Jeremy Caplan


How startup sites can take advantage of emerging revenue streams

As journalism entities move beyond ads in pursuit of new revenue streams, events have proven a popular target. People who won’t pay $15 for a digital subscription, the theory goes, may pay $20 instead for wine, cheese and a panel of journalists.

Staging events isn’t a simple endeavor for small organizations structured around news. But for many up-and-coming media organizations like GeekWire, an independent tech news site and online community in Seattle, events are an important part of increasingly diverse streams of revenue.

Rebecca Lovell

During a live chat this week, we’ll discuss events and other emerging revenue streams with Rebecca Lovell, Geekwire’s chief business officer.

Lovell, who oversees the site’s advertising, events, sponsorship and other business initiatives, answered chat participants’ questions and shared thoughts on a variety of topics, including:

  • What separates successful events from those that flop
  • Lessons learned about new revenue streams
  • How to overcome challenges that growing news startups face

You can replay the chat below.

Interested in learning more about generating revenue for startups? Consider applying for Poynter’s Revenue Camp for Entrepreneurial Journalists.

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3 ways entrepreneurial journalists can successfully pitch their projects

Ever tried telling your life’s story in a minute? Melting years down into seconds is tough. Summing up a long-simmering passion project can be equally hard.

Whether you’re pitching a new journalism project to a friend or to a financier, you often have to pack your message into a few fleeting moments. To persuade people to invest, collaborate, or even just try out a site requires a special kind of compact communication.

Journalists have ample opportunity to present new ideas. Some 2012 journalism conferences, like the Unity 2012 Convention, feature sessions expressly for startups. Beyond online competitions, like the Knight News Challenge, journopreneurs are increasingly finding alternative outlets for presentations ranging from library talks to Hacks/Hackers Demo Nights.

Whereas slides were once expected, a backlash against traditional PowerPoint presentations among journalists and funders alike has opened the door to more inventive approaches. Here are tips on three approaches for anyone preparing to pitch a project.

Illustrate the impact of your project with evergreen multimedia

Video is a powerful pitch tool. When investigative journalism project Matter raised more than $140,000 in March on Kickstarter, its primary tool was a great video about the need for better science coverage. Similarly, Honolulu’s Civil Beat has used a sleek video to convey the value and impact of its news site.

Honolulu's Civil Beat Introduction Video

The mini-vid has become a new persuasive craft form. Most of the best such videos, like great presentations, answer the following key questions: What’s the problem you’re solving and why is it important? How does the proposed solution work and what’s distinct about it? Who’s leading this and how can others get involved?

Creative pitch videos can take on myriad forms, from animated explainers of the sort popularized by Common Craft and GoAnimate, to simple Webcam recordings and fancy micro-documentaries. Excellent pitch videos are often more informative than slick. One example is this video by Blank on Blank, which publishes otherwise-lost interviews. Here’s another from Colorado’s I-News Network, which received a Poynter entrepreneurial journalism prize in 2010.

Those that are less successful, like this one for MyNetworkOne, often try to stuff too much in, or misfire at humor. When you’re prepping your own video, start by picking a few pitch videos that inspire you. Make a list of their key attributes. To get you started, here is a sampling of 20+ demo videos I gathered into a channel on Vimeo as well as a separate playlist on YouTube. Both include non-journalism projects to illustrate a range of styles.

Make the most of spontaneous pitch opportunities

Sometimes visuals are impractical. When you bump into someone at a conference, you often have to pitch quickly with words alone. No slides. No videos. In these personal pitch situations, it’s crucial to have persuasive snippets ready to go. Here are four components to help get your idea across quickly and effectively.

  • The first ingredient is a brief value proposition that sums up your projecThe Value Propositiont in one to two sentences. “For parents with school-age children, K12Update is a subscription news and photo service that provides a daily stream of photos and news shared by their children’s classroom teachers.” Trim unnecessary details. Don’t get into mechanics until asked. Just clarify the basic value — what it’s useful for.
  • The second key ingredient is a brief founding story or other anecdote that illustrates both the need for the service and its utility. “At the PTA meetings, parents kept saying they wished they saw more of what their kids did in school, like the art projects they were producing. Now they say they feel more connected to what’s going on in the classroom.”
  • The third step is where it’s easy to stumble. Don’t spend time on further details until you stop and listen for clarifying questions. If there’s an empty pause, probe for questions. “What’s your first impression?” or “Does that make sense?” or “How does that relate to your own experience?” Those kinds of questions let the person you’re pitching to signal what s/he is most interested in. That, in turn, increases the chances you’ll find a point of mutual interest.
  • The last part of the personal pitch process is the follow-up. Given that we’re exposed to hundreds of ads each day, we grow accustomed to blocking out messages or quickly forgetting them. That’s why advertisers insist on ensuring recall by running the same ads seven times. When it comes to personal pitches, follow-up with a brief email. Keep it to five sentences or fewer. Refer to something specific you discussed and remind the recipient of your idea, its name and its value. Include a relevant URL and a single phone number and email address. (Don’t give people multiple contact numbers and addresses because that burdens them with figuring out which one to use.) Close with a specific question if you have one (i.e. Would you be interested in serving as a pilot tester?) to simplify their response.

