1. The state of the universe
  2. Ideas to Businesses
  3. What is an organization?
  4. Operating an organization (of one or many)
  5. Content Focus
  6. Audience
  7. Technology
  8. Marketing
  9. Product Management — Taking the Tech Start-Up Process to News
  10. Revenue Streams
  11. Business Plans (e.g. Putting it all together)
  12. Launch
  13. Ongoing management
  14. Freelancing
  15. Per chapter supporting materials (Uniform across chapters)

The state of the universe

  1. What’s happening now in media?
  2. What are the big problems to be solved?
  3. How does an entrpreneur approach a big problem and come up with a solution? The roadmap for this book.

Ideas to Businesses

  1. Generating a business idea
  2. Introduction to multiple insights that are then built into ideas in many industries and over time, think from Bloomberg to Amazon to Stratechery to The Information to The Texas Tribune to NPR.
  3. Triple bottom line thinking in Journalism
    1. All journalistic enterprises — for profit and non-profit — are actually triple bottom line entities
      1. What it is (Triple-Bottom Line Thinking)
      2. Where it comes from (Origins and development)
      3. Why it matters to journalism
      4. Limitations and challenges
    2. Business Isn’t For Other People (it’s for you)
  4. Validating your idea, using the Lean Startup Methodology and customer discovery process.
    1. Talking to customers
    2. Filling out business model canvas
    3. Identifying the value proposition and segmenting the customers to find market fit
    4. Sizing the market
    5. Developing a Minimum Viable Product
    6. Knowing when you are ready to move forward

What is an organization?

  1. Even single-person businesses interact with a wide array of other people, making it a virtual organization
  2. Theory of the firm (e.g. when transaction costs are lower being in the same organization)
  3. Kinds of organizations
    1. Legal entities
    2. Structures
  4. Goals
  5. What is an entrepreneur? What is management?

Operating an organization (of one or many)

  1. Goals, measurement
  2. What is an entrepreneur? What is management?
  3. What are parts?
    1. Editorial
      1. Content (reportorial/editorial/creative/etc.)
      2. Design
      3. Technology/Engineering
    2. Sales
    3. Marketing
    4. Product
    5. Finance/Accounting
    6. Administration
    7. Legal

Content Focus

  1. Entrepreneurial media organizations can’t cover the world, they must do one thing (practically, staffing, marketing, audience, etc.)
  2. Goldilocks and focus (too small and there’s not enough revenue, too large and it’s impossible to do well)
  3. What is a vertical or niche in the modern landscape?


  1. How do you define an audience?
  2. How do you learn about them?
  3. How do you measure them?


  1. CMS
  2. CRM
  3. Email
  4. Advertising
  5. Operational Tech
    1. Team communications
    2. Accounting/Payroll
    3. Other?


  1. Intimately related to audience, but also speaking to other critical groups to your success (funders, other entrepreneurs, other publishers, other marketers looking to reach your audience etc.)
  2. Customer centricity as a lens for all marketing activity
  3. Classical Marketing Fundamentals
    1. Place
    2. Product
    3. Promotion
    4. Price
    5. Brand

Product Management — Taking the Tech Start-Up Process to News

  1. What is a product?
  2. Product management theory
  3. Product lifecycle
  4. Measurement
  5. Testing
  6. Etc.

Revenue Streams

  1. Donations
  2. Grants
  3. Consulting
  4. Events
  5. Advertising
  6. Subscriptions
  7. Communities (e.g. paid slack)
  8. Affiliate links
  9. Branded content
  10. Syndication

Business Plans (e.g. Putting it all together)

  1. For profit/non-profit
    1. Why choose one or the other?
    2. Less relevant than you might think
  2. Audience
    1. B2B, B2C
    2. Specific people (personas)
    3. Market sizing
    4. Monetization with those people in mind
  3. Products
    1. Web? YouTube? Podcast? Newsletter? Instagram Stories?
    2. CAUTIONARY TALE: tech platforms make and take value — ensure you control your own destiny
    3. What’s the best format to reach your audience
  4. Go to market
    1. Marketing
    2. Partnerships
    3. Distribution/syndication
    4. Design
    5. The Pitch Deck
  5. Financing
    1. Bootstrapping
    2. Venture
    3. Other investors


  1. An opportunity for publicity
  2. Punchlists

Ongoing management

  1. Quarterly Check Ins
  2. Annual reports/goals
  3. Setting up a board of advisors
    1. What to look for?
    2. What to ask them?


  1. An age-old journalistic enterprise of one
  2. How it works
  3. Contracts
  4. Ownership of social media accounts
  5. Copyrights
  6. Insurance
  7. Expertise
  8. Safety
  9. Examples

Per chapter supporting materials (Uniform across chapters)

  1. Sample syllabus (for the book and examples from as many other courses as we can find)
  2. Sample assignments
  3. Reading list
  4. In-class activities
  5. YouTube Videos (and/or lectures)
  6. Quizzes (DB of quiz questions, randomized per instructor)
  7. Case studies (HBS style?)
  8. Big Ideas / Controversies / Debates each semester