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.
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?
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.
On Resilience, Rockets and IPOs
Plenty of stories have been written about the history of SpaceX. This is not one of those stories.
What’s Going On With Accelerators?
With more accelerators and fellowships than ever, it might seem like there’s an overabundance of options for founders to choose from. What we’re seeing is actually a clustering around two very specific approaches to hands-on investing.
Snakes and Ladders
Over the past 18 months, Silicon Valley has sped up. And most people outside of the Bay Area have no clue just how wide the chasm has become.
Things I Think I Think - Q1 2026
Three months ago, nobody had heard of OpenClaw, OpenAI was valued at a mere $500B, and Anthropic was signing multi-year partnerships with the U.S. Government.
What’s Going on with Seed Rounds?
Another major shift is underway and, this time, it’s throwing off founders, angel investors, and Pre-Seed VCs alike.
AI Price Drops Are Coming
Right now, AI companies around the world are capturing unprecedented revenue. But it won’t last forever.
Stop, Collaborate and Listen
There are moments in time when it’s important as a founder to stop and pay attention to what’s happening around you. This is one of those moments.
When Distractions are Everywhere, Focus Wins
The rate of advancements resulting from AI is nothing short of astonishing. But for founders, it can be a major distraction.
Things I Think I Think - Q4 2025
Now that we’ve all made it through our backlogged New Years inboxes, let’s reflect on Q4 and kick off 2026 with my latest homage to legendary sports columnist Peter King
Things I Think I Think - Q3 2025
The memories of summer are fading. Burning Man is over. And the kids are back in school. Here are 5 Things I Think I Think: Q3 2025.