Jonathan Block
Stumbling Blocks: How Great Leaders Are Made
Here, leaders share the moments along the way that have shaped them most deeply. Their stumbling blocks. You'll hear leaders as they really are: challenged, battered, and deeply flawed. And you'll see them picking back up, dusting themselves off, and leading again. Because if we let them, stumbling blocks make us better. Welcome to Stumbling Blocks: How Great Leaders are Made. I’m your host, Jonathan Block. I've spent the last 20 years studying leadership, and I ask leaders to take us back to the moments that aren't on highlight reel: • The day they got laid off. • The crisis that almost broke...
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Episodes
Kelli Arena, CEO, Nat'l Cryptologic Foundation: How I Helped NSA Find Its Voice 29.06.2026 57:15
Kelli Arena spent her career at CNN telling the public what powerful people would rather keep quiet. She covered the Justice Department, won an Emmy, and reported the Moussaoui trial, the only 9/11 case tried in an American civilian courtroom. After Kelli left journalism, she went into another form of public service, serving as Chief of Communications for the National Security Agency, spending eig...
Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide 29.05.2026 18:02
Shalene Gupta, staff editor for Fast Company's Work Life and Leadership section, interviewed 35 middle managers at some of the biggest companies in the world for her piece "The Middle Manager's AI Survival Guide." What she found is that the contradictory headlines about AI at work aren't actually contradictory. There are two different worlds, and which one you're working in makes a world of differ...
Dana Perino, White House Press Sec. & Bestselling Author: "Purple State" & Crossing Party Lines 06.05.2026 25:53
Dana Perino's new book is called Purple State. It's a political romance novel set in a gerrymandered Wisconsin district, about three young women who discover that love and friendship don't stop at party lines. Coming from the 26th White House Press Secretary and co-host of The Five on Fox News (the most-watched show on cable news!), it's a book worth paying attention to. Especially as we find ours...
Outtakes: Sue Gordon Meets My Parents 23.04.2026 4:47
My parents were visiting me the day I interviewed Sue Gordon, former Deputy Director of National Intelligence. So they joined me in the Treehouse Studio to say a quick hello to her. Here's their conversation.
Sue Gordon, Deputy Director of US Intelligence: What America Needs From Its Leaders 22.04.2026 1:36:54
Sue Gordon once oversaw 100,000 women and men of the U.S. intelligence community as Deputy Director of National Intelligence, the number two role in American spycraft. She briefed Presidents Reagan, HW Bush, Clinton, W Bush, Obama, and Trump. She managed a $100 billion budget. And in August 2019, she handed Vice President Pence her resignation letter with a handwritten note: "I offer this letter a...
Outtakes: The President's Advice I Didn't Want 22.04.2026 4:02
A few times during my two-part interview with Judge and Rebecca Gonzales, they turned the tables on me. They listened. And they drew three stories out of me that I've rarely shared. The first is a story that never made it into the main episodes: the Oval Office advice I didn't want that... changed my life. The second is about what happens when your Quaker mother and your Jewish father sit down tog...
Attorney General & Rebecca Gonzales, Pt 2: Leadership, Loss, and Love 28.03.2026 52:08
Part 2 of this exclusive conversation with Attorney General Alberto Gonzales and his wife Rebecca. It is a conversation about love, political betrayal, faith, and what it means to keep going when the wilderness feels endless. Judge Gonzales describes the political firestorm that ended his time as the nation's top law enforcement officer. What followed were years Rebecca calls "the wilderness." The...
Outtakes: AG Gonzales on ICE ("unprecedented, dangerous") & Epstein ("A complete failure of DOJ") 27.03.2026 8:36
Excerpts from Attorney General Gonzales and Rebecca Gonzales's interview with Stumbling Blocks on ICE Actions, Immigration, and the Epstein Files Excerpted Quotes from Attorney General Gonzales On ICE Actions and Immigration Based on what I've observed… it seems like we're going through an unprecedented, dangerous time. I worry about what's going on in our country, and I think a lot of Americans a...
