What if the real key to scaling your business isn’t a revolutionary product, but your ability to build a culture where “weirdness” is an asset and radical respect transforms politics into partnership?

In this electric episode, Cameron Herold sits down with John McDonald, Chief Operating Officer at Poshmark, to unpack how one of the world’s most beloved marketplaces keeps growing in spite of Goliath competitors and shifting markets.

Together, they reveal why most leaders get core values wrong, how Poshmark keeps small sellers winning (not just the giants), and what it truly takes to expand internationally without derailing your DNA. John’s stories are real, the lessons are battle-tested, and you won’t find a paint-by-numbers playbook here—only hard-won insights and rare candor from inside the trenches.

Don’t wait. Listen now to avoid building a company that stalls at “good enough,” or tears itself apart scaling fast. This episode unveils systems, strategies, and human truths you won’t hear anywhere else.

[00:00] – Why this “fan favorite” episode is back and the lesson it delivers for every second-in-command

[02:20] – What Harvard Business School actually teaches about decision-making in chaos

[05:28] – Unmasking Poshmark’s origin: Why the human touch, not tech, is their unfair advantage

[09:00] – The $1,000 sneaker flip… and how Poshmark makes money (no nickel-and-diming)

[13:24] – What really changes when you grow from 35 to 400+ people (and where companies go wrong)

[19:41] – How they killed company politics and the “respect” system that keeps silos from forming

[23:04] – Are your “core values” just words? The surprising reason Poshmark’s work (and most don’t)

[28:37] – How Poshmark protects small sellers—and why giving back unlocks explosive growth

[33:57] – The dangerous moment for org charts: when matrix thinking becomes non-negotiable

[40:55] – Why learning to listen is the hardest (and most critical) leadership skill for COOs

John McDonald is the Chief Operating Officer of Poshmark, a leading social commerce platform revolutionizing how the next generation shops and sells. With a deep background in marketplace management (including eight years at eBay), John’s powered Poshmark’s exponential growth and built culture-first teams that thrive. He’s a Harvard MBA, an operations architect, and a fierce advocate for scaling with love and discipline.

🔗 LinkedIn | Website

1. eBay
2. Ning
3. Procter & Gamble
4. Harvard Business School
5. University of California, Berkeley