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

Bites At The Apple, Sharpshooting, And Shots On Goal

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

Fund Investing Versus Fund Management

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

The Parlay

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

Deal Opacity

When I moved back to the Bay Area in early 2011, the technology and startup sector didn’t feel as big or expansive as it does today. In that time, Twitter was just getting its sea legs, the Quora private beta was one of the hottest... Read More

Looking Ahead, Predictions For 2019

Alright, here we go. My predictions for 2019. I am not great at these “looking ahead” posts. We all know the unknown will happen. Looking at my post last year, it wasn’t that great — and my take on crypto was proven wrong. Ok, let’s... Read More

Looking Back On Tech, Startups, And VC In 2018

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

Hot Deals And Good Deals

In the lexicon of startup investors, there’s a term I’ve felt needs to be unpacked a bit: “A good deal.” What is a good deal, really? Is a good deal one that’s hot or competitive? Is that a sign of goodness? Or ones that are... Read More

“Your Portfolio Is Your Path”

You are the average of the five people you spend the most time with. You are what you eat. About a year ago, I tracked down a VC who gave a talk I heard about where he referenced the phrase “Your portfolio is your path,”... Read More

Opportunity Amid Volatility

It’s an unusual time in the markets. With high levels of public market volatility — the first we’ve seen in the age of social media and true real-time information — it feels like everyone and their grandmom is expecting a downturn. “We’re in the nth... Read More

Planning And Strategery Over The Holidays

The end of the year and holidays in general are, at least for me, a time to plan out the next year. Sure, as Mike Tyson mused, everyone has a plan until they’re punched in the face, but even if that punch is coming, having... Read More

Risk And Reward

I’ve been thinking about the timeless phrase, “risk and reward.” Entrepreneurs and investors both need risk in order to reap a reward. Of course, founders and early employees often take very different risks than investors do. There are always examples to break the rules, too... Read More

Briefly Reflecting On The Last Year

With 2018 winding down, I’ve finally gotten some downtime to digest the big changes I’ve personally undergone this year. They’re all good changes. After years of having pretty bad luck, I feel as if I have gotten a bit too lucky. Today is the day... Read More

The Breakout Tech Company Of 2018

It’s that time of year, where I — as a committee of one judge, me! — select one startup in the tech ecosystem that “broke out” and has the makings of an even larger outcome should things continue to go right. As a little tradition... Read More