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Imposter Syndrome: The Struggle is real... but am I?

Dave is off at Camp Kaylie helping with their intern program, which means Jon and Asher are flying solo tonight, and somehow still managing to fill nearly an hour with conversation, tangents, and a very important child in underwear watching fireworks from a car roof.

But before all that, Jon and Asher kick things off with a proper What Are We Thinking About segment. Asher just visited Camp Kaylie himself and cannot say enough about the staff, the Rabbeim, and the magical island they have built there. Shout out to Mommy Rachel, the first husband of Camp Kaylie, and Izzy, who not only cleaned Asher's car before he left for the summer but refused money for it and waited to open his brand new phone until after camp started. Meanwhile Jon spoke to a group of OU AI interns today, felt like the smartest person in the room for about four minutes, and then realized he was the oldest person in the room by approximately one generation.

Which brings us to the topic of the week: Imposter Syndrome. The guys dig into what it actually feels like to walk into a room and wonder whether you belong there, at work, at a Shabbos table, in a job interview, in your own career. Jon talks about the period in his professional life when he felt stuck at the bottom rung, and how learning to podcast, of all things, unlocked something in him that changed his trajectory. Asher opens up about taking on a new leadership role without his longtime mentor as a safety net, and what it felt like to suddenly be the person everyone else was looking to for answers.

There is also a real conversation about the difference between imposter syndrome and humility, why saying "I don't know" is actually a sign of confidence, the Dunning-Kruger curve, setting professional boundaries during long weekends, and the difference between being a team player and being a doormat.

Plus: the word "correct" as a conversational power grab, how long is too long for a WhatsApp voice note, the era of asking permission before calling someone, Camp Kaylie visiting day survival, the chain of yelling from How I Met Your Mother, root beer floats as a spiritual experience, the grand finale that nobody can identify, and one of Asher's children watching July 4th fireworks from the roof of a car in their underwear.

Big announcement: The Carpool Guys WhatsApp listener community is launching. Email carpoolguyspod@gmail.com to get in.

Also coming soon: Official Carpool Guys car magnets. Yes, really.

Question of the Week from Jon: What is your favorite part of the Fourth of July, and what is your least favorite?

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⏱️ Chapters with Timestamps

0:59 — What Are We Thinking About: Asher Visits Camp Kaylie

1:17 — Happy Birthday Izzy — Our Number One Listener

4:57 — The Word "Correct" as a Conversational Power Grab

8:26 — How Long Is Too Long for a WhatsApp Voice Note?

16:30 — Announcement: The Carpool Guys WhatsApp Listener Group Is Launching

18:39 — Jon Speaks to the OU AI Intern Program Today

22:19 — Topic of the Week: Imposter Syndrome, the Struggle Is Real

26:01 — Why Saying "I Don't Know" Is Actually a Sign of Confidence

28:43 — When Early Career Overconfidence Gets in the Way of Actually Learning

29:38 — Asher's Mentor Susan Heckler: It's the Conversation After the Conversation

31:00 — How Learning to Podcast Unlocked Something in Jon Professionally

38:00 — The Chain of Yelling From How I Met Your Mother and What It Has to Do With Work Culture

40:13 — You Never Know What's Going On in Someone's Life, Even as a Therapist

43:08 — Question of the Week Is Sponsored by Asher in Honor of Dave

50:30 — WhatsApp Group Launch: How to Join

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Asher and fam are on the way to visiting day at Camp Kaylie… and perhaps a rendezvous with Dave from Flatbush? What are your favorite visiting day customs? What about the mishaps? Send us an email with your visiting day stories and we may share them on the next episode of The Carpool Guys!

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From Comedy to Courage: Eli Lebowicz Joins the Carpool

If you have ever wondered what it looks like when one of the funniest people in the Jewish world sits down with three dads who have absolutely no idea how to use Google Chrome, wonder no more.

Comedian Eli Lebowicz joins Jon, Asher, and Dave for what is without question the funniest episode The Carpool Guys have ever recorded. Eli is the mind behind J Sketch, the Jewish comedy account that has produced some of the most shared and quoted content in the Orthodox world — Jewish Jeopardy, the Sium sketch, the supplies to Israel video, and dozens more. He is also one of the sharpest voices in Jewish comedy working today, using humor not just to get laughs but to make real points about Jewish identity, antisemitism, and what it means to be proud of who you are.

