The investor communication playbook: a guide to perfecting your updates

There's a window most founders miss. You close a round, the money hits the bank, and then... silence. Months pass. Your investors hear nothing until you need something again.

I've been on both sides of this. I raised over £3m for CROSSIP and I've backed more than 20 startups through Aligned Syndicate (previously Sowing Capital). Poor investor communication doesn't just damage relationships, it can quietly close doors that you'll need open again.

Right now, that silence is especially costly. The UK tax year ended on 5 April. Investors who rushed to deploy EIS and SEIS capital before the deadline are now in monitoring mode. They've just written cheques. They want reassurance. If you send a well-crafted update in the next few weeks, you'll stand out from the majority of founders who go quiet the moment the money lands.

Here's how to do it properly.

The triple threat: The Good, The Bad, and The Ask

Every investor update should be built around three things.

The Good — lead with your north star metric. Don't bury the headline. If you hit 115% of your Q1 revenue target and brought on a new Head of Ops, say that up front. Don't make investors hunt for the win.

The Bad — this is where most founders fall short. Investors aren't naive, and we know every business has problems. What we don't know is whether you're on top of yours. An honest founder who admits the shortfalls gains more respect from their investors. Investors also hate surprises. So if churn ticked up, say so. Tell them why and what you're doing about it. That's the kind of transparency that builds trust.

The Ask — the part almost everyone leaves out. "Let us know if you can help with anything!" is not an ask. It's noise. A specific ask like "Can anyone intro us to the Head of Procurement at [specific company]?" is far more likely to get a response. Your investors want to help. Give them something actionable.

Here's what that looks like in practice:

What metrics to use in investor updates

A one-size-fits-all update is usually a bad update. The metrics that matter depend on your business model.

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Whatever sector you're in, always include your runway. Investors need to know how long you have and whether you'll be back in market soon. You don't need to over-explain it, just state it clearly.

How often to send

You'll see advice often recommending monthly updates. I get it, as the logic sounds right. But I'm on the receiving end of a lot of investor mailing lists through Aligned Syndicate, and I'll be direct: monthly is too much for me.

If you're one of say 20+ companies an investor has backed, that's an update landing in their inbox almost every single day. It becomes noise, and noise gets ignored.

My view is that quarterly is the sweet spot. It mirrors the rhythm of public markets, it gives you enough time for something meaningful to actually happen between updates, and it keeps your investors genuinely engaged rather than quietly tuning out.

For investors or advisors who want to stay closer to the journey, and plenty do, point them to your LinkedIn. Regular posts about what you're building, what you're learning, and where you're heading give people a way to follow along without you having to write a formal update every four weeks.

What doesn't work is going quiet for six months and then getting in touch when you need something. That's the fastest way to damage the goodwill you've spent months building.

The mistakes that quietly damage confidence

A few common ones I see again and again:

• Only sharing good news. Investors know businesses have problems. If you filter everything out, they stop trusting the updates
• Updates that read like press releases. Too polished, too corporate, no honesty
• Burying the ask. Or not including one at all
• Updates that are too long. Keep it brief, if it takes more than three minutes to read, most won't finish it

Keep it structured, honest and consistent.

Building the relationship before you need it

The founders who raise follow-on rounds faster aren't always the ones with the best metrics. They're the ones whose investors already believe in them, because they've kept them close.

A consistent update habit turns your existing investors into allies: people who open doors, make introductions, and back you again when you're raising next. That's not a nice-to-have. It's a genuine competitive advantage.

If you're thinking about what the right investors look like for your next round, ThatRound helps founders find and connect with the ones that are actually a fit.