This started as a letter to my friend and fellow entrepreneur Wendell III, in response to his email of, "Haven't heard from you guys in a couple of weeks; what's happening?" (Did you know? That I'm officially America's newest high-powered, highly-paid corporate-executive bigshot internet startup guy? No? Click here, and try to come by here a little more often from now on, okay?) And then the letter grew, and it grew, and it turned into this, which I thought I'd just post here, because I'm too exhausted to write it all again from scratch. Certain names deleted, certain names changed, certain details turned back into hidden ones; this is tricky stuff, you know? It's hard to be in charge of a lot of money, a lot of industry secrets, and write a confessional journal at the same time. I'm working out a balance. You know how it is.

For those who are curious, by the way: yes, I run these by my boss before I post them. Not because he requires it; because I respect him, and want to give him that chance. Why has no other boss I've ever had in my entire life ever understood that, that I'd let them edit my personal journal if they'd just earn my respect first?

So last we talked, we were going crazy at MetroProper, trying to put together a new team to rebuild us a website, after our first one ended up remaining semi-crappy long after we were live and public. First we got our friends from Sand Software to take on the actual PHP programming; which they're qualified to do, don't get me wrong, but you were right, were going to have a challenge actually framing the entire infrastructure, and even admitted it themselves. And then out of the blue, volunteer help from Tom Gillis; who, we learn later, was on the development team of Williamsburg.org, this coding/project-management cowboy who is just a constant traveler, off to New York again next month, in fact, who we just caught at the right moment. Wow. AND it turns out that he actually had a lot of MetroProper-style ideas he had always wanted to try at Williamsburg.org, before the owners gave up interest in the whole thing; so we asked him if he'd like to come on at a decision-making level too, and help us craft our long-term vision. And he said yeah, he'd love to.

Then we got Lauren Liss, who runs a one-woman design boutique at Goodspark.com, on as our front-end engineer; Web 2.0er, Ruby lover, daily reader of Jakob Nielsen, who nonetheless knows how to use AJAX, Flash, etc., as well. Perfect. And voluntarily offers us a great deal, because we've asked her to come on in a decision-making role as well, if this project goes well. That's been a real key to the whole thing, in fact, and is something that led us to the new concept for senior management we have, is simply asking these people if they'd like to be a part of shaping our long-term vision; but that's way to come, a whole other letter coming after this one. You know; she's whatever, 27, great smart designer, just had her first big burn by a big giant agency, now wanting to get involved at the ground level with a really smart site that she can have a direct influence over. This first taste of real power, I'm learning, can in the eyes of many in their late twenties help get them to sign on; and now that I think about it, I would've eaten up the chance to do this at 27 too. Hell, I'm eating it up at 37! And, you know, technically, actually, getting paid less than our designer too, until our full financing finally kicks in. And I still love it!

So a great working dynamic now; Tom listening to what Phil and I want, relaying it to Sand and Lauren in tech-speak; them turning things around quickly for him to review; and then for us to either see too (design) or a plain-language report on something module-oriented (PHP). That's our infrastructure, by the way; I don't understand the details, but basically a high focus on elegant stand-alone modules, and the smartest minimalist system possible for connecting them together. Or, er, something like that.

And yeah, guess what? We're now completely on track with everything, and are going to have a completely working website going early alpha on August 15th; something that people will go to and immediately say not only, "OKAY, I get it NOW," but also, "Fuck, this is cool!" Then a nice two slow weeks of testing, with maybe a couple of hundred early adopters total; then an official relaunch on Friday, September 1. New promotional campaign; new release to the press; second party, deliberately smaller in scope and more intimate, not a "forget our first party" party, but a "whew, we're glad it's finally working" party. At Dollop, lots of liquor, full partnership with Unscene magazine. Yeah, great.

And S----? Our last development team? We fired them. And yeah; it felt great. I admit it. We had a lawyer and all fancy-pants law-firm letterhead and everything. It felt great. And Phil ate what I consider a rather substantial chunk of money because of it all, although a lot of the people we've been meeting with lately would call it pocket change. That was the consequence; there's a consequence to every decision, as both Phil and I are both learning very quickly.