But this episode is not just a comedy interview. Eli talks about how J Sketch got started, how he comes up with his Torah-based material, why he went to Israel to perform during the Iran war, and what it actually looks like to fight antisemitism with humor in 2025. There is a genuine conversation about Jewish identity and what it means to be proud of who you are — wrapped inside one of the most chaotic, hilarious, and completely unscripted hours this show has ever produced.

Also in this episode: Dave catches a tiger shark and attends a Trevor Bauer game in the same week, the guys do a Shabbos lunch together for the first time and Jon melts the ices, missing giraffes in Virginia, Asher's mother prefers the recorded version of him, the origin of the Sota joke, a Paroh bathroom theory that may be too long but is definitely funny, Dave's colonoscopy note, the Twizzler straw debate, and the most important question of the episode — how many holes does a straw have?

Oh, and Eli's Netflix special will be called "Remind Me After Shabbos." Mark your calendars.

Question of the Week from Dave: What is your road trip go-to snack?

��️ Find Eli Lebowicz online:
🌐 elicomedy.com
📱 Instagram: @elicomedyagram
🐦 Twitter/X: @EliLebowicz

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⏱️ Chapters with Timestamps

0:27 — Welcome + What Are We Thinking About This Week

6:51 — Eli Lebowicz Joins the Carpool!

13:37 — The Secret Origin of J Sketch

25:06 — The Evolution of Jewish Comedy: It's Not Just Stand-Up Anymore

36:47 — The Origin of the Sota Joke: Mortal Kombat Meets the Parsha

50:45 — Eli During the War: Comedy as a Frontline Tool

57:35 — Upcoming Shows: Chai Lifeline Alumni, Cheese Store Singles Event, Catskills Summer

57:53 — Five Rapid Fire Questions

1:04:24 — Question of the Week: What Is Your Road Trip Go-To Snack?

1:11:22 — Thank You Eli, Closing Shoutouts, and How to Find Eli Online

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Emergency Episode: The New York Knicks Are World Champions

We interrupt our regularly scheduled programming because the New York Knicks are the 2026 NBA World Champions, and the Carpool Guys could not let that go unmarked.

Jon, Asher, and Dave jump on for an emergency episode the morning after, and the energy is exactly what you'd expect. Asher has been a die-hard Knicks fan his entire life and is fully in his feelings. Dave, a self-described "Knicks fan since last week," brings the perspective of a Nets-Knicks-Nets-Nets fan who got swept up in the run despite himself. And Jon, a lifelong Timberwolves fan with zero skin in the game, brings the outsider's view of a city losing its mind in the best possible way.

The guys talk about the crossing guard who stopped them on the way to shul to share the news, the shul security guards who somehow always know the score before anyone else, the WhatsApp groups that have not stopped buzzing for a week, and the wild story of someone who rented a hotel in Seattle just in case Game 7 fell on Shabbos.

There's a real conversation about the Jalen Brunson story, why an underdog who was written off by everyone resonates so deeply, and what it means to say "we" when your team wins. Plus: a debate about New York sports rivalries, Dave's complicated Knicks-Nets history, a tribute to the Dallas Mavericks for the Luka and Brunson draft disaster, and a very memorable story involving Rebbe Hecht, a basketball hoop, and a coach bus.

Question of the Week from Asher: What are the top three sports moments you've ever watched live or experienced in real time?

Mazel Tov to Knicks Nation. And to Asher, Steven Mermelstein, and Meir Simcha specifically. Enjoy this one.

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⏱️ Chapters with Timestamps

0:25 — Welcome to an Emergency Episode: The Knicks Are Champions

1:22 — Asher Has Been a Knicks Fan "Since Last Week"

11:19 — Are the Knicks New York's Most Universal Team?

12:06 — The Brunson Underdog Story and Why It Resonates

13:43 — Izzy Calls It at Halftime: The Comeback Theory

15:45 — Why Years of Losing Make This Run Mean More

21:53 — Ranking New York Sports Rivalries

29:48 — Question of the Week: Top Three Sports Moments of Your Life

37:43 — "We Did It" vs. "They Did It": The Great Sports Fan Debate

38:36 — Closing: The Brunson Pose, a Logo Idea, and Mazel Tov to Knicks Nation

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Some people spend their whole lives searching for where they came from. Sarit Saffer-Allal spent hers perfectly content not knowing — until one birthday changed everything.

