Winning Ugly
What an ugly World Cup final teaches about building companies.
Last Sunday I was in the stadium when Spain beat Argentina to win the World Cup. One goal in 106 minutes. Sixty-five percent of the ball. Argentina did not land a single shot on target all night.
That evening I had dinner with a good friend from Argentina in a quiet traditional Italian joint in uptown NYC. Over a few Fernets, we kept discussing the final, and he could not let the result go, and between bites he repeated the same verdict like a rosary. “España juega demasiado feo.” Spain plays too ugly. No verticality, he said. A thousand sideways passes. A team that puts you to sleep and calls it football.
To be fair, he was not wrong about the aesthetics. Spain completed more than eight hundred passes that night. It can feel like watching someone defuse a bomb very slowly.
Back at the hotel my Twitter feed agreed with him. Boring. Death by possession. The internet had run out of patience with the new champions of the world.
And I caught myself nodding along. Then it hit me. Spain had the trophy. The critics had the adjectives.
Nobody in that locker room will spend one second on the adjectives. In twenty years the record book will say champions. It will not say how. My friend knew it too, which is exactly why he could not stop going back to it.
That World Cup final night dragged an old tennis book “Winning Ugly” out of my memory, written by a pro with famously unlovely strokes who made a career of beating beautiful players.
When it gets real
The Spain World Cup final reminded me of Mailchimp, the largest bootstrapped exit in history.
Mailchimp did the opposite of building a sexy, Forbes cover-worthy company.
Email newsletters were the least glamorous corner of tech, a side hustle inside a small Atlanta web design agency, about as far from Silicon Valley as software gets. Ben Chestnut and Dan Kurzius took zero venture capital for twenty years, turned down the funds and the flattering offers, and kept selling the boring product to small businesses, year after year.
In 2021 Intuit paid $12 billion for it. Every fashionable thing they refused went straight to the scoreboard. The market does not give style points.
Worth your time
Read Winning Ugly by Brad Gilbert, the book that dinner dragged out of my memory. Gilbert’s strokes were famously not pretty. He beat more gifted players for a decade anyway by thinking better: find the weakness, take the win however it comes. It says tennis on the cover. It is really a manual for beating prettier competition.
Final thoughts
The world will forget the boring Spanish team and will forever remember the champions. Note to self: “winning ugly counts just as much as winning”
Thanks for reading.
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