Many developers are up in arms about a new policy from Apple that mandates all iOS applications to be written in either a flavor of C or JavaScript. It’s original motivation is apparently to prevent Adobe’s imminent Flash-to-iOS compiler in CS5 from working, but the collateral damage is much greater than that.

There’s a wealth of cross-compilers in the wild that looks to be outlawed by the same provision. Titanium, Gambit Scheme, MonoTouch, and Unity3D are a few of the bigger ones. These layers allow you to write applications in programming languages like Scheme or C# and compile that into a native iOS applications (as well as other platforms like Android).

Lots of developers, me included, have had such a gut-turning reaction to Apple’s new policy that we have a hard time thinking and speaking rationally. The emotions take over and we start screaming “fascists!”, which isn’t very persuasive to non-developers who don’t have the same instinctual reaction. So instead, allow me to go through five (mostly) rational arguments for why this is a bad idea.

Continued…

Turning ambition into success is hard enough as it is. Whether you’re taking time to work on a project on the side or you’re launching a full-time business, it’s going to require peak personal investment. Not in terms of working crazy hours, but of dedication and perseverance.

Why would you want to pour so much of yourself into anything less than your best idea? Other ideas might seem more achievable or convenient, but if your heart and mind is elsewhere it’s all for naught.

Whatever excuse you can come up with for why you’re settling for less is probably not good enough. It’s intensely draining to give up on your dreams and you’ll not look kindly back at yourself for treading water.

Are you working on your best idea right now?

You can’t say your company is not for sale these days without incredulous stares and doubtful gasps. The big flip has become the holy grail. Worshipped to the point where non-believers are chastised, straight-faced, for refusing to give up their life’s work.

See, the new world of “sell it and do it again” belongs to the serial entrepreneur. The too-cool-to-stick-around nouveau rich of the 21st century. Staying for the long term is now seen as old-fashioned and uncool, a handknit sweater from your grandfather’s closet.

Fuck that.

Do you think Steve Jobs wants to be a serial entrepreneur? Bill Gates? Warren Buffet? Larry Ellison? All these guys put big stakes in their life’s work. Companies that they built from scratch, that they’ll champion until they can champion them no more. Sure, they may have hobby companies on the side, but for each of them, there’s one defining business, one spectacular legacy to leave behind when they’re gone.

These are my business heroes. People so dedicated to their company and its impact on society that you couldn’t pay them any amount of riches to leave. People willing to build for decades.

But, aside from the ideology behind it — the pride and satisfaction of building a company of real value to the world — there’s the financial side too. Why would you want to take a 10 times multiple of today’s earnings, if you believe you can still grow your business and you’re committed to sticking around to do it?

Why do you think you’d do a worse job than a prospective buyer of running your own business? Selling your company only makes sense if you think they can do a better job than you can. Or when you think they’re overvaluing the prospects of your company. That’s either the talk of the meek or a con man (“let’s get these suckers to overpay for this company of questionable value…”).

Flipping is a servant’s game. As the Chris Rock joke goes, Shaq is rich, the man who signs his check is wealthy. Be the man who signs the check, not the baller who takes it.

There are many reasons why someone would want to start a company. There’s the pursuit of wealth, glory, and fame, but above all, I believe most founders are searching for freedom. Freedom to run things the way they see fit, freedom to be the masters of their own domain.

But until you have profits, until you’re self-sustainable, you won’t truly have that freedom. As long as you’re beholden to other people’s money, you’re ultimately beholden to their approval.

Because we’re profitable, Jason and I get the freedom to do all sorts of “crazy” things:

• 37signals runs entirely without debt, which is apparently so uncommon that we had trouble getting net-30 terms from a vendor recently, because we couldn’t give four trade references for credit. Running a company without debt is like paying off your mortgage—liberating.
• We actually trust our employees. No expense reports, no counting vacation or sick days, no required location or work hours. We give everyone a credit card for expenses and tell them to spend it wisely. What really matters is turning out good work.
• We speak our minds — even when it’s inconvenient, controversial, or risking offense to some of our customers or partners. There’s none of the traditional self-censorship that quickly creeps in when you have to worry about what the big man thinks about your opinions.

It’s these supposedly crazy things that make me not want to give up 37signals for anything.

Now, all this is technically possible without the freedom of profitability, but it certainly wouldn’t be natural or common. Once you start thinking about how your decisions and actions might displease the men with the money, you invariably shy away from the most controversial (and best) ideas.

37signals is going to be at SXSW in full force. We’re showing up eight strong. Jason will be doing a reading from REWORK and a book signing on Saturday at 10AM on the Day Stage. Yours truly will be talking about Why You Aren’t Done Yet on Sunday at 11AM in Ballroom A with a book signing following that.

