The Long Haul Of Building A Venture Capital Firm

There are countless posts flying around the web now about “How to build a startup.” It’s great that all this knowledge has made its way online. On a slightly smaller impact scale, there isn’t a lot of content out there about “How to build a... Read More

Conviction, Diversification, and Portfolio Construction

Sometime within the last 48 hours, I tweeted about a potential test for an investor’s true conviction in a company he or she invests in. Specifically, I wrote: Investment “conviction” is a really overused term. If you want to test it, most investors’ LPAs permit... Read More

Rolling Closes Versus Synchronous Closes

Earlier this week, in the wake of Y Combinator’s Demo Day, I saw a tweet go viral and generate lots of chatter. The tweet was written by YC’s President, Michael Seibel. I’ve never met Seibel (yet) though, of course, have heard amazing things about him from... Read More

Putting The Money To Work

About two years ago, when I was starting to raise Haystack IV, I sat down with one of my VC mentors at The Upfront Summit in LA to get his quick feedback on my slides. He ended up focusing only on 2-3 slides and then... Read More

Scooters, Clear Lanes, And Permissionless Innovation

It’s been a summer of change. I had been meaning for weeks to write a longer post on scooters, as an attempt to collect my thoughts on the topic, specifically around the market size, unit economics, and defensibility– but life got in the way. (Perhaps... Read More

Discussing All Things VC On The Recode Decode Podcast

 A few weeks ago, I sat in “the red chair” of Recode Media’s Decode Podcast recording studio in San Francisco. Most tech podcasts I’ve been on are usually recorded in some back room or startup side room, but not this episode… no, no. Recode’s... Read More

The Story Behind My Investment In Downstream

Earlier this summer, my friend Michael told me about a small investment his team made up in Seattle in the Amazon ecosystem. We were about to move houses and with all the impending details that process was generating, I initially didn’t give it a proper... Read More

“There’s A Disturbance In The Force”

I say “no” every day, multiple times a day. Even though I know I’m upsetting folks, I try to be direct, open, quick, and honest. Not everyone will like it. So be it. I elect to be consistent and fair rather than liked. Yet, once... Read More

Investing Outside The Bay Area

This is a post I’ve wanted to write for a long time, but I needed the time to digest all the other great posts on the topics by other investors, and to analyze specific portfolio data from Haystack over the last five years. Well, that... Read More

The First Live Meeting With A Founder

Recently on this blog, I’ve been attempting to unpack how an investor can sort through deal flow and potential investment opportunities. After writing about “the quick kill” to discard of inbound flow, next I wrote about what actually captures my attention and graduates to a... Read More

Paying Attention To Inbound Deal Flow

About a month ago, I wrote a post about how the Bay Area seed ecosystem is generating deal flow levels that are nearly impossible to keep up with. In the post, titled “Seed Deal Flow Tsunami And The Quick Kill,” I attempted to explain how,... Read More

The Harsh Reality Of The Preference Stack

I recently shared this article and tweeted this, and I was quite surprised by the thread it triggered and the reaction it generated. After reflecting on it for a day, I began to understand why — even though this topic has been written about many... Read More

Quickly Unpacking Amazon’s Acquisition Of PillPack

By now, one wonders what tech news will be tucked into the public record the days before a major holiday travel week approaches. While I have no horse in this particular race, I was really excited to read that Boston’s PillPack was being sold to... Read More

Quickly Unpacking ATT’s Acquisition Of AppNexus

What does a massive telco do to follow up an $85B acquisition of Time Warner? Spend about $1.6-$2.0B on AppNexus, of course. In an age where $7.5B exits like that of GitHub to Microsoft make the big waves, acquisitions like that of AT&T buying AppNexus... Read More

When The Profile Gets Ahead Of The Proof

I heard this line this past week, and it’s been like a catchy lyric playing over and over again inside my head: “Their profile is ahead of their proof.” Written another way, when Profile > Proof. It could apply to a company, a startup, a venture... Read More

Bourdain On Writing

I’ve been listening to lots of old Bourdain interviews and episodes. This re-run of a 2016 Fresh Air interview caught my ear, specifically the excerpt below. DAVIES: Now, the book and the article is this, like, grab-your-attention look at things you don’t know about what... Read More

Response To A Thought-Provoking Tweetstorm

A stranger (hopefully a future friend, Pietro Invernizzi) on Twitter tagged me as part of his tweetstorm earlier today about his hope for how VCs and founders should interact around and during a pitch. It was a longer tweetstorm, and I felt it would be... Read More

Thank You, Anthony Bourdain

I woke up a few minutes before 5am PST on Friday. I always look at my phone right away. I know it’s “not good for me,” but whatever. And, within seconds, I saw the news about Anthony Bourdain. I wasn’t surprised. Maybe I’m desensitized to the... Read More

Quickly Unpacking Microsoft’s Acquisition Of GitHub

Satya strikes again. After being installed in 2014 as Microsoft’s new CEO, Nadella has turned around the Seattle ocean liner on a new course after the Ballmer regime. With Microsoft’s stock price (and technology brand) soaring of late, Nadella and his team have not been... Read More

Seed Deal Flow Tsunami And The Quick Kill

If you read yesterday’s post, you can see just how insane the proliferation of seed financings have been. As a result, I personally cannot keep up with all the deal flow. This a common refrain among many seed investors in private. When I started investing... Read More