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WINDY CITIZEN
How not to suck at online publishing
         and advertising

            Brad Flora
            @bradflora
           @windycitizen
Background
•Founder, Windy Citizen.com
•Prior: Princeton English (‘04), College
admissions officer, Northwestern Journalism
(’08)
•Recently: Won 2010 Knight News Challenge

•Find and pass along what’s hot in Chicago
•Twitter: @windycitizen
•Founded in May ‘08
•Bootstrapped company based in Chicago
•Niche social network, 10,000 registered
users, 100,000 uniques/month
What I did and learned in the last
           two years.
Context
•Current iteration not actually first idea
•Not an engineer
•No advertising spend
•No investment capital
•Semi-hostile environment (news organizations not
interested in covering)
•Mostly done by non-technical people with some
guidance but no prior experience
Environment: 2008
•Tribune + Sun-times in bankruptcy
•City blogs on the rise (Chicagoist, Gapers Block)
•Dozens of young, underemployed writers
•Seemed like a no-brainer
Faulty Assumptions
•Started with a pretty naive take on things
   •Traffic = Money
   •Content = Traffic
   •Journalism background gives me access to content
   •High quality content -> The Google -> Traffic -> ??? -> Profit!
"I don't do local politics. That
        ****'s boring.“

-My sister's cute friend (20-something Chicago-based consultant)
Building a local audience is HARD
Lessons Learned
Lessons Learned
•Single-Threaded = Death
Lessons Learned
•Single-Threaded = Death
  •If 1:1 relationship between growth and
  your effort, you’re doomed.
  •If single point of failure, you’re doomed.
Lessons Learned
•Single-Threaded = Death
  •If 1:1 relationship between growth and your
  effort, you’re doomed.

•No Point of View = Death
Lessons Learned
                   Single-Threaded
•Single-Threaded = Death
  •If 1:1 relationship between growth and your
  effort, you’re doomed.

•No Point of View = Death
Average 20-something city dweller thinks:



"I don't do local politics. That
         ****'s boring.
Have you heard of Groupon?“

-My sister's cute friend (20-something Chicago-based consultant)
Lessons Learned
•Single-Threaded = Death
Lessons Learned
•Single-Threaded = Death
•No Point of View = Death
Lessons Learned
•Single-Threaded = Death
  •If 1:1 relationship between growth and your
  effort, you’re doomed.

•No Point of View = Death
Lessons Learned
STRONG POV
   •Single-Threaded = Death
     •If 1:1 relationship between growth and your
     effort, you’re doomed.

   •No Point of View = Death
Lessons Learned
•Single-Threaded = Death
  •If 1:1 relationship between growth and your
  effort, you’re doomed.

•No Point of View = Death
Lessons Learned POV
                    WEAK
•Single-Threaded = Death
  •If 1:1 relationship between growth and your
  effort, you’re doomed.

•No Point of View = Death
Average 20-something city dweller thinks:



"I don't do local politics. That
         ****'s boring.
Have you heard of Groupon?“

-My sister's cute friend (20-something Chicago-based consultant)
The Internet: Where sane people go
to read and experience crazy things.
Lessons Learned
•Single-Threaded = Death
•No Point of View = Death
Lessons Learned
•Single-Threaded = Death
•No Point of View = Death
•Make something people want
Public Enemy #1: Journo-Think
  Journalist-turned-entrepreneur thinks:

“Local public affairs reporting is important!
     Therefore, there’s demand for it.”
Average 20-something city dweller thinks:




"I don't do local politics. That
         ****'s boring.
Have you heard of Groupon?“
Average 20-something city dweller thinks:



"I don't do local politics. That
         ****'s boring.
Have you heard of Groupon?“

-My sister's cute friend (20-something Chicago-based consultant)
Plan B
•Place to share your favorite local links
   •Addressed single-threaded problem
   •Addressed point of view problem
•The Year
   •Phase 1: The Routine
   •Phase 2: Ads
   •Phase 3: Sell, sell, sell
"I don't do local politics. That
        ****'s boring.“

-My sister's cute friend (20-something Chicago-based consultant)
Plan B
•Place to share your favorite local links
   •Addressed single-threaded problem
   •Addressed point of view problem
•The Year
   •Phase 1: The Routine
   •Phase 2: Ads
   •Phase 3: Sell, sell, sell
The Pivot
Problem:
Had to figure out how to make
 money. Wanted to sell ads.
The Problem With Banner Ads


