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

Public Frenzy And Private Caution

Love it or hate it, the stock market is the sentiment machine for the United States. It is our nation’s Fitbit, Apple Watch, mood ring, tarot card, and more for getting a pulse of our economy today and a glimpse into what shareholders believe the... Read More

Portfolio Triage In A Pandemic World

Everyone is doing their own version of “triage” right now. Let me state upfront – I recognize using medical terminology to discuss non-medical emergencies during a public health crisis is not ideal. To be clear, it is not my intention to equivocate the portfolio “triage”... Read More

Investment Decisions In A Pandemic World

This is a post for startup founders to hopefully better understand how investors and VC firms are adjusting to this new world. There are lots of tweets floating around citing “business as usual” and “we are open for business” — and while those proclamations and... Read More


in a previous era, there was political speech about a campaign of “Shock and Awe.” The idea, in those times, was to use military strength and western idealism to win “hearts and minds” of innocent citizens in the Middle East to see the valor in... Read More

Semi-Lazy Sunday Afternoon Musings On Reserves Management

Each weekend, I like to write a short post about a topic I’ve been learning in fund management. The topic for this weekend was originally slated to be “reserves.” However, now the world is very different and we are all readjusting to a terrible reality.... Read More

A Quick Guide To Startup Fundraising In A Pandemic World

After lots of conversations this week with both founders and investors (from early to late), I wanted to quickly jot down my thoughts as they relate to what startups can expect in 2020 when raising funds. The first disclaimer here is, obviously, capital financing for... Read More

Lazy Sunday Musings On Dilution

One big topic newer fund managers won’t likely appreciate in the early days is the effect dilution can have on an early-stage investment. I know this because I had no clue about it when I started. Even when other investors would ask me about it,... Read More

Late-Night Musings On Portfolio Construction

Without a doubt, the concept of “Portfolio Construction” was the most difficult VC fund management concept for me to get my arms around. To be clear before I write this, and before you read it, by no means do I mean to suggest that now... Read More

Shots On Goal

The politically-correct line to use when making a startup investment is that it’s based on “conviction.” As an investor, in order to make the investment, you have so much belief in the founding team, or the idea, or the category, or the traction, or some... Read More

Misconceptions About The Path To Get Here

This is squarely a very personal post, and I will try to keep it short and sweet. As a disclaimer, I do not intend this post to be read and/or interpreted as talking down to anyone or being disrespectful. Yet, I need to make this... Read More

The VC Industry Norms Which Changed Over The Past Decade

Having spent time around and then in the world of VC in the Bay Area during the last decade, I’ve been reflecting on how different norms in the industry have changed. At the start of 2010, there was some unwritten VC industry conventions that have... Read More