But I think the main reason VCs like splitting deals is the fear of looking bad. If another firm shares the deal, then in the event of failure it will seem to have been a prudent choice—a consensus decision, rather than just the whim of an individual partner.
Investing is not covered by antitrust law. At least, it better not be, because investors regularly do things that would be illegal otherwise. I know personally of cases where one investor has talked another out of making a competitive offer, using the promise of sharing future deals.
In principle investors are all competing for the same deals, but the spirit of cooperation is stronger than the spirit of competition. The reason, again, is that there are so many deals. Though a professional investor may have a closer relationship with a founder he invests in than with other investors, his relationship with the founder is only going to last a couple years, whereas his relationship with other firms will last his whole career. There isn't so much at stake in his interactions with other investors, but there will be a lot of them. Professional investors are constantly trading little favors.
Another reason investors stick together is to preserve the power of investors as a whole. So you will not, as of this writing, be able to get investors into an auction for your series A round. They'd rather lose the deal than establish a precedent of VCs competitively bidding against one another. An efficient startup funding market may be coming in the distant future; things tend to move in that direction; but it's certainly not here now.
The reason startups work so well is that everyone with power also has equity. The only way any of them can succeed is if they all do. This makes everyone naturally pull in the same direction, subject to differences of opinion about tactics.
The problem is, larger scale investors don't have exactly the same motivation. Close, but not identical. They don't need any given startup to succeed, like founders do, just their portfolio as a whole to. So in borderline cases the rational thing for them to do is to sacrifice unpromising startups.
Large-scale investors tend to put startups in three categories: successes, failures, and the "living dead"—companies that are plugging along but don't seem likely in the immediate future to get bought or go public. To the founders, "living dead" sounds harsh. These companies may be far from failures by ordinary standards. But they might as well be from a venture investor's point of view, and they suck up just as much time and attention as the successes. So if such a company has two possible strategies, a conservative one that's slightly more likely to work in the end, or a risky one that within a short time will either yield a giant success or kill the company, VCs will push for the kill-or-cure option. To them the company is already a write-off. Better to have resolution, one way or the other, as soon as possible.
If a startup gets into real trouble, instead of trying to save it VCs may just sell it at a low price to another of their portfolio companies. Philip Greenspun said in Founders at Work that Ars Digita's VCs did this to them.
Most people would rather a 100% chance of $1 million than a 20% chance of $10 million. Investors are rich enough to be rational and prefer the latter. So they'll always tend to encourage founders to keep rolling the dice. If a company is doing well, investors will want founders to turn down most acquisition offers. And indeed, most startups that turn down acquisition offers ultimately do better. But it's still hair-raising for the founders, because they might end up with nothing. When someone's offering to buy you for a price at which your stock is worth $5 million, saying no is equivalent to having $5 million and betting it all on one spin of the roulette wheel.
Investors will tell you the company is worth more. And they may be right. But that doesn't mean it's wrong to sell. Any financial advisor who put all his client's assets in the stock of a single, private company would probably lose his license for it.
More and more, investors are letting founders cash out partially. That should correct the problem. Most founders have such low standards that they'll feel rich with a sum that doesn't seem huge to investors. But this custom is spreading too slowly, because VCs are afraid of seeming irresponsible. No one wants to be the first VC to give someone fuck-you money and then actually get told "fuck you." But until this does start to happen, we know VCs are being too conservative.
Back when I was a founder I used to think all VCs were the same. And in fact they do all look the same. They're all what hackers call "suits." But since I've been dealing with VCs more I've learned that some suits are smarter than others.
They're also in a business where winners tend to keep winning and losers to keep losing. When a VC firm has been successful in the past, everyone wants funding from them, so they get the pick of all the new deals. The self-reinforcing nature of the venture funding market means that the top ten firms live in a completely different world from, say, the hundredth. As well as being smarter, they tend to be calmer and more upstanding; they don't need to do iffy things to get an edge, and don't want to because they have more brand to protect.
There are only two kinds of VCs you want to take money from, if you have the luxury of choosing: the "top tier" VCs, meaning about the top 20 or so firms, plus a few new ones that are not among the top 20 only because they haven't been around long enough.
It's particularly important to raise money from a top firm if you're a hacker, because they're more confident. That means they're less likely to stick you with a business guy as CEO, like VCs used to do in the 90s. If you seem smart and want to do it, they'll let you run the company.
Raising money is a huge time suck at just the point where startups can least afford it. It's not unusual for it to take five or six months to close a funding round. Six weeks is fast. And raising money is not just something you can leave running as a background process. When you're raising money, it's inevitably the main focus of the company. Which means building the product isn't.
Suppose a Y Combinator company starts talking to VCs after demo day, and is successful in raising money from them, closing the deal after a comparatively short 8 weeks. Since demo day occurs after 10 weeks, the company is now 18 weeks old. Raising money, rather than working on the product, has been the company's main focus for 44% of its existence. And mind you, this an example where things turned out well.
When a startup does return to working on the product after a funding round finally closes, it's as if they were returning to work after a months-long illness. They've lost most of their momentum.
Investors have no idea how much they damage the companies they invest in by taking so long to do it. But companies do. So there is a big opportunity here for a new kind of venture fund that invests smaller amounts at lower valuations, but promises to either close or say no very quickly. If there were such a firm, I'd recommend it to startups in preference to any other, no matter how prestigious. Startups live on speed and momentum.
The reason funding deals take so long to close is mainly that investors can't make up their minds. VCs are not big companies; they can do a deal in 24 hours if they need to. But they usually let the initial meetings stretch out over a couple weeks. The reason is the selection algorithm I mentioned earlier. Most don't try to predict whether a startup will win, but to notice quickly that it already is winning. They care what the market thinks of you and what other VCs think of you, and they can't judge those just from meeting you.