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The author shares three pivotal stories—from getting off a university waitlist to landing a GitHub job and owning a soccer club—to show how unsolicited outreach opened doors. He admits most cold emails go nowhere but argues the handful that work make it worth trying, as long as you’re genuine and respectful. He also pledges to keep his inbox open to pay it forward.
- CMU only admits 1–10% of waitlisted students, but an unsolicited extra essay from Holman got him in
- A bold cold email to GitHub's cofounder led to an on-the-spot hire, since a $60k junior role was low risk for the startup
- A cold Twitter DM turned into part-ownership of a soccer club, which later led to a stake in a Serie A team
- He only remembers the cold outreach attempts that worked, not the ones that failed, so survivorship bias shouldn't discourage trying