How I got into ghostwriting, ended up writing for hundreds of Startup Founders, Fortune 500 execs, and a handful of Olympic athletes, Grammy-nominated/winning musicians, NYT best-selling authors, and more.

A thread

1/ Ages 23-26, I worked as a copywriter for an ad agency in Chicago. Some of my time was spent creatively. Most of my time was spent proofreading 20-80 page proposals and ghostwriting emails for my boss/mentor. He would pace around the office dictating and I would type.

2/ During those years, I became the #1 most-read writer on Quora with tens of millions of views. Every day, I would learn something new at work, and at 5/6pm I'd walk to the Starbucks down the street and answer a Question on Quora based on what I'd just learned.

3/ What made my Quora answers different were my stories. Almost every Answer I wrote, in some way, told a story of a moment in the past where I'd also learned the thing I was explaining: through playing World of Warcraft, through bodybuilding, etc.

4/ In 2015, after having dozens of my Quora answers be republished by @Inc , they gave me my own column. In my first 30 days writing for them, I wrote 30 columns, drove hundreds of thousands of page views, and became one of their most-read columnists.

5/ By the time I was 26, I had successfully (almost) replaced my full-time income with the money I was earning writing for Inc. I got paid per page view, and since I had so many articles go viral, I was earning $3,000/mo on average. I decided it was time to quit my job.

6/ I was living in a studio apt in Chicago. Ceiling was falling apart. No A/C. Heater from the 1940s. Didn't own a TV. Or a couch. Or internet. Since graduating college, I told myself no internet until I finished writing my first book, Confessions of a Teenage Gamer.

7/ My last day of work was the same day I published my book. When people asked me what I was going to do next, all I said was, "I'm going to be a freelance writer." My only goal was to cover the rest of my overhead expenses and keep pursuing my dream of being an author.

8/ In an effort to get clients, I started writing on Quora and Inc about how I "helped other people with their writing too." I didn't even know what that looked like yet, I just wanted people to know I was "open for business." A few days later, a guy sent me an email.

9/ He had spent 20 years building a business that he eventually exited for tens of millions of dollars. That business went on to be acquired by one of the biggest retail chains in America for billions. He wanted to tell his story online and liked my conversational writing style.

10/ Because he was now working in Private Equity, he didn't have very much time. Our calls would be 15 minutes long, and I'd furiously type notes as he dictated insights he wanted to share to me over the phone, transcribing in real-time. All those emails at work had paid off.

11/ The first article I sent him was so "in his voice" he could hardly believe it. The secret? I worked almost exclusively from the words and phrases he gave me, just structured in the "viral style" I'd developed for myself. He immediately recommended me 2 more clients.

12/ Within 30 days, I went from making very little money as a copywriter to making more than $10k in a single month, just ghostwriting articles. 30 days later, $15k. By Christmas, I was making $20k/mo working ~3 hours a day working exclusively with founders & executives.

13/ I flew to Atlanta to tell one of my closest friends what was going on. For months, I'd been telling him to "take the leap" with me. After seeing the he finally agreed. We would take my ghostwriting approach and turn it into a business. We called it Digital Press.

14/ Step 1 was optimizing the process I'd been using manually: phone calls & writing. He took on the phone calls, allowing me more time to write, and we started using a 3rd party ( @Rev) to automatically transcribe calls. This made my life 10x easier. Now we could scale.

15/ Within 3 weeks, we went from us sitting on my co-founder's apartment couch with a business idea to a company doing 6 figures in sales. For the first 2-3 months, I was ghostwriting 5+ articles per day, every day, 7 days a week. I was barely sleeping. We needed to hire people.

16/ We started with 1 writer to help me out. Then a salesperson to help us keep clients coming in. Then an account manager to replace my co-founder on the calls so he could spend more time selling. Then another writer. Etc. Another 3 months later and we were at $500k/ARR.

17/ By the 10th month marker, we were in full gear (this was also around the crypto boom of 2019). We had blown past the $1M revenue milestone, were at 12 full-time employees, and were onboarding 5-10 new clients a month. Our client roster was STACKED with industry leaders.

18/ All of a sudden, our business had gone from "an idea" to a publishing house working exclusively with some very, very big names in a wide variety of industries. I was spending 10+ hrs per day workshopping and editing pieces internally, trying to uphold quality.

19/ By the end of 2018, our team had ballooned to 20 full-time employees and 60 clients, doing multiple millions in revenue. It was one of the most exhilerating things I'd ever done. I had also ended up in the hospital with shingles and was completely burned out.

20/ We ran Digital Press like this for 2 1/2 years. Eventually, we realized that ghostwriting the way we were approaching it was not scalable. It's a highly subjective art, and best serviced with a high level of individual attention.

21/ By the end, I'd written and/or edited for more than 300 different founders, executives, Silicon Valley investors, international speakers, movie stars, you name it. We scaled the business back, and now Digital Press works with a small handful of clients at a time.

22/ Now, after having written several thousand articles on the internet, I am moving more into ghostwriting/co-authoring books & strategic company messaging. Through Digital Press, my co-founder and I still ghostwrite articles and Twitter threads like this one :)

23/ For more writing career stories & advice, check out my Monday newsletter: https://howiwrotethis.substack.com/