Investor Updates Matter
Even When Things Are Bad
Most founders treat investor updates as a chore or, worse, actively avoid them when things aren't going well. This is precisely backwards. The whole point of updates is building a pattern of consistent communication that compounds over time. Here's what actually happens when you go dark: investors assume the worst. Human nature. When we don't hear from someone, we create narratives to fill the void. Those narratives are rarely positive. A mediocre update is far better than silence.
The best founders use updates strategically. They understand these emails aren't just about reporting metrics - they're opportunities to shape perception and activate their cap table. Your investors backed you for a reason. Let them help.
The mechanics matter less than consistency. Monthly is ideal, quarterly minimum. Include key metrics, major wins, current challenges, and specific asks. Be direct about what's working and what isn't. Sophisticated investors can pattern match across their portfolio to help solve problems they've seen before. Common pushback: "But what if things are bad?" That's exactly when updates matter most. Bad news doesn't age well. Getting ahead of problems demonstrates leadership and maintains trust. Your investors have likely seen similar situations play out. They can't help if they don't know.
The compound effect is real. Regular updates create muscle memory for clear communication. They force intellectual honesty about the state of the business. They surface problems earlier when they're still manageable. Most importantly, they build relationship equity that pays dividends during tough times. Some founders worry updates take too much time. Wrong optimization. An hour per month investing in investor relationships is high leverage. The real cost is opportunity cost of help you never receive because you didn't maintain lines of communication.
Final thought: your updates signal professionalism and maturity to your cap table. When it's time to raise again, consistent communication will be a strong positive signal. The founders who go dark are the ones who struggle to bridge their next round.
Bottom line: send the updates. Be consistent. Be honest. Use them strategically. The compound benefits far outweigh the minimal time cost. This is zero marginal cost relationship building that most founders completely squander.
I completely agree with you. Regular updates are the first and early sign that we invested in a good team with the potential to become unique. As always, there are exceptions, but they are rare. Every investor deserves to know how the company is doing, especially if they are not shareholders yet. And again, you are right when you say that the best value you, as a founder, can get by being consistently accountable is help along the way. Even if you think you know everything you need to create a massive, successful company—and you don't 99.99% of the time—keeping your partners in the loop is always a competitive advantage. Fairness and reliability not only shape a better self but also lay the foundation for long-term success as a company founder.