Is writing a book still worth it when AI, short video, and a shrinking web compete for every reader?
Tren Griffin, author of Charlie Munger: The Complete Investor and the 25iq blog, is writing his eighth book, on investing principles, for Harriman House.
Jim O'Shaughnessy, who now runs the publisher Infinite Books, compares notes with him from both sides of the table.
They cover why book income follows a severe power law, why every author is really starting a business, how Infinite Books uses AI fact-checkers and A/B-tested covers, the Charlie Munger lesson that changed Tren's life during the dot-com boom, why knowing more makes you a better AI prompter, and how to find a passion worth following. Tren's rule for writers: "Don't be boring. It's deadly."
KEY INSIGHTS
- Write a book for reasons other than money. Tren calls book income "a very severe power law." The payoff is the ideas, the mentoring, the legacy, or a career, as What Works on Wall Street was for Jim.
- Every author is starting a business. After "what's your book about?", a publisher's most important question is "who's your community?"
- Build the book in public. Community, presales, and early word of mouth decide how hard publishers and distributors push a title.
- Give before you ask. Infinite Books sends free copies to writers covering adjacent topics, with no request attached, and coverage often follows.
- Test, don't trust taste. In Infinite Books' A/B tests, covers the whole team loved have finished last.
- AI rewards people who know more. Deep knowledge means better prompts and a faster nose for hallucinations.
- You only have to get rich once. Applying Munger's principles during the dot-com boom, Tren sold half his internet and telecom holdings, and says it changed his life.
- Happiness is in your control. Tren's rule for problems that aren't yours: "Don't take the turd."
READ TREN
25iq: https://25iq.com
INFINITE BOOKS
https://infinitebooks.com
RELATED
Tren Griffin on Infinite Loops (Ep. 86): https://youtu.be/NUHhpToAdGA
TIMESTAMPS
0:00 Intro
0:51 Why Jim Started a Publishing Company
1:23 How Book Deals Are Changing
1:53 Why Write a Book If It Won't Make Money
2:57 How a Book Put Jim on the Map
3:33 Books That Reach Decision Makers
5:28 Every Author Is Starting a Business
6:34 Inside Infinite Books: AI Fact-Checking and Marketing
10:06 Paying It Forward and a 70/30 Author Split
13:14 Write for Yourself, Then Tell Stories
14:09 The Morgan Housel Hire That Got Away
15:50 Why Infinite Books A/B Tests Its Covers
18:26 Finding a Book's Readers With Data
19:52 Give Before You Ask
20:30 Word of Mouth and Customer Acquisition Cost
21:58 Free AI vs. Frontier AI
25:14 AI Indexing and Text Blindness
28:34 Nobody Has Perspective on Themselves
29:02 Why Writing for Money Backfires
33:13 What Authors Hate About Publishing
35:10 Bill Gurley's Runnin' Down a Dream
36:50 The Grocery Store Theory of Life
38:51 Charlie Munger: You Only Have to Get Rich Once
41:08 Simplifying the Kelly Criterion
43:31 The Curse of Knowledge
44:57 How Tren Profiles Great Investors
46:52 What Bad Reviews Teach
50:29 Why AI Feels Like the 1993 Internet
50:45 AI Is Dual Use, Like Fire
56:26 AI Lets Authors Own the Whole Stack
58:00 Why Books Follow a Power Law
59:55 How to Build a Book in Public
1:02:51 Marketing When Distribution Costs Almost Nothing
1:04:32 Why Writing Needs Uninterrupted Time
1:06:04 Why Jim and Tren Stopped Using Google
1:07:38 Knowing More Makes You a Better Prompter
1:08:24 Is Serious Reading Dying?
1:15:08 Using AI to Read Hard Books
1:18:53 How to Become More Curious
1:21:50 Try Everything, Collect Stories
1:23:14 The Great-Story Test
1:25:13 Growing Up Curious in Seattle
1:29:16 Tren's Next Book
1:30:42 Happiness Is a Byproduct
1:31:48 Don't Take the Turd
1:34:36 Reciprocity, Manipulation and Social Media
1:38:52 No W-2 Doesn't Mean Retired
1:40:18 Never Retire: Jim's Grandfather's Advice
1:42:03 Two Ideas for the World
ABOUT THE GUEST
Tren Griffin is an investor and writer. He writes the 25iq blog and is the author of Charlie Munger: The Complete Investor and A Dozen Lessons for Entrepreneurs. He spent years at Microsoft and was a partner at Eagle River, the private investment firm controlled by Craig McCaw. He is writing his eighth book, on investing principles, for Harriman House.
ABOUT THE HOST
Jim O'Shaughnessy is the founder and CEO of O'Shaughnessy Ventures and the author of the New York Times bestseller What Works on Wall Street. He founded O'Shaughnessy Asset Management and hosts Infinite Loops.
