The Carpool Guys

Jon Ackerman
  • 5.0 (4)
  • JUDAISM

The Carpool Guys Podcast is where real-life dads — Asher Dworetsky, Jon Ackerman, and Dave “From Flatbush” Tannenbaum — share unfiltered conversations about family, fatherhood, work, and the wild ride of midlife. They’ve made mistakes, learned lessons (mostly the hard way), and have just enough life experience to be dangerous with advice. From career crossroads to raising kids in a digital world, from marriage moments to dad fails, The Carpool Guys dive into it all with honesty, humor, and heart. Whether you’re commuting, carpooling, or just catching your breath between responsibilities, this is your front-seat pass to authentic midlife banter, questionable wisdom, and a few laughs along the way.

Episodes

  1. 1D AGO

    Aliyah Anxiety: Let’s Talk About Why This Freaks Us Out (And Laugh About It)

    Send us a text What starts with a painfully awkward synagogue moment (you know the one, that late guy who somehow blocks everyone’s view) quickly turns into a much bigger conversation. This week, Asher, Dave, and Jon dive into the very real and increasingly common phenomenon of Aliyah Anxiety, the emotional tension between loving Israel, feeling spiritually connected to Jewish life in Israel, and also being genuinely happy, rooted, and fulfilled living in the United States. The guys unpack the emotional, mental, and practical challenges of making Aliyah, including identity, family considerations, community pressure, Jewish values, and the fear of making the “wrong” life decision. Along the way, they mix thoughtful reflection with humor, stories, and classic Carpool Guys travel mishaps. This episode touches on Jewish identity, Jewish community, modern Orthodox life, moving to Israel, work-life balance, parenting, and the emotional complexity of big life choices - all while keeping things honest, relatable, and funny. If you’ve ever felt pulled in two directions - Israel and America, idealism and reality, dreams and day-to-day life - this one’s for you. 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!

    51 min

  2. DEC 10

    The Qualities We Admire In The Leaders We've Worked For

    Send us a text In this episode of The Carpool Guys Podcast, the guys explore how everyday leadership and small acts of kindness can create a powerful, lasting impact on the people around us. Through real-life stories, including Asher’s unforgettable car rescue adventure (Thank you Chaveirim!) they highlight the importance of doing the little things, showing up for others, and staying grounded in the middle of life’s chaos. The conversation dives into essential leadership qualities like empathy, humility, approachability, and consistency. Simple actions like helping a friend, supporting a neighbor, and staying (Very) patient with family, often demonstrate stronger leadership than any big speech or title. With humor, heart, and relatable stories about parenting, family life, teamwork, and growth, this episode reminds listeners that true leadership happens in the small moments: the ones no one applauds but everyone remembers. 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!

    44 min

  3. NOV 25

    It's Thanksgiving Week: The Best Week of the Year!

    Send us a text This week on The Carpool Guys Podcast, Jon and Asher take the wheel for a special Thanksgiving edition — and yes, Dave’s off the hook (or maybe just on turkey duty). In this cozy, laugh-filled episode, the guys share their love for Thanksgiving, from family traditions and favorite foods to the real power of gratitude. They swap personal stories about family gatherings, reflect on what makes this time of year so meaningful, and dive into listener-submitted Thanksgiving traditions that will have you smiling all the way to the dinner table. Along the way, they explore:  🦃 Why Thanksgiving might just be the best week of the year 🍗 How teamwork makes the turkey work 🥧 Food, family, and a side of Black Friday chaos 🕯️ The intersection between Thanksgiving gratitude and Chanukah gift-giving 🎬 Their favorite  family movie picks for the long weekend From heartfelt reflections to hilarious moments, Jon and Asher remind us that gratitude isn’t just for Thanksgiving — it’s a way of life. Chapters 00:00 The Best Week of the Year 02:42 Thanksgiving Traditions and Family Connections 05:32 Gratitude and Its Importance 08:43 The Role of Teamwork in Thanksgiving 11:39 Reflections on Food and Memories 14:40 The Significance of Thank You 17:41 The Power of Gratitude in Leadership 21:23 The Importance of Family and Gratitude 24:49 Cholent Hotline: A Culinary Idea 25:57 Thanksgiving vs. Yontif: A Cultural Comparison 30:30 The Flexibility of Thanksgiving Celebrations 32:43 Gift-Giving Traditions: Chanukah and Beyond 34:56 Holiday Decorations: The Challenge of Setup and Takedown 39:01 Thanksgiving Traditions from Listeners 40:18 Thanksgiving Traditions and Family Stories 43:15 The Beauty of Fall and Personal Reflections 48:51 Work-Life Balance and Thanksgiving Anticipation 49:19 Movie Recommendations for Family Time 53:32 Gratitude and Thanksgiving Reflections 54:54 Black Friday Shopping Insights 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!

    52 min

  4. NOV 20

    The Drive By: Dave From Flatbush on Giving His Kids Haircuts

    Send us a text In this week’s mini Drive By episode, Dave From Flatbush shares what happens when dads decide to “save a few bucks” and give their kids haircuts at home. ✂️💈 Spoiler alert: the results weren’t exactly professional. From uneven bangs to emotional damage (mostly Dave’s), this quick pit stop of parenting chaos will make every parent nod, laugh, and say, “Yup… been there.” Catch this bite-sized dose of dad humor from The Carpool Guys Podcast — a little off the top, and a lot off the rails. 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!

