Podcast

Shtark Tank

Judaism, Religion & Spirituality

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

Episodes
148
Releases
Weekly
Typical length
40 min
On air since
2024
Latest episode
1 day ago

Episodes

148 episodes, newest first

  1. Stop the Stress ft. Simon Baum

    Show notes

    Do you ever feel anxious and exhausted?

    Simon Baum used to feel that way all the time. He returns to Shtark Tank for a follow-up on one of our most popular episodes.

    Simo is an attorney, a maggid shiur, and a Ramat Beit Shemesh dad. This time we skip the symptoms and go after the causes. Simon shares what he learned the hard way during the years he was commuting to London every week while his family was building a new life in Israel.

    We cover:

    • Why Torah and “real life” shouldn’t live in two separate buckets
    • Ve’ahavta lere’acha kamocha as three relationships (Hashem, others, yourself), and why a crack in one shows up in the other two
    • Perfectionism as a defense mechanism, and how it turns avodas Hashem into all or nothing
    • The gap between yeshiva and the real world, and what gets missed when you learn as a single guy
    • Feeling unfulfilled at work, and why the coworker who triggers you might be your personal avoda
    • Hishtadlus and bitachon: the forward looking test and the backward looking test
    • A 30 second grounding tool you can use before a stressful meeting or before you walk into your house
    • Your phone as a solution to a problem, not the problem itself
    • Why a water bottle delivered to a kid at school might have been the best thing Simon did all day

    Timestamps

    • 02:40 Simon’s story and why he’s back
    • 06:13 Stress: symptoms vs. causes
    • 15:07 Yeshiva, perfectionism, and the three relationships
    • 26:32 Building yourself vs. showing up for others
    • 31:31 When work feels meaningless
    • 37:18 Hishtadlus, bitachon, and staying calm
    • 45:17 Phones, numbing, and the ten minutes of “my time”
    • 50:46 The summary

    Mentioned: The God of My Understanding by Rabbi Shais Taub

    If this one hit home, subscribe and leave a five star review. It’s the best way to help Shtark Tank reach more professionals trying to make Torah and work fit together.

    53 min
  2. Sivan Rahav-Meir Remembers Rabbi Sacks

    Show notes

    What do you think was the most common question Rabbi Sacks got? It was not about Israel, halacha, or politics. It was “Do you remember me?”

    As we approach Rabbi Sacks’s Yartzeit, Sivan Rahav-Meir joins Shtark Tank to talk about the Rabbi Sacks she came to know. It started with a phone call during COVID, a live Zoom event with Yishai Ribo, and the realization that you are never stuck. Sivan is a seventh-generation Israeli, a longtime journalist, and a baalat teshuva. She shares what Rabbi Sacks taught her about being a shaliach, wherever you are and whatever you do.

    We talk about:

    • Why Rabbi Sacks’s real legacy might be the families who sent their kids to Jewish schools because of him
    • How being a baalat teshuva can keep Torah feeling like fire instead of habit
    • Finding balance with technology, WhatsApp, and the pull of always being “there”
    • Work, family, and why your own simcha is worth protecting
    • Staying connected across Israel’s divides without compromising halacha
    • The Jewish response to October 7th: more Shabbat, more Torah, more simcha

    Timestamps:

    • 00:00 Intro
    • 01:37 Welcome and Sivan’s background
    • 04:45 How Sivan first connected with Rabbi Sacks
    • 08:08 Torah in media, politics, and culture
    • 10:53 Torah that lights up your day
    • 15:10 Technology, balance, and “Do you remember me?”
    • 20:52 Work, family, and renewal
    • 25:33 Unity and breaking boundaries
    • 28:55 Responding to October 7th
    • 30:24 Closing

    About Sivan

    Sivan Rahav-Meir is a media personality and lecturer. She was voted by Globes newspaper as most popular female media personality in Israel and by the Jerusalem Post as one of the 50 most influential Jews in the world. She is Married to Yedidya, mother of five, lives in Jerusalem. To get her daily content search for "the daily thought".

