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Stay Weird, Ponyboy
Why weird wins
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Viva La Vega
When Benjamin signs an email, he says “From Madeline and Ben.”
When Madeline signs an email, she says “From Ben and Madeline.”
It’s not random. It’s one of the ways they show up for each other as cofounders of Vega, AI-powered people lists for hiring, dating, events, and more.
The small things really do matter.
Let’s break down what makes them “stronger together” and “on the same wavelength.”
I think there’s got to be some correlation between the companies people start and the types of cofounders they become.
From a Vega document:
“The same exceptional people fuel both our careers and our personal lives – the people who matter cross both worlds.”
“We’re weaving the social fabric that will bring meaningful lives for everyone. Vega is the future of authentic relationships.”
Vega connects people. The cofounders know the importance of connection.
Of contributing to their community and restoring the village.
Most cofounders spend all their energy protecting the company from external threats. The best ones protect the relationship that holds the company together.
Here are some quotes from Madeline that show the strength of their connection.
“There’s nobody else I can imagine doing this with.”
“We’ve known each other for like 10 years.”
“We’re intellectual sparring partners.”
Their shared context (old memories, similar upbringing) gives them a kind of “mental shorthand.” They get each other.
They don't have to explain basic assumptions because they were formed in the same soil.
But don’t be fooled. Chemistry isn’t effortless.
They consciously overcommunicate, rather than assume.
They schedule monthly no-work meetings to check on each other’s lives.
They integrate their social lives and bring their friends together.
It gets even better…
Multiple times during our chat, Madeline struggled to explain why certain things between her and Ben worked so well. She resorted to “Idk, we’re just weird.”
At first, that might sound like a deflection.
But actually, it's the best explanation she could have given.
One of the most underrated truths about successful cofounders is that they develop a private world. A set of jokes, rhythms, ways of thinking that outsiders wouldn't immediately (or ever) understand.
Startups are weird by default.
If your partnership isn’t a little weird too, it probably won’t survive the real weirdness that comes later.
The best cofounder relationships aren’t perfectly polished.
They’re idiosyncratic. Specific. Slightly inexplicable.
Because they aren’t designed for the outside world’s approval.
And that's not an accident.
It’s weird — in the best way possible.
That’s all for now,
Tim He
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