Stretch beyond PowerPoint

When you’re in front of an audience, demoing your product or service is often the best way to illustrate how it works. Getting an audience member up front to participate — or just having all those present try it out live — can be engaging. Number-crunching spreadsheets don’t always have to make an appearance, though mastering key facts and figures around your business helps bolster your credibility.

For elements that are difficult to demo live, check out tools like Projeqt, Jux, Hype and Prezi, which can help you create a free, immersive presentation. Or try other resources I’ve gathered into this stack of new storytelling tools.

If you must use slides, leave behind default PowerPoint templates by working with more design-friendly slide tools like Apple’s Keynote or Web-based tools like SlideRocket. Google Presentations, part of the Google Docs suite, offers a new range of clean designs after a recent upgrade. Include a single prominent image or a few key words per slide.

Guy Kawasaki suggests a 10-20-30 rule: 10 slides, 20 minutes, 30-point font. When you see slides like this one, this one, or these, you’re reminded that visuals can be confusing, distracting, or superfluous. Keeping each slide simple means the audience can focus on you and your message.

In live settings, refer to a Twitter hashtag to spread the responses beyond the live audience. Alternatively, use a tool like or to set up a private backchannel that those present can use to ask live questions or comment on your presentation. That ensures people don’t have to sit on their hands or wait passively for you to finish talking to engage with you. To further draw out those present, try using or to offer up live polls or trivia questions, or to probe for live feedback.

After public demos, gather the most noteworthy comments, Tweets and images into a Storify summary, like this one, to further distribute the impact of your presentation and to serve as a digital scrapbook. Keep a private list of takeaways from each presentation you make. Note that a particular joke got no laughs, or that your first example generated lots of nods of agreement.

Try to keep a record of every question you’re asked after pitching. Questions provide a valuable window into what people are most interested in, and can highlight elements of your pitch that might be unclear.

The late, great cellist Mstislav Rostropovich said that he kept careful track of each performance early in his career so he could consistently improve his stage presentation. Whatever pitch you’re giving, chances are it’s not your last. Keeping a presentation journal can help you consistently refine your message.

Jeremy Caplan, director of education at CUNY’s Tow-Knight Center for Entrepreneurial Journalism, will be teaching in Poynter’s Revenue Camp for Entrepreneurial Journalists. You can apply for the camp here.
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Tips for journalists preparing to launch a startup site

When you’re getting a journalism startup off the ground, you face a number of decision points. Who do you partner with? How do you bring in revenue? How do you get the word out about your project? We’ll discuss these and other key questions facing entrepreneurial journalists in a live chat with paidContent founder Rafat Ali, who is now working on his new startup, Skift.

In a live chat, Ali answered questions on specific decisions, including:

  • Fundraising strategies
  • Whether to provide original content on your site, vs. curating and aggregating
  • Hiring staff

You can replay the chat below for tips and insights.

Interested in learning more about generating revenue for startups? Consider applying for Poynter’s Revenue Camp for Entrepreneurial Journalists.

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Practical tips, resources for entrepreneurial journalists with legal questions

Entrepreneurs leading new journalism ventures confront numerous legal questions. How and when should I determine the appropriate legal structure for my business? What contracts should I use with partners, employees and investors? What legal issues should I be prepared for and, as a journopreneur, who can I turn to for low-cost or pro bono guidance?

I’m not a lawyer, and this post isn’t intended to offer specific legal advice or replace the professional insight of a lawyer. The resources below are offered simply as a starting point for anyone launching a project who anticipates having to grapple with legal questions as the project develops.

Seeking pro bono help

One of the best places to begin, if you’re starting up a media-related project, is the Online Media Legal Network at Harvard’s Berkman Center. The center describes itself as “a network of law firms, law school clinics, in-house counsel, and individual lawyers throughout the United States willing to provide pro bono (free) and reduced fee legal assistance to qualifying online journalism ventures and other digital media creators.”

Not every journalism or media startup will qualify for OMLN’s free legal assistance, but you can quickly assess your eligibility with this FAQ. OMLN considers a number of factors, including your available resources. If paying legal fees would significantly deplete your organization’s resources, you could still be eligible for pro bono help if you’re a for-profit with under $75,000 in annual gross revenue or a nonprofit with an annual budget of $250,000 or less. (More details here.)

Law for journopreneurs 101

If you’re looking for information first, rather than professional legal guidance, the Citizen Media Law Project, also sponsored by the Berkman Center, has outstanding resources. The online legal guide has clear, well-written sections on everything from forming a business to dealing with online legal risks and securing your intellectual property.

The section on choosing a business form for your new organization is particularly helpful if you’re not clear on the relative benefits of, say, a sole proprietorship versus an LLC or some other legal structure. Download the Citizen Media Law Project’s one-page overview summarizing the characteristics, tax implications and various pros and cons for legal structures journalism entities might consider.

To keep up with new resources, tools and information, follow this Quora discussion about legal resources for startup companies.

Free contracts and templates

If you’re more focused on contracts than on sorting out your legal structure, check out Paperlex — a new startup that helps you manage common contracts. Though the full service is still in beta, offers free freelancer contracts, talent releases and non-disclosure agreements.

Founder and CEO Alison Anthoine says she plans to add additional contracts for photographers, videographers, designers and developers. She describes Paperlex as a Web-based contract management platform for news organizations.

