I was recently reading some old posts on Venture Blog and couldn't believe how short they were. One might call them pithy. Or one might also call them lazy. Either way, they were short. I should really try that again.

I have been teaching a class at Harvard Law School this winter semester called Venture Capital and the Technology Start-up with John Palfrey, the Executive Director of the Berkman Center. It is really fun to be back at the law school and working with John. I have been blown away by the energy that the law students are bringing to the topic of Entrepreneurship and Venture Capital. Sadly, I never had a VC or Entrepreneurship class in law school. Lets see, I had torts, contracts, criminal law, federal courts, administrative law, property, intellectual property, corporations, securities regulation, constitutional law . . . but no entrepreneurship. Then again, I don't know that I would have had the sense to actually take a VC or Entrepreneurship class back then. So its presence would have been wasted on me.

Today my students had to actually pitch business ideas to real live VCs from the Boston area. And they did a great job. As I was discussing with them how to think about company building and pitching, it struck me that much like the law, building great companies is all about applying precedent. Only, instead of the applicable precedent being case law in this instance, the applicable precedent is a business case. Pitching your business is all about finding the right business analogs and describing how they apply to the company you're building (e.g., "we're the Amazon.com of funeral supplies."). That isn't so different from finding the right case analogs and describing how they apply to the lawsuit you're defending. So there may be hope that we lawyers are able to figure out this entrepreneurship stuff yet.

Driving home from the city yesterday I was listening to a very interesting interview of Madeline Albright on NPR. Albright made a range of insightful observations about diplomacy, world affairs and the Presidency. During the course of the interview, one statement in particular jumped out at me. Albright said that she would rather have a President who was confident than a President who was certain. She noted that a confident President could take principled positions and stand for things that mattered, but would still have the good sense to listen to those around him and take counsel from a range of brilliant advisors. In contrast, a certain President would have no need for advisors because the appropriate course would be "clear" to him.

Madeline Albright's comments reminded me of a talk I heard Paul Graham give at Foo Camp a couple summers ago. Paul was discussing the attributes of successful enterpreneurs, and he argued that the best entrepreneurs were open minded and had good judgment. He contrasted that with failed entrepreneurs who were stubborn and had bad judgment. Paul stated that while having bad judgment could be a handicap for an entrepreneur, if you had both bad judgment and were stubborn, you would necessarily fail. I suppose in Graham's parlance, the President that Madeline Albright is looking for would be confident but open minded.

I am in complete agreement with Madeline Albright and Paul Graham. Startup success requires confidence but not certainty. I have worked with startup CEOs in the past who spent more time at board meetings defending their positions than listening to the board's feedback. Sure, some of the time those CEOs were right and some of the time the Board was wrong. But board meetings shouldn't be about certainty. The should be about confidence. The confidence to hear what other smart people have to say. The confidence to listen. The confidence to stand firm on things you believe are critical to the success of your company. And the confidence to change your position when clearer minds prevail. Like great Presidents, the best CEOs will have the character and the confidence to lead while listening. It isn't easy. But it can mean the difference between success and failure.

I was having breakfast this morning with Salil Deshpande from Bay Partners. Salil and I were talking about assessing company progress and how best to measure that progress. Salil invests in super early-stage deals and has his companies report to him on their progress on a frequent basis. He said that he had one CEO who would report on his progress in such florid language that eventually Salil had to forbid his use of adjectives in his progress reports. Salil said that he didn't want to hear that things were going great. He wanted to hear precisely how things were going.

I nearly jumped out of my seat. Salil had articulated one of my biggest pet peeves when it comes to company pitches (and board meetings for that matter). I hate adjectives. I don't want to hear that one of the company founders is a "fantastic sales exec." I want to hear that she was Presidents Club the last twelve years running. I don't want to hear that the product is "revolutionary and paradigm-shifting." I want to hear about the specific features of the product that are differentiated and how. I don't want to hear that the company has "massive market traction." I want to see a graph of progressive quarterly sales and a giant sales pipeline.

Adjectives are not convincing. Facts are convincing. I may not agree with the conclusions a company draws from those facts. But I will at least be in a position to appropriately assess those conclusions. Whereas adjectives are all about conclusions without the underlying facts. As an entrepreneur, you are far better off having me determine that your market is "massive," your founders are "brilliant," and your product is "elegant," than to tell me that your company has "an elegant solution serving a massive market designed by brilliant founders." So reread your pitch and remove all of the adjectives. It will go massively, monumentally, gargantuanly. colossally better that way.

When I first started writing VentureBlog, I used to talk a lot about entrepreneurship. At the time, not a lot had been written about pitching VCs or the Venture Capital process, so there was lots of virgin territory. Since that time, dozens of VCs have started blogging and much has been said about what it takes to get a VC down the isle. Bits and pieces here and there -- a good Google archeologist can pull it all together. But having spent the week pontificating about PowerPoint and the likes, I've decided to take one more swing through the basics of pitching a VC.

As I thought about the process of pitching a business, it struck me that no matter what the stage, the information was essentially the same. A good elevator pitch contains the same content as a good executive summary contains the same content as a good PowerPoint contains the same content as a good business plan. The distinction among these business descriptions is not the substance, it is the degree to which the essential elements are fleshed out. Each document contains slightly more detail than the preceding.

Elevator Pitch --> Executive Summary --> PowerPoint --> Business Plan

This makes good intuitive sense. There is no reason that the things that are most compelling about your business would change based upon the nature of the business description. Nor would an investor be interested in different things by virtue of the form that description takes.

What, then, are the essential elements that make up a good PowerPoint, a persuasive elevator pitch, a compelling executive summary? I have no doubt that VCs will differ somewhat on the precise list, as well as the order and the emphasis. But at its core, I believe that a successful business description should include the following elements:

1. Introduction
2. Team
3. Product
4. Market
5. Business Model
6. Competition
7. Financials
8. Conclusion

If you are pitching a VC, start with these 8 slides. If you are writing an executive summary, start with these 8 headings.

