If you’re a founder who sends monthly or quarterly investor updates, I have some uncomfortable news.
They probably aren’t being read in depth, and your investors don’t care deeply about them.
I don’t mean they’re skimming them while checking email. I mean they’re genuinely not retaining anything of value from the carefully curated bullet points and graphs you spent hours crafting.
Founders send updates because we have all been told the same thing.
“The best founders I know send regular investor updates”.
You’ve heard it a thousand times, and you want to be seen as a good founder, so you follow the advice and you blast your investor list once a month.
Is it true that the best founders send updates? Well Chronosphere, one of Australia’s most impressive exits in recent memory, sent exactly one investor update across six years before selling to Palo Alto Networks for US$3.35 billion. One update. Six years. Billion-dollar exit.
I’m not suggesting there is causation here, or that you should stop sending updates altogether. Regular communication does serve a purpose. But I am suggesting that you should stop sending out the performative nonsense you are currently sending, and think more deeply about the purpose of the update.
Why are they so bad?
Because they are not honest, and the founder writing them has not stopped to ask “why am I doing this”?
Don’t be performative
Let’s start with honesty. The relationship between a founder and an investor is a delicate one. You want them to believe in you and the company so that they will continue to fund the capital needs of the business. If they stop believing, the funds dry up and you are forced to survive on revenues, run for the exits or find other investors.
In response, you write performative investor updates. You focus on highlighting everything that went well, cherry-picking the data to make it sound like things are moving in the right direction. But startups are hard, and often nothing is going well, so you hide it behind double-speak and optimism theatre. The VC gets the data they need for their own reporting systems. Everyone nods along. Job done.
Except nothing meaningful happened. No trust was built. No insights were gained. No one’s decision-making improved.
Over time, I think this arrangement undermines trust. You think you’re “selling the dream” each month, protecting your relationship with investors by maintaining confidence. In reality, you’re training them to ignore your updates. You’re creating an environment where investors know there’s little signal in your noise.
As a founder, you haven’t stopped to think why writing a regular update is useful. You follow the template your lead VC provided because that’s what “good founders” do. The template captures the management information data points the VC needs. Everyone’s checking boxes, but no one’s thought about whether this serves the company’s interests.
If data collection were the only goal, you could simply give your investors access to your management dashboard or a shared data room. Problem solved. So if the update isn’t primarily about financial information, what is it for?
Demonstrate clear thinking
The most valuable investor updates I have read are written by CEOs who use them as an exercise in clear thinking.
To reflect. To examine the business in its entirety and then put down into words what they truly think. Most of the benefit of the monthly update happens before you even put pen to paper, because you are forced to ask yourself some key questions:
Are we headed in the right direction?
Do we have the right people in the right roles?
Is the traction we’re seeing genuine product-market fit, or just early adopter enthusiasm?
What needs to change and how quickly?
This reflection is where the value lies. It’s your chance to stop running and just sit with the business. Interrogate all your assumptions and beliefs against the actual data before you spend the next month repeating the same shit you did last month.
Once you’ve done the hard work of honest reflection, write as if you’re talking to a trusted advisor, not performing for a board deck. Write as if you are a human.
Be honest
Be intellectually honest. If you’re uncertain whether your recent user growth represents product-market fit or just early adopter enthusiasm, say that. Articulate your hypothesis and what evidence would prove or disprove it. Share the questions you’re wrestling with, not just the metrics that look good.
Frame challenges as you actually see them. Your investors are smart people who’ve seen many companies succeed and fail. They can handle the truth.
If your investor updates feel like a chore or you dread writing them, then you’re doing it wrong. They should be valuable to you first, regardless of whether anyone reads them.
Write honestly about what you are seeing from a place of reflection. Your investors will appreciate the candour, and you’ll have a better chance of building a great company.