“My goal is to empower small businesses and entrepreneurial journalists not to have to rely on lawyers to do all of their legal work,” Anthoine said by phone. “There will always be things you need lawyers for, but a routine agreement isn’t something you should have to call your lawyer about.” is an alternative platform aiming to take the pain out of managing contracts.

The incubator YCombinator has an excellent startup library of documents and tip sheets. For those considering early-stage Angel funding, YCombinator also provides free equity financing documents, so you know what you’re signing away when you bring in investors.

The term sheets were developed in partnership with Wilson Sonsini Goodrich & Rosati, a firm specializing in startup law, among other things. The firm teaches a live legal issues course at General Assembly, a New York coworking and education hub, and has a term sheet generator that will assemble a venture financing term sheet based on questions you answer online.

Additional resources:

  • provides a range of other free legal documents, including consulting contracts. If you want to make sure a name you’re considering is not already in wide use, try, which searches existing trademarks and domains.

  • If you’re wondering about the kinds of contracts you’ll face if you seek out venture capital funding, check out the National Venture Capital Association’s free model legal agreements. The site also includes a good overview of venture capital, as well as stats and research.
  • Chris Cameron’s ReadWriteWeb collection of useful legal resources for startups includes some relevant blogs, articles and tip sheets.

Join Jeremy Caplan, Mark Briggs, Bill Mitchell and Wendy Wallace for Poynter’s Revenue Camp for Journalism Entrepreneurs, May 18-19. You can join by webcast or in person for the workshop in St. Petersburg, Fla., with additional coaching available. Read more


Cheap & useful tools that can help entrepreneurial journalists be more efficient

When it comes to tools, entrepreneurial journalists have the advantage of being free. Free of the obligation to use a news organization’s clunky software packages. Free from layers of tech bureaucracy. And free from having to get approval to try new tools. That freedom, of course, comes at a price. No longer is someone else footing the bill for your digital toolkit. That makes a different kind of free all the more attractive. Free tools.

Fortunately, software developers have turned the world of tools upside down in recent years. Gone are the days when you had to fork out several hundred dollars — or more — for a suite of communication/productivity/office software. If you’re running a small, straightforward project, you can get by with easy-to-use software tools that are free or just a few bucks a month, and most work seamlessly across platforms and devices.

Here’s a quick guide to some of the most useful, easy-to-use tools for any journalist developing a project without a big budget or a lot of time to invest in learning new tech.

Tools for storing & organizing information

Once we’ve wrestled down mounting piles of email, most of us start our day with ideas, notes and lots of random stuff to take care of. That’s why the most crucial information tools are those that let you store information, organize it and act on it. The most flexible, powerful resource I’ve come across for all that is Evernote.

Here are some examples of how journalism startups can use it:

  • In addition to organizing Web research, reporting notes, source info and other raw material, Evernote helps for recording ideas in audio, picture and text form. It also lets you arrange major projects or clients in discrete notebooks. You can share those notebooks with your team so everyone can add notes and access information whenever they need it, from any device.
  • Every account comes with an email ingest address, which means you can just CC Evernote on important contracts or other emails that you’d like to organize in a project notebook. I regularly CC Evernote on contracts I sign and send by email, and documents I know I’ll refer to later (travel details, receipts, etc.).
  • Gathering quick snapshots with Evernote’s mobile apps enables you to remember people, places, notes scrawled on scraps of paper and other loose tidbits that might otherwise fall through the cracks. You can access Evernote from any Web browser or through free software and mobile apps.

Here’s an example of an Evernote notebook with about 50 recent Web clippings I’ve made of tips for startups.

Google tools for creating content

Microsoft Office was once a must-have for any journalist, but Google Docs has basically made it obsolete.

For free, Google Docs provides far more functionality. Not only does the Web-based Google suite include excellent Word processing and spreadsheet tools, but the recently upgraded presentation service, Google Presentations, now rivals PowerPoint, though with fewer bells and whistles.

Here’s my overview of Google Docs, and here are a few Google Presentations that will help you see how they look when posted online:

The most under-appreciated tool in the Google Docs suite is Google Forms, which has allowed startup organizations of all sizes, including ProPublica, to create free embedded surveys that process results automatically into a spreadsheet for analysis, charting and publishing. (Here’s a free template I created as an example of a simple, free Google form for keeping track of invoices. You can freely duplicate it and adapt it for your purposes). Here’s how startups are using the Google Docs suite:

  • To collaborate internally on content-in-progress from disparate locations without worrying about e-mailing attachments back and forth.
  • To publish Web-based documents, spreadsheets and presentations to share through social media or to embed on sites/blogs. Instant easy publishing means new means to reach and impact readers, advertisers and potential investors or donors.
  • To distribute surveys to gather reporting information and client feedback.

Tools for handling invoices

You can create simple invoices with a word processor, but if you want to track your payments more professionally, you may want to try something different.

InvoiceBubble is a free and simple-to-use option I’ve tested and recommend. It’s a simple Web-based service that lets you create and send invoices and track client payments.

FreshBooks is a more fully-featured service that’s much more expensive ($20/month), but if you invoice a small number of clients, you can use the free version with much of the same functionality.

