Every founder should write investor updates. Monthly or quarterly. No exceptions.
I have sent 37 consecutive monthly investor updates at Yuma. Every single first of the month. If the 1st is a Sunday, I send it Sunday. If I am traveling, I send it from the plane. Holiday? Does not matter. The 1st is the 1st.
Here is why it matters more than you think.
My update goes to the same group every time: my investors, my entire team, and a few friends that I keep in the loop to hold me accountable. Same document. Same numbers. Everyone reads the same thing.
I share the finances, the wins, the losses, the hard decisions. No filter, no separate "rosier" version for investors. The team sees the exact same reality.
Every single one of my teammates could be at a bigger company with more stability and more pay. But they chose a startup for a reason. The thrill, the purpose, the impact of not being a tiny cog in a big system. So they get the full picture. Good months and bad months. We share the roller coaster together.
It is also a forcing function. When you write down what went wrong every single month, you can't hide from it. If the same problem shows up 3 months in a row, you can't pretend it is not there. You don't have to solve everything immediately, but you have to confront it. Your investors and your team can see it in the numbers whether you address it or not.
As an angel investor myself with 90 investments, I also receive a lot of updates. I don't read them as much as I should because Yuma eats all my time. But I notice who sends and who does not. There is a pattern. Founders who go dark are almost always the ones struggling. That is exactly when they should be communicating more, not less.
The hardest months to write are the most important ones. When cash is tight, when a key hire says no, when growth stalls. Most founders go quiet in those moments. That is a mistake. That is when your investors respect you the most for showing up.
37 months. Through good times and bad. Always on the 1st. That is what works for me, at least.