After watching a bazillion venture pitches, I’ve come to the conclusion that every VC Pitch should end the same way — with the ask. If you want to crescendo into it, feel free to summarize why it is your technology is life changing, but finish with the ask — “we are looking to raise six million dollars.” Don’t beat around the bush. Come right out and ask for the money. After all, that’s what you’re there for.

There are a number of reasons VCs want to hear what you’re raising. And it isn’t just the obvious one. Yes, it is helpful to know how much money a company is hoping you will invest. But there are other more valuable pieces of information that come out of the ask.

First of all, the amount of money you are raising is a good general indicator of how much you think the company is worth. I was in a pitch once learning about pretty interesting but pretty early stage technology. From where I sat, it seemed to me that the company could use single digit millions to take the technology to the next step. Yet, when we got to the slide that stated how much the company was raising, I learned that they were hoping to raise more than $50M. By my assessment, $50M would buy the vast majority of the company. Clearly the company felt differently — they were hoping to sell closer to 20% of the company. It certainly refocused the conversation on what the company felt was the justification for such a high valuation and led to a very interesting discussion of the underlying economics of the company’s business.

The thing I find most interesting about how much money a company is raising is not the actual number itself, but rather the conversation about how the company arrived at that number. What is interesting to me is what the company plans on doing with that money? What are the milestones the company can reach with that much money? Could they do it for less? What would they do if they had more money?

For me, the right question isn’t “how much money do you want to raise?” The right question is “how much money should you raise?” Ask some entrepreneurs and they will tell you, the right amount of money to raise is as much as they possibly can (some recent monster financings suggest that strategy). That makes no sense to me. The right amount of money to bring into the company is enough to reach sufficient milestones to raise more money at a higher price at a future date (or, in some rare cases, enough to get to cash flow positive). If all goes well, the money I invest will be used to drive all sorts of risk out of the business, enabling the Company to raise the next round at a much higher valuation.

Figuring out the right amount to raise is more art than science but can have a big impact on the Company. If you raise too little money, you may run out before you have proven the business sufficiently to raise additional capital. In other words, raising too little money can be fatal. On the other hand, if you raise too much money early on, you could well be selling off too much of the company for too little capital. Companies should leverage early stage venture money to drive up the value of the company (by proving out as much of the business as quickly as possible), so that the next time the company fundraises, they will be able to bring in larger amounts of money while suffering smaller amounts of dilution.

Unfortunately, the perfect amount of money to raise is not always obvious. So the question isn’t whether a company is raising the “right” amount of money. The question is, “why is the company raising the amount of money it is raising?” A great deal can be learned about a company from their answer to that question. So when you go out to raise money, be prepared to not only answer how much you are hoping to raise, but also why?

After watching a bazillion venture pitches, I’ve come to the conclusion that every VC Pitch should end the same way — with the ask. If you want to crescendo into it, feel free to summarize why it is your technology is life changing, but finish with the ask — “we are looking to raise six million dollars.” Don’t beat around the bush. Come right out and ask for the money. After all, that’s what you’re there for.

There are a number of reasons VCs want to hear what you’re raising. And it isn’t just the obvious one. Yes, it is helpful to know how much money a company is hoping you will invest. But there are other more valuable pieces of information that come out of the ask.

First of all, the amount of money you are raising is a good general indicator of how much you think the company is worth. I was in a pitch once learning about pretty interesting but pretty early stage technology. From where I sat, it seemed to me that the company could use single digit millions to take the technology to the next step. Yet, when we got to the slide that stated how much the company was raising, I learned that they were hoping to raise more than $50M. By my assessment, $50M would buy the vast majority of the company. Clearly the company felt differently — they were hoping to sell closer to 20% of the company. It certainly refocused the conversation on what the company felt was the justification for such a high valuation and led to a very interesting discussion of the underlying economics of the company’s business.

The thing I find most interesting about how much money a company is raising is not the actual number itself, but rather the conversation about how the company arrived at that number. What is interesting to me is what the company plans on doing with that money? What are the milestones the company can reach with that much money? Could they do it for less? What would they do if they had more money?

For me, the right question isn’t “how much money do you want to raise?” The right question is “how much money should you raise?” Ask some entrepreneurs and they will tell you, the right amount of money to raise is as much as they possibly can (some recent monster financings suggest that strategy). That makes no sense to me. The right amount of money to bring into the company is enough to reach sufficient milestones to raise more money at a higher price at a future date (or, in some rare cases, enough to get to cash flow positive). If all goes well, the money I invest will be used to drive all sorts of risk out of the business, enabling the Company to raise the next round at a much higher valuation.

