Hi, I’m Billy Oppenheimer.
In June 2018, I cold emailed my favorite writer. I thanked him for his work then offered to work for him for free. 6 months later, I was hired full time as a research and writing assistant. Since then, I’ve helped and observed Ryan Holiday research, write, edit, publish, and market 5 books, grow his email lists by 500,000+ subscribers, and publish an article a week read by who knows how many people.
Before that cold email, I worked odd jobs and lived across the east and west coasts of Australia, the South Island of New Zealand, and the west coast of the U.S. I was home in Philadelphia—in between ski seasons in Queenstown and Colorado—for Thanksgiving in 2017. My Uncle Bill, a writer aware of my developing interest in the craft, recommended I read Perennial Seller: The Art of Making and Marketing Work that Lasts.
I read Perennial Seller on my flight back to Colorado. As the plane taxied, I texted my brother my gate number and then googled “Ryan Holiday.” Search results showed someone about my age, maybe a little older. I googled “Ryan Holiday Perennial Seller.” Someone about my age, maybe a little older, wrote this…and six other books. I ordered The Obstacle is the Way, Ego is the Enemy, Trust Me, I’m Lying, and The Daily Stoic.
After reading just about everything he published, I emailed Ryan on June 12, 2018. “Just some words of thanks and admiration” was the subject line. That is what it was, but I also told him if there was ever an opportunity to work for him, I’d do it for free. The best way to learn a craft, I read in one of his articles, is to “go straight to the seat of intelligence.”
Ryan responded a night later. He could use help on a project. A few weeks later, there was another project. A couple weeks after that, another.
On August 28, 2018, I was walking out of my apartment to go for a run and opened Strava, the activity sharing app for runners and cyclists. It wasn’t unusual that the most recent post in my following feed was Ryan. What was unusual was that the map showed he had recently run in Vail. I could see Vail from where I stood. I emailed Ryan asking if he was in town for long and said it’d be awesome to meet him in person. He was on the first flight out the next morning after a talk to a room packed with selected founders of budding businesses, but if I came to his talk, there might be a few minutes before or after.
There were a few minutes after the talk and after hundreds and hundreds of entrepreneurs bided their time to get a second of his. He peeled away and motioned for me to follow. He asked me a couple questions. We walked up a flight of stairs. I asked him a question. We walked outside. He recommended a book. Then a valet pulled up with his rental. He got in the driver’s seat but before he closed the door, he said he and his business partner were talking about hiring someone full time. He asked if I had any interest. It didn’t occur to me to ask what the role was or what the work would entail or what the pay would be. Definitely, was all I said.
I got in my car and stopped short of turning the key to call Uncle Bill. “Remember that book you told me to read last Thanksgiving?”
“Of course, I got Ryan’s reading list email last Sunday,” he said. “What’d you think?”
I picked up the story from there. When I finished, there was silence for two or maybe ten seconds. “I have goosebumps,” Uncle Bill said. “I do too,” I said.
I still get them—when Ryan calls or emails or says good morning as I hit the last stair on my way to my desk in the office across from his.
If you want to read about what I’ve learned from him so far, you can do so here.
If you want to get an email from every Sunday at 6 AM (CT), you can sign up for my newsletter.
If you want to email me, you can email me.