The legal landscape is shifting under our feet, driven by AI, remote work, and new privacy regulations. I'm predicting the three biggest legal challenges that will define the next five years for startups.
What I've Learned From 31 Companies
A few patterns in startup law come up again and again.
The founders who handle startup law well understand that customer feedback is the only metric that matters.
The Framework That Actually Works
Here is a simple framework for evaluating startup law. It's not complicated, but it requires discipline.
Step 1: timing is everything in this game
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the data tells a different story than your gut
Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly
Nothing works perfectly the first time. The companies that get startup law right treat it as an ongoing process, not a one-time project.
The Numbers Don't Lie
Investing early in startup law can be the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around startup law, AI compliance, future of work that I've been thinking about a lot lately.
What's Next
Best practice in startup law 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 startup law 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:What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
Q:How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
Q:Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
Q:What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.