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The Ostrich Report AKA: The Marketplace Podcast Week 5 eBay Part 2

Sliding Doors

#ecommerce The marketplace podcast you didn't know you asked for (just like AI) is back. The Ostrich Report Ep 5 – eBay Part Two 🚨The Sliding Doors of eBay: Part 2 – Electric (But Still Manual) Boogaloo 🚨

🎙️The Ostrich Report Ep 5 just dropped, and if nostalgia had a stock price, we'd all be rich… until activist investors spun it off for parts. Say his name Hendrik Laubscher - Humperdink (IYKYK)

Three big takeaways from our gloriously unhinged post-mortem on eBay's ‘meh decade’:

🔥 1. eBay didn’t lose its edge. It sold it.

“If eBay executed and innovated, we wouldn’t have seen The RealReal, StockX… or even Zillow.”

They were first to everything. Trust, buyer protection, vertical communities, Skype integration before Zoom was even born. But somewhere between 2005 and Carl Icahn’s morning espresso, they swapped imagination for margins. There, I said it.

💸 2. Innovation died in San Jose. It’s been replaced with Excel.

“We’re doing nothing and we’re happy about doing nothing.”

From spinning out PayPal under pressure to flopping the Skype play twice, eBay mistook "innovation" for "cash-out." Spoiler: The CEO who green-lit PayPal’s spin-off became Chairman of PayPal. Misalignment? Or just Silicon Valley's version of dating your ex’s richer sibling? In many reality shows, this seems to be normalized.

🪦 3. AI isn’t the future at eBay. Apparently, advertising is.

“We are in mid-2025, and I’ve yet to see any mention of how eBay plans to use AI. But ad spend? That’s the hill they’re dying on.”

While competitors like Amazon and Walmart build fortress-like AI ecosystems, eBay hands over its crown jewels (read: data) to third parties like Perplexity, hoping nobody notices the silence.

We asked: Can eBay come back?

And we answered: Sure, if Yahoo did.

This isn’t just a requiem for eBay, it’s a warning for any company that confuses shareholder value with customer value, or that thinks maintaining the status quo is a strategy.

You can be the tortoise in a race… but not if you keep selling your shell for parts.

🎧 Listen to the episode. Mourn. Rant. Discuss.

Then ask yourself: Is my business building the future… or renting the past?

#TheOstrichReport #MarketplaceMadness #eBay #ecommerce #InnovationFail #CarlIcahnRuinedEverything

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