Stumbling Blocks: How Great Leaders Are Made

Jonathan Block
  • 5.0 (23)
  • MANAGEMENT

Here, leaders share their stumbling blocks, what they learned through the stumble, and how it changed them. 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 our stumbling blocks make us better, if we let them. Welcome to Stumbling Blocks: How Great Leaders are Made. I’m Jonathan Block. I ask leaders to take us back to the moments that don't make it to highlight reel: • The day they got laid off. • The crisis that almost broke them. • The loss that re-shaped how they see the world. Join me to uncover the fires that forge great leaders. This leadership podcast is what gritty, authentic leadership looks like. No AI slop. Episodes drop every Thursday. Subscribe today. Welcome to The Stumble. Questions? Comments? Linkedin: www.linkedin.com/in/jonathanfblock Insta: @JonathanFBlock Twitter: @JonathanFBlock Email: Jonathan@BlockLeadershipGroup.com

  1. Attorney General & Rebecca Gonzales, Pt 2: The Wilderness, Disappearing Friends, & Finding "Home"

    MAR 28

    Attorney General & Rebecca Gonzales, Pt 2: The Wilderness, Disappearing Friends, & Finding "Home"

    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 phone stopped ringing. Friends vanished. Job opportunities disappeared. And the pain was so deep they sat side by side in silence, because words wouldn't come. But strangers showed up in ways you won't expect. And President Bush wrote a handwritten note that says something every leader needs to hear. And eventually, it becomes clear where home is. It's a political love story unlike any you've heard before. If you missed Part 1, start there first: https://podcasts.apple.com/us/podcast/exclusive-attorney-general-alberto-gonzales-becky-gonzales/id1849573843?i=1000757588087 Next episode: Sue Gordon, 30-year CIA veteran and former Deputy Director of National Intelligence. 0:00:00 Introduction & Part 1 Recap 0:03:30 The U.S. Attorney Scandal 0:07:45 "People Will Do Anything to Get Power" 0:09:50 President Bush Defends His Attorney General 0:11:45 The Call to Resign 0:15:30 The Phone Stopped Ringing 0:18:00 "We're Rich in Love" 0:22:15 President Bush's Handwritten Letter 0:27:30 The Wilderness Years 0:34:15 "It's Got to Work Out" 0:40:50 Finding Home in Nashville 0:45:35 Advice for Your Own Wilderness 0:51:00 Outro & Next Episode Preview TAGS/KEYWORDS: leadership, resilience, Attorney General, Alberto Gonzales, George W. Bush, public service, marriage, faith, political crisis, Washington DC, wilderness, Belmont University, trust, Rebecca Gonzales

    52 min
  2. Gonzales Excerpts: ICE, Immigration, & The Epstein Files

    MAR 27 ·  BONUS

    Gonzales Excerpts: ICE, Immigration, & The Epstein Files

    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 are worried about it. The way that we're enforcing immigration today, to me, it sends a terrible message, not just to the American people. It sends a terrible message to people around the world, in terms of what America is today, as opposed to…talking about the value of immigrants and how much they've contributed and why we as a country are stronger and better because we have welcomed immigrants and they're part of the fabric of our society. I don't think that message is out there anymore, and I think that really does sadden me. I think that makes America weaker. I really do. And I think it emboldens our enemies. Hopefully the courts and hopefully Congress will take action and address it. ___________________________ Excerpted Quotes from Attorney General Gonzales On the Epstein Files I think this whole episode is embarrassing. I think it's an embarrassment to this Administration, to the Department of Justice, a complete failure of the Department to abide by the law. That's the role of the Department of Justice — to enforce the law. And here we have a Department that's not doing that. But what appears to be, in some cases, selective redactions and the selective release of documents, drip, drip, drip process, it sends a terrible message. And I think it's legitimate for the American people to wonder, “what are you hiding?” It hurts the image of America, I think, around the world. The way that this has been handled from the very beginning has been a disaster. For the American people, certainly for this Administration, and for the victims.

