Shtark Tank

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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This Yom HaZikaron, we sit with two fathers who lost their sons in the early months of the war.

Eitan Morell shares the story of his son Maoz — a kid with ADHD and learning difficulties who walked into a yeshiva that didn't want him, refused to leave, and became the kind of soldier his unit looked up to. Eitan reflects on what it means to suddenly see your child's whole life in reverse — and how grief reveals a person you thought you already knew.

Rob Airley shares the story of his son Binyamin — named best soldier in his platoon, loved by commanders and chaverim alike. The kind of guy who, moments before being killed, volunteered to run into a building because his unit needed him. Rob talks about learning to grieve without falling apart — and what it looks like to keep laughing and dancing in the house when Binyamin is no longer at the table.

We end off with exerpts from 3 other episodes, about the beauty of living in Israel. Shtark Tank episodes with Eli Freedman and Yaakov Ehrenkranz, and Yaakov's appearance on the DHR podcast hosted by Zak Lenik.

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To support Beit Binyamin click here

To watch the movie about Maoz Morell click here

Chapters:

00:00:00 Intro

00:04:20 Eitan Morell remembers his son Maoz

00:39:34 Rob Airley remembers his son Binyamin

01:11:25 Shtark Tank with Eli Freedman

0:1:23:17 Shtark Tank with Yaakov Ehrenkranz

01:33:24 Yaakov on DHR Podcast

Two years ago, we sat with Rav Asher Weiss and asked him some of the most fundamental questions a Ben Torah in the workforce can ask. I've returned to this shiur more than almost anything else we've put out — it's that dense with wisdom and direction.

Since then, the show has grown a lot, and I wanted to make sure newer listeners got a chance to hear it. And if you've already heard it? I think you'll get something new from it the second time around.

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Get ready for Pesach with a mega collection of divrei torah, from Bnei Torah in the workforce.

You will hear from Rav Yakov Danishefsky, Rav Jonathan Livi,Rav Max Berger, Zak Lenik, Mark Tobin Dr. Mordy Goldenberg and Yoel Van Messel.

At the end, you will hear some ideas of mine which I shared on The Greatest Parasha podcast, hosted by Raymond Ashkenazie and Emma Dayan

A big thank you to Shlomo Price for his help with extra editing.

Wishing you and your families a Chag Kasher Vsameach

Guest Bios and Links

Rabbi Yakov Danishefsky, LCSW CSAT, is a Chicago-basedtherapist and author of the widely read Attached, the newly released AttachedHaggadah, and the forthcoming sefer The Delight of Shabbos. He leads AvodasHaLev, a Chicago organization devoted to meaningful learning and communityprogramming, and hosts The Attached Life Podcast. He is known for bringingdepth, passion, and warmth to everything he teaches.

To order the Haggadah:

To order in US:

https://a.co/d/03dgzXKD

https://alehzayis.com/product/the-attached-haggadah/

https://feldheim.com/the-attached-haggadah

To order in E"Y:

https://siparti.co/attachedH/

Jonathan Livi is founder and Principal of RJL CapitalAdvisors, which places JV equity for middle market commercial real estate transactions across the United States. He is also the Hazzan and assistant rabbi at Shaare Rachamim Synagogue in Great Neck, NY, in which capacity heteaches Tanakh daily. His shiurim are available on Spotify and Apple Podcast via his various podcasts. He is married to Kayla, and father to 3 kids.

https://open.spotify.com/show/45srXeZZgZKHAomOmpIkmh?si=hf6h-z2dToezYb95H0dMxQ

https://open.spotify.com/show/48iHU4mP1cvgZOGFrC5Jys?si=JinlUNvmSeimGKQl9LWiMQ

Max Berger was an aspiring rabbi turned aspiring philosopherturned VC. He spent the last two years at Next Gear Ventures, a Tel Aviv basedearly stage VC fund, before moving back to New York this year.