Two great things came out of it:

1) Phil learned a lesson he won't forget: that he can't hire highly technical, highly specified employees based on just a casual understanding of their abilities. It's one of the most important lessons to learn concerning websites, one he really needed to learn, although a shame it had to be as expensive as it did.

2) It established a whole lot of trust between Phil and me. I had, in fact, started telling him days before that he needed to fire them, and that the company was suffering more and more damage the longer he waited. He resisted this at first, wanted to believe that they could still save it, because he had so much money wrapped into it and I didn't, so it was so much easier for me to say, "Yeah, start over and eat all the money you've already invested." I never approach resistances like that with anger; in fact, I see it as a failure on my part, that I'm not explaining adequately enough what I mean.

So I brought in experts. I got Tom to sit down and tell him how Phil was getting screwed over. You volunteered some information. The Sand guys told him how, really, if you work hard, you can put this all together in about a third of the time S----- had now spent. I finally read the contract, explained exactly to Phil how he was getting ripped off. I asked his lawyer to re-read it, and to tell him the same.

And it finally worked; and it finally got Phil to do the thing he didn't want to do, and for us to get off this horrible daily-fire-fighting schedule and finally onto something productive. And that led to the new team, the new way of interviewing I'm teaching him, finally a fully working fast schedule, and with all the people in place to actually execute it. And this has made Phil tremendously happy, and has shown him that what I promised would happen, actually HAS happened, if he would finally just fire those first damn developers already and get started on fixing the problem. And this has increased the trust he has in me tremendously now, so that I can get through a lot more minor decisions without him questioning each and every one of them.

That's good. That's great. And has accidentally created something very exciting; a brain-trust of sorts over here now (which we actually have a name for and everything -- the "Proper Thinktank"), a whole collection of what I consider brilliant minds, people with AMAZING ideas but just personal quirks that have kept them from lucrative corporate careers. I'm giving them the space, the breathing room, to let them live their quirky lives, getting them paid anyway, and asking them to step in at a senior-management position, albeit not for any pay. And not only are they saying yes, they're practically shaking our arms off, thanking us for asking them to get involved with something that makes them so excited.

It's amazing. The whole mood has changed around here. And like I said, more on this another time. But for now, I'll get started on part 2: what the actual new vision is. I think you're going to like it.

So yeah, all beginning crises now averted. And it finally gives time for Phil and I to talk. And talk. And talk and talk and talk, three or four hours every day, about what exact vision he has of this company, and what exact one I do, and what all our advisers are now telling us, not only on staff but from all these crazy people in "the industries" this month (which I'll detail in part 3, next). And that was VERY good; it was our first chance, in fact, to finally start shaping a corporate vision.

It's been part of the corporate catch-up I've been giving Phil this month; the most crammed-in MBA you could ever get, just the most basic level of education he needs to run a full corporation with six-figure budget. And a big part of it is just teaching him how to hold simultaneous visions in his head of it all -- not only long-term ( "What will let us sell our interest in this one day, and with us making a nice little chunk of money for our work at the end as a bonus?"), but medium-term too ("Where will we be in a year?") and short ("How much do we need to make this month to pay the bills, without borrowing money if we can help it?") It's a learning curve, as you know; I taught myself this from the ground-up myself in 2004, when I first decided to change careers, and it took me 200 books and 9 months. I've felt bad, throwing it all at Phil at once like this, because he's plainly getting frustrated by it all. I wish we had more time. I wish I could take it slower.

But anyway, the good news is that we HAVE started working out a much more concrete vision, finally. Here it is.

We now consider ourselves primarily as a place that offers more and more new tools to small neighborhood businesses and the self-employed. These are always very useful new tools, always unique, something none of our competitors have, and that we've either created ourselves or have partnered up for with another company. We're shooting for three the first year, and are in active talks right now about what they are. Pretty major stuff, actually; stuff that's going to blow a lot of people away if we actually pull off. But more on this in another letter. The professionalism starts right at the sign-up process, in fact; how you can be listed as an "individual" for free, but must pay $1 a month to be listed as a "business." It's just enough a commitment to show you're serious, and to show you WE'RE serious. And a nice little boot right off the bat; a way to immediately differentiate yourself from all the 19-year-old end users there.