    If you like Sivan's content, subscribe here- https://did.li/TN7CN to receive the daily thought by WhatsApp.

    For the book 'Shabat' [Hebrew] https://ybook.co.il/products/3627564

    31 min
  3. Remembering Rabbi Sacks: A CEO and a Professor on Leadership, Money, and Meaning

    Show notes

    As Rabbi Sacks’ yahrzeit approaches, we’re finally releasing the full 2024 interview recorded for our documentary series.

    Gilles Gade, founder and CEO of Cross River Bank, and Dr. Erica Brown, Vice Provost for Values and Leadership at Yeshiva University and Director of the Sacks-Herenstein Center, share how Rabbi Sacks shaped their lives and work.

    Erica was Rabbi Sacks’ student and thesis advisee in London. Gilles never met him, but calls him his rebbe after 15 years of reading Covenant and Conversation. Together they get into how his Torah plays out in a boardroom, a bank, and a home.

    In this episode:

    • Why influence outlasts power, and what Avraham teaches us about selling
    • Multipliers, diminishers, and why a bad boss is “graduate school”
    • Simcha vs. sasson, and why consumerism can’t deliver salvation
    • Shmita as an economic reset, and how Gilles applies it to consumer lending
    • Rabbi Sacks’ weekly class for philanthropists
    • Work and family: quality over quantity, and the hidden cost of mission-driven careers
    • Tzedakah as tzedek, justice rather than charity
    • Prioritizing mental health and healthcare after October 7
    • Hope vs. optimism

    Timestamps:

    • 03:08 How Gilles and Erica found Rabbi Sacks
    • 10:01 Power vs. influence
    • 19:31 Consumerism, joy, and the American dream
    • 22:41 Banking, credit, and shmita
    • 31:02 Rabbi Sacks and the business world
    • 33:52 Balancing work and family
    • 44:08 Tzedakah as justice
    • 52:03 Prioritizing after October 7
    • 55:44 Closing thoughts on hope

    Guests:
    Gilles Gade is the founder and CEO of Cross River Bank.
    Dr. Erica Brown is Vice Provost for Values and Leadership at Yeshiva University and Director of the Rabbi Lord Jonathan Sacks-Herenstein Center.

    Make sure to check out our newsletter at ShtarkTank.org

    59 min
  4. Noach's Biggest Test

    Show notes

    What's harder, being the tzaddik of an entire generation, or being a good father?

    A short idea on this week's parsha

    Make sure to subscribe to our newsletter at Shtarktank.org

    7 min
  5. October 7th Reflection (and a Personal Update)

    Show notes

    A Rabbi in rehab after being wounded on October 7th shared a Dvar Torah with me on why the angel quit fighting Yaakov Avinu. I also shared some personal news that means a lighter schedule for the show.

    5 min
  6. Get Ready For Sukkot

    Show notes

    Let's get ready for sukkot, with three Divrei Torah from Bnei Torah in the workforce.

    We cover daled minim, sitting in the sukka, shemini atzeret and more!

    Our guests: Rav Zecharia Rosenthal, Betzalel Cohn, Ephraim Goldstein

    Make sure to subscribe to our newsletter, where I share unfiltered thoughts on Torah, Work, Family and more. ShtarkTank.org

    For more of Betzalel's Corporate Divrei Torah, click here

    Key Topics

    • The connection between Sukkah and mezuzah as a reminder of impermanence
    • The concept of Diras Keva and its relation to mezuzah and Sukkah
    • The idea of transition times in life, such as after Yom Kippur and Shemini Yatzeret
    • The role of humility and acknowledgment of limitations in fulfilling mitzvot
    • The importance of mindfulness and intentionality in everyday transitions
    • The impact of Torah and mitzvot on personal and communal security
    • The analogy of the Etrog and the concept of Hadar in mitzvah performance
    • The significance of Shemini Yatzeret as a day to pause and reflect
    • The parallels between military transition rituals and spiritual transition in life

    Chapters

    00:00 Intro

    00:53 Rabbi Zechariah Rosenthal - Temporary or Permanent?

