What journalists learn when they become entrepreneurs

Jessica Lessin, The Information
In an era of free content, the former Wall Street Journal reporter made a big bet in starting a subscription-only site covering tech news in December costing $399 a year. She said that some of her journalism skills carried over into running a business, like figuring out what questions to ask and getting the answers. What she wasn’t prepared for was the decision-making that would follow and the need to prioritize.

“In business-building land, you have to make a lot of decisions,” she said. “One of the things I had to learn quickly was which decisions take a lot of time and which don’t. Early on, I felt every decision was make-or-break.”

Lessin credited her audience with helping in a couple of ways. As tech industry folks, they’re welcoming of entrepreneurs. Since the site doesn’t take advertising (at least not yet), they also are her main source of feedback, in the form of email, comments and readership numbers.

She has not released subscription numbers yet but said, “We’re delighted” by the growth so far, adding that The Information is getting interest in companies wanting corporate accounts (currently, all subscribers are individuals). “It’s very early days, but we know deeply that the model works.”

Ryan Singel, Contextly
Singel didn’t fit the mold of the clueless journalist when he and data scientist Ben Autrey struck out in 2012 and started Contextly, a content-recommendation service for publishers.

While a reporter and editor for Wired, which had an entrepreneurial spirit to start with, he sought to streamline the site’s process for adding related-story links to the bottom of articles. Before that, while looking for writing jobs, he’d worked briefly in startup land making search tools for companies. After 10 years in Silicon Valley, he said, “It doesn’t look that hard from the outside.”

It turned out harder than it looked. Singel wasn’t prepared for all the sales-side tasks involved in a startup, like fundraising, sales calls, marketing and accounting — “business-y stuff I never really contemplated I would need to learn.” Like other new entrepreneurs, he learned to figure out which client wishes to grant without getting bogged down. “Be careful saying yes,” he advised.

Contextly has raised some angel investing and claims more than 600 clients, including PBS, Modern Farmer and Make magazine, but is in the “ramen profitable stage,” Singel said.

“Fundraising is hard,” he said. “We’ve been bootstrapping.” Here again, sales training would have come in handy. As a former reporter, cold sales calls didn’t phase him, Singel said. “The odd moment became, the one thing I tend not to do is, at the end of a call, ask for money.”

Nicholas White, The Daily Dot
White was a reporter and editor at his family’s Sandusky Newspaper Group before starting The Daily Dot in 2011 to cover online communities. That didn’t prepare him for the naysayer investors who questioned the site’s purpose as “trivial bullshit” and the need for a sizeable reporting staff.

“The investment community is really optimized for technology,” he said. “They want five engineers in a garage, bottling lightning.”

White stuck to his guns, though, and said an early decision for The Daily Dot turned out to be critical: It started out by reporting just on reddit before expanding to cover Internet communities more broadly, echoing what others said about the need for a narrow focus. “Looking back, we could have been even narrower, like politics on reddit. The biggest thing we’re going to fight for is adoption. Then you can saturate it. This is why Facebook is Facebook. Within three weeks, they saturated Harvard. They now have everyone in the world.” If he could turn back the clock, he also would have moved faster in replacing people who didn’t contribute to the culture he was trying to build.

“In any company, you’re trying to create a specific culture,” he said. “You’re not going to be all things to all people. If anything, my biggest mistake is not recognizing quickly enough where there has not been a good fit.”