My name is Chris Tsakalakis
I am a technology CEO and advisor with more than 25 years of experience developing and leading consumer technology businesses.
I am a 3 time CEO. My last CEO role was at Kiva, an international nonprofit that crowdfunds loans for underserved people in over 70 countries. Before Kiva, I was the CEO of Vivino, the world's largest online wine marketplace and most downloaded wine app. At Vivino, my team grew wine sales 2.3x in 2 years. Before Vivino, I was as an Entrepreneur in Residence at Benchmark Capital. Prior to that, I served as President of StubHub, the world's largest online ticket marketplace. Over 8 years at StubHub, my team grew the value of tickets sold from $400 million to $3.2 billion while doubling customer satisfaction and increasing brand awareness by over 50%.
Managing Partner at Trefo
Cook and intermediate sourdough bread baker
Obsessive user of Apple Watch to track my mediocre efforts at swimming and weight training
The Short Version
Born in Chicago to Greek immigrant parents
Worked at Bain & Company in Boston, Warsaw, Moscow and London
Moved to San Francisco in 1996
President of StubHub from 2007 to 2014
Entrepreneur in Residence at Benchmark Capital in 2016 and 2017
CEO of Vivino in 2018 and 2019
CEO of Kiva in 2021 and 2022
The Medium / Bio Version
Consultant, Advisor and Board Member
Chris has been a technology CEO and advisor for more than 25 years with experience developing and leading consumer technology businesses at Kiva, Vivino and StubHub.
Most recently, Chris was the CEO of Kiva, an international nonprofit that crowdfunds loans for underserved people in over 70 countries. Before Kiva, Chris was the CEO of Vivino, the world's largest online wine marketplace and most downloaded wine app. At Vivino, Chris' team grew wine sales 2.3x in 2 years. Before Vivino, Chris was an Entrepreneur in Residence at Benchmark Capital. Prior to that, Chris served as President of StubHub, the world's largest online ticket marketplace. Under his nearly 8 years of leadership, StubHub grew the value of tickets sold from $400 million to $3.2 billion while doubling customer satisfaction and increasing brand awareness by over 50%. Because of StubHub’s influence on the entertainment industry, Chris was named to the Sports Business Journal’s 2011, 2012 and 2013 lists of the 50 most influential people in the sports business, the Billboard 2012 and 2013 Power 100 lists and the 2010 and 2011 Huffington Post Sports Game Changer lists.
Chris led the acquisition of StubHub by eBay and began running StubHub in 2007, when the acquisition was finalized. Chris was an eBay Marketplaces executive from 2003 to 2014. Prior to joining eBay, he held management positions at two e-commerce startups, and was also a consultant with Bain & Company. He started his career in technology in 1996.
Chris graduated summa cum laude with a Bachelor’s degree in Economics from The Wharton School of the University of Pennsylvania. He serves on the board of directors for findhelp and the Western States Region of the American Heart Association. In his spare time Chris is a fitness and automotive enthusiast.
The Long Version
I was born shortly after my parents emigrated to the US from Greece. I grew up in the Chicago suburbs surrounded by family and many members of the Greek community. I went to Koraes Elementary, a Greek Orthodox parochial school connected to Saints Constantine & Helen Church, where I was an altar boy.
High School and College
From Koraes, I went to St. Laurence High School where I graduated co-valedictorian. I am part of the first generation in my family to graduate from high school.
Early Business Career
My first job out of college was at Bain & Company. I started as an Associate Consultant (analyst) in the Boston office and left as a Consultant (Associate) after working in the Warsaw, Moscow and London offices. In addition to the usual corporate strategy stuff, I got to work on the privatization of government owned enterprises in Poland and Russia in the early 90s. I also got to see armored personnel carriers roll down the Garden Ring in Moscow, but that's another story.
Bain taught me how to use data to analyze any business and make sound business decisions. And it also gave me a ticket to travel around Europe and work with some of the most talented people I know.
By 1995, I was tired of consulting and very interested in pursuing a career in the burgeoning Internet industry. When I told my London friends that, they would say "Oh yes, the Internet, I've been meaning to check that out."
I decided the best way for me to "check it out" was to move to San Francisco and that's what I did in 1996. My first job was the CEO of a startup called NonprofitAuction.com. We were selling online auction technology to charities. We were too early. It was my first attempt at being a CEO and I failed after 18 months of trying.
eBay and StubHub
When eBay bought StubHub, the world's largest ticket marketplace, in 2007, I was given the privilege to run the company for eBay. I did that until 2014. Over 8 years, we grew the value of tickets sold from $400 million to $3.2 billion and increased operating profit 15 times. Over the same time period, we expanded StubHub outside the United States and doubled customer satisfaction and employee engagement.
Benchmark Capital and Vivino
After spending 11 years at eBay Inc., I was ready for something new. I spent a lot of time looking for a role as good as the one I had at StubHub. Part of that journey was working as an Entrepreneur in Residence (EIR) at Benchmark Capital where I got to better understand how venture capital works and what investors look for.
After being pitched 120 CEO roles, I was lucky enough to take on that role at Vivino, the world's largest wine app and marketplace. While there, I hired a CFO and COO and the team accelerated sales to grow them 2.3x in 2019 vs. 2017. We also turned around unit economics from negative to positive and launched wine sales in 5 new countries.. And I raised $9 million in new funding.
After StubHub and Vivino, I realized I really liked technology and online marketplaces, but I had no interest in the industries I worked in - ticketing and wine. I wanted my next role to be at an organization that made a positive impact on the world and that's when the Kiva opportunity came to me.
While I was working full time, I was asked to help entrepreneurs at different companies. I really liked that experience and found that the CEOs I worked with were - unlike my children - interested in my experience and point of view. After leaving Kiva, I decided to focus full time on helping technology companies as an advisor, board member and consultant. I do that through my firm, Trefo, which means to nourish or nurture in Greek.
Along the way, I got married, had 2 sons and bought a house. Oh, and I lost my hair in case you didn't pick up on that from the photos. You know, grown up stuff.
The other grown up thing that happened to me was open heart surgery. It happened in 2009 to address a genetic valve issue. My wife and I ran a marathon 15 months later, and I continue to exercise regularly.
Because of my experience with heart disease, I became a volunteer for the American Heart Association (AHA) in 2011. I currently serve on the board for the AHA's Western States Affiliate.