Born in South Africa and adopted at just two weeks old into a warm, observant Jewish family, Sarit always knew she was adopted. She had a loving upbringing, a strong Jewish identity, and no particular urgency to open the box. Then she turned 35, looked at her two kids, her only known blood relatives, and quietly asked herself: who am I really?

What followed is one of the most extraordinary stories the Carpool Guys have ever heard. Sarit opened her adoption file, discovered her birth name was Gina Thompson, learned her birth mother had hidden the pregnancy entirely, and found out she had a brother she never knew about. Then, through a single Facebook message, she discovered something nobody saw coming. A half-sister. Adopted in South Africa. Also into a Jewish family. Also in Toronto. Living less than two kilometers away, or as the guys needed it translated, up the street.

In this conversation, Sarit opens up about what it felt like to read someone else's biography that turned out to be her own. She talks about confronting a birth mother who denied her existence, flying to New Zealand to meet a birth father who welcomed her with open arms, and navigating the beautiful chaos of suddenly having an entirely new family, while making sure her adoptive family, who chose her and raised her, knew they were never being replaced.

And underneath all of it runs a quietly profound thread: what does it mean to be Jewish when you were chosen to be? When your birth mother was not Jewish, your adoptive parents converted you, and your half-sister ended up on the same street living the same life? For Sarit, this journey answered that question once and for all. She did not stumble into Judaism. She was placed there. And she owns it completely.

Also in this episode: Dave nearly gets arrested at the Israel on Fifth parade while photobombing a news crew, Jon's Israel parade video attracts 9,000 views and 91 comments of varying hostility, a mouse gives a peace sign, Asher shows up late, Jessica Tish is everyone's hero, Dave dreams of Saratoga, Jon loves a good garage sale, and Asher got stung by a thousand bees at the bay.

Question of the Week from Dave Tannenbaum: If you could get lost for a day and go anywhere, 24 hours, travel time included, where would you go?

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⏱️ Chapters with Timestamps

1:02 — Dave Nearly Gets Arrested at the Israel on Fifth Parade

8:15 — Jon's Israel Parade Video: 9,000 Views and 91 Comments of Chaos

17:30 — The Mayor Who Didn't Show Up and Jessica Tish Is Our Hero

20:15 — Shout Outs: Happy Anniversary Avi + In Memory of Daniel Chernikov

23:00 — Introducing Sarit Saffer-Allal: NCSY Colleague and an Incredible Story

25:10 — Sarit's Background: Born in South Africa, Raised in Israel, Living in Toronto

28:00 — The 35th Birthday That Changed Everything

30:15 — Opening the Adoption File: Reading Someone Else's Biography

40:15 — Did Sarit Ever Get the "Choose Your Judaism" Moment? + She Chooses Live on Air

44:45 — "We Found a Sister and She Lives in Canada" — The Message That Changed Everything

57:00 — The Birth Father in New Zealand: A Total Surprise Who Welcomed Her Completely

1:02:30 — What This Journey Did to Sarit's Jewish Identity

1:05:00 — October 7th and the Moment She Knew She Was Chosen to Be Jewish

1:07:00 — Expanding Your Heart: Adding Family Without Replacing Family

1:13:00 — Dave's Question of the Week: Get Lost for a Day — Where Do You Go?

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Why Are We Always So Tired? The Exhausted Jewish Life Edition

Somebody had to say it. We are exhausted. All the time. Every single day. And not in a "ran a marathon" kind of way... in a "stared at a dinner menu for four minutes and still couldn't decide" kind of way.

Fresh off their most successful episode ever featuring Allison Blass, Jon, Asher, and Dave are back together- and Asher is fresh off a trip to Israel for nephew Meir Simcha's bar mitzvah. But jet lag quickly gives way to a much bigger conversation: why does it feel like everyone around us is running on empty?

The guys dig into the real reasons modern exhaustion hits differently — the constant connectivity, the WhatsApp messages that start before 7am, the total disappearance of boredom, the dual curriculum school day, the shul commitments, the community obligations, and the creeping anxiety of a world that never really turns off. Plus Dave's infamous half-a-block bike ride that ended with him passed out in a Brooklyn garbage room. And the debut of a brand new segment: the guys go around the room and share what is on their minds this week, from aliens and AI to the Hanta virus and the eternal question of which is scarier: Independence Day or Terminator.

