The Carpool Guys
The Carpool Guys Podcast is where three real Jewish dads- Asher Dworetsky, Jon Ackerman, and Dave "From Flatbush" Tannenbaum, buckle up for unfiltered conversations about fatherhood, marriage, midlife, and the beautiful chaos of raising a family in the Jewish community today.
These guys have made mistakes, learned lessons the hard way, and have just enough life experience to give out their not so expert advice. From career crossroads to screen time battles, from Shabbos table debates to parenting fails, from Israel and what it means to us as Jews to the everyday moments that make you laugh, cry, and question every decision you've ever made... The Carpool Guys go there.
Whether you're married or single, a parent or a kid who still needs one, navigating life or just trying to figure it all out... this is your podcast. Humor, heart, and meaning, every other week. No filter. No script. Just real talk from three guys who are very much still figuring it out too.
Buckle up. New episodes every other week on Apple Podcasts, Spotify, YouTube, Amazon, or wherever you get your podcasts!
The Carpool Guys
Can You Survive Winter Vacation Without Losing Your Mind?!? ⚠️ Warning ⚠️ we may have already 🤯🤯🤯
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Winter break sounds relaxing — until it actually begins.
In this episode of The Carpool Guys, Asher, Dave, and Jon dive into the realities of winter break and family vacations, exploring the excitement, stress, anxiety, and unexpected joy that come with extended time off and traveling together. Through relatable stories and plenty of humor, they unpack why winter break often feels like anything but a break.
The conversation touches on the pressure to create the “perfect” family vacation, the stress of travel and logistics, and the temptation to compare your holiday experience to everyone else’s highlight reel. Asher, Dave, and Jon make the case for prioritizing authentic experiences over perfect photos, embracing the chaos when things go wrong, and recognizing that the most meaningful holiday memories are often unplanned.
They also share practical, real-life advice on planning family vacations that actually fit your family’s needs, avoiding empty parenting threats while traveling, making intentional time for your spouse during school breaks, and using humor as a powerful tool to navigate family challenges.
Whether you’re packing bags, already on the road, or just trying to survive winter break at home, this episode offers laughter, perspective, and reassurance that you’re not doing it wrong — you’re just living real life.
- 00:00:00 Introduction to Winter Break
- 00:03:00 Family Vacation Anxieties
- 00:06:00 The Importance of Authentic Experiences
- 00:09:00 Navigating Family Dynamics
- 00:12:00 Creating Lasting Memories
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!