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Hi {{first_name}},
There’s a distinction most business owners can quote from memory: working in the business versus working on it. Michael Gerber made it famous in The E-Myth. Working in is doing the work. Working on is building the machine that does the work.
I knew that framework in year one of my first company. I could have taught a seminar on it. It still took me six years to actually live it, and the gap between knowing and living is what this letter is about.
Working in the business never announces itself as a problem, and that’s what makes it dangerous. It announces itself as being indispensable. In my case it wasn’t one job. It was all of them at once. Every new initiative, every marketing push, every piece of innovation started at my desk, and so did the unglamorous work nobody puts on LinkedIn: chasing receivables, watching the cash balance to make sure payroll cleared. Every one of those facts felt like evidence I was doing my job. They were actually evidence I had built a company that couldn’t function without me, which is another way of saying I had built myself a job with extra steps.
The tell was simple, and I ignored it for years: the business only grew when I personally pushed it forward. The company had no momentum of its own. It had mine, on loan, renewed daily.
What finally moved me wasn’t a single insight. It was exhaustion, and one blunt admission somewhere in year six: me doing it isn’t working. What if somebody else did it? That question, asked honestly, reorganizes everything. I started hiring people who were better than me at marketing, better at operations, better at the things I had been white-knuckling for years, and the unlocks came fast. Hiring stops being about helpers and starts being about owners of outcomes. Documentation stops being busywork and becomes the machine’s source code. Delegation stops feeling like risk and starts feeling like construction.
The math underneath is the part I wish someone had made me stare at in year one. Time in the business is linear: an hour of selling yields an hour of sales, and tomorrow demands the same hour again. Time on the business compounds: an hour spent hiring the right manager yields years of decisions that never reach your desk. Same hour, radically different return profile. Most owners allocate ninety percent of their week to the linear asset and wonder why the compounding never shows up.
I’ll be honest about the other side too: some working-in never goes away, and shouldn’t. The founder who never touches the product or talks to a customer is working on a rumor. The goal isn’t zero. It’s intentionality, choosing your in-the-business hours for what they teach you, not because the calendar defaulted to them.
This connects to the NADA test from a couple of weeks ago. Nix, automate, delegate, act is the mechanism. Working on the business is what the mechanism buys you. Run the filter ruthlessly enough and what’s left in the act column is, almost by definition, on-the-business work.
The exercise this week: pull up last week’s calendar and mark every block In or On. No judgment on the ratio, most owners start somewhere around 90/10. Just measure it. What gets measured gets moved.
Talk soon,
Matt
P.S. When I’m not writing this, I’m buying and operating founder-led businesses for the long term at Eidolon Capital. If you’re a founder thinking about your next chapter, or you advise one who is, just hit reply. I read every note.