Nicolas Cole grew up sick. Undiagnosed Celiac Disease kept him home from school for years - which meant he had a lot of time to sit alone with a computer. While other kids were learning to play high school sports, Cole was learning to write. While other teenagers built their social lives, he built a World of Warcraft blog with 10,000 daily readers. He was 17 years old. The internet was already his arena.
It wasn't easy getting there. He fractured his spine twice playing hockey - once at 14, once at 17. The competitive drive that had him training to go pro redirected instead toward something you don't need a body for. He could still compete. Just not on ice.
He enrolled at the University of Missouri in 2008, left after a year, transferred to Columbia College Chicago to study Fiction Writing, and spent a semester abroad in Prague and Florence - where he wrote the first 500 pages of what would eventually become his memoir. He graduated in 2013, took a copywriting job at a boutique Chicago ad agency, and quietly started writing on Quora every single day.
In 2015, Quora's team privately invited him to an event in New York. The head of their Top Writers program pulled him aside and told him something that would change everything: out of 200 million users on the platform, Nicolas Cole was the most-read writer of them all. He hadn't known. He had just been writing.
That moment crystallized what Cole had been doing instinctively - what he would spend the next decade teaching others. Writing in public, using existing platforms with existing audiences, treating every post like a rep at the gym. Not waiting for permission. Not hiding drafts in a notebook. Shipping daily and letting the data teach you what works.
By 2016, Inc. Magazine gave him his own column. He wrote 400+ pieces, became one of their top 10 most-read contributors, and his work started appearing in TIME, Forbes, Fortune, Harvard Business Review, Fast Company, and CNBC. Simultaneously, he self-published his memoir, "Confessions of a Teenage Gamer" - a book that had taken four years of near-daily work to write.
Then a 60-year-old entrepreneur found him on Quora and asked if he'd help ghostwrite some business lessons. That conversation launched Cole into ghostwriting - and eventually into Digital Press, a full-service content agency he co-founded, scaled to 23 employees and $2M+ in annual revenue, and ran for three years. His clients ran the gamut: Silicon Valley founders, Grammy-winning musicians, Olympic athletes, New York Times bestselling authors. None of whom he's allowed to name.
In 2021, Cole pivoted again. He co-founded Ship 30 for 30 with Dickie Bush - a 30-day writing challenge turned full-scale writing education program. It became the fastest-growing cohort-based writing course on the internet, eventually training 10,000+ students. He also co-created Category Pirates, a paid newsletter and category design consultancy with Eddie Yoon and Christopher Lochhead that published books hitting #1 on Amazon simultaneously. Then, in 2023, he launched Premium Ghostwriting Academy. It hit seven figures in under 90 days.
The portfolio now generates over $5 million annually. There's Ship 30 for 30. Premium Ghostwriting Academy. Write With AI (a weekly newsletter on AI-assisted writing). Typeshare (a SaaS platform for digital writers). Different Publishing (an audio-first publishing house). And "Coffee with Cole," a video podcast. Plus his personal Substack, "The Art & Business of Writing."
Cole's core thesis has never changed: the internet is the greatest writing teacher ever built, because it gives you real-time data on whether your writing connects. The platform changes. The fundamentals don't. Write with specificity. Answer a question the reader is already asking. Make it about them, not you. Ship daily. Let volume do its compounding.
