The Wednesday Play: Shoot Your Shot

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Hi Playmakers!

At 17, I cold emailed a billionaire and asked him to pay for my college.

He said yes.

That one message changed everything — and taught me something I’ve carried with me ever since:

A cold email isn’t just an ask. It’s a door.

Since then, I’ve used cold emails to land jobs in Silicon Valley, get featured on Good Morning America, book A-list speakers, and launch partnerships with celebrities. I didn’t have connections or credentials — just a “Why not me?” attitude and a willingness to hit send.

Here are the top tips I’ve developed for how to write cold emails that actually work: