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.

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

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 DiscussedDr. Jacobson’s path into psychology and his interest in the intersection of Torah and mental healthThe difference between stress and anxietyWhy some pressure is necessary, but too much can become destructiveHow yeshiva culture can sometimes create unhealthy stress around learning and growthThe long-term effect of yeshiva experiences on a person’s relationship with TorahWhat to do if learning has become tied up with guilt or pressureBalancing competing values like learning, marriage, parenting, and responsibilityHow to reduce stress around Pesach prep and focus more on meaningOCD, halachic uncertainty, and the importance of clear guidanceWhy so many men struggle silently in areas of kedushaWhat Dr. Jacobson hoped to add with his booklet Light in the Darkness Key TakeawaysStress 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.” Chapters00:00 Intro 05:20 Stress and Anxiety, in Yeshiva and beyond28:12 Balancing learning, marriage, parenting, and other real responsibilities32:15 Pesach pressure: cleaning, OCD, chumros, and staying sane38:52 Light in the Darkness: what Dr. Jacobson wanted to add to the kedusha conversation45:48 Rapid fire About the GuestDr. 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.

We recorded a regular Shtark Tank conversation with Tuvia Eisenman—about sales, chessed, and life in Israel. Then the war broke out. Tuvia was called back to reserve duty, and he joins us now from his IDF base with an emergency update. He walks us through the past few days, shares what it’s like on the ground in the Jordan Valley, and offers powerful reflections on what soldiers and their families are facing right now. After the update, we return to the original conversation, recorded just days earlier. Tuvia shares how a yeshivish kid from Passaic ended up serving in the IDF, building a sales career in Israel, and using those skills to raise millions for nonprofits around the world. We talk about the art of listening—how it drives both sales and parenting—and how he balances intense frontline experiences with raising a family and living a life of purpose. We also dive into the world of nonprofit marketing and fundraising. Tuvia offers a frank take on why most campaigns fall flat, how organizations can do better, and why peer-to-peer giving—though messy and personal—is actually one of the frum community’s greatest strengths.

“Life is like a train. You might get derailed, but you know where the train needs to go. You get back on the track.” Rav Reuven Berman didn’t plan to leave chinuch. He made Aliyah with a dream job teaching Torah in Yerushalayim—but it quickly became clear that the math didn’t work. With five kids and growing responsibilities, he transitioned into the business world while trying to hold on to his identity as a ben Torah. In this honest and moving conversation, we cover:✅ Being grouned in business while also connecting to yeshiva✅ What he learned from a personal tragedy✅ Why teaching—even part-time—can protect your neshama✅ The power of a strong minyan✅ How to stop dreaming of the “perfect community” and live in the one you’ve got✅ And why every year in yeshiva still counts—even if you go to work later Reuven shares what helped him stay grounded through transitions, success, and grief—and why he still dreams of being back in the beit midrash full time. — Check out ShtarkTank.org for exclusice written content!

What happens when a full-time chiropractor with a busy practice, a big heart, and zero spare time decides to launch a global tzedakah revolution—one dollar at a time? This week on Shtark Tank, we sit down with Dr. Jonathan Donath, founder of Daily Giving, a platform that’s quietly transformed the world of tzedakah. What started as a flash of inspiration in a shul lobby has turned into a global force for chesed, distributing over $24 million to 100+ vetted nonprofits (including ADI Negev) and empowering over 21,000 daily givers around the world. But the road wasn’t smooth. In this raw and inspiring conversation, Dr. Donath shares: 🧠 His powerful “epiphany moment” that sparked Daily Giving 💵 The emotional struggle of transitioning from volunteer founder to salaried CEO 🧘 How self-compassion and meditation saved him from burnout 📉 The surprising downside of professional success—and why he gave up Tuesdays 📚 The books, seforim, and mentors that changed how he thinks about purpose🛠️ His evolving views on balance, ambition, fatherhood, and the cost of impact Resources Mentioned: 💸 Become a daily giver: DailyGiving.org📘 Books: It's All the Same to Me and The Three Conditions by Moshe Gersht📘 Radical Compassion by Tara Brach 🎥 Rabbi Alon Anava – “My Life After Death Experience”: Watch on YouTube📗 Living Emunah series by Rabbi David Ashear📙 Living Legend – Biography of Rav David Grossman For More Shtark Tank go to ShtarkTank.org

This week on Shtark Tank, we welcome Rabbi Shalom Rosner—Rav of Kehillat Nofei HaShemesh, Rosh Beit Midrash at Machon Lev, beloved Daf Yomi maggid shiur, and my uncle—for a deeply personal conversation about his father, Dr. Fred Rosner z”l. Check out the newly released Shalom Rav Birkon (bentcher) here. Born in Berlin in 1935 and rescued via Kindertransport, Dr. Rosner began life with no formal Jewish education. But he went on to become not only a world-renowned physician and medical ethicist, but a serious talmid chacham, translator, and teacher of Torah and halachic medicine. In this episode, we explore: The incredible story of Dr. Rosner’s late start in Torah learning—and how one summer of Mishnah changed everything His unwavering consistency and sense of mission, both in the hospital and the beit midrash The evolution of Jewish medical ethics, and how Dr. Rosner worked alongside gedolim like Rav Moshe Feinstein zt”l Balancing public influence with personal humility The quiet legacy of a man who never wasted a moment, right up to the final day Along the way, we also discuss family, Shabbos zmiros, Rambam, professional responsibility, and what it really looks like to synthesize Torah and derech eretz—without compromising either. Check out ShtarkTank.org for more!