Author, Racing Against Time: On Ironman, Ultramarathons, and the Quest for Transformation in Mid-Life

What if “later” suddenly became “now”?

On this episode of “Ira’s Everything Bagel,” Ira sits down with Jeffrey Weiss, author of Racing Against Time: On Ironman, Ultramarathons, and the Quest for Transformation in Mid-Life, for a powerful conversation about aging, endurance, and the courage to reinvent yourself.

Jeffrey didn’t begin his athletic journey as a lifelong competitor. He ran his first 10K at 48. What started as a simple health goal turned into marathons, two finishes at Ironman Arizona, and a 72-mile ultramarathon — all after most people start talking about slowing down.

In this personal conversation, Jeffrey shares:

How his father’s passing shifted his mindset from “someday” to “now”

The Vince Lombardi quote that fuels his discipline

Why it’s a marathon, not a sprint — in sports and in life

The truth about willpower (it only lasts about a month)

Why “baby steps” matter more than heroic bursts of motivation

How to fight the resistance of the mind

Why exercise creates optimism — not just muscle

The question he keeps asking himself: “Why am I doing this?”

How endurance keeps him energized and relevant in the workforce

And what kind of life he wants to be living at this age

This isn’t just about racing. It’s about choosing your path. Taking ownership of your health. And deciding — intentionally — how you want to live the years ahead.

Because maybe the real race isn’t against other competitors.

Maybe it’s against time.

ABOUT JEFFREY:

Jeffrey Weiss is a successful business executive, an accomplished author of three books, and a two-time Ironman and an ultramarathoner. Racing Against Time: On Ironman, Ultramarathons, and the Quest for Transformation in Mid-Lifetells of his midlife adventures in extreme sports, including finishes at Ironman Arizona (twice) and the 72-mile ultramarathon Midnight Express between the ages of 57 and 61. 

He is also the co-author of I Am My Brother’s Keeper which chronicles the American and Canadian volunteers who served in all branches of the Israel Defense Forces during the 1948 War of Independence, and Fighting Back: Stan Andrews and the Birth of the Israeli Air Force

Jeffrey is featured in Nancy Spielberg’s acclaimed 2014 documentary “Above and Beyond” (available on Amazon Prime), which tells the story of American pilots in Israel’s founding air force and earned 22 film festival awards. He also appears in the 2000 documentary “Israel’s Forgotten Heroes,” narrated by Hal Linden.

Fluent in Hebrew, Jeffrey completed a year of law school at Bar Ilan University and holds a law degree along with master’s degrees in International Law (Georgetown University Law Center) and Biotechnology (Johns Hopkins University). In addition to his academic and writing accomplishments, Jeffrey is an experienced entrepreneur, having served for more than a decade as a C-suite executive at a startup that was recently acquired for $3 billion.

Jeffrey lives in Tel Aviv, where in 2024 he founded Stickers of Meaning, a project that preserves and educates about the memorial stickers that have appeared throughout Israel since October 7, 2023—honoring the fallen and inspiring the living with messages of love, purpose, daring, and joy.

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