•Learned early on that banner ads weren't going to
work for Windy Citizen
•Pricing is terrible
•Audience too small to get into large ad networks that
actually pay
•Ad networks serve irrelevant ads
•Needed to do direct sales, needed to have a product
that would justify direct sales
How do you add value to an ad?
 •Advertising friends: "Targeting!"
 •Another idea, what if you gave them more control
 over their ad creative?
 •People pay for convenience, not the actual product,
 what if that applied to an online ad?
Real-Time Ads
   •Launched first one in September
   '09
   •Price it on a negotiated monthly
   basis rather than CPM
   •Improved the design
   •Numbers steadily improved
Opportunity
Knight News Challenge
•Annual innovation challenge (http://newschallenge.org)
•$5 million dollars to new ideas for the news industry
•Funded Everyblock
Knight News Challenge
•A tortured history
Knight News Challenge
•A tortured history
   •2008: Applied with Windy Citizen Idea (Cut in first round)
Knight News Challenge
•A tortured history
   •2008: Applied with Windy Citizen Idea (Cut in first round)
   •2009: Applied a year into Windy Citizen (Cut in final round)
Knight News Challenge
•A tortured history
   •2008: Applied with Windy Citizen Idea (Cut in first round)
   •2009: Applied a year into Windy Citizen (Cut in final round)
   •2010: Applied with a business making (some) money…
WINNER!
NowSpots: New Company (!)
          •Providing real-time advertising
          tech to newspapers and other
          local publishers


          Going to save newspapers
          by giving them better,
          smarter tech.
NowSpots: New Company
        •Providing real-time advertising
        tech to newspapers and other
        local publishers

        •Better prepared this time
        around
           •Able to draw on contacts made
           through WC to find first customers
           and build our founding team
        •Web: NowSpots.com
        •Twitter: @nowspots
        •Launching Fall 2010!
Digging for gold -> Selling Shovels
NowSpots.com
    •Web: NowSpots.com
    •Twitter: @nowspots
    •Launching Fall 2010!

    If you care about the
    future of newspapers,
    join our e-mail list.
NowSpots: New Company
        •Providing real-time advertising
        tech to newspapers and other
        local publishers

        •Better prepared this time
        around
           •Able to draw on contacts made
           through WC to find first customers
           and build our founding team
        •Web: NowSpots.com
        •Twitter: @nowspots
        •Launching Fall 2010!
Recap
•Your first idea really does probably suck.
•Single threaded doesn’t work.
•You have to have a point of view.
•If people aren’t reading and sharing your content, it’s
probably because your stuff sucks.
•The only thing worse than making these mistakes is
chickening out for fear of making these mistakes.
•While working on your less great ideas, you might
come up with much better ones.
Thank You!
Questions?
Contact me on Twitter:
     @bradflora

 Get your Chicago fix:
   @windycitizen

Help save newspapers!
     @nowspots

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Brad Flora: How to not suck at online advertising and publishing

  • 1. WINDY CITIZEN How not to suck at online publishing and advertising Brad Flora @bradflora @windycitizen
  • 2. Background •Founder, Windy Citizen.com •Prior: Princeton English (‘04), College admissions officer, Northwestern Journalism (’08) •Recently: Won 2010 Knight News Challenge •Find and pass along what’s hot in Chicago •Twitter: @windycitizen •Founded in May ‘08 •Bootstrapped company based in Chicago •Niche social network, 10,000 registered users, 100,000 uniques/month
  • 3. What I did and learned in the last two years.
  • 4. Context •Current iteration not actually first idea •Not an engineer •No advertising spend •No investment capital •Semi-hostile environment (news organizations not interested in covering) •Mostly done by non-technical people with some guidance but no prior experience
  • 5. Environment: 2008 •Tribune + Sun-times in bankruptcy •City blogs on the rise (Chicagoist, Gapers Block) •Dozens of young, underemployed writers •Seemed like a no-brainer
  • 6. Faulty Assumptions •Started with a pretty naive take on things •Traffic = Money •Content = Traffic •Journalism background gives me access to content •High quality content -> The Google -> Traffic -> ??? -> Profit!
  • 7. "I don't do local politics. That ****'s boring.“ -My sister's cute friend (20-something Chicago-based consultant)
  • 8. Building a local audience is HARD
  • 11. Lessons Learned •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •If single point of failure, you’re doomed.
  • 12. Lessons Learned •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 13. Lessons Learned Single-Threaded •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 14. Average 20-something city dweller thinks: "I don't do local politics. That ****'s boring. Have you heard of Groupon?“ -My sister's cute friend (20-something Chicago-based consultant)
  • 16. Lessons Learned •Single-Threaded = Death •No Point of View = Death
  • 17. Lessons Learned •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 18. Lessons Learned STRONG POV •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 19. Lessons Learned •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 20. Lessons Learned POV WEAK •Single-Threaded = Death •If 1:1 relationship between growth and your effort, you’re doomed. •No Point of View = Death
  • 21. Average 20-something city dweller thinks: "I don't do local politics. That ****'s boring. Have you heard of Groupon?“ -My sister's cute friend (20-something Chicago-based consultant)
  • 22. The Internet: Where sane people go to read and experience crazy things.
  • 23. Lessons Learned •Single-Threaded = Death •No Point of View = Death
  • 24. Lessons Learned •Single-Threaded = Death •No Point of View = Death •Make something people want
  • 25. Public Enemy #1: Journo-Think Journalist-turned-entrepreneur thinks: “Local public affairs reporting is important! Therefore, there’s demand for it.”
  • 26. Average 20-something city dweller thinks: "I don't do local politics. That ****'s boring. Have you heard of Groupon?“
  • 27. Average 20-something city dweller thinks: "I don't do local politics. That ****'s boring. Have you heard of Groupon?“ -My sister's cute friend (20-something Chicago-based consultant)
  • 28. Plan B •Place to share your favorite local links •Addressed single-threaded problem •Addressed point of view problem •The Year •Phase 1: The Routine •Phase 2: Ads •Phase 3: Sell, sell, sell
  • 29. "I don't do local politics. That ****'s boring.“ -My sister's cute friend (20-something Chicago-based consultant)
  • 30. Plan B •Place to share your favorite local links •Addressed single-threaded problem •Addressed point of view problem •The Year •Phase 1: The Routine •Phase 2: Ads •Phase 3: Sell, sell, sell
  • 32. Problem: Had to figure out how to make money. Wanted to sell ads.
  • 33. The Problem With Banner Ads •Learned early on that banner ads weren't going to work for Windy Citizen •Pricing is terrible •Audience too small to get into large ad networks that actually pay •Ad networks serve irrelevant ads •Needed to do direct sales, needed to have a product that would justify direct sales
  • 34. How do you add value to an ad? •Advertising friends: "Targeting!" •Another idea, what if you gave them more control over their ad creative? •People pay for convenience, not the actual product, what if that applied to an online ad?
  • 35. Real-Time Ads •Launched first one in September '09 •Price it on a negotiated monthly basis rather than CPM •Improved the design •Numbers steadily improved
  • 37. Knight News Challenge •Annual innovation challenge (http://newschallenge.org) •$5 million dollars to new ideas for the news industry •Funded Everyblock
  • 38. Knight News Challenge •A tortured history
  • 39. Knight News Challenge •A tortured history •2008: Applied with Windy Citizen Idea (Cut in first round)
  • 40. Knight News Challenge •A tortured history •2008: Applied with Windy Citizen Idea (Cut in first round) •2009: Applied a year into Windy Citizen (Cut in final round)
  • 41. Knight News Challenge •A tortured history •2008: Applied with Windy Citizen Idea (Cut in first round) •2009: Applied a year into Windy Citizen (Cut in final round) •2010: Applied with a business making (some) money…
  • 43. NowSpots: New Company (!) •Providing real-time advertising tech to newspapers and other local publishers Going to save newspapers by giving them better, smarter tech.
  • 44. NowSpots: New Company •Providing real-time advertising tech to newspapers and other local publishers •Better prepared this time around •Able to draw on contacts made through WC to find first customers and build our founding team •Web: NowSpots.com •Twitter: @nowspots •Launching Fall 2010!
  • 45. Digging for gold -> Selling Shovels
  • 46. NowSpots.com •Web: NowSpots.com •Twitter: @nowspots •Launching Fall 2010! If you care about the future of newspapers, join our e-mail list.
  • 47. NowSpots: New Company •Providing real-time advertising tech to newspapers and other local publishers •Better prepared this time around •Able to draw on contacts made through WC to find first customers and build our founding team •Web: NowSpots.com •Twitter: @nowspots •Launching Fall 2010!
  • 48. Recap •Your first idea really does probably suck. •Single threaded doesn’t work. •You have to have a point of view. •If people aren’t reading and sharing your content, it’s probably because your stuff sucks. •The only thing worse than making these mistakes is chickening out for fear of making these mistakes. •While working on your less great ideas, you might come up with much better ones.
  • 49. Thank You! Questions? Contact me on Twitter: @bradflora Get your Chicago fix: @windycitizen Help save newspapers! @nowspots