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Startup Lessons From The Ink-Stained Trenches

Startup founders and news reporters have more in common than being stereotypically broke.

Before the music and airplanes and space ships, billionaire tycoon Richard Branson’s first business was a magazine, of which Branson was editor-in-chief.

Before launching the now $2.5 billion fashion company, Banana Republic’s founder was a journalist. Mel Ziegler was a reporter for the San Francisco Chronicle, where his wife and cofounder was an illustrator.

Where the skills of business and journalism overlap, entrepreneurship is often found.

Columbia Journalism School, founded by Joseph Pulitzer in 1912, lists 40 startups launched by its students in the last five years, including AllThingsD, (a news-focused progenitor to Kickstarter), and Vayable. City University of New York has an entire program dedicated to journalism entrepreneurship, and has inspired other schools to create similar curriculums.

"Journalists hone... reporting muscles that are hugely helpful for entrepreneurship," says Jeremy Caplan, Director of Education at CUNY’s Center for Entrepreneurial Journalism. "They develop sharp observation skills that are crucial when you're wearing the startup hat and identifying potential problems to solve."

I’ve made surprising use of my journalism training in running my own startup, Contently. Before becoming a journalist, my ideas tended to suffer premature deaths by false assumptions and lack of shoe leather. Tromping around Harlem searching for murder witnesses and calling up celebrities to ask for quotes taught skills that transfered directly to building a business.

Here are cues every entrepreneur should take from journalists:

Ask good questions.

Journalists learn the art of asking succinct questions, of letting others do the rambling.

A good reporter doesn't ask leading questions. She doesn't ask yes or no questions, unless she literally wants a one-word answer. She doesn't ask a question and awkwardly present an array of possible answers because she doesn't know how to stop.

Yet businesspeople do this all the time.

Good questioning skills are essential to gaining value from business mentors, gathering actionable feedback from customers, resolving concerns among potential clients, and choosing good employees and investors. In the early days of a company, every decision is critical. The right information will mean the difference between another day in business or not.

"Asking probing questions is vital for anyone who wants to succeed with a startup, because you have to get the information you need even when others are reluctant to give it to you," Caplan says. "Sharp questions also help you get past the point where others have failed, by drawing out issues hidden beneath the surface."

Tell a good story.

Winning over clients, investors, and the public all boils down to storytelling.

Journalists can craft a compelling story with a beginning, middle, and end. They can portray drama. They learn to put the most important facts up front to grab attention and make sure people leave with salient information if they check out early.

A mantra in the journalism world is "show, don't tell." This often means telling a story through experts’ or witnesses’ quotes. In business, letting customers tell the story of a business problem and solution adds immense credibility.

New York-based education startup Coursekit was founded by pre-drinking-age UPenn dropouts Joe Cohen, Dan Getelman, and Jim Grandpre. They raised $6 million after their product had been live for only a few months.

The reason: Cohen knows how to tell a big story. When pitching, he didn't say, "We're building education software." He said, "We're building the Facebook of education." His investor deck pounded billion-dollar opportunity after another.

Coursekit let customers do the talking. One slide showed angry tweets by users of Coursekit's main competitor, Blackboard, saying "Blackboard sucks" and "Fuck Blackboard." The next slide juxtaposed positive Twitter feedback for Coursekit.


When a reporter files a story with a magazine editor, an army of interns gets to work. Interviewees are contacted to verify statements; sources are double- and triple-checked. No single writer should be able to jeopardize the integrity of a publication. No misconstrued fact should get away with being printed.

In the same way, good entrepreneurs are honest with the data they see in front of them. They don’t invent business cases (in the same way reporters don’t invent stories). If they do, their companies fail. Enron, Jayson Blair—the bottom drops out for all of them.

Too many startups fail because founders refused to see the facts in front of them, or didn’t fact-check the assumptions their businesses are based on. Though it’s difficult, reporters are used to killing stories that don’t pan out as expected. Entrepreneurs who can objectively do the same with their ideas will waste fewer resources.

"Journalists grow accustomed to slaving away in the shadows on reporting projects that may or may not pan out, so they're well prepared for the ups and downs of the entrepreneurial process," Caplan says.

Deftly deal with difficult people.

