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How to turn information into a story

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Chapter 19 of 20 · Characters and Storytelling
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1. Finding Product-Market Fit
Test for real customer pull earlyPick a narrow niche to start inLaunch a simple first version fastLearn from users and customersRead early signs of product-market fit
2. Onboarding and Activation
Structure onboarding as a storyAsk and use onboarding questionsGet users to the aha moment fastDecide how long onboarding should beBuild quiz funnels for paid traffic
3. Paywalls and Pricing
When to choose a hard paywall over freemiumDesign a paywall that convertsPrice annual and monthly plansSet, raise and localize pricesRun free trials and free tastes
4. Business Models and Revenue
Structure subscription tiersKeep a free tier that pays offCharge for usage and AI creditsPair hardware with a subscriptionAdd ads, affiliates and partners
5. Retention and Engagement
Measure retention honestlyBuild habit loops that bring users backUse notifications and lifecycle messagesReduce churn and handle cancellationsBuild social loops and community
6. Brand and Positioning
Position against bigger incumbentsName and describe your productEarn trust in high-stakes categoriesBorrow credibility from celebrities and experts
7. Organic Content and Creators
Find, vet and recruit creatorsPay creators fairly and safelyBrief and manage creatorsFind and copy viral formatsScale one format across many accountsRank in AI search and SEO
8. Paid, App Store and Viral Growth
Make ads that convertTurn organic winners into paid adsStructure and scale Meta campaignsTell if paid acquisition is profitableWin in the App StoreBuild viral and referral loops
9. Experimentation and Analytics
Run trustworthy experimentsJudge test results correctlyRun more experiments fasterWhat metrics to track and how to define them
10. Building AI Products
Build for the models of tomorrowDesign AI interfaces beyond chatDesign AI agents people can trustMeasure AI quality with evalsControl AI costs and pricingBuild products with AI coding tools
11. Teams, Hiring and Funding
Hire people who thrive on ambiguityOrganize small product teamsRun exploratory bets and kill themWork as a team with AI agentsWhen to raise money or sell your company
12. Founder Principles
Pick a mission worth building a company aroundWhy to trust your own judgment over the consensusTurn failure and setbacks into the next stepLearn from rivals and copy what works
13. Choosing Where to Compete
Make low cost your competitive advantageCreate a market instead of fighting for shareWhy scarcity and brand can beat volumeBuild an advantage that feeds itselfAttack a bigger rival where it cannot followWhen to stay focused on the core business
14. Building and Leading the Company
Hire great people and give them roomAlign pay and ownership with the missionKeep your culture and standards as you growBuild candor and fast decision-makingWhy leaders must stay close to the work and customersChoose and prepare a successor
15. Capital and Deals
Fund growth without losing controlAcquire companies and keep what makes them workWhat to do with cash: reinvest, buy back or holdWhy to keep a cash cushion and avoid heavy debtStructure ownership to protect your missionNegotiate deals that keep your leverage
16. Finding Ideas and Thinking
How to find ideas worth writing aboutWhy writing is how you find out what you thinkHow to research so the writing carries feelingHow to read like a writer
17. Structure and Argument
How to open so readers keep goingHow to find the shape before you draftHow to keep readers curious with questions and cluesHow to argue without preachingHow to end so the last page lingers
18. Clear Sentences and Voice
How to write plainly for a reader who knows nothingHow to choose specific details over generic onesHow to sound like yourself on the pageHow to shape rhythm and phrases people remember
19. Characters and Storytelling
How to build characters readers care aboutWhat makes a scene move: want, obstacle and changeHow to write dialogue that sounds real but stays shortHow to make readers feel without telling themHow to turn information into a story
20. Revising, Habits and Readers
How to cut and rewrite your own draftHow to get feedback you can useHow to build a writing routine that lastsHow to get unstuck when a draft stallsHow to use AI without losing your voiceHow to write for one specific reader

1 The bottom line

Build the piece around one person with a struggle, a question and a five-second moment of change, and let facts arrive through them. Readers forget facts but remember people and the emotion attached to them.

