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The Carpool Guys

The Carpool Guys

By: Jon Ackerman
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About this listen

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.

© 2025 The Carpool Guys
Episodes
  • The Pilot: The Best Advice We Ever Got

    The Pilot: The Best Advice We Ever Got
    Oct 23 2025

    🎙️ 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
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    44 mins
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