Sarah Lacy, a columnist at BusinessWeek and TechCrunch who founded the news startup PandoDaily, says "learning to get along with strong personalities" is a skill she brought from journalism to business. "A lot of the challenges as an entrepreneur are essentially people challenges," she says.

Writers constantly deal with rejection: sources who won’t talk, editors who reject pitches, publishing houses that throw book manuscripts in the slush pile.

Good entrepreneurs steel themselves against inevitable rejection from customers, partners, investors, and just about everything else. The ability to take rejection in stride and persevere is a shared trait between both trades.

Cut things in half.

Journalism school teaches reporters to self-edit. "Cut your story in half," a professor of mine used to say.

The Lean Startup movement teaches this for business. The idea of a "minimum viable product" is to build the most lightweight version of an idea possible, then test it. Tearing ideas down to their fundamentals, forgoing bells and whistles, is key to great writing and startup success.

"Journalists...have a lot of practice boiling down jargon, detecting BS, and cutting through extraneous detail," Caplan says. "Those are handy talents to have when you're pitching ideas and negotiating partnerships."

The staples of innovation and entrepreneurship—as well as good journalism—are scrappiness and hunger. Both entrepreneurship and journalism are about working hard, fearlessly pursuing ideas and taking risks.

"Being a journalist is incredibly individualistic and autonomous," Lacy says. "You bring your box of tools and have to fight your way out of each day mostly alone. Same as being an entrepreneur."

[Image: Flickr user Dustin Diaz]

Add New Comment


  • J. Anthony Gell

    Thanks Shane - great article, also I love the "Cut your story in half" point. I'm going to use that myself and share that with my storytelling family! ... My 70+ year old aunt who has a great imagination and storytelling style has always said; "never let the facts get in the way of a good story"... however with a general disregard of facts, I now see why she's a great storyteller but never went into journalism!!

  • Tunguska

    Typically what I missed, an excellent synthesis of what former techies should keep in mind in their daily work. Thanks!

  • Dr Tayaba Khan

    It makes perfect sense. Journalism and writing are the first mediums that a creative (entrepreneural?) mind select. This helps the person realize his creative net worth. With that determined, and the necessary contacts made, the journalist can then create the model he wants, and sell the product he makes. Very good piece

  • digidave

    Hi All.  Thank you for the kind words. All lean startups know the taste of blood/sweat/tears combined into a gross mixture you have to drink every morning and that's definitely something I learned via Spot.Us. This article is great Shane. And I can tell you are speaking from experience as well. While we haven't had too much time to chat - I remember when I visited Columbia and you were still a student. Now that I've been teaching for a bit I can definitely say that as a teacher you can see when certain students stand out among others. And without a doubt - you stand out among your peers. Please remember to hire me one day later in life ;) 

  • Edward Domain

    Shane Snow: Great article- I know the creator of Spot.Us and watched him grow it from next to nothing. You do your readers a disservice by using Sarah Lacy as an example.  Her brand Pando is regularly lampooned by VCs on the West Coast and Dan Lyons of Newsweek refers to a large chunk of SIlicon Valley "tech news" as the 'Silicon Valley Cesspool."  

    Lacy is a joke- as a journalist talking about wearing out the shoe leather, you should look a little further afield then defaulting to Lacy just because she worked at TechCrunch- your last paragraph talks about "cutting things in half" and being lean- Sarah Lacy raised $2.5M in VC money- the same VCs who admit (in private) the only reason she got money was because they knew they were buying positive reviews of their portfolio companies- and then she complains on her site she doesn't have much to pay writers. Hardly following the lean philosophy.  

    David Cohn, founder of Spot.Us is a perfect example of the lean startup.  He won a small grant from the Knight Foundation and all the stories put out by Spot.Us was crowdfunded- truly lean.  He asked the people what they wanted, and the people responded with their dollars.  

  • Arabella Santiago

     Good article except for the Sarah Lacy mention. She's not a fact-checking journalist. She's a pig-headed blogger who doesn't know how to run her company with the same startup principles she attempts to cover. For example, she turned off the comments to the post on Mike Arrington leaving the board at Pando Daily (non-transparant) and she doesn't listen to her users (vital to creating and developing a startup).