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Last Updated on
April 19, 2023

The Entrepreneurial Journalism Framework with Jeremy Caplan

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What does publishing need to survive and thrive? More innovators and entrepreneurial journalism. That's according to Jeremy Caplan, and he knows what he's talking about.Jeremy is the Director of Education at the Tow-Knight Center for Entrepreneurial Journalism at the Newmark Graduate School of Journalism at CUNY.He shared some great insights with us on the Digital Media Growth Podcast.We're going to lay it all out in this article step-by-step. You're going to learn exactly what entrepreneurial journalism is and the potential it could hold for your own business and the industry as a whole.

Who is Jeremy - and how did he discover his passion for entrepreneurial journalism?

While working as a reporter covering business and tech at Time Magazine, Jeremy was inspired by seeing the industry changing rapidly before his eyes.

Jeremy speaking at the World Publishing Expo
“The field has been changing dramatically over the past two decades. I saw some radical shifts taking place and during my tenure at Time Magazine I decided I wanted to dive deeper into business which I saw as a driving area for change in the years ahead. So I went back to school where I earned a journalism degree as well as an MBA. I loved the learning environment of the University and teaching. I began teaching at that point”

Jeremy had a passion for both teaching and thinking about the future and where journalism and media were heading.Entrepreneurial journalism is relatively new as both a concept and an academic discipline, so it was both exciting and challenging to pioneer the field.

“It was definitely exciting and challenging. There were no textbooks to draw on and there was no history of a field. We were essentially making it up as we went along"

Every field needs its trailblazers.

"That was tremendously exhilarating to work on. We started by thinking about the key changes that were taking place from the business, product and technology sides. We thought about what we can provide to journalists and other professionals in the media to help them build new things. We’ve made significant changes to the program as the industry changes rapidly. New elements were emerging as important like audio, video, shifting platforms, and newsletters as a distribution channel”

Technology and business models change so rapidly in this space that creating curriculum around the topic represents a moving target.

Changing Media Landscapes

Some changes have been disheartening.

"The number of full time US newspaper employees between 08-17 dropped from 71,000 to 39,000 - that’s a 45% drop. That’s a result of major shifts in the ways newspapers function and the challenges they face from a revenue perspective. 36% of US papers had layoffs from Jan 17 to Apr 18 and we’ve seen a few thousand more in the last few months. We expect to see more still as a result of the Gannett merger. The challenges facing newspapers is in line with what we thought might happen - but nobody knew the extent or speed at which it would happen. It’s really been dramatic"

Others have uncovered new opportunities.

"One thing that’s been surprising - the extent to which new forms of distribution have become a core part of the journalism ecosystem. The Washington Post and the New York Times have more than 50 newsletters that reach people daily and act as big drivers of subscription. Many other publications, even traditional publishers like New Yorker magazine have run some successful newsletters”

Audio in particular is a growing at a startling rate.

“44% of the US population - about 124m people - have listened to a podcast. Revenue from podcasts has also grown by 86% each year at over 300m now. We didn’t anticipate the dramatic growth of these channels. That's exciting. Even as these layoffs are happening in the newspaper arena, we’re seeing tremendous investment in other arenas like social video, podcasting and newsletters. Some of that is coming from big media organizations and some is coming from really niche, independent publishers”

Do we need more entrepreneurial journalists and innovative media companies?

“We need more innovation all round. We need to rapidly adapt and innovate. It’s hard because you need to place bets that aren’t always clear. The New York Times is placing a lot of good bets. You can see that with their video products and their partnerships with Netflix and Amazon. The Weekly which grew out of their Daily podcast - the most successful podcast on the iTunes store with over 10m in revenue. They do a huge amount of experimentation”

Some of their bets haven’t been so successful, like their VR initiative.They distributed VR headsets to hundreds of thousands of readers. There was a huge number of downloads for the app initially, but people grew tired of the novelty or lost interest. That hasn’t really been a long-term success, especially from a revenue perspective.That’s the nature of this though - you place different bets and try new things.The New York Times have also created initiatives around gaming and cooking which have both been very successful at driving subscriptions.“That’s the kind of innovation we need across the news industry”We're starting to really see it too.Wall Street Journal is also hiring 15 new product people, and the Washington Post has shifted to become a much more innovative company in recent years. A lot of the most innovative publishers are digitally-native brands like Quartz. Entrepreneurial journalism is tougher for the smallest publishers, yet that's where it's needed the most.