    12:58 Betzalel Cohen - Beautiful or Messy?

    25:01 Ephraim Goldstein - One More Day

    35 min
  7. Yizkor 10.7 Yosef Guedalia ft. David Guedalia

    Show notes

    Yosef Guedalia escaped his burning jeep, and ran straight at the terrorists position.

    For the third year running, we mark the Aseret Yemei Teshuva with Yizkor 10.7, honoring the heroes of October 7th.

    This years episode is about Yosef Guedalia Hy"d, who fell defending Kfar Azza. We are joined by David Guedalia, Yosef's father.

    We spoke about:

    - Yosef's packed Friday routine, the quiet happiness, the instinct to care for other.

    - The heroic battle in Kfar Azza: the RPG that hit Yosef's jeep, the rescues under fire, and the charge through the gate that broke the terrorists' momentum and stopped the kidnappings.

    - Torah perspectives on grief, loss, and fatherhood. We examine the Akeida, the famous story of the 4 who entered the Pardes, and a drasha that went very wrong.

    To support the Mechina in Kfar Azza click here

    For videos about Yosef click here

    Chapters

    00:00 — Intro

    06:09 — Yosef’s Life: Joy, Discipline, and Service

    34:23 — October 7: The Battle at Kfar Aza

    59:28 — Grief, Trauma, and Finding Meaning

    78:47 — Peoplehood, Connection, and Carrying Yosef’s Legacy Forward

    1 hr 49 min
  8. Yamim Noraim Mega-Episode

    Show notes

    For Rosh Hashana and Yom Kippur, we wanted to do something special. Eight voices from around the world, eight perspectives on the Yamim Noraim. Here's the lineup:

    • Ezra Meyer — car salesman and global chazzan, on how he prepares to lead tefilla on the Yamim Noraim
    • Dr. Herman Weiss — OBGYN and baal tokeah, on his path to becoming a baal tokeah and one of his most memorable mistakes
    • Rabbi Yossi Katz — Rav in Linden, NJ and partner in a recruiting firm, on Akeidat Yitzchak and how Avraham Avinu reframes how we approach being Bnei Torah in the workforce
    • Rav Tzvi Sinensky — director of the Lamm Legacy, sharing a Rosh Hashana drasha Rav Lamm gave his kehilla on integrating business success with religious success
    • Rav David Aron — co-Rosh Yeshiva of Orayta and founder of Isralight, on the proper attitude toward Yom HaDin
    • Rav Mitch Berger — computer programmer and author on Rav Shimon Shkop's hashkafa in his hakdama to Shaarei Yosher
    • Yitzi Lowe — combat soldier in the IDF, on Yodei Terua
    • Bonus: Yaakov Wolff on Headlines — audio from an interview on the Headlines podcast, hosted by Rav Ari Wasserman, on the phrase "Shivti B'veis Hashem"

    A lot of work went into this one. Special thanks to Shlomo Price for extra editing help.

    If you haven't already, subscribe, and if you're so inclined, leave a 5-star review.

    It helps the show reach more people.

    Resources Mentioned:

    • Bshir Yaron, website for Chazzanim
    • The Revelation of Man, Drasha by Rav Norman Lamm
    • 'Widen Your Tent' by Rav Micha Berger

    Chapter list:

    • 0:00 — Intro
    • 2:26 — Ezra Meyer: Preparing to Lead the High Holiday Prayers
    • 21:49 — Dr. Herman Weiss: The Responsibility of Blowing the Shofar
    • 35:21 — Rabbi Yossi Katz: Avraham Avinu and Finding Meaning in the Journey
    • 45:00 — Rabbi Tzvi Sinensky: Rabbi Norman Lamm on Potential and Purpose
    • 58:01 — Rabbi David Aaron: Rethinking Judgment on Rosh Hashanah
    • 1:09:57 — Rav Micha Berger: Rav Shimon Shkop’s Vision of Responsibility
    • 1:29:15 — Yitzy Loew: The Shofar’s Call to Enlist
    • 1:45:29 — Headlines Appearance: Building a Torah-Centered Life in the Workforce

