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A field guide for cleaning up chaos, building smarter systems, and surviving early-stage silliness with your integrity intact.

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Substack
PricingFreemiumPublishesWeekly
Issues65Foundeda year agoLast Issue5 days ago
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systems.riseandoptimize.com
Artwork for Systems & Side-eyes

Latest Issues

The Operator's Back Room #001 - The Startup Operating Rhythm

If every question still ends up tagging the founder, you don't have a meeting problem. You have a communication rhythm problem. Here's the operating cadence I use to get growing teams out of that cycle.

👀 What you’ll leave with

5 days ago
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Two Kinds of People Read This Newsletter

I started this newsletter to write about what actually happens behind the curtain of growing companies.

Not the highlight reel.

The actual, messy, three-Slack-threads-deep reality of it. I am incredibly grateful that there are over 4,800...

11 days ago
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One Year Without a W2: What I Got Wrong, What I'd Say Again

One year ago, I quit being a W2.

I sat in my car after my last day and thought: cool, now I just have to convince strangers to pay me for the thing I’ve been doing inside other people’s companies for 14 years. No pressure

.

A year later,...

18 days ago
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AI Didn't Make You Dumber. It Made You Absent.

TLDR: Founders aren't using AI wrong because they're using it too much. They're using it wrong because they stopped showing up for the decisions underneath it. You can use AI AND still be the one doing the thinking. Right now, most people a...

24 days ago
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For the "I have way too many meetings..." people

TLDR: Founders cut meetings. Nothing changes. That’s because the meeting was never the problem; it was covering for missing decision ownership, unclear roles, and a founder who has to be in every room for anything to move. This one is about...

a month ago
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Authors

The writers behind this newsletter.

  • Katie Barnes

    For founders living the chaos and operators cleaning it up. Startup systems, founder psychology, practical tools, and the occasional side-eye.

  • Shannon Bindler

    Half psychology, half cosmic wink. Naming the patterns you’ve been sensing.

  • Juan Salas-Romer

    4x Founder, $35M exits. Babson & BC entrepreneurship and finance MBA degrees. I help non-tech founders build AI-powered businesses that earn more, serve clients better and free up their time.

  • Alex Randall Kittredge

    Strategy consultant to technical founders; built my career across a $20B family office, fintech startup, intelligence work, and my own firm. I write ARK Strategy: portfolio careers for the post-AI economy. Careers aren't ladders — they're portfolios.

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