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

Quickly Unpacking Visa’s $5.3B Acquisition Of Plaid

Earlier today, the news leaked that Visa was to acquire fintech startup Plaid for $5.3B. Plaid is known within the startup and VC community as a strong company, but it is also a relatively quiet company in terms of its own PR and social media... Read More

Why Seed Funds Have Scaled

For those following this blog and the seed market over the past decade, you may have noticed that every year, we see increases across the board — more investors, newer funds, and funds that get larger. Much has been written about the fact that traditional... Read More

Time Diversity In VC Portfolios

A topic that’s been on my mind a lot in 2019 is “time diversity” in venture capital funds. There’s more about this topic all over the web, but the basic gist is — when building a VC portfolio, many investors prefer to have some “time... Read More

Looking Ahead, Predictions For 2020

With a bit of reluctance, I share this forthcoming “Predictions For 2020” post with you. Initially, I wasn’t going to write one because I figured it is hard to know what will happen even with lots of thought applied, and that it may not be... Read More

Looking Back On Tech, Startups, And VC In 2019

It’s that time of year, time to look back and reflect on the most significant storylines in the tech, startup, and VC world. A comprehensive post on this topic could be 5,000+ words, but we do not do such things here. We kept detailed notes... Read More

Why B2B Marketplaces Are Red-Hot

People will often ask me, “So, what are the big tech trends right now?” In 2020, I gave 1.5 answers to that question. The obvious trend in startups (which has been going on for a year or two) is the idea of the “prosumer as... Read More

The Breakout Tech Company Of 2019

It’s that time of year, where I — as a committee of one judge, but now in consultation with my Haystack colleagues Ian and Aashay — select one startup in the tech ecosystem that “broke out” and has the makings of an even larger outcome... Read More

Quickly Unpacking Google’s Acquisition Of Fitbit

Usually these M&A posts involve a private startup being purchased, but this past week, we witnessed a different type of deal — Google acquired Fitbit, which had been a public company for nearly four years. Fitbit was started in a previous startup era, raised about... Read More

Checking In With The Market And Rorschach Tests

Hi everyone. I’m at an offsite down in southern California. Yesterday, I briefly tweeted something that was on my mind (during a break at the offsite) just to get it out of my head. I didn’t check Twitter for hours after that, and then got... Read More

Trimming The Hedges, Planning For A Rainy Day

At the end of 2016, folks in the startup tech ecosystem looked toward 2017’s impending “uncertainty.” Then at the end of 2017, the same worry about 2018; rinse and repeat last year, looking toward 2019. Yet, looking back, not much changed — there’s more money... Read More

Accelerators And Seed Deal Flow

Those of us in the early-stage tech ecosystem by now well know that saying “there are a LOT of seed and new startups” is a gross understatement. It feels like a tsunami of deal flow, and for me, I’ve outlined how I pay attention to... Read More

New Podcast Episode On The Twenty Minute VC

The third interview I’ve done on Harry Stebbings‘ “Twenty Minute VC” was just released. You can listen to it here. Frankly, I am surprised by the response to it. This particular podcast covered quite an arcane topic — how to learn how to manage investment... Read More

The Story Behind Our Investment In Humble Dot

About a year ago, a friend told us about this new work app they were using. Didn’t think much about it. Then, the same thing happened a few days later. It’s just the Bay Area echo chamber at work. And then finally, a few weeks... Read More

The Summer Solstice And Seed Stage Squeeze

If you’ve been following my tweets lately, you’ve read some of my quick musings on the state of the seed market this summer. In short, in my 6.5 years of investing in the seed stage, I have never seen activity levels like I’m seeing today.... Read More

Echolocation

I was catching up on MG’s newsletter/blog and came across this opening line, which got me thinking about a concept in investing, specifically in deal sourcing: To me, all information is about triangulation. Any single source, no matter how close to the situation — and often times... Read More

The Truth About Investor Updates

The topic of “investor updates” has been debated frequently. Most folks who are not close to early-stage startups and new company formation would be surprised to discover that a high number of companies, after receiving funding from individuals or institutions, do not send updates to... Read More