For most companies, investor relations and communication are unpleasant hygiene, like a dental cleaning, something to get through as fast and painlessly as possible, often delegated to automations, ops, finance, or IR. The way some founders do it, it's a beautiful art form all unto itself: clear, plain-spoken prose, minimal corporate-ese doublespeak, humor, often self-deprecating, lessons learned, and plans for the future.

I am thinking first and foremost of Warren Buffett, but this would also include Jeff Bezos & Amazon.

“Mistakes — yes, we make them at Berkshire… Don’t beat yourself up over past mistakes — learn at least a little from them and move on.” — Warren Buffett

“I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins.” — Jeff Bezos

More recently, I've discovered that Patrick and Jon of Stripe and Immad of Mercury also publish lovely letters. What they share is a willingness to explain how they think, what they got wrong, and what they plan to do next, in their own voices.

To me, these kinds of investor letters fit into the broader legible universe that includes Date Me Docs (which I am proudly the world's leading advocate for), beautifully written job postings, and founder-written blogs, like Paul Graham's. In all of these, the common thread is creators speaking plainly and directly to the world.

The are big benefits to taking investor relations and communications seriously. First, it helps you build trust:

1. Build trust with capital markets. Over time, they learn how you think, act, and allocate capital. That earns you a longer leash to make long-term investments, more grace when you have missteps, and often higher multiples than competitors who stay opaque. Something that surprises many people is that public markets actually include plenty of extremely long-term oriented investors. Buffett talks about this a lot, and I have many investor friends who think the same way.

2. Build trust with labor markets. Employees, who are always implicit underwriters of a business and often shareholders themselves, see that you are trustworthy stewards of their careers, livelihoods, and reputations.

3. Build trust with customers. They can see more behind the curtain how you are trying to serve them, not trick or exploit them.

4. Build trust with the public. You explain why your company exists, what purpose it serves, and how you try to be a good community member. In this anti-business and anti-billionaire climate, some scorn is earned, but some of it comes from a lack of transparency that leads people to assume the worst. I’ve never heard anyone say anything bad about Warren Buffett, and there’s some public relations genius there worth studying.

There are also a couple benefits that don’t quite fit under “trust,” but matter just as much:

1. Attract the partners you want and repel the ones you don’t. Buffett talks a lot about the importance of aligned partners for the long term. The last thing I want is an investor looking to make a quick buck or take the company in a different direction, or a customer or employee who wants us to be something we don’t want to be.

2. Better internal decision making and alignment. Spending time on investor communications makes oneself and one’s company more legible internally. (Sometimes I joke that the Date Me Directory is a dating app whose best feature is that it "tricks" people to be more thoughtful about who they are and who they want to be in a relationship with. Internal legibility, aka clarity, is worth the all by itself.)

But from an efficiency perspective, publishing thoughtful investor letters is a worthwhile use of time simply because you should be doing this reflective thinking anyway. And if you are going to spend the time reflecting, you might as well publish it and kill many birds with one stone: clarity for yourself, and legibility to everyone else. Often the only thing stopping you is a vague fear or making things more public than you need to. In my calculations, the benefits way exceed the costs for me, especially for the long-term, positive-sum games I intend to play for my career. Increased public legiblity helps others fit you into their stories where appropriate, increasing your “luck surface area.”

This is why I plan to start publishing Val Town's Monthly Investor Updates. My very next Val Town investor update, which I’m writing now, is intended to be public, so hopefully within a few days folks can read it.