The Odyssey: A Decades-Long Search for the Book That Shaped a Career, with Jerry Cobb [Ep. 05]
Jerry Cobb and I met almost five years ago, going through Schwab's Executive Leadership Program together — he was leading it, I was a participant. A few months back, a LinkedIn post of his stopped me mid-scroll: a book he'd read as a ninth grader hadn't just shaped his career, it had shaped his life. That's the whole premise of this show, so I knew he had to be a guest.
Jerry read The Odyssey in Bill Hansen's ninth-grade English class at Portola Junior High, the same year he lost his father. He didn't clock the connection at the time. Looking back now, decades later and prompted by Christopher Nolan's film, he can see how completely Odysseus's long way home mapped onto his own path from journalism into the financial world, a career he still describes as one long wander. He spent years hunting for the exact 1957 edition he read as a teenager, margin notes from other students and all, and finally tracked it down with an assist from AI. Opening it again, he told me, felt like the book coming home the way Odysseus finally does.
We also get into The Phantom Tollbooth, the childhood book that shaped how Jerry thinks about curiosity and screens with his own kids, and Grant, Ron Chernow's biography of Ulysses S. Grant, which Jerry leans on constantly in his work coaching RIA leaders through how lonely the job actually is. Toward the end, Jerry walks me through the reading list inside Schwab's RIA Executive Leadership Program, the book behind the eight-step change framework he uses with clients, and the one title he thinks everyone in wealth management should read that has nothing to do with finance.
In this episode
Why Jerry reads, and how a stranger's book recommendation overheard on a flight (The Wager) was enough to send him to buy a copy sight unseen
The Odyssey: Bill Hansen, Portola Junior High School, and the year Jerry lost his father
The decades-long hunt for the exact 1957 edition Jerry read as a ninth grader, and what it felt like to finally track it down
The Phantom Tollbooth, and the line about time Jerry still recites to his own kids
Grant, Ron Chernow's biography of Ulysses S. Grant, and what it taught Jerry about leadership being hard and lonely
Inside Schwab's RIA Executive Leadership Program — what it is, and the reading list behind it (Radical Candor, Being the Boss, Our Iceberg Is Melting, and more)
Unreasonable Hospitality, and the one book Jerry thinks everyone in wealth management should read that has nothing to do with finance
Books mentioned
Notable quotes
"It was like the book had come home to me in the way that Odysseus finally makes it home." — Jerry Cobb, on finally tracking down the exact 1957 edition of The Odyssey he read in ninth grade
"Whenever you go home a little bit uncomfortable about a choice or a decision you've made, you're exactly in that leadership zone." — Jerry Cobb, on what Grant taught him about leadership being hard and lonely
"Leaders are made, not born. It is a learnable skill set." — Jerry Cobb, on the founding philosophy of Schwab's RIA Executive Leadership Program
Chapters
(00:00) Welcome, and the Schwab Executive Leadership Program where Matt and Jerry met
(00:41) Why Jerry reads
(01:28) How Jerry picks his next book — the overheard recommendation for The Wager
(02:34) The Odyssey: Bill Hansen, Portola Junior High, and the year Jerry lost his father
(05:40) The lines from the book Jerry has memorized, and the search for his exact edition
(09:07) Finding the book at last, with an assist from AI
(12:06) The Phantom Tollbooth: curiosity over screens
(16:16) Grant, and why leadership is hard and lonely
(21:51) Inside Schwab's RIA Executive Leadership Program
(24:45) The ELP reading list: Radical Candor, Being the Boss, and more
(27:58) Kotter's eight-step change framework
(33:01) Lightning round
(34:28) Unreasonable Hospitality, and Jerry's top recommendation for the industry
(36:45) How to connect with Jerry, and close
About the guest
Jerry Cobb, MBA, ACC, is a Senior Business Management Consultant at Charles Schwab and helps lead Schwab’s Executive Leadership Program, the firm's year-long leadership-development program for next-generation RIA leaders. Before Schwab, he spent years as an on-air financial journalist, including a stint as CNBC's senior West Coast correspondent, before moving into marketing and communications at Kolbe Corp, the Phoenix firm behind the Kolbe Index. He's also an ICF-certified coach (Associate Certified Coach), work that shows up directly in how he runs Schwab's coaching-driven leadership curriculum.
Connect with Jerry
