A comprehensive look at D&O insurance. We break down the complex legal jargon into actionable steps for early-stage founders.
What I've Learned From 109 Companies
Across 234 angel investments, including Anthropic, a few patterns in D&O insurance come up again and again.
The founders who handle D&O insurance well understand that you need to move fast and break things.
The Reality Nobody Talks About
A lot of the advice on D&O insurance rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that the data tells a different story than your gut. I've seen this play out across dozens of companies. The pattern is unmistakable.
Many teams spend months on the wrong path before realizing that simplicity beats complexity every time. Once they make the switch, everything changes.
The Counterintuitive Truth
In D&O insurance, the best practitioners often do less, not more.
The lesson: customer feedback is the only metric that matters. It sounds simple. It's incredibly hard to execute.
Lessons From the Trenches
I want to share a few specific lessons I've picked up over the years. These aren't theoretical. They come from real companies, real failures, and real successes.
Lesson 1: The best time to start thinking about D&O insurance was yesterday. The second best time is now. Don't wait until you have the perfect plan.
Lesson 2: Hire for attitude, train for skill. The best people at D&O insurance are rarely the most technically gifted. They are the most curious and persistent.
Lesson 3: Your competitors are probably getting this wrong too. That's your opportunity. While everyone else is following the same playbook, you can zig when they zag.
This connects to broader themes around startup insurance, D&O insurance, risk management that I've been thinking about a lot lately.
The Bottom Line
None of this is rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at D&O insurance aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
Companies that take D&O insurance seriously tend to pull ahead of the ones that don't.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
Q:What if I disagree with some of the advice?
Good. That means you're thinking critically, which is exactly what a good founder should do. Take what resonates, test it, and discard what doesn't work for your specific situation. No advice is universal.
Q:Is this guide based on real experience?
Every recommendation in this guide comes from direct experience, either from building and selling my own companies, or from patterns I've observed across 234 angel investments. I don't write about things I haven't personally tested.
Q:How should I work through this guide?
Don't try to absorb everything in one sitting. Read through once to get the big picture, then go back and work through each section as it becomes relevant to your current challenges. Bookmark it and return to it regularly.
Q:Who is this guide designed for?
This guide is written for founders and operators who want practical, actionable advice rather than theoretical frameworks. Whether you're just starting out or scaling an existing business, the principles here apply across stages.