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

VC Firm Creation Versus VC Firm Building

Earlier this year, I reflected on the difference between “fund investing” vs “fund management.” It’s a useful post for emerging managers, I’d recommend reading it. The gist of that post is – making investments is relatively easy, but learning to manage a VC fund is... Read More

Three Great Examples Of Email Newsletters Done Right

Earlier this week, I tweeted a thought about the difference I see between blogging versus publishing: “Publishing is when you draft a bunch of versions, have scores of people look at it, maybe a PR eye on it, etc. (often on Medium). Blogging is when... Read More

Two Simple Questions When Considering A Career In VC

There are countless posts on what one should consider when considering a career in VC. The reality today is that, as technology proliferates into all sectors and geographies, venture itself has grown in lockstep with the size of the opportunity. As the economy is now... Read More

Load Management

I’m not a huge NBA fan, but I certainly appreciate the sport. From a business and growth perspective, there’s so much going on with the NBA that’s fascinating to me. And, this particular offseason with all the amazing free agents on the market makes for... Read More

Quickly Unpacking The Looker And Tableau Acquisitions

Normally, I like to pounce on these big acquisitions quickly with some quick analysis, but big M&A in tech is happening too fast, and it’s graduation season for the toddlers, and family is in town, so for this installment of the blog, we will talk... Read More

Quickly Unpacking The $1.4B Acquisition of Harry’s

Believe it or not, this will now be the second blog post on this site about a billion-dollar exit for a shaving-related startup. It was just about three years ago when the startup world learned that Unilever had decided to plunk down a cool $1B... Read More

Mapping The Haystack Portfolio Across The United States

Hello. It has been a while since I’ve posted here, nearly 3 months. My fingers are well-rested, but my writing prowess is likely rusty, so please forgive any rustiness in this post. I do plan to write a lot more this summer, so stay tuned.... Read More

The Story Behind Our Investment In Second Measure

About 3.5 years ago, we met Michael and Lillian from Second Measure while they were in Y Combinator. We were lucky to invest not only during this time, but also doubled down in an extension. And this week, the company announced it had raised a... Read More

Amazon “Swipes Left” On New York City

Start spreading the news, indeed. Today, Amazon announced it will entirely abandon its plans to build its second headquarters (a/k/a “HQ2”) in Long Island City, a residential neighborhood in the borough of Queens, New York City. There’s no need for me to mince words here:... Read More

The Story Behind Our Investment In Fiddler Labs

This is the story of how we invested in Fiddler Labs. At the beginning of 2018, we almost invested in a startup with two strong founders. To make a long and private story short, on the morning I was about to call the founders to... Read More

Quickly Unpacking Spotify’s Acquisition Of Gimlet Media

I’ve been traveling all week, digging out of email, and closing two deals and — hence — have been pretty quiet online. As I was scrolling through Twitter today and saw the rumors around Gimlet, the podcast media company, being acquired by Spotify for $200M... Read More