“What’s needed is for that innovation to spread across into the lower tiers. Those organizations don’t have the same kind of bandwidth. If you’re a small local niche site it’s tougher to do the same kind of experimentation. But on the positive side we have great support organizations like the institute for non-profit news, INN, LION, and others which help niche and smaller publishers”

The Entrepreneurial Journalism Framework

Jeremy breaks down the Entrepreneurial Journalism process into three big buckets:

  • Product
  • Community
  • Sustainability


“Product is about thinking user-first and focusing on the fact that we’re here to serve users - whoever they might be. It could be a niche community, a geographical community, a psychographic community, people with a particular hobby, professional interest or condition. It could also be demographic - people of a certain age, ethnicity or gender"

All innovation starts with the user.

"Thinking about that user group and really understanding their needs, it’s user-first design thinking approach. What kind of products and services would be valuable to those people? If you create valuable things you’ll attract people to your products and generate value back for your organization”

The product part is all about effectively identifying an under-served pool of potential users, developing a deep understanding of their needs - then being creative about how to address those needs.It could be through a podcast, newsletter, SMS service or news site. Applying the right mindsets and research methods will point you in the right direction.


The second part is about engagement and building a community around your product or service.

“It’s all about engaging with users, following up with them, talking with them. You can build communities through social platforms, email, events in the real world where users can connect with each other. In this era where we’re all spending so much time in front of our devices - people are hungry for opportunities to connect with other humans. Media brands that bring people together have found great success, revenue and growth by bringing people together”

A good example of this is the Texas Tribune.They held over 50 events last year and brought people together for all kinds of purposes - they held a lot of panels, a big ideas festival and more.Through these events, they generated a lot of interesting content ideas and journalistic inspiration.But for their audience it’s an opportunity to learn, network, and feel part of a human brand. They also directly support the brand through paying for events in some cases, while in other cases the events are supported by sponsors.


The third important part of the framework is sustainability.A key part of this is doing things lean, which luckily is easier than ever with modern tools.

“We’re fortunate in this era in that we can start things really easily and validate ideas with free tools. Whether it’s starting a test publication on medium, creating a simple podcast using anchor, distributing to community databases. We can use Facebook in some cases, Email tools like MailChimp to create a free newsletter - all these platforms allow us to validate an idea at a really low cost in a lean way. We can efficiently find out if there really are people who find value in what we’re doing”

This all helps to keep the costs under control during initial testing and experimentation.

Sustainable Revenue

The other side of the sustainability coin is revenue.

“What we’ve seen is that people are willing to pay. We’ve seen significant growth in subscription programs with organizations like The New York Times, the Washington Post and The Wall Street Journal”

It’s not just the big established publishing brands who’ve seen success though.

“We’ve also seen usership growth for The Skimm, and many other niche organizations. People are in many cases willing to pay if it’s something useful, indispensable, or addresses a real passion that they have. Cooks illustrated is another good example around a passion where people are willing to pay out of personal interest. Cooks illustrated doesn’t have ads”

It’s all about finding a product that gives a group enough value that they are willing to either pay directly, or pay significant attention to.

“If enough attention is paid by an audience, there are a lot of opportunities to create partnerships and sponsorships that can generate revenue”

So there it is - product, community, sustainability.

“It’s a challenge to find the right mix. The technology is an additional factor. But increasingly we focus on the simplicity of the product and the technology isn’t necessary as the driving factor - it’s really about understanding the users and thinking about products that are useful for real people. Start small with little experiments”

That’s something that even the smallest publishers can do.

Understanding your Audience

Once you’ve identified an underserved audience and started to think about what products or services could be a good fit - it’s all about building deep understanding and empathy.This kind of insight is absolutely key for successful entrepreneurial journalism!“The essence is understanding people’s lives”Jobs to be done can be a useful framework in this context.

“What do they need to get done? If you’re moving to a new city you might be looking for a publication or news resource. You might need help finding a home, a job, or a social community to be a part of”

People also have pains and gains.

“They’re seeking gains. They want to find comradeship and friendship, they want to excel in their careers, they want comfort and joy in their personal lives. On the pain side they want to avoid certain frustrating things. They want help navigating the complexities of the city that they live, or their professional sphere”

Whatever the goals, dreams, and frustrations that feature in their lives - there are ways that quality innovative media products can help them.

“It really starts with trying to identify - through interviews, secondary research and getting to know people in the community - what their daily lives are like”

You also need to understand the context you’re operating in.

“Typically you’re not the only provider. People are often using existing solutions. They already have resources to look at job opportunities, how their healthcare works, local schools and social opportunities”

They are likely already using something, but are they completely happy with it?

“In many cases there are limitations. It’s not on the right platform, they want to listen to it, get it by text or email and they cant. Maybe it’s not in their language - they want it in Spanish or another language. Perhaps it’s not available at the frequency they want, or not packaged in a way that’s engaging to them - it could be boring or poorly designed. There are often limitations to the existing offers”

This is where an entrepreneurial media organization or innovative news start-up can come in.