Tools for distributing files

Sending stuff across the Web has long been a nuisance. You can’t email files larger than 25mb, most of us can’t afford to spring for a private server, and it’s not always clear which sites are reliable for distributing your important files.

A few services have succeeded recently at streamlining the process of sharing big chunks of content, such as photo, audio and video files, and large design files. lets you upload material to a private storage page that you can then share access to through a short link.

WeTransfer is another useful service. It doesn’t require you to log in, and you can send any number of files that total up to 2gb to up to 20 email addresses at a time.

If you prefer a solution that is anchored to your computer, Cloud App (Mac only) puts a little cloud icon on your menu bar.

Any file you drag onto the icon is then uploaded automatically and the short-link to that file is posted directly to your clipboard.

And if you’re not yet using Dropbox, it’s become one of the most popular free file-sharing tools in addition to serving as a great way to back up your files.

Tools for backing up your work

When it comes time to protecting your work, a large local hard drive can provide a serviceable initial backup. Alternatively, Mozy, BackBlaze and Carbonite, among others, will back up all the stuff on a given computer to the cloud.

It’s also worth thinking carefully about how best to backup your Web-based social and blog content. Backupify will back up your WordPress files, your Tweets and even your Google Apps.

Here’s a list of some more of my favorite tools. What free or low-cost tools do you rely on for your projects? Share your favorites in the comments section.

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4 ways to start researching the market for your new journalism venture

Journalists love to dive in. Once we’ve got a topic in mind, we rush off to report, write/record, edit and publish. When launching a new venture, though, whether a local or niche site, an app, a network or something else entirely, it’s useful to add a fifth step early on: market research.

In addition to surfacing opportunities you may not have thought about, market research helps clarify the characteristics and interests of your community. It also arms you with business information that’s useful when you’re pitching your product or service to advertisers, sponsors, investors or potential partners.

Before ponying up for subscription services, spend some time with the free resources I’ve outlined below. They’ll help you get a preliminary handle on your intended market.

Size up your audience

Start by gathering basic qualitative and quantitative information about your community and your competitors. Get a quick overview of the businesses in your target ZIP codes. Find out what other sites your intended audience is already visiting, what they’re searching for and where they are. Get a rough picture of how those already out there are faring. There are some free tools that will give you a quick snapshot of the products and services already out there.

Start with Google Ad Planner, even if you’re not focused on ad research. Though developed for advertisers assessing audiences, Ad Planner is handy for quick market assessments for anyone launching a product or service. For example, if you’re contemplating starting a regional business news site for Hartford and New Haven, Conn., you could use Ad Planner to home in on that subject matter and location and then find out what sites are already popular.

If you used Google Ad Planner to look up information about a New Haven/Hartford business-interested audience, here’s what you’d find.

Ad Planner also provides a snapshot of audience characteristics for existing sites, including age, gender, education and income breakdowns. This is useful for getting a ballpark picture of your potential audience. Ad Planner relies on a gigantic mass of Google data to develop its estimates, which are approximations. Check Google’s fine print to learn more about how the data are gathered, and the limitations. Bottom line: the service provides a useful starting point as you’re learning about your audience.

Google AdWords is another tool that’s worth a quick spin as you’re performing a real-world check on your idea. You can run some of your key topic words and ideas through the tool, which helps provide a quick snapshot of what people are searching for. It can hint at what topics readers may consider to be closely related to the topics you have in mind.

If you’re planning on supporting your site with ads, Google AdWords can also give you a quick initial take on the degree to which advertisers value your subject matter as determined by the market price for related keywords.

To round out your starting information, use a free resource like Melissa Data to get local maps, a list of the number of various businesses in a given ZIP code, and any other information that will help refine your understanding of your community. For an exhaustive list of other online market research resources, visit ZenithOptimedia’s Marketer’s Directory, pointed out to me by my CUNY Journalism School colleague, Barbara Gray, a star research librarian.

Find out more about competitor sites

If you’re aware of existing competitors in a particular market, spend a few minutes running through their stats on Quarkbase, Alexa, Quantcast and Compete. Quarkbase provides basic background information on a site, as well as recent tweets about it. It also lists some of the pages within a site that are popular on social networks and that are blogged about. It will even tell you some of the tools that your potential partners or competitors are using.

Alexa gives you some useful information about a site’s audience trends over time, its most popular sub pages, and what people have searched for to end up on that site. Quantcast tells you what other sites a visitor to an existing site frequents, what percentage of visitors are “addicts” versus “passers-by,” and the demographic makeup of the site’s audience.

None of these services can guarantee the accuracy of their information, so think of them as a good starting point for your research, not an end point.

Conduct surveys to gain insight into your community

After gathering community and competitor information, you can gather some real-world insights about your community with qualitative surveys. It’s easy to craft, deliver and collate such surveys using Google Forms.

Create questions that help you understand the relevant media consumption, preferences and behavior of those in your intended audience. Google Forms (part of the free Google Docs suite of Microsoft Office-like Web applications) lets you include multiple-choice, checkbox and scale questions, as well as open-ended questions that give your respondents a chance to express their ideas, questions and suggestions.

As with most survey services, you can then email your survey, post it through social media or embed it on a site or blog. Responses automatically populate a spreadsheet that you can use not only to find and graph patterns of preference or behavior but also to collect and assess more open-ended qualitative suggestions.

