Jared Dillian: All Things Writing, Creative Process, and Craft

Episode Summary

Executive Summary: Jared Dillian discusses his path from Coast Guard officer and Lehman trader to prolific writer, emphasizing that writing improved through relentless daily practice, editing, and risk-taking. He contrasts the mental makeup of trading and sports, explains why finance can feel “depraved,” and argues that ideas matter less than execution. The conversation centers on craft, discipline, mental health, and creating work that outlives you.

Main Topics: Dillian’s path from markets to writing (Priority: 5/5): He recounts growing up in Connecticut, attending the Coast Guard Academy, working in intelligence, earning an MBA, trading at Lehman, and then transitioning into newsletters, books, and essays after the 2008 collapse. Trading psychology and risk appetite (Priority: 5/5): Dillian explains that he began as deeply risk-averse due to military culture, but learned to embrace risk through index arbitrage, ETF trading, and eventually prop trading, with large positions and no need for permission. Writing as a daily craft (Priority: 5/5): He argues that writing is a muscle that atrophies quickly and must be practiced every day. His workflow is constant output—newsletter, essays, short stories, and book work—rather than sporadic inspiration. Finding voice and style (Priority: 4/5): Dillian describes his style as gonzo, stream-of-consciousness, honest, and willing to break rules when it serves the piece. He distinguishes his approach from more literary, sensual fiction writing. Editing, feedback, and improvement (Priority: 4/5): He stresses that first drafts are not enough, that editing for flow is essential, and that writers need outside feedback. He also notes that the first million words may be bad before quality emerges. Finance culture and ‘depravity’ (Priority: 4/5): Dillian expands on why finance can be depraved: greed, status, excess, political tension, and a culture centered on money and consumption. He says the culture improved after the crisis but risk-taking declined. Meaning, legacy, and creating work that lasts (Priority: 4/5): He says he wanted to move from making markets to creating enduring work—books, essays, and music—that will outlive him and provide broader value beyond a trading career.

Key Arguments: Writing skill is built through repetition; he writes every day and says the muscle atrophies quickly without regular use. Trading and sports are not identical; he was mentally weak in sports but suited to trading because the required temperament differs. Ideas are cheap; in finance, execution and risk management matter far more than idea generation. Good writing requires editing for flow and accepting that first drafts are usually poor. A writer needs to break rules selectively to preserve voice, but must still revise and improve. Finance can be culturally corrupt or “depraved” while still being essential to capitalism and liquid markets. Creative work gives lasting legacy in a way trading careers usually do not. The first million words may be terrible, so progress requires patience, discipline, and volume.

Data Points: Years at Lehman Brothers: 7 years - Dillian worked at Lehman from 2001 until the 2008 bankruptcy. Index arb exposure duration: 1-2 seconds - He said index arbitrage risk was only held for a second or two. ETF trade size: 1-2 million shares - He described facilitating very large ETF customer trades. ETF trade notional: $300M-$400M - Large SPY trades on the ETF desk. Prop-book position example: $200M tens / $1B twos - Example of a yield-curve steepener he ran on his own book. Daily newsletter length: ~1,500 words - He writes the Daily Dirt Nap every morning. Total daily output: ~3,000-4,000 words/day - He says he writes newsletters, essays, and short fiction at this rate. Substack subscribers: ~6,200 - He estimated the size of his Substack audience. Hypothetical paid Substack income: ~$80,000/year with 1,000 paid subscribers - He discussed why he kept the newsletter free instead of paywalling it. National writing competition awards: ~700 awards nationwide - He won an award from the National Council of Teachers of English in high school. Age when starting MFA: 46 - He began graduate school late in life to improve his writing. Citywide racquetball result: 3rd place - He placed third in a Myrtle Beach citywide tournament. First million words: Terrible - He cited Robert Olen Butler’s claim that early output is mostly bad. Books written: 4 total (3 published, 1 upcoming) - He has written three books and expects a fourth next year. Short-story collection cited: Airships - He named Barry Hannah’s collection as a favorite.

Pivotal Quotes: "If you played tennis for eight hours a day, you would get pretty good at tennis. If you played piano for eight hours a day, you would get pretty good at writing." — Jared Dillian: He explains that writing improves through sustained practice, not talent alone. "Ideas are cheap. Ideas are very, very cheap. Like a lot of people think the idea is the biggest thing. It's really not. It's the smallest thing." — Jared Dillian: He argues that execution and risk management matter more than idea generation in finance and writing. "God has a much bigger imagination than I do." — Jared Dillian: He reflects on how unexpected his life and career turned out after his hospitalization.

Implications: The episode suggests that long-term creative and investing success comes from discipline, iteration, and risk-calibrated execution. For listeners, the takeaway is to practice daily, seek feedback, and build work that compounds and endures.