Figuring out the right amount to raise is more art than science but can have a big impact on the Company. If you raise too little money, you may run out before you have proven the business sufficiently to raise additional capital. In other words, raising too little money can be fatal. On the other hand, if you raise too much money early on, you could well be selling off too much of the company for too little capital. Companies should leverage early stage venture money to drive up the value of the company (by proving out as much of the business as quickly as possible), so that the next time the company fundraises, they will be able to bring in larger amounts of money while suffering smaller amounts of dilution.

Unfortunately, the perfect amount of money to raise is not always obvious. So the question isn’t whether a company is raising the “right” amount of money. The question is, “why is the company raising the amount of money it is raising?” A great deal can be learned about a company from their answer to that question. So when you go out to raise money, be prepared to not only answer how much you are hoping to raise, but also why?

It’s great to hear stories like the one where Andy Bechtolsheim handed the Google founders a $100,000 check before they even set up their bank account. Convince an angel to invest and you’re off to the races! However, what many aspiring entrepreneurs don’t know is that after the one or two page term sheet there are dozens of pages of documents that go into even an angel financing.

Since law firms have templates for these deals you might think it’s no harder than copying and pasting. The problem is there are lots of different templates floating around law firms, and a countless number of terms that could be changed. Many of these terms really don’t make too big of difference, or if they do their effects are so hard to anticipate that arguing over them isn’t worth the time. Lawyers get paid by the hour so they have an incentive to find terms they don’t like (and there are always terms to not like). So lawyers will often spend weeks bickering over trivial issues, racking up $10,000s of legal fees, delaying the financing and putting the deal itself at risk.

Enter angel fund Y Combinator, which has just released the financing documents it has standardized and used with dozens of entrepreneurs. If these documents get a reputation for being fair (which is likely given the Y Combinator’s good reputation), they could save million of dollars in legal fees for startups. The key is that both the entrepreneur and the investor trust that the Y docs are a fair deal for all, and trust enough to tell their lawyers not to mark it up! This could do to angel investing what Creative Commons did to copyright or what McDonald’s did to hamburgers.

UPDATE (8/14): Scott Rafer (a past VV guest) posted his convertible debt note (direct link to doc) he’s using for his current company, Lookery. Rafer did a convertible debt deal, which has many advantages as my friends at Venture Hacks have argued. On the other hand, Josh Kopelman has argued against it, pointing out several disadvantages. It seems to be the type of issue that could go either way depending on the dynamics of the particular company, oppertunity and investors — but if we had a standardized set of docs for each verified by a trusted third party it’d be very powerful. The NVCA did this for later stage docs (of course they’re funded by the VCs). Who could do this for convertible debt rounds?

Over the course of the last week, Fred Wilson has been writing about “Venture Fund Economics” at the newly-redesigned AVC. Fred has tackled topics like how venture capitalists are measured, the impact of management fees and carry on net returns, and the impact of big winners on venture returns. What’s more, Fred has done the unthinkable — he has described venture economics in the context of his own fund’s specific economic terms. While he hasn’t posted the economic performance of his fund to date (that is probably more naked than even Fred is willing to get), he has posted the model he and his partner Brad built when assessing the attractiveness of raising a hundred million dollar fund. The model is fascinating and brings to light the challenges venture funds face to achieve index returns, let alone the outsized returns associated with top tier venture firms. (Great stuff, Fred!)

Given the challenges faced by venture investors to drive market returns, one reasonably might ask the question, “why do limited partners continue to flock to the asset class?” Who better to answer that question than a bona fide Limited Partner. Enter Chris Douvos. Chris is the co-head of private equity investing for TIFF (The Investment Fund for Foundations). Before that he was with the Princeton Investment Company. Chris is a wildly smart, experienced investor who I always love chatting with. Give one read of his new blog and you’ll understand why. In the course of discussing the intricacies of the LP business, Chris makes analogies to baseball, the lottery, greek tragedy and uses classic Chris words and phrases like “horseplay,” “impish,” “hotties,” “livin’ la vida loca!” and “Caliente!” Chris’s blog is just plain fun to read. And that is saying a whole lot when you consider that Chris is talking about investing in VC and PE firms — not exactly scintillating material by its nature.

Interestingly, in one of his first posts, like Fred, Chris addresses the challenge of venture economics. Only instead of discussing venture fund economics in the context of a $100M fund, Chris talks about the more daunting $500M fund (Chris prefers the smaller funds — he says he likes being “long idiosyncrasy and short momentum”). According to Chris’s math, a $500M fund needs to create between $12B and $17B in company market capitalization in order to deliver a 3X return (the bar Fred set for himself as well). In Chris’s words:

“Here’s where it gets dicey for the masses, though (and I’ll make some gross simplifying assumptions): if you’re an LP and investing in an run-of-the-mill $500 million fund hoping to get a 3x net return, that fund has to generate $1.75 billion in returns ($1.25B in profit less 20% carry equals two turns of profit). Of course, that’s just the capital that accrues to the firm’s ownership stake. Since a lot of firms end up owning only 10-15% of their companies at exit, you’ve typically got to gross the $1.75 billion up by a factor of between 6.67 and 10. That suggests that those firms need to create between $12 and $17 billion of market cap just to get a 3x fund-level net return to their LPs. Caliente!

