Working
with Billy
You don't get ahead here by being impressive. You get ahead by being the person Billy never has to think about twice.
Start here
Twelve minutes now saves you a month of guessing.
This manual exists because Billy answers the same six questions in every new hire's first month. Read it once and you skip that queue.
It covers how he decides, how he wants to be told things, what the week looks like, and what "done" means here. It is deliberately short. Anything that needed a paragraph we cut, because a manual nobody finishes is a manual that doesn't work.
Two rules about the rules. First: if Billy says something in the moment that contradicts this page, Billy wins — then tell him this page is wrong so it gets fixed. Second: nothing here is a substitute for a number. This document tells you how to behave; it can't tell you whether the deal is real.
Find something worth selling, prove it's worth selling, and tell Billy before he has to ask.
The 30-second version
Three things to understand before anything else.
The company
A small shop that finds content worth watching and turns it into revenue. Short feedback loops, no committees, no waiting for permission you already have.
The person
Billy is the founder-operator. He replies fast, decides faster, and remembers exactly what you said you'd do. That last part is the whole relationship.
What winning is
Revenue you can point at, work he doesn't have to redo, and zero surprises. In that order — but if you only get one, get the third.
What does not count as winning: a busy week, a long list of people who "seemed interested," a beautiful deck nobody asked for, or anything described mainly with adjectives.
How Billy works
Six rules, in the order he escalates. Rule 1 is the one he cares about most.
Bring the answer, not the question
Never hand Billy a problem and wait. Bring the recommendation, the reason, the worst case, and what you need from him — in that order. He'll overrule you happily. He will not do your thinking for you.
Not: "The client went quiet, what should I do?" → Instead: "Silent 9 days. I'm sending a two-line nudge today, calling Thursday if nothing. Fine?"Speed first, polish second
A rough thing today beats a perfect thing next week. Send the draft, label it a draft, and say what's still missing. He would rather correct your direction on Tuesday than admire your execution on Friday.
Label it: "v1 — rough, the pricing logic is still a guess."Numbers beat adjectives
Every update is a quantity, not a feeling. Dials, replies, conversations, meetings booked, deals moved. If you can't count it, say what you'd count if you could.
Not: "Good activity this week." → Instead: "38 dials, 6 conversations, 2 booked for Thursday."Close the loop or it didn't happen
Every ask ends with an owner and a date. Every promise gets done, rescheduled in writing, or explicitly dropped. An open loop is the only thing that actually annoys him.
The habit: end messages with "— yours by Thu 5pm" or "— I need this from you by Wed."Say the bad news early and plainly
Lost deal, missed number, angry client — first line, no preamble, no sandwich. He can work with bad news he hears on Monday morning. He can't work with bad news he discovers on Friday afternoon.
Open with it: "We lost the Riverside deal. Here's why, and what I'd change."Don't ask the same thing twice
If you had to ask, write the answer down where you'll find it again — a doc, a template, this manual. Repeat questions are how smart people quietly lose trust.
Test: could a new hire answer this from what's already written down?The communication contract
Pick the channel by what you need back, not by what's open on your screen.
| Channel | Use it for | Expected reply |
|---|---|---|
| Slack DM | Anything blocking you. One message, with the ask in the first line. | Same day, usually within a couple of hours |
| Slack #wins | Booked meetings, closed deals, client praise. Receipts, not commentary. | Reactions only — no reply needed |
| Anything a client or partner might forward, or anything that needs a paper trail. | Next business morning | |
| Loom / video | Anything visual, or longer than five lines of text. Show the screen. | Watched within a day; reply is a decision, not a note |
| Phone | Bad news, a deal at risk, or anything with a heartbeat and a deadline. | Answered, or called back same day |
| The weekly doc | The full picture: numbers, pipeline, what you need. Everything else is a footnote to this. | Read before Monday's call |
One ask per message. First line is the ask or the headline. Details after. If a message needs a scroll to find the point, rewrite it.
No "circling back," no "just bumping this," no "quick question" that isn't quick. Say the thing.
The weekly rhythm
Three checkpoints. Miss one and the next one costs twice as much.
