Jimmy Soni is a professional speechwriter and author of deeply researched biographies, including a book on the early days of PayPal. In this episode, he shares his philosophy and practical methods for writing serious non-fiction, drawing on lessons from legendary biographers like Robert Caro and Walter Isaacson. He treats writing like an athletic discipline, emphasizing rigorous research, structured processes, and overcoming psychological barriers to produce work that stands the test of time.
Writing as a Learning Journey
Soni describes his approach as “writing upward” rather than downward.
Writing downward is when an expert distills their deep knowledge for others.
Writing upward is when the writer knows little about a subject at the outset and learns alongside the reader, making the process of discovery part of the narrative’s appeal.
This method forces him to make complex topics accessible because he himself is encountering the terminology and concepts for the first time.
How He Chooses Book Ideas
He maintains a running Google Doc called “books I should write someday” filled with ideas sparked by things he encounters.
If he cannot find an existing book on a topic, he adds it to the list.
He commits to a project only when he can identify an “empty space on the bookshelf”—a story that has not been told and that he is uniquely positioned to tell.
He avoids copycat books and aims to contribute something new, even if it takes four to six years to complete.
The Entrepreneurial Mindset in Writing
He views writing through an entrepreneurial lens: identifying a gap in the market and deciding to fill it himself.
For the PayPal book, he noticed that while the founders were heavily covered, no one had deeply explored the formative 1998–2002 period when they all worked together.
He saw an opportunity to uncover underexplored stories from a culturally significant era.
Research: Going Beyond the Obvious Sources
Soni emphasizes interviewing people at the periphery of a story, not just the famous figures.
Famous subjects often give rehearsed answers, while lesser-known individuals offer fresh, unrehearsed insights.
Example: He found the name Ed Bogas on an early PayPal cap table. Bogas was a musician and chess player, not a typical investor. Through persistent googling and a cold call, Soni reached him and learned that Peter Thiel had raised seed money from Bogas based on the intensity he observed during their chess games—a story Thiel himself likely would not have recalled.
He believes the most interesting stories come from people who do not usually seek the spotlight.
Managing Information and Notes
He uses a combination of tools to organize vast amounts of research:
Google Sheets to track interviewees, dates, notes, and file links.
Cloud storage with redundant backups (including thumb drives) to prevent data loss.
Otter AI for transcriptions, which he prefers for its flat fee and usability.
After each interview, he immediately records a voice memo of his impressions and types a brief summary in a Google Doc.
This captures vivid details that memory would otherwise decay, such as Peter Thiel pulling out his phone mid-interview to check PayPal’s current market cap against competitors—a moment that revealed his enduring competitive drive.
Writing Like an Athlete
Soni draws heavily from sports metaphors, inspired by Michael Jordan and the Chicago Bulls.
He treats writing as a process of doing reps, sets, recovery, and discipline.
He sets daily word count goals and uses psychological tricks to stay motivated, such as Scrivener’s color-coded word tracker that turns green when the target is met.
He believes the true titans of business, like Elon Musk and Peter Thiel, operate with the same intensity and dedication as professional athletes, even if it is less visible.
Overcoming Writer’s Block and Fear
He acknowledges that fear, anxiety, and imposter syndrome are constant companions in writing.
Voice typing in Google Docs: When stuck, he activates voice typing, covers his screen with a manila folder, and describes the scene aloud. This bypasses the anxiety of seeing imperfect text and allows raw material to flow.
Writing on his phone: He drafts and edits on his phone, which forces tighter sentences due to the small screen and reduces distraction because switching apps is harder than opening new browser tabs.
He also uses timed compression exercises: telling a story in five minutes, then two, then 45 seconds, to distill it to its essence.
The Editing Process: Reduction and Refinement
He wrote approximately 470,000 words of raw material for a final book of about 170,000 words.
He uses Scrivener to organize raw material chronologically (e.g., folders for 1998, 1999, etc.) and then copies it into Google Docs for shaping and refining.
