In 2000, Jeffrey Bussgang found himself across the table from John Doerr, the prominent venture capitalist who funded Google and Amazon. Bussgang and his partner were pitching their start-up, Upromise, a loyalty program that lets people earn money for college by shopping at participating stores. When they reached Slide 17 of the PowerPoint presentation, Doerr started grilling them. "What are the revenue drivers that would bring the breakeven point forward another six months?" Doerr asked. "And why do you figure Year Four gross margins at 88 percent?" Bussgang froze. He can't remember what answer he managed to come up with. To his relief, Doerr decided to fund Upromise, which eventually went public.

In 2003, Bussgang went over to the other side. He joined Flybridge Capital Partners, a Boston-based early-stage venture capital firm in which he is now a general partner. After years as an investor, Bussgang wrote a guide for founders looking for venture capital. His book, Mastering the VC Game, due out this month, walks entrepreneurs through the inner workings of VC firms and offers advice on topics such as pitching investors and negotiating term sheets. He recently spoke with Inc. senior editor Bobbie Gossage about how to get funding.

What surprised you about life on the other side?

I didn't really understand VC motivations as well as I thought I did. Until you really understand the venture capitalist business model and how venture capitalists are motivated, their behavior can be mystifying. I didn't really think about venture capitalists as professionals who were trying to build their own careers and operating in the confines of a partnership. There are a lot of constraints that venture capitalists have.

Like what?

For example, in most venture capitalist firms, the entire partnership needs to be supportive of the deal. As an entrepreneur, I would spend all of my time trying to convince the person I was talking to and not realizing that he, in turn, had to convince his whole partnership.

How do you find the right VC firm?

Every partner and every firm has a sweet spot -- a kind of opportunity that this investor loves to invest in. A lot of this information is on the Web. You can see what deals individual partners do as well as what the entire firm does. You can also speak to other entrepreneurs who have worked with that firm and get more information about what that investor finds exciting.

What are some mistakes that entrepreneurs make when they approach VCs?

One is thinking that how they get in front of the VC is not important. In fact, the path to the door says everything about the company and how it will be treated. If a CEO who has made me money in the past recommends someone to me, I always take that meeting. The quality of the introduction is incredibly important. A blind e-mail from someone I don't know is handled with a very different priority.

You actually say that an entrepreneur is better off playing the lottery than cold e-mailing. Why is cold e-mailing so terrible?

Ultimately, in venture capital investing, we're investing in people and in their ability to execute on an idea and create value. Unless I know you, how could I possibly invest in you?

Do you have a shot of getting funding if you didn't go to MIT or Stanford?

The odds are better, obviously, if you have opportunities to interact with VCs either through your academic affiliations or business contacts, or by going to certain conferences and events. But there are plenty of people who didn't go to Ivy League schools who find a way to get to know venture capitalists and other entrepreneurs and get in the mix.

Laura Fitton, for example, is the founder of oneforty, an app store for Twitter. She didn't go to an Ivy League school. She's never run a company before. But she became a guru in the Twitterverse and got to know a lot of investors -- including myself -- through her thought leadership. By the time she started her company, she had a lot of great investors who were interested in her. We funded her company last year.

What makes for a good pitch?

Being prepared and showing a great command of the business. When I pitched John Doerr, I wasn't prepared. He was pushing me on the business model, and I didn't have good answers.

What questions should you expect?

Why do you have an unfair advantage in this situation? Why are you uniquely positioned to succeed? Why couldn't three people from Bangalore who have the same idea outexecute you? And how are you going to make me money? Entrepreneurs need to be comfortable with the back and forth. The more probing the VC is, the more interested he probably is in what you're doing.

Are entrepreneurs too optimistic when they pitch?

Yes; the line every entrepreneur uses is, "These projections are conservative." Entrepreneurs are optimistic animals, but we're looking for paranoid optimists. People who are always worried about what could go wrong.

Sometimes the interests of the investor and entrepreneur aren't in alignment. What can be done to fix that?

You can mitigate that by having clean, simple deal terms. If you have a lot of complexity or bells and whistles in the deal, the interests are less likely to be aligned -- things like multiple liquidation preferences. That means if I invest $5 million, I get three times my money back -- or $15 million -- before you get anything. These sorts of onerous terms get entrepreneurs and investors out of alignment.

How can founders maintain a critical role in the company as it grows?

Get an executive coach and surround yourself with mature executives and mentors. That's what Bill Gates and Mark Zuckerberg did. It takes a rare individual who can be a great leader, whether it's a 10-person company or a 10,000-person company. Another approach is to look for a different role in the company, like CTO or head of development. Many founders make that transition very successfully.