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What Would Square’s Jack Dorsey Do?

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New Relic CEO Lew Cirne asked himself a question upon embarking on developing a new startup inside the company he co-founded. He wondered: “How would Jack Dorsey do it?” Dorsey started Twitter and then Square. He is now Twitter’s chairman and runs Square, too. He innovates arguably more than any CEO in the startup world. And he had a system Cirne could use.

Today, Dorsey’s system serves as a foundation for Cirne to take one-week blocks in secluded retreats just to code. His goal for New Relic: go beyond just being a one-trick company. Build a company that lasts well beyond the lifetime of its core service: application lifecycle management.

How Cirne Follows Dorsey’s Ways

“He is good at managing his time while building big companies,” Cirne said about Dorsey in an interview at the Glue conference last week. The interview followed a keynote on how Cirne has found new ways to be a developer while also serving as CEO. “He is good at managing his time while building big companies,” Cirne said about Dorsey. “He has built big partnerships. He puts a theme to each day of the week. Thursdays and Fridays are for innovation.”

For Cirne at New Relic, Monday is for strategic review. On Tuesday, the whole day is for tactical product review. On Wednesday, Cirne does press interviews, folllows up with calls and generally catches up. On Thursday and Friday he codes. “I have been doing that for a year,” Cirne said. “Chris joined a year and a half ago.”

chris_cookThe “Chris” Cirne refers to is Chris Cook, president and chief operating officer of the company who joined New Relic in 2011.

In 2009, Cirne ran a 40-person company. The company was growing fast but Cirne had no time to code. He realized he had to build out the team earlier than he thought.

“There was no way I could jump into coding and succeed on an operating level,” Cirne said.

He filled out the team, with Cook being the most important hire, joining New Relic in 2011. Cook had worked for Cirne at Wily Technology before the ALM company that Cirne co-founded sold to CA in 2006. At CA, Cook ran a 1,000-person organization within the company.

Now with the space and time left open by operations out of his hands, Cirne can code during the week and take breaks to get away to do development. He spent his first week-long coding marathon starting January 1 in Lake Tahoe at his family’s cabin. He did another week in March at the family cabin. A few weeks ago, he invited a few other developers to spend a week in a cabin on Mount Hood. He’ll go to Santa Barbara in the next few weeks for his next retreat. But why is he so motivated? New Relic has had fantastic growth with 50,000 customers, 350 employees and $115 million in financing. An IPO is expected.

The truth is, Cirne is haunted by his past. New Relic represents a second chance to build a great company, re-invent it and build it again, That’s something he did not do at Wily. Sure, Wily had a successful exit, but it did not become something beyond what it had started as in its earliest days.

For Cirne, Dorsey’s methods have provided a model for him to develop a new foundation for the company. What that is, Cirne won’t say, but it’s fair to guess that any company that manages 115 billion metrics has something to build on.

Cirne is taking a risk. Eventually, the new service will need operations support, which will take attention from New Relic’s core products. And what Cirne builds may be a total flop. Still, those are the tradeoffs even Jack Dorsey has to deal with every day.