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

This has been an interesting week. Yesterday, HashiCorp listed on the NASDAQ under the ticker $HCP, for HashiCorp Cloud Platform. Over nine years ago, a close friend introduced me to one of his star colleagues, Mitchell Hashimoto, who wanted to get some advice on how... Read More

I’m pleased to announce that Haystack is about to begin investing out of a brand new fund – Fund VI, raised in May 2021 – in January 2022. Our new fund is $50M, just like the previous Fund V. Haystack has shown a deep commitment... Read More

Almost seven years ago, mutual friends introduced me to Krystle Mobayeni. She lived in NYC but was visiting the Bay Area to raise money for her startup. I recall meeting her a few times in/around Palo Alto, in particular the new Blue Bottle as it... Read More

When Noah Jessop joined Founder Collective a few years ago, we met in person just to meet each other. I’ve luckily been friends with the folks at Founder Collective for a while. To give you a sense of how thoughtful they are, they spent the... Read More

I met Tommy Leep over a decade ago now. He was working for Floodgate back then. We immediately became friends. Since then, he’s been on a journey – some ups, some downs. He made incredible contributions to Haystack as a friend and consultant for many... Read More

In the inconsequential world of venture capital, the past few weeks have been illuminating and unpredictable, with a particular focus on the human dimension. Folks reading this likely are in-tune with the realities of today’s markets — we all know technology and startups are attracting... Read More

I shared this last month on Twitter and was delayed in posting it here o the blog. I called it “2021 Venture Capital Market Dislocation.” Credit to my friend Leo Polovets who encouraged me to write this out. Adam Nash tweeted this earlier, paraphrased: The... Read More

Many years ago on this site, I wrote about The Story Behind Haystack’s Investment In Ironclad. Little did I know then what would unfold. Vertical enterprise software took off. Collaboration became the rage. The economics of software and the stickiness of well-crafted products became hard... Read More

Over the past 8-ish years, Haystack as, on occasion, been a thematic fund. Most of the time, though, the fund is more reactive. We meet lots of founders. We get to work with a few of them. And we follow them on their journey. I... Read More

No one really likes investor predictions (unless they’re like this), and I don’t either. Sometimes in the past, like last year, I’ve written them just to farce myself to think, but after last year, it’s doesn’t seem to be the right frame. So instead, what... Read More

At the end of each year, I sit down and distill what happened in our industry. For 2020, it would be trite to say it was a year like no other. Everyone I know is pretty tired of these topics. So, I’m keeping this extra... Read More

I was lucky to be a *very* small part of the early group who invested in and helped DoorDash. It’s incredible to see what they’ve accomplished today. I can’t share this post without saying up front that I’m truly grateful to have been that very... Read More