    1 hr 55 min
  9. How a Judge Experiences Yom HaDin ft. Jeremy Rovinsky

    Show notes

    Jeremy Rovinsky is a full time United States immigration judge, an associate justice for multiple Native American courts of appeals, a law professor at Crest Point University, and Dean of Teachers for the Tikvah Foundation's Millstone Scholars Program. He's also a baal teshuva who took his judicial oath on the Chovos HaLevavos.

    Jeremy spends his days behind the bench. This week he brings that lens to the Yamim Noraim: what din really means, why teshuva is recalibration and not erasure, and what it's like to approach Hakadosh Baruch Hu as the ultimate judge when you know exactly what it feels like to sit in the chair.

    In this episode:

    • Going from philosophy major to talmid of Rav Gershenfeld at Machon Shlomo
    • Why his Rebbe told him to stay in law, not switch to kiruv
    • The Zohar's read on Lech Lecha: bring your past with you, don't leave it behind
    • Why the Sanhedrin required judges to have children (and what that teaches about rachmanus)
    • Justice as love, not just din, and why that changed how he saw his own docket
    • What Jeremy says to the God of Israel these days, now that he's not the prosecutor anymore

    Subscribe, leave a five star review, and check out the newsletter at shtarktank.org for more unfiltered thoughts on Torah, family, and life.

    42 min
  10. "The Doctors Told Us to Say Goodbye" ft. Rabbi Jason Weiner

    Show notes

    Emotional support at the end of life. Thorny halachic questions about scientific medical breakthoughs. AI and the end of work.

    These are all part of the Rabbi Jason Weiner's daily routine.

    Rabbi Weiner is the senior rabbi and executive director of spiritual care at Cedars Sinai in Los Angeles. In this episode we cover:

    • What a healthcare chaplain actually does, and how Rabbi Weiner fell into the role with almost no training
    • The hardest moments of sitting with grieving families, including an uplifting story that took nearly 20 years to find its ending
    • How Torah sources think about medical breakthroughs like CRISPR and GLP-1 drugs
    • His essay on AI and the end of work: if a machine takes your job, does it take your identity too?

    To read the full Tradition Online essay about AI and the end of work, click here

    Find more from Rabbi Weiner at rabbiweiner.com, on YUTorah, on LinkedIn, or on Instagram at @rabbi_JW.

    Sign up for our newsletter to recieve unfiltered takes on work, Torah, family and more. Go to ShtarkTank.org and subscribe today.

    44 min
  11. Rav Hershel Schachter: Finding Meaning as a Ben Torah in the Workforce (Shiur plus Q&A)

    Show notes

    Subscribe to our newsletter at Shtarktank.org

    Rav Hershel Schachter addresses one of the most persistent tensions in the frum professional world: does the ben Torah at work matter as much as the one in the beis medrash?

    Recorded live in partnership with the OU Israel Business Professionals Network, this episode includes the full shiur plus a Q&A.

    What's covered:

    • Why Klal Yisrael needs doctors, lawyers, engineers, and businessmen just as much as it needs roshei yeshiva, and why the "learning is more important" mindset is a distortion, not a Torah value
    • The little-known letter from Rav Elya Meir Bloch on why the religious world can't afford to run from Zionism, Tanach, or Ivrit
    • A Q&A covering how much work is enough, whether a rabbi should be wealthy, balancing communal obligations against raising your own children, and a practical seder for using limited learning time (starting with Kitzur Shulchan Aruch)
    • Why Rav Schachter has spent 30 years teaching high schoolers at NCSY Kollel, and what he sees in that generation

    40 min
  12. Should You Start Your Own Company? ft. Alec Kremins (Founder, Baal Teshuva, Content Expert)

    Show notes

    One year ago, Alec Kremins got fired. Same week he found out his wife was pregnant with their first child. He had a choice: go find another stable job, or bet on himself.