Polldaddy, SurveyMonkey, Zoomerang and Poll Everywhere are good alternative survey tools. Poll Everywhere has a distinctively useful feature — respondents can respond to poll questions by texting. That’s handy if you’re reaching out to an audience that thrives on texting, or if you’re surveying an audience in a live session or event. For those with more money than time, services such as AYTM and Lab 42 will conduct quick market research for you.

Get answers to questions about your market

An increasingly useful stop in the initial phase of market research is You can pose an open-ended question about your market, audience or idea and let experts voluntarily reply with thoughts, facts, stats, suggestions or data.

Beyond its value as an outlet for seeking guidance, though, Quora is an increasingly useful living reference for market examples. (Here’s a new Quora board I created with questions and answers for entrepreneurial journalists.) Some Quora questions take awhile to generate responses, while others do not get answered at all. For quick searches of the broadening database of existing questions and answers, though, Quora can be quite handy.

The reason I’ve become such a fan of Quora, which I recently wrote about for the Daily, is that its community rating system has ensured that you can quickly search, retrieve and act on information you find on the site. That’s because the thousands of answers to all sorts of questions are filtered well enough that you can quickly find highly-ranked answers written by people with relevant expertise.

To simplify what can seem like an arduous task, start an afternoon of initial research with these simple Web tools. Depending on how much you already know about your community, you may end up spending additional hours, days or weeks digging into market and audience data. A little market research is useful even if you take the popular “lean startup” approach — launching a project and refining it as you go, rather than waiting until it’s a finished product.

At the very least, spend whatever time it takes to get a qualitative and quantitative initial overview of your community. Doing so will lay the groundwork for both strong community coverage and a solid business case for your project.

What market research resources have you found helpful? Share your thoughts in the comments section. Read more


4 lessons for hyperlocal media from inaugural Street Fight Summit

Deals don’t mean dollars. That was a point of consensus at the inaugural Street Fight Summit in New York City Oct. 25 and 26. Over two days, the summit’s 60 presenters and panelists analyzed their adventures in the trenches of hyperlocal media. Some panels addressed the evolution of daily deals and the looming impact of location-based services. Other sessions focused on the economics of local publishing and lessons learned by successful and failed independent journalism ventures.

A key question threaded throughout the conference was how best to turn local consumers into reliable revenue streams. The most valuable insights for independent publishers in attendance centered around new opportunities for better serving local businesses. Over the course of 20 sessions packed into two days, four themes emerged.

1. Local businesses need hand-holding, full-service partners. Local news sites may have an opportunity to fill that function.

Faye Penn, the founding editor of, a blog based in Brooklyn, NY, came away from the conference with new interest in, a platform publishers can use to help local businesses with everything from a landing page to social media and search engine optimization. She said it’s increasingly clear to her that the path forward for independent publishers is a challenging one.

“At all of these conferences, everyone is looking for an answer that no one really has,” she said. But for Penn, who says she has 60-70,000 unique visitors each month and has earned enough recently to hire an editor, the idea of selling a streamlined service to local businesses is promising.

Photos by Shana Wittenwyler Jeff Jarvis, BuzzMachine, interviews Foursquare’s Evan Cohen

David Pachter, CEO of LocalVox, said that local businesses suffer from an information and skills gap. “They’re looking for an easy, affordable, online marketing solution that lets them feel like they’re accomplishing the transition to online marketing without spending a fortune,” he said, during a panel about alternative revenue models for publishers. LocalVox enables businesses to buy a suite of services for $250 a month, an amount Pachter said they can more than earn back through better local search results and a stronger Web presence.

Patrick Boylan, editor of Chicago’s Welles Park Bulldog, told me he was intrigued by the partnership model presented by, which helped raise the advertiser count for its first partner, Brooklyn’s seven-year-old blog, up past 400. BlankSlate manages sales for Brownstoner, allowing the editors to focus on content while outsourcing the sales process and splitting the revenue. Blankslate developed a service for Brownstoner that enables local businesses to establish an initial Web presence through the directory at $25 a month. Revenue also flows in through real-estate ads and other services for local merchants.

2. Geo-tagging may soon be as important as SEO for local publishers.

Numerous presenters described the imminent impact of location-based services. Alistair Goodman, CEO of Placecast, said it’s a matter of months before businesses will be bidding for passer-by attention. “We’re approaching a time where you’re going to be able to bid on a user on a street corner at a particular point in time in real time,” Goodman said. Placecast already allows businesses to target customers with relevant mobile ads based on their location and the time of day, the weather, the traffic, and other factors.

Given the developing opportunities for targeting readers interested in particular local content, has already made a concerted effort to geo-tag every piece of content it produces. Leela de Kretser, DNAInfo’s editorial director and publisher, said the news startup is on track toward its business goals, and that its sole investor, Joe Ricketts, believes in the long-term profitability of the news business. She and numerous other panelists emphasized that local sales efforts require a major effort to educate merchants on their online marketing options. The influx of short-term daily deals opportunities has added a complication to a market where merchants were already struggling to grasp the available advertising channels.

