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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of the Stronger Is Better Podcast, Nick Delgadillo sits down with Starting Strength Gyms founder Ray Gillenwater for a wide-ranging conversation about entrepreneurship, vision, and the founding story of Starting Strength Gyms. Ray shares how his experiences in tech, corporate leadership, and global markets led him to Starting Strength—and why strength training is at the core of building better people, teams, and businesses.
They explore the parallels between barbell training and business operations, discuss lessons from launching a franchise, and highlight the power of doing hard things. From his time at BlackBerry to the launch of Starting Strength Gyms, Ray’s story offers valuable insight for entrepreneurs, coaches, and anyone seeking freedom through ownership.
00:00 – Intro: Ray returns to the podcast
00:44 – Ray’s background in tech and telecom
02:20 – First encounter with Starting Strength
04:50 – Discovering the program, contacting Rip
07:00 – Attending his first seminar and injuries
08:20 – Starting Strength retail vision emerges
10:24 – Franchising vs affiliation
12:42 – How the response to COVID tested the franchise
14:59 – Corporate vs mission-driven business
16:35 – BlackBerry in Southeast Asia
19:30 – Sales tactics and incentive alignment
23:19 – Launching BlackBerry Money, ahead of its time
27:30 – What went wrong at BlackBerry
30:00 – The draw of Starting Strength
31:35 – Bullshit in the corporate world
33:00 – Rip’s influence and brutal honesty
34:15 – Returning to the franchise—lessons learned
36:04 – Coaching gym owners like lifters
38:49 – Business fundamentals mirror training
40:26 – Product, people, and solving real problems
44:42 – Technical expertise vs human connection
48:30 – How to help the runner, the skeptic, anyone
52:46 – Weekly habits and business levers
54:20 – Vision, strategy, and scalable simplicity
56:34 – Why the culture makes it all work
57:37 – Hard physical effort = quality people
1:01:25 – Franchising done the right way
1:03:31 – Humility, hardship, and growth
1:06:35 – Closing reflections on freedom and purpose
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🔗 Brought to you by https://www.startingstrengthgyms.com
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