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cwilbur

76 karma · joined March 28, 2007

cwilbur@chromatico.net
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cwilbur··on How long do Y-Comb startups live before getting acquired or dissolving?
Getting rejected by YC is not failure. YC has specific things they're looking for, and only so many resources to go around; getting rejected means that (a) you didn't match what they were looking for or (b) you didn't seem as promising as some of the other people who applied.

A friend of mine is a marathon runner who usually comes in under 3 hours. It turns out that there are enough people in that category that the Boston Marathon offers slots by lottery, and this year he wasn't one of them. Not getting a slot in the Boston Marathon doesn't mean you can't finish the race; it just means you have to find a different place to run.

cwilbur··on What is your stimulant of choice to keep you working through the night?
If I need a stimulant to keep me awake, I go to sleep.

Pulling an all-nighter when I'm already in sleep debt only produces code that sucks. The next day, I'm too tired to be functional and I've got a bunch of code that needs to be thrown out and rewritten. Sleep is a better use of time.

cwilbur··on What's the best thing you could be working on, and why aren't you?
The UI for the project I pitched to YC. It's one of the two hard interesting problems in the project, and it's the one that has the most effect on the success or failure of the project.

(There's another hard interesting problem, but it's the sort of thing that can be tweaked and tuned.)

I'm not working on it at this moment because I'm at my day job looking busy, and I don't want to do any concrete work on that project here because of IP issues. (Any work I do off company time is not theirs, and I have that in writing; any work I do on company time is theirs. One of the advantages of working for a very corporate boss is that "company time" is defined as 9 am to 5 pm.)

I'm not working on it in code right now in general because it's still percolating in my backbrain while I am picking off a few of the more straightforward problems to get myself going. And because it's big and scary, and code seems more permanent than sketches.

cwilbur··on Cambridge YC Alums: How'd you spend your funding?
$500 for incorporation is a very low figure for some states. If I remember right, the cost of incorporation as an LLC in Massachusetts (which is what I was researching at the time, because that's where I am) runs about $1000 between what you end up owing the state and what you end up owing the lawyer; incorporating as an LLC in any other state means you need to register as a foreign corporation with the state if you intend to do business in that state (in MA: lease property as a corporation, pay salaries as a corporation, own property as a corporation), which in Massachusetts runs about $1000 between what you end up owing the state and what you end up owing the lawyer.

Other states may be more lenient on when you need to register as a foreign corporation or cost less to incorporate or register as a foreign corporation. Also, for some startup models, it can make sense to incorporate in Delaware when you start development and then worry about the whole foreign-corporation thing when it's time to start hiring employees rather than adding partners.

cwilbur··on Justin is having sex NOW on justin.tv
Right - that means that instead of having a camera in whatever room Sean Patrick is in, and long stretches of dead time when he's somewhere that can't be wired for filming, you see Justin's environment all the time no matter where he is. Bandwidth also means that it can be streaming video rather than a web cam that updates every 20 seconds or so.

I'm not sure why this is supposed to be compelling. The presentation has changed, but the content hasn't. Or is it that the time is right, and there are enough voyeuristic people and enough revenue to be made from Google ads to make it worth doing?

cwilbur··on What mistakes of yours do you really regret. Why?
Sometimes I really regret the computer science major. The things I learned were right, but the credential was wrong -- it basically certified me as sufficiently trained to work in IT cubicle hell. (It was really a math degree at its core, and it made me a problem-solving generalist, which is not what Industry wants.) I considered dropping it, but it was so easy to do what I needed for the additional credential -- it was a matter of two classes I wouldn't otherwise have taken.

