Why go through the massive effort of building a custom family culture from scratch? Why not just lean into religion or tradition instead of reinventing the wheel?

In our final episode of 2025, we open up the mailbag to answer your questions. We discuss the tension between inheriting a system vs. building one, and why we are trying to raise the "PayPal Mafia" of families rather than just comfortable employees.

We also break down the specific business frameworks we use to resolve parenting arguments without resentment, and how to handle the inevitable "But my friend gets to do it!" conversation.

In this episode, we cover:

• [01:14] The "Startup vs. Google" Analogy: Why we chose to build our values from first principles rather than adopting a pre-packaged playbook (like religion).
• [05:50] The PayPal Mafia Strategy: Why we want our kids to eventually leave and build their own pods, rather than staying comfortable in ours forever.
• [07:49] Family is a Team, Not a Democracy: How to balance giving kids a voice while maintaining parental leadership.
• [11:46] The "Friend's House" Dilemma: A script for explaining family values to your kids without judging other families.
• [20:18] The Disagreement Protocol: How we use Ray Dalio’s "Believability" and Amazon’s "Disagree and Commit" to solve parenting deadlocks (featuring the "Granola Business" story).
• [26:48] The 3 Types of Connection: Why every couple needs time Face-to-Face, Side-by-Side, and Belly-Button-to-Belly-Button.
• [36:00] The Anti-Martyr Mindset: Why checking all the boxes doesn't guarantee a tantrum-free life (and why that’s okay).

Resources & Episodes Mentioned:

• TMIT 28: How We Divide, Conquer, and Connect – The Shared Operating System Behind Our Marriage
• TMIT 37: Disagree & Commit
• Concept: Ray Dalio’s "Weighted Believability"
• Concept: The "PayPal Mafia" (Peter Thiel, Elon Musk, Reid Hoffman, David Sacks, Max Levchin, etc.)

We often blame the phone for stealing childhood. But what if the issue isn't just the presence of the smartphone, but the absence of the landline?

When the landline died, we lost a major opportunity for growth. We lost the environment where kids learned to organize their own social lives and navigate awkward conversations with intermediaries (“Hi Mrs. Neufeld, is Greg home?”). Perhaps most importantly, we lost the practice of "cognitive patience": the ability to just sit and listen to a voice, with zero notifications, games, or screens to distract us.

To explore this, we sat down with Chet Kittleson, founder of Tin Can, to discuss a radical, growing trend: Bringing back the landline.

We discuss why giving children a dedicated, voice-only device like Tin Can is a master move in building family culture—not because we want to live in the past, but because we want to give our kids agency in the present.

And, along the way, we explore what it’s like for Chet as a husband, father, and son to be the founder of a fast-growing company that is deeply connected to his family values.

In This Episode, We Cover:

• The "Family Line" vs. The Personal Device: Why giving every family member a personal device killed the shared experience of the home phone, and how bringing it back helps kids learn to navigate the world.
• What is Tin Can? A look at the hardware that uses WiFi to work like a landline, but with a "whitelist" feature so kids can only call (and receive calls from) numbers parents approve.
• Cognitive Patience: The profound difference between a chaotic FaceTime call and the focus required to sit, listen, and hold an audio-only conversation.
• Founder & Father: Chet opens up about the challenges of building a high-growth startup. He shares his specific rituals for transitioning from "CEO mode" to "Dad mode"—including an e-bike commute that helps him shed the stress of the day.
• Teaching Through Struggle: How Chet uses his work to teach his kids that they too can do anything they set their minds to.
• Favorite Family Tradition: Don’t miss Chet’s unique family tradition at the end! (Hint: it involves Brussels sprouts and a baseball bat)

Resources Mentioned:

• Get your own Tin Can: www.tincan.com
• Follow Tin Can on Instagram: @tincan.kids

We did something that sounds crazy: We gave our 8-year-old an iPhone 15 Pro. But there is a strategy behind the screen.

In this episode, we are exploring a new frontier: Family AI. We believe this is a pivotal moment where parents can either fear the technology or learn to lead with it. Our goal? To shift from being a "consumer family" (passive scrolling) to a "creator family" (active building).

We break down our personal framework for using AI at home—The 3 C’s: Clarify, Coach, and Create.

In this episode, we cover:

• The iPhone Decision: Why we gave Hunter a "device" (not a phone) and how we locked it down using Apple's native settings.
• Clarify: Using tools like the Limitless Pendant to capture the "ground truth" during disagreements and using voice-to-text to save brainpower during brainstorming.
• Coach: How we use AI as a neutral third party to mediate sibling arguments (like Maverick vs. Hunter) and navigate health scares in real-time.
• Create: Moving from consumption to creation—from designing our Thanksgiving gratitude tables to making explainer videos for school using NotebookLM.

Mentioned in this episode:

• 🔗 Limitless AI: limitless.ai (Recently acquired by Meta!)
• 🔗 NotebookLM: notebooklm.google.com
• 🔗 OpenAI Whisper: openai.com/index/whisper

Watch the full video version of this episode on Spotify.

Join us as we figure this out in real-time. It’s messy, it’s new, but it’s the most important addition to our family workflows ever.