The one person who knows how it works
Tim on the one person at every company who quietly holds a process together — and why protecting their vacation isn't the same as fixing the problem.
· 2 min read
Thoughts
Building things on the internet — apps, experiments, and what they taught me.
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Due Diligence: The Questions You Didn't Prep For
The pitch isn't the goal — getting into due diligence is. And due diligence means investors will find the thing you didn't mention, because someone else will mention it for you.
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Speak to the Room, Not the Expert
Most investors in the room won't know your industry, so build your pitch for the majority who don't — and find the one person who can tell you who's who before you start.
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Most of what I've documented was for me
Tim on writing SOPs nobody opens — and the slow realization that a lot of documentation is really the writer figuring something out, not a reference for anyone else.
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The Meeting Booked For Thirty, Done In Four
Tim on booking meetings for thirty minutes because that's what the calendar defaults to, and what happens to a conversation when you don't touch the dropdown.
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The One Pager: What Survives When You're Not in the Room
Your pitch deck earns the meeting, but the one pager is what gets forwarded to the partner who wasn't there — so it has to work with zero context, no charm, and no you explaining it.
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We Bought the Tool to Skip the Conversation
Tim on the project tracker he pushed the team to buy — and the honest reason he wanted it, which had nothing to do with visibility.
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The Story Isn't About You (Even If You're In It)
A pitch deck story should center on the problem and the solution, not the founder's personal journey — investors remember the narrative, but only if it's the audience's story, not a memoir.
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When someone calls in sick, I never check
Tim has never asked for a doctor's note. He trusts by default. What he's still bad at is noticing the moment that trust gets broken, because trusting gives him no early warning.
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Next Steps: Milestones That Depend on the Round Closing
A milestones slide should be a $X-to-build-Y-in-time-Z accountability statement, not a chain of events that all quietly assume the round closes first.
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When Everyone Skips the Process, Fix the Process
Tim on the process nobody follows: when the whole team routes around a documented step, his instinct isn't to enforce it — it's to assume the process is wrong.
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Why Every Financial Slide Looks the Same
Financial slides fail when every assumption is the best-case scenario. Investors don't expect accurate numbers — they expect numbers that make sense, so the growth rate has to look believable, not perfect.
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I Said Great Job And Meant Nothing By It
Tim thinks specific praise given late beats generic praise given immediately, even though he still defaults to the fast generic version out of habit.
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The Team Slide's Silent Advisor Problem
Investors don't care who your advisors are unless they've invested money or fill a critical missing skill — padding the team slide with names for credibility backfires.
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Expensive Money: Why "0% Interest" Rarely Is
Investor money, like store financing, often looks free upfront but costs far more than a loan once you run the actual math on equity given away.
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Confidently Wrong About the Bottleneck
Tim on being the person called in to find where the work is stuck — and how often the flowchart pointed at the wrong thing because the real jam was a person, not a process.
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The Problem Slide: Make Investors Feel It, Not Just Read It
A pitch deck's problem slide fails when it states a fact instead of building the pain — investors need to feel the cost, not just acknowledge it exists.
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The question I was embarrassed to ask
Tim on being the least experienced person in the room — the question he was too embarrassed to ask was usually the one three other people were hoping someone would.
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I Get the Answer and Lose the Person
Tim Cooley on his tendency to push for the answer before someone is ready to give it — and what he loses when he wins that exchange.
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The Champion Who Leaves in March
A champion investor is a person, not a permanent asset — if they leave the firm before your round closes, their vouching leaves with them, so move fast and confirm they still have standing.
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The Angel Who Says Yes and Never Wires
Not every angel investor who says "yes" is actually going to send money — the real yes depends on who they are and how they made their fortune. Learn to tell the difference before you count the cash.
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The Real Meeting Happens After the Meeting
Tim on the leadership meeting that agreed on a plan in eleven minutes flat — and the real conversation that happened afterward, in a smaller room, without him stopping it.
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Asking for Money: Why Timing Beats Need
Investors, like lenders, fund confidence and momentum, not desperation. The lesson from Tim Cooley's pitch deck book: raise money when you're winning, not when you're running out of runway.
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Hiring Someone Better Than Me at My Job
Tim on the day he hired someone sharper than him at his own job — what he felt on day one, that it wasn't good, and how it passed.
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I Signaled My Disagreement and It Backfired
Tim tried delivering a decision he opposed by quietly letting his team know he opposed it too — and it undermined the whole rollout. He still isn't sure where honesty ends and undermining starts.
