Force Yourself to Write the Monthly Update
Most founders treat investor updates like dental work - painful, infrequent, and only done when absolutely necessary. They send them when they need cash or when they’ve just landed a massive logo. When things are quiet (or bad), the updates stop.
That's not the way to do it - I’m a big believer in writing a monthly update, rain or shine.
The reality is that writing the update isn't just for the people giving you money. It’s for you. As a CEO, you are constantly buried in the day-to-day fires. The act of writing the update forces you to zoom out and look at the business as a whole. You have to synthesize the chaos into a narrative. You can’t hide from the numbers when you have to write them down every 30 days.
It also changes the dynamic of your investor meetings. If your investors are reading your updates, you don’t have to waste the first 30 minutes of a meeting bringing them up to speed. You can skip the "here’s what happened" and get right into the meat of "here’s the problem I need help with."
And if you send them to potential investors - people you want to raise from in the future - you aren't pitching a stranger when the time comes. You’re talking to someone who has been following your progress for months. You stay top of mind.
Build a System, Don’t Write a Novel
The reason most people don't do this is because it feels like homework. They stare at a blank cursor and wonder what to say.
I've built a system that eliminates that problem. I don't want to spend hours writing prose; I want to curate data.
I’ve set up a custom AI project that automates the heavy lifting. I take the artifacts our team is already creating and feed them into an AI project I’ve setup to extract exactly what investors care about:
- Financials: I take the report and commentary our finance team creates in Google Slides. The AI pulls the key metrics - ARR, burn, cash on hand - and compares them to the plan.
- Product: James, my co-founder and Rewind's CPTO, writes a product update in Confluence every month. I export that to PDF and upload it. The system reframes it from "what we built" to "customer problems solved."
- Sales: I upload a CSV from Salesforce with our win/loss reports. It includes comments from the sales team on why a customer picked Rewind. The AI summarizes the key wins and the pipeline health.
- People: I upload a report from BambooHR. The system knows to list specific names only for senior hires (Directors/VPs) and to just summarize the role counts for everyone else.
I put all this into the machine, and it gives me a draft that is 90% there. It’s factual, it’s consistent, and it strips out the emotion.
Track the Relationship
I don't just blast this out via BCC in Gmail. I use HubSpot.
I want to track who is actually engaging with the business. On every contact in HubSpot, I have two custom attributes: “Receive Newsletter” and “Existing Investor.” All existing investors get it, obviously. But I can also tag potential investors, advisors, or friends of the company.
This lets me track the history of every conversation. When I go to raise our next round, I can see exactly who has been paying attention.
The goal isn't to look perfect. The goal is to be consistent. If you only communicate when things are perfect, you build a transactional relationship. If you communicate when things are messy, you build trust.
And at the end of the day, it's a lot easier to ask for help from someone who knows exactly where you stand.