Yaakov (Jeffrey) Greenman, a two-time alumnus of HTC (FYHS 01’, HTC 04’), was born in Los Angeles, California and raised in Houston, Texas. After dorming at FYHS for high school, Yaakov attended HTC for college, where he received a Bachelor of Arts degree in Judaic Studies and Computer Science. He currently lives in Riverdale, NY, running a software consulting company for the last 15 years. Yaakov has been involved in the venture capital finance space in New York, mostly launching various startups in the media space. He has worked for many Fortune 500 companies in New York City, including Disney, CBS, the Hollywood reporter, Sports Illustrated, and more, mostly as an enterprise architect or a technical developer on various websites or projects. He has helped launch Fox News Digital’s foxbusiness.com website, he has run weightwatchers.com for 3 years, and he is currently a member of the technical consulting group at Bottle Rocket, a unit of Ogilvy, launching websites and creating digital transformations.
According to Yaakov, his interest in software and programming dates all the way back to his days in the Skokie Yeshiva. “I had interest so Rabbi Isenberg and I decided that I would work on the htc.edu website. I kept up with it all these years. I supported and maintained the site for 18 years or so, including the years I was in college. I was able to put that on a resume which was helpful.” With the experience he gained, Yaakov went on to work with virtualJerusalem.com, one of the first hybrids between a Jewish admin and a developer, and one of his first entries into the space. He later entered the video camera space, creating a startup in online video editing. Fox News, seeing and liking the software, decided to use it for advertising purposes and to have and present proper analytics, which was great for tracking. “Being able to help with advertising purposes, especially that early on in the advertising online video was really great experience,” said Yaakov. “I think that interestingly, being involved in HTC.edu was a really great project for me and was very challenging. Although at the time it was very basic, we still were trying to compete with other universities that were out there which gave me great experience in the space.”
While the Yeshiva nurtured his interest in software and programming, his connection to Skokie goes far beyond the classroom. “My grandfather, Rabbi Paul Greenman, was a rebbe from 1967 - 1970 and in 1970-1984 he went from at first being the Assistant Hebrew Principal and then became the Secular Studies Principal. My father went to Skokie, my great grandfather went to Skokie, and my grandfather’s father-in-law also received his second Semicha in 1925 from Bais Medrash L'Torah. I have a lot of Chicago roots in that sense.” When it came time to pick a high school, aside from his Skokie roots, to Yaakov, the Yeshiva just made sense. “At the time, Rabbi Wender was the principal in Skokie and his brother was my Rabbi in Houston. I used to see Rabbi Wender a lot when he would come to Houston and I would speak with him every so often. I knew I wanted to go away for high school since Houston was a very small community at the time and I wanted to learn more, so I was really excited about the dorm and to be able to be independent in a way.”
Ultimately, Yaakov decided to spend high school at the Yeshiva. “High school was a lot of fun,” he said. “It was a good mix of being in the dorm and being able to have pick up baseball games, just go into a friend’s room and hang out with a friend. That part was an amazing experience. It was almost its own little mini community besides your class. I was a big learner at the time and my experience was very much oriented that way. Overall, I’d say I learned how to learn from high school itself. It was really a very open-minded and worldly type of learning. College was a bit more challenging because you had two curriculums, but it was actually really great for when you get into the work force. The learning in HTC was challenging and that’s something I appreciated a lot.”
Something that Yaakov looks back on fondly is the relationships he was able to develop with his rebbeim as friends and mentors outside of the classroom. “Rabbi Polstein used to have the senior boys over at his home to talk and have group discussions. He’d ask a thought provoking question and asked us our thoughts. I remember that was one of the few moments where I felt like we really got into life-applicable things. I remember one conversation was just whether a Jewish education something that helps you prepare for the future. People would go around the table and talk about what they thought and if a Jewish life was meaningful for them. Those types of in-home meetings were really powerful and stuck with me. I think about them from time to time in moments of challenge. Being in the media industry was not easy. Being an orthodox Jew, you have to make sure that you have grounding when you go into some of these spaces.”
For Yaakov, that personal attention to a student’s wellbeing was a theme that was common among many of the rebbeim. “Rabbi Ginsbarg, in my freshman year, really cared about our social and psychological wellbeing. He tried hard to make sure you were happy and healthy, which was so important to have in that first year. Lots of people impacted me that way. I would have great meetings with Rabbi Weiss, too. For me, it wasn’t so much about the classroom per se, it was about those intimate moments where they’d make time for you. Being a full-time dormer, it was just great to have that. College gave me more of an educational development whereas high school gave me that personal development.”
“What makes HTC/FYHS special,” said Yaakov, “is that utilizes Torah to give you a rich education. You learn how to learn, how to read gemara, you learn a lot of critical halachos and things like that, but beyond that, you have these rebbeim who are very worldly, reachable, and normal people to talk to. The organization as a whole and the rebbeim for me are people you want to emulate and be like. It was one of the best-balanced places I’ve seen throughout different organizations.”