over-sharing

There was a brief stint, after graduating college and transitioning the Silicon Ivy Venture Fund from active investing to working with existing portfolio companies, that I had absolutely no idea what I was going to do with my life. In its support stage, the venture fund wasn’t really a full time job, and the market wasn’t right to raise a second fund. I knew I wanted to start another company or two, but I was entirely unsure of what, exactly, those companies were going to be.

I related as much to Mark Gerson, a long-time friend, one night over dinner. Mark had founded and was running the hugely successful Gerson Lehrman Group, a boutique investment advisory firm that works with some of the nation’s best hedge funds and mutual funds. As I had helped Mark out in the earlier days of his company – lining up some of their first clients and early employees – he offered to return the favor, by bringing me in as the firm’s Senior Technology Analyst.

In some ways, the job was perfect – I was overpaid, underworked, with about as much power and autonomy as I could hope for in a company that I didn’t run.

And I was miserable.

I always knew, at some level, that I was a pioneer, not a settler; that I had to mark out new territory, make new things, rather than just expand existing things ever onward and upward. But I didn’t realize how much taking a ‘real’ job would chip away at me. The psychological stress of being an employee, not an employer, weighed on me constantly, manifesting itself in remarkably strange ways.

Unlike in my current job, where I rarely spend more than a half hour seated at my desk – wandering off instead to internal meetings or external business lunches and dinners – at Gerson Lehrman, I spent most of my day sitting in front of a computer monitor, banging out reports, fielding calls, and generally being (or at least feigning being) productive. And, as a result, I drank lots and lots and lots of water.

Perhaps it was sheer boredom, the lack of anything better to do. But each morning, I’d open up a Crystal Geyser bottle, start sipping away, and soon find I was refilling it from the water cooler throughout the day at nearly half-hour intervals.

As a result, my primary cause for leaving the desk was heading off to the bathroom. And in those bathroom trips, something strange started to happen. Despite definitely having to go, my bladder was suddenly shy. At first, I couldn’t start peeing when someone was at the adjacent urinal. Then I couldn’t pee if there was anyone within the entire bathroom. Eventually, that parauresis slipped over into my non-work life as well – even in bar and restaurant bathrooms, I couldn’t pee when someone else was around.

As strange as it may sound, I didn’t think much of it at the time. The problem snuck up on me gradually, and like the proverbial frog in the slowly heated pot of water, I didn’t notice it had happened until I was already in deep.

Then, after a little less than a year, I had a series of small epiphanies. I knew I wanted to make movies. I knew I wanted to publish books and release CDs. I knew I wanted to keep working in entrepreneurship and technology, though in ways that helped the world. The Paradigm Blue companies were born. And I couldn’t wait to get them started.

I was worried about telling Mark that I’d be jumping ship, worried that he’d somehow be insulted by my suddenly moving on. To my pleasant surprise, however, his reaction was exactly opposite; he was enthusiastic, supportive, offering to help in a slew of ways as I set about getting the first company, Cyan Pictures, off the ground. And while I offered to stick around for another few months if they still needed assistance, he graciously said he’d be happy to let me head off at the end of the week, as he knew I’d be eager to get down to business.

I remember walking out of his office, stopping briefly at my desk, and then realizing I had to use the bathroom. And I remember, vividly, walking into the crowded bathroom, walking up to an empty urinal, and peeing away with reckless abandon.

The shy bladder was gone, and it hasn’t, not even once, come back since.

loquacity

Given my verbose writing style, it should come as no surprise that – in real life – I’m a talker. And, frankly, I’ve been one for most of my life. My parents’ frequently tell me that, during my first days at preschool, when asked if I wanted some crackers at snack time, I apparently replied: “actually, I think I’d prefer a croissant.”

Still, despite my garrulous nature, I’m also fascinated by people. So I ask questions, and force myself to shut the hell up and listen. Amazingly, when people know you’re really paying attention, realize you actually care about their answers, they’ll spill the beans – even those beans closely held and rarely discussed. On an almost daily basis, I seem to hear, ‘wow, I can’t believe I just told you that; I haven’t talked about that with anyone before.”

