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Journalist entrepreneurs: These are the three skills you need to start developing now

A little preparation can go a long way toward de-risking your business model


“It’s at those moments of sharp sudden change, when the system is being shocked and shaken in various ways, that we might have the greatest opportunity to change things.” — Thomas Homer-Dixon, Author of The Upside of Down.

Back in 2004, a few close colleagues and I decided to test a novel(ish) theory and the lessons have stuck with me to this day. Specifically, I’ve found those lessons regularly infusing my thinking over the years, and they seem particularly relevant for the unusual world we live in today.

The theory was, in a nutshell, that it was possible to develop “viral content” predictably, and that it was not as random as people believed. To put that theory in its proper context, here are just a few of the things that didn’t exist in 2004:

  • iPhones (released in 2007)
  • Facebook (not open to the public until 2006)
  • Twitter (not founded until 2006)
  • Reddit (launched in 2005)
  • Upworthy (founded in 2012)
  • … and BuzzFeed (founded in 2006)

However, it was BuzzFeed’s founder, Jonah Peretti, and his culture-jamming contemporaries that brought this theory to life with early work like the Nike Sweatshop Emails (2001). And that brand of fresh thinking combined with a nascent Internet became the foundation of a whole movement around how to seed viral content online (for better and for worse).

Studying and applying the underlying theory behind Peretti’s work eventually resulted in my colleagues and I launching a successful viral project called Marry An American (if you were in the U.S., it was called Marry A Canadian). The project was so successful at the time that it brought my 2004-powered web server to its knees because thousands of people were signing up and it was appearing on news sites around the world including NYTimes, CNN, NPR, The Nation, as well as the CBC, BBC, and many others.

Screenshot of Marry An American, as well as a story about the effort on CNN.

But what stuck with me from that experience has nothing to do with viral content.

What stuck with me was this: through the experience of trying to make predictable, repeatable viral content we had developed three powerful new skills — can you guess what they were?

Go ahead guess, I’ll wait…

You’ve got the reporting down, now what?

I suspect you’ve heard the term “10,000 hours” mentioned before? It’s the idea that 10,000 hours is a rough estimate of the time investment required of a person to become truly excellent at something.

I believe that holds true for many skills, like learning a musical instrument, or becoming proficient at software programming, or reporting epic stories for that matter.

However, if you’re a journalist wanting to practice entrepreneurship, what skills should you start investing time into? The choices may not be as obvious.

Part of the answer is embedded in the lessons that I learned back in 2004. And, if I take these lessons and look at them through the filter of everything I’ve learned since — working in an online newsrooms, researching entrepreneurship at Stanford, and coaching news startups — these stand out to me as some of the most important skills to learn:

  • The first skill is coming up with concepts (or spotting opportunities)
  • The second is testing those concepts (ideally, with real people)
  • The third is being ready when the time is right: recognizing the right moment to launch — knowing what “early warning signs” to look for — and feeling confident that you’re prepared enough

I’ll dig into each of these and then explain why they’re effective, of course, but after that I’d also like to share why I believe they’re particularly relevant today, while the news industry — and the world — is in a state of shock.

Let’s dig into the skills first:

Coming up with new concepts. It’s a muscle. You must exercise it regularly. It’s like your daily or weekly editorial meeting where you get good at pitching story ideas and assessing other’s pitches. You need to do the same with creative ideas.

Have you ever noticed how some entrepreneurs — news, tech, or otherwise — seem to be able to hit it outta’ the park repeatedly? I don’t believe this is luck; I believe it’s a well-developed practice of this first skill — because coming up with good ideas is a muscle.

Sometimes this skill is actually being good at spotting opportunities. With practice, people can develop a “sense” of what’s happening in the world around them that’s insightful toward coming up with new concepts. Noticing a pattern of people struggling with the same problem would be one example of that skill. Again, this is a muscle that can be developed with practice.

For example, in the case of, my colleagues and I met regularly to pitch each other on concepts. It took months to arrive at a strong concept, but the pitches got better every time we met. And the idea for a fake online dating site came from an observation that in 2004 the thought of meeting people on the Internet was still very fringe (and a bit cringe-worthy).

