When people comment that I seem to juggle an overwhelming number of interests and obligations, I usually joke that my secret is stopping sleeping and going to the bathroom to free up time.

And, frankly, I wish that were true. Some people seem to get by remarkably well on just three or four hours of sleep a night. Sadly, I’m not one of them.

Sure, for short stretches, usually during production on a film, I’ve gone entire weeks with less than ten or eleven hours of shut-eye. But, by and large, as I scale back from a solid eight hours a night, I start to feel increasingly off. Most people pour on the caffeine to push through, but I often find coffee hits me the hardest – and least helpfully – when I need it most. Perhaps it’s my already manic, fast-talking personality, or my hummingbird metabolism, but several cups of joe after a few sleep-deprived nights mainly leaves me twitching, with jumbled thoughts and a tongue that can’t seem to form sounds in time with the thoughts my brain is trying to push out.

The past week, which so far has featured evening drinks each night followed by breakfast meetings each following morning, already has me piling up the sleep debt. And, after just a few days, the effects are already starting to wear on me. I lose my train of thought in mid-sentence, find myself frequently looking up in the air as if perhaps what I’m trying to say might be written on a tele-prompter just over a conversation partner’s shoulder.

This morning, though, in searching for a set of financials from an earlier company that I could repurpose into support material for Long Tail, I stumbled across an essay I had written a few years back for one of the slew of now defunct e-business trade publications. Reading it, I was startled by my own prior thinking. As Cyan and Long Tail are both undoubtedly long-hauls, perhaps it’s time to start taking some of my own earlier medicine: sleeping through the night and trying to live with a bit more sanity.

The article:

A few weeks ago, I sat down to lunch with a long time friend and tech CEO to talk about how his company had faired since the market soured a year ago. For the most part, he said, life was business as usual. Except for one thing: he had begun sleeping eight hours a night.

In most circles, that might not seem unusual. But in the dot-com world, lack of sleep has traditionally been seen as a badge of courage. This very friend, for example, often went for days sleeping only in quick power naps on a mattress kept under his desk, and was famous for the time that he fell asleep while walking down a hall. Dozing off mid-stride may seem a bit extreme, but more entrepreneurs than not have similarly bizarre sleep deprivation stories to tell. Intrigued by my friends somnolent confession, I spoke with several more. The consensus: most of the entrepreneurs I know are sleeping several hours a night more than they had been twelve months back. In the past, they admitted, they were stockpiling sleep options for that post-IPO vacation. But with company building once again a long-haul pursuit, they now wanted to pursue a more sensible and sustainable pace.

Certainly, well rested execs are a change in the right direction. After all, according to a recent study by the National Sleep Foundation, sleeping five hours a night (versus the recommended eight) actually decreases productivity by a full 43%. And with sleep deprivation a factor in 60% of car accidents, one has to wonder whether as many companies were dragged down by sleepless CEOs. But more interesting to me is whether this increased sleeping is indicative of a larger trend. With the dot-com rush petering out, has the actual pace of business life slowed down?

Consider the intriguing case of the Slow Food Movement. The Italian organization, symbolized by its distinctive snail mascot, works, according to its manifesto, towards ìa firm defense of quiet material pleasureÖ the only way to oppose the universal folly of Fast Life.î The group, which organizes local chapters across the world, has begun to take hold in the US, organizing vineyard tours, cheese tasting workshops and mushroom picking expeditions. Most tellingly, the largest US chapters of the organization have sprung up on entrepreneurshipís most hallowed grounds: Silicon Valley and New York City. More to the point, even the new economy rag Fast Company (a magazine boasting the tagline ìeverything fastî) ran a glowing feature piece on Slow Food. When the number one proponent of new economy fast begins to extol the virtues of old world slow, certainly major change is under foot.

The question, then, is where to go from here. Perhaps adding a midday siesta, taking Fridays off, and scaling back to bankerís hours? Certainly, none of those options seem particularly likely. Like it or not, the world of entrepreneurship is dominated by passionate, driven individuals who keep going for no other reason than theyíre having too much fun to stop. Because at the end of the day, even the most sleep deprived exec is craving the endorphins that come from a solid pitch, a closed sale or a good contact at a networking event. Perhaps what we can expect, then, is a bit of sensible moderation. While entrepreneurs may continue to work and play hard, it seems theyíve begun to understand when even they need to take a break.

With the first official week of Long Tail well underway, my life has been exceedingly, overwhelmingly hectic. Though in a good way. I’ve been inking partnerships, rolling ahead towards the release of our first film (This is Not a Film, out February 1st), hiring on a team of people vastly smarter and more talented than I, and generally gearing up to take the movie world by storm.

