Jonathan Stern

Talk to your heroes

One of my favorite pastimes is cold-calling and emailing my heroes.

  1. When I was first looking for a job, I called the office of Leon Cooperman, billionaire hedge funder at Omega Advisors. The receptionist answered: “Hello, this is Omega. How can I help you?” To which I replied: “Is Mr. Cooperman available?” Seconds later, I hear the telephone wires of the landline getting shuffled around... Cooperman picks up! I was stunned. Never in a million years did I expect to get transferred to Cooperman himself. My heart about to pop out of my chest, all I could muster was: “Mr. Cooperman! Any chance you’re hiring?” He shot back with that unmistakable, gruff New York voice I’d heard a million times on CNBC: “Son, you should know better than calling an office like this asking for a job. Please don’t call back!”

  2. Years later, feeling inspired while walking past the Sam Adams statue outside Faneuil Hall, I decided to call historian David McCullough. A few weeks prior, I'd found a number on White Pages and wanted to give it a try. What was the worst that could happen, I thought. Incredibly, he answered. The voice from Ken Burns’ Civil War series—one of the most recognizable voices of our time—was on the other end of my phone! Unlike when I called Cooperman, I knew exactly what I wanted to say: In Boston, we have hundreds of gorgeous statues around town. A few have small plaques, but most have nothing explaining to the public who these people were. I wanted McCullough’s help writing a blurb that we could add to each statue. Sadly - nothing ever came of the project... but I'll never forget pitching my idea to David McCullough one morning on my walk to work.

  3. After Sam Altman wrote “How To Be Successful,” I marked up the essay with dozens of reflections and wanted to get Sam's thoughts. I didn’t know how to get in touch with him, so I friend-requested Sam on Facebook. He accepted! I DM’d Sam and we had a wonderful chat on Facebook Messenger.

  4. I used to spend most of my free time building a debate platform called Pairagraph. Over the years I sent more than 2,000 emails to distinguished people asking if they’d like to participate. We hosted more than 100 dialogues featuring billionaires, politicians, religious leaders, Nobel prize winners, and more. All it took was a thoughtful email asking if they’d like to take part.

  5. A week before I started my current job as a software engineer, I emailed Replit CEO, Amjad Masad, asking for advice. His response was enormously helpful.

In previous eras, there wasn't a good way to contact the most powerful people in society. Today, everyone is an email away. When you reach out, be concise. Be compelling. Always have something interesting to say. And make sure you have a specific reason or question in mind. Other than that - just have fun. It is fun beyond belief to chat with your heroes.