2 Key takeaways

  • Build the piece around one person, not a topic or a group. Readers remember facts because of the emotion attached to them.
    • David Gelb38:06 did not explain how to make egg sushi. He showed an apprentice who needed 200 tries and wept when the master approved.
  • Find the person's struggle or central complication first. The struggle gives you a plot, a change and the person's hardest-won wisdom.
    • Wright Thompson14:19 built his Tiger Woods piece on Nike handing an extreme introvert a marketing plan made for the extrovert Michael Jordan.
  • Build everything toward one moment where the person changes. If you cannot name that moment, you do not yet have a story.
    • Shaan Puri27:21 says the ending should be the opposite of the opening, like Scrooge hating then loving Christmas.
  • Keep information in service of the story, and skim what the reader does not need to feel. Long explanation breaks the pull of the narrative.
    • Mitch Albom's36:03 mother praised his books for lacking long pages on how submarine widgets fit together.
  • Find the story first, then draw the lesson from it. A lesson hunted for a story feels forced.
    • Morgan Housel24:44 stood out at The Motley Fool by telling stories about finance among thousands of writers publishing numbers and charts.

if you can find somebody's struggle, you will find a plot.

Brandon Stanton, Humans of New York

2.1 Choose who the story is about

Pick one person the reader can follow, and let the facts come through them.

  • Tell the story of one person, not a group. Morgan Housel21:05 says readers can see themselves in one person.
    • When you write about groups, it becomes "them" and invites apathy.
    • His best hook is letting readers feel they are looking in a mirror, as with the Vanderbilts.
    • David Gelb38:06 planned Jiro Dreams of Sushi around how different chefs make sushi. Test shorts showed him the people were the interesting part.
    • Gelb38:06 says Chef's Table teaches almost nothing about cooking, yet it has lasted because it follows a character's journey.
  • Find a donkey to pull the reader through complicated material. Patrick Radden Keefe59:38 borrowed the idea from Lawrence Wright.
    • Ask who is going to pull the reader through all this material.
    • It need not be one character. The reader only has to feel they are following someone.
    • If no one else fits, be the donkey. Michael Pollan24:30 says finding the way to put himself in the story is finding the story.
    • Pollan bought steer 534 for 600 dollars. That changed how feedlot staff talked to him and gave him decisions to write about, like the 15 dollar hormone implant Pollan24:30.
  • Choose characters who speak vividly and play against type. Michael Pollan1:02:04 checks interview quotes for who sings and who is halting and boring.
    • He wants someone with real authority who says it in a vivid way.
    • Pollan likes people who break the stereotype, like a rancher who looks like a bookkeeper in a visor. He points to the little guys who beat the system in Michael Lewis's Moneyball and The Big Short.
  • Tell a big event through someone standing away from the action. Mitch Albom31:00 says pieces readers remember often sit away from the main action.
    • After the Kennedy assassination, columnists wrote grand sentences about America. Jimmy Breslin went to the man digging the grave.
    • At the Barcelona Olympics, Albom skipped the expected Carl Lewis story. He filed on a runner whose father carried him across the line after a torn hamstring Albom50:15.
    • The father had taught his son to run by putting the boy's feet on his own. Almost nobody in America knew the runner, yet the column became one of Albom's best known Albom50:15.

2.2 Find the struggle and the question

One struggle gives you plot, transformation and wisdom
Brandon Stanton looks for what a person overcame first, because everything else in the story grows from it.

A struggle or a conflict gives the reader something to wait on.