And, frankly, I’m excited. Wet-your-pants excited. So excited that, today, mid-way through adding a few new sections to the business plan, I literally got up and did a little dance, only stopping when I realized the people in the law firm across the street could totally see in through my window.

Sure, Cyan’s a startup too. But, in its day-to-day operations, it’s been completely different from any other startup I’ve ever dealt with. In movie production, everything you do, absolutely everything, is dependent on extensive collaboration with a slew of outside individuals and organizations. Which is part of what makes making movies fun. But also all of what makes making movies so frustrating. Unlike in most startups, no matter how hard we push, the vast majority of Cyan time is ‘hurry up and wait.’

Having the ball, primarily, back in my court, with the responsibility and potential that implies, has made this week rather jarring. If things aren’t moving ahead as quickly as I’d like on Long Tail, it’s my own damn fault. Which, I realize, is what attracted me to the world of entrepreneurship in the first place: the chance to build something extraordinary, bounded only by my own ability to think of amazing ideas and then put them into action.

And while I knew, instantly, from that first night of staring up at the ceiling, running through plans, too excited to sleep, that I would feel different with Long Tail underway, I didn’t realize how much that would bubble out.

So far this week, for example, on three separate occasions, I’ve had people tell me I was the best salesman they’d ever met. And, frankly, while flattered, I know that’s not true. I’m not really much of a salesman at all. Having seen the pros at work, the people who could sell proverbial ice to Eskimos, I know I’m nowhere near that ‘coffee is for closers’ league. But, as the first of the three pointed out this Monday, it seems I’m starting to channel a Steve Jobs-esque Reality Distortion Field. By the end of our meeting, he commented, he felt ready to sell a kidney if that’s what it took to partner his company with ours.

Reality Distortion Field? That I’ll own up to. And that, I think, is what the kind ‘best salesman’ commenters really meant. I’m sure a better seller’s pitch would be more eloquent, her responses to concerns more carefully reasoned. But I have trouble believing that anyone could be more excited, more thrilled to get down to work on fundamentally changing the way the movie industry works.

Will Long Tail succeed? In rational moments, I’d give it maybe 65% odds. But, given the will I’m ready to put behind it, given the passionate, talented people and companies ready to throw their full weight into the fray, it’s a bet I’m 100% willing to take.

Starting a company: it may not be cheaper than Zoloft, but it’s certainly more effective.

I am an information addict. For all of my life, I’ve loved ideas: facts and theories, concepts and conjectures, knowledge and wisdom. In short, anything I can pack into my brain. Which makes the internet a dangerous place for me. I can – and often do – waste hour upon hour, exploring, reading, surfing from verbose site to equally verbose site.

This morning, for example, my carousing took me from fractal geometry to the biological evolution of morality, from the feng shui of desk layout to the history of electoral math. And, frankly, it didn’t take me there quickly. Were I simply to click my browser closed, I’d easily free up hours each day, cross far more of my lengthy to do list.

But I don’t. And, for that, I’ve always harbored more than a bit of guilt. Oh weak-willed self! Oh procrastinating spirit!

Today, though, in between surfing stretches, I set out to write the start of yet another chapter of Radical Entrepreneurship, the unorthodox business book I’ve been slowly and steadily piecing together over the past months. The chapter was on ideas, and, particularly, on how and where to find good ones. Though I’d outlined most of the other chapters to a disturbing degree, this one was – to put it mildly – still a bit vague. Where, exactly, do ideas come from? And what, if anything, can we do to make more good ones?

Pondering that question, I flashed back to a point made by David Gelernter, an eccentric Yale computer science professor who – among other things – revolutionized parallel computing, got Unabombed, and penned a book proclaiming the 1939 World’s Fair as the height of world civilization. Gelernter, I remember, once pointed out that great ideas rarely come from people deeply entrenched in a single field. Instead, paradigm shifts depend on ‘top view’ – the ability to look down across multiple disciplines, to connect together disparate ideas that neatly interlock in ways nobody previously considered.

Starting a company, it’s remarkably easy to get pulled deeper and deeper into the minutiae of operations, to look no further than the balance sheets and business plans piled up on desktop. Which, frankly, is a huge mistake. It’s exactly that laser focus, that lack of step back and think things through with the new perspective of new ideas, that gets businesses into trouble, cuts off innovation before it even begins to take root.

And, with that in mind, as I pulled up pages on bookbinding and calligraphy this afternoon, for the first time I didn’t scold myself for time wasted. I didn’t even press to find links between the new thoughts packing my mind and any of my more day-to-day pursuits. I simply let the information sink in, confident that, somewhere, somehow, I’d be able to put it to good use.

As Da Vinci once observed, “men of lofty genius when they are doing the least work are most active.” Despite the name of the site, I certainly won’t lay claim to lofty genius. But least work? That, I think, I’ve got down pat.

