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

Quickly Unpacking SAP’s $8B Acquisition Of Qualtrics

Qualtrics recently filed to go public. Last night, SAP bought the company before it could IPO. There are plenty of well-deserved articles by Axios and Forbes and tweets of praise for Qualtrics (must read Utah-based VC Bryce Roberts’ storm here), which you can and should... Read More

The Story Behind My Investment In People.ai

A few years ago, during a YC cohort (before Demo Day), a few sources told me about a SaaS founder in the batch who was on a mission. Once I hear a name or company a few times in a short period, I begin to... Read More

A New VC Crop of Series A Firms

Many of the most storied brands in venture capital made their name by being the investor of record in a specific company’s “Series A” round — largely thought of as the round after friends, after family, and more recently, after seed, where the new investor... Read More

The Market Holds The Best Fundraising Advice

As lines of code continue to proliferate through the world, as the rate of startup formation increases to seize those opportunities, and as the VC industry expands to support those new teams and opportunities, there is no shortage of people to visit for advice —... Read More

Reflections On The Big Shake-Up At Kleiner Perkins

For folks who know me, they know I’m obsessed with Twitter, but this week, I had so many work-related and personal/family things going on, I simply couldn’t keep up. That said, I did certainly see all the email subject lines this morning about Kleiner Perkins,... Read More

The Long Haul Of Building A Venture Capital Firm

There are countless posts flying around the web now about “How to build a startup.” It’s great that all this knowledge has made its way online. On a slightly smaller impact scale, there isn’t a lot of content out there about “How to build a... Read More