My Questions for Entrepreneurs - CollabSpace Chicago

A few weeks ago, I helped to lead a PBS MediaShift organized Collab/Space event in Chicago.  The event offered nine entrepreneurs - media startups of varying kinds - an opportunity to present their ideas/projects and field questions from an audience filled with fellow entrepreneurs, media veterans, and other smart folks.

Each of the nine startups is given five minutes to present their idea/project and then ten minutes to answer questions.  Here is an overview of the nine entrepreneurs who were the focus of the event. The afternoon is spent working with the entrepreneurs in groups to address various project-related challenges.

Here is the Storify of the event.

My role during the CollabSpace is to process everyone’s input and then pose questions/offer feedback on different ideas or priorities that these startups should consider addressing.  My questions/notes/suggestions form the basis of our afternoon workshop sessions - but also hopefully just spur thinking among everyone involved about ways to move the entire conversation forward.

I have pulled together my questions/notes for each of the startups below - I am sharing them in hopes it helps those entrepreneurs, and anyone else trying to build a media company, or engage an audiences in a meaningful way - think about things a little differently.

Let me know what you think or if you have any questions or ideas to add.



Q: Are the current definitions/classifications of ‘high value’ readers sufficient/accurate?

Q: Do publishers understand the problem of engagement with audiences (or are they trying to move audience to what publishers are already comfortable with)?

Q: What else do we need to know about audience behavior (beyond media consumption) to transform loyalty?

Q: Do publishers understand how to monetize loyalty?

Q: Is there enough content coming of publishers to feed engagement/loyalty?  Is there a way for multiple media companies to share content (and data about their respective audiences) - so they can also share the context (e.g. open vs. closed systems)?

Q: How does the element of human curation scale (particularly when media companies are cutting back) while also maintaining quality?

Q: Could you partner and provide context with non-media companies/publishers (e.g. Major League Baseball, GE, J-Crew, etc) with the same success?

Q: How does the tool/system get smarter based on user behavior and data (so that the same stories don’t continue to pop up after they have been read, or ignored)?

Q: How do you position the tool (and its value) to help get bigger clients… and transform into something even larger? What is your ambition beyond just building a successful business?

Q: Are there trends/data that you can gather and share/promote, or sell to help shape the way the industry things about context?



Q: Does 'easy’ and 'good’ happen for everyone?  What knowledge/perspective do customers need to have in order to take full advantage of the tool?

Q: Is there a risk that visuals are a fad? How do you continue to evolve how people think about visualization so you can shape the industry, not just capitalize on the interest as it is presented?

Q: Do customers know how to monetize visuals (directly or indirectly)? Is that important for customers to understand so that they appreciate the value of visualization - and not just see the cost of the tool and its impact on their bottom line?

Q: Are there major client target groups (beyond media) that you would see the tool being valuable to as well (e.g. if every company is a media company, how could Data Visual help a retailer, or auto company, to present information differently)?

Q:  Can you teach old-school journalists to appreciate, and embrace, data visualization (or is the success of the tool dependent on more data-oriented people entering journalism)?  How much training/education and support is required for someone to take full advantage of the tool and create great visualizations?

Q: What other advisers/partners could you work with (beyond media) to expand your thinking and perspective?  What other industries have shifted their methods of engaging consumers – and emphasized visuals – that people in media could learn from?

Q: Is there a scale opportunity for the company in helping customers to make larger, more complex graphics? Is there a risk that the expectations get too high for what basic graphics can achieve?

Q: Is there a service component (and business opportunity) for consulting, providing support to people on creating better graphics?

Q: How does maintaining customer loyalty play into long-term vision/plan for the company? Do you have to go beyond a strong transactional connection to customers to succeed?

Q: Is there an opportunity to show/consume what is important, not just what is most current?  Can you track behaviors and actions around themes/topics and not just specific events (that everyone else is already looking at, responding to)?

Q: In addition to focusing on limited time, is it possible to use the same aggregation to get people go deeper into topics/issues?

Q: Is there a way to act as a service where news organizations could request user-generated coverage of topics (or explore topics to see if something would be popular if covered)?  Could you help to shape the news, instead of just providing content?

Q: How do you address credibility, rights/permissions (and monetization) to make publishers comfortable?

Q: How do you avoid the firehose problem (best vs. first) - and end up elevating bad, or inaccurate user-generated coverage of an event or happening?

Q: How might you use the data/aggregation to create trend reports (both for marketing the tool, as well as potentially to monetize directly by selling to customers)?  Is there a way to add 'meaning’ to the real-time aggregation?

Q: How do you define/explain the value of this curation (compared to Beats by Dre, or YouTube)?

