If you missed Part 1, check out Episode 26, and then return for Part 2!

In Part 2, Matti and Ethan's conversation focuses on what parenting actually requires - and why the answer may have more to do with support and community than deciding who is naturally “good” at being a parent.

They discuss the idea of the “good enough parent,” why parents don’t need to respond perfectly to every situation, and how mistakes and repairs can actually strengthen relationships.

Referenced in This Episode

• The Wall Street Journal — “When One Nanny Isn’t Enough, CEO Parents Hire a Whole Team”

https://www.wsj.com/lifestyle/relationships/ceo-parent-nanny-assistant-teams-hiring-20d3a9c0

Chapters

00:00 A Controversial Question

03:05 Parenting Was Never Meant to Be a Solo Job

07:18 What Does It Mean to Be “Good Enough”?

13:00 Why Parents Don’t Have to Get Everything Right

16:58 The Power of Repairing Mistakes

20:31 Is It Gonna Be Fine?

Matti is joined by psychotherapist Ethan Weiss, MS, LCSW of Yes & Therapy LLC to explore what happens when parenting starts to feel like something we should optimize.

Inspired by a recent article about wealthy parents outsourcing the everyday work of raising children, they discuss the difference between outsourcing childcare and outsourcing parenting, whether quality time can replace quantity time, and why the repetitive, ordinary moments of parenting might matter more than we realize.

They also explore why “I just want my kid to be happy” is more complicated than it sounds—and why experiencing difficult emotions may be an important part of growing up.

This is Part 1 of a two-part conversation. Part 2 continues next week in Episode 27, where the conversation shifts to what parenting really requires.

Referenced in This Episode

• ​The Wall Street Journal — “When One Nanny Isn’t Enough, CEO Parents Hire a Whole Team”
• ​https://www.wsj.com/lifestyle/relationships/ceo-parent-nanny-assistant-teams-hiring-20d3a9c0

Chapters

00:00 Intro

02:07 What Happens When We Outsource Parenting?

12:00 Why Everyday Moments Matter

25:33 Is Happiness the Goal?

36:47 Helping Kids Build Resilience

44:23 Next Time, on Part 2

America’s favorite brother-in-law is back! David joins Matti for a wide-ranging conversation about a surprisingly big question: when we care about someone, should we protect them from the world... or prepare them for it?

We start with parents, kids, weight, appearance, and the danger of planting insecurities in someone who never saw themselves as having a problem. Then David and Matti disagree over "Bug Boy," a seven-year-old obsessed with bugs who may be struggling socially. Should his parents simply let him be himself, or guide him to fit in with the world around him?

From there, the conversation moves to dating and how much physical attraction plays a role in our society, focusing on a very questionable rejection reason on a live blind-dating show. We then expand into the bigger question of why looks seem to matter more and more as we get older, including:

• Are we now expected to stay young, healthy, attractive, and optimized forever?
• And when does taking care of yourself become an exhausting attempt to outrun aging?

David and Matti don’t see everything the same way—but they do agree on one thing: it’s important to help people navigate the world while also making them feel like they wholeheartedly belong in it.

Referenced in this Episode:

• The Free Press — “Can I Tell My Daughter She’s Fat?”
  https://www.instagram.com/p/DbGKcMOAp6t/

• Updating — Live Blind Datinghttps://www.instagram.com/p/DbEU0xNgr96/https://www.instagram.com/p/DbEpXriFnlT/https://www.instagram.com/p/DbEzsXkEnnL/

• Bloomberg — “Millennial Men Are Rethinking What It Means to Be Hot & Healthy in Middle Age”https://www.bloomberg.com/news/features/2026-05-01/millennial-men-are-rethinking-what-it-means-to-be-hot-healthy-in-middle-age

Smartphones give us an incredible amount of convenience, connection, entertainment, and information. But somewhere along the way, we may have traded away a few things we didn’t realize we’d miss.

This week, Matti looks at life before smartphones, the rituals and experiences that once filled our days, and why some of those seemingly outdated things still hold so much appeal. He also explores the growing fascination with MySpace and the possibility that people are getting a little tired of an internet built around algorithms, ads, optimization, and constant competition.

Maybe progress doesn’t mean everything from the past needs to disappear. Maybe we can have the best of both worlds.

Referenced in this episode:

• The Atlantic — “What Did People Do Before Smartphones?”
  https://www.theatlantic.com/technology/archive/2023/07/before-smartphones-boredom/674631/
• BuzzFeed — “19 Things We’ll Never Get to Experience Again Because of Technology”
  https://www.buzzfeed.com/daves4/did-one-last-time

How is AI actually changing the workplace?

In Part 2 of our AI conversation, Cindy and Matti discuss what happens when artificial intelligence moves from the classroom into our careers. We react to a an interview with the CEO of Levi’s, unpack why so many corporate AI conversations feel filled with buzzwords, and explore what employees really want to hear from leadership.

We also discuss whether Gen Z is truly unprepared for today’s workplace—or whether the workplace itself has changed more than people realize—and wrap up with some hilarious real-life intern stories.

