What Entrepreneurs Can Learn from Running Remote
Maria closed her first office lease six months before her third hire quit, citing a two-hour commute and a toddler at home. She replaced the lease with a laptop budget and called the company remote. In practice nothing changed: interviews happened as before, new hires got a login and a wish of good luck, and Maria still judged people by how fast they answered messages. Two more good hires left within a year, each citing the same thing: nobody had rebuilt how the company worked, they had only removed the room. Maria began to suspect that calling a company remote and running it as one were different projects.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Hiring your first team without an office to lean on
Founders often hire remotely by simply skipping the office step, without redesigning what comes before and after the offer. A remote-first process treats the interview as a work sample, tests written communication as heavily as skills, and gives new hires a structured first month instead of a login and good wishes. Built early, this becomes the company's default rather than an exception grafted on once far more habits would need to change.
Founders hire on a good video call and charisma, then discover months later the person cannot work independently or write clearly.
Build a short written work sample into every interview, and pair each new hire with a thirty-day plan of named deliverables, not a list of logins.
Measuring progress by results, not hours at a desk
Early founders often equate long hours with commitment, then unconsciously expect the same from hires. A healthier default sets clear, agreed outcomes for each role and week, then evaluates against those rather than visible activity or reply speed. This protects trust as the team grows past people you see daily, and stops you rewarding the appearance of busyness over work that moves the company forward.
A founder starts eyeing who is online late and who replies fastest, quietly building a culture that rewards presence over output.
Set two or three concrete deliverables per person each week, review those in a short check-in, and drop any talk of hours or online status.
Building a culture before you have a headquarters
Culture in a scattered founding team does not form by accident the way it might around a shared kitchen. It has to be named and repeated: shared language for decisions, regular non-work conversation, and visible recognition of the values you claim to hold. Skipping this because the team feels close already is a common mistake, since the habits set now either scale gracefully or dissolve once the company doubles in size.
Everyone assumes the tight-knit vibe of the first five hires will simply continue, and it evaporates once hire ten joins a company that never wrote its values down.
Write down three behaviors the company already does well, and build one recurring ritual, such as a weekly show-and-tell, that makes them visible.
Decisions and documentation that scale past the founding team
Habits a founder keeps informally, like verbal decisions and undocumented context, work at five people and break at fifteen. Lightweight documentation and decision records built early let new hires onboard themselves instead of interrupting you, and let decisions survive turnover instead of vanishing with whoever made them. This habit, more than any tool, decides whether growth feels like momentum or chaos.
A founder under deadline pressure often reverts to quick verbal decisions and skips documentation, exactly when the company needs a paper trail most. Culture rituals feel like a luxury during a crunch, yet skipping them in the hardest months is when their absence is felt most, since stressed teams need connection more than relaxed ones. There is rarely time to do all four well at once, so founders must choose deliberately rather than let urgency pick for them.
Name one thing, honestly
Which of these four areas have you built deliberately, and which have simply happened by default? What would change if every new hire could fully onboard themselves using only what is written down?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Write down three behaviors the company already does well, and build one recurring ritual, such as a weekly show-and-tell, that makes them visible.