Also: snoring during bar mitzvah speeches, AIM away messages, The Brick app (purchased, never used), Trump's Shabbos proclamation, Dave's "David Days," essential worker pride, and the most important question in Jewish history — which Parsha would you most want to live through?

Question of the Week from Anonymous in Commack: If you could live through any Parsha, which would it be?

We want to hear from you — are you exhausted? What is draining you most right now, and how do you combat it? Email us at carpoolguyspod@gmail.com or drop a comment on YouTube.

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⏱️ Chapters with Timestamps

0:00 — Cold Open: Snoring at a Bar Mitzvah. Avi Was Not Happy.

0:27 — Welcome Back + Shoutout to Allison Blass

2:00 — Welcome to New Listeners + Now on Amazon Podcasts and Podbean

3:47 — New Segment Debut: Around the Room — Naming Rights Contest Announced

17:10 — Today's Topic: Why Are We Always So Tired?

20:26 — The Phone Problem: There Is No Off Button Anymore

23:48 — Is the Jewish Lifestyle More Exhausting Than Everyone Else's?

26:31 — The Anxiety Tax: Always Waiting for the Next Shoe to Drop

27:47 — No Escape From Work: WhatsApp Does Not Have an Away Message

31:22 — Dave Falls Asleep During Bar Mitzvah Speeches — Full Story

33:37 — Asher Falls Asleep on Someone's Couch — Also a Full Story

43:11 — Dave Days: Twice a Year, No Explanation Needed

43:41 — Question of the Week: Which Parsha Would You Want to Live Through?

51:38 — Closing: Comment on YouTube, Email Us Your Exhaustion Stories

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When Life Takes an Unexpected Turn: Allison Blass on Parenting a Child with Cancer, Faith, and Finding the Funny

Some episodes stop you in your tracks. This is one of them.

Allison Blass — longtime listener, friend of the show, and one of the funniest people to ever sit across from the Carpool Guys — joins Jon, Asher, and Dave to share the story of her daughter Perry's cancer diagnosis, treatment, and remarkable recovery. What begins as a frightening story of a six centimeter mass discovered on a Friday afternoon twenty minutes before Shabbos becomes something else entirely: a masterclass in parenting under pressure, faith in the hardest moments, and the kind of stubbornness that saves lives.

Peri, Allison's oldest child, was diagnosed with one of the rarest malignant tumors on record — one of only twenty cases ever documented. She went through multiple rounds of chemotherapy, a week in the ICU with fungal pneumonia, hair loss, wild food cravings, and a surgery she woke up from demanding a double burger from Smash House. She was walking within hours, home by Shabbos, and is now a completely healthy teenager heading to high school next year.

But this episode is about so much more than the medical story. Allison opens up about what it means to keep your other children grounded when one child needs everything. She talks about the friends who showed up without being asked and the ones who said "let me know if you need anything" — and why that phrase, though well intentioned, puts the burden on exactly the wrong person. She shares how her family turned every moment of the process — the hair donation, the chemo mug, the smash room — into a kiddush Hashem. And she delivers one of the most important lessons this show has ever aired: when someone you love is going through something devastating, it is not their job to comfort you.

Also: gherkins, sushi rolls, an accidental antipsychotic mix-up, a son who slept for fifteen hours, Megan Trainor's Walk of Shame playing in an operating room, Disney turkey legs, and the best shirt ever made.

Allison, thank you for your vulnerability, your humor, and your heart. Peri — you are extraordinary. Ad meah v'esrim.

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⏱️ Chapters with Timestamps

0:57 — Jon Is Back! Welcome Home After Surgery

4:29 — Introducing Allison Blass: Longtime Listener, First Time Guest

6:02 — Meet Allison: Giant Bear, Banned from Little League, Parent of Three

8:32 — Setting the Scene: Who Is Peri and Where Does the Story Begin?

9:08 — Allison's Career and Life Before the Diagnosis

10:05 — The First Signs Something Was Wrong: December 2024

15:58 — How Do You Tell Your Daughter She Needs Surgery?

