Newsletter Writer

C

Contrarian Thinking

Newsletter Writer

austin, TX
Part Time
Paid
  • Responsibilities

    Position Overview

    Contrarian Thinking is looking for a business-minded writer with high-level AI skills who can help us scale two of the most-read business newsletters in the world.

    You'll take big concepts and turn them into clear, compelling, human-written long-form newsletters that people actually read, save, and forward.

    We are an AI-forward company that believes in using AI as a direction for first drafts that are then tailored and leveled-up. If you know how to prompt but don't know how to think, this isn't the role.

    If you know how to think and know how to use AI as leverage, you'll thrive here.

    What You'll Actually Do

    If you worked here this month, you might have:

    • Taken an AI-generated first draft of a business acquisition and rewritten it into a sharp, narrative-driven newsletter
    • Layered in current events, market trends, or regulatory shifts to make the piece timely and relevant
    • Reworked an internal case study into a mass-appeal breakdown for hundreds of thousands of readers
    • Tightened a rambling AI draft into a clean framework readers could actually apply in their own lives
    • Collaborated with leadership to sharpen POV, accuracy, and edge

    Depending on skill level and interest, this role may expand into:

    • Ad copy
    • Short-form social media scripts
    • YouTube long-form writing
    • Editorial planning and content strategy

    Core Responsibilities

    AI-to-Human Editorial Translation

    • Use AI to accelerate research and drafting then apply judgment, taste, and clarity to finish the work
    • Know when to trust the model and when to override it

    Newsletter Writing

    • Write high-impact long-form newsletters on business buying, scaling, and ownership
    • Balance data, storytelling, and actionable frameworks

    Business & Market Analysis

    • Relate current events, deal flow, and market trends to real-world ownership opportunities
    • Spot what actually matters and ignore the noise

    Case Study Rewrites

    • Take dense or technical case studies and make them understandable, engaging, and widely applicable

    Editorial Judgment & Voice

    • Maintain a sharp, contrarian, intelligent tone
    • Ensure everything sounds like a human with authority not a model

    Who This Is For

    This is not a junior writing role.

    You should have:

    • Proven experience writing long-form business or financial content
    • Strong critical thinking and editorial instincts
    • High comfort using AI tools for research, synthesis, and first drafts
    • The ability to rewrite, restructure, and improve AI-generated content
    • A business mindset. You understand entrepreneurs, and are interested in helping them learn and grow.

    Bonus if you've worked with:

    • Newsletters, media brands, or founders at scale
    • AI-assisted editorial workflows
    • Business acquisitions, investing, or SMB operations

    What We Do

    Contrarian Thinking helps people buy businesses, build cash flow, and think independently.

    • 800K+ weekly newsletter readers. We have two weekly newsletters
    • 2.05M YouTube subscribers, 3M Instagram followers
    • 12M+ followers across platforms
    • Top-50 business podcast
    • Courses, community, and an active investment fund

    We don't just write about deals — we do them.