ZakLenik  is a real estate advisor in Israel who works mainly with Anglos looking to buy a home andbuild a life here. His own aliyah journey didn’t start in the most typical way, but through years of learning—and later teaching—Torah, he developed a strongsense of purpose that ultimately brought him back to Israel for good. Now, he helps others navigate that same journey, combining real estate guidance with a deeper understanding of what it means to truly build a life here

https://www.instagram.com/zak_in_israel?igsh=YTU0MWRlbW5iMGMx&utm_source=qr

00:00 Intro

00:52 Rav Yaakov Danishefsky: Writing Your Own Story

18:08 Rav Jonathan Livi: The Revolution of Freedom

34:40 Rav Max Berger: Matzah and Authenticity

52:26 Zak Lenik: Freedom or Slavery?

01:11:12 Mark Tobin: The Holiday of Emunah

01:19:07 Dr. Mordy Goldenberg: Late Night Vision

01:25:51 Yoel Van Messel: Understanding Our Goals

01:38:40 Yaakov Wolff on Greatest Parashah Podcast

02:01:26 Outro

What happens when Torah, growth, and mental health start pulling against each other instead of working together?

In this episode of Shtark Tank, Yaakov Wolff speaks with Dr. Dan Jacobson — psychologist, musmach, co-author of Flipping Out, and author of Light in the Darkness — about stress, anxiety, yeshiva pressure, and the long-term impact they can have on our Avodat Hashem.

To recieve a free copy of Light in the Darkness, about kedusha in today's world, email [email protected]

They discuss the difference between healthy pressure and unhealthy stress, why anxiety seems to be rising in today’s world, and how formative yeshiva experiences can shape a person’s relationship with learning for years afterward. They also talk about balancing Torah, work, and family life, navigating Pesach pressure in a healthier way, and approaching struggles in kedusha with more honesty and less shame.

This is a thoughtful and practical conversation about serving Hashem with more clarity, more balance, and more simcha.

What We Discussed

• Dr. Jacobson’s path into psychology and his interest in the intersection of Torah and mental health
• The difference between stress and anxiety
• Why some pressure is necessary, but too much can become destructive
• How yeshiva culture can sometimes create unhealthy stress around learning and growth
• The long-term effect of yeshiva experiences on a person’s relationship with Torah
• What to do if learning has become tied up with guilt or pressure
• Balancing competing values like learning, marriage, parenting, and responsibility
• How to reduce stress around Pesach prep and focus more on meaning
• OCD, halachic uncertainty, and the importance of clear guidance
• Why so many men struggle silently in areas of kedusha
• What Dr. Jacobson hoped to add with his booklet Light in the Darkness

Key Takeaways

• Stress and anxiety are not exactly the same thing. Stress is often tied to present pressure, while anxiety is more future-oriented.
• Some pressure is part of growth. The goal is not zero stress, but healthy stress in the right dose.
• Yeshiva can be deeply formative, for good and for bad. If Torah became associated with guilt or pressure, that needs to be rethought.
• A working person should try to build a relationship with learning that includes pleasure, connection, and simcha — not just obligation.
• Many struggles become worse when there is too much doubt, especially for people with OCD tendencies.
• Pesach can become overwhelming when people lose sight of what is halacha and what is chumra, habit, or family expectation.
• In struggles around kedusha, shame and secrecy often make things worse. Honest, psychologically grounded guidance helps.

Notable Lines / Ideas

• “If the prime emotion that someone has with regard to their learning is a negative emotion, that has to be checked.”
• “You want there to be simcha and pleasure and joy and connection with your learning.”
• “We build our strength and resilience by encountering and learning how to handle some difficulty.”
• “The holiday of freedom can feel enslaving if we lose sight of meaning.”
  

Chapters
00:00 Intro

05:20 Stress and Anxiety, in Yeshiva and beyond
28:12 Balancing learning, marriage, parenting, and other real responsibilities
32:15 Pesach pressure: cleaning, OCD, chumros, and staying sane
38:52 Light in the Darkness: what Dr. Jacobson wanted to add to the kedusha conversation
45:48 Rapid fire

About the Guest
Dr. Dan Jacobson is a psychologist and musmach who has spent years thinking and writing about the intersection of mental health, yeshiva life, and Avodat Hashem. He is the co-author of Flipping Out and the author of Light in the Darkness, a booklet addressing struggles in kedusha with psychological depth and Torah sensitivity.