Each chapter went through 13 Google Docs iterations and five PDF iterations, totaling around 17–18 revisions.
He compares editing to a sauce reduction—boiling down material to its essence—or to Michelangelo’s approach of chiseling away stone to reveal the statue within.
Developing Taste Through Study
To decide what to keep and what to cut, he studies books he admires intensively.
He read Brad Stone’s The Everything Store 16–17 times, analyzing how Stone wove personal details into a business narrative.
He adopted Stone’s technique of exploring the origin of company names, leading him to deeply research where “PayPal” came from.
He applies the Apple model of “surprise and delight,” aiming to include a gem on every page—something that makes the reader smile, laugh, or think.
Example: He transitioned a section on Sequoia Capital’s investment in x.com with the phrase “Funding secured,” a nod to Elon Musk’s famous tweet, turning a dry financial detail into an inside joke.
The Importance of Warmth in Writing
He values warmth, especially when writing about larger-than-life figures.
Warmth comes from specific word choices that evoke feeling and from writing with empathy, reminding readers that even the most successful people were once uncertain young adults.
Example: He recounts Elon Musk standing shyly in the lobby of Netscape, too scared to talk to anyone, then leaving—a moment of vulnerability that humanizes Musk before he became a global figure.
Writing as a Team Sport
He rejects the myth of the solitary writer and emphasizes collaboration.
He hired a professional fact-checker, Ben Kaylin, who rigorously verified every claim, cross-referencing interview transcripts and documents over three intense rounds.
He sent daily paragraphs to a college friend, Justin Richmond, for feedback, treating him as a trusted sounding board.
He encourages writers to hire editors or seek feedback from friends, even informally via text, to gain perspective and improve their work.
The Role of Speechwriting in His Craft
His day job as a speechwriter cross-trains him for book writing.
Writing speeches, op-eds, and ghostwritten pieces for different audiences builds volume, adaptability, and the ability to persuade.
He recommends that aspiring writers offer to draft speeches or presentations for others to gain practice and build a reputation.
Inhabiting the World of the Subject
While writing the PayPal book, he maintained an extremely narrow media diet.
He avoided contemporary news about the founders to prevent modern biases from coloring his historical narrative.
He immersed himself in the late 1990s and early 2000s by reading period newspapers, watching documentaries, and studying the cultural context of the dot-com era.
He describes himself as a “method writer,” inhabiting the universe of his subjects to authentically capture their perspective.
Morning Routine and Discipline
During the book, he woke at 4:00–4:30 a.m. every day, including holidays and vacations.
His routine was superstitious and unchanging: same clothes, same lighting sequence, sparkling water, caffeine, a brief meditation visualizing the finished book, and 10 minutes of reading The Everything Store for inspiration.
He worked from 4:00 a.m. to 8:00 a.m. on writing before starting his day job, treating this time as sacred and non-negotiable.
Lessons from Mentors
Walter Isaacson encouraged him early on and advised him to “be chatty” in his endnotes, using them to show the depth of research and the diversity of sources behind each claim.
Robert Caro inspired him to “turn over every page” in research and to interview peripheral figures to understand the core of a story. Caro’s practice of writing to a predetermined final sentence is a technique Soni admires but did not fully adopt.
Alice Mayhew, his late editor at Simon & Schuster, taught him to write the introduction last, after the book is complete, so it can serve as a true guide to the story’s dimensions.
Productive Discomfort and a Letter to His Daughter
In the book’s acknowledgments, he wrote a letter to his daughter, Venice, reflecting on the lesson of productive discomfort.
The PayPal founders did not always get along, but their disagreements were generative—they pushed each other to improve.
He tells his daughter that while he loves her too much to be her toughest critic, she should seek out friends and mentors who will challenge her honestly and help her grow.
He frames this as one of the core elements of the PayPal story: a culture where people felt obligated to bring their best, even when it was uncomfortable.