“We see this need, we identify this need through talking to people and observations. So we’re going to test it. What if we offer a newsletter, or create a landing page with resources. Might that be useful to people? Then test it and build on it to refine the offer. That’s how the process often looks”

Revenue and Monetization options

Direct audience revenue is a great option for some publishers.

“I think organizations that have deep loyalty and are dominant in their sphere have the capacity to directly ask their readers to pay. These are publishers who have a strong need behind them, like Bloomberg or the Wall Street Journal. Skift is an example of a very successful B2B travel site. For them they can show the importance of what they provide professionally and personally - so asking for audience to pay comes naturally”

It’s not this clear for everyone though.

“In other spheres we’ll continue to see innovation and experimentation around third party support. The classic way is obviously through advertising and sponsorship. We’ll see new kinds of sponsorship, increasing experiments implementing ads in newsletters, podcasts and events”

There are other options too to create a sustainable revenue mix.Other third parties - like non-profits, universities and foundations - will increasingly see the value in journalism and quality content production, and understand the shared goals at play.

“If you’re an environmental organization you might decide to increasingly support climate journalism as well as scientific research - because journalism is a major lever for impact”

Investors typically aren’t hugely interested in small journalism products because they aren’t associated with large exits.The civic value, though, that these products and services can bring is significant.Entrepreneurial journalists shouldn’t necessarily be trying to start huge cash cows, but rather be thinking in terms of bringing immense value to an underserved audience.

“I think a lot of other players - NGOs, Universities, local Government - will increasingly see an opportunity to fill the gap and fund some of these services that provide value. Much as researchers and artists rely on this kind of funding, I think we’ll increasingly see this with journalism”

While some might wish for a purely market driven news media, Jeremy doesn’t think that’s the only approach.

“Maybe in an ideal world, but I don’t think that’s the world we’re living in right now. The evidence is the decline of working journalists, resulting in cutbacks in coverage on important issues - like state, local and complex issue coverage”

Many non-profits like Propublica and Voice of San Diego are doing great work in investigative and accountability journalism. They’re not disappearing, but they’ve had to get creative about their funding models.[caption id="attachment_7296" align="aligncenter" width="1706"]

Propublica cover areas that might not be the biggest subscription drivers - but their mission is a vital one[/caption]Quality media can support the vibrancy and vitality of a local community, open the public’s eyes on crucial issues, and it’s essential for a healthy democracy at a local and national level.As this becomes more clear and the plight of local news more widely appreciated, we can be cautiously optimistic about increasing support.

Engagement at its best: Email Newsletters for Entrepreneurial Journalism

Jeremy teaches his students to use email to its full power.

“The great thing about email - everyone uses it everyday. It’s a great way to reach people. When people are reading an email - they’re focused on it in that moment. On a website there might be lots of different stories, tabs open etc - but email allows for clear focus, delivery and distribution”

Many publishers have developed awesome newsletter products.

“Those who are doing it most effectively are taking advantage of what the medium is and what it isn’t. Quartz has always been a leader in email. Something they realized early on is that people don’t always want to be taken through to a website when they’re reading a newsletter, they often want a self-contained product”

Quartz emphasized this from the start.They focused on self-contained newsletters that were easy to read and mobile friendly - more than 50% are read on mobile.[caption id="attachment_7295" align="aligncenter" width="1651"]

Quartz have really nailed their newsletter products[/caption]

“Don’t presume that people are going to open a bunch of links. Allow people to simply scan. Axios is another great example of this - their newsletters are very scannable and broken up into chunks that make them nice and readable. Yet if you want to dig deeper you can”

Another interesting approach is to involve community in newsletters.Jeremy mentioned a former student of his Matt Kiser, who runs WTF just happened today, a newsletter about the Trump era.

“He brings the community in and engages them in various ways like through GitHub. There are people who help with copyediting, suggesting ideas and new products. Someone also volunteered to create a podcast version. There’s no advertising so people chip in money”

Matt was able to quit his other job and focus on the newsletter full time.

“He’s an example of an entrepreneurial journalist who isn’t breaking the bank or making millions, but he’s able to support himself running a great product that serves a lot of people with daily news. He made it sustainable. I think this is a good model, we don’t need to always be building big businesses. We need to build businesses and products that support a small team and add quality to the ecosystem”

Private Messaging: an emerging opportunity for Entrepreneurial Journalism

Private messaging apps are becoming the next big thing for news consumption.

“Messaging is immediate, it’s direct, it has a personal feel to it, it’s two-way. NYT used a modified version of this during the Olympics so people could tell them what they wanted to hear and let people ask questions directly to the reporter”

They used their own messaging platform but it could have been Whatsapp Viber, or Wechat.

“They fit in with the way people organize their information and engage with news. So I think they’ll continue to grow”

Niche and time-boxed communities: a key opportunity for entrepreneurial journalism?

