Building Business In A Changing World W/ Craig Wipperman :: Ep 266 Mostly Middle Tennessee Business Podcast Mostly Middle Tennessee Business podcast

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Building Business in a Changing World w/ Craig Wipperman :: Ep 266 Mostly Middle Tennessee Business Podcast

3d ago 1:33:35

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Podcast Title: "Building Business in a Changing World"

What can a career that spans space‑shuttle electronics, cell towers, and corporate hypergrowth teach us about small business, culture, and entrepreneurship in Middle Tennessee? In this wide-ranging episode, host Jim sits down with business coach Craig Whipperman of Music City ActionCOACH for a candid conversation on how businesses grow, break, and reinvent themselves—and what that means for everyday owners and solopreneurs.

Together, they trace Craig’s unconventional path from engineering and accounting to auditing NASA contractors, then into the exploding wireless and cell tower industry, where he helped Crown Castle grow from hundreds to thousands of towers and employees. Craig shares what it’s really like to “build the plane while flying it,” how culture gets stretched and diluted at scale, and why he ultimately left a public company to help business owners one-on-one.

The episode dives into the mindset shift from employee to owner, the limits of traditional education, and why coaching, mentoring, and “guru culture” are not the same thing. Jim and Craig explore how AI, automation, and economic cycles are reshaping work, why trades and entrepreneurship are on the rise, and how faith, perspective, and continuous learning can turn crises into solvable problems. Along the way, you’ll hear stories about disguised cell towers, economic “pendulums,” George Carlin, and why the next generation may be the most cynical yet—and maybe that’s not all bad.

Episode Highlights:

How Craig went from space‑shuttle audit work to managing cell tower networks and obstruction lighting
What it means to “build the plane while flying it” inside a fast-growing public company
How rapid growth can transform—and sometimes fracture—company culture
The difference between owning a job and owning a true business
Why college often trains “obedient workers,” not owners and builders
How ActionCOACH and “business re‑education” help fill the gaps schools don’t cover
Coaching vs courses: real mentoring and questions vs one‑size‑fits‑all “guru” programs
Why AI and automation may hit white‑collar work like NAFTA hit manufacturing
The coming shortage in the trades and why many hands‑on jobs are more AI‑resistant
Economic and cultural cycles: insights from Ray Dalio, The Fourth Turning, and Pendulum
Social media, deepfakes, and the rise of a highly skeptical, disillusioned generation
Immigration, struggle, and what happens to a society that’s had it “too good for too long”
Craig’s “there is no crisis” philosophy—and how systems, preparation, and faith support it
Why continuous learning matters: “When you’re green, you grow. When you’re ripe, you rot.”
Where to find Craig online and why Jim wants him to get his own podcast going again
Whether you’re a small business owner, an aspiring entrepreneur, or simply rethinking your career in a changing world, you’ll find perspective, practical insight, and a reminder that growth, resilience, and good questions never go out of style. Listen, share, and be part of the conversation.

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Shoutout to Matt Wilson for lending his voice to the new intro of MMTBP.

Follow him and his podcast from which I may have borrowed the *mostly* concept:

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If you like Jim's Boston Scallys, click here to shop and order yours!
https://www.bostonscally.com/a/refer-a-friend/redeem/mqgpwi3u0zgm89vaxnv5crzvlolevo82rvcygsn5/1668
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***You hear Jim mention it on almost every episode, ME vs. WE and how 2023 will be 1943 all over again….order “PENDULUM:How Past Generations Shape Our Present and Predict Our Future”:
https://a.co/d/7oKK7Ip
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The co-author of Pendulum wrote a myriad of other books and started a non-profit 21st Century Non-Traditional Business School that you should really check out:
Wizard Academy - www.wizardacademy.org
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