Dec 15, 2025
Can you build healthspan in your 50s, 60s and beyond? In our episode 239 conversation, Jeff Weiss says yes—and he’s got the miles to prove it. After his first 10K at 48, Jeff progressed to marathons, ultramarathons, and Ironman triathlons, discovering how structured training within smart guardrails, and the right mindset can unlock cardiovascular fitness, strength, confidence, and cognitive resilience in midlife. We explore practical ways to get started (and keep going), how to balance discomfort vs. danger, and why setting “big, hairy, audacious goals” fuels transformation far beyond sport.
Jeffrey Weiss is an entrepreneur, former C-suite leader with a
multi-billion-dollar exit, endurance athlete, and author of
Racing Against Time: On
Ironman, Ultramarathons, and the Quest for Transformation in
Midlife. Starting with a first 10K at 48, Jeff progressed to
marathons, ultras, and Ironman Arizona, discovering that
well-designed guardrails, progressive overload, and recovery can
unlock performance and vitality long after 50. He now shares
science-informed, experience-tested frameworks that help midlife
adults build cardiovascular fitness, strength, and
confidence—without heroics or burnout. Jeff speaks and writes about
the mindset that sustains big goals (BHAGs), how to distinguish
discomfort from danger, and why consistent training ripples into
career resilience, cognitive sharpness, and everyday joy.
Timeline:
00:30 — Why healthspan (not just lifespan)
matters
Framing fitness as a primary lever for aging youthfully.
04:26 — Discomfort vs.
danger
Learning to distinguish healthy challenge from true risk as we
age.
07:23 — Mindset & motivation that
stick
Races, structure, coaching, and the post-workout “well-being
effect.”
10:03 — Cardio, strength, and bone health in
midlife
Cross-training (run/cycle/swim + lifting) to support VO₂, muscle,
and bone density.
15:09 — Confidence, cognition &
BHAGs
How audacious goals translate to business grit and everyday
resilience.
25:37 — Guardrails for beginners
50–70+
Start simple, find what you enjoy, build gradually, and use
“conversational pace.”
33:55 — Injuries &
prevention
Early warning signs, backing off, and proactive physio to stay in
the game.
35:05 — One big takeaway
If you care about healthspan, make fitness a non-negotiable
habit.
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