Perennial Seller by Ryan Holiday

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Perennial Seller Summary

Creating work that stands the test of time requires focusing on quality, not trends, and prioritizing long-term impact over short-term success. Successful creators understand that building a perennial seller involves relentless refinement, thoughtful marketing, and strategic positioning to ensure their work resonates deeply and continuously with an audience. By committing to the craft and leveraging patience, consistency, and a focus on serving the audience’s needs, creators can produce work that endures across generations.

Perennial Seller Notes

These are my notes from Perennial Seller by Ryan Holiday. Each one contains a core idea from the book that stood out. The goal of writing my notes this way is that each could be it's own independent idea with the need for the specific context within the book.

Tim Ferriss's Networking Strategy

Never dismiss anyone: Someone might be able to help you one day. Remember them and leave a lasting impact on them.

Play the long game: You have to establish a relationship before you can get any help from that person. The relationship should be beneficial to both people—so find out how.

Focus on "pre-VIPs": People who aren’t known will be. Anyone who is brilliant and hardworking will eventually find success.

Filtering the Right Feedback

Neil Gaiman, an English writer, once said: "When people tell you something's wrong or doesn’t work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong." To collaborate effectively, you need to know what inputs you should be taking in. Someone from the outside doesn’t have the proper context or information to know what the best way to fix something is. Only you know how to fix it because you know what the goals and objectives are.

The Drawdown Period

John Boyd used what he called the "drawdown period" to mark the start of his convergence process. It’s a period of stillness and raw silence. After a breakthrough, John would spend weeks with the idea. Looking at it. Testing it. Exploring it from all angles. Once all possible problems were identified and the idea felt right from all the pre-work, he would begin working on the project. Ryan Holiday did this for one of his books. Setting a January 1st start date, he gave himself a two-month drawdown period. No reading or researching. Just thinking, processing, and digesting. Resting and preparing for the push. This provides time for us to clear up mental bandwidth to start creating, making decisions, and focus. Eventually, Ryan’s subconscious pushed him to begin, letting him know on December 19th he was ready.

Mania Always Leads to Crash

New industries create speculation. The ideas seem irresistible and urgent. The time to cement yourself in the marketplace has to be right now. However, ambition and urgent timelines create instantaneity. Mania makes others lose their sense of rationale and long-term thinking. Peter Thiel says industries growing like weeds are exactly what you want to avoid. The speculative gold rush creates too much competition. The hype creates too much noise to realize the long-term potential of any idea. Peter says, "If you focus on near-term growth above everything else, you miss the most important question you should be asking: will this business still be around a decade from now?" All mania turns into panic at the first obstacle and panic leads to a crash.

Toyota Way

Great things are timeless. When we develop great principles, they can guide us for the rest of time. For decades, there have been two essential principles that guided Toyota’s internal philosophies. The first one is to always praise long-term virtues. Decisions must always be made with the long-term impacts in mind. The second is to hold deep respect for processes. Having systems and processes are important for sustainability. These two principles led to the creation of the Corolla and the Camry. They’re principles everyone at the company lives by.

Trading Up the Chain

Ryan Holiday has a process for marketing he calls "trading up the chain." Today, all of media has become interconnected. People pick up and re-report others' content in an attempt to arbitrage the information. After writing The Obstacle Is the Way, Ryan started to receive emails from coaches saying that his book helped them win. He sent hundreds of copies to sports teams in an attempt for the book to catch on in sports and get featured in Sports Illustrated or ESPN for marketing. His friend asked if he eventually wanted to be a guest on her small sports podcast. This gave him a chance to tell his story on his own terms. The podcast led to niche sites covering the story and showing it to the right people. Eventually, he reached the top of the chain by giving others a story to tell, and Sports Illustrated published an article, "How a Book on Stoicism Became Wildly Popular at Every Level of the NFL" — selling out of books.

The Car Test: Testing Our Work

You need to have the discipline to hit pause and understand if your work meets the standards we set for ourselves and consumers. We need to have tests for our work to pass. Max Martin subjects every finished song to what he calls "the LA Car Test." In it, he blares the song as he drives the PCH to see how it sounds, feels, and if it enhances the experience he's having. When working on Watch the Throne, he recounted his time working with Kanye West. As they sat down to co-produce a song, Kanye said: "I'm bringing Mary-Kate and Ashley Olsen over because they're like my thermometer for what white girls listen to, I guess." You need to have ways to beta test your work with others to get to the best possible result. The test will be different depending on the product, but they're critical to get feedback so you can tweak the product as a whole.

False Positive Creative Ideas

Creative people regularly receive "false positives" around their ideas. They'll have an idea they believe is good, but really it's mediocre. After peeling back the layers of the idea they find the seed that exists for a better idea to pivot to. The movie Up was originally a story about two princes who lived in a floating city on an alien planet. Once the writers really dug into the idea, they realized the underlying theme was aimed at escape and pivoted the script towards what exists today. The first write answer is almost always a false positive. It plants the seed of opportunity for a bright idea to grow from with a little extra thought and validation.

Negative Capability

Ideas go through a process of natural selection to evolve with time. As we diverge in our creative process, disconnected ideas collide. Poet John Keats deemed negative capability a critical part of the creative process. The quality of our creative outputs is determined by our ability to hold multiple contradictory ideas in our head. As we diverge and our mind swirls with ideas, we have to build up the patience to tolerate this step in the process. Negative capability allows us to refine our ideas to get to the best final solution — rather than the first right answer.

Infinite Shelf Space

Production costs have plummeted in recent years—it's never been easier to start something. If you want a chance at grabbing people’s attention, your project must appear as good, or better, than the alternatives that exist. The internet has created infinite shelf space for products to exist. This removes availability bias in the decisions of what we consume with our time. It means we have a split second to make an impression and hook someone’s attention. The same content with different tweaks can perform 10x better from one small change that keeps you from being ignored.

Pre-Work Matters

We’re obsessed with action and getting to something tangible as quick as possible. It’s a common misconception that “pre-work” is just mental masturbation. Pre-work matters so much more than the emphasis we put on it. The conceptualization of the idea. The development of our motivation. The understanding of where the product fits in the market. The plan for execution. All of these are intangible factors that cause us to take on debt when they are ignored. It’s much harder to bolt them on to the project later. The pre-work is the foundation essential to scale an idea effectively. It’s the part of the creative process people rush rather than spending the time it demands. Doing the pre-work makes the rest an effortless process.

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I've used some of these ideas from my notes in many other writings. If the topics resonated with you these articles go more in-depth.

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