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Perennial Seller Summary – Ryan Holiday

Arthur Worsley
by Arthur Worsley
M.A. Psychology, Oxford. McKinsey Alum. Founder & Editor at TAoL.

Perennial Seller, Ryan Holiday

“Perennial Seller”, Ryan Holiday
Print length: 257 pages. Buy on Amazon.

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Perfect for you if:

  • You’re a creator – be it writer, film maker, musician, artist or entrepreneur.
  • Many of the things you love, read, listen to, watch or use are over 10 years old.
  • You want to understand why some creations become timeless sellers.

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perennial | adjective lasting or existing for a long or apparently infinite time; enduring or continually recurring.

Ryan Holiday’s “Perennial Seller” is a book for creators that explains how to build for timeless and enduring impact. It serves as a refreshing reminder of long term value in an age where many industries (and governments) seem so fixedly short-termist. True to its title, the book favours time-tested, practical and inspiring home truths over get-rich-quick hacks.

I learned a huge amount from reading it and am looking forward to applying its principles in my own writing. I will certainly be re-reading it and these notes again in the future.

The book divides into two main parts. In Part I: “Making a Perennial Seller”, Ryan describes what it takes to create in a way that withstands the tests of time. In Part II: “Marketing a Perennial Seller”, Ryan explains both how to ensure your message is heard and also why it is important be personally at the centre of the marketing process.

Ryan’s own extensive reading and network is evident in the number of powerful examples and quotes throughout the book. These help to add an enduring sense of depth and credibility to his arguments.

If you love reading and/or don’t know of Ryan’s work I strongly recommend a visit to his blog and signing up for his excellent monthly reading list. I’ll be crunching many of the books that appear on it in the coming months.

“Perennial Seller” is available on Amazon in both kindle and paperback editions.

[title text=”Part I – Making a Perennial Seller” style=”center”]

Start with the right attitude.

There is no magic to creating perennial sellers,

  • Masterpieces are made layer by layer, piece by piece …
  • … and ‘genius is 1% inspiration and 99% perspiration’.

But creating a perennial seller must be your aim from the start,

  • Aim for lasting (> 10 years) impact and relevance.
  • Harden yourself to short-term measures of success.

And you must prepare to meet the demands of delivering massive value.

  • Laser-like dedication (and by extension sacrifice),
  • Persistence (fuelled by a clear personal motive), and
  • Dogged end-to-end personal responsibility (from making to marketing)

Develop specific positioning.

One sentence, one paragraph, one page
This is a [ What ] for [ Who ] that helps them by [ How ]

Create something defined and accessible… [ What ]

  • Know your genre conventions and audience expectations.
  • Be bold and experiment with breaking its conventions.
  • But not too many at once, it must stay accessible.

… that addresses a specific core audience… [ Who ]

  • Picture creating for just one specific person.
  • Create for your core audience only, crossover is a bonus.

… and solves a significant and enduring problem. [ How ]

  • If the problem is not significant, why should people care?
  • If the problem is not relevant in 10 years, nor is the solution.

Create, evolve and refine until perfect.

Concept > Prototype > Draft(s) > Refined creation

Start small – testing early and often.

  • Grow from e.g., concept to conversation to article to talk to book.
  • Test for external resonance and feedback at each stage.
  • Change and pivot early in response to feedback.

Next, write the first draft.

  • Consider a pre-rest/drawdown period to prepare physically and mentally.
  • Then create intensively and with your audience of one always in mind.
  • Make time and space to focus on nothing else during this period (see Deep Work).

Now, prepare for extensive rewriting, editing and refinement.

  • Understand that this process is usually as long or longer than the writing.
  • Seek feedback externally – from editors and audience members you trust.
  • Be open to feedback, even if it’s major – many classics are total rewrites of their first draft.
  • Keep iterating, even after release – many classics only peaked in later editions.
  • Keep the positioning specific (even if it needs updating) and stay resolute to your aim of longevity.
[title text=”Part II – Marketing a Perennial Seller” style=”center”]

Word of mouth sustains life, marketing creates it.

