July 29, 2026
Inbox roulette, but make it life-changing
The Cold Email
He gambled on awkward messages — and the comments are split between inspired and exhausted
TLDR: The writer says a few bold messages helped him get into college, land a career-changing job, and even buy into soccer teams. Commenters loved the confidence boost, but the real drama was over fake-sounding AI messages and whether cold outreach still works when everyone’s inbox feels spammed.
A founder-turned-investor just dropped a love letter to the cold email — those out-of-nowhere messages people send to strangers — and the internet immediately turned it into a debate about luck, persistence, and whether anyone can still sound human online. In the essay, he says three huge life twists started with bold outreach: getting off the waitlist at Carnegie Mellon, landing a job at GitHub after a nerve-racking email, and even ending up part-owner of soccer clubs after a direct message on Twitter. His big message? Just ask. Sometimes the answer changes your life.
But the comments were where the real fireworks started. One camp was fully onboard with the old-school pep talk, with one parent cheering the lesson that if someone already told you no, asking again might actually open a door. Another commenter popped in with a wholesome twist: they had met the author through a cold email themselves, basically serving as living proof that this stuff can work.
Then came the AI paranoia and inbox fatigue. One reader said they recently received a cold email, tried to engage, then bailed when the reply felt like fake "AI Voice" instead of a real person. Another, clearly battle-scarred, complained that inboxes are now flooded with cookie-cutter messages containing the same suspiciously polished sentence or paragraph every time. The funniest reaction? A reader expecting actual tips on writing cold emails got hit with a hockey-lottery mixed metaphor so chaotic it practically became the thread's unofficial meme. Moral of the story: people still love bold outreach — they just desperately want it to sound like a human wrote it.
Key Points
- •The author says an extra unsolicited submission after being waitlisted helped lead to admission at Carnegie Mellon University.
- •In 2010, the author responded to a Chris Wanstrath Twitter post and says the outreach led to a junior developer job at GitHub.
- •The article states that a cold Twitter DM later led to partial ownership in a soccer club and eventually involvement with another club in Serie A.
- •The author says many cold outreach attempts did not produce memorable outcomes, but the unsuccessful ones are harder to recall.
- •The article concludes that cold outreach can create opportunities when it is done sincerely and with genuine interest.