    9 min
  3. Attorney General & Rebecca Gonzales, Pt 1: Love, 9/11, & Going Broke

    MAR 26

    Attorney General & Rebecca Gonzales, Pt 1: Love, 9/11, & Going Broke

    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 house in Humble, Texas to the Oval Office, why he chose to make protecting kids from online predators a federal priority even during the global war on terror, and what it was like for Rebecca to navigate 9/11 alone with their boys while Al was at the White House. Underneath the headlines is a story about faith and love and what happens when the President calls and your comfortable life disappears. Part 2 drops next week. CHAPTERS: 00:00 - Introduction 02:00 - Belmont University and Rebecca's path to social work 04:51 - On ICE and immigration 08:07 - The Epstein files: a failure by the Justice Department 13:38 - Rebecca's upbringing: Jewish mother, Mormon father 19:06 - Judge Gonzales' origins: son of migrant workers in Houston 22:53 - How Al and Rebecca met (and the Four Seasons bachelor pad) 25:27 - Governor Bush calls: leaving private practice behind 34:21 - Why he still prefers to be called "Judge" 35:45 - Moving to Washington with President Bush 38:57 - Rebecca alone: December 26 to June 42:36 - September 11th: Rebecca's story 44:50 - September 11th: The Judge on the Oval Office porch 52:58 - How 9/11 changed their faith and their family 56:46 - "Put your uniform on": becoming Attorney General 1:00:01 - Financial sacrifice and raising a family under pressure 1:04:31 - Project Safe Childhood: why he fought for kids 1:07:21 - A personal note from your host 1:12:07 - What's coming in Part 2 LINKS: Judge Gonzales' book, "True Faith and Allegiance: A Story of Service and Sacrifice in War and Peace": https://www.amazon.com/True-Faith-Allegiance-Service-Sacrifice/dp/071807887X Project Safe Childhood (U.S. Department of Justice): https://www.justice.gov/psc TAGS/KEYWORDS: leadership, Alberto Gonzales, attorney general, 9/11, Bush administration, immigration, faith, family, White House, Department of Justice, Project Safe Childhood, Epstein files, public service, resilience, Rebecca Gonzales

    1h 10m
  4. Conor Grennan, CEO, AI Mindset: Why AI is a Change Management Problem + Grabbing Coattails

    MAR 10

    Conor Grennan, CEO, AI Mindset: Why AI is a Change Management Problem + Grabbing Coattails

    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 speakers and strategists in the AI space. But what's most interesting are the reinventions that brought Conor to AI: moving to Prague at 21 to avoid being ordinary, volunteering in a Nepali orphanage, going back when the children he cared for were re-trafficked, and writing a fantasy novel. We dig into Conor's contrarian take that AI is fundamentally a Change Management issue, not a tech issue. We also cover his best public speaking advice, what he would say with one final tweet, and the one simple thing any leader can do today to start using AI: "Just tell it." TIMESTAMPS: (04:33) Why honest reason Conor kept putting himself in interesting positions (06:23) Moving to Prague at 21 (07:49) Going to Nepal for a pickup line (09:46) Why he went back (12:49) Seeing a need and filling it (13:30) Meeting the Dalai Lama (15:29) How "The Art of Happiness" changed everything — and why he was happiest with nothing (18:57) Coming back to America and what he couldn't bring with him (21:28) How Nepal changed his parenting (23:48) Writing fiction: The Hadley Academy and the introvert revelation (27:51) How NYU Stern's Dean of Students role found him (31:59) Public speaking: why making a small mistake might be the key to winning the audience (37:46) The AI framework that flipped everything (43:24) AI is like electricity, not a light bulb (46:42) AI: just tell it (48:16) One tweet left: "You don't have to do what everybody else does" (50:07) Jonathan's outro — what Conor's story means for leaders navigating reinvention, and a preview of the Attorney General Gonzales episode LINKS: Conor's company — AI Mindset: https://www.ai-mindset.ai/ Conor's podcast — AI Applied (with Jaeden Schafer): https://podcasts.apple.com/us/podcast/ai-applied-covering-ai-news-interviews-and-tools/id1669799110 Conor's book — Little Princes: One Man's Promise to Bring Home the Lost Children of Nepal: https://a.co/d/00sGdmLP Conor's book — The Hadley Academy for the Improbably Gifted: https://a.co/d/05icO15V ABOUT: Jonathan Block is a leadership development and change management advisor who has helped hundreds of Fortune 500 leaders navigate C-suite succession, AI adoption, M&A, and organizational transformation. He launched and led PricewaterhouseCoopers' Trust Leadership Institute, reaching 14,000 Fortune 500 executives over 3 years, and driving $2 billion in influenced wins for PwC. He recently founded Block Leadership Group and hosts this podcast to quench his insatiable curiosity about the moments that change great leaders. More: www.blockleadershipgroup.com

