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.
