for example, causes me to let email backlogs pile up far more than checking the same email directly in Gmail. And, for reasons I’m still not entirely clear on, Mailbox is, in turn, even more effective for me than the Gmail site for staying on top of my inbox.

On the chance it works equally well for you, go check out Mailbox on OS X.

(A final note: as Mailbox is currently rolling out their beta, you’ll need to sign up to receive a ‘betacoin’ to activate the app. I have a handful of betacoins, so ping me if you’d like one.)


A few months ago, one of our upstairs neighbors told us a story about a dog who lived in our building thirty or forty years back; I didn’t believe it, until another of our upstairs neighbors told us the same thing, and told us that it was her dog.

Apparently, when her Yorkshire Terrier needed to go for a walk, she’d call the elevator, press the first floor button once it arrived, and then let her dog ride down alone. From there, the dog would walk past the doorman, down the front steps, and over to Broadway, where he’d walk himself down to 79th street, over to West End Avenue, then back up towards home.

When he arrived back at the building, he’d patiently wait next to the doorman’s desk, until somebody led him back to the elevator, and pressed the twelfth floor button to send him up.

Very convenient.


A few years back, Jess was working as the CMO of a women’s shoes and accessories company that had a store on Elizabeth Street in Soho. Across the way was a store for Terra Plana, a minimalist shoe company that made Paleo-friendly, barefoot-mechanics-inspired footwear.

Philosophically, I loved Terra Plana; I was certain that shoes with a zero-drop, ultra-thin, flexible sole and a toe box wide enough to allow toe splay, would have huge positive health effects on feet, ankles, knees and hips.

But it took Jess just a quick glance through the window to form an even stronger counter-argument: the shoes looked like crap. There was no way I could wear them to work, she declared, and I certainly wouldn’t be wearing them out anywhere with her.

That’s why I was particularly excited to meet Jeff Mroz a year or so back. A fellow Yalie who played football for the Cowboys and the Eagles before heading back to b-school at Wharton, he was working on a handful of interesting projects. Among them, a line of barefoot shoes that actually looked good.

After a year of hard work, the result is Altum, which miraculously appears to be succeeding on both the fashion and function fronts. They’re taking pre-orders now for their first run, and I’d strongly encourage you to check them out.