Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

No, this podcast does not typically feature guests.

Winning at Work

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by John Caldwell

7 episodes

Updated Daily

Accepts GuestsHas Sponsors

Podcast Overview

Work is too important for bad advice. Winning at Work is the podcast for people navigating their careers without the fluff, "hustle porn," or theories from people who’ve never been in the room. Host John Caldwell spent 35 years at the sharp end of music and gambling. He sold 40M records as a label president and helped build the online poker industry. He’s made and lost fortunes, managed legends, and built teams from scratch. No scripts, no guests, no theory. Just honest stories and straight talk about what it takes to win—and what winning actually means.

Language

🇺🇲

Publishing Since

4/1/2026

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Recent Episodes

May 12, 2026

The Wizard in the Blue Shirt - AI and your job

In the early nineties I needed a website built for a band I was managing. The guy who could build it was, to us, a wizard — almost nobody else in the industry could do what he did. He knew it. And he priced accordingly.A couple years later, I ran into him at the Best Buy tech counter. Blue shirt. Name tag. Still defending the same number he'd quoted us.This episode is about what his story tells us about AI right now — and about the real risk in any major technology shift. Spoiler: it's not ignorance. 📬 Newsletter + free guide Reading the Room: The Seven People You'll Meet at Work → winningatwork.io

May 5, 2026

The Wise Uncle — How to Survive 35 Years Inside the Same Company

Most people can't last five years at a turbulent company. John's friend Franklin has lasted 35 — at one of the most chaotic television networks in America. Not by hiding. Not by playing politics. Something else.In this episode, John shares what Franklin told him over a beer at a hockey game about how to actually survive inside a big organization for the long haul. Two answers — one expected, one that genuinely surprised him: the idea that after enough years, you stop being valuable for what you know about your industry and start being valuable for what you know about your organization. The bodies, the battles, the real map underneath the org chart.Along the way: why the most reliable people often outlast the most brilliant ones, the difference between being willing to do anything and being the person everyone dumps on, and the political intelligence that separates Franklin from another character John has talked about — Charlie, who played a similar game but without the integrity.Some people win by leaving. Franklin won by staying. Both take courage. Only one takes patience — and it might be the harder one.📬 Newsletter + free guide Reading the Room: The Seven People You'll Meet at Work → winningatwork.io

April 28, 2026

The Career Triangle: Why You Can Have Meaning, Money, or Balance — But Almost Never All Three

Every young professional gets sold the same lie: that the right job will deliver meaningful work, great pay, AND work-life balance. After 35 years at the sharp end of two industries, John Caldwell is here to tell you it almost never works that way — and explain why understanding the trade-off is the thing that makes a career feel calmer instead of constantly frustrating. In this episode, John borrows a rule from his friend Dave, a TV commercial producer who used to tell every client the same thing: "Your project can be good, fast, or cheap. Pick two. You can't have all three." It turns out careers work exactly the same way. What you'll learn:● The three corners of the Career Triangle — and which one you're probably standing on right now● Why the Founder Path (meaning + money) costs you balance, and when that trade is worth it● The "Professional Comfort" trap — when money and balance start to feel like a cage● How to use trade-off framing to manage up (the exact language to use when your boss asks for the impossible)● Why your triangle will rotate at least twice in your career — and how to see the rotation coming● The one thing senior leaders quietly envy about the chaotic, uncertain phase early-career people want to escape A short, practical episode for managers and operators who are tired of pretending they can have it all — and ready to make intentional choices instead. Read the full essay and subscribe to the newsletter: https://winningatwork.beehiiv.com

7 total episodes available

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Frequently asked questions

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What is Winning at Work?: Work is too important for bad advice. Winning at Work is the podcast for people navigating their careers without the fluff, "hustle porn," or theories from people who’ve never been in the room.

Host John Caldwell spent 35 years at the sharp end of music and gambling. He sold 40M records as a label president and helped build the online poker industry. He’s made and lost fortunes, managed legends, and built teams from scratch.

No scripts, no guests, no theory. Just honest stories and straight talk about what it takes to win—and what winning actually means.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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