I have been writing online since I was 17 years old.
In 2007, I started a gaming blog about my experiences being one of the highest-ranked World of Warcraft players in North America. That gaming blog ended up becoming one of the most-read WoW blogs on the Internet, with over 10,000 gamers reading my writing on a daily basis. This was the very beginning of the multibillion-dollar eSports industry we know today.
In 2008, I attended one of the top journalism schools in the country, the University of Missouri, for my freshman year of college. There, my professor addressed our lecture hall of 500 students with a powerful statement: "The world of blogging is a trend and will never be a credible source of writing." As an already established blogger, and a firm believer in the future of the Internet, I immediately lost faith in journalism as a career and spent that entire first year of college skipping class and practicing my own creative writing.
In 2009, I quit playing World of Warcraft, stopped blogging, failed most of my classes, and was put on academic probation. Clearly struggling, my parents insisted I take a semester off college to attend an Outward Bound program for teens with substance abuse issues. That was a life-changing experience for me. We canoed 320 miles through Florida into the Gulf of Mexico, completely detached from all technology and outside communication with the world for 30 days. And when I came back, I made a commitment to put myself on a better path, and do whatever I had to do to bring my creative pursuits to life. I transferred from the University of Missouri to Columbia College Chicago at the end of the year.
From 2009 to 2012, I went 100% sober, picked up bodybuilding as a hobby, and studied Fiction Writing at Columbia College Chicago. I decided to pursue my dream of becoming a successful writer & author. So I took classes on storytelling techniques, journaling, Coming of Age stories, Russian and American literature, and spent the summer of my junior year studying Magical Realism and Italian literature in Prague and Florence. I also started working on my first book.
In 2013, I graduated from Columbia College Chicago with a degree in Fiction Writing, and got a job as an entry-level copywriter at a boutique advertising agency downtown Chicago. This was my introduction to the “business” side of writing & creativity. My boss, the Creative Director, quickly became a close mentor and important influence in my life.
In 2014, in an attempt to keep my dream of becoming a successful writer alive, I began writing on a platform called Quora—and challenged myself to write 1 Quora answer per day, every day, for a year. Worst-case scenario, I thought, I’d spend a year practicing my craft. Best-case scenario, this daily habit would spark my professional writing career—which is exactly what happened. In less than 3 months, I had my first answer go viral landing on the front page of Reddit. That answer has since accumulated over 1.1M views. And a month later, I had my first Quora answer republished by a major publication, Inc Magazine.
In 2015, I was the #1 most-read writer on all of Quora (out of 200 million+ users) with tens of millions of views on my writing, along with dozens of Quora answers republished in major publications such as TIME, Forbes, Fortune, The Huffington Post, Business Insider, Entrepreneur, Observer, Slate, Apple News, and more. I also launched my first digital product—an eBook series called Skinny to Shredded, sharing the workout routines and nutrition plans that had helped me change my physique and put on 70 pounds of muscle. This eBook series was how I made my first $5,000 online.
In 2016, I began preparing to quit my 9-5 job to go all-in on being a professional writer. Early in the year, so much of my Quora content had been republished by Inc Magazine that I was given a daily column. I quickly became one of their most-read columnists bringing in millions of page views for the publication and successfully earning 50% of my full-time salary writing a column per day (getting paid a penny per page view). By September, I felt confident I could quit my job and supplement the other half of my income through writing. And on my last day of work, I self-published my first book: a memoir called Confessions of a Teenage Gamer, about growing up undiagnosed with Celiac Disease and at the same time becoming a pro World of Warcraft player.
By 2017, just a few months after leaving my full-time job, I had fallen headfirst into the world of ghostwriting. My first client was a 60-year-old entrepreneur with a family business he had recently sold for over a billion dollars. He found me on Quora and asked if I could help him write similar pieces online sharing his lessons learned building his company. “You’ll be my ghostwriter,” he said. One client led to two, two to four, until eventually I decided to start a ghostwriting agency with one of my closest friends, working exclusively with founders & CEOs and helping them publish Thought Leadership content online. We called it Digital Press.
2018 - 2020, we scaled Digital Press to 23 full-time employees, 80+ concurrent clients all over the world, and over $2,000,000 in annual revenue. Our clients ranged from multibillion-dollar enterprise software companies to Grammy-winning musicians, Olympic athletes, unicorn Silicon Valley startups, and New York Times best-selling authors. It was a wild journey and incredible learning experience. But after 3 years of running the business, my personal writing had suffered—so we decided to scale the business back to just the two of us, being more selective with clients and prioritizing work-life balance. (Which ended up being a very lucky decision, because COVID hit a few months later and would have destroyed our company.) With more time to write again, I published my 2nd book called, The Art & Business of Online Writing.
In 2021, after some time to recharge, I started 3 new businesses: Ship 30 for 30, a cohort-based writing program with Dickie Bush; Typeshare, a SaaS platform for digital writers with Sam Shore and Dickie; and Category Pirates, a paid newsletter & category design consultancy with Eddie Yoon & Christopher Lochhead. We also published two books: The Category Design Toolkit&A Marketer’s Guide To Category Design.
In 2022, we scaled these businesses to 6, 7, and multiple 7 figures in revenue. Ship 30 for 30 became the fastest-growing cohort-based writing program on the Internet generating millions of dollars in revenue. Category Pirates became a Top 5 paid business newsletter on Substack, and our consultancy generated millions of dollars in category design project fees. And Typeshare grew to hundreds of thousands of dollars in recurring revenue. My online audience also skyrocketed, accumulating over 300,000 followers across X (Twitter), LinkedIn, Quora, Medium, and Instagram. We also published our third Category Pirates book, Snow Leopard.
In 2023, I exited Category Pirates as a business. Dickie and I doubled-down on Ship 30 for 30, built a production studio in Miami called The Shipyard, started a Build-In-Public podcast called The Espresso Hour, and launched 2 new business verticals: Premium Ghostwriting Academy, a hands-on training program for ghostwriters; and Write With AI, a paid newsletter sharing ChatGPT & Claude prompts for digital writers. In its first year, PGA grew to over $3,000,000 in revenue (eclipsing Ship 30 for 30), and Write With AI grew to over $100,000 in annual recurring revenue. I also published my next book in the Art & Biz series: The Art & Business of Ghostwriting.
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