  • Look for what the person overcame before you decide how to tell it. Brandon Stanton20:07 says a struggle gives you three things at once.
    • It gives you a plot, because the person pushed against something.
    • It gives you transformation, because no one chews on a problem for years without changing. It gives you wisdom, because the struggle is what they have thought about most.
    • The most common long story hears is someone getting sober, because addiction is the thing people struggle with most.
  • Name the central complication of the person's life and how they handle it daily. Wright Thompson14:19 repeats Gary Smith's definition of a profile.
    • Show how they try to solve it day to day. Most of that happens inside them.
    • Keep the person as complex in their decisions as you are in yours.
  • Ask what the experts in a field fight about. Michael Pollan1:00:37 says that if there is no conflict, there is no tension.
    • opens A World Appears with a bet between neuroscientists Christof Koch and David Chalmers. The bet was over whether the neural correlates of consciousness would be found in 25 years.
    • A simple bet sets up tension that carries readers for 20 pages.
    • David Perell asked the same question of a beekeeping conference.
  • Dig for the origin story that explains why the person does what they do. David Gelb7:49 says the how is not enough. The why is the mystery of each episode.
    • He peels back layers to find the moments the subject got it wrong and what they learned.
    • Once the audience understands the motivation, the mannerisms and craft start to matter more. Spider-Man's origin explains the whole character: he lets a burglar go, then loses his uncle.

2.3 Build toward the moment of change

Every story builds to one five-second moment of change
If you can't name the turn, you don't have a story yet, and the middle is where the reader believes it.

Shape the story so it builds to one turn, and show what led to it.

  • Name the five-second moment of change. Shaan Puri27:21 takes this from Matthew Dicks' Storyworthy: everything builds to the one moment the character transforms.
    • Check the ending. It should be the opposite of the opening, as in every rom-com.
    • The turn usually comes after the character loses it all and is cornered into bravery Perell's roundup of Puri30:20. The player settles down. The workaholic lawyer opens a bakery.
    • In Puri's Batman example, the character is told the only way out of the cave is to jump without the rope, and he leaps.
  • Fill the middle with what triggered the turnaround and what you tried. Shaan Puri38:36 says most origin stories jump from "I got laid off" to "then everything was great."
    • Show what made you decide to change, the first thing you did, and the resistance you overcame.
    • Puri cites the Pixar idea that audiences love the hero for how hard they try, not for winning. An instant success is a weak story.
    • He told David his version had an arbitrary epiphany and fast-forwarded the montage.
  • Write the past as not yet decided. Dan Wang55:41 says every event feels impossible before it happens and obvious afterward.
    • Put the reader inside the uncertainty of the time.
    • Jimmy Soni59:59 cites David McCullough: put the reader in the perspective of people who did not know how history would turn out.
    • Franz Ferdinand's driver took a wrong turn toward the assassin, and nobody expected the Soviet collapse.
    • The Brooklyn Bridge looks inevitable now, but nobody then knew if it could be built. Soni59:59 stayed riveted by A Night to Remember even though everyone knows how the Titanic ends.
  • Look for the small human act inside the big story. David Grann1:16:56 says size is irrelevant and meaning is what counts.
    • He prefers telling big events from the bottom up, through ordinary people with their own desires and debts.
    • In The Wager, the captain and gunner shook hands before the captain was left on the island. Then they went back to hating each other.

2.4 Fit the information inside the story

Tell the slow parts fast, the fast parts slow
Mitch Albom's rule: skim the explanatory stretches and linger only where something specific happens.

Keep only the facts that move the person forward, and keep them out of the way.