Which, while often fascinating and flattering, occasionally leads to rather unexpected results. Last night, on a long cab ride home in the wee hours of the morning, I suddenly remembered an equally long cab ride, almost exactly a year back. That night, for about twenty minutes, the cab driver regaled me with stories about his childhood, about the psychological effects of having a father unable to truly express his emotions. By the end of the ride, I was the one thinking, “I can’t believe he just told me that.” Or at least that’s what I was thinking when I wasn’t focusing all my attention out the window, looking for a soft landing spot should he verge any further into serial killer territory, necessitating my jumping out of the moving vehicle.

quick note

As mentioned previously, I’m off in Utah through Monday for the Reboot Conference, exploring questions of Jewish identity, meaning and community. Daily postings to resume shortly.

today’s quote

“Living at risk is jumping off the cliff and building your wings on the way downî
– Ray Bradbury

[Thanks mom!]

blog zen

“I just never knew that so much went into organizing a wallet. I would assume that an afternoon with a three year old would produce more material.”
– Senora Juego, in an astute comment on yesterday’s post.

***

I’ll be the first to admit that, when I write nearly a thousand words about wallet maintenance, it’s not because I’m wildly passionate about the subject. Instead, it’s what happens when, sitting down at the computer, I realize I have absolutely nothing to say.

***

Writers block is a fact of writing. Anyone who writes regularly, who routinely starts new pieces from scratch, has – at least on occasion – faced the terrifying nothingness of a white screen or blank piece of paper.

Novelists bitch and moan about it, drink themselves to death as a result. Working journalists, conversely, tend to simply slog their way through, quality be damned; a deadline’s coming, they ain’t gettin’ paid unless they turn in two thousand words, and so they might as well just put something onto paper.

And, in that sense, we webloggers are nearly journalists. The deadlines may be internal, driven by a sense of obligation to regular posting. But they weigh down none the less. The blank screen looms, and we simply write the first thing that pops into our heads. Quality be damned.

***

Often, when I talk to people who’ve just taken up blogging, they’ll tell me that they don’t intend to blog for long. They’ll simply go until they’ve told all the stories they’ve, for years, wanted to tell. And then they’ll quit.

Invariably, this never happens. Through the process of blogging, they come to realize that, in our small daily adventures, the minute facets of our lives, there are literally thousands upon thousands of stories and speculations to tell and share. We could never possibly run out.

And yet, day by day, it’s often difficult to see those facets and adventures. They’re too small to us, too constant, too much a part of life.

***

There is an old Koan about a young monk who, seeking enlightenment, asks Master Dae-Ju to tell him the path to Zen. Dae-Ju replies, ìZen is very easy. When hungry, eat; when tired, sleep.î

We spend all of our lives doing things without really doing them. We go through the motions. We walk through our parts. But are we really present?

If this is the path to Zen, it’s also the path to blogging well. To find material, we needn’t change what we do, merely the way we do it. Fully experience each day, and surely in each lies a story worth telling.

Of course, like any truth, it’s easier advice to mouth than to follow. Unlike Zen, though, blogging provides constant feedback in that pursuit, a daily test of how well we’ve stuck to the course of fully living. Do I have a story to tell? And, if not, is it really because nothing happened to me in the past twenty-four hours? Or is it because so much happened that I somehow missed it all, even as I marked my way through?

***

Keeping a weblog, then, is easy. When inspired, write; when finished, stop. Live through today. Return tomorrow. You’ll doubtless be inspired to write again.

back pocket

Dear fellow men:

In case you have not already realized it, women are checking out your ass. And, frankly, if your wallet is so overstuffed as to appear that you’ve developed a large, cancerous ass-cheek growth, you’re probably not helping your cause.

So, if you’re looking for love, or simply looking to not be labeled ‘ass-cheek growth guy’ by the group of cute girls at the end of the bar, it might be time to slim down your billfold.

Thus convinced, start the process by examining the wallet itself. If it is made from cordura (or, really, anything other than leather), you will not have even the vaguest of chances of sleeping with any woman who sees you remove it from your pocket. (In fact, this applies even if the woman in question is a member of PETA; I am fairly certain there’s a special exemption to their animal cruelty platform that allows the purchase of leather wallets to keep guys from looking like complete doofuses.)

Also, if you have a crappy five-dollar wallet, every single woman who sees it will instantly know it’s a crappy five-dollar wallet. Women spend huge percentages of their adult lives idly searching for the perfect purse and handbag, across thousands upon thousands of stores. They have examined more leather goods in a single afternoon than you have in your entire life. They know the difference. Your five-dollar wallet isn’t fooling anyone but yourself.