Obviously some businesses will require additional information that is outside the scope of these basics. I am not suggesting for a second that you should always pigeonhole your business into these categories alone. But they are a great starting point from which to build a persuasive description of your business.

An interesting debate has broken out between Glenn Kelman and Mike Arrington. Glenn is the CEO of Redfin, a Seattle-based startup that is trying to modernize the process of buying and selling homes. Glenn's a smart guy and a great entrepreneur. And he has always struck me as quite thoughtful. Which is why I was surprised to read his recent blog post entitled, "How Green Was My Valley." In that post, Glenn extolls the virtues of Seattle, while attacking Silicon Valley:

"the Valley's monomania is really just a kind of pubescence. What else could account for the Valley's self-righteousness, its congregations of frustrated dudes, its all-nighters, idealism, delusions of grandeur, mood-swings, longings, dramas, hero-worship and pranks? Anywhere else by contrast seems all grown-up."

Wow. Those are strong words. And the rest of his post is equally provocative. Glenn doesn't just praise Seattle. He berates the Bay Area.

When I first read Glenn's post, I almost took the bait. But I thought better of it. Mike Arrington, on the other hand, did not. Mike couldn't have Glenn badmouth the Bay Area as a "heartless amnesiac" without pointing out to Glenn that the Bay Area knows better than to waste its time focusing on the past. Mike couldn't let Glenn get away with praising the Seattle lifestyle without pointing out that it is just that, a lifestyle; the Bay Area has better things to do than worry about lifestyle. Mike couldn't let Glenn get away with baldly suggesting that Bay Area businesses are trendy and Seattle businesses focus on "what works" without giving a single concrete example; the Bay Area is all about specific examples, not baseless accusations. Mike couldn't let Glenn get away with any of it. That's just not something Mike can do.

I don't raise this to join in the rumble against Glenn. I am a fan of Seattle. My partners at August Capital have funded some great companies in Seattle, not the least of which is Microsoft. But I do want to take issue with one of Glenn's criticisms of the Bay Area. Glenn refers in a number of different ways to the obsessiveness of the Bay Area and suggests that the Bay Area's "monomania" is somehow a detriment to company building. I have to disagree. I love the obsessiveness of the Bay Area. It is the drug that fuels the Bay Area's startup economy. And it is the drug that fuels my every day as a tech investor. I love the fact that I can talk about entrepreneurship at AYSO. I love the fact that I can have conference calls with my CEO's at 1am. I love the fact that wildly successful entrepreneurs who could retire for life dive into their next venture within six months of leaving their last. I love the fact that Palo Alto's newest yogurt shop is a hotbed of tech recruiting. I love the fact that I funded a company after bumping into them at a local coffee shop. I love the fact that school auctions include items like "a tour of Facebook" and "10 hours with a trademark attorney" and "company logo design." Is it obsessive? You bet. Is it good for business? You bet.

To tell you the truth, I don't actually think that the obsessiveness of successful startups in the Bay Area is any different from that of successful startups in Seattle. I happen to know that Glenn himself is completely obsessed with entrepreneurship and building Redfin into the next great company. What is unique about the Bay Area is the pervasiveness of that obsession. It is everywhere you go. And I don't think that's a bug. I think it's a feature.

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Here’s a guy who made a site that reviews prostitutes.

Obviously, you can make a LOT of money with pornography and prostitution related sites but I would never go that “low”.

In a little-known success story, TheEroticReview.com has come to dominate the country’s prostitution scene, which is increasingly migrating from the street corner to the Internet.

But now the site’s founder, David Elms, is in jail awaiting trial in Los Angeles in a case unrelated to the site, leaving the fate of his influential underground world uncertain. In dozens of conversations and in postings on the Internet in recent weeks, prostitutes have expressed concern that if The Erotic Review goes offline it could hurt business. But in the same breath, many are rejoicing about the potential downfall of Mr. Elms.

One escort agency that was banned from the site has accused Mr. Elms of antitrust violations, suggesting that he abuses his power over the sex trade. Other critics say he accepts, and sometimes demands, sex or money to promote certain women and agencies.

via nytimes

I was having breakfast this morning with Salil Deshpande from Bay Partners. Salil and I were talking about assessing company progress and how best to measure that progress. Salil invests in super early-stage deals and has his companies report to him on their progress on a frequent basis. He said that he had one CEO who would report on his progress in such florid language that eventually Salil had to forbid his use of adjectives in his progress reports. Salil said that he didn't want to hear that things were going great. He wanted to hear precisely how things were going.

I nearly jumped out of my seat. Salil had articulated one of my biggest pet peeves when it comes to company pitches (and board meetings for that matter). I hate adjectives. I don't want to hear that one of the company founders is a "fantastic sales exec." I want to hear that she was Presidents Club the last twelve years running. I don't want to hear that the product is "revolutionary and paradigm-shifting." I want to hear about the specific features of the product that are differentiated and how. I don't want to hear that the company has "massive market traction." I want to see a graph of progressive quarterly sales and a giant sales pipeline.

Adjectives are not convincing. Facts are convincing. I may not agree with the conclusions a company draws from those facts. But I will at least be in a position to appropriately assess those conclusions. Whereas adjectives are all about conclusions without the underlying facts. As an entrepreneur, you are far better off having me determine that your market is "massive," your founders are "brilliant," and your product is "elegant," than to tell me that your company has "an elegant solution serving a massive market designed by brilliant founders." So reread your pitch and remove all of the adjectives. It will go massively, monumentally, gargantuanly. colossally better that way.