Who

Yossi (Joseph) Essas, a leading technology expert, venture capitalist, and mensch.

What

Yossi is the chief technology officer at OpenTable, an online restaurant reservation service that seats over 100 million people per month in 50,000 registered restaurants (including 80 kosher restaurants). Responsible for all product development, software design, and online solutions, Yossi oversees 500 employees across four countries: US, UK, Australia, and India. In addition, Yossi is a venture partner at FirstMark Capital, a top-tier venture capital fund based in New York City, whose investments include Airbnb, Shopify, Pinterest, and InVision.

Where

Born in Moscow, Yossi moved to Israel as a teenager, and then relocated to L.A. with his wife shortly after his marriage. With his company in San Francisco, his venture capital fund in New York, and his business contacts all over the world, he travels a lot — 250 flights last year alone!

Why

I’m fascinated by Yossi. Not only is he super-successful in his career, but he is also committed to leading a Torah-centered life and passionate about helping the Jewish community. Moreover, he’s very well-rounded: he skis, plays golf, and is somewhat of a chess whiz; when he was younger, he placed third in a Moscow city championship. Finally, because of his family’s dramatic story, Yossi is enthralled by Soviet Jewry in the 1970s and 80s, collecting hundreds of books, stories, and biographies on the topic.

1 of 9 What opportunities or personalities played a role in your career?

My father, Rabbi Eliyahu Essas, was the leader of the baal teshuvah movement in Russia in the 1970s and 80s. He had hundreds of students, and thousands of people were impacted by his work. He ran Gemara shiurim, Chumash classes, summer camps — all under the radar of KGB and Russian authorities. ArtScroll published his biography by Miriam Zakon, Silent Revolution, in the 1990s.

In the Geneva Summit of 1985, President Ronald Reagan asked Mikhail Gorbachev to let my family emigrate from Russia to Israel. To show America that he takes human rights issues seriously, Gorbachev acquiesced. So after 13 years of refusing to let us go, we were asked by the KGB to pack our bags. We arrived in Yerushalayim in January 1986.

I went to chareidi high schools, learned in Yeshivas Ateres Yisroel, and subsequently studied computer science at Machon Lev. I served four years in the Israel Defense Forces, first as a tank commander, then as a software developer for missile recognition in tank shooting systems. After the army, I joined a Tel Aviv startup, developing software for remote learning. I got married in 1996 and moved to Los Angeles two years later, where I joined the startup scene of newly-formed Internet companies.

I always liked the intersection of technology and business. I enjoy solving real world problems using technology, and as a result, I always focused on user-centric solutions. I was very fortunate to work for A-list companies, where I’ve picked up these skills. I believe that in every profession there are A players and B players, and you should always be exposed and learn from A players. One of my early managers asked me: Would you rather be a starter on a D-League or a bench player on an NBA team?

As my career in Silicon Valley progressed, I became more involved in venture capital. I’m a venture partner in FirstMark Capital in New York, as well as a personal investor in several companies. Before I invest, I need to know that the people behind the company are smart, experienced, and can adjust with the business. I believe in investing in people, not ideas. Everyone has ideas; execution is what’s really hard. People who know how to execute will succeed even with a not-so-great idea.

Recently, when my dear friend Effie Goldberg decided to leave a decade-long career in NCSY to help teens struggling with addiction, I became very interested in how technology can help kids in areas of mental health. I think this area is not developed, leaving a lot of potential for doing things differently and using data, sophisticated artificial intelligence systems, and better processes. That’s why I’m now a partner in Ascend Healthcare, which provides residential treatment to teens with mental health and addiction issues.

 2 of 9 Which three character traits have played a key role in your career path?

Confidence. Someone told me many years ago, “Whatever you do, you will never fail; you will just learn what works and doesn’t work.” I think this is the key to success. People are afraid of failure, of disappointment, so they don’t act. If you internalize that there’s no such thing as failure, just learning opportunities, you can accomplish anything.