If you missed Part 1 (Episode 22), you can take a listen here on your podcast platform of choice: https://pod.link/1879411435

Referenced in this Episode:

• Today Show / Levi’s: Levi’s CEO discusses how the company is using AI (Instagram clip)https://www.instagram.com/p/Dak9vtVFFqD/

• The Wall Street Journal: A New Lost Generation: Why Gen Z Is Unprepared for the Workplace
  https://www.wsj.com/lifestyle/careers/gen-z-worker-skills-294463f6?mod=e2li

• Media War & Peace by Evan Shapiro (Substack Newsletter)https://eshap.substack.com  

• Wall Street 360: Top 30 Wall Street Intern Storieshttps://www.wallstreet360.co/blog/top-30-wall-street-intern-stories

AI is transforming education faster than most schools can adapt.

In Part 1 of this two-part conversation, Cindy is back, and we discuss how artificial intelligence is changing the classroom—from ChatGPT and homework to critical thinking, college, and the future of learning.

Is AI making students smarter, or simply making it easier to avoid learning? How should schools respond? And what skills will actually matter in an AI-driven world?

Referenced in this Episode

• CBS Chicago: UChicago curbing AI usage by banning technology in class for first-year law studentshttps://www.youtube.com/watch?v=ejIxTTLsgzw

• The Wall Street Journal: High-Earner Families Are Ditching Traditional Schools for Life Skills and AIhttps://www.wsj.com/us-news/education/alternative-education-wealthy-families-ai-cd7922b3

Public reactions to the death of Senator Lindsey Graham sparked a much bigger conversation than politics. In this episode, Matti and guest co-host David explore empathy, political violence, social media, privacy, and whether we’ve become too quick to dehumanize people we disagree with.

Rather than taking sides, they ask a broader question: How do we disagree without losing our humanity? Along the way, they discuss digital permanence, public speculation, LGBTQ identity, and why giving grace may be more important—and more difficult—than ever.

Referenced in this Episode:

• Ana Navarro on The View reacting to the death of Lindsey Grahamhttps://www.youtube.com/watch?v=Y18pItzUI1M&t=17s

• Brad Polumbo’s response to The View segment (Instagram)https://www.instagram.com/p/DaxqJLYlM5v/

• Jesse James Rose on marginalized groups following Lindsey Graham’s death (Instagram)https://www.instagram.com/p/DawCgyeuapj/

• “What If It All Came Out?” — Bridget Read (New York Magazine)https://nymag.com/intelligencer/article/your-digital-self-is-vulnerable.html

What makes a family? What makes a relationship? And can one person realistically meet all of our needs?

This week, Matti sits down with writer and author Sophie Lucido Johnson (@sophielucidojohnson) for a conversation that begins with polyamory but quickly expands into something much bigger: friendship, chosen family, communication, jealousy, and the many ways people create meaningful connection.

Whether or not non-monogamy is for you, this conversation offers an opportunity to better understand a relationship style that is often reduced to stereotypes—and, in the process, explores bigger questions about what we expect from the people we love.

Referenced in This Episode

• Kin: The Future of Family by Sophie Lucido Johnson
  https://www.simonandschuster.com/books/Kin/Sophie-Lucido-Johnson/9781668060650
• The Cut Documentary: Beyond “The One”: Exploring Modern Polyamoryhttps://www.thecut.com/2019/02/beyond-the-one-exploring-modern-polyamory.html

A simple question about BlackBerry's evolution turned into a much bigger conversation about reinvention.

What does it really mean to reinvent yourself? And why do some people embrace change while others struggle to let go of who they’ve always been?

This week, I’m joined by Wendy Battles, host of the Reinvention Rebels podcast, for a thoughtful conversation about second acts, identity, and what it takes to start over.

We explore why comparison can quietly derail personal growth, how people-pleasing keeps us stuck, whether reinvention is better done publicly or behind the scenes, and why the things that seem like detours in life often become the experiences that shape us most.

Whether you’re changing careers, starting a creative project, entering a new chapter, or simply wondering what’s next, this episode is a reminder that reinvention isn’t about having all the answers—it’s about giving yourself permission to begin.

Referenced in this episode:

• BlackBerry (2023 film) — Available on Netflix
• Wall Street Journal: BlackBerry’s QNX Software Powers Millions of Cars — https://www.wsj.com/tech/blackberry-qnx-software-cars-bf2a2280
• Reinvention Rebels — www.reinventionrebels.com

As a teacher, parent, and mental health professional, David shares what he’s seeing firsthand when it comes to kids and social media, why he has mixed feelings about government bans, and how schools are navigating the growing push to keep phones out of the classroom.

We also dive into AI’s expanding role in healthcare, the surprising ways GLP-1 medications like Ozempic and Mounjaro may be helping beyond weight loss, and whether using them is “cheating” or simply leveling the playing field.

Referenced in this episode

• Good Morning America: “Should Kids Be Banned from Social Media?”https://youtu.be/ZS1ivHjFhgk?is=Zq4ms7y0znz9Wq6F

• NBC News: “AI Helps Diagnose Rare Diseases at Boston Children’s Hospital” https://youtu.be/J65hHZa8oic?is=cgzFdxk0yItivEc0

• The Washington Post: 13 surprising ways GLP-1s may benefit the body, according to sciencehttps://www.washingtonpost.com/health/2026/03/27/glp1-ozempic-benefits/

• The Washington Post: Science around GLP-1 drugs and cancer is suddenly getting a lot more interestinghttps://www.washingtonpost.com/health/2026/06/03/science-around-glp-1-drugs-cancer-is-suddenly-getting-lot-more-interesting/