Panelists described local merchants in major cities as generally bewildered by daily-deal merchants and their persistent sales calls. If you’re a small business getting called upon three to four times a day by a wide range of deals startups, you may struggle to figure out what’s truly in your best interest. To combat this confusion, panelists argued, merchants need the guiding hand of a trusted local publisher to help them cut through the clutter and develop a coherent marketing strategy, reaching their local public through a combination of search, mobile and social advertising.

3. The Daily Deals honeymoon is over.

Rather than just diving deeper into the deals game alongside the 800 deal sites that have launched over the past few years, Perry Evans, CEO of, suggested that publishers and marketers adopt a new tact. Instead of focusing on dangling dangerously low-margin deals at new price-sensitive customers, why not reach out for repeat buyers by aiming special deals at those who have already bought something, to convert them into loyal buyers. Closely provides a customized dashboard for businesses. Evans likened it to a HootSuite for merchants. It allows them to vary the discounts they offer depending on their inventory or how busy they are, and to offer existing customers customized coupons.

The economics of daily deals have changed, said Yipit co-founder Vinicius Vacanti. Whereas Groupon could spend just $2 in marketing costs to acquire its early customers, it now has to spend between $8 and $12, given the changing dynamics of online advertising, Vacanti said. And given that only a quarter of those on its email list buy something, that signifies a cost of $40 per paying customer.

Groupon can’t make enough on the one or two deals that the average customer buys into, given that it splits revenue with merchants, who have already marked the price down by 50 percent. To compound the problem, merchants are finding that, as one panelist put it, signing up for a deal is like taking a high-interest loan. You get lots of money up front for the advance purchases, but then you have to deliver a significant amount of service/product to a subset of customers who are price-sensitive and historically less brand loyal than others who find the merchant through other channels. This rationale is what has led some, including Seth Priebatsch, of the mobile gaming service, to criticize what they call the “Grouponzi” phenomenon.

4. Hyperlocal publishing is as much about sales as about content.

Carll Tucker, CEO of Main Street Connect, said he sees great potential in mid-size, non-urban markets where 150 million Americans live. The 52 sites in his network of local news outlets now work with about 400 advertisers who spend an average of $8,000 a year on advertising with his sites. His sales team aims at hospitals, realtors, and car dealerships, among others, all of which need brand advertising.

For Shawn McGinness, the business manager for St. Louis Beacon, the key lesson from the site’s early progress has been to focus on a few goals and capitalize on internal strengths. The Beacon, which was founded in 2008 and now has 20 employees, including five on the business side, has a $1.5 million budget. McGinness says the Beacon made the mistake of diluting its early focus among too many projects and has since refocused its efforts around a few profitable efforts, including offline events. His three primary tips for independent news organizations were:

  • Ignore everyone else, because what works (or fails) in one place may not in another.
  • Focus on a unique value — what your organization does well.
  • Start out with small projects and gradually improve and expand upon them. 

Click here to see his slides. If you’d like to read more about the Street Fight Summit, I curated 300+ Tweets, photos, slides and other materials from the conference.

Correction: An earlier version of this story misspelled Joe Ricketts. Read more


How to get to $200K: Lessons in building a profitable niche news site

For every splashy new online news venture with a big name backer, from New York’s DNAInfo to Hawaii’s Civil Beat, there are a dozen smaller startups inching their way toward profitability. One such tiny new news venture, operated out of its managers’ homes, is a financial niche site that generated more than $200,000 in revenue last year., a news site aimed at registered investment advisers, has grown steadily since launching in August 2009 by developing strong ad sales and a well-trafficked industry directory.

I talked with RIABiz Editor and CEO Elizabeth MacBride via e-mail to find out how she did it and what she’s learned about the nuances of running a news startup. You can read our edited exchange below.

Jeremy Caplan: How did you get started with

Elizabeth MacBride: In early 2008, the budget for my [contributing editor] job at Crain’s New York Business was cut, and although I was still working for the paper and for other places, I had more time on my hands. An old friend of mine from my Central Penn Business Journal days, Brooke Southall, called and asked if I wanted to join him in a venture: a new B2B online publication targeting investment advisors.

He’d been writing about that rapidly expanding world for about a decade. I knew next to nothing about investment advisors, but I was and am intensely interested in online journalism. Because it costs so little to start an online publication, I thought, “What do I have to lose?” So after talking to some people and doing some research on the industry, I said yes.

In moving from being a reporter and editor to running a niche news site, what did you learn?

Elizabeth MacBride/

MacBride: I’ve always been an editor at heart, even when I was reporting, so some parts of running a niche site weren’t new to me. I had to get us on track organizationally speaking, which meant deciding how many stories we were going to run every day, setting up a story flow, and an editing process — all those basics and many more.

I’d never set up a company before, though — and that’s been a real learning experience. Though I’ve written and edited hundreds of stories about startups, the question of whether to set up an LLC or a S-Corp seemed overwhelming. How does one find a good lawyer? Where do you get libel insurance? I learned that my networks of colleagues were one key source of information. I got our accountant from my next-door neighbor. We joined an association — the Specialized Information Publishers Association — which is how we finally got our libel insurance.

You have financial advertising, a directory, and a partnership with Forbes. How well is the site doing revenue-wise, and how does the situation look going forward?

MacBride: Last year, we had more than $200,000 in revenue. About midway through the year Brooke and I were able to start paying ourselves. We have two other partners, too, our sales director and our chief technology officer.