  • Tell the slow parts fast and the fast parts slow. Mitch Albom36:03 learned this at the family dinner table.
    • His aunts got stuck on details like whether it was 1945 or 1946. His uncles told war stories that moved.
    • Skim the explanatory stretches and linger on the moments that matter.
  • Give each event a specific detail that earns its place. John Lennox's32:28 editor warned him that an episodic autobiography has length but no depth.
    • Keep an event only if something specific happened there that makes it interesting. Move the rest out.
    • Listing Veritas Forum talks in Austin on Tuesday and Denver on Wednesday is boring without particular moments.
  • Skim past research and tell it through your own experience. Paul Millerd55:10 did not spend three or four pages on the method and findings of the ideal-self and ought-to-self study.
    • He told it through his own experience of leaning on the ought-to self, then kept moving. He did not want to linger on the study.
    • The book has over 200 references, and the nerdy quotes alternate with personal reflection.
    • Ana Lorena Fabrega20:46 leaned on research by instinct. David pushed her to write stories from her classroom, because people remember stories, not facts and figures.
  • Anchor data in a concrete scene, and keep statistics out of the middle of a personal story. Peter Attia4:28 says even a book full of data needs a story to anchor the reader.
    • Attia opened Outlive with the first patient he saw die, a case of fast death, to contrast with the slow death medicine handles badly.
    • Rob Henderson55:38 followed Tara Westover's warning that dropping data into a personal narrative will break the spell. He kept the early chapters in story and put the research in a preface and the last few chapters.
    • Many readers skip prefaces, so Henderson's preface was a compromise to reassure readers there was a point. His editors wanted statistics in chapter one Henderson55:38.

2.5 Decide what it means and close

Choose the meaning of the story, state the lesson, and pull the reader on.

  • Find the story, then ask what broader lesson it carries. Morgan Housel24:44 says he has never started with a lesson and then hunted for a story to fit it.
    • His books follow this shape. Each chapter is a story, then the takeaway.
    • Ryan Holiday1:06:27 wants stories that are a theme, not an aberration, so he can stack similar ones to show an observable trend.
  • Decide what the facts mean, because the facts cannot change. Tucker Max43:51 says in a memoir you choose the story you tell about events you cannot alter.
    • His parents neglected him. He now tells it as hardship that also made him independent and a critical thinker.
    • It took years of therapy and writing to reach this version. It is sad and also inspiring.
  • End each short story with a lesson and a bridge to the next. Ali Abdaal34:30 loves The Psychology of Money for this.
    • Each chapter has an engaging story, a timeless lesson, and a final line that makes you want to turn the page.
    • The book has 20 chapters of about 1,500 to 2,500 words each. The story keeps you reading and the lesson gives the payoff.
  • Tell the reader, subtly, why the story is worth their time. Susan Orlean6:29 contrasts bullet points with saying "sit back and let me tell you this amazing story."
    • A story needs mood, characters and a subtle explanation of why it matters.
    • She imagines telling a dinner guest about the biggest library fire in American history, a topic they might not expect to care about.

2.6 Where writers disagree

Writers differ on how famous the subject should be, how much to bend the facts, and how faithful a portrait must be.

  • Familiar subjects versus unknown ones. Ryan Holiday1:06:27 likes stories about people the reader already has an opinion about, and finds very obscure subjects lack the power his lessons need.
    • Mitch Albom50:15 went the other way. His most remembered column was about a runner almost nobody in America knew, because the father and son theme was one everyone relates to.
    • Brandon Stanton20:07 builds whole stories on strangers, because their struggle supplies the plot.
  • How closely the story must match what happened. Yann Martel1:01:37 says you do not want lies, but facts only go so far.
    • Marc Andreessen36:51 would change the names, dates and events but keep everything that happened, so he can use 30 years of tech experience without writing a tell-all.
    • He has not written the book yet. He compares the idea to the show Ray Donovan, whose fixer cases reportedly all happened Andreessen36:51.
  • How faithful a portrait must be to its subject. Patrick Radden Keefe8:10 tells subjects the piece will look like a painting of them, filtered through his sensibility, even in a friendly profile.
    • He says capturing someone's self-image is the job of a PR person. His goal is a picture recognizable to people who know the person and resonant to people who do not.
    • Tucker Max43:51 shows the other side of this. The meaning of your own story is yours to decide, even when the facts are fixed.

Sources

Part of Characters and Storytelling in the growth library.