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 The Gen Y’ers see this as the very point: why keep out-of-date copies at all, unsure whether the one you’re looking at reflects the most current collective thinking?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.

Farmer Josh

When I started elementary school at Ohlone, it had just inherited an acre or so of weed-ridden, fenced-off land at the very back of the campus, which the students called “no-man’s land.” A few months into the year, the staff decided to put the space to use, converting it into a small farm.

Each class elected a representative to the ‘farm council’ to help with planning, and I was elected from the kindergarden class. Kids, parents and teachers cleared out the weeds, and laid in plot markers. And then, class by class, we planted collective plots. I was hooked from that first year, planting carrots, lettuce, herbs. I remember pulling radishes from the ground, rinsing them off and eating them raw. I didn’t even like radishes at the time, but I couldn’t help but relish something I’d planted and grown myself.

Throughout elementary school, my love for the farm deepened. I spent my free time studying seed catalogues and gardening manuals. When I was in third grade, I planned out an elaborate drip irrigation system, which the school later purchased and installed. I served on the farm counsel every year, and, by the time I was in sixth grade, was appointed honorary ‘farm historian’, and ceremonially given a key to the farm.

But what I loved most about the farm were the animals, which the school slowly accumulated. By the time I graduated, the farm housed ducks, goats, potbellied pigs. And, nearest of all to my heart, chickens.

I’m not sure what it was about the chickens that I loved so much, but I found them endlessly fascinating; I could sit with them happily for hours on end. To this day, my mother reminds me that when she washed pants or jackets I’d worn to elementary school, she’d have to empty handfuls of chicken feed from my pockets.

One spring break, with new chicks just out of the incubator, I convinced my parents to let me take the dozen of them home, to roam in our fenced backyard rather than stay at the farm alone over the vacation. Several of the birds had terrible intestinal distress, trailing diarrhea everywhere, but my parents were remarkably game about it; I remember my father hosing the patio down, while talking on the phone with the farm’s vet to make sure we didn’t need to do anything but wait it out.

Each year, the farm would have a parent-child farm work day, when helpful hordes would descend, spades and power drills in hand, to fix up what we could. After just a few years of use, the chicken roost the school had purchased initially began to fall apart. So at one year’s work day, my father suggested that we make a new chicken roost from scratch. I remember shopping for the wood – a trunkful of 2×4’s and dowels – and then learning to use various power tools under his watchful eye as we pieced together an elaborate setup. At the end, we soldered in an inscription: Newman & Sons Chickenworks.

About fifteen years after I graduated, my father got a call from the then principal, who had previously taught me in third and fourth grade. After long use, that roost was in need of repair or replacement, and he had remembered our bringing it in. He wanted to see if we still had contact info for the Chickenworks. Laughingly, my father explained that we were it, then shared the plan we’d used so that a new parent-child duo might build the next generation’s.

I still think about that farm occasionally, and I’m proud of the hand I had in getting it up and running. But whatever impact I had, I’m sure it’s had a far bigger impact on me.

Down to Work

“I have always thought that one man of tolerable abilities may work great changes, and accomplish great affairs among mankind, if he first forms a good plan, and, cutting off all amusements or other employments that would divert his attention, makes the execution of that same plan his sole study and business.” – Ben Franklin


Growing up in Palo Alto, most kids attended one of a dozen neighborhood elementary schools. But parents also had the option of sending their kids to two ‘choice’ elementary schools.

One, Hoover, was extremely structured and disciplined; if the class was doing math, everyone was open to the same page in the same book working on the same problem at the same time.

The other, Ohlone, was the complete opposite. No tests, no grades, no homework; kids learned in mixed-grade classes, called teachers by their first names, and met in small seminar groups with the teacher for part of the day while self-supervising project and problem set work the rest of the day.

I went to Ohlone.

As a result, by the time I headed off to Yale, I still couldn’t place all fifty states on a map. (Seriously.) But I had mastered the kind of learning I’d be doing at Yale, and the kind of work I’d be doing thereafter running companies.

As the old saw goes, I really did learn everything I needed to know in kindergarden.


For years and years, I managed all of my tasks, projects, goals and ideas using a handful of text files that I wrangled in the text editor BBEdit. It was nerdy and time-consuming, but also completely bespoke; the approach fit my workflow, and evolved over time as my working style did, too.

Along the way, I briefly tried out pretty much every task management software that existed. Some, like The Hit List or Omnifocus, I even stuck with for a couple of weeks. But, inevitably, I’d end up chafing under a program’s structure, or run into problems with its stability and data security, and return to my free-form text.

About six months ago, for reasons I can no longer recall, I decided to test out the online task management program Todoist. An extremely fast and fluid web app, it also boasted polished iPhone and iPad versions. So I dumped in my text files, and started using it. And then I kept using it. And using it. Two months in, I reverted to my text approach; after an hour, I started to feel that it was text, not Todoist, that fell short in comparison.

Six months later, I still use Todoist all day, ever day. If you haven’t tried it out, you should. (And sign up for the trial of the premium features; they make the app vastly more powerful, and are certainly worth the the $0.08 a day they cost if you decide to stick with it.)

Time Machine

Courtesy of my parents, a birthday look back at where it all began:




As Jess points out, while I don’t yet look like myself at a day old, I do by a year; by a year and a half, I’m apparently already more or the less the guy I am today.