Welcome back to Part 2 of The Downside of Investor Newsletters, and kudos for sticking around—clearly, you’re committed to making your investor updates stand out.

In the last post, we got into why sending monthly updates isn’t always the best move for founders. We talked about who actually benefits— mostly top-performing founders and investors who are already engaged. And even if you’re killing it, all that work putting together those updates might not be worth it.

In this part, we’ll cover how to make strategic updates that don’t just share news but also create opportunities for engagement. For instance, you’ll learn how to announce a major milestone and make a strategic request, like asking for referrals or help with new hires. We’ll also look at some practical examples, such as how to update after a significant achievement or a hiatus, to keep your investors genuinely interested.

Stick with me— this is where we get into the good stuff…

Controlling the Narrative: Turning Milestones into Opportunities 

When you think about investor communications, you want to control the narrative at all times. Even if your company is fully executing, and running on all cylinders, there’s always a more sophisticated way to approach communicating with investors and building relationships. In a world where perception is reality, that’s what it’s really all about. Here’s what I would advocate for: don’t blindly send a regular monthly investor update.

First, it’s not worth your time to update people who might not even invest in you. Second, it’s not beneficial to share months that aren’t great. Instead, think about having a mailing list of prospective investors that you update in a way that positions your company as interesting. 
It’s all about owning your story. Make your updates one-off announcements with specific reasons for emailing, not just because you’ve committed to a monthly update.

Remember, every interaction with prospective investors is an opportunity to showcase your strengths. Rather than sending routine updates that might go unnoticed, use your updates as a tool to build excitement and highlight pivotal moments in your company’s journey. Craft each message with a clear purpose, whether it's to demonstrate growth, celebrate a win, or make a strategic ask.

For example, if something good happens or you achieve a milestone, this might be the time to send an update out and tie it to some sort of request for help. You could say, 'We’ve achieved great traction in our market, and our revenue is growing rapidly. We now need to hire a best-in-class head of performance marketing. If anyone has recommendations, we’d love to connect!'"

This approach has the benefit of sounding like “I don't need your money. I need to hire” while also sharing progress. It’s a much more powerful way to beat your chest.

Here’s another example of an update that you might send after months of radio silence: 

"Hey, I know you’ve been following our journey. We wanted to reach out to everyone who has supported us and ask if anyone has any connections to the telecom industry. We’ve been doing extremely well over the last three months—we’ve grown 30% month-over-month, added some of the best talent in Los Angeles, and now we’re ready to take on telecom. Does anyone have introductions to AT&T, Verizon, or similar companies?"

This kind of update is much more compelling because it’s tied to a request. The request emphasizes that you’re growing so well that you need help connecting to top-tier companies, which can really pique investors' interest. Compare this to a generic monthly update— while it might include some good news and may get read, it just doesn’t have the same impact.

So, I encourage you to rethink your communication strategy with investors. Instead of defaulting to a monthly newsletter where you might struggle to make each update compelling, try something more engaging. Try visiting regions where they’re based and making an effort to meet with them in person. These strategies will serve you much better than a generic, blind investor update.

Alright, that’s my hit piece on the investor newsletter! I know, this might’ve been a bit of a buzzkill if you were expecting a love letter to monthly investor updates 😜. But hey, sometimes you gotta face the truth to spot a chance to do better. If you have your own take on this or want to share your thoughts, drop a comment, I’d love to hear from you.

Be chased,
Jason