The Lindy effect: The chance of something disappearing decreases the longer it exists.

Word of mouth is the self-sustaining heartbeat of a perennial seller.

  • It passively refreshes discoverability in the absence of active marketing.
  • It converts better (50x so for trusted and emphatic vs. low quality word of mouth).
  • It feeds on and multiplies itself.

To qualify you must first deliver massive value (see Part I).

But even then, you must make yourself heard.

  • There is more competition for our limited attention than ever before.
  • A creation must stay above this noise or disappear into it – no matter how good it is.
  • Marketing brings a creation momentarily to the surface and gives it a chance at life.

You must take personal responsibility for driving discoverability and building a platform.

Many shy away from marketing.

  • To distance themselves from judgement/failure.
  • Because they prefer creating.
  • Out of purist sensibilities.

But you cannot outsource it, nor should you want to.

  • Nobody cares about your creation as much as you do.
  • Nobody understands the positioning as well as you do.
  • Giving up control means leaving everything you’ve worked for to chance.

Your job is to tell people what your creation is and why they should care.

  • Marketing is anything that gets and keeps customers.
  • Its goals are to drive short term discoverability and build a long-term platform.

Driving discoverability is a sprint: it is creation specific and has diminishing returns.

Concentrate on a launch day.

  • Bring relationships, media contacts, past experience, favours, budget and allies to bear.
  • Choose a date with a hook (e.g., international XYZ day).
  • Use this spike to puncture through the noise.

Give things away for free.

  • Sacrifice short-term profit for discoverability (often cheaper than you think).
  • Create a core following by giving away the first X units for free (e.g., as samples or to influencers).
  • Give part of your service away for free to drive sales in others (e.g., free TED videos vs. $10k USD conference tickets).

Use discount pricing.

  • Price for accessibility and discoverability – don’t let ego stand in the way of impact.
  • Use occasional short-term price drops to drive sales. Often has a prolonged impact.

Find your champions.

  • Find, engage and prefer organic, existing users of your creations over paid influencers.
  • Consider non-traditional influencers (e.g., business figures or politicians over celebrities).
  • Offer don’t ask: help them, send free things (enough to give away to their friends).

Be wary of traditional media.

  • Can be useful as part of a larger campaign by building a profile and credibility.
  • But rarely gives a good direct return on high cost of time and money.

If you still want it: Start with smaller, niche outlets.

  • They appeal directly to your target market (remember Positioning).
  • These are cheaper and easier to access than major publications …
  • … and also create momentum by feeding into them anyway (like tributaries into a river).

Even then: Don’t pay for attention. Earn it. Try:

  • News-jacking. Adapt quickly to and piggy back on ‘hotter’ trends (e.g., accepting bitcoin payments).
  • Creative advertising. Attention grabbing but risky for big corporates and so often overlooked and under-competed for.
  • Publicity stunts. Give reporters something to write about. Be bold (but not too bold).
  • Being direct. Google reporter contact details. Call them. Make it interesting by being interested.

For everything else (e.g., social media) adapt, test widely and double down on results.

  • Adapt to the channels available at the time (this changes rapidly).
  • Adapt to the features and popularity of those channels (changes even more rapidly).
  • Try a bit of everything. See what sticks. Double down on it.

Building a platform is a marathon: it benefits all your creations and is compounding.

A platform is all the tools, relationships, access and audience you have to spread creative work.

Building a direct (e)mailing list by providing massive value.

  • Give something free – an ebook, a sample, a service (e.g., book recommendations).
  • Run competitions and sweepstakes – make the free offer time-limited.
  • Do things by hand – create a physical form you can hand out at events.
  • Do a swap – Cross promote with another creator’s list.
  • Make it easy – Use pop-ups and simple sign up forms, put a link in your email signature.
  • Ask your existing contacts to join – export your social network followers, ask family and friends.

Build a karma positive network (contacts, relationships, influencers and fans).