Hard work. I’ve discovered that no one succeeds just because he works hard. However, people mostly don’t succeed when they put no work into something. So hard work alone will not get you there, but it’s a necessary ingredient to success. You need to know what problem you’re trying to solve, you need to have a plan — and then you need to work hard to execute it.

Finding good people. No one succeeds alone. You’re only as successful as the people you work with. Associate with smart, successful people, and it will rub off on you. The opposite is true too; the wrong people will drag you down. Invest in your skills to identify, partner with, and connect with successful people.

3 of 9 What do you do to relax, recharge, or simply have fun? How do you make time for that, and how often?

Shabbos is my most relaxing day of the week. Disconnecting from all the tweeting and pinging and ringing is incredible. It lets me clear my mind, readjust, and refocus on what’s important: family, Yiddishkeit, friends. I think Shabbos is our secret weapon in many ways, and of course, Shabbos is the source of brachah.

We also like family vacations. Taking myself out of my regular environment, going to a different place, and experiencing different surroundings, languages, and cultures is incredibly uplifting for me.

5 of 9 If you were granted an extra three hours per day or a spare million dollars, what would you do with that time or money?

I would teach computer science in a mesivta or a Bais Yaakov. Today, education is critically important for success, and we often don’t do a good enough job preparing boys and girls for the inevitable need to make a parnassah. Some stay in learning, but a large percentage will have to earn a living eventually. We don’t pay teachers well, and we don’t teach the right topics for today’s world needs — so I would try to make a difference there. The ability to interact with computers and the skills to program and write code are prerequisites today for many good opportunities; these skills are as important as math or English.

6 of 9 What is the most inspiring feedback you’ve ever received? Did that impact what you did next?

Not sure about inspiring. But this was very useful feedback to me: “People don’t change. They just become better actors.” This was Yahoo’s chief technology officer, telling me to stop pretending that I can change someone who was underperforming in my group. This message stuck with me. I believe there is some truth to it; if an individual has certain character traits or talents, most likely you can’t change those, so choose to work with people who are compatible with your needs.

8 of 9 Can you share a time when you had to navigate the tension between your deepest values and the business world?

Four years ago, Booking Holdings — an $80 billion public company — was buying OpenTable. We worked on this huge deal for months, and Booking Holdings’ chief executive officer was flying in from Amsterdam for some final discussions.

The date was set: Shavuos. I obviously informed our CEO that I would not be attending. He couldn’t believe it. He tried to convince me, threaten me, guilt me — nothing helped. I was not going to be there. It was tense.

At the end, since Hakadosh Baruch Hu runs the world, everything worked out. During Yom Tov — unrelated to me — the meeting got postponed. The sale eventually went through (for $2.6 billion), and everything turned out okay. Needless to say, I told my kids, “Here is an example of how Hashem runs the world. You do what you need to do, and He will turn everything around to make it work.”

9 of 9 If you were advising a young man/woman hoping to launch a career as an entrepreneur, which “dos” and “don’ts” would you share?

The danger of any professional involvement, especially if you’re passionate about the topic, is that it can suck you in 150 percent, making you lose sight of what’s really important in life: family, Yiddishkeit, community. So do establish any mechanism you can for routine involvement in your community, to maximize time with your family, and to be kovei’a itim.

My company has offices all over the world, so I travel a lot. I make a point to always be home for Shabbos, to use technology tools to stay in touch with my kids, to be involved in community affairs, to learn (flights are fantastic time for learning) — all with the sole purpose of not letting work be the primary force in my life.

Originally featured in Mishpacha, Issue 752. Moe is the founder and CEO of Winfluencers, an early-stage start-up that empowers micro-influencers to monetize their passion. Previously, he was the head of BizDev for Hometalk, strategy consultant for Deloitte, and regional director for the Lauder Foundation. He holds an MBA and semichah, and published his first book, The Gift of Stuttering (Mosaica Press, 2016). He also teaches a daf yomi shiur, produces inspirational videos for Aish.com, and gives lectures to audiences worldwide. Moe lives in Ramat Beit Shemesh with his wife and children.