Sex and Cash Week, Part III: The Moonlighter
This week, we’re looking at different applications of the Sex & Cash Theory. Click here to read part 2 of the series, The Grinder.
You may not yet be familiar with Ryan Holiday or Stocism, but Bill Belichick, Arnold Schwarzeneggar, and LL Cool J are. Only 29 years old, Holiday’s career is already a fascinating case study in leveraging one opportunity to the next and his work (as you can see from the sampling of names above) obviously resonates with some very powerful people. After dropping out of college, Holiday shadowed some of the biggest names in recent non-fiction literature, became the Director of Marketing at American Apparel, gained a notorious reputation for provocative advertising and media hijinks, and now runs his own marketing agency and just released his fourth published book. That’s a lot to achieve in less than a decade — so how did he do it?
The Ryan Holiday whose musings you read today about overcoming life’s obstacles and defeating our corrosive egos seems much different than the one you’d expect to meet in 2012, when he would lie, cheat, and steal to get media exposure and notoriety for the clients and companies he represented. Back then, only in his early-20s, Holiday was on the fast track to corporate success. Lurking underneath this facade, however, was a budding author and modern day philosopher who felt a growing divide between his work and what he wanted from life.
If you were only interested in the “Cash” aspect of your career, Ryan’s career path is a pretty damn good example to emulate. After dropping out of college to work at a small Los Angeles talent agency, he used the Canvas Strategy to great effect, parlaying his experience and making new, powerful connections at every turn. From the talent agency, he met Tucker Max and helped promote I Hope They Serve Beer in Hell and turned that experience into his marketing role at American Apparel, where he worked for six years.
Even while he was killing it for his day job, he kept pushing himself into new territory. In 2009, he signed on with Robert Greene and 50 Cent as a research assistant on their book, The 50th Law. In 2012, he launched his own marketing and consulting company and turned his methods and war stories from the PR world into his first book, Trust Me I’m Lying: Confessions of a Media Manipulator, which made the Wall Street Journal Best Seller list. The young marketing star had blossomed into a moonlight author.
Ryan continued blogging and churning out books while he was still collecting checks from American Apparel. He parlayed more of his marketing experience into his second book, Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising. As he went through the ups and downs of his career and the tumultuous times at work, he turned his personal interest in stoicism into his most renowned book, The Obstacle is the Way, which became a cult classic in the professional sports world and was given to each of the Patriot players by coach Bill Belichick during their Super Bowl run in 2014.
Amidst leadership chaos, Ryan left American Apparel in 2014 and turned full-time consulting through Brass Check and writing his books and other articles. He released his fourth book last month, Ego is the Enemy, another WSJ Bestseller, which persuades readers to focus on their work and not the perception of themselves through the lens of more historical anecdotes and stoic wisdom. Today, he lives the romantic daily life of a writer, but keeps his marketing agency running and happily exchanges his time and expertise to those willing to pay the consulting fees he demands.
Ryan Holiday has rapidly developed two distinct and valuable pillars on which to continue growing his career. His marketing and consulting services are hard-earned and valuable and command a handsome sum when he wants to bring in some cash and his writing career provides the life he loves and a natural outlet for distilling his experience, wisdom, and lessons learned from his voracious reading habit. Using the Moonlighting strategy, he brought his life plan to fruition before he even hit 30, the perfect balance of Sex and Cash.