    He went all in.

    Alec built his career at Ramp (now valued near $40B) before making Aliyah and eventually going out on his own. In this episode we get into why he tells most people not to start a company, even though it was the right call for him.

    We cover:

    • The day he got let go, and the decision that followed
    • Why he thinks life is about meaning, not comfort, and the Lubavitcher Rebbe story about the "contract" nobody signed promising an easy life
    • The Histadlus/Bitachon dance and why it gets a lot harder when you're working for yourself
    • Whether your work should be part of your identity, or just what funds it
    • A surprising parallel between starting a company and childbirth (his words, not ours)
    • Why he actively discourages most people from starting their own thing
    • Building a personal brand without losing your Shabbos, your learning, or your sanity to the algorithm
    • Where AI actually fits in content creation, and where it doesn't touch the core at all

    Alec Kremins is the founder of RallyUp. You can find him on LinkedIn.

    33 min
  13. Yaakov Wolff Answers Your Questions with Rav Ari Koretzky

    Show notes

    Har HaBayit. Torah Im Derech Eretz. Searching for Meaning.

    It's the summer mailbag episode! Yaakov opens up the inbox and brings on Rav Ari Koretzky (director of Meor Maryland, host of the Iyun podcast) to work through listener feedback together.

    In this episode:

    • Why Shtark Tank does pre-chag episodes, and whether they're on brand or just a scheduling excuse
    • Is there such a thing as a distinct "baalabatish hashkafa" for guys balancing Torah and a career
    • A listener's story of how the podcast changed how he networks and built real friendships through cold outreach to guests
    • Rav Ari's day job in kiruv, and why baalei teshuva may find an unexpected home in Shtark Tank's world
    • Pushback on the Har HaBayis episode, including the halachic and hashkafic case against ascending, and whether the debate got a fair hearing
    • How to handle controversial topics without becoming a clickbait machine, and the cost of staying in your lane
    • Why the Rav Rafi Dembovsky episode on Torah Im Derech Eretz struck such a nerve
    • The "grass is greener" pull toward nonprofit work, and why it's not the meaning shortcut people think it is
    • What 130+ episodes have taught Yaakov about mindset, and what's actually holding Shtark Tank back from growing bigger

    1 hr 1 min
  14. Living Up To Our Values ft. Rav Uri Lorkis (Torat JLIC Crossover)

    Show notes

    What happens after the fire of yeshiva goes out?

    This week I'm sharing an episode from Torat JLIC, a podcast I love, one that takes the complexity of modern life seriously instead of talking around it.

    The guest for this episode is Rav Uri Lorkis, who just wrapped a few years as JLIC rabbi in Michigan and now works as a startup coach. We dig into the real transition every yeshiva guy faces: how do you carry that intensity into the next stage of life, when the schedule, the chavrusas, and the structure are gone?

    Beyond the practical adjustments is a deeper crisis: Is it possible to live up to our values? Or will the daily grind dictate our agenda?

    Rav Uri brings some sharp, honest insight.

    Make sure to check out the Torat JLIC feed for more great content!

    31 min
  15. Tisha B'Av Prep ft. Rav Moshe Taragin: Mourning in Times of Geulah, Achdut and Har Habayit

    Show notes

    How do you mourn a Beis Hamikdash you never knew, in a generation that's watched Klal Yisrael return to Eretz Yisrael and rebuild a country? Rav Moshe Taragin returns to Shtark Tank to help us hold two truths at once: we are living through open miracles, and we are still so far from the finish line.

    Rav Taragin unpacks why every question in Jewish life now splits into "before October 7th" and "after," why Tisha B'Av doesn't require manufactured grief but honest yearning, and how looking at Chazal's account of the Churban Bayis Sheni (zealotry, internal division, over-reliance on foreign powers) maps uncomfortably well onto Israeli society today.