Then throughout the year, release a series of "minor" new tools as well; better tweaks for existing features, cool new applications of new features, expanded fields in certain areas, etc. Something free for everyone, little things that just make for a better user experience, and an excuse for small social events.

Only then do we marry it to a series of fun, useful front-end sections, each mirroring the types of businesses we're competing against; a "Craigslist" section but better-designed than Craigslist; a "Yellow Pages" section but with more information-rich search results; a "MySpace" section but that won't drive you fucking crazy; a "Google Calendar" section that works...um, much like Google Calendar. Add a citizen-media section (RSS feeds of members' outside blogs), later this year married to a voter-based order like Digg, just to drive daily traffic and have something fun for the kids to do. Plus regular exhibitions of cutting-edge animation and the like, again purely to drive traffic and press.

The secret? It's all one big central database, each section designed to elegantly share standardized information with each other. Profiles are primarily tag-driven, all of them except for basic demographic info defined by the individual. This lets teens use it just like MySpace; but for businesses to add the useful info about their place people want, plus quirky details that make them stand out in searches (like a bar listing what's on their jukebox, a restaurant listing what other places their head chef has worked at). That's part of the education campaign we'll be sponsoring, instead of some of our traditional advertising, to give small businesses and freelancers ideas, show them common tags, create "clouds" for certain freelance professions, etc. Tags show up in searches; events and ads show up on posters' profiles; one big gooey synergy of rich, RICH information being shared between one section and another. Back it up with the education campaign, like I said; tutorials, mass mailings to industry professionals, hosting some industry networking events.

Add some traditional ads in business publications -- Crain's, etc, not much. Add 6 more launch parties in a year, in other cities this time, which we're fully partnering for with Unscene magazine (who have been AMAZING, by the way), five American and one in Jordan, where Phil's from of course. Two more big parties in Chicago, both of which will be launches in the future for really cool new things we have planned, but which of course I can't mention yet. And hmm, that's a plan. I think. I'm sure I'm leaving something out.

Okay, now a break. And then part 3: "how do you deal with these crazy fucking tech-industry money people who walk around with flashing dollar-bill signs in their eyes all the time?" Man, meeting with these industry people almost drove Phil and me crazy...until meeting our savior, that is. More on him later.

Hi again, Wendell, and sorry for the long break. Just got done with a business meeting, in fact, 11:30 at night at a bar called Long Room in my neighborhood. Can't yack about any of the details, of course, but we just started working out details tonight, as far as us maybe getting a five-figure chunk of money over to one of our vendors, in return for a very specific product he'll be providing us. And the best part? All three of the people at the meeting showed up on bicycles. Hell YEAH I like living in Chicago.

What is it about money, Wendell? About these little green slips of paper, issued by our government, that supposedly holds all this magical value and worth to so many people? Or even worse -- the little white slips of paper, equity statements and stock certificates, that will apparently make some people so crazy that they'll eat their own children for a couple of them? I've never dealt with this before; I've been a professional artist for the last ten years, used to dealing with projects in terms of hundreds of dollars a year, not millions. Everyone was cool back then; it was all about building a cool idea, of creating a community around that idea, and organically growing that idea while still making it as useful and updated as we could afford.

This is what Phil and I have both wanted this entire time -- to do the same exact thing I just described, but with a slightly larger budget and with slightly more at stake. So why do so many people have to make it about more than that? Why do so many people get so fucking crazy about this issue? How many people already in the industry have we met with now in the last month? 25 or so? Yeah, something like that. And for the majority of them, the moment we show up, until literally the moment we leave, it's "monetization" this and "ramping up the" that, "demographics" this and "VC" that.

