Zach Holman’s first big win from cold outreach was getting off Carnegie Mellon’s waitlist. His dad encouraged him to overnight an extra essay detailing his work on Good-Tutorials, then the internet’s largest tutorial site, plus other materials about his senior year. A few days later he got in—CMU only admits about 1–10 percent of waitlisted students—so that extra push mattered. In 2010, Holman spotted a tweet from GitHub cofounder Chris Wanstrath looking for junior Ruby developers. He admitted he barely knew Java but shot off a bold email anyway. They met at Hotel Utah and hired him on the spot for a $60k junior role—low risk for a cash-strapped startup. Six years ago, a cold Twitter DM landed him part-ownership in a soccer club. That led to another stake in a Serie A team and steered his career toward sports tech investments and volunteer work. He can’t name the cold emails that failed—only the ones that changed his life. That selective memory, he argues, shouldn’t scare you off. Cold outreach is awkward but necessary. Do your homework, show genuine interest, and don’t treat it like a numbers game. Holman also underscores how recipients benefit. He vows to read any cold resume or pitch he gets, since others did the same for him. Opening doors for strangers expands networks and breaks blind spots. So when it feels right, reach out—and be ready to pass the favor on.