Our first revenue goal is in 2011 to make enough money to equal what we’d all be making working for someone else. I’m pretty sure we’ll get there this year.

What are the three most challenging aspects of running a startup niche news site?

MacBride: The fact that it’s a huge amount of work is a given. For most of last year, while I was still working nearly full-time for Crain’s to keep the money flowing, I was working till midnight four nights a week and at least six hours on the weekend. That takes a toll, especially if you’re a mid-career journalist with a family.

If RIABiz hadn’t started making money, I would have had to bail out after last year. One good thing about the Internet is that you know fast if it’s going to work — within six months, probably, and definitely within a year. Since the startup costs are low, I think if it doesn’t work, you just move on.

The breadth of skills required is hard. If your goal is just to get a blog site running, you can focus on the writing. But if you want to build a business, that’s different. That means spending a lot more time on organization, marketing, building a team of people, etc.

It is challenging to do the high-level journalism projects that sites that are “backed” by someone can do. I can’t forsee us doing real investigative pieces for a few years.

We break a lot of news in our industry, mostly because people like us well enough to give us stories. We also rely a lot on sheer brain power. We do much more analysis than our competitors, and our stories are different because they have a sense of intimacy and creativity. My partner Brooke is mainly responsible for that tone that’s worked really well for us — he studied many blog sites before establishing RIABiz.

What are some of the key skills that have proven particularly important?

MacBride: The ability to work hard and to multitask. In a startup, it’s important to communicate very clearly with the rest of the team. There’s just no time for misunderstandings, business or personal.

What have you learned about building advertising revenue that might apply to other niche or local news sites?

MacBride: We started with an ad director as a partner, and I can’t imagine doing this without him. He had sold in this niche before and had lots of relationships he could build on.

Maybe the most crucial thing about a startup niche site is picking a niche in which there are advertisers willing to pay high rates. Financial services is obviously one of those. Otherwise, you probably have to go to some kind of subscription model, which would be difficult right off the bat.

What role do directories have as a potential revenue source for niche or local news sites?

MacBride: We are still figuring that out. Our directory — which wouldn’t exist without our fourth partner, a 23-year-old Google Apps engine developer — is mainly a traffic source for us. It gives us a lot of page views. But we are exploring other ways that it could generate revenue. It’s a hard asset for the business, which is a good thing.

What other lessons can you share with journalists starting up news sites?

MacBride: Well — I’d say partnerships are another tricky thing. They are very fluid in the Internet world. We get approached just about every week from someone who wants to partner with us — but what does that mean? We have to drill down to figure out if it’s really to our advantage, which hardly any of them are. Lots of big news organizations want to just take our entire stories and post them on their sites for free with some vague promise of traffic. Not happening.

As an aside, it reminds me of the time when I wrote a story for the Lancaster, Pa., newspaper that relied on long-cultivated sources among the Old Order Mennonites. And a New York Times reporter called me and said, “I”m working on a Sunday feature … can I have all your sources?” I think as a startup it’s easy to get stars in your eyes and not stay level-headed about the best use of your time. Read more


How entrepreneurial journalists can identify opportunities

The appeal of many entrepreneurial ideas is that they solve big problems. These are problems that affect a lot of people in some small way, or a small number of people in a big way. Aim high, right? That’s the conventional wisdom. It sounds good, but isn’t always a realistic way to get started. Information overload, for example, may be a persistent, pervasive problem, but it’s too big to address in a single shot.

Focus first on getting the idea engine running. Rather than swinging for the fences on your first at-bat, begin by scoping out smaller issues that may have slipped under the radar. The ultimate goal is to go from pain to pay. Here are some tips to help you do that:

Find small points of pain

Exercise: Take three index cards. On each write down a small pain point related in some way to journalism that you’ve expressed or heard about recently. Flip the card. Write down three possible elements of a solution.

Pain point example: The landscape of urban commerce changes so quickly that in high turnover areas it’s hard to remember what store or demolished building used to be where. This is a pain point in that commercial transience and the lack of an accessible record of such change disconnect residents from their neighborhood history. If journalism is the provision and organization of a community’s information, couldn’t it somehow remedy this pain point?

Illustration: Three elements of a solution

In thinking about elements of a solution, it occurs to me that there may well be information, images and other structured data that would address this pain point. Such material may exist on Flickr in the form of images of a nearby street that date back a decade or two. It might exist in city documents now being posted online for the first time. Or it might lie in other spots online or offline that I’m not yet aware of.

My second observation is that Yahoo Pipes is an under-appreciated tool with powerful functionality. The service enables people to filter multiple streams of information, like RSS feeds, in a wide range of interesting ways. I’ve used it to filter news, on occasion, but what if it — or some other new tool — were to filter other kinds of community information and images?

My third observation is that the complexity of creating “pipes” may stand in the way of actually putting them to use. I wonder whether new solutions might arise if I could create a simple combination of search terms and filters and package these pipes in a simple, elegant way to share with others.

Start by investigating existing solutions

In the case of any idea seed, the first follow-up step is to investigate existing solutions further. Someone may already have developed a solution to a related problem. If so, there may or may not be room for a portion of your idea. There were plenty of sources of political news before Politico launched. But its founders identified an approach that was fresh, and homed in on pain points among consumers of political news.

