Senior Newsletter Writer

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.

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
• You Tube long-form writing
• Editorial planning and content strategy

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

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.

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

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

• 800K+ weekly newsletter readers. We have two weekly newsletters
• 2.05M You Tube 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.