In this episode of Who Cares?, Jay O’Brien and Jeff Jackel peel back the layers on ambition, burnout, money, and meaning. From funny travel chaos with kids and a Maui vacation gone logistically wrong, to the existential question of why we work so hard in the first place — this episode hits every note: hilarious, heartfelt, and uncomfortable in all the right ways.

Here’s what you’ll walk away with:

🧠 A new lens on success and financial freedom:

Jeff explains why he won’t pay for his kids’ college. Jay talks about what financial freedom means now that he’s having a daughter. They break down the trap of saving for a future that might never come — and how “Die With Zero” completely changed their perspective.

🌴 Real-life stakes of unplugging:

A saga of trying to book a family trip to Hawaii using credit card points turns into a metaphor for how complicated we’ve made our lives — even when we’re trying to rest. Jay’s planning his 10th anniversary and struggling to unplug. Jeff asks: is it even worth it if you’re never really present?

💰 Is wealth the goal — or just comfort? This episode doesn’t shy away from tough money questions:

Are we chasing wealth or safety? Do we build empires just to never enjoy them? Are we actually helping people — or padding our own anxiety? What’s the ROI on being “always on”?

👶 Parenting in a different world:

Jeff and Jay explore how raising kids changes your relationship with time, money, and legacy. They reflect on how their generation sees travel, experiences, and hustle differently than their parents — and what kind of childhoods they want to give their own kids.

👩‍💻 Annie’s ( @annieelise ) True Crime Empire: Jay gives a heartfelt shoutout to his sister Annie, who’s built a hugely successful true crime content channel while navigating motherhood and postpartum.

If you’ve ever:

- Felt guilty for taking time off

- Asked yourself, What am I even doing this for?

- Wanted to give more but felt constrained

- Wondered if success is just a shinier hamster wheel...

This episode is your mirror!

This is more than a podcast — it's a reminder: you won’t remember the email you didn’t answer, but you will remember the time your kid asked for one more cannonball and you said yes.

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