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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

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

Follow us on Instagram @carpoolguyspod

Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!

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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!

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

Follow us on Instagram @carpoolguyspod

Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!

Send us Fan Mail

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

🎙️ Rate and review The Carpool Guys on Apple Podcasts. Five stars please!

📩 carpoolguyspod@gmail.com

📱 @carpoolguyspod

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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

Please rate and review The Carpool Guys!

You can email us at carpoolguyspod@gmail.com

Follow us on Instagram @carpoolguyspod

Send us a question, a comment, birthday wish, shoutout, or anything else fun and positive, and maybe we'll feature your addition on the next episode of The Carpool Guys Podcast!