Q: Can you create a validation system for contributions so that customers can sort for diversity, geographic location?

Q: Is there something especially valuable that news organizations want/need to crowdsource that you could aggregate - beyond photos? Quotes? Opinions? Ideas?

Q: How do you create communities (around topics, experts, etc) that can build credibility and reflect the profile of what news organizations want/need?

Q: Can you offer the same thing for non-news organizations (e.g. Major League Baseball, GE, J-Crew)?

Q: How can you define/shape the idea of quality in terms of the use of user-generated content? Can you maximize diversity (racial, ethnic, economic status, etc), geographic location, expertise? 


Q: How do you get publishers to focus on new audiences (not just optimizing for existing/known audiences)?  What other data (shopping, voting, locations, etc) do you need to consider along with media consumption? 

Q: How do you teach publishers to think like retailers – predicting and/or shaping behaviors, instead of just responding to existing signals?
Q: How do you roadmap/define the monetizable behaviors to what publishers need?  X = subscription? Y = loyalty?

Q: How do you create a shared understanding - and usage - between the business/marketing side of the operation and the editorial (so that they don’t fight each other and undermine the value of the tool)?

Q: How do you sync up online and offline (print) data, to get a more complete pictures (magazines vs. web vs. social)?

Q: Can you answer the 'why’ question so publishers don’t just read the data, then chase a signal? How can you add 'meaning’ to the analysis?

Q: Is there a global trend/white label serve opportunity to a) build a better database for media - one that includes more than just individual company data, and b) explain the larger behavioral trends of consumers so media can plan accordingly?

Q: What should publishers be tracking that they aren’t currently tracking (and/or what is required for people to get really good data)? What are the unknown unknowns?

Q: How do you integrate qualitative data with quantitative data - to show depth, or impact/influence on an issue or business (e.g. sold more stuff)?

Q: What new/different media consumptions behaviors need to be defined, better understood – so people can expand their view of data?  What other things should we be measuring that we aren’t currently (particularly with a goal of moving away from measuring activity only)?

Q: Is there a central nervous system that small publishers could tap into in aggregate?  Could become (or include) a think tank or data intelligence operation, and make connections with existing data from non-media sources?  What other trends/factors could you provide (e.g. weather)?

Q: What skills/testing approaches and actionable suggestions could you make to help influence actions? How do you connect the analysis to measurable changes in behavior, or critical actions being taken?


Q: Is there a model where you license the approach for other languages - beyond Spanish?

Q: Are there connections between media and financial activity that you need to make (e.g., banks, etc)?

Q: Are you consumer focused or should you consider being industry focused (e.g. what Skift does for Travel) – or even take a 'train the trainer’ type approach to influence the actions companies take.

Q: What is your theory of change (e.g. Introduction - Awareness - Framing - Understanding - Engagement - Action)? How does your content result in your desired outcomes?

Q: Do you build a destination or do you build a source of good content and push/syndicate that content to organizations that have access to the audience already?

Q: Do you think people want this information? How do you relate this need to the most pressing challenges individuals/families already face? How do you make it relevant without undermining the quality and focus of your content?

Q: Do you build a media platform or an educational tool (or can the same thing accomplish both)?  Centralized vs. distributed? Think tank vs. publishers?

Q: Who are good models/guides for how this might be accomplished (e.g. Marketplace or American Public Media?  What non-media models might be useful to look at  (e.g. Story of Stuff)?

Q: Are there moments of opportunity that are more important than others in this conversation (e.g. at the grocery store vs. school vs. home vs. hearing from peers)?  Does a model exist for teaching behavior change around financial literacy that you could build the media around?

Q: How do you create the demand for this? How do you build curiosity - either among target consumers, or partners?


Q: How can you define (or re-define) innovation in terms that help media? Do startups need to do a better job framing innovation to relate to need (e.g. problem solving), and what role can you play in that framing?

Q: Can you aggregate the creative briefs you prepare to help identify friends, and market need to inform investors and entrepreneurs?

Q: How do you get 100% among startups (not just those who opt in to participate)? How do you become THE clearinghouse for startup matching? How do you become the Better Business Bureau for startups?

Q: Could you build an advisory board network (to pair people with expertise, but not necessarily dollars to invest)?  What about creating a speakers bureau - to ensure that a more diverse group of people participate in tech, marketing, other conferences and discuss media-related issues?

Q: How might you adjust your model (instead of being a non-profit, what could you do to maximize revenue) – by selling data, providing more direct matchmaking support between investors and entrepreneurs?

Q: How could you use the data that you collect on startups to identify areas of need for individual startups to then address? Could you use your data from the creative briefs/profiles to identify what investors respond to most when reviewing a startup, and help guide entrepreneurs to focus accordingly?

