I’ve Never Seen Anything Like This
This fall fundraising season has been unprecedented in terms of both the quality and quality of companies trying to raise capital.
What’s Going On With Pro Rata Rights?
What causes pro rata disputes and why are they likely to become more frequent in the age of AI.
Why You Shouldn’t Use an Out-of-Office Responder
Here are three common mistakes I see founders make with out of office responders.
Things I Think I Think - Q3 2026
It’s San Francisco Tech Week! Wait…isn’t that every week? Time for 5 Things I Think I Think: Q3 2026 edition.
Now Is Not the Time to Increase Your Burn Rate
I can’t think of a time in my career when capital has flowed this actively yet so little of it has seemingly gone towards extending runway.
What’s Going On with Series A?
What’s happening in Series A right now is the natural evolution of the AI-driven shift that started at Pre-Seed in early 2025 and flowed through the Seed stage beginning in Q4.
The Real AI Moat? Customer Support
The hardest challenge facing AI startups as they scale isn’t technical, it’s technical support.
Lessons from 250 Blog Posts
I never thought I’d actually write for this long, so I thought I would take some time this week to reflect on it. Here are some of the lessons I learned from writing 250 blog posts.
Before You Start Fundraising, You Need to Get Acclimated
Founders trying to raise Seed or Series A funding from Silicon Valley VCs need to change their approach now.
Building in Public: Founders Day Edition
Over the past year, we rebuilt Founders Day from the ground up, added a bunch of new features and unleashed version 3.0 to the world. How did it go?
Stop with the AI Slop, Part 2
What happens when AI slop finds its way into emails and text messages you send your coworkers, clients and friends?
What Do VCs Talk About When Nobody’s Listening?
Last week, I hosted an emerging manager summit in San Francisco with VCs from across North America. Guess what we talked about?
Should I Fundraise in the Summer?
If summer is a bad time to fundraise, why do so many VCs proclaim that they’re open for business?
I Totally Missed Your Email
There’s a good chance many people you interact with these days are aware of when and how often you open their emails. Time to stop making excuses for why you took so long to respond.
What is a Forward-Deployed Engineer (and Why Should You Care)?
Forward-deployed engineers are nothing new (I built a team of FDEs in 2009). But they can be a game-changer.
Cycling the Great Glen Way with Kids
The ultimate guide to cycling the Great Glen way with kids.
Things I Think I Think - Q2 2026
Against the backdrop of this summer’s competition for global sport supremacy, here are 5 Things I Think I Think - Q2 2026 Edition.
The Cost of Hubris
Founder hubris can be deadly for startups. Here's how to identify it early and avoid its consequences.
On Resilience, Rockets and IPOs
Plenty of stories have been written about the history of SpaceX. This is not one of those stories.
What If You Fire Them?
What happens when a VC likes the CEO, but doesn’t have conviction about the rest of the founding team?