I regret not recognizing the intensely political nature of my masters' degree program before it was too late to do anything about it. I've thought about going back to a different school, getting the PhD, and trying to scale the ivory tower, but I don't think the payoff I can realistically expect is worth the investment. It's not like a PhD in Renaissance music theory makes you any more employable in the "real world," and academic positions are few and far between, and there is so much of a surplus of good professors that some of the best are eking out a living teaching as adjuncts at community college.

cwilbur··on Justin is having sex NOW on justin.tv
You know, this whole televised life thing got old when it was Sean Patrick Live, nearly a decade ago. Is there something I'm missing about justin.tv?
cwilbur··on Who Got Accepted For Interviews? - Post here if you did
That they think can succeed in YC's particular approach to startup building, you mean.

pg has a fairly clear set of factors that he thinks indicate success -- being physically in a startup hub, for instance; having multiple founders; the sort of thing he recommends in his essays. Rejection from YC can mean that they don't think the project can succeed; it can also mean that they don't think the project, even if it succeeds, will give them the kind of return on investment they want.

So (to make the math easy) suppose they have a company that they own 10% of, that they've invested $15K in. This means that for them to break even, the company has to eventually have a value of $150,000. A rule of thumb for business valuation is that the sale price of the business is 3 to 5 times its annual earnings -- which means that the business has to earn $30,000 a year to $50,000 a year in profit for that to be worthwhile.

Now, a micro-ISV, for instance, that treats its founders' salaries (appropriately) as expenses may be a terrifically successful business from the point of view of the founders, especially if they pay themselves acceptably well and like the working conditions. But unless it makes $30,000 to $50,000 in profits a year, it's a losing proposition for Y Combinator.

There are other ways it can be a winning proposition without those profits -- if it's just before the tipping point of a big trend, or if the founders are especially skillful. A company that isn't making any profits at the moment but has the potential to make really big profits, or the potential to be sold for a lot of money, might be a worthwhile investment.

cwilbur··on How many teams who live in the SF Bay Area opted to wait until the winter round?
I didn't bother with the winter round because I live in Massachusetts and have family and friends mostly in New England, and it seemed silly to move across the country rather than waiting six months and moving across the state.
cwilbur··on What is the best time of year to launch a site?
Depends on the site. A site offering customized Christmas cards won't do well immediately if you launch in January; a site offering something useful for preparing for college won't do well immediately if you launch in November.

Launch the site as soon as it's ready to be launched. You'll drive yourself crazy trying to micro-optimize and asking yourself if you'll get more traffic if you launch on Tuesday or Saturday.

cwilbur··on rejected!
Well, slow growth while I work at my day job.

$10-$15K is the difference between being able to quit my day job and get the company going in 3 months and having to keep my day job and get the company going in 9 months to a year.

And if I need to keep the day job, slow sustainable growth -- meaning I can project income, and project reasonably accurately when I can quit my day job -- is much better than a spike that I need to deal with in crisis mode.

cwilbur··on Vote up if you're rejected but will still proceed
I knew I was a long shot. I had two strikes against me in that I'm a single founder and I'm more interested in building a company I want to work for than in becoming rich at it -- so my interests and investors' interests don't line up.

Of course I'm still proceeding -- Y Combinator money was a means to an end, and not an end in itself.

cwilbur··on rejected!
Rejected here too. I'm not surprised; it was a long shot to begin with, and I don't think my goals as a founder and their goals as investors really lined up. It probably didn't help that I'm a sole founder, either.

Time for Plan B. Powerball tickets. Er, I mean, the slowly growing micro-ISV approach.

cwilbur··on What catches your attention in a job listing?
Positively? the job listing tells me what I want to know in order to determine whether I want to find out more about the position (what am I doing, what tools do they provide, who am I working for, where are they located?)

Negatively? Evasiveness ("one of the leading X"), attempting to impress me with things I don't care about or am likely to consider negative ("a Fortune 500 company," "one of the largest Visual Basic code bases in the industry"), signs of buzzword bingo or technical incompetence ("must have significant experience in PERL, Python, PHP, HTML, CSS, Javascript, Java, ASP, C#, ColdFusion", "must have 10+ years of experience with Windows XP"), signs that the accounting department and glossy magazines are choosing technologies (any mention of ColdFusion or Dreamweaver).

