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Dick Costolo launched his first companies in Chicago, where just like every new founder he had to do the long hard slog of raising money. Almost two decades later came the roadshow to take Twitter public. Speaking at tonight’s PandoMonthly in San Francisco, Costolo told Sarah Lacy there’s not much of a difference between the two. Selling is selling, whether you’re trying to get twenty bucks out of some guy’s pocket or billions from mutual fund investors.

“You never stop selling. And you don’t get to the point where you get to say, ‘Hey I recorded the video last month, watch that,’” Costolo said. “You’ve got to do the same hard enthusiastic selling meeting after meeting after meeting.”

He also shared the two big lessons he’s learned over the years that apply to meetings with the little guys all the way up to IPO roadshows.

First and foremost, he explained, the biggest lesson was not to get defensive when investors probed or challenged him on particular questions.

“When they start hearing you get defensive of course then they start asking themselves rightly, ‘Why is he so defensive, maybe I should probe on this more?’” Costolo remembers. He said he had to learn not to think of the questions as a challenge to his authority. He came to understand that investors wanted to learn whether, as the company leader, he was thoughtful about the architecture. They probed to understand whether his team had designed the product to be extensible instead of just a point solution.

The second big piece of advice Costolo had for entrepreneurs is that they have to keep up enthusiasm during pitch meetings. It doesn’t matter if they’ve answered the same damn question nine times, sighing and showing that is the investment death knell.

“These sound like common sense things but you see people answer them like it’s the ninth time they’ve answered it,” Costolo says.

“What do you do to stay enthusiastic?” Lacy asks. “Coffee, jumping jacks, speed, any tricks?”

“Mostly just coffee but it doesn’t work after awhile,” Costolo says.

To prepare for the IPO, Twitter had to undergo a road show where Costolo pitched investors all day long. He says it was a grueling, horrible experience. “The first couple days I kept saying, ‘Hey you guys you’re scheduling these meetings wrong. There’s only four minutes between the meetings,’” Costolo says. “And they’d say no that’s how these things work.”

In LA, on the second to last day of the road show, Costolo got challenged. One guy sitting in a corner had been quiet the whole time. At the end of the meeting he took off his glasses and stared at Costolo, before asking ‘You’re a really good pitch person. You present well.’ Then came the kicker: ‘Why isn’t this going to work?’

Costolo admits it was a great question. His answer: Twitter’s continued success or failure will come down to execution. “Failing to make bold choices,” Costolo concludes. “That’s how you fail. You start to only focus on incrementalism instead of making bold choices.”

[Photo by Yelena Sophia for Pandodaily]