I'll admit it; it's been hard. It's been confusing, and it's been overwhelming, to have these big giant huge honkin' numbers thrown at us, to have all the people around us throwing around million-dollar amounts like they're candy, like they're expecting Phil and I to gobble it all up like greedy little children. It's been over our heads, and not something we've wanted to talk about in the first place; we showed up to talk policy, to talk ideas, to talk advice. That's why we thought we were there; that's what they invited us down to that restaurant or bar or coffeehouse or office to do.

"I want to sell you some software." "I want a full-time job." "I want my company to do cross-promotion with you." Money money money; equity equity equity. What makes people get so fucking CRAZY, when they even SNIFF someone about to unexpectedly and explosively make some serious money before anyone's really expecting them to?

So thank God for Al. Yeah, Al Wasserberger. Yeah, that guy who everyone thinks is an asshole. (We don't.) Who's easily the richest and most powerful of the 25 or so people we've now met with; yeah, Inc. 500, yeah, millions of dollars. And not only that, but who invited us down to a private humidor bar on the second floor of a steakhouse in River North. Who sprung for a whole night of small-batch bourbon, imported cigars (pulled out of his private box at the club, which happened to be next to Michael Jordan's), raw oysters, introductions to supermodels moonlighting as waitresses at a humidor club for millionaires. Yeah, an amazing experience; yeah, a goddamn impressive one.

But here's the thing, and here's why Al is my new hero. Out of all these 25 people, Al was the very first one to explicitly say this out loud to us -- "You know what? If you guys want to have a small, organic, customer-centric, weird-ass share-the-love website, where you don't even CARE how much you grow from year to year, you can do that. Don't let these people push you around. That's how Craigslist became Craigslist, was through grassroots growth. That's how MySpace became MySpace. These people you're talking with are following the money. You're the ones they're following, not the other way around. You know, just as long as you're also prepared for a very public and humiliating failure. That's always the risk of your idea, and why most people don't do it."

Well, screw THAT, you know? I'm not afraid of a very public and humiliating failure. Are you kidding me? THIS HAS BEEN THE MOST THRILLING MONTH OF MY ENTIRE LIFE. Everything has been worth it, even if I never see a single penny. The stories I have ALONE have made it all worthwhile. The crazy fucking people I've met. The amazing, amazing heroes. All the surreal experiences, the oysters and cigars with millionaires at private humidor clubs in River North steakhouses, getting high with tech journalists in back alleys and finagling better articles out of them. It's just like the arts, just EXACTLY like I was when I was 25, when we were putting a show on ourselves because no one else would, when we were just throwing it together any old way we could, as cheaply as we could, just to get a good idea pushed through to full fruition. It's nothing more than that, Wendell. Just, you know, with a potential million dollars in revenue at stake the first year, if we're adding our numbers the right way (and we're pretty sure we are).

Yeah, I'll be confessional -- I cried later that night, after finally hearing something like that from Al, after hearing that from a guy who was richer and more powerful than anyone else we've had a meeting with at this point. God, it was such a HUGE 400-pound weight off my shoulders, you know? I've gotten lost over the last couple of weeks, I'll admit it; I've gotten lost. I want to do all these cool things, and I keep hearing these people saying, "That will cost you a million dollars to do," and these guys all SEEM to know what they're doing, because they all have just big giant bucketloads of money to pass around, and suddenly you think, "Wow, okay, maybe I DO need a million dollars to pull this off, these cool things I want to do." And then suddenly you're being forced to talk THEIR language -- ramping the this, exit strategy that, the demographics of the target market of the rotating banner ads based on heavy traffic patterns whatever-the-fuck.

That's not why Phil wanted to do this, and it's not why I wanted to do it. We want to build something cool, something useful, something that will make people say, "Wow, okay, I get it now, I see what you're getting at. And you're right; this is great." We're willing to put off getting paid the big bucks for now to do this; we're willing to push for self-sufficiency; we're more than willing to fail in public, and to fail spectacularly. I've been learning this month, there's a lot of people in the tech industry who aren't willing to do these things; and that THAT's the main difference between Craigslist and all the people who come in afterwards and WANT to be Craigslist.

Okay, sleepy boy, off to bed. And then...back to work. Sigh.