The PayPal Mafia of families

Hi friends,

"Why go through all the effort to build a custom family culture from scratch? Why not just lean into religion instead of reinventing the wheel?"

A friend asked us this recently. It’s a fair question.

Religion (or deep tradition) offers incredible infrastructure: shared beliefs, rituals, and a built-in community. It’s safe. It’s established.

Our answer? It’s the difference between joining Google and founding a startup.

If you join Google (or Citadel, or any established system), you get safety. You get a playbook. You get amenities.

But if you found a startup, you get to build from first principles. You get to ask: What do we believe? What works for us specifically?

In this week’s Q&A episode (thanks to all who sent in questions! 🙌), we dig into why we are choosing the "startup" path. We don't just want to raise kids who are comfortable inside an existing system. We want to raise the "PayPal Mafia"—kids who grow up to be independent thinkers, who eventually leave our pod to go build their own.

We also answer your questions on:

🤝 The Disagreement Protocol How do you handle it when you and your partner fundamentally disagree on a parenting decision (like giving an 8-year-old an iPhone)? We share the two business frameworks we use to break gridlock:

1. Weighted Believability (Ray Dalio): Deferring to the person with the most expertise in that specific area.

2. Disagree & Commit (Amazon): Supporting a decision 100% even if you voted against it. (We share a story about Hunter’s granola business to prove this works).

🤫 The "Friend's House" Dilemma What do you say when your kid asks, "But why does [Friend] get to eat sugar/watch TV/stay up late and I don't?" We share a framework for how to explain your values honestly—without judging the other family or acting like you hold the Absolute Truth.

❤️ The Belly Button Rule A quick check-in for your marriage: Are you getting enough time Side-by-Side (partnership) and Belly-Button-to-Belly-Button (intimacy)? If not, your Face-to-Face conversations are going to be a lot harder.

👇 Listen to the episode:

TMIT 41: The "PayPal Mafia" Strategy, Disagreeing with Your Spouse & The "Belly Button" Rule (Listener Q&A)
Spotify | Apple | YouTube

This is our last episode of 2025. We are spending the rest of the year in NYC – visiting friends & family, eating, and merrymaking around midtown with our kids for the first time since 2019. It turns out you can go home again (so long as the bags are under 50lbs). 

Thank you for building with us this year. We’ll see you in January!

Grateful, messy, and merry as ever,
Danielle & Greg

Clips from this week’s Q&A

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