Shtark Tank

Yaakov Wolff
  • 4.9 (38)
  • Judaism
  • Updated Weekly

If you are a Ben Torah in the workforce, this is the podcast for you! Make sure to check out ShtarkTank.org for more meaningful content. You can access bonus content and community events through our quiet Whatsapp Group https://chat.whatsapp.com/B5jEcBP5umZAHWk2ILBWTS Feel free to reach out with feedback, or just to say hi: yaakovwolff@gmail.com

  1. Both Quit Tech Jobs? Shlomo Ashkanazy & Ami Yunger on Leaving Stable Careers to Serve the Jewish People

    9h ago

    Both Quit Tech Jobs? Shlomo Ashkanazy & Ami Yunger on Leaving Stable Careers to Serve the Jewish People

    What happens when you have a good job, mentors you trust, and a clear path forward — and you walk away anyway? Shlomo Ashkanazy (Co-Director, WashU JLIC) and Ami Yunger (COO, Mizrachi Canada) both built careers in the Israeli tech world before pressing pause to go on shlichut in North America. Neither choice was obvious. Neither was painless. And neither of them regrets it — mostly. In this conversation, they unpack the real calculus behind leaving stability for something harder to define. From their shared roots at Yeshivat HaKotel and OurCrowd, to navigating anti-Semitism on a college campus and in Toronto's streets, to Shlomo's gut-wrenching decision on Simchat Torah 2023 about whether to board a plane back to Israel — this episode doesn't stay on the surface. What we talk about: Why both of them credit OurCrowd — and its mission-driven culture — as the bridge between tech and shlichutThe nonlinear career path: real talk about professional anxiety, histadlus, and bitachonAmi on being COO of a Jewish nonprofit and why "COO" isn't just a fancy title for a shaliachShlomo on starting WashU JLIC from scratch — and what happened when 50 students showed up to his empty house on October 9th, 2023The anti-Semitism reality in Canada: bullets through shul windows, hiding event locations until 10 minutes before showtime, and how you maintain Zionist pride when it's being weaponized against youShlomo's still-unresolved guilt about not getting on a plane after October 7thThe 40-year test: how do you make a decision when the downside isn't catastrophic, but the stakes feel enormous?Guests:Shlomo Ashkanazy is Co-Director of JLIC at Washington University in St. Louis, which he and his wife founded as the inaugural couple. Ami Yunger is COO of Mizrachi Canada, where he supports the organization's growth across programming, operations, and community.

    42 min
  2. Ami Tobin on Losing His Mother, Finishing His Sefer in Miluim, and the Chinuch Career He Almost Chose

    Jun 8

    Ami Tobin on Losing His Mother, Finishing His Sefer in Miluim, and the Chinuch Career He Almost Chose

    Ami Tobin was faced with a descision: He had a week full of 8 hour shifts, guarding an outpost in miluim. How was he going to use that time? Watch the NBA Finals? Or something more meaningful? He pulled out his notes. And by the end of that week, his sefer — Amech Dodi — was fully edited. Both Hebrew and English. That story is a window into who Ami Tobin is. A Beit Shemesh kid who grew up watching his mother trade a PhD in psychology for a life of teaching Torah. A Givati soldier. A HiBob customer success manager. A husband of a wife who finished medical school during wartime. And a young man who lost his mother, Dodi Tobin z"l, to cancer — and turned years of Friday-afternoon Divrei Torah into a published sefer in her memory. In this episode, we talk about what nearly 300 days of Milluim actually costs you professionally, how Torah identity survives the grind of the tech world, and what it looked like to watch his mother face illness with a level of emunah that only grew stronger as things got harder. Her message: Torah isn't just practice. It's the lens everything else passes through. Topics covered: Growing up in Beit Shemesh with parents who were growing alongside himYeshiva Ma'alot, Givati, and finding a Torah identity worth keepingStumbling into tech via HiBob — right place, right time~300 days of Milluim and what it does to a career (and a person)His wife finishing medical school during wartime — the real superstarDodi Tobin z"l: her pivot from psychology to Torah, her emunah under pressure, and the Shabbat-vs-client-call storyWriting Amech Dodi — Divrei Torah collected since yeshiva, edited on guard duty, published l'ilui nishmatahThe women's Beit Midrash being built in Beit Shemesh in her memoryLinks: Amech Dodi on Amazon: linkBeit Midrash building fund: link