Over the summer, I ended up on a panel of entrepreneurs, speaking to a group of high school students about the startup world. It’s something I do fairly regularly, and, by now, I’m ready with standard answers to most of the questions flung in my direction. If the questions don’t catch me off guard, however, the other panelists’ answers often do.

At the last event, for example, the moderator asked for our thoughts on the hardest part of starting a company.

And, after a requisite moment of brow-furrowed faux-thought, the first panelist replied: coming up with good ideas for potential products and businesses.

I almost jumped out of my chair. Coming up with ideas? The hard part? No, no, no.

Ideas are a dime a dozen. Give me five minutes, and I can come up with a laundry list of products that would sell millions (try: biodegradable tattoo ink, for tattoos that disappear after five years; or, disposable six-pack coolers made using the same chemical mix found in instant-cold break-and-shake medical ice packs). Even ideas for whole businesses take only a bit longer – just enough time to sketch out the model on the back of a napkin.

But, actually making those products and businesses happen? Now that’s hard.

No matter how simple an idea seems, the execution is always an absolute mess. Which is why, like a newborn baby, a startup eats all your time and money, and leaves you completely sleep-deprived for months or years on end.

In the case of children, we’re biologically geared to love our offspring more than life itself – that’s what (usually, at least) keeps people from ditching screaming brats in a dumpster somewhere. But, when it comes to starting companies, there’s no similar inherent drive.

Sure, most people assume that money’s a good driver. But, in reality, entrepreneurs chasing cash rarely bring in the bank. The specter of IPO riches, of post-acquisition tropical trips, is simply too distant and too uncertain to motivate a team through eighty hour week after eighty hour week. To make it through the long slow slog of actually putting a company together, you have to like the operational specifics of the company. In other words, you have to like what you’re doing each and every day enough to want to come into work.

It’s a lesson I sometimes forget. Over the last few years, I’ve put together full business plans for additional companies I was considering starting. And, with each, as I began to lay out timelines for execution, I realized that, after several years of actually carrying out the plan, I’d mainly be likely to execute myself.

That’s why, despite any of its problems, I’ve loved starting Cyan. At the end of the day, even at its worst, making movies is vastly more fun than having a real job. And that’s also why, at the top of the column to the right, there’s a new company name, in italics, just below Cyan: Long Tail Releasing. It’s the first company idea I’ve had outside of Cyan in the past three years that I’m actually excited to work on, day in and day out, over the next decade of my life.

While I’ll let further details emerge over the next few months, suffice it to say Long Tail is an alternative distribution company that dovetails well with Cyan. Production and distribution companies? Harvey Weinstein, look out.

In the entrepreneurship book I’m writing, in the chapter about networking, I talk quite a bit about the power of doing homework – learning everything you possibly can about a person you’ll be meeting before you actually meet up. People are always surprised and flattered to discover you’ve gone through the trouble of finding out more about them, and you can build strong ties very quickly by knowing in advance common interests that can launch discussion.

I say this because, in two weekends, I’ll be heading to the Reboot conference, a yearly retreat organized by the Spielberg and Bronfman foundations, at which young Jewish movers and shakers (and this year, by their likely mistaken inclusion, me) try and assess the state of American Judaism, of how to make the evolving religious civilization of the Jews relevant to modern life. As one past attendee jokingly described it, sort of the yearly meeting of the Youngers of Zion.

Yesterday, I received in the mail a large packet from Reboot, with about twenty-five articles and excerpts meant to ignite thinking in advance of the actual event. And, in the pile, was a collection of short bios of the fifty or so attendees. So, following my own advice, I’ve been diligently researching each attendee through the magic of Google, making flashcards for each, and working to memorize their individual details.

It’s a bit of an experiment, as I’ve never tried networking research on such a large scale, and I’m very curious to see whether it actually pays off.

While I’m already knee deep in putting together Cyan’s web writing anthology, and have for years written blog posts, short articles, screenplays, etc., I’ve never really tried to put together an entire book full, several hundred pages worth, of my own thinking on a single subject. So, after much prodding to do so by people I’ve worked with over the years, I finally sat down to outline Radical Entrepreneurship and see if I could think of anything worthwhile to say.

I started by laying out some broad chapter topics – the importance of building a network, where to find ideas, how to raise capital, building a team, etc. And then I started adding in sub-chapter headings, as well as tips and ideas I could touch on within each. My initial fear was that I wouldn’t have enough worthwhile things to say about starting companies to really fill a book. As anyone who’s met me in real life can attest, however, I’m rarely low on words, and apparently that carries over to writing as well. My outline, which started short of a single page, is now close to eleven, and I find I’m constantly remembering other things I should add in. Before, I was concerned I’d end up with a 50 page book; now, I’m concerned I’ll end up with a Harry Potter-sized 800 pager.

