A few weeks ago, Chris Mims of The Wall Street Journal wrote a great piece on the struggle between entrepreneurial energy spreading across the country while the dollars allocated by LPs in venture capital funds increases in concentration in the Bay Area. Specifically, Mims reports... Read More

Like any big startup acquisition, there is a rush to unpack it, especially when the price tag is rumored to start with a “B.” There’s a lot of bragging rights and credibility wrapped up in that number, and the ecosystem will even fudge numbers a... Read More

This is going to be a fun story to write about Myra Labs. About a year ago, my good friend Nakul told me I should meet this guy spinning out of Bloomreach — Viksit. I happen to know one of the founders of Bloomreach, who... Read More

Back around the holidays in 2015, one of my LPs (who is also a friend) sent me a note about a YC company from the most recent batch, S15. I had been at YC and saw the company, but hadn’t been thinking about the “AR”... Read More

Over the past few months, a number of people I know well but maybe haven’t seen in a long while have resurfaced in life. It is great, and I can’t explain the timing. Maybe it’s summer. Maybe I have more time and am not traveling.... Read More

When I started my third fund, Haystack III, back in August 2015, I thought I was so organized — I would build a portfolio that was evenly split across three areas of interest: SaaS, the backbone of many portfolios; consumer products and services, which are... Read More

Long before Instagram was created, nearly every technology observer realized the massive potential of mobile phone cameras. Kevin Systrom, the famous CEO of Instagram, once remarked on stage, paraphrased: “When the iPhone 4 launched, most people saw a phone with a great camera — we... Read More

Last December, I got into a longer conversation at a social event with someone who had lots of corporate M&A experience in tech. She said something to me that lodged into my brain: “Generally speaking, we have no interest in VC prices.” As that quote snaked... Read More

Earlier this summer, I was catching up a friend who’s at an early-stage fund. He said something which has stuck with me, paraphrased: “We try to tell ourselves all the time — we need to be the folks willing to have the hard conversation —... Read More

Last weekend, a number of people shared the first-person account of millennial “side-hustling” that was published in Quartz. You can read the article here. It’s not that great of a piece, nothing new or earth-shattering is revealed, but I’d wager it was shared so widely... Read More

About a year ago, my friend in NYC Joel pinged me about a company he had invested in. It was a short description, but I took the intro and met Jeff, the CEO of Tempo Automation, for coffee. We had a great discussion, and he... Read More

Disclaimers: This isn’t a doom and gloom speech. There’s tons of opportunity out there. And, this is mainly focused on consumer markets. Also, this post is a little long in the tooth. Please forgive me. I haven’t had time to write with all the little... Read More

The first notification which caught my bleary eyes Monday morning — Microsoft to acquire LinkedIn for $26 billion. Much has been written about why this may make sense for Microsoft. What’s less clear is: What motivated LinkedIn to take this path? I’ll attempt to answer... Read More

(Disclaimer: Before a writer rips me apart or tweets this post without reading it fully, I used to be a long-time columnist for TechCrunch (the most frequent contributor they’ve ever had, over 100 posts and nearly 100 videos over a three period. I’m also a... Read More

People will sometimes stop and ask me, “How did you become an investor?” To which I usually reply, “I’m not a real investor — I just play one online.” It’s partly a joke, but there’s some truth to it — it’s easy to write a... Read More

There’s a lot of noise about what’s happening the private startup market. It’s easy to just say X and Y are happening and read the headlines. Today, I got an email from Industry Ventures (IV), which acts as an LP into various VC funds and... Read More

In the world between founders and investors, both sides should always be mindful of their interpersonal behaviors — especially being aware if the origin of each relationship is outbound, inbound, or mutually developed. In a situation where one experiences inbound interest, that person is often... Read More

I love Medium, the product. I wish I had the opportunity to invest. When Greylock became their first institutional investor, I knew Medium would be a billion dollar exit and wrote about it here. Since then, other great investors and firms have backed up their... Read More

I intend to shift most (not all) of my focus back over to consumer investing in Haystack 3. In my first fund, it was dominated by consumer. That wasn’t intentional. I was just starting out, I was a dog chasing cars. In my second fund,... Read More

Nearly a decade ago, I met an investor while I was in Boston who was trying to explain to me how some very rich people like to invest. This is many years before I become interested in investing myself. He called it “The Chocolate Chip... Read More