    37 min
  3. Torah Only? Torah Im Derech Eretz? ft. Rav Rafi Dembovsky

    Jun 1

    Torah Only? Torah Im Derech Eretz? ft. Rav Rafi Dembovsky

    What does Hashem actually want from us, a life of total immersion in Torah, or engagement with the world?This is one of the oldest machlokos in Jewish thought. And Rav Rafi Dembovsky was torn. He struggled with the issues, and wrote a book with his findings. You can order it here. Episode Description Rafi was raised in Edgware. Educated at Hasmonean. Spent years all-in at Torah-only yeshivos and kollel. Then came time to choose a school for his son — and the tension he'd quietly carried for years exploded into a full-blown existential question. So he went back to the sources. And wrote a sefer. We trace Rafi's personal journey alongside the intellectual one — from teenage brachos in Bnei Brak to law school at Hebrew University. We get into the sefer itself, the haskama drama, and the Rabbanim who quietly loved it but wouldn't sign their names. In this episode: Torah-only as a mindset, not just a lifestyle choiceThe Rashbi/Rabi Yishmael machlokes — and what it really means for how you liveWhy the Rambam wasn't who you think he wasThe four-point email telling him not to publish — and what he did nextLeaving kollel for law school: pshat or cop-out?

    34 min
  4. Ashi Taragin (Rabbi, Dr.) Didn't Become a Rosh Yeshiva

    May 25

    Ashi Taragin (Rabbi, Dr.) Didn't Become a Rosh Yeshiva

    Ashi Taragin had every reason to stay in yeshiva. He grew up breathing Torah. His father is Rabbi Reuven Taragin. His mother is Rebbetzin Shani Taragin. He made a Siyum HaShas at his Bar Mitzvah.Yet he didnt choose a career in Chinuch. Today he's an ER doctor at Sharei Tzedek, a lawyer, a mohel, and a sofer. He's also the unofficial rav of the emergency room, fielding end-of-life shailos in real time. And he still teaches Torah — but entirely on his own terms. In this episode, Ashi breaks down his version of the Rambam model: why financial independence from Torah makes your Torah better, what it means to be a baal habayis as a zechut rather than a compromise, and why he thinks sitting and learning all day isn't what Hashem put you here to do. Make sure to check out our newsletter and subscribe: ShtarkTank.org

    27 min
  5. Pulling Teeth, Publishing Torah (and a Shavuos Conversation on Megillas Rus) ft. Dr. Reuven Mohl

    May 18

    Pulling Teeth, Publishing Torah (and a Shavuos Conversation on Megillas Rus) ft. Dr. Reuven Mohl

    What does it take to build a serious Torah legacy while running a thriving dental practice in Manhattan? Reuven Mohl has spent the last decade doing exactly that — and the results are five published books, a growing body of scholarship, and a model for what it looks like to take your Torah life seriously without stepping away from the working world. In this episode, Reuven walks us through his upbringing in Manhattan Beach, Brooklyn, where his father Rabbi Oscar Mohl — a philosophy professor, Holocaust survivor, and talmid of the Baba Vredi — set the tone for a home where Torah and ideas were always on the table. From Yeshiva Flatbush to Yeshiva HaKotel to YU, Reuven shares how his years of learning shaped both his character and his career path into dentistry. We talk about the discipline behind building a successful practice, how he carved out time for serious learning between patients, and what led him to compile commentaries on the Haggadah, Megillas Rus, and Tehillim using the writings of Rabbi Eliezer Berkovitz and Rabbi Joseph B. Soloveitchik. And in honor of Shavuos, we learn together. Reuven shares a beautiful lesson from Megillas Rus on the difference between din and lifnim mishurat hadin — and what Boaz's generosity in the field teaches us about how to show up at work, at home, and in life. Topics covered: Growing up with a philosophy professor father and a Holocaust survivor in the homeThe work-life balance reality of a dental careerHow to pursue serious Torah scholarship while running a businessBuilding commentaries using the Rav and Rabbi BerkovitzMegillas Rus and the obligation to do more than the minimumThe story of calling before Shabbos

    44 min

  6. May 11

    Are You Past Your Peak?

