Would you take a shot at something you cared about if your odds of success were 1.4%? Font Awesome founders Dave Gandy and Travis Chase did exactly that when they applied to Y Combinator back in 2014. And in the years since, Font Awesome has racked up plenty of failures right alongside the wins. 'Cos that's just what happens when you're building something awesome.
In this episode, we go digging through Font Awesome's own flops (a product name that confused customers, a CDN experiment that converted exactly ONE person in three months) and line them up next to the real-life Museum of Failure. Which is hilariously an actual museum, started in Sweden in 2017, dedicated entirely to products that didn't make it. Expect Colgate's short-lived frozen dinners, a cologne no biker asked for, and the Nintendo Power Glove.
We also go back to a 2023 conversation with Dave Gandy about flunking out of MIT (twice), what it means to have the freedom to fail, and how a completely unprepped first Y Combinator interview turned into a second shot years later. And the second shot at YC was built on meticulous prep, a childhood friend's help at the Mountain View Public Library, and an unexpected connection with a YC partner.
The through-line: none of this looks like a success story on its own. But it's basically the only way Font Awesome got built.
What We Cover
Font Awesome's own quarterly product failures: Fort Awesome and the Font Awesome CDN
How a "failed" CDN experiment quietly built the email list that powered a record-breaking Kickstarter
Dave Gandy on flunking out of MIT, twice
A tour through the real-life Museum of Failure: Colgate Kitchen (and the lasagna that probably never existed), Harley-Davidson Cologne, and the Nintendo Power Glove
Dave's first Y Combinator interview (zero prep) versus his second (a lot of prep, a library, and some serious spreadsheet work)
Why humility, not confidence, is the trait Font Awesome hires for
Timestamps
00:00 — Would you take a 1.4% shot? Font Awesome's Y Combinator odds
00:03 — A quick tease: meet "Fort Awesome"
00:03 — Clip: Dave Gandy on startups, believing the lie, and finding your real limits
00:04 — The Fort Awesome experiment — and the name confusion that helped sink it
00:04 — Font Awesome CDN: a full quarter of work for one signup
00:05 — The quiet payoff: how that "failed" CDN built the email list behind the Kickstarter
00:06 — Dave on flunking out of MIT — twice
00:07 — Inside the Museum of Failure: Colgate Kitchen (and the lasagna that almost certainly never existed)
00:09 — Harley-Davidson Cologne: bikers said no thanks
00:10 — The Nintendo Power Glove — so bad it inspired a movie line, and still helped shape the Wii Remote
00:13 — Dave's first Y Combinator interview: no plan, no prep
00:13 — Round two: Ryan, the Mountain View Public Library, and the Adobe Typekit comps
00:15 — The Kevin Hale interview and finally clicking
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