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

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

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

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 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

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

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

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

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

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

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

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

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

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

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

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

Over five years ago, as I began to deploy the first Haystack Fund, I was lucky to select HelloSign as my sixth investment ever. I discovered the product much like you might have – I used it to help handle the paperwork and signatures for... Read More

More often than not, I believe it is largely impossible to predict the shape of an outcome when making an initial venture investment. Investors, of course, will conduct significant due diligence, investigate sources, study trends and the competition — and much more. But, at the... Read More

When I started out investing (via a fund — not my money), I was just investing based on a simple schedule: About once a month, invest $25K into one company I liked. Pretty easy. Over the years, that check size grew slowly to $50K, then... Read More

In gambling, particularly in sports, there’s a concept of “parlay.” The word can be used as a verb (“turn an initial stake or winnings from a previous bet into (a greater amount) by gambling”) or a noun (“a cumulative series of bets in which winnings... Read More