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.

Michael Simmons, rising business guru and author of an excellent new book on student entrepreneurship, recently emailed to see if he could shadow me for a day or two, using his findings as anecdotes in his future writings. In theory, I was absolutely flattered. In practice, I was absolutely terrified, mostly at the thought of how short of his expectations such shadowing would fall.

People frequently say to me “you’ve accomplished so much; your days must be incredibly busy.” In fact, they’re not at all. I wish they were. But, in the heat of the moment, I’m a terrible, undisciplined worker, frequently unable to actually sit down and accomplish anything. In those rare moments that I do apply my butt to my Aeron chair, my hands to my ergonomic keyboard, and my brain to the problem at hand, I can bang out work at a whirlwind pace, concentrating laser-like for hours on end where necessary. So much of my day, however, is taken up by the exact opposite – carefully determining what I should be doing and then simply not doing it – that the thought of having someone watch the entire process as a model for achievement strikes me as embarrassingly ridiculous.

To better illustrate, consider my schedule on a representative day from the past week:

8:00 am
Wake up.

9:00 am
Wake up, again.

9:30 am
Wake up, yet a third time. Stumble out of bed to prevent falling back asleep. Consider going into the office but decide instead to work from home. No need to shower, in that case. Could make breakfast, but the tail end of the previous night’s hangover makes the thought of eating somewhat dicey. Instead, briefly check inbox to make sure all email can be temporarily ignored and cell phone to see that nobody tried to track me down in the middle of the night. That accomplished, sit down in desk chair and space out.

9:45 am
Walk into living room. Colin (a roommate and Cyan’s Exec VP) appears to be working at home as well, though much more efficiently than I, having already showered, eaten breakfast, and read halfway through a script sent to us by a large literary agency. Stride purposefully into kitchen, lest Colin think I’m not doing something highly important and executive. Sit down at kitchen table and space out again.

10:00 am
With refrigerator this nearby, decide perhaps I could eat after all. While standing, toss back haphazard breakfast consisting of a very large spoonful of peanut butter, two glasses of milk, a banana, two slices of whole wheat bread, four hard boiled eggs (sans yolk), a chunk of gouda, and a handful of Crispix. Return to desk, sit down and look at daunting to do list.

10:10 am
Decide instead of accomplishing anything on list to look at Metafilter, Google News, Gawker, and a handful of other regularly visited blogs. Consider making the endeavor more productive by emailing various contacts links I’ve come across relevant to their work or interests, but decide the idea is a bit too Harvey Mackay, close all browser windows and look again at to do list.

10:30 am
In search of lesser evils, ignore to do items again in favor of previously ignored emails. Contemplate best approach to standard weekly melodramas emerging on I Love Your Work. Add three or four related calls to ignored to do list for completion once the callee’s arrive in their California offices.

11:00 am
Decide to start chipping away at to do list after all by accomplishing smallest, least daunting tasks, in this case daily practice of guitar and upright bass, two new instruments I’m trying to learn.

11:20 am
Realize I’ll probably have to do some actual work sooner or later, so, taking opposite approach of previous effort, choose the ugliest, most daunting task on the list, and (surprisingly painlessly and quickly) bang out new drafts of several key co-production financing term sheets for Miller (our next film). Send them to Yoav (Cyan’s Finance VP) for feedback.

12:15 pm
Reward myself for actually having done something productive by pissing around with HSX portfolio.

12:30 pm
Meet Yoav at the Go Sushi on the corner (as he, similarly, is working from home, and lives about a block and a half away). Eat bad chicken teriyaki bento box and go over Yoav’s changes to the term sheets as well as general fiscal strategy for the film.

1:15 pm
Receive call about previously read-about I Love Your Work melodrama and decide now is good time to spring in to action on previously noted calls. Via phone: shake hands, kiss babies, play good cop, play bad cop, and, for yet one more day at least, manage to keep all the various parties involved in finishing the film happy enough that we continue to roll ahead towards a polished finished product. Feel good about life due to positive comments on the state of the cut from several of the more respected of the individuals called.

2:00 pm
As further escapism, practice trumpet.

2:45 pm
Get back to work. Open draft of an investment document, stare at screen, get up, wander aimlessly, sit down, stare at screen, repeat, repeat, repeat. Intermittently stop in kitchen to pick up various snacks before returning to more blank staring and aimless wandering.

3:30 pm
Saved by a string of work calls. Engage in more cajoling, threatening, hard and soft selling, in the end yielding surprising progress on a couple of Cyan and Paradigm Blue projects.

4:30 pm
Yoav has headed into the office briefly to check for some incoming documents, and stops by our apartment on the way back to hand off a number of just-received scripts. We stop to watch a daily movie (a key Cyan ritual), and though we should select something like Paths of Glory or Ponette (both in from Netflix), we decide to watch a recently completed Portuguese film (Chasing Life) we received along with one of the incoming scripts from the same writer/director. After about fifteen minutes, it is entirely clear there isn’t a chance in hell we’d produce any of this guy’s films, yet, in the same way one might touch a canker sore on the inside of their lip repeatedly just to make sure it still hurts, we can’t help but watch the rest of the film.

6:30 pm
Return to desk to stare at investment document one last time before giving up for the day.

7:00 pm
Off to a dinner meeting at Uncle Nick’s Ouzaria with Hannah and Nicola, the heads of Stellar, a networking group for young New Yorkers in film that wants us to sponsor their upcoming screenwriting competition. We get sidetracked from the ostensible purpose of the dinner fairly quickly, which is probably just as well as the two have yet to prepare any sort of concrete sponsorship proposal. The food is excellent.

9:30 pm
Head over to Russian Samovar to meet Yoav and Colin for a general rundown on all things Cyan, as well as for several carafes of New York’s best handcrafted vodka. Natasha, our favorite bartender, is out sick for the evening, so sadly we actually have to pay for the drinks.

12:15 am
Stumble back home. Consider relooking at forsaken investment document, but decide it would be better saved until more sober moment. Get ready for bed.

12:45 am
Spring out of bed with sudden relevation about the digital future of film distribution, a relief since the Director’s Guild wants me to talk at their upcoming Digital Day about this very thing, and I previously haven’t a clue in the world what I might say.

1:30 am
Back to bed.

1:45 am
Spring out of bed a second time with an idea for a short story.

2:00 am
Back to bed.

2:22 am
Having lain somewhat drunkenly awake thus far, convince myself that my alarm clock’s current numeric alliteration must be a good omen. Roll over and finally fall asleep.