    A Shabbaton in Bnei Brak. Two rabbis. A machlokes I have been wrestling with ever since. One rav told a room full of 18-year-olds that they were living the climax of their lives. Another rav pushed back. Both left a mark. In this solo episode, I share the audio version of my most-responded-to piece of writing to date — a post that starts the process of distilling over 120 episodes of Shtark Tank into one central question: what does it mean to serve Hashem during the working chapter of life? Subscribe to our newsletter at ⁠ShtarkTank.org⁠ We cover the surprising lesson buried in the Matan Torah story, the unique mitzvos that come alive when you enter the workforce (Shabbos, Kiddush Hashem, Yishuv Olam, Talmud Torah), and why this stage of life isn't a regression from the Beit Midrash, it's its own chapter, loaded with opportunity. Plus: a beautiful piece of listener feedback from Ruben Melman, a recent Yeshiva graduate about to start his first job, and my own honest reflection on what it felt like to pack up the sefarim boxes.

    17 min
  7. Why This CMO Learns Tanach Every Morning at 4:30am ft. Moshe Isaacson

    May 4

    Why This CMO Learns Tanach Every Morning at 4:30am ft. Moshe Isaacson

    Moshe Isaacson is a marketing executive and go-to-market leader in the SaaS world — and one of the most passionate Tanach learners you'll ever meet. In this episode, Moshe makes the case for why Tanach is the most underrated limud in the Torah world, how his love for it was ignited on hikes through Eretz Yisrael, and why he wakes up at 4:30am to prepare the three weekly shiurim he gives to his community. Topics covered: Growing up in Pittsburgh — a broad, out-of-town community that exposed Moshe to every type of YiddishkeitHow a yeshiva in Eretz Yisrael turned Tanach from stories into living heritageWhy Tanach gets second billing in the yeshiva world — and why Moshe thinks that's an avlaThe Maskilim and Zionists claimed Tanach as their own. Moshe's response: that's exactly why we need to take it backHow Moshe got into marketing entirely by accident, starting at IDT and building from thereThe overlap between psychology, marketing, and Torah — and why pattern recognition is the common threadBalancing a demanding career with three weekly shiurim, a daily chavrusa, and serious limud preparationThe 4:30am wake-up, the one-hour train commute, and how Moshe engineers his day around learningA practical challenge: 929 perakim, one a day, finished in under three yearsSefer Shmuel as his favorite — four years learning and teaching itWhere to find his podcast, Tanach in Depth, and his AI-generated Torah content To follow Moshe's Torah: https://open.spotify.com/show/3G2IJ0opltMtTlrsTioQVg?si=SAg8yci3QTeK99v8qWRWcQ https://x.com/isaacson Sign up for our newsletter @ ShtarkTank.org

    41 min
  8. Jon Medved Is Not Done Yet | OurCrowd Founder & Startup Nation Pioneer

    Apr 27

    Jon Medved Is Not Done Yet | OurCrowd Founder & Startup Nation Pioneer

    Jon Medved has spent decades building Israel into a global technology powerhouse, helping fund hundreds of companies, bringing billions of dollars into the Israeli economy, and playing pivotal role in what eventually became the Startup Nation brand. Then he flatlined in a hospital for eight minutes. In this episode, Jon sits down with Yaakov Wolff to talk about growing up far from Judaism on the beaches of California, the unlikely path that brought him to Israel, and why he believes the Avot were the original entrepreneurs. He makes a bold case that building companies, solving the world's problems through technology, and living as a proud Torah Jew are inseparable. He also opens up about his ALS diagnosis, what it felt like to be brought back after flatlining, and why, at this stage of his life, he's more driven than ever. In this conversation: From Berkeley to Jerusalem — Jonathan's winding path to Aliyah and observanceThe PowerPoint that seeded Startup NationWhy the Avot were all entrepreneursTechnology, Torah, and where the two meetLiving with ALS and refusing to stop"I'm not done. There's still what I have to accomplish." For exclusive written content, subsribe to our newsletter at ShtarkTank.org

    33 min
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4.9
out of 5
38 Ratings

About

If you are a Ben Torah in the workforce, this is the podcast for you! Make sure to check out ShtarkTank.org for more meaningful content. You can access bonus content and community events through our quiet Whatsapp Group https://chat.whatsapp.com/B5jEcBP5umZAHWk2ILBWTS Feel free to reach out with feedback, or just to say hi: yaakovwolff@gmail.com

Information

  • Creator
    Yaakov Wolff
  • Years Active
    2024 - 2026
  • Episodes
    129
  • Rating
    Clean
  • Copyright
    © Yaakov Wolff
  • Show Website
    Shtark Tank

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