Let’s unpack that box a bit more: at the $15 billion midpoint of the exit range above, a firm that invests in 25 early-stage companies will have to get, on average, $600 million exit valuations for each and every one of them. That’s a pretty daunting number when you consider that the typical M&A valuation has hovered in the high double-digit millions for quite some time.”

It is a daunting task for sure. To deliver those returns it almost assuredly requires a huge hit or two in your portfolio. So does that mean VCs need to swing for the fences? I don’t think so. As Fred rightfully points out, “There are hitters in baseball, the best hitters in fact, that hit balls out of the park when they are just trying to make good contact.” (Fred and Chris share a love of the baseball analogy). The power hitters are the guys Chris is trying to back. And those are the guys who will deliver the best returns.

For more great insights into the VC and Private Equity markets, you should definitely check out Chris Douvos’s blog. This is stuff no one has blogged about before, and certainly not in such an entertaining way — another fantastic addition to the blogosphere.

Over the course of the last week, Fred Wilson has been writing about “Venture Fund Economics” at the newly-redesigned AVC. Fred has tackled topics like how venture capitalists are measured, the impact of management fees and carry on net returns, and the impact of big winners on venture returns. What’s more, Fred has done the unthinkable — he has described venture economics in the context of his own fund’s specific economic terms. While he hasn’t posted the economic performance of his fund to date (that is probably more naked than even Fred is willing to get), he has posted the model he and his partner Brad built when assessing the attractiveness of raising a hundred million dollar fund. The model is fascinating and brings to light the challenges venture funds face to achieve index returns, let alone the outsized returns associated with top tier venture firms. (Great stuff, Fred!)

Given the challenges faced by venture investors to drive market returns, one reasonably might ask the question, “why do limited partners continue to flock to the asset class?” Who better to answer that question than a bona fide Limited Partner. Enter Chris Douvos. Chris is the co-head of private equity investing for TIFF (The Investment Fund for Foundations). Before that he was with the Princeton Investment Company. Chris is a wildly smart, experienced investor who I always love chatting with. Give one read of his new blog and you’ll understand why. In the course of discussing the intricacies of the LP business, Chris makes analogies to baseball, the lottery, greek tragedy and uses classic Chris words and phrases like “horseplay,” “impish,” “hotties,” “livin’ la vida loca!” and “Caliente!” Chris’s blog is just plain fun to read. And that is saying a whole lot when you consider that Chris is talking about investing in VC and PE firms — not exactly scintillating material by its nature.

Interestingly, in one of his first posts, like Fred, Chris addresses the challenge of venture economics. Only instead of discussing venture fund economics in the context of a $100M fund, Chris talks about the more daunting $500M fund (Chris prefers the smaller funds — he says he likes being “long idiosyncrasy and short momentum”). According to Chris’s math, a $500M fund needs to create between $12B and $17B in company market capitalization in order to deliver a 3X return (the bar Fred set for himself as well). In Chris’s words:

“Here’s where it gets dicey for the masses, though (and I’ll make some gross simplifying assumptions): if you’re an LP and investing in an run-of-the-mill $500 million fund hoping to get a 3x net return, that fund has to generate $1.75 billion in returns ($1.25B in profit less 20% carry equals two turns of profit). Of course, that’s just the capital that accrues to the firm’s ownership stake. Since a lot of firms end up owning only 10-15% of their companies at exit, you’ve typically got to gross the $1.75 billion up by a factor of between 6.67 and 10. That suggests that those firms need to create between $12 and $17 billion of market cap just to get a 3x fund-level net return to their LPs. Caliente!

Let’s unpack that box a bit more: at the $15 billion midpoint of the exit range above, a firm that invests in 25 early-stage companies will have to get, on average, $600 million exit valuations for each and every one of them. That’s a pretty daunting number when you consider that the typical M&A valuation has hovered in the high double-digit millions for quite some time.”

It is a daunting task for sure. To deliver those returns it almost assuredly requires a huge hit or two in your portfolio. So does that mean VCs need to swing for the fences? I don’t think so. As Fred rightfully points out, “There are hitters in baseball, the best hitters in fact, that hit balls out of the park when they are just trying to make good contact.” (Fred and Chris share a love of the baseball analogy). The power hitters are the guys Chris is trying to back. And those are the guys who will deliver the best returns.

For more great insights into the VC and Private Equity markets, you should definitely check out Chris Douvos’s blog. This is stuff no one has blogged about before, and certainly not in such an entertaining way — another fantastic addition to the blogosphere.