As the father of two prep school students, I was very eager to meet this week’s guest. Jeffrey Selingo has written about college admissions for more than 25 years and is a New York Times bestselling author of four books, including Who Gets in and Why and his latest, Dream School: Finding the College That’s Right for You. Drawing on two years of research and a survey of 3,000 parents to give families permission to think more broadly about what signals a “good” college for their child, Jeff outlines the excellent choices our kids have outside of the Top 20 schools that get so much of our attention. I found his book a reassuring and therapeutic guide as our family begins the college search process. The basic message is that there are a lot of great schools for our kids out there and, with a little effort, you and I can find a place where our son or daughter will belong and thrive. And isn’t that the point? In this conversation, Jeff and I discuss the pressures surrounding elite college admissions, the evolving landscape of higher education, and the importance of finding the right fit for students. We explore the long-term financial implications of college choices, the impact of student debt, why parents are less willing to stretch financially for kids’ college expenses, and the value of college experiences beyond academics. The discussion also touches on the competitive nature of elite schools, the future of college admissions, and the weird middle ground colleges have adopted around standardized testing. A regular contributor to The Atlantic, The New York Times, and The Wall Street Journal, Jeff is also a special advisor to the president. He lives near Washington, D.C., with his own college-bound children.

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Hello friends. On this week’s episode, I read to you—like a daddy rocking his baby to sleep—the most recent posts from my Substack newsletter, which you can find here. (You can subscribe for free or pay a few bucks, if you want to support my work, but really I just appreicate you reading / listening and sharing.) These essays cover both life in general and some political stuff also. I put the political ones at the end, so you don’t have to involve yourself in that, if you don’t want to. But please do notice the balanced nature of my analysis, in that I am pointing out the flaws of both Left and Right, though it probably feel as if I’m being more critical of whichever team you’re on! Ain’t that weird?

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Imagine being told you have a terminal illness. Would it change the way you approach each day? Two years ago, Thad Reichley went to the doctor because he had the flu. When initial attempts to address his symptoms were unsuccessful, additional procedures revealed the presence of three dozen tumors in the lining around his lungs. He was diagnosed with stage 4 metastatic melanoma. There is no known cure for the disease. A father, husband, educator, and pro-level endurance athlete, Thad’s “job” over the past 24 months has been to fight cancer and stay alive. In addition to his treatments' side effects (fever, vomiting, inflammation of the eyes, and savage bouts of colitis), Thad has learned to navigate the negative “you are not enough" voices in his head. He’s also come to change his expectations about what makes a good day. “Sometimes” he says, that while trying to carpe every diem, “just walking the dog has to be enough.” Thad and I know each other through his wife, Leigh, who was my colleague on the sales team at Facebook in LA. She’s a very funny, very committed person who, as you will hear, is no stranger to cancer. I am grateful to Thad for sharing his story and hope it inspires YOU to go to the doctor if you haven’t been in a while. As importantly, I hope that it reminds you to cherish and protect your health and loved ones for as long as you have them.

Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at Stanford University, where she went on to win both individual and team national championships and became Nike Golf’s very first NIL sponsored athlete. But when the time came to turn pro, Rachel decided that a life on the road and in the spotlight wasn’t for her. Instead, she earned and accepted her commission as an officer in the U.S. Air Force Reserve. I was very pleased to speak with Rachel, not just because she is a person of exceptional talent and character, but because she is also the daughter of my Rhodes College friends, Stacy and Robert Heck.

Raj Goyle is running for Comptroller of New York state, and he wants your support. He’s got mine because I think Raj is what America is all about. A first-generation Indian-American, Duke undergrad and Harvard Law grad, Raj was the co-founder of Bodhala, a legal spend analytics and management platform which he and team sold to Onit. As the leader of Phone Free New York, Raj led a bi-partisan effort to get phones out of the classroom across New York state. And now he wants to take his immense talent and experience to Albany for the most important position (Comptroller!) you’ve never thought about. As you’ll hear, there’s plenty that Raj and I disagree about. But he’s the kind of person we need more of in government: a smart, driven leader who wants to make government work for citizens. Among lots of other things, Raj and I discuss:

Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed about his new memoir, Hard Lessons From the Hurt Business: Boxing and the Art of Life in which he shares stories about discipline, sobriety, and self-mastery. Ed and I talk bout how emotional control can outpower ego, how true masculinity is rooted in accountability, and why forgiveness is the ultimate form of strength. He also discloses that he (loves and) likes his wife! Thanks to Rob Henderson for bringing Ed to my attention.

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🥊Learn more about Ed here 🥊

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John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really, really burned, over 100% of his body, 87% of which were third-degree burns. Doctors gave him less than 1% chance of living and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, he got through it. His journey back took years, required dozens of surgeries, and cost him all of his fingers. Today, John is a world-renowned inspirational speaker who addresses large audiences around the globe. John is also the author of the best-seller On Fire!: 7 Choices to Ignite a Radically Inspired Life and In Awe: Rediscover Your Childlike Wonder Unleash Inspiration, Meaning, and Joy. He hosts the Live Inspired podcast. John and I have a lot in common. We were both one of six kids in a big, Catholic family and raised by amazing parents who were married for over 50 years and whose humility and grace inspire us to this day. We’re both husbands and dads, and both want our audiences to be radically aware of the value of their lives and the opportunity to make every day count. In this conversation, we discuss the importance of:

Living in the moment

Gratitude

Family

Courage

Friends who will fight for you

Finding your Talents

“Saying Yes to being used for good.”

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Watch the trailer for Soul On Fire: https://www.youtube.com/watch?v=CslVGLETWps

Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the fun, non-obvious aspects of money and emotions, such as how comparison drives us crazy and why our bias toward action —doing something when things are going wrong — often leads to worse investment results. He offers small tips (like giving your savings account a name) that will help you save more and spend less. Daniel shares lessons from his (Mormon) mission to the Philippines, and we both reflect on how our frugal parents informed who we are today, in almost entirely (but not 100%) good ways. From the dangers of debt and overconfidence to escaping the toxic loop of “I’ll be happy when…,” we cover a lot of ground and have lots of laughs along the way. Listening to these two money-talkers with great hair will improve your life!

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*don’t forget the “PhD” part or he gets very mad.😁

Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised in two-parent homes have better personal and professional outcomes (ON AVERAGE) than those raised in single-parent homes. Specifically, two-parent homes produce

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Learn more about Melissa Kearney here.

If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most urgent challenges. In this week’s episode, Craig and I discuss the early days of Craigslist, its radical “revenue-minimization” strategy, and how its simple tools changed the classified ads game in the late ’90s. He told me how Sunday school values shaped his approach to business, why he demoted himself to customer service rep, and what he learned by hiring a CEO to run the company he built. Our conversation explores the art of giving money away strategically: from supporting veterans and military families to investing in cybersecurity and protecting democracy. We also get personal - talking favorite TV shows, the pros and cons of AI, and the big question: how much is enough? Listen now.