Testing concepts (experimenting): Concepts that you can test are called experiments. And experiments are a specific thing.

Concepts don’t live in a vacuum. To come alive, they must breathe and interact with the world around them. To give concepts life, you must birth them in some small way and show them to a subset of the world through experiments.

There is risk and tension here. Like a plant, they might wither and die. But better for them to pass quickly than to be put on life support.

For a concept to become an experiment, you must set a pass/fail criteria and a timeline. You must show them to people. You must evaluate the results and make a decision to persevere with the concept, pivot it in some small way, or fail it and reset.

For example, when testing the viral content concepts, I would make a point to ask strangers about different concepts we were considering at parties. I would ask random people about them at coffee shops. I made asking people about these potentially-meme-worthy ideas a habit. And, over time, I was able to quickly assess how much potential certain concepts had given an aggregate of people’s responses.

The third skill, and in some circumstances the most critical skill, is timing and preparedness. The moment in which a new product is launched can make or break its chance of success.

Sometimes there’s not much choice in the matter, but more often than not you have a choice about when to launch your new, now tested, concept into the world.

And, to do that, you must consider when would be the best “right moments” to do so.

It’s like being a surfer just waiting for that right wave. There are lots of waves. Many will get you up on the board. Some halfway to the shore. But only a few will result in the most memorable ride of your life.

Seeing the early signs of the most epic waves takes practice.

In the case of Marry A Canadian, we believed that leading up to the 2004 U.S. election was the right time to launch. There was an epic battle between Bush and Gore heating up. Many liberal Americans were fearing a second term with Bush and considering their options. October was a good guess at the right timing for launching the project. However, as accurate as that guess was, we actually missed the mark. The real moment the project took off was the day after the election when people woke up and realized that Bush had won. That was a learning moment for us: we had seen the small wave, not the big wave — that’s why it takes practice.

Use your natural skepticism on yourself

If you have a theory or concept that you intend to act on, you must develop a regular practice around testing it. It’s really that simple.

Journalism entrepreneurship is no different. If you have an idea for a local news startup, you likely have a theory about why it’s needed. Perhaps the theory is that:

  • The existing news options aren’t giving residents what they need?
  • Or perhaps it’s that you could produce better information than what’s currently available and that residents would respond to that?
  • Or perhaps it’s that a specific audience isn’t being served adequately?
  • Or that people will pay for news?

The thing is: When it comes to hearing theories from other people, journalists are natural skeptics. But when it comes to their own ideas, the skepticism recedes far too quickly! As is often quoted “If your mother says she loves you, check it out,” and that should go twice as much for when the source is you.

Entrepreneurship is by definition a risky proposition. You’re effectively doing something new that there are few if any templates for. If what you were doing was less risky, it would be called a franchise, not a news startup. And one of the reasons it’s risky is because you’re going to bring your own unique take to the idea, and attempt to deliver it in your own unique corner of the world — and those factors introduce unpredictability, as do many other factors.

That’s why I believe that learning how to de-risk your news startup business model is so important. And once you’ve learned the basic skills that will help to de-risk your business model — coming up with concepts, testing those concepts, and being prepared for the right moment — you must work to develop a practice around those skills so they become a reflex.

Now is the time to develop your practice.

Take the time today to be prepared for tomorrow

Circling back to the quote that opened this essay:

“It’s at those moments of sharp sudden change, when the system is being shocked and shaken in various ways, that we might have the greatest opportunity to change things”

Thomas Homer-Dixon went on to say: “We need to develop the attitude of expecting surprise. Welcoming it into our lives.”

We are living through a profoundly unique moment in the history of humanity. Our civil society is being dramatically reinvented in front of our eyes. And it’s likely that many aspects of our lives that we’ve taken for granted for these last decades might be tested over the next weeks, months, and years.

However, as Homer-Dixon explains in The Upside of Down, it’s often in those moments of shock that there’s an opportunity for change.