    He also addresses the tension around visiting Har Habayit as a means to an end versus an end in itself, and offers a clear-eyed, non-preachy take on Aliyah, achdut, and what it means to stay grounded when the news cycle wants you anxious and reactive.

    In this episode:

    • Why October 7th changed the answer to nearly every question in Jewish life
    • The difference between authentic mourning (aveilus balev) and performing grief on cue
    • The machlokes over changing Nusach HaTefillah to reflect our current reality
    • What the internal strife of the Second Beis Hamikdash teaches us about achdut today
    • The danger of turning Har Habayit visits into a photo op or political statement
    • Why Aliyah advocacy can tip into preachiness, and how to hold the ideal without judging the complexity of other people's lives
    • Practical advice for gaining perspective when you're drowning in headlines

    Rav Taragin's new sefer, Reclaiming Redemption, HaGeula Volume 2: Faith, Identity, Peoplehood, and the Storms of War, is out now.

    Check out

    https://www.mtaraginbooks.com/

    You can also join Rav Taragin's Whatsapp Chizzuk Chat:

    https://chat.whatsapp.com/HAER24G31VpJZW5zEXROYH for daily chizuk

    43 min
  16. Holiness in the Heat ft. Dr. Dan Jacobson

    Show notes

    To recieve a free copy of Light in the Darkness, about Shemirat HaEinayim in today's world, email dan.jacobson.psyd@gmail.comSummer turns up the heat on shmiras einayim, and this episode isn't going to fix that. It's an honest conversation about the struggle, with returning guest Dr. Dan Jacobson offering real perspective instead of a quick fix.

    We get into:

    • Why the trigger itself was never the real issue, and what actually determines what happens next
    • How mindfulness (yes, the same tools behind DBT and ACT) offers a different way to hold a hard moment, without pretending it isn't hard
    • Why chasing a clean scorecard of "success" or "failure" in this area does more harm than good
    • A sharp Taz on hespedim that reframes the whole question: who you are is what you value, not your track record
    • Whether tznius really is "the battle of our generation," and what it means to sit with that honestly
    • Practical thoughts on family vacations and beach trips, without easy answers

    Dan mentions Palouse Mindfulness, a free 8-part course by a student of Jon Kabat-Zinn, for anyone who wants to go deeper on their own.

    If this conversation was honest in a way you needed, leave a 5-star review. It helps more people find it.

    34 min
  17. Should You Be Going to Har HaBayit? ft. Rav Yehuda Levi

    Show notes

    The three weeks are here.

    The time when we refocus on the fact that our lives are incomplete.

    There is a gaping hole in our ruchniyus, located at the holiest spot in the world. Har HaBayit.

    Some of us just think about the problem.

    Others are actually doing something about it.

    Rav Yehuda Levy is the latter.

    He has spent countless hours learning the sugya, written articles, taught classes, and spoken to gedolei yisrael.

    He also goes up regularly, was involved in starting Yeshivas Har HaBayis, and has played an active role in expanding tefillah rights at our holiest site.

    All of this, in addition to his professional life as a video production manager and a United Hatzalah volunteer.

    In this episode, we discuss:

    • A quick overview of the sugya (it's simpler than you think)
    • How an iPhone 11 with portrait mode led to easing restrictions for Jews on Har HaBayis
    • Why the gedolim were opposed
    • The pushback Rav Yehuda received (called an apikores and more)
    • The right way to bring the geulah (surprising psak halacha)

    The goal of this episode is not to change your mind. But this is a sugya that deserves to be taken seriously.

    To learn more from Rav Yehuda Levi, check out https://beishashem.org/

    43 min
  18. Live @ YU Israel | Reu Berman, Zevi Reinitz, Moshe Rapps and Shaun Regenbaum

    Show notes

    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.

    55 min
  19. Bonus: Live Career Coaching — Kollel to Career with Yaakov and Teddy Berman

    Show notes

    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

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

    Show notes

    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.

    42 min