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The One Liner: Say What It Is, Not What It Isn't
Investors don't fund what your business isn't. Your one-liner needs to state what your business is, in plain words, in under 12 seconds.
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The Elevator Pitch Doesn't Close Anything
The elevator pitch isn't meant to close a deal — its only job is to earn the next question. Confusing the two is why so many one-liners fall flat.
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I Said It Was Wrong, Right There in the Room
Tim says it in the room when a peer is wrong, not after — it has cost him, and he is still working on making it land as logic instead of emotion.
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The Quiet Account I Never Called
Tim on the customer who never complained, never called, and then just left — and why he mistook that silence for health for far too long.
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The Pitch's Only Job Is the Next Meeting
A pitch doesn't get you funded — it gets you a second conversation. Funding happens after due diligence, not in the room, so the pitch's only real job is earning the next meeting.
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Nobody Reads the Guide, Including Me
Tim spent two years blaming customers for not reading the onboarding guide before he admitted the guide was the problem, not them.
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The Billboard Rule for Pitch Deck Font Size
Test your pitch deck's font size and colors in the actual room you'll present in, not on your laptop — what reads fine up close often disappears from the back of the room.
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Why Your Pitch Deck Needs Zero Design Skills
Investors don't fund your slide design, they fund your story — free stock photos are enough for most pitch decks, unless your product's whole value is the brand itself.
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The Label Isn't the Expensive Part
Tim on the support-vs-product standoff over what counts as a bug: if the customer thinks it's broken, the argument about the correct label is the part that actually costs money.
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Note Cards Kill Your Pitch Credibility
Investors read confidence, not content — note cards signal you don't fully know your own business, and once nerves hit, founders start reading them word for word instead of pitching.
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The Customer I Let Go
Tim on the one time he fired a customer — it wasn't about the money, it was about not being able to help them, and he still isn't sure he read it right.
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The Customer Who Loves Us Won't Upgrade
Tim on the customer who renews, refers people, and never buys more — and the mistake of reading affection as a budget signal.
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Why Pitching Faster Never Fills a Quiet Room
Nervous founders speed up when investors go quiet, mistaking silence for disapproval — but the fix isn't more words, it's staying conversational and high-level so investors stay in a yes mentality.
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Due Diligence: The Pitch Isn't the Close, It's the Doorway
A pitch deck's job isn't to close the deal — it's to earn the investor's permission to dig deeper. Due diligence, not the pitch, is where funding actually gets decided.
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The Renewal Call I Kept Not Making
Tim on the customer renewal he was nervous about for months before he did anything — and why the warning signs are never the hard part, acting on them is.
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Being Right Has Never Once Helped Me
A customer is furious about something we didn't cause, and Tim has never once seen it help to prove that. He's still unsure what he's giving up by not explaining it anyway.
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The Ask: Why Investors Wait to Hear the Number
Investors need to hear a specific dollar amount stated early and directly — not implied, not saved for the end. Vague hinting about funding wastes the one thing a pitch is actually for.
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Your Exit Slide Needs Real Comps, Not Dream Buyers
Investors want to see a realistic path to exit, backed by comparable acquisitions in your space — not a wish list of famous companies who've never heard of you.
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The Client Who Always Has One More Thing
Tim used to read the "one more thing" ask as boundary-testing. Now he checks the scope document first, because most of the time the ask isn't there because he never put it there.
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Two People, Two Right Answers, One Product
Tim used to hunt for the compromise when two people both had a good case. Now he asks which choice can be undone later — and admits he still gets the "undo" part wrong sometimes.
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The Team Slide: Why Eleven C-Suites Sinks You
A cluttered team slide with too many titles or irrelevant advisors reads as insecurity, not strength — investors want the critical few, an honest gap, and proof someone has taken a product to zero-to-successful.
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Why Your Milestone Slide Needs Real Dates
Milestones on a pitch deck aren't decoration — they're the promise investors hold you to. A vague or outdated timeline signals you don't track your own progress, which is worse than admitting you're behind.
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The Demo Only Works In One Order
Tim on the demo that breaks if you click out of order — everyone in the room already knows, and pretending otherwise costs more than the bug does.
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The engineer said three weeks and I wanted one
When an engineer's timeline doesn't match what I hoped for, I've learned to ask whether I'm questioning the estimate or just questioning my own calendar.
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The Traction Slide: Milestones, Not Vanity Metrics
A traction slide should show milestones you've achieved, not tasks you've performed — investors can spot the difference between "100 companies in the pipeline" and five paying customers.
· 2 min read