Attorney General & Rebecca Gonzales, Pt 1: 9/11, Leading The War On Terror, & Going Broke 26.03.2026 1:10:04
EXCLUSIVE: This is a story two decades in the making. For the first time since leaving office 19 years ago, Attorney General Alberto Gonzales and his wife Rebecca Gonzales sat down together for an interview. In Part 1, the Attorney General and Rebecca speak candidly about ICE, immigration, and the Justice Department's handling of the Epstein files. They talk about Al's rise from a two-bedroom hous...
Conor Grennan, CEO, AI Mindset: Why AI is a Change Management Problem 10.03.2026 51:25
Conor Grennan is CEO of AI Mindset and until recently, Chief AI Architect at NYU Stern School of Business. He's trained teams at Google, NASA, Microsoft, JP Morgan, and many more. He's a New York Times bestselling author, a MasterClass Instructor, co-host of the AI Applied podcast, and a recipient of the Dalai Lama's Unsung Hero of Compassion Award. Conor has become one of the most sought-after sp...
Admiral Tim Ziemer, Chief, President's Malaria Initiative: How (and Why) I Saved 12 Million Lives 19.02.2026 49:27
In this episode, I welcome Rear Admiral Tim Ziemer, the former chief of the President’s Malaria Initiative (PMI) and former CEO of World Relief. Admiral Ziemer explains how and why he saved 12 million people from death by malaria, and prevented another 2 billion cases of the disease. He reflects on a life of disciplined service bookended by tragedy, from the 1968 attack in Vietnam that killed his...
Steve Scherer, Bureau Chief, Reuters Canada: From Interviewing the Prime Minister to Driving an Uber 12.02.2026 46:27
A conversation with former Reuters Canada Bureau Chief Steve Scherer on job displacement, the gig economy, and America’s identity crisis. Steve was once a high-level journalist, a Reuters Bureau Chief for Canada, who interviewed world leaders like Justin Trudeau and covered global financial markets. Then, a budget cut cost him his job, his work visa, and forced him to move his family out of Canada...
Brent Beshore, CEO, Permanent Equity: How Winning Made me Lose 05.02.2026 1:09:27
Brent Beshore made his first million at 28. Visited the White House. Got ranked 28th on the Inc. 500. Got everything he wanted. And realized he had summited the wrong mountain. In this raw conversation, Brent—CEO of Permanent Equity, a private equity firm that owns 16 companies generating $400M in revenue with zero debt—goes places most CEOs do not. He talks about weighing 252 pounds while everyth...
Linda Rutherford, CAO, Southwest Airlines: How a Proxy Fight Led to Assigned Seating (Pt 2) 29.01.2026 31:46
In this episode, I sit down with Linda Rutherford , former Chief Administration Officer of Southwest Airlines for the second half of our conversation. Linda, described as the "keeper of Southwest's corporate soul," provides a rare, behind-the-scenes look at how one of the world’s most iconic brands survived two of the most disruptive forces in its 50-year history: Winter Storm Elliott and the host...
Linda Rutherford, CAO, Southwest Airlines: What Made Southwest So Successful? 23.01.2026 46:21
In this episode, Linda Rutherford, the former Chief Administration Officer at Southwest Airlines, shares insights into the secret sauce that makes Southwest the 'LUV airline.' She discusses the legacy left by the airline's founding CEO, Herb Kelleher, and president, Colleen Barrett, as well as her role as a growth catalyst for the airline. Linda also reflects on her early life, resilience, and the...
Oscar Munoz, CEO, United: How I Broke a 5 Year Union Stalemate and Why I Hired my Successor (Pt 2) 15.01.2026 34:07
When Oscar Munoz stepped in as CEO of United Airlines, he didn't head for the executive suite. He headed for a Houston hangar at 2:00 AM to jump on a picnic table and listen to 500 angry aircraft mechanics. In part two of this deep-dive conversation, Oscar reveals why he threw out the "business school rule book" to save an airline with a broken spirit. We discuss: The Power of the Listening Tour:...