25:10 — Perry's Mindset: Control, Preparation, and a Double Burger From Smash House

29:12 — April 9th: When the World Really Turned Upside Down

30:20 — Hearing the Word Malignant: "Everything Went Quiet"

32:30 — Turning Every Moment Into a Mitzvah: Hair Donation to Chai Lifeline

41:00 — What Allison Learned About Perry She Didn't Know Before

49:27 — NED: No Evidence of Disease — Perry Is on the Road to Survivorship

52:05 — Who Showed Up and Who Didn't: What You Learn About People in a Crisis

54:30 — "Don't Say If You Need Me" — The Most Important Lesson of the Episode

56:33 — How to Actually Help Someone Going Through a Hard Time

1:00:22 — The Hardest Part Is Now: Learning to Trust Again After Treatment Ends

1:08:06 — Allison's Message to Parents at the Beginning of This Journey

1:08:54 — Question of the Week: What Non-Kosher Food Do You Wish Was Kosher?

1:17:45 — Thank You Allison — Closing Brachos for Peri and the Blass Family&<

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Dave and Asher Hold It Down: Adulting, and the Things We Still Can't Figure Out

Jon's out. The substitute teachers are in charge.

In this episode, Dave and Asher fly solo for the first time in nearly two years of podcasting — and somehow manage to hold it together. Mostly. They spend most of the episode wrestling with one deceptively deep question: at what point did you realize YOU were the adult in the room? And does knowing that actually make you feel like one?

From colonoscopies to root canals and Gatorade-plus-antacid pre-fast routines, Dave and Asher take an honest — and very funny — inventory of what it means to be in your 40s. They talk about watching athletes you grew up idolizing retire and become millionaires while you're still figuring out the thermostat. They talk about mentoring the next generation at work while privately Googling how to hang a picture frame. They talk about laundry — a lot — and the creative workarounds that keep households running when you're too proud to admit you never really learned.

But underneath all the humor is something genuinely real: the weight and beauty of being the generation in the middle. Old enough to be the ones people turn to. Still young enough to remember when we thought the adults had it all figured out.

Plus: substitute teacher stories, a very eventful little Tyke's car incident, a parent-teacher conference confession, LeBron vs. Jordan, a prank from Toys R Us, and the world's most relatable Seder question.

Jon — we miss you. Come back soon.

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⏱️ Chapters with Timestamps

00:00 — Cold Open: Dave Asks His Wife About His Maturity. She Laughs.

00:27 — Welcome to the Carpool Guys Podcast

01:02 — Jon Is Out — Dave and Asher Go It Alone

01:22 — Substitute Teacher Stories: Mrs. Bach, Mrs. Henry, and a Saved Life

05:47 — Dave's Career Started as a Sub — Shout Out to Rabbi Hammer

07:16 — Smart Boards, Coaching Boards, and the HANC Basketball Championship

08:34 — Orange Juice, Decaf Coffee, and the Post-Fast Routine Debate

09:30 — The Bagel, Tuna, Herring, and OJ Breakfast Club

10:49 — The Big Question: When Did YOU Become the Adult in the Room?

12:10 — Colonoscopies, Pillboxes, Gout, and the Reality of Getting Older

14:09 — Root Canals, Dental Inheritance, and the First Cavity at 30

15:00 — When Athletes You Grew Up With Are Now Retired Millionaires

17:36 — LeBron vs. Jordan: The Eternal Debate

18:16 — Taking Pictures WITH Athletes vs. Taking Pictures OF Your Kids With Athletes

19:49 — Adulting at Work: You Don't Need All the Answers

21:00 — Mentoring the Next Generation: The Shift From Sink-or-Swim to Sit-Down-and-Talk

24:30 — Supervising Interns for the First Time: It's a Little Scary

25:47 — The 15-Year Window of Adulthood and What Comes After

27:09 — Taking Care of Your Health Differently: Recovery, Moderation, and Lactaid

28:01 — The Adulting Moment: Adding an Antacid to the Pre-Fast Routine

29:02 — Things Our Parents Did That We Wish We Knew How to Do

29:33 — The Picture That Fell Off the Wall and the Lesson About Wall Anchors

30:21 — Snaking a Toilet and the Pure Joy of Saving $500

31:39 — The Toys R Us Prank and Passing the Torch to the Next Generation

32:44 — Shout Outs: Aaron's Birthday, Dave's Wife's Birthday, Ayelet's Broken Arm

33:43 — Asher's Story: Rolling the Car Over Leia's Foot (Everyone Is Fine)

37:14 — Dave's Story: Ayelet "Fell Out of a Moving Car" (It

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