Carpal tunnel syndrome, here I come.

Sorry about the relative quiet recently; the writing part of my brain has been otherwise occupied, drafting up the outline and first few chapters of a book on entrepreneurship, tentatively titled Radical Entrepreneurship: Guerilla Startup Tactics from the Real World.

Considering the completeness of the outline, and the relative ease of non-personal nonfiction writing, I should be able to flesh the book out to a few hundred pages rather quickly. More concerning, however, is my ability to balance that writing with keeping the blog alive, something worthwhile less for your ongoing amusement than for my ongoing sanity.

In case you’re curious, here’s the (still very rough) preface, that should give you some sense of what the project is all about.

Preface: What is Radical Entrepreneurship?

The word ëradicalí is an odd one, as it means two wildly different things. Coming from the Latin word for root (radix), it initially referred to the juice in fruits and vegetables, and by extension to the very essence, the core substance of things. Then, as the word evolved, ëradicalí took on a second meaning: extreme and unusual. Given those two opposing definitions, ëradicalí is a great word to apply to the style of entrepreneurship laid out in this book. On the one hand, Radical Entrepreneurship is about the core tasks of starting a company, the simple steps, small details, and nitty gritty of actually making a startup work. On the other, because so few people talk about those things, really lay them out in careful detail, some of the ideas presented may initially seem rather unorthodox.

Still, most of the strategies and tactics in this book are of the ëwhy didn’t I already think of that?í variety. I know, because I didnít think of most of them, at least when starting my first company. (Or, in some cases, even when starting my second or third or fourthÖ) Instead, I learned them the hard way, one mistake, and one subsequent climb back to success, at a time. Itís an ugly way to learn, but it works. Along those lines, thereís a great story about a young man who goes to a very prosperous older man to ask for advice:

ìWhatís the most important thing in life?î the young man asks.

ìGood judgment,î replies the older man.

ìAnd how do I get that?î the young man continues.

ìExperience,î replies the old man.

ìBut how do I get that?î persists the young man.

ìBad judgment,î concludes the old man.

That pretty much sums up this book. The things I present here arenít armchair theories that sound good, or business-school textbook truisms; theyíre the things that actually worked for me in building and selling companies, the good judgments I learned through years of bad judgments. Most of the successful entrepreneurs I know initially seem to have made largely the same bad judgments in their own companies. Therefore, Iím hoping that, by reading this book, and by putting the advice it contains into action, you can avoid making those same bad judgments yourself. That way, youíll be free to pioneer new and wildly creative bad judgments instead. Which is basically what entrepreneurship is all about.

With a year and a half of progress under Cyan Pictures‘ belt, I’m doing what any aspiring mogul would: expanding the empire. Adding to the indie film end of things, I’ll be slowly piecing together Cyan Publishing and Cyan Records, sibling book and music companies, under a broader Cyan Arts banner. I’m still piecing together business plans for both organizations, but they, like Cyan Pictures, will be built around five simple core beliefs:

1. Art isn’t just important, it’s also effective, as one of the best ways to make people think, ask questions, and look at the world and themselves in new ways.
2. The goal of art, then, should be to make as many people think as much as possible. That means art that’s either good or popular isn’t sufficient; art needs to be both.
3. Technology can be a powerful tool, both in creating art and in bringing it into people’s lives. Too many companies are wasting time hiding from new technologies, or actively fighting them, rather than searching for ways to harness them productively.
4. While established voices should always have a chance to continue expressing themselves, it’s also crucially important to find and showcase emerging ones.
5. Artists and customers both prefer to deal with companies that have a sense of integrity and a sense of fun, companies that do the right thing, and have a good time doing it.

For a number of reasons, I’ve always kept this blog relatively business-free, but it’s a policy I’m hereby officially changing (with apologies to readers who’ll be bored to tears by work-related posts). In the next couple of months, as these companies come together (and as, in my parallel non-profiteer life, the Indigo Foundation notches things up), you’ll hear about it here first.

Time to get to work.

Breaking briefly from the pleasure (rather than business) related nature of my blogging, today I link to a new addition to the ‘work’ section of the site: an interview I gave yesterday for a New York Times article about what it takes to do something extraordinary as a student.

Every so often, you get to go into a negotiation and just lay it down. I mean, you own that puppy. You control the pacing and flow, dictate the language of discussion, deftly make moves that seem concessions yet actually push your position steadily ahead. You out-legalese their lawyer, jocularly defuse their emotion-laden contentions, and leave deeper in their good graces than you began the meeting, they with the vague sense that perhaps they came out ahead, and you with the knowledge that, most clearly and certainly, you were the one who did.