Position Overview

Contrarian Thinking is looking for a business-minded writer 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, long-form newsletters that people actually read, save, and forward.

What You'll Actually Do

If you worked here this month, you might have:

Interviewed members of our community and turned it into a newsletter that connects with a broad audience
Ideated and created a database with research and topics for future newsletters
Created a newsletter that is timely, related to current events, market trends, or regulatory shifts
Reworked an internal case study into a mass-appeal breakdown for hundreds of thousands of readers
Delivered a newsletter with 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

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 that become high-concept, human-written second drafts
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.

Contrarian Thinking

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Senior Newsletter Writer