If an initial public offering is the defining rite of passage for a startup, then an IPO road show is the trial by fire. It's a grueling, three-week pilgrimage to plead the company's case before as many as 70 separate gatherings of institutional investors, securities analysts, and portfolio managers. The road show is the toughest -- and most important -- sales call in a private company's history.

Enter Jerry Weissman. The 62-year-old former novelist and TV producer has established a virtual monopoly as road show guru to leading high-tech executives. Weissman, founder and president of Power Presentations Ltd., based in Santa Clara, California, has operated behind the scenes of many of history's most celebrated IPOs -- from computer giant Compaq to software innovators Intuit and Yahoo!

Entrepreneurs and venture capitalists seek his advice for one reason: Jerry Weissman knows how to talk to money. Don Valentine, the legendary venture capitalist, says Weissman's coaching added up to $3 per share to Cisco's price when it went public in 1989. "I wouldn't do an IPO without him," Valentine declares. He's not alone. Since Weissman formed Power Presentations in 1988, his 200 clients have raised $5 billion.

Weissman shared his lessons on how to talk to money with Fast Company.

Nothing beats a good story

An IPO road show is all about selling. And what is selling but good storytelling? I spend two full days working on "story" with my clients. That's different from the standard approach to presentations. Most executives prefer to just rearrange their old slides rather than have an original thought.

The greatest story ever told

There's only one story an IPO audience wants to hear: Why is your company an attractive investment opportunity? Executives typically spend their time making presentations to their partners or customers. But what's desirable for customers will not always benefit investors.

Jay Duncanson, a cofounder of Ascend Communications, is a superb presenter. He was a professional deejay and did all of Ascend's customer presentations. But during preparations for the road show, he kept talking about "Ascend's equipment and what you can do with it." Investors couldn't do anything with it. He had to paint a picture of what the MIS directors of giant companies were doing with it, and how that translated into returns for investors. When it comes to a road show, the only benefit that matters is ROI.

You are the author

No presentation exists independent of the presenter. A presenter has to own the material. In the case of a road show, that means the CEO or CFO must write the presentation.

A few years ago I worked with two companies in the same high-tech sector. The CEO of one of the companies busted his chops preparing his presentation, while the other CEO left it up to his marketing people. The two offerings were priced within a day of each other. The first went out at the top of its range, the second at the bottom. It wasn't a coincidence.

Hype doesn't help

Institutional investors see four to eight new companies every day, five days a week. They've heard everything. Presenters have to respond to that skepticism. Hype doesn't help. The most critical part of a road show presentation is the last 15 minutes, during the Q&A. Investors want to see how people stand up under pressure.

Every CEO on every road show gets asked the same question: "What keeps you up at night?" The best strategy is to admit what your problems are and then tell the audience exactly what you're doing about them.

Tim Koogle, CEO of Yahoo!, did that particularly well. When Yahoo! went out last year, it was competing with four or five other search-engine companies. Koogle responded to his audience's concerns by stressing the importance of brand identity. He talked about creating an image rather than a service. He preemptively answered the question: Why is Yahoo! different?

Attention must be paid

You have 45 minutes to persuade a skeptical audience about a company you've worked several years to create.

That means you need a great opening gambit. Scott Cook of Intuit is good at this. Here's how he started: "Allow me to begin today's presentation with a question: How many of you balance your own checkbooks?" Nearly everyone raised their hands. "And how many of you like doing it?" No hands went up. But he didn't stop there. He said, "There are millions of people all around the world who don't like balancing their checkbooks. Intuit has a product to solve that problem." That's a statement that catches the attention of investors.

Alex Frankel ([email protected]) is a San Francisco-based writer. His articles have appeared in "Wired" and "Red Herring."