Yeah, the latter list is much longer. It's a lot easier to do things wrong than to do them right.

cwilbur··on If Microsoft made an offer to buy your startup would you sell?
Microsoft's money is as green as any other money I'm likely to be offered for the software; my decision would depend on other things like the amount they were offering and the terms of the deal.

For instance, "must move to Redmond," "must sign a non-compete contract," and "must be developed in Microsoft proprietary languages and for Microsoft proprietary platforms" would all be deal-killers.

My goal here is not to be rich, necessarily, but to create the kind of company I want to work for and make it profitable enough that I don't need to work for any other company. If any buyer, even Microsoft, offered the sort of environment I wanted to work in, plus enough money that I could walk away and not need to work another corporate IT job again if the environment changed, I'd sell.

And some of this is predicated on the experience of a good friend of mine, whose team mostly bootstrapped a very profitable company, then sold it to their largest corporate customer; suddenly they were getting guaranteed salaries, and they got to watch their project earn tens of millions in revenue, but the working environment was politically toxic and the company (now a wholly-owned subsidiary) was the football in constant turf wars, and (in retrospect, especially after seeing the first two years' income from the project) the price they asked was about 1/10 of what it should have been.

I can't alter the turf wars and political toxicity in certain corporations, but I can make sure I ask a price for my company that means I can stand up and walk away with no financial worries if they develop.

cwilbur··on YC Deadline: Does the "midnight" mean between April 1st and 2nd...or 2nd and 3rd?
Oops. Teach me to post before reading all the threads.... I thought the deadline was last night, not tonight.

cwilbur··on How did you answer the final application question?!
I couldn't think of anything that didn't sound trite when I first filled out the form, so I left it blank and decided to come back to it later.

(As far as I'm concerned it's a long shot. I don't think my idea and my goals for my business line up that well with what YC is really looking for, based on what they've done in the past. So I filled out the form more for myself than for them.)

But then I thought of the best answer to that question -- the most personally meaningful thing I've discovered, something that I don't think anyone else has ever noticed -- over the weekend, and only realized this morning that the deadline had whooshed right by while I was sleeping.

Oops.

cwilbur··on Ask Paul: Is "smart" enterprise software interesting?
The problem with enterprise software (at least as I understand it) is that it's frequently bespoke data processing software, written in-house -- it's not the sort of thing that you can do once and sell to multiple clients, it's the sort of thing that needs to be customized for each client.

I think that it has the potential to be the most interesting software to work on, because a lot of it is about real things, but because of its bespoke nature the only way to get at the really interesting bits is to work for the company that it forms part of the infrastructure for. And once you're in that situation, you're dependent on (probably very risk-averse) management for support for doing "smart" things with the software.

cwilbur··on Work and Wives
The reason to start a startup when you're young and single is because you have no commitments. Once you have kids, you can't afford to take that kind of chance with your life because you're also responsible for their lives. But a spouse/significant other who's genuinely supportive is like a partner in the company who's sharing your equity -- if you make it big, he or she makes it big too.

On the other hand, a spouse or significant other who's not supportive -- or who means to be supportive but who doesn't actually offer much support, which is worse -- can put enough of a drag on things to make the company fail.

And as brlewis notes, a lot depends on the pace you're trying to run the company at. If you're using the traditional VC-funded web startup model and working 100-hour weeks in the hacking zone, your relationship with your spouse/SO is going to suffer. If you're using the consulting/micro-ISV model and expanding the business gradually, it's likely to put a lot less strain on the relationship.

cwilbur··on Engineering as a profession?
Engineering can be a lifelong profession, but the longer you spend trying to be a good engineer the more likely you are to work for someone who just Doesn't Get It. Once a company gets to be a certain size, especially if the people in charge aren't technically skilled, politics and perception trumps physical laws; an engineer who can't make the case for a solution on technical grounds (this is the cleanest way to solve the problem) or on business grounds (this is the cheapest way to solve the problem, and we save $200K a year by doing it this way over the way we originally thought of) but on political grounds (this is neither clean nor cheap, but it uses this buzzword-compliant tech and will increase your budget by $1.5M and require 2 people to support) is not likely to be a happy engineer.
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