The existence of other solutions to a problem you’ve identified can be useful evidence that the problem is real. The key question is whether there are components of the problem that remain to be addressed, or if the solution you have in mind would fill an important gap. The simplest test: Would people pay for your solution?

Focus on little ideas first

Coming up with one big idea can be intimidating. Don’t do it. Gather lots of little idea seeds, one of which may eventually blossom, and capitalize on your strengths as a journalist. Ultimately, having a rich understanding of an array of pain points will help you match problems with solutions, and catalyze your entrepreneurial passion. Read more


How to pitch entrepreneurial ideas to non-journalists

Whenever possible, build the first version of your journalism site/product/service before approaching potential funders. That way you can demonstrate that your product is already working. It’s more effective to talk about what you’re doing now than to speak about what you hope might happen someday.

Whether or not you have live material to show, though, it’s important to be able to articulate your vision. Potential investors — and potential partners or employees — want to hear about your specific plans and strategy. Unlike friends or colleagues, outside investors may care little about your idea’s social value.

Even journalism foundations concerned with social value and sustainability will want to gauge both your business acumen and your project’s financial potential. Foundations don’t mind funding a project’s runway stage, but they want to know how you plan to subsist beyond the project’s infancy. Here are five issues to address in your funding meetings:

Decide whose problem you’re solving

Say you’re pitching a new photo-centric community site for local bird-watching enthusiasts. How many people are you aiming at? Who are these people? What sites do they visit now? What’s their demographic breakdown? If you don’t have at least preliminary answers to these kinds of basic questions, you won’t come across as a credible entrepreneur.

Sculpt your market research into a dozen or so key insights you can communicate clearly to illustrate your audience’s size and scope. Present your audience research in the form of some simple one or two-sentence facts, and note your source.

For Example: “There are 50,000 active birders who live in this urban area, according to a recent survey by the national birding association of record. That figure conforms to other research done recently, including an academic survey by an ornithologist at the local university. In the association’s last survey, the birders in this area were more likely than those based in other cities to report that they didn’t yet have a go-to site for access to local images and information about area birding.”

Save some of your facts/insights to use when answering questions about your market. Your ability to reply intelligently with fact-based insights will say a great deal about your preparation and seriousness.

Focus on the new value you’re creating to support payment

Who will provide revenue for your product or service? If you’re aiming for advertising revenue, how much are target advertisers paying for ad space elsewhere? Research on this point is crucial. It’s also vital to prepare a strong answer to the following question: What new value will you bring to advertisers to make it worth their while to partner with you? Having at least one advertiser who you work with and learn from early on is a valuable way to develop answers to these questions.

You may hope that advertisers will work with you out of friendship, or because of the service you’re providing for a community, or because you’re a great salesperson, but it’s better to rely on a demonstrable value proposition. That entails quantifying, or at least estimating, the additional value you can bring to an advertiser who chooses your option over an alternative.

What it boils down to is that ad customers will seek you out if you reach their audience and save them money in comparison with their available alternatives. They will gladly pay you a share of the value you create by saving money for them. That’s how successful publishing has always worked, and continues to work online. Potential investors want to have a sense of how you will add value for advertisers.

Example: Let’s say a chain of photography stores in the area currently markets to half of the 50,000 local birders through a combination of direct mail, local newspaper advertising, and sponsorship at regional birding events. The chain spent $10,000 to reach the growing community of area birders last year. The campaign brought in about $10,000 worth of business, based on an assessment of discount codes used for purchases. The campaign was therefore of negligible benefit.

To persuade the chain to advertise with our startup venture, we have to provide a clear proposal that details multiple benefits for the advertiser, such that the potential gain outweighs any risk. The solution? Provide the advertiser with a customized, affordable ad plan that combines pay-per-click ads with display ads and event sponsorship, so the chain can reach more potential customers this year at a lower cost.

If you are planning to generate revenue directly from your audience, what do they or others like them already pay for related products? Bone up on current market conditions, ad rates and other relevant facts and figures.

When pitching your ideas, also consider these factors:

Tell stories that grab listeners’ attention

Anecdotes: In their excellent book, “Made to Stick,” Chip and Dan Heath make the case that telling stories is one of the most powerful ways of making a pitch memorable. Any presentation you give should have stories that illustrate the need for your product or its efficacy. Venture capitalists frown on empty jargon, but stories capture people’s attention. Adding stats and specific numbers to your anecdotes generally adds to their impact.

Team: Talk about your partners and the specific achievements that demonstrate their capabilities. Share some highlights about your own background. Detail some specific achievements, even if they occurred in another arena; success reflects well on you and your potential.

Costs: Estimate the key expenses you anticipate you’ll face in the immediate future. Be prepared to articulate what you’re spending and why, and how a potential investment would impact your business.

Perfecting the pitch: Keep your presentation as short and simple as possible. Use few, if any, slides. Rely instead on stories, facts and examples. Focus on the problem you’re solving, rather than your personal motivation. Investors don’t care that you were getting bored doing something else or that you have always wanted to do this. What they want to know is whether or not this project is viable.

Focus on the facts, the market potential, the challenges, the progress that you’ve already made, and the next steps you have planned. Be candid and concise. End by articulating “the ask,” which details what you want from the investor or potential partner. You won’t get what you don’t ask for.

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