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Rough Terrain

Cyril Sack

Thoughts on tech disruption and innovation, organizational leadership, product strategy, and why tacos and margaritas are the best

PricingOnly free issuesPublishesWeekly

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Latest Issues

Recent posts by this newsletter. Browse the email archive.

How to get better at hiring

Hiring is the most important thing you can do as a manager. Hell, as an IC as well. There is nothing, absolutely nothing as impactful to the success of an organization as the quality of the people in it. Underneath every cool product or nov...

a month ago

The Dangers of “Heroic Leadership”

Let me tell you about Iron Mike. Iron Mike is a famous statue of an American soldier you can find at various US military installations and battlefields across the world. He is a symbol of toughness, resilience, courage, and pretty much all ...

10 months ago

The Rule of Cy

Howdy folks, been a few months. I’d offer excuses but (a) there’s like 25 of you, (b) this substack is and will always be a tool for helping me find clarity of thought before it is an actual newsletter for readers, and (c) it’s free so shut...

a year ago

Should transitioning veterans pursue education or certifications before entering the civilian workforce?

Before we hop into the latest edition, I want to say my heart goes out to all my friends at Flexport impacted by the recent layoffs. My team and surrounding stakeholders were hit hard. This has made this week extremely bittersweet, as it’s ...

a year ago

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The writers behind this newsletter.

  • Cyril Sack

    Husband, Dad, occasional enjoyer of strenuous things, loves a good taco. more

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