Ironclad: Transforming The Whitespace In Digital Contracting

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

The Story Behind Our Investment in

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

Looking Ahead To 2021 – Planning, Not Predictions

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

Looking Back On Tech, Startups, And VC In 2020

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

Quick Reflections On Seeing DoorDash From The Early Days

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

The Story Behind Haystack’s Investment In Candu

In the early days of Haystack, we would share stories about new investments. Then, the industry exploded. So many more startups. More investors chasing them. More noise. And, so, we’ve become more muted about sharing publicly what the investments are, especially at the early stages,... Read More

Quickly Unpacking A Wild Week Of Big Exits – Gainsight, Kustomer, Slack

For usual readers of this blog, by now you’re perhaps used to seeing a new post “Quickly Unpacking” the latest technology startup acquisition, usually of the billion-dollar plus category. Throughout the history of the modern startup ecosystem, “billion dollar exits” drove the model, the returns,... Read More

The Quest For The Next DocuSign

The last few weeks, the same question has surfaced: “What on earth is happening in the seed market?” My answer: “Everyone is on the hunt for the next DocuSign. And it’s a bloodbath.” Let’s wind the clock back over two years. In the summer of... Read More

Constraining The Path

(This is a post where, if it resonates with you, I’d encourage clicking on and reading the links embedded.) In the context of entrepreneurship and the creative process, I am a big believer in constraints. I fundamentally believe that a shortage of resources, or a... Read More

Totems And Rivers

To say 2020 has been an unsettling year would be an understatement. It is not lost on me how this year, the pandemic, the lockdowns, the divisions – it has wreaked havoc on our attention, on our livelihoods. The impact of 2020 has, unfortunately, been... Read More

Stated vs Revealed Preferences

In the world of creating, building, and financing startups, people do a lot of talking. A lot. We know this all too well on the investor side, with all the blogs, tweets, and panels. Especially now, now that most of our working lives are happening... Read More

The Fight For Ownership

I am stating the obvious in this opening sentence, but I need it for the post: In each round of funding for a startup, the founders sell a portion of their equity in exchange for cash. While there’s variance, it’s accepted that founders will experience... Read More

The Breakout Tech Startup Of 2020

I didn’t plan on writing this today, but it happened. I have to write this quickly tonight. As a little tradition on this blog, I’ve singled out companies starting in 2012 with Stripe; there was Snap back in 2013; Slack in 2014 (after prematurely saying... Read More

Quickly Unpacking Twilio’s $3.2B Acquisition Of Segment

It’s our twin sons’ birthday this morning, and no one wants to read (or write) a very lengthy post, but before I head out to run some errands, I need to quickly unpack last night’s news that Twilio, a $45B public company (wow!!) is about... Read More

The Alignment Summit V, It’s A Wrap

Last week, we held The Alignment Summit V online via Zoom webinar. Instead of a full-day in-real-life event that’s quite special, we made it entirely online, short, and still special, I think. For those of you know me, you know that this is a very... Read More

Finding The Track

For those who know me, they may laugh at the metaphor I’ve recently latched on to. I am not a big “outdoors” person. Sometimes I joke with people who gush about camping or ocean kayaking that “I actually like the indoors.” Yeah, I’ve gone camping... Read More

“Risk-On” And Digital Antibodies

With the arrival of June 2020, it’s almost as if there is no pandemic when it comes to the early-stage investment market in the Bay Area. The early-stage tech formation world and the VCs that support them are mostly “back in business.” Some never really... Read More

“Listening Mode”

Since 2008, I have been a very active Twitter user. Over 100,000 tweets later, Twitter is not only a product I use many times a day, it is the number one used app on my phone, week in and week out, far ahead of any... Read More

Adaptation And The Shape Of A Deal

As an early-stage private market investor, one of the many things I obsess over is how to design and manage the funds we raise and deploy. Ask 100 peers how they do it, and you’ll likely get 101 answers back. The problem is, as each... Read More

Goldilocks In The Time Of Coronavirus

Ever since becoming a dad in 2013, I’ve been obsessed with obsessing how I organize and spend my time. That obsession only intensified when our twin boys arrived in 2015. Ever since, it’s been hour by hour, each unit of time accounted for with as... Read More