Oscar Munoz, CEO, United Airlines: Why It's Never too Late to do the Right Thing (Pt 1) 08.01.2026 42:07
The viral video that changed aviation—and the CEO who broke the rules to fix it. On April 9, 2017, United Airlines faced the world’s first truly global viral crisis when a passenger, Dr. David Dao, was forcibly dragged off a flight in Chicago. The internet exploded, calls for resignation mounted, and the airline’s initial response—calling the incident a "re-accommodation"—only poured gas on the fi...
Doug Conant, CEO, Campbell's: How I Transformed Campbell's Culture 18.12.2025 36:07
If your team is disengaged, cynical, or burnt out—Doug Conant has been there before. As CEO of Campbell's Soup, he inherited a culture that consultants called "Swamp Water." But by putting honoring people at the center of his leadership dashboard, Doug turned the company around, both in terms of employee engagement and also in terms of financial performance. In this episode, the former CEO of Camp...
Pete Proimos, CEO, AP Emissions: Why I Decided to Share my Diagnosis (Pt 2) 12.12.2025 31:21
Pete shares why he decided to tell the world his secret, what he did after finding what broke his heart, and what he'll do with the rest of his life after selling his company, AP Emissions Technology, to Berkshire Hathaway. He discusses how the Filotimo Foundation serves people with Cystic Fibrosis, what he would say to his 19 year old self, and giving back more than the disease will take Links: D...
Pete Proimos, CEO, AP Emissions: Find the Thing that Breaks your Heart and Never Look Away (Pt 1) 11.12.2025 27:42
Pete shares his remarkable journey from being diagnosed with cystic fibrosis, to hiding the disease as a CEO, to selling to Warren Buffett, to finding what broke his heart and refusing to look away. He discusses his family's immigration story, the evolution of their business, the challenges he faced growing up with a chronic illness, and the time his mom threatened to break a social worker's legs....
Sandra Sucher, Harvard Business School: How to Apologize 04.12.2025 42:05
In this conversation, Sandra Sucher, a professor at Harvard Business School and expert on trust, shares her unique journey from growing up in Detroit to teaching at Harvard. She discusses the importance of apologies in repairing trust, the nuances of moral leadership, and the challenges of navigating career paths. Through personal anecdotes and research-driven insights, Sandra emphasizes the signi...
Mark Farkas, Executive Producer, CSPAN: What I learned in the East Wing 19.11.2025 27:30
We’ve all seen the White House from the outside. But what's it really like on the inside? Especially the East Wing? Mark Farkas knows. As the producer of the first-ever HD documentary on the White House, he spent 9 months filming in rooms most people will never see. The "stumbling block" was navigating the immense security and hidden protocols of the most secure building on Earth. Mark gives us an...
Admiral Mark Harnitchek, Director of DoD Logistics: How I Solved the Puzzle of Pakistan 14.11.2025 1:25:57
What does it take to lead when the stumbling block is a Category 5 hurricane, a massive earthquake, or two global wars? Welcome to a masterclass in crisis leadership. Vice Admiral Mark Harnitchek (Retired) is one of the few people on Earth who truly knows. He served on nuclear-armed submarines, commanded the $46 billion Defense Logistics Agency, and was the military's "boots on the ground" leader...
Charles Green, CEO, Trusted Advisor | Creator, Trust Equation: Selfishness is the Ultimate Stumble 30.10.2025 31:11
What's the one thing that will destroy a team, a company, or a career faster than anything else? According to Charlie Green, creator of the Trust Equation, the answer is simple: self-orientation . It’s the single biggest "stumbling block" to effective leadership. In this episode, Charlie joins Jonathan to dismantle the idea that "if you can't measure it, you can't manage it." He makes a powerful c...
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