Founders who get D&O insurance right stand out immediately.
A comprehensive look at D&O insurance. We break down the complex legal jargon into actionable steps for early-stage founders.
The Counterintuitive Truth
In D&O insurance, the best practitioners often do less, not more.
Trying to do everything at once is one of the most common ways to fail: even a team with strong technology and talent can spread itself too thin.
The lesson: you should focus on one thing and do it exceptionally well. It sounds simple. It's incredibly hard to execute.
What I've Learned From 127 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 timing is everything in this game.
Real Talk: What Actually Matters
Here is what actually matters in D&O insurance.
First, execution speed beats perfection. Every time. Companies rarely fail because they moved too fast on D&O insurance. Many fail because they moved too slowly.
Second, measure everything. If you can't measure it, you can't improve it. Set up tracking from day one, even if it's basic.
Third, talk to your users. It sounds obvious, but many founders make decisions about D&O insurance in a vacuum. Get out of the building. Talk to real people.
This connects to broader themes around startup insurance, D&O insurance, risk management that I've been thinking about a lot lately.
What's Next
Best practice in D&O insurance is changing fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
If you're building in this space, the best time to get D&O insurance right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
Frequently Asked Questions
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: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: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.