New beginnings are hard.

Shtark Tank went live at Yeshiva University Israel in Beit Vagan, recording in front of a room full of YU summer interns spending their summer working in Israel. The theme: new beginnings and transitions, and what it actually takes to navigate them.

Part 1 is a panel conversation with threeShtark Tank All-Stars, who have each made their own version of the leap from the beit midrash to the workforce.

Rabbi Reuven Berman is a rebbe, business owner, and CEO of Kobe IP. Zevi Reinitz is a founder, marketing executive, and author of 14 Sefarim. Moshe Rapps is a client advisor at Bernstein Private Wealth Management, an EMT, a podcaster, and a baseball coach.

Together they get into the unwritten rules of workplace communication that no one teaches you, how to stay true to your values without wearing them like armor, why relationships are the only career asset that compounds forever, and what it really means to reinvent yourself when the world is moving faster than your LinkedIn profile.

In Part 2, Shaun Regenbaum joins the conversation. Shaun is a PhD candidate at Hebrew University in bioengineering, founder and CEO of PropheX, and one of the more fascinating people you'll hear on this show. He built a Talmud lab in the middle of Georgia Tech, started his first company as an undergrad out of pure necessity, and has been quietly building one of the most interesting Torah and AI projects around at Talmud.dev.

Shaun talks about what entrepreneurship actually feels like from the inside, why he doesn't recommend it for everyone, how he navigated being the only shomer Shabbat Jew at a major research university, and where he sees Torah and technology heading.

Recorded live. Real audience. Real questions.

Teddy Berman grew up in the Syrian community in Flatbush, went to college, worked in finance — and then got the itch. Almost ten years of learning later, he's back in the driver's seat, building a family in Yerushalayim and trying to figure out what comes next.

In this bonus episode, Teddy reaches out with the questions a lot of guys have but don't always get to ask directly: How do I balance parnasa with a serious morning seder? Is the dream of American hours realistic? Does it matter if I'm a working person or a mashpia by the bima? And how do I even figure out what I'm cut out for?

We get into all of it — including the recruiter who laughed in my face, why Rav Yonasan Sacks's career advice puzzled me as a bochur in KBY, and why knowing yourself is the most underrated job search tool there is.

Also: what Aliyah really means for your community, your nusach, and your kids — and why "choosing a box" might be the wrong frame entirely.

If you're somewhere between the beis medrash and the boardroom, this one's for you.

Topics covered:

• Hishtadlus, bitachon, and the Ramban on going to war
• Ahavat melacha — what Chazal actually say about loving your work
• Soft skills vs. marketable skills: the honest breakdown
• Using AI for career self-reflection (Teddy's been doing it)
• Building community in Eretz Yisrael as an Anglo oleh
• Dati Leumi vs. Haredi — more nuance than you think

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 shlichut
• The nonlinear career path: real talk about professional anxiety, histadlus, and bitachon
• Ami on being COO of a Jewish nonprofit and why "COO" isn't just a fancy title for a shaliach
• Shlomo on starting WashU JLIC from scratch — and what happened when 50 students showed up to his empty house on October 9th, 2023
• The 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 you

• Shlomo's still-unresolved guilt about not getting on a plane after October 7th
• The 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.

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 him
• Yeshiva Ma'alot, Givati, and finding a Torah identity worth keeping
• Stumbling 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 superstar
• Dodi Tobin z"l: her pivot from psychology to Torah, her emunah under pressure, and the Shabbat-vs-client-call story
• Writing Amech Dodi — Divrei Torah collected since yeshiva, edited on guard duty, published l'ilui nishmatah
• The women's Beit Midrash being built in Beit Shemesh in her memory

Links:

• Amech Dodi on Amazon: link
• Beit Midrash building fund: link

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 choice
• The Rashbi/Rabi Yishmael machlokes — and what it really means for how you live
• Why the Rambam wasn't who you think he was
• The four-point email telling him not to publish — and what he did next
• Leaving kollel for law school: pshat or cop-out?

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.

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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 home
• The work-life balance reality of a dental career
• How to pursue serious Torah scholarship while running a business
• Building commentaries using the Rav and Rabbi Berkovitz
• Megillas Rus and the obligation to do more than the minimum
• The story of calling before Shabbos

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?

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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.

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 Yiddishkeit
• How a yeshiva in Eretz Yisrael turned Tanach from stories into living heritage
• Why Tanach gets second billing in the yeshiva world — and why Moshe thinks that's an avla
• The Maskilim and Zionists claimed Tanach as their own. Moshe's response: that's exactly why we need to take it back
• How Moshe got into marketing entirely by accident, starting at IDT and building from there
• The overlap between psychology, marketing, and Torah — and why pattern recognition is the common thread
• Balancing a demanding career with three weekly shiurim, a daily chavrusa, and serious limud preparation
• The 4:30am wake-up, the one-hour train commute, and how Moshe engineers his day around learning
• A practical challenge: 929 perakim, one a day, finished in under three years
• Sefer Shmuel as his favorite — four years learning and teaching it
• Where 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

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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 observance
• The PowerPoint that seeded Startup Nation
• Why the Avot were all entrepreneurs
• Technology, Torah, and where the two meet
• Living with ALS and refusing to stop

"I'm not done. There's still what I have to accomplish."

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