Cold Emails Changed His Life — And the Survivorship Bias He Owns Up To

Zach Holman credits cold outreach for three pivotal turns in his life: an extra essay mailed overnight that pulled him off Carnegie Mellon’s waitlist (which clears only 1–10% of candidates), an intimidating email answering Chris Wanstrath’s 2010 tweet looking for junior Ruby developers that landed him a job at a then-cliquey, barely-solvent GitHub, and a single cold Twitter DM that eventually made him a part-owner of soccer clubs and reshaped his career around sports and tech.

He preempts the obvious objection — that this is pure survivorship bias — by conceding it outright. For every message that changed his life, he sent countless others that went nowhere and that he no longer even remembers. His point isn’t that cold outreach reliably works, but that you can’t win a bet you never place, so it’s worth the occasional awkwardness to reach out. The one condition: be genuine and actually interested in the other person, because recipients (himself included) can spot a transactional pitch instantly.

The closing argument shifts to the other side of the exchange. Holman says he’d always accept cold resumes and pitches at any company he ran, and points to his own habit of investing in founders he had no prior connection to, as a way of paying forward the breaks he got and of widening his own network and blind spots. Today’s sender is tomorrow’s recipient, so the practical takeaway is to reach out with restraint and good faith — and to be the kind of person who says yes when someone reaches out to you.