A bit more than a decade ago, when I was just starting Haystack (a $1M “debut” Fund I), I was a venture partner with Bullpen Capital, juggling lots of consulting roles with a variety of VC firms, and recently became a father, all in the... Read More

On behalf of Haystack, I am incredibly proud to make some big announcements this morning. Before these updates, I wanted to quickly take stock of where Haystack stands after a full decade of investing. Please note, these stats are close approximations that hopefully provide some... Read More

The start of 2022 marked a change in financial markets. Since then, many believed risk capital would dry up, early-stage valuations would fall (just like all other valuations). Now that we are nearly two years into this downturn, I wanted to briefly take stock of... Read More

Haystack is fortunate to be in a position where we work closely with a variety of pre-seed firms, small to large seed funds, and all the big top tier VC funds. We are collaborative by nature, and I’ve always personally felt that the best part... Read More

Earlier this spring, an old friend of ours, Matt Garratt, was kind enough to refer us to two founders he liked personally but felt things were a bit too early for him to take on the investment. Haystack is fortunate to have built long-term, organic... Read More

In the summer of 2019, we met Alex Gallego – a force-of-nature technical entrepreneur with a big idea for the future of data infrastructure and distributed systems. Haystack ended up investing in the seed round of Alex’s company – then called Vectorized – alongside Arif... Read More

Below is a short note we sent to our portfolio founders yesterday. It’s no secret that “AI” is all the rage in startup technology today, but we felt that most of the discussion on this topic centered around new startups. What about existing startups? Those... Read More

I’m on a plane today headed to NYC for the week. I’ve refrained from tweeting too much directly about the implosion of Silicon Valley Bank (SVB) and the threat to other regional banks. This is in part because it’s a complicated topic where there are... Read More

As an unofficial tradition, I attempt to “look back” on the previous year in technology startups and tease out the big themes. Looking back on 2022, I’ll admit I found it harder to step back from the noise of work and family life, to zoom... Read More

Each year, when the summer ends, I begin to think about what I’ll write in this annual “breakout company” post, which has turned into a mini-annual tradition for me here on this blog. Until a few days ago, I kept thinking – just like in... Read More

As an early-stage startup investor, this year, 2022, has been marked by one thing: Hard Conversations. Lots of them. Each conversation is different, but depending on the situation, they fall into one a few buckets. The hardest are with founders who are already in your... Read More

In the summer of 2020, an odd time for sure, my friend and Lightspeed colleague Guru told me about a team he loved but felt was way too early. We took the intro from Guru, and wow am I glad I did. Guru, we owe... Read More

In the summer of 2021, and old friend Eric Ries introduced us to Aaron and Courtney from Schoolytics. I was initially skeptical of the idea — to build a data and metrics platform for all sorts of schools — but in the very first meeting... Read More

In the fall of 2019, as we were opening a new fund (Haystack V), and old friend/mentor of mine Josh Stein pinged me about a deal he was leading in a company called Databook. He and his colleague did a lot of work on the... Read More

Maybe over 10 years ago, I remember a Twitter thread with @cdixon. He was defending startups against critique, citing that journalists and other startup ecosystem players shouldn’t publicly criticize startups because startups are really hard, most of them fail, and it’s the market that delivers... Read More

Nearly 8 years ago, when I was on the verge of finishing Haystack Fund I, I was introduced to a tall, lanky kid who was dropping out of Stanford. I was living in downtown Palo Alto at the time, so took him out to Fraiche... Read More

Back when Haystack just started out, we were fortunate to make a small investment in a friend, Larry. We documented that here years ago. Well, a lot has happened since then. Larry and the team at Envoy have experienced growth, survived through Covid, where their... Read More

For those who know me, I am a planner. I truly enjoy it. And while I’m happy to be flexible when things don’t fall the way I’d like, I oftentimes build concurrent plans as options along the way, just in case those things happen. At... Read More

As a mini-tradition here on this blog, at the end of each year, I attempt to briefly summarize and contextualize the big events that happened in the world of tech and VC. It’s impossible to touch on everything, so for reflecting on 2021, I’ve tried... Read More

It is that time of year on my blog. This year-end tradition has lasted happily longer than I would’ve predicted. Each year, as a “committee of one,” I declare the breakout startup of the year. Let’s briefly revisit the past: In 2012 it was Stripe; then Snap in... Read More