Additionally, if your wallet is tri-fold, multi-fold, or in any way resembles an origami project, trade it in for a plain old fashioned one that simply folds in half once. Obviously, the more you fold something, the thicker it becomes, and some wallets are a good inch and a half deep even before you start filling them up. If you’re still at a loss, just buy this, which I’ve owned for the last eight years. Thanks to, as you’re about to learn, not overstuffing, it still looks new.

Onto what goes into the wallet. To gauge where you stand, remove everything from you wallet, and make four piles: one for money, one for credit cards / id / etc., one for receipts, and one for anything else. These piles are likely rather unwieldy, which is exactly the problem. The goal here is to put as little of what’s in those piles back into the wallet.

Start with the money. That’s the one thing that incontrovertibly belongs in your wallet. Everything else should be subjected to close scrutiny.

Next work your way through the card pile. From it, place in your wallet: your drivers license, your atm card, one or two credit cards, your metrocard (if you are a New Yorker), four of your business cards, and your health insurance card. That’s it. Put everything else in your desk drawer. Seriously.

You simply cannot afford to stuff you wallet full of things you don’t truly need. You don’t, for instance, need to carry twelve different credit cards all at the same time. At most, you need one for personal expenses and one for business expenses. If you’re worried about maxing out your limit (which, frankly, you probably shouldn’t be doing in the first place) you can swap the nearly maxed card for another unused one from your desk drawer as necessary.

You also don’t need things like your Blockbuster card or your museum membership cards; if they can find you in their computer system given your ID, you shouldn’t be schlepping their plastic around. Even if your grocery store doesn’t allow you to key in your phone number for rewards club savings, say, you still likely don’t need to take your grocery rewards card with you everywhere. If you’re just ‘stopping by’ the grocery store, you’re unlikely to buy much; when you head out for a big shopping run, you take the card out of your desk. The rest of the time, you leave the card, and most others, at home.

Now the receipts. Take all of them, put them in a file somewhere, and never, ever again put a receipt into your wallet. Put new ones in your front pocket, then add them to the file when you get home. Receipts are the single largest cause for outlandishly overstuffed wallets. And there is absolutely, positively no reason for carrying those receipts around. Most guys have returned perhaps two items in the past five years. When return number three rolls around, you can damn well pull the relevant slip from the file. The rest of the time, the receipts add bulk, look stupid, fall out everywhere, and generally detract from good wallet housekeeping.

Now the miscellaneous pile. If it doesn’t already include it, take a single check, a $20 bill and a $100 bill, and fold them together. Place this in one of the inside pockets of the wallet. This is ’emergency’ money, or, more to the point, ‘cover dinner after your credit card is declined so that you and your date don’t end up in the kitchen washing dishes’ money. Not much else from the miscellaneous pile should be added back into your wallet either. If you want to carry pictures, limit yourself to one of your significant other, and one each of any children you have (and know about). Nobody wants to see even the first photo, so please don’t torture them with a stack.

That’s it. Keeping your wallet organized is easy: aside from cash, and replenishing your stack of business cards, do not put anything new into your wallet. Try it for a few weeks. Then head back to the bar where the cute girls secretly taunted you for your unwieldy buttock-bulge, observe the newfound respect your svelte wallet and resulting slim line engenders, and ask the cutest for her phone number.

And, even then, place the phone in your pocket. Not in your wallet.

transmogrification

With summer weather now more or less upon us (discounting the chance spring shower), most of my New York hipster shoes have gone back into the closet for warm weather hiatus, replaced by the trusty California-boy standard flip flops.

Slipping them on, my gait changes immediately. My steps are easy, deliberate. And so my pace slows – I’ll get there when I get there.

Gradually, the shoe shift makes its way up through the rest of my body. My movements become smooth, relaxed. The constant concerns crowding my brain step aside for thoughts dominated by the words ‘dude’ and ‘rad’.

Work becomes less natural – the constant glow of the monitor no longer draws me, moth-like, to productivity. Instead, I catch myself looking to the window, where the bright sun beckons me outside.

I try and focus on the tasks at hand, but with the flip flops on, my brain is elsewhere, somewhere where I can feel coarse sand between my toes, cool salt-water on slightly burnt skin.

the lineup, amended