Q: Is there a theory of change/model of success that you use (or could create) to help determine whether a startup is successful?  A grading standard?


Q: How do you apply your local focus to other emerging markets (e.g. Pittsburgh, Omaha, Oklahoma City, etc) - where there is similar need/opportunity?

Q: How do you learn from and/or compare with and/or feed into other startup/tech-focused media (e.g. Re: Code, The Information, PandoDaily, VentureBeat, etc)? How do you become the local voice that allows them to go deeper into coverage without expanding their operations?

Q: What other new media focused sites could you learn from (e.g. Gawker, 120 Sports, Vox, etc)?

Q: What is the product or coverage opportunities – print, long-form, weekly editorial focus – that prevents you from becoming just another local tech blog (that could be replicated by a more well-financed competitor)?  What can be truly unique about your focus - so that there is something only you can create (because of local connections, or editorial bent)?

Q: What other ways could you make money (events, salons, briefings, news-as-a-service)?

Q: How do you monetize gossip without undermining your brand? How do become TMZ without becoming TMZ? 

Q: How do you grow and not lose the local, smart, connected feel that you have established?  Alternatively, how could you become super exclusive w/access (e.g. Clinton Global Initiative)

Q: What types of actions could your newsletter drive?  What data analysis/influencer trend shaping role could you play? 

Q: What won’t you do?


Q: How do you serve a broad audience (e.g. 23-40 year olds) with a single approach? How could you break down the audience into smaller groups (and not just around age, but maybe status in life – single vs. in a relationship vs. married vs. with kids)?
Q: How much do you know about what young people do with information after they consume it? How do you shape your content/experiences (online and offline) to encourage sharing?

Q: How do you become king/queen-maker, not just someone who covers what is happening? What is truly unique about your approach (Q&A, Long-format, images, data, etc) that will make people want to share exclusively with you?

Q: What niche(s) aren’t being covered within your area of focus? How do you create a new approach, or a spin/improvement on existing approaches to differentiate yourself (e.g. Humans of New York, Skimm, Gawker, etc)?

Q: How do you establish an editorial voice that remains authentic to the audience you are service - especially as you grow?  How do you maintain an edge/personality?

Q: What angle of philanthropy isn’t being covered? What focus could you take (e.g. what organizations need board members) that nobody else is taking – and that aligns with what your audience wants/needs?

Q: What is your 'big bang’ idea or moment? What makes you a must-read for everyone?  What won’t anyone else do - that will help to put you on the map (and catapult you to next level)?

Q: What sub-editions/focus areas could you 'own’ and go deeper on as part of your coverage (instead of rolling everything up into one main editorial efforts?  Finance? Arts? Real Estate? Philanthropy? Sports? How could you look at building a network/empire - with the right voice, etc - rather than just a single site?


Q: How do you reach every likely solar customer (100%)? How do you create new potential customers for solar?

Q: Could you provide an industry-focused voice (like what Skift is doing for travel) – and try to change the industry, instead of focusing on the consumers?

Q: What about a print/offline component - a kit, or other support materials? How do you extend the conversation beyond just being a source for research, to ensure a greater amount of influence on purchase decisions and other behaviors?

Q: Could you build/foster a community around solar - and facilitate conversation and collaboration among consumers, instead of just providing editorial coverage?

Q: Is there a customer service component - a live chat, help line (e.g. the Butterball Hotline) for solar consumers?

Q: Why not have a bias? Why not be Curbed for solar, and give the coverage of the work more of an edge, a voice?  How do you strike a tone that resonates/stands out among consumers (e.g. humor, cynicism)? Is there value in trying to make this conversation have more mainstream appeal to people who are not already self-interested and self-motivated in pursuing solar power options?

Q: Where/when does the 'solar moment’ happen and how do you capitalize? What are the behaviors that consumers need to take (to move from not-interested to considering to committed to taking actions) and how do you organize around that journey?

Q: Are there different formats (video, curated reads, etc) that will help to make the solar power conversation even more compelling? How do you aggregate information in new ways, to make the entire conversation more accessible?

Q: Who are the partners that could do your marketing (e.g. you become embedded media service vs. independent journalism entity)? What co-opetition options exist that would allow you to do strong editorial work, without having to also build a following on your own?

Q: What other models are worth exploring - TheKnot, BabyCenter, etc?

Q: How could you take a truly local focus - capitalizing on the markets where the highest concentration of likely solar consumers already exist, or where the value of solar energy is greatest? Where are those areas of density,and how might you localize your coverage/voice to maximize interest and impact?
FINAL WORD: The next CollabSpace event will be held November 6th in DC - with a focus on open data, collaboration and visualization. I hope you will consider joining us.