What I Learned from Jim Mattis’s Former Speechwriter About Communications

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On this week's podcast I spoke with Justin Mikolay. Justin is a former speechwriter. He has written for Jim Mattis, General David Petraeus, and Leon Panetta. He has worked as an evangelist for Palantir and held the role of Director of Communications for the Secretary of Defense. Currently, he works at Gumroad and has a newsletter summarizing the big ideas of the biggest names on Twitter:

Here are some of my takeaways from the episode:

Working on a Submarine

Before Justin worked in communications, he was a junior officer on a submarine. Working on a submarine is not for the faint of heart. You live and work in close quarters, sometimes not seeing daylight for months. On the submarine, Justin was required to understand everyone’s roles and responsibilities. So even if his specialty is engineering, he still needs to understand the basics of medicine. Working undersea for months at a time allowed Justin to pursue writing in his spare time. This would set him up for the rest of his career.

Writing for Someone Else

One of the challenges for many of the communication professionals out there is capturing the brand's voice. When you create content for a brand, you have to write from the brand's perspective — align with their voice and style. Five years into his Navy career, General David Petraeus hand selected him as his speechwriter. He needed to learn how to inhabit the General's brain. He read his previous speeches and adapted to his style. For example, General Petraeus is grammar obsessed. Every speech must follow the principles of Strunk an White. General Petraeus expected perfection from the mechanical and elemental side. Justin recalled this one story from General Petraeus about perfection:

"Let me tell you a story. It comes from the experience of an American painter, Samuel F.B. Morse, who wanted to become a master painter. So he went to London to study painting under a noted British master at the time. And the master painter told Morse to do the very best painting he could and show it to him. Morse went off, worked hard on his painting, and took it to the master painter, but the master said, “Before you show it to me, can you make it any better?” Morse said yes and went back to work. He noticed a few blemishes, and changed a whole section of the painting. He took it back to the master painter, but again the master said, “Before you show it to me, can you make it any better?” This went on several more times and Morse became more and more frustrated. But every time he worked on the painting he found something to improve, even if it was a minor detail, and by the time he showed it to the master it was nearly a masterpiece."

Moving to the Private Sector

After working with General Petraeus, Justin wrote for Leon Panetta and Jim Mattis. While speechwriting taught him a lot, he didn't have a chance to write on his own. One of the effects of being in government is gunshyness — you don't really express your personal opinion. He began to finally express his opinion online and started to publicly write. His first major content breakthrough came from his time in government. Justin spent a lot of his time being immersed in the brains of the people he worked for. He decided to turn that into a newsletter. He would look at what prolific people would tweet and summarize these tweets. His first profile was of David Perell. His tweet announcing the summary received 1.5K likes and 300RTs. He found content that resonated with people. After his first success, he wrote more summaries. He then messaged Sahil Lavingia, CEO of Gumroad, about working there. Sahil replied with two questions:

  1. "What can you do?"

  2. "Prove that you can do it?"

Justin replied with the summaries he created including a summary of Sahil's work. Justin was then hired part time writing content for Gumroad. His work at Gumroad, similar to the work he is doing for his essay.

My biggest lesson from the interview is building your own content and social helps set you up for success in your day job.

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