We hope to meet a ton of customers, readers, and anyone else who wants to chat at SXSW. If you see anyone at the conference with a 37signals badge, please walk up and say hi. And please do bring your copy of REWORK if you want it signed too.

Looking forward to seeing ya’all in Austin.

Startups need people able and willing of doing the actual work. They need programmers, designers, and eventually folks to do marketing, support, and more. What they don’t need, though, is someone who’s just going to be The Idea Guy.

You know the type. It’s the “this thing is going to be Facebook meets Flickr, but for dogs! If we can just get 1% of the online dog market, we’ll be rich!” spiel. All idea, usually no money, and hardly any functional skills that’ll help build or launch the damn thing.

On the face and the facts of it, it’d be easy to turn down The Idea Guy. He wants you to work for very little or free in return for a smaller-than-his slice of the pie in the end. That end very rarely happens. But the energy and the big dreams can be dangerously alluring. I know, I fell for it more than once.

The truth is that most everyone has plenty of ideas that could work out to be great businesses. The kicker is most often the right execution, that they’d be responsible for anyway, at the right time, which is almost impossible to predict. The value of The Perfect Idea is very small indeed.

That doesn’t mean it’s useless to have big ideas and plenty of enthusiasm. If you’re that guy, you’ve got a great start. Now pick up a functional skill and help build it your damn self.

Joel has decided to chase venture capital for StackOverflow, but I can’t exactly figure out why. He lists six benefits that just don’t compute under even light scrutiny:

1. The Answers market is in a land grab mode
Unlike eBay, where there’s a general market for goods and you get huge network effects from having a critical mass of buyers and sellers, StackOverflow is all about niches. People who are searching for “how to make sql server not go slow?” aren’t likely to bleed over to “how to make swedish meatballs?”.

This means that you’ll have to fight for every niche. Similar to how general forums would have to fight for every niche. Just because you have a forum site that’s big for gamers, you won’t have much of an edge attracting foodies.

Finally, it’s not like this is a new idea with no other entrants. Look at Yahoo Answers for a site that’s still up with a similar model and look at Google Answers for another that couldn’t be turned into a worthwhile business and closed.

2. Stack Overflow is like Starbucks
It really isn’t. Starbucks can use capital efficiently because they have big capital expenditures securing land, building out stores, and purchasing coffee machines. Where’s the capital intensity part of starting another answers site? Adding another server? Coming up with a new design?

It doesn’t seem like Stack Overflow can efficiently use big money for anything but advertising itself. Which is kinda funny when the whole business is about getting page views to sell for ad crumbs. It also rings very much like dot-com. Remember when all you had to do was get eyeballs? Oh, it’s free? Who cares, let’s make it up on volume!

3. Stack Overflow wants to get on Techcrunch
If you’re listing the publicity of “Stack Overflow raises $10M in Series A by Fancy Schmancy VC” as the 3rd pro for taking money, you’re bound to be in trouble. The Techcrunch post you’re going to get from this is going to scroll off the front page in 4 hours and nobody who’s actually going to use your service is going to care.

Do you think people looking for an answer to “how do I get the three gold rings in zelda?” is going to give a hoot who’s money you’re burning to provide that forum? Or even that the advertisers you’re hoping to attract is going to look at anything else than CPM and demographics for a clue on whether to invest? No.

4. The investor will give you advice, connections, and introductions
They may, but most of the introductions your typical investor is going to give you is how to get you out in 3-5 years. You can find a lot of advice in many places. Rarely is the quality of the advice associated with having money involved of largely superior quality.

And if you end up building something of considerable value, then the connections and introductions will come all by themselves. You usually have to work to fight them off with a stick when things are going great. And getting an intro to Mr. Very Important Person before you have anything of material value is usually not going to give you much anyway.

5. Taking money means big exit or IPO
I’d argue the opposite. When you take money, your exit is bound to be smaller unless you’re playing the Web 2.0 lottery game (where a few lucky contestants gets bought for sums completely uncorrelated to business fundamentals). Taking money means giving up equity, which means there’ll be less left over if you happen to build something that’s valuable enough for others to buy.

And I don’t know if you’ve heard, but the IPO markets aren’t all that interested in eyeball companies without the numbers to back them up any more. Doesn’t matter how many letters of the alphabet you’ve used for series whatever funding before you got there.

If you can build a great, profitable business, you’ll have all the options to sell or go IPO. Taking VC only complicates that.

6. Taking VC will make your company successful
This one is funny. So if you’re not looking to take VC and play the Web 2.0 lottery or aim for an early exit, you’re just in it for “personal aggrandizement”. If you take the money, you just want the best for your business. Spot the disconnect here.

Now even given all this, there’s actually still an argument for why Joel should take the money. It’ll probably lower the chances of Stack Overflow ultimately succeeding as a long-term sustainable business, but if he has eyed that he has a hot property right now, it’ll be a good time to take some money off the table.

A fool and his money will soon be departed applies equally to venture capitalists as it does to everyone else. If Joel and co. can negotiate a deal with Sand Hill road to give them a nice payout as part of the deal, this might well be even better than trying to shop around Stack Overflow for a sale that it’s probably premature for.

Much better to take a small slice of the proceeds from a “if this just get 1% of the billion dollar advertising market” than to take the slice from “how much money did you make for the past 12 months?” of a strictly look-at-the-books sale.

Go cherries, go!

I love my iPhone and I love Apple (cue images of flag pins and “I love muh countray!”), but I believe they’re blowing it with the App Store gate keeping. That’s of course not a new opinion. Developers left and right have been decrying the broken process. But there’s nothing like feeling it on your own bones to make the point.

We have a couple of new features in the wing for Campfire. They’ve been done for more than 10 days now. Why haven’t we released them yet? Because the iPhone app Ember needed to have a simple regular expression updated to support the features. We really like Ember, so we decided that holding back the features until this pro forma update went through was prudent. We’re still waiting.

This has made me think about all the ways the app store process sucks and how little we get back in return. The argument I keep hearing for why this terrible process is worth it is quality control. Here’s a breakdown of each argument:

• Applications will be more stable: No they won’t. Echophone still crashes on me all the time. It’s not like the iPhone is immune to crash bugs. And why would it be? You’re writing native Objective-C here. Shit is going to crash every now and then. No 10 minute look-over by a App Store clerk is going to help that.
• The App Store will be free of malware: That’s certainly no given. If you really wanted to be evil, you could very well hide your malice underneath a cute game and have a time bomb or a remote trigger installed. Do you think the App Store clerks are combing through source code to look for security issues? Ha!
• Only good stuff in the App Store: Ha! The App Store has some 140K+ applications. I can guarantee you that the bulk of that is less than average. There are some 100 fart apps for christ sake!

We’re paying for the inconvenience of quality control without the quality part. In fact, lots of software has lower quality because of the App Store process. Developers can’t easily get bug fixes out and they certainly don’t release new versions as often as they otherwise would. This harks back to the era where software was really cumbersome to release on CDs, so you did it much less frequently.

Contrast this with OS X and the web. Both platforms are much more open and on a mac you have very little trouble with stability or malware or even quality. In general, the market is pretty good at sorting this stuff out. If you make a crappy application, people don’t buy or recommend it. And OS X seems to be holding up well as a secure platform compared to, say, Windows, so malware isn’t much of a concern either.

What I think Apple should do instead is to reserve the power to nuke apps that prove troublesome. Have a “if you fuck it up, we’ll yank it” policy rather than a “we’ll review everything poorly and slowly and still not catch it all” policy. They’d be able to get by with a much smaller App Store clerk staff, developers would be thrilled to escape the needless gate keeping, and consumers would enjoy more applications updated more frequently.

What’s there to lose except for the feeling of powah?

“When is it going to be done?” is a reasonable question and we as software developers should try to come up with the best answer we can based on our experience and analysis. What we should not do, however, is treat our answer as solemn oath.

When you treat estimates as promises instead of guesses, you bind your worth as a worker to it. If you do not meet your own deadline, you are a failure. And since nobody likes to be a failure, they’ll indulge in risky behavior to avoid it, like burning the midnight oil and checking in bad code with scanty or no tests.

Rushing to meet your estimate promise once or twice might be bearable, but it’s ultimately unsustainable. Software development is inherently unpredictable. There are just too many moving parts and ice tips that turn out to be icebergs.

If you treat the estimate as a “best guess based on the limited information available to me before I start the work”, though, you’ll change the frame and break the cycle of deadline anguish. Now the task becomes collaborative and you can share new discoveries with the stakeholders.

Found out that doing the feature as originally designed requires changing some fundamental infrastructure that’ll add another two days to your one day estimate? Maybe it’s not worth it any more. Ask the stakeholder if he’s still interested in the feature when it costs three days instead of one. Or if there’s a way to simplify it such that the infrastructure change is not necessary.

That’s the true value of estimates. That it sets up conversational constraints that can be used as boundaries for trading concessions. Not that they’re nails for your own self-erected cross.