Looking at the swift and dramatic action that many corporate news organizations took in the first weeks of March, I suspect that the corporate overlords had their plans for a “publicly-palatable downsizing” at-the-ready — just waiting for the right excuse to implement them.

But the key message to take away here is that you can be prepared too.

Here’s an example:

On January 29, 2016, the Guelph Mercury News shut down leaving 150,000 residents without a daily local news source. The newspaper had been around in one form or another since 1854, and had a circulation of roughly 13,000 (with 9000 paying subscribers). This closure was a shock to many and was reported widely in Canadian media:

Tony Saxon never saw it coming. Nor did his co-workers. They knew circulation had fallen to 9,000 from 22,000, but they believed their leaner operation was working. He heard about the closing by telephone message from a colleague at another paper. — Globe & Mail article

Then, on February 8, 2016 — just a week later — a small digital news upstart called Village Media launched and hired two former Guelph Mercury News reporters.

Village Media had been preparing for that day, even if unknowingly, by testing their concept and refining their business model in smaller markets. So, when news came of the Guelph paper’s closing, they had a plan, and a playbook, ready to go — and they were able to take advantage of the moment.

Being ready and acting fast helped them to garner press attention and virtual cheers from Guelph residents — both of which contributed to the quick growth of’s readership.

The Hero’s Journey

You can be ready for a moment like that too. Like the real-life hero in the movie who’s quietly and diligently honing their skills every day for years, just waiting for an opportunity to right the scales of justice. (Okay, maybe not quite like that, but you get the idea!)

Here’s a more concrete example: When I was at Stanford, many of the people in the fellowship — including me — picked up the book Designing Your Life. It’s a classic text written by two Stanford professors that describes a system they developed, based on the practice of Design Thinking, to help anyone become more adept at:

  • Coming up with different visions for your professional life
  • Testing each of those those visions out in some meaningful way
  • Moving toward the chosen vision when the time is right

And it does this by encouraging a set of simple exercises that anyone can do, at any point in their life or career.

The exercises build on, and roughly follow, the d.School’s Design Thinking Process:

At the risk of repeating myself to death, the takeaway here is: to be ready to take advantage of opportunity — you need to practice. You need to have developed several concepts — guesses at what you might do, and what might work — and you need to have tested those concepts in advance, so that you’ve got more than just a gut-level hunch guiding you.

Start small and build a habit

I’m not going to say “Stop watching Tiger King, give up Netflix, and establish a monk-like devotion to developing these skills,” because that would just be crazy! However, I am going to go so far as to suggest that if you make the time to establish these habits now they will pay off in the near future.

For example, here are some perfect analogies in the other parts of our lives:

  • If you want to get more physically fit, as long as you establish a regular habit of [insert your chosen exercise here], you’ll eventually get there. You’ll probably start slow — perhaps once a week — and eventually work your way up to more.
  • If you want to develop a meditation practice, it all starts with establishing a habit of a daily meditation — most people start at just a few minutes and grow from there.
  • And if you want to develop a writing practice, you have to put in the time to develop a strong habit there too. For example, I try to write for at least 30 minutes a day, and that’s the single factor that helped me the most toward my goal of publishing 12 essays in 2019.

Frankly, if you’re a reporter of any kind, you’ve already developed and established several professional habits (hopefully!) including:

  • Sniffing out a potential story
  • Checking public records or public sources of data
  • Interviewing sources
  • Fact checking your source’s statements
  • And so on…

Think back to how you enshrined those habits. You most likely cemented them deep within your body’s cellular memory by doing them again and again and again and again. Repetition is the mother of success.

And the same is true for the skills you’ll need to develop as you shift toward thinking more entrepreneurially about your journalism. They must be practiced now, so you will be as ready as you can be when the time is right.


P.S. If you’re ready to start developing skills like the ones outlined in this essay, be sure to subscribe for notifications about the next journalism entrepreneurship boot camp. With some luck, there will be an announcement very soon. Stay tuned!

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Phillip Smith

👉 My passion is helping: 💰 Newsrooms make more money; 📈 News startups grow their audience; 🔥 Journalists succeed as entrepreneurs. Let’s talk 📩