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If you do have to leave grad school, in the worst case it won't be for too long. If a startup fails, it will probably fail quickly enough that you can return to academic life. And if it succeeds, you may find you no longer have such a burning desire to be an assistant professor.

If you want to do it, do it. Starting a startup is not the great mystery it seems from outside. It's not something you have to know about "business" to do. Build something users love, and spend less than you make. How hard is that?

Notes

[1] Google's revenues are about two billion a year, but half comes from ads on other sites.

[2] One advantage startups have over established companies is that there are no discrimination laws about starting businesses. For example, I would be reluctant to start a startup with a woman who had small children, or was likely to have them soon. But you're not allowed to ask prospective employees if they plan to have kids soon. Believe it or not, under current US law, you're not even allowed to discriminate on the basis of intelligence. Whereas when you're starting a company, you can discriminate on any basis you want about who you start it with.

[3] Learning to hack is a lot cheaper than business school, because you can do it mostly on your own. For the price of a Linux box, a copy of K&R, and a few hours of advice from your neighbor's fifteen year old son, you'll be well on your way.

[4] Corollary: Avoid starting a startup to sell things to the biggest company of all, the government. Yes, there are lots of opportunities to sell them technology. But let someone else start those startups.

[5] A friend who started a company in Germany told me they do care about the paperwork there, and that there's more of it. Which helps explain why there are not more startups in Germany.

[6] At the seed stage our valuation was in principle $100,000, because Julian got 10% of the company. But this is a very misleading number, because the money was the least important of the things Julian gave us.

[7] The same goes for companies that seem to want to acquire you. There will be a few that are only pretending to in order to pick your brains. But you can never tell for sure which these are, so the best approach is to seem entirely open, but to fail to mention a few critical technical secrets.

[8] I was as bad an employee as this place was a company. I apologize to anyone who had to work with me there.

[9] You could probably write a book about how to succeed in business by doing everything in exactly the opposite way from the DMV.

Thanks to Trevor Blackwell, Sarah Harlin, Jessica Livingston, and Robert Morris for reading drafts of this essay, and to Steve Melendez and Gregory Price for inviting me to speak.

A Unified Theory of VC Suckagepad

A couple months ago I got an email from a recruiter asking if I was interested in being a "technologist in residence" at a new venture capital fund. I think the idea was to play Karl Rove to the VCs' George Bush.

I considered it for about four seconds. Work for a VC fund? Ick.

One of my most vivid memories from our startup is going to visit Greylock, the famous Boston VCs. They were the most arrogant people I've met in my life. And I've met a lot of arrogant people. [1]

I'm not alone in feeling this way, of course. Even a VC friend of mine dislikes VCs. "Assholes," he says.

But lately I've been learning more about how the VC world works, and a few days ago it hit me that there's a reason VCs are the way they are. It's not so much that the business attracts jerks, or even that the power they wield corrupts them. The real problem is the way they're paid.

The problem with VC funds is that they're funds. Like the managers of mutual funds or hedge funds, VCs get paid a percentage of the money they manage: about 2% a year in management fees, plus a percentage of the gains. So they want the fund to be huge-- hundreds of millions of dollars, if possible. But that means each partner ends up being responsible for investing a lot of money. And since one person can only manage so many deals, each deal has to be for multiple millions of dollars.

This turns out to explain nearly all the characteristics of VCs that founders hate.

It explains why VCs take so agonizingly long to make up their minds, and why their due diligence feels like a body cavity search. [2] With so much at stake, they have to be paranoid.

It explains why they steal your ideas. Every founder knows that VCs will tell your secrets to your competitors if they end up investing in them. It's not unheard of for VCs to meet you when they have no intention of funding you, just to pick your brain for a competitor. This prospect makes naive founders clumsily secretive. Experienced founders treat it as a cost of doing business. Either way it sucks. But again, the only reason VCs are so sneaky is the giant deals they do. With so much at stake, they have to be devious.

It explains why VCs tend to interfere in the companies they invest in. They want to be on your board not just so that they can advise you, but so that they can watch you. Often they even install a new CEO. Yes, he may have extensive business experience. But he's also their man: these newly installed CEOs always play something of the role of a political commissar in a Red Army unit. With so much at stake, VCs can't resist micromanaging you.

The huge investments themselves are something founders would dislike, if they realized how damaging they can be. VCs don't invest $x million because that's the amount you need, but because that's the amount the structure of their business requires them to invest. Like steroids, these sudden huge investments can do more harm than good. Google survived enormous VC funding because it could legitimately absorb large amounts of money. They had to buy a lot of servers and a lot of bandwidth to crawl the whole Web. Less fortunate startups just end up hiring armies of people to sit around having meetings.

In principle you could take a huge VC investment, put it in treasury bills, and continue to operate frugally. You just try it.

And of course giant investments mean giant valuations. They have to, or there's not enough stock left to keep the founders interested. You might think a high valuation is a great thing. Many founders do. But you can't eat paper. You can't benefit from a high valuation unless you can somehow achieve what those in the business call a "liquidity event," and the higher your valuation, the narrower your options for doing that. Many a founder would be happy to sell his company for $15 million, but VCs who've just invested at a pre-money valuation of $8 million won't hear of that. You're rolling the dice again, whether you like it or not.

Back in 1997, one of our competitors raised $20 million in a single round of VC funding. This was at the time more than the valuation of our entire company. Was I worried? Not at alclass="underline" I was delighted. It was like watching a car you're chasing turn down a street that you know has no outlet.

Their smartest move at that point would have been to take every penny of the $20 million and use it to buy us. We would have sold. Their investors would have been furious of course. But I think the main reason they never considered this was that they never imagined we could be had so cheap. They probably assumed we were on the same VC gravy train they were.

In fact we only spent about $2 million in our entire existence. And that gave us flexibility. We could sell ourselves to Yahoo for $50 million, and everyone was delighted. If our competitor had done that, the last round of investors would presumably have lost money. I assume they could have vetoed such a deal. But no one those days was paying a lot more than Yahoo. So unless their founders could pull off an IPO (which would be difficult with Yahoo as a competitor), they had no choice but to ride the thing down.