Fast Fails: Ben Silbermann’s Wrong Turn to Pinterest
Our third Friday drop. Still failing forward.
Welcome back to Fast Fails—founder flameouts with comeback energy.
Every Friday, we dig up the story behind the stumble—because great founders don’t just launch. They reroute. Reframe. Return.
Today’s feature? Ben Silbermann.
Because before Pinterest became a household name…
He built a mobile shopping app that nobody wanted.
But he was watching closely—and what users did instead?
That changed everything.
Let’s get into it.
From Missed Carts to Master Curation: The Ben Silbermann Story
In 2009, Ben Silbermann launched Tote, a shopping app that let users browse catalogs and bookmark products to buy later.
It was meant to be a mobile mall—an e-commerce aggregator for fashion and lifestyle brands.
The problem? Nobody was checking out.
Despite sleek design and a decent early user base, retailers weren’t converting. Payment integrations were clunky. Users weren’t shopping as expected.
But Silbermann noticed something else.
They were saving things. Constantly.
Users weren’t treating Tote like a storefront—they were treating it like a visual clipboard. A wish list. A scrapbook.
That subtle behavior?
That was the signal.
So he shut down Tote.
And built something entirely new around that insight:
Pinterest.
A visual platform not for buying, but for collecting.
A tool for digital curation, not transactions.
And one of the most quietly powerful social platforms of the last decade.
By 2019, Pinterest IPO’d with a valuation over $12 billion.
Today, it has over 480 million monthly users—and is still one of the only social media platforms that doesn’t run on outrage.
📉 The Fail
Tote was supposed to be mobile shopping reimagined—but users didn’t behave like consumers. They behaved like collectors. The original product vision missed… but the user instinct didn’t.
💪 The Grit
Silbermann didn’t double down on the business model. He zoomed in on why users were saving and built a whole new platform around that one interaction.
✨ The Comeback
Pinterest flipped social media upside down—designed for inspiration, not attention. Its IPO in 2019 capped one of the greatest pivots in consumer tech history.
🗣️ Founder Quote
“Don’t take too much advice. Most people who have a lot of opinions about consumer internet, I think, really don’t have any idea. No one knows anything.”
— Ben Silbermann
Like this drop?
We’re doing it every Friday.
Comeback stories that cut through the noise.
📩 Subscribe for:
Vibe5 (Mondays) — 5 stocks under $50 with founder-led upside
VibeRecs (Wednesdays) — Founder deep dives, scored and cinematic
Fast Fails (Fridays) — Because failure’s part of the frequency