About

STARTUP INVESTING IS

— ONE OF MY THINGS 

BUT IT’S NOT MY EVERYTHING

The not-so-executive summary

You likely know me as an investor, advisor, entrepreneur, political activist, and that guy sometimes on Shark Tank. I am the Chairman of Lowercase Capital, and together with my wife Crystal English Sacca, we have invested in dozens of early stage companies that include some now iconic names like Twitter, Uber, Instagram, Twilio, Stripe, Kickstarter, and even Blue Bottle.

Yet, in early 2017, I announced I was stepping back from making new investments so I could focus on our ongoing efforts to rescue democracy, heal the planet, promote diversity within venture capital and technology, and reform our criminal justice system. In parallel, I dedicate a lot of time, energy, and funding to entrepreneurs building philanthropic startups such as charity:water, the Anti-Recidivism Coalition, Global Citizen Year, and many more listed here.

This whole venture capital thing started when I left the perfect gig at Google to break out on my own. As Google’s Head of Special Initiatives, I founded and headed up Google’s Access division including our multi-billion dollar 700MHz and TV white spaces spectrum initiatives, the company’s groundbreaking data centers in Oregon, Georgia, and the Netherlands, and Google’s free citywide WiFi network in Mountain View, CA. I also led many of Google’s business development and M&A transactions and was on the founding team of the company’s New Business Development organization. In recognition of my work, I was among the first Google employees ever given the Founders’ Award, Google’s highest internal honor.

Things went really well for me at Google. I was given the room and the resources to shake things up at scale. Along the way, I wrote my first checks to seed stage outfits like Photobucket (acquired by Fox Interactive) and Twitter. I also led Google’s seed investment in Meraki which later sold for $1.2 billion. But despite a very cool internal culture, Google started to feel like a big company and I knew I was happiest when working with founders in scrappier environments.

So, in the Fall of 2007, when I told Larry, Sergey, and Eric I was leaving to go work with startups, I was just following my gut. I didn’t have a plan nor enough money to be a professional investor. I soon worried I had made the biggest mistake of my life. Yet, I was passionate about this new wave of entrepreneurship that allowed founders to just start coding without first raising millions of dollars, and I knew I wanted to get right in the middle of all that. I was confident I could help these new companies.

The performance of those investments made me one of youngest members of the Forbes “Midas List” in 2011 and I climbed every year since, ultimately landing in the #2 spot in 2017. I’ve been on a bunch of other lists along the way, but my favorite hands down is when my trademark cowboy shirts earned me a spot on GQ’s ”Worst Dressed List.”

Alongside all of these professional pursuits, I was deeply involved in Barack Obama’s 2008 presidential campaign. I worked as a speaking surrogate, advisor, field office volunteer, Co-Chair of National Finance, and a Trustee of the Presidential Inaugural Committee. During the reelection campaign in 2012, I continued my work as a National Finance Committee member, a host of the President’s roundtable discussion series, and as Co-Chair of Tech for Obama. Since the events of November 2016, I count myself as a proud and active member of the #resistance and I am dedicating countless dollars and hours in hopes of helping this country through some dark days.

Meantime, you know I have never shied from sharing my opinions about anything, so I have spent years as a loud and candid fixture on television, radio, and podcasts. Some of my favorites are collected here. A couple years ago, I joined the cast of Shark Tank for two Emmy Award-winning seasons where I loved being a thorn in the side of Mark Cuban and Kevin O’Leary.

Not enough bio for you? Want to go back a little farther? Early in my career, I was an attorney at the Silicon Valley firm of Fenwick & West, where I worked on venture capital, mergers & acquisitions, and licensing transactions for technology giants. (Let’s keep this whole me being a lawyer thing between us.) Then I served in various executive roles at one of the world’s largest streaming and digital media companies, Speedera Networks (acquired by Akamai Technologies).

Turn the book back a few more pages and you’ll find I graduated cum laude from the Edmund A. Walsh School of Foreign Service at Georgetown University and was an Edmund Evans Memorial Scholar as well as a Weeks Family Foundation Scholar. Undergrad is where Crystal and I met and were classmates. (She often reminds me that her GPA was .02 higher than mine.) Earning my Foreign Service degree included plenty of time abroad attending the Universidad Católica del Ecuador in Quito, Ecuador, University College Cork, in Cork, Ireland, and the Universidad Complutense in Madrid, Spain. From there, I went on to graduate cum laude from Georgetown University Law Center where I was a member of The Tax Lawyer law review and was honored as a Philip A. Ryan and Ralph J. Gilbert Memorial Scholar.

I’ve also been an Associate Fellow of the Said Business School at Oxford University, an MIT Enterprise Forum Global Trustee, an Atlantic Council Vanguard 25 member, and a longtime Henry Crown Fellow at the Aspen Institute. Long before any of that, beginning in 7th grade, I attended night school at the State University of New York at Buffalo for years of college mathematics classes wearing thick glasses, awkward braces, and knowing the entire time that technology and computers would always be passions of mine.

These days, I live with my wife Crystal and our three gutsy girls near the ocean and in the mountains. Alpine and nordic skiing are religious pursuits for me. I’m also a kitesurfer, helicopter enthusiast, recovering Ironman triathlete, average-proficiency crossword puzzler, and I have bicycled coast-to-coast across the United States of America.