I didn’t skip investor updates because I didn’t care.
I skipped them because opening the doc felt worse than being late.
A blank page asks you to account for the month in full. Cash. The miss. The thing you said you’d ship and didn’t. So you leave it. You tell yourself you’ll do it properly on Sunday. Sunday becomes next Sunday. Then the next month is already underway, and now you’re writing two months at once.
A late update is bad. A blank page is worse. That’s why the delay wins.
The loop I was in
It always ran the same way.
The month ends.
You know you should send something.
You open a doc, stare at it, close it.
Guilt stacks up.
You finally write — and you make it a highlight reel so the wait feels justified.
The longer you wait, the more the letter has to perform. You can’t send three plain paragraphs after three weeks of silence. So you add slides. You sand off the miss. You turn a check-in into a campaign.
Investors didn’t ask for that. They asked whether last month matched the plan, what cash looks like, and whether the list you sent them actually happened.
Theatre is what you write when you’ve been avoiding the page.
It isn’t a character flaw
I used to treat this as discipline. If I were a better founder, the update would go out on the first.
That isn’t how it works when you’re pre-seed or seed, you’ve got 5–20 investors, and there is no finance hire. The update sits under hiring, product, runway, and the fire in Slack. It only rises when someone replies, “We haven’t heard from you.”
By then you’re already writing from defence.
You’re not lazy. You’re protecting yourself from a page that asks for the number you missed.
Name that and the delay gets smaller. You stop waiting for a version that makes the month look finished.
What I needed instead of a blank page
I didn’t need a better Sunday. I needed the page to start half-done.
Last month versus this month already sitting there. Last month’s promises still on the list, waiting to be ticked or deferred. Empty fields staying off the page so I wasn’t inventing copy to fill space. A reason field only if actuals missed plan by about 10%.
That’s the form I built into OnRecord.
Once a month: numbers, what changed, last month’s list, cash, next 30 days, optional ask. Nothing invented. You still edit every line. You download a PDF or send a short cover note and attach it.
The point isn’t a prettier letter. The point is you don’t have to face a blank page after you’ve already put it off.
Send the ordinary version
If last month is still sitting there, don’t wait until you can explain it well.
Write the miss in one sentence. Mark what slipped. Put cash on the page. Send it.
The update you’re avoiding is almost never the one they wanted. They wanted the short one you could have sent on time.
Do that this week. Next month gets easier because this month is already on the record.
I built OnRecord after years of doing this the hard way – putting investor comms off, then overbuilding them to compensate. What they wanted, and what I later understood as an investor myself, was a single-page update I could send without the drama – including just the essentials: last month still on the record, the key numbers (next to the plan), and nothing written to fill the space. That’s what OnRecord does. A monthly update for investors, shareholders and anyone else who needs the same picture – made in ten minutes. Try for 60 days free – that’s 2 free monthly updates. Your investors will love you for it!
All the info they want, nothing they don’t.
