The VC Twilight Zone

Talk to any Bay Area VC in the last 24 hours, and the talk of the town among investors is universal: “What do you think of the SV Angel news?” Depending on your point of view, it is the perfect trigger for a conversation about... Read More

Ramblings On Time Management

This is a post I’ve been meaning to write for many months. Ironically, I’ve haven’t had the time for *this specific* post until now, today. I’m writing while all my three toddlers are napping and my wife went to work to get organized. I’ll likely... Read More

Investing Notes From The Inaugural Pre-Seed Summit

Earlier today, the folks from Afore Capital hosted their inaugural “Pre-Seed Summit” in San Francisco. About 150 people showed up, a healthy mix of founders, seed-stage investors and big fund VCs, and a bunch of LPs of various sizes. Some press showed up, too. “Pre-Seed”... Read More

Quickly Unpacking Uber’s Acquisition Of Jump Bikes

Today it was revealed that Uber, the largest startup/private-unicorn juggernaut reported spent $200M (cash & stock) to acquire San Francisco’s Jump Bikes, a local startup founded all the way back in 2010. There are lots of interesting transit-junkie and international angles related to this transaction,... Read More

As Venture Grows, There Are More Ways To “Get Into The Carry”

Last week, I wrote about the one ingredient required to “get into” venture capital – context. For folks investing today, there are countless more opportunities to invest and some of them actually do not require that much context. It’s the subject for another post, but... Read More

The One Ingredient Required To Get Into Venture Capital

Earlier this week, a super-smart recent college grad pinged me to talk about a potential career in venture. I took the meeting. It was funny to me, in a way, that I myself had those meetings 7-8 years ago. I can’t remember all the advice... Read More

Some Things Change And Some Things Stay The Same

A bit of personal news for readers of this Haystack blog — as it was announced earlier this week, starting Monday (tomorrow) I will become a Venture Partner with Lightspeed Venture Partners. I will continue to run Haystack independently as a single-GP seed fund. You can... Read More

The Story Behind My Investment In Astranis

Back in Q1 of 2016, in my quest to find and fund companies that were providing new ways for individuals and entities to access the Internet, I had heard about a startup in the YC W16 batch called Astranis. I stalked Astranis online, emailed them... Read More

Quickly Unpacking Amazon’s Billion-Dollar Purchase Of Ring

Over the last few weeks, I’ve uttered the phrase “Amazon needs to buy Ring” or “Amazon will compete with Ring” a number of times. Well, today, they bought Ring, allegedly for a rumored amount of $1.2B or more. Wow! Below, I will quickly unpack why... Read More

The Story Behind My Investment In 1confirmation

Mid-way through 2017, a close friend of mine said “Hey, remember Nick? He’s raising a fund. You should ping him.” So, I pinged Nick. It had been nearly three years since we really chatted. It turned out that Nick, who had been a very early... Read More

Dangerous Assumptions

When folks ask “Hey, how’s it going?” I usually respond with “Can’t complain” or “Optimistically paranoid!” It is really how I feel. First off, how lucky are all of us — founders, investors, limited partners, journalists, early employees — to work in such a dynamic... Read More

Investing Notes From The Upfront Summit (2018)

It is probably my favorite “big” tech conference of the year. Every year, in late January, hundreds of VCs and LPs make the trek to Los Angeles for The Upfront Summit, hosted by the team at Upfront and their local sponsors. If Twitter is the... Read More

The Story Behind My Investment In Wag

Back in early 2015, while I was a venture partner with Bullpen, the guys there remarked about one of their portfolio founders on a continuous pivot with his company and that while it seemed crazy, they admired the team’s craftiness in hunting for the next... Read More

The Story Behind My Investment In New Knowledge

If you can remember back nearly two years ago, the tech startup chatter was consumed by a fascination with bots. This was during a time when Facebook Messenger experimented with bots for brands, and when the ecosystem went a little overboard in its hopes for... Read More

The 2018 Seed Stage Reset

This post is about the Bay Area startup and venture ecosystem. I believe the local ecosystem just completed an entire “reset” with respect to the earliest stages of company formation. (I need to state upfront that this isn’t about the seed landscape nationwide — I’ll... Read More

Quickly Unpacking The Uber “Softbank IPO” Exit

Whenever there’s a big startup exit, I try to quickly unpack it here on the blog. There’s been so much news about Uber for the past year and more that, frankly, I have tuned most of it out. It’s almost laughable now three years ago,... Read More

Looking Ahead, Predictions For 2018

Turning the page on 2017, here’s what I’m looking ahead to in 2018: I want to keep this post brief as possible. Below is a set of predictions for 2018 in tech startups and VC. This is also a window into the principles and beliefs... Read More

An Imperfect Glance At Tech’s Notable Exits In 2017

This will be a brief post looking back at some of the notable tech exits of 2017. Before we begin, there are many disclaimers that must be made… [note: if we missed a “notable” exit, please let me know & I’ll update the sheet…] First,... Read More