    1 min

  5. NOV 12

    Mini Mentors: Lessons From Our Children

    Send us a text In this lively episode of The Carpool Guys Podcast, the dads dive headfirst into the chaos, curiosity and comedy of learning from life's greatest teachers... our kids! From epic tantrums and jet-lagged meltdowns to the unforgettable concept of “foreign tushies” (trust us, you’ll never hear that phrase the same way again), this episode reminds us that even in the messiest moments, there’s always something to laugh about... and learn from! Along the way, Asher, Jon, and Dave share personal stories about family life, the importance of staying curious, and the lessons they’ve learned from their own kids — sometimes the hard way. Whether you’re a parent, future parent, or just someone who loves a good laugh, this one’s for you. Chapters Chapters00:00:00 Introduction: Jet Lag and Parenting Struggles00:03:00 Humor in Parenting:  Daily Challenges00:06:00 Early Risers: Kids and the Mystery of Extra Sleep00:12:00 Fan Mail: Foreign Tushies00:18:00 Lessons from Children: Insights and Life Lessons00:21:00 Curiosity and Openness: Essential Parenting Qualities00:24:00 Evolving Family Dynamics: Growing with Your Children00:27:00 Parenting Mishaps: Laughing Through the Chaos00:30:00 Closing Reflections: Gratitude and Parenting WisdomPlease 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!

    49 min

  6. NOV 6

    The 2 Minute Ride: Asher on High School Open Houses

    Send us a text The 2 Minute Ride: High School Open Houses — Why Are We Still Nervous? You’d think we’d be over it by now… but apparently, high school open houses still make us sweat. 😅 In this quick pit stop from The Carpool Guys Podcast, Asher takes the wheel to talk about the surprisingly real anxiety that comes with walking those shiny hallways... again. This “2 Minute Ride” hits every parent right in the nostalgia (and the nerves). PLUS: Wait... WHO fell asleep? It’s fast, funny, and uncomfortably relatable. Buckle up! It’s only two minutes, but it’s a ride. 🚗💨 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!

    2 min

  7. OCT 29

    Rejected! It's Not You... It's Life!

    Send us a text Rejection hurts- Whether it’s not making the team, missing that dream school, or just getting ghosted by opportunity itself. In this episode, The Carpool Guys — Asher Dworetsky, Jon Ackerman, and Dave “from Flatbush” Tannenbaum — take the scenic route through life’s “no’s,” sharing personal stories that hit home (and sometimes hit funny). From playground heartbreaks to midlife curveballs, the guys get real about what rejection teaches us, and how to help our kids grow from it too. They explore what it means to support your child without bubble-wrapping them, how to handle disappointment with grace, and why sometimes the best lessons come from not getting what we wanted. It’s heartfelt, honest, and just the right amount of hilarious — a reminder that rejection isn’t the end of the road… it’s just another lane on the highway of life. Chapters 00:00 Introduction and Initial Feedback 04:35 The Topic of Rejection 05:39 Personal Stories of Rejection 15:40 Parental Perspectives on Rejection 22:51 Growth Through Rejection 25:33 Encouragement vs. Discouragement in Growth 27:44 The Brutality of Letting Go 30:37 Navigating Difficult Conversations 32:27 The Complexity of Termination 35:02 Feedback and Growth in Management 37:16 Parenting and Handling Rejection 43:51 The Role of Coaches and Parents 46:46 Teaching Resilience in Children 51:51 Fear of Rejection and Its Impact 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!

    57 min

  8. OCT 23

    The Pilot: The Best Advice We Ever Got

    Send us a text 🎙️ The Pilot — The Best Advice We Ever Got Welcome to the very first ride of The Carpool Guys Podcast, where three dads — Asher Dworetsky, Jon Ackerman, and Dave “from Flatbush” Tannenbaum — talk about life, work, family, and all the chaos in between. In this inaugural episode, the guys open up about what it really means to balance personal and professional life in today’s world. From lighthearted dad banter to surprisingly deep moments, they share the best advice they’ve ever received, what authenticity means at midlife, and how to take action when opportunity knocks. Along the way, they swap hilarious dating stories, talk about mentorship, and reflect on the lessons that only come from making a few (okay, a lot of) mistakes. It’s funny, heartfelt, and refreshingly real — the perfect mix of dad humor, life advice, and mid-career honesty that makes you feel like you’re right there in the carpool with them. 🚗 Chapters 00:00 — Welcome & Introductions 06:32 — Navigating Life’s Challenges: The Best Advice Received 17:23 — Dating Stories & Lessons Learned 22:38 — Dating App Disasters 25:54 — The Importance of Taking Action 33:10 — Life Lessons from Personal Experiences 38:40 — Professional Growth & Mentorship 44:54 — Asking for What You Want 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!

    44 min
  • 8 Episodes

Ratings & Reviews

5
out of 5
4 Ratings

About

The Carpool Guys Podcast is where real-life dads — Asher Dworetsky, Jon Ackerman, and Dave “From Flatbush” Tannenbaum — share unfiltered conversations about family, fatherhood, work, and the wild ride of midlife. They’ve made mistakes, learned lessons (mostly the hard way), and have just enough life experience to be dangerous with advice. From career crossroads to raising kids in a digital world, from marriage moments to dad fails, The Carpool Guys dive into it all with honesty, humor, and heart. Whether you’re commuting, carpooling, or just catching your breath between responsibilities, this is your front-seat pass to authentic midlife banter, questionable wisdom, and a few laughs along the way.

Information

  • Creator
    Jon Ackerman
  • Years Active
    2K
  • Episodes
    8
  • Rating
    Clean
  • Copyright
    © 2025 The Carpool Guys
  • Show Website
    The Carpool Guys

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