⚙️ Ops Playbook #88

The Silent Business Killer You're Probably Ignoring

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⚙️ Hi Operator,

I Think We're Onto Something Here...

Hey operators,

Last week, I asked what you valued more - templates or talking to people - and a whopping 72% of you chose templates and playbooks over traditional community features.

Reading through your comments, I noticed something fascinating emerging. Many of you want real-world operational resources that come with context and the stories behind them:

or like how one reader said:

It's like you're collectively pointing toward something that isn't just a template library or just a community, but something in between - where the real value is in operational resources created by people who've actually used them.

I recently came across Reforge's "Artifacts" program which does something similar for product and marketing professionals. They've built a library where product managers share real work documents along with detailed notes about how they were used.

What if we created something like this specifically for operations? A library of real operational documents with the stories and context behind them - created by all of us, for all of us.

Here's what I'm wondering:

Would you be willing to contribute to an "Operator Library" of real operational documents?

Please comment too if you vote!

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If you answered Yes or Maybe, I'd love to hear: What specific operational document, template, or process would you be willing to share? Hit reply and tell me about it!

Some examples might be:

  • An onboarding process you developed

  • A vendor evaluation framework

  • A cross-functional project management template

  • A team restructuring plan

  • Something else entirely?

This is all about exploring what we could build together. Your input will help shape where we go from here.

- Rameel 

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The Silent Business Killer You're Probably Ignoring

Look, nobody starts a company dreaming about quarterly tax filings. Yet how you handle this unsexy operational necessity reveals volumes about your business maturity.

The Real Numbers Are Ugly

Here's what keeps me up at night: 40% of growing businesses get slapped with payroll tax penalties annually. We're talking $1,000 per incident on average – and I've seen much worse. Just think about it: a grand disappearing into thin air because someone clicked the wrong box on a form or didn't realize their "contractor" legally counts as an employee.

And that's just the beginning. Watch the dominoes fall: leadership time spent fixing mistakes, cash flow disruptions, and explaining to your team why payroll might be delayed because you're sorting out an IRS issue.

The Three Compliance Layers Nobody Talks About

  • Federal Layer: Let's start with the basics. Form 941 filings each quarter, FICA deposits (6.2% Social Security, 1.45% Medicare), and managing FUTA tax. Get this wrong and the IRS becomes your least favorite pen pal.

  • State Layer: Welcome to the chaos. Each state has its own withholding rules, unemployment insurance systems, and workers' comp requirements. California alone will make you question your life choices.

  • Local Layer: This is where it gets messy. Cities, school districts, and transportation authorities creating their own tax kingdoms. Philadelphia, NYC, and San Francisco are particularly creative in finding ways to extract revenue from your business.

What To Do Tomorrow

  1. Build your compliance calendar – Know every deadline across every jurisdiction

  2. Do a classification audit – Contractor vs. employee mistakes are the fastest way to penalties

  3. Document everything – The IRS wants four years of records; smart businesses keep seven

  4. Automate what burns time – Manual compliance work scales horribly

Look, I get it. Compliance work ranks somewhere between watching paint dry and organizing your sock drawer.

But you know what's worse?

Standing in front of your exec team, explaining why you're hemorrhaging cash on penalties you could have avoided with a decent spreadsheet and a calendar reminder.

The best operators I know have turned this tedious necessity into their secret weapon. Because when everyone else is scrambling to fix mistakes, they're focused on growing their business.

P.S. Let me know what you thought of today’s piece! Reply to this email or tell me here!

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