I treated the investor update like a product launch. I made it get so ‘big’. So, I’d put it off. Then I’d feel guilty. Then I’d open Keynote or PowerPoint and try to make the month look finished and perfect.
The deck got longer every time. Charts. Narrative. A cover and a bunch of slides I had no business designing. By the time I hit send, my ‘monthly’ update was fifty pages and weeks late - sometimes months!.
Needless to say, my seed investors in my startup weren’t happy.
I told myself they wanted the work – they wanted to see we’d taken it seriously. But what they wanted was last month’s numbers, whether we hit the plan and didn’t, cash position, and whether the things I promised actually happened. They also wanted to see where they could help.
Everything else was noise they had to wade through to find the four lines that mattered.
The founder version of the same mistake
This wasn’t a one-off. It was the pattern.
As a founder I knew the update sat at the bottom of the list. A blank page felt worse than a late one, so I waited. When I finally wrote, I overcorrected. I turned a letter into a performance.
You know this loop if you’ve raised. Five to twenty people on the cap table. No finance hire. You know the email matters. You still don’t send it until the next month is already eating the last one.
A late update is bad. A highlight reel is worse. Investors learn to discount you when every page is a win.
I did it again at a much bigger company
Later I was CMO at a new bank. Shareholder comms sat with me too.
Same instinct. Bigger budget. Nicer design. Still the wrong object.
We shipped extravagant communications that didn’t always land. Internally it felt like we’d done the job. From the other side of the table it was a lot of paper to get to cash and variance.
I only saw that clearly when I started writing cheques myself.
What I wanted as an investor
I didn’t want a board pack from a seed company.
I wanted a page I could read between meetings.
Plan versus actual
Why it moved, if it moved
Cash
Last month’s promises: done or deferred
What you’re doing in the next 30 days
An ask, if you have one
That’s it. I did not want a story that invented a better month. I did not want a template that wrote the number I wished they’d hit. I did not want to hunt for the miss in appendix seven.
All the info I wanted. Nothing I didn’t.
When founders sent that, I relaxed. When they sent a designed novel, I assumed something was being ‘managed’.
The product I couldn’t find
I looked for a way to do the small letter every month without starting from zero.
Chat windows will write the letter. They will not remember September when October opens. A new doc every month is how last month’s promises fall off the page. A deck tool is how you end up designing again.
So I built OnRecord.
It is a short form you complete once a month. Numbers. What changed. Last month’s list to tick or defer. Cash. Next 30 days. Optional ask. Empty fields stay off the page. Nothing is invented. If actuals miss plan by about 10%, you add a reason.
It turns that into one page, in your logo, colours and type. You edit every line. You download a PDF or copy a short cover note and attach it.
Month one is a letter. Month two is why it exists: last month’s plan is still waiting.
What this is not
Not a pitch deck.
Not a board pack.
Not a compliance mandate.
Not a Sunday spiral with better typography.
The job is to get an honest one-page update out the door in about ten minutes, every month.
If you owe last month’s update, don’t open Keynote. Write the four things they actually read. Send the page. Keep the promise list on the record.
That’s the whole product. That’s the letter I wish I’d sent.
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.
