Systems & Side-eyes
Katie Barnes, Juan Salas-Romer, Alex Randall Kittredge, John BrewtonA field guide for cleaning up chaos, building smarter systems, and surviving early-stage silliness with your integrity intact.
| Platform |  | Pricing | Freemium | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 55 | Founded | a year ago | Last Issue | 4 days ago |
| Active | |||||
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You're Not the Bottleneck. You're the Proof It Worked.
It’s 11pm.
You’ve been ON since 7am. Founder-led sales, or pitching the raise, or both, and you’ve finally got a minute to look at the actual work. The thing you’re supposedly running.
Ten Slack messages. All variations of the same questi...
The Hidden Taxes Inside Messy Startups
The costs founders are paying long before they show up in a financial model.
You are leaky…
Some Career Lessons I Apparently Needed to Learn 14 Different Times
I didn’t build my career through some perfectly mapped-out plan. (Which is actually kind of surprising, seeing as I try to help others map out this plan as a career.)
I ultimately arrived here by getting dropped into messy situations and f...
Lead with Empathy. Always.
Hello, my friends. I know I am days late on a drop for you. (I am sure you’ve been on the edge of your seat.) Unfortunately, I’ve been posted up in the hospital since last weekend.
My grandma was in the ICU. As the eldest grandchild, I was...
The questions I ask before I blindly believe a new founder...
Founders tell me the problem.
I don’t believe them.
(Not yet.)
Most of the time… they haven’t talked to the people doing the work.
I hear it allll the time in my discovery and kick off calls: “The team isn’t moving fast enough.”
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| Subscribers | Engagement | 77 | Monthly Web Visits | ||
|---|---|---|---|---|---|
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Authors
The writers behind this newsletter.
Ops guidance for founders tired of duct-taping their way to growth. One weekly clarity drop to help you scale smarter. (with a side-eye \ud83d\udc40 and a system.)
4x Founder, $35M exits. Coaching 100+ subs. I help people and organizations navigate AI-driven change.
I help technical CEOs go from 0 to 10, translating complex organizational challenges into strategic clarity, grounded in data, history, and human insight. Get one piece each week providing portfolio career strategy for a post-AI economy.
WE ARE ALL BECOMING COMPANIES. I help you build yours. Built a company to +$50M and sold it. Built audience of +50,000 so far…Harvard economics nerd writing about the future of operating companies.
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