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Amy Cosper Unfiltered: Fear, AI, and the Brutal Truth About Starting Up

amy cosper
  • April 24, 2025
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From Me to You – A Conversation That Hits Different

You know those people in your life who are equal parts lightning bolt and truth serum? That’s Amy Cosper.

I had the absolute joy of sitting down with Amy- former Editor-in-Chief of Entrepreneur Magazine, a fearless rider (yes, motorcycles), and the brilliant mind behind The Ultimate Guide to Startups. We talked about what it really takes to reinvent, to find clarity in the chaos of launching something new, and why fear doesn’t get to drive the bike.

We also threw in some spicy AI fun, and hilariously bad business ideas. This one’s smart, raw, funny, and absolutely for anyone who’s ever stood at the edge of a big leap wondering if they were ready.

Spoiler: You are.

PS- I love how Amy just drops the f bomb! Also Shit gibbons (dying laughing!)

🎧 Hit play, and let’s level up—messy, honest, and all in.

  • Starr 💥

I don’t follow scripts. I help rewrite them.

For nearly three decades, I’ve worked with people and brands at pivotal moments- launches, pivots, reinventions, and second acts. The work blends strategy, story, positioning, and visibility into one integrated engine for growth and relevance.

Sometimes we build a breakout chapter. Sometimes we redesign the whole arc. Either way, the goal is the same: create something truer, stronger, and built to last.

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~ Private notes on reinvention, strategy, and building what's next.~