  • Never dismiss anyone – rule #1 is just be a nice person.
  • Play the long game – all senior decision makers were once fresh faced minions.
  • Focus on pre-VIPs – engage people who should be famous, even if they’re not yet.
  • Participate – honestly and authentically with your network and fans (see rule #1).
  • Be a giver – give long before you think of receiving. Always stay karma positive (See Give and Take).

Build a body of work.

  • Good work compounds itself – the more value you deliver, the wider your platform will grow.
  • Which is why making is also marketing – building a platform is part of building a career as a creator.

Reach out to new fans.

  • Collaborate with other creators to make something new that promotes crossover.
  • Create variations on your portfolio that expand as well as serve your current audience.

Build an empire. Ask yourself:

  • What new areas would my expertise be valuable in?
  • Can I cut out the middleman and invest myself?
  • Can I help other creatives achieve what I have?
  • What are people in my field afraid of/looking down on?
  • How can I diversify my income stream?
  • What would I do if I took a break from creating?
  • What components around my work can I improve or grow?
    (e.g., live events, conferences, subscriptions, memberships)
[title text=”Related Reading / Watching / Listening” style=”center”]

“How Great Leaders Inspire Action”, Simon Sinek: The structure of this 20 minute TED talk bears striking similarities to Ryan’s book. It was also the inspiration for the title of this blog.

“How I Built This” , NPR: Is a podcast about innovators, entrepreneurs, and idealists, and the stories behind the movements they built. A fascinating insight into the stories of some of today’s Perennial Sellers.

“Give and Take: A Revolutionary Approach to Success”, Adam Grant: This wonderful perennial seller is a fascinating insight into the network building power of becoming a giver rather than a taker.

“Shoe Dog: A Memoir by the Creator of NIKE”, Phil Knight: A fascinating and candid memoir from one of the 20th Century’s greatest entrepreneurs and perennial creators.

“Steve Jobs: The Exclusive Biography”, Walter Isaacson: As above.

“Elon Musk: How the Billionaire CEO of SpaceX and Tesla is Shaping our Future”, Ashlee Vance: And again. See also this excellent series of posts from Wait but Why.


Perennial Seller Quotes

These Perennial Seller quotes come from TANQThe Art of Living‘s growing central library of thoughts, anecdotes, notes, and inspirational quotes.

“A book should be an article before it’s a book, and a dinner conversation before it’s an article. See how things go before going all in.”

— Ryan Holiday, Perennial Seller

“You don’t have to be a genius to make genius – you just have to have small moments of brilliance and edit out the boring stuff.”

— Ryan Holiday, Perennial Seller

“The best way I’ve found to avoid missing your target – any target – entirely is to identify a proxy from the outset, someone who represents your ideal audience, who you then think about constantly throughout the creative process.”

— Ryan Holiday, Perennial Seller

“The key to success in non-fiction work [is] that the work should either be ‘very entertaining’ or ‘extremely practical'”

— Ryan Holiday, Perennial Seller

“The higher and more exciting standard for every project should force you to ask questions like this:
– What sacred cows am I slaying?
– What dominant institutions am I displacing?
– What groups am I disrupting?
– What people am I pissing off?”

— Ryan Holiday, Perennial Seller

“People want things that are really passionate. Often the best version is not for everybody. The best art divides the audience.”

— Ryan Holiday, Perennial Seller

“Write out exactly what your project is supposed to be and to do in …
One sentence.
One paragraph.
One page.
This is a ___ that does ___. This helps people ___.”

— Ryan Holiday, Perennial Seller

“When it comes to attracting an audience, the creators who take the time to get their positioning and packaging right – who don’t just go with their first instinct and hope – are the ones who will win.”

— Ryan Holiday, Perennial Seller

“Nothing has sunk more creators and caused more unhappiness than this: our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.”

— Ryan Holiday, Perennial Seller

“Luck is polarising. The successful like to pretend it does not exist. The unsuccessful or the jaded pretend that it is everything. Both explanations are wrong.”

— Ryan Holiday, Perennial Seller

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