The plan
- Three numbers you're committing to for the week
- One bet: the thing you're doing that isn't obvious
- Anything you need from Billy, decided live
- Rule: no plan, no meeting — send it before
The pipeline
- Every live deal, one line each, with a next step and a date
- The deal most likely to die, said out loud
- What changed since Monday, and why
- Rule: a deal with no next date is not a deal
The scorecard
- Committed vs. delivered, side by side, no spin
- What you learned that changes next week
- One thing to fix in the process
- Rule: sent by 4pm Friday, in writing
Everything else in the week is yours to run. Billy doesn't want a running commentary — he wants to be able to open one document and know exactly where things stand without calling you.
Your first 30 days
Check things off. The bar for week four is simple: nobody has to check on you.
Learn the machine
Do it badly, in public
Own a number
Stop needing a babysitter
The quality bar
Run this list before anything goes to a client — or to Billy.
The 10-second test
Can someone read the first two lines and know what you want, what it costs, and what happens next? If not, the rest doesn't matter.
Receipts
Every number has a source. Every claim about a client traces to something they said or wrote. No rounding up, no "roughly," no vibes.
Names and links
Company spelled the way they spell it. Person's name right. Every link opens, every attachment is attached, every date has a day of the week.
The redo test
Would Billy have to rebuild this, or just approve it? Rebuilding is the expensive kind of mistake — it costs his attention, not your time.
One ask
If the document asks for three decisions, it will get zero. Split it, or lead with the one that unblocks everything else.
Say what's missing
A gap you named is a plan. A gap you hid is a surprise. Same gap, completely different outcome.
When to escalate
Work down this ladder in order. Most things stop at step one.
-
Ask the written thing
This manual, the docs, the last thread where it was decided. If the answer exists, using it is faster than asking for it.
-
Ask a teammate
Anyone who's been here longer than you. They'd rather answer for two minutes than watch you spin for two hours.
-
Ask Billy — with a recommendation
One message: the situation, your call, the risk, the decision you need. If he can reply "yes" or "no," you did it right.
-
Call, don't type
Reserved for two cases: a live deal is about to turn, or a client is upset right now. Two hours with no reply on either of those is your cue to dial. Nobody has ever been in trouble for calling too early on a real fire.
Do / don't
The short version, for the days you don't have twelve minutes.
Do
- Send the draft today and mark what's unfinished
- Put the ask in the first line
- Give bad news a timestamp, not a story
- Write it down the first time you learn it
- Bring one idea a week nobody asked for
- Ask for the decision you actually need
Don't
- Wait for a perfect version that ships next month
- Bury the point under three paragraphs of context
- Say "circling back" when you mean "I forgot"
- Ask a question that's already answered in writing
- Report activity when you were asked for results
- Surprise him on a Friday afternoon
Words we use precisely
Loose language is how pipeline gets inflated and trust gets spent.
- A lead
- A company or person who fits the profile. No interest required yet.
- A conversation
- A live, two-way exchange with a decision-maker. A voicemail is not a conversation.
- Booked
- On a calendar, with a name and a time, that the other person confirmed. "Wants to talk soon" is not booked.
- Qualified
- Problem, budget, authority and a timeline — all four named out loud by them, not inferred by you.
- At risk
- Something changed and you know what it was. If you're guessing, it's not at risk, it's unknown.
- Next step
- A specific action, a specific person, a specific date. "Follow up" is not a next step.
- Done
- Delivered, in the hands of the person who asked, and confirmed received. Sent is not done.
- Surprise
- Anything Billy learns after the point where he could have helped. The only unforgivable category.
Keep this current
A manual nobody edits is a manual nobody trusts.
If a page here is wrong, out of date, or missing the thing you had to learn the hard way, say so in the weekly doc. One line is enough: "Section 03 is wrong because ___." Changes get made weekly, not annually.
The version you're reading is Edition 01. Everything in it was true when it was written — assume the parts about tools and channels will move first.
| Edition | Date | What changed |
|---|---|---|
| 01 | October 2026 | First edition. Written for the first cohort of new hires. |
| 02 | — | Your name goes here. |