“I think one of the big opportunities will be to develop niche communities around different topics and time-boxed communities. For example - when the Davos summit is happening - Quartz has a specific newsletter around this period”

Messaging apps have a lot of potential here too.

“I can imagine other organizations having messaging groups set up for particular events like the Olympics, World Cup, big science conventions or educational conferences - whatever the topic may be. This could be a good tool to engage with users, readers, listeners and viewers. They can give their input and reactions, and you can build a community”

This can have great benefits down the line.

“The more engaged people are, the more likely they are to become paid subscribers. They’re more likely to become champions of the brand and spread the word”

It’s really important for brands to do all they can to engage the most enthusiastic readers and build buzz around their content, and this is a great avenue to look into.

The future of private messaging

Will these platforms evolve to facilitate large groups on the same scale as social and web communities?

“Whatsapp remains limited in group size. It’ll be interesting to see how the constraints, restrictions and rules evolve for these platforms. Are they open to new uses by news organizations, or are they going to be focused on core user needs which are not necessarily the same?”

Key future trends for Entrepreneurial Journalism

Jeremy thinks publishers and would-be entrepreneurial journalists need to keep a keen eye on the rising prominence of micro-niches.

“Many people are no longer solely devoted to cooking in general, for example. Increasingly, people are excited about very specific topics within the realm of cooking. They might be passionate about cakes, or science readers might be very focused on a specific branch of climate coverage. Or in the sports realm, people are increasingly focused on La Liga, Bundesliga or whatever particular league they follow. It could be Handball or anything”

This looks like an accelerating trend in diverse areas of coverage.

“Addressing micro-niches as opposed to covering broader topics is a trend that we’ll see more of. Covering a very specific election, covering it through and through - with a newsletter, podcast or website. You could be narrowly focused on one particular seat in congress, or one particular sports team. I think nicro-niches are a trend we’ll see continued focus on”

The audio sphere too is ripe for experimentation.

“Podcasting has already reached its peak arguably. People from all corners have been jumping into the fray. But I think there are still many interesting experiments ahead”

This could be in terms of the time of day:“We’re seeing some afternoon news summary podcasts”And also format:“I think we’ll see interesting new approaches. Shorter formats for example, a lot of people really like short quick podcasts - just as they like short bites of information in a messaging or newsletter platform"Podcast audiences are primarily young - and highly engaged. Think about ways you could tweak your format to give your listeners what they want.[caption id="attachment_7292" align="aligncenter" width="1023"]

The 2019 Reuters Digital News Report gives a interesting look into the rise of audio[/caption]We're going to also see more collaboration between big publishers and major distribution platforms.

"We’ll see more collaboration with the big video platforms. We’ve seen New York Times partnerships with Netflix and Amazon on series like Diagnosis and Modern Love

Jeremy thinks we’ll see others following in their footsteps and growth in these partnerships.

“The LA Times has been working with local TV stations, other publishers are partnering with Apple and Apple News+. Apple’s new paid video product that will arrive this November - we’ll likely see some interesting experimentation from big media brands. Buzzfeed and Fox have partnered with Netflix, and we’ll see more of these brands trying to find distribution with these partnerships”

These partnerships will stretch into other fields as well.

“iHeartRadio has been working with various media brands too. We’ll see a lot of interesting new partnerships that span across media organisations”

Not everyone can collaborate with Netflix, Apple or Amazon obviously. But there are surely opportunities to partner with someone. Partnerships with influencers, local brands, or other publishers in your niche are all potential avenues - it's up to you to find ones that fit with your goals.[caption id="attachment_7294" align="aligncenter" width="640"]

Diagnosis is a major collaboration between Netflix and the The New York Times[/caption]

Jeremy’s Recommended Resources for Learning more about Entrepreneurial Journalism (and much more)

You can learn more about Jeremy at or check him out on Twitter.“”I’d love to recommend people to come by the Newmark J School if you’re in New York City, we have events all the time”Jeremy is also developing a website at the moment called,“It’s just in its beginning, experimental stages. It will provide resources for people looking ahead to the future of entrepreneurial journalism”Jeremy also recommended several books:

Jeremy also put together an incredible Google Doc full of resources for entrepreneurial journalists that you should definitely check out if you want to delve deeper.It was a pleasure to speak with Jeremy, he’s a highly knowledgeable and inspirational figure. He ended the interview on an optimistic note, which fits well also to wrap up this article.I hope you learned something valuable to take on your own entrepreneurial journey.

“This is an amazing moment for journalism and media. It’s a difficult moment given all the layoffs and challenges, but it’s also an amazingly exciting period. There’s so much innovation happening, so many products and services, so many new entrepreneurs breaking through and bringing their products to people. I’m really excited to learn more and talk about this topic”

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