    51 min
  5. Admiral Tim Ziemer, Chief, President's Malaria Initiative: How (and Why) I Saved 12 Million Lives

    FEB 19

    Admiral Tim Ziemer, Chief, President's Malaria Initiative: How (and Why) I Saved 12 Million Lives

    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 father and left his mother with 18 grenade wounds, to the sudden loss of his wife of 54 years, Jodi. From Admiral Ziemer, you'll learn these 3 things: 1) The surprising note his mom gave him after she landed in an air ambulance at Andrews AFB 2) What it took for him to say "yes" to the call from the White House 3) How to design a life Chapters 00:00 – Introduction 03:40 – Understanding the scale of the world's deadliest disease. 08:31 – The "Decommissioning" of USAID 12:56 – The Drill Instructor’s "Black Book" 15:00 – A Childhood in a Leper Colony 19:19 – Processing the murder of his dad and the capture of his mom. 22:06 – A Note of Gratitude: The incredible moment on a medical transport plane. 26:52 – Returning to Vietnam 31:31 – "I Don’t Coordinate": Negotiating with the Bush White House for authority to get things done. 40:06 – "Go Save Lives": A direct briefing in the Oval Office 46:14 – Alone on Golden Pond: Navigating grief and finding purpose after the death of his wife. 47:31 – The Final Challenge: Design a life around faithfulness. Links: KFF Research  https://www.kff.org/global-health-policy/the-trump-administrations-foreign-aid-review-status-of-the-presidents-malaria-initiative-pmi/ CDC Website: PMI Celebrates 15 Years https://archive.cdc.gov/www_cdc_gov/globalhealth/stories/2020/celebrating-15-years.html NIH Report on PMI https://pmc.ncbi.nlm.nih.gov/articles/PMC8176495/ Wheaton Magazine: Hope in the Healer https://magazine.wheaton.edu/stories/hope-in-the-healer Remarks upon Receiving the Roger E Joseph Prize https://www.rogerejosephprize.org/2015 Jodi Ziemer Obituary https://vacremationsociety.com/obituary/gene-joanne-jodi-ziemer/ Admiral Tim Ziemer: Rallying the World to Defeat Malaria https://medium.com/@PMIgov/rallying-the-world-to-defeat-malaria-4c2b63f231e2 New York Times: The Malaria Fighter https://www.nytimes.com/2014/10/21/science/a-quiet-approach-to-bringing-down-malaria.html PHOTO BY GREG KAHN FOR THE NEW YORK TIMES

    49 min
  6. Steve Scherer, Bureau Chief, Reuters Canada: From Interviewing the Prime Minister to Driving an Uber

    FEB 12

    Steve Scherer, Bureau Chief, Reuters Canada: From Interviewing the Prime Minister to Driving an Uber

    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. Now, he’s driving for Uber to make ends meet. He chronicled his experience a viral Substack essay, "My Journey from Foreign Correspondent to Uber Driver in Trump's America." In this raw and honest conversation, Steven shares the story of his displacement and offers a powerful and humbling perspective on the economic anxieties, political divisions, and human needs that connect us all. Steve talks about what it is like to turn over the keys to a role that filled him with pride, gave him leverage, and provided a powerful platform... and slide into the driver's seat of an Uber. Timestamps [00:00] From Reuters Bureau Chief to Uber Driver: The viral essay and the shock of displacement.[02:54] How a high salary and a lost work permit forced Steven and his family to leave Canada.[09:41] The unexpected family move to Italy and why Steven's wife fears returning to "Trump's America."[12:30] The decision to drive for Uber: flexibility, low pay, and the surprising feeling of being "invisible."[16:25] Why returning to the U.S. after 28 years felt like coming home to a more divided country.[23:56] The roots of "politics as entertainment": covering Silvio Berlusconi[31:02] Steven's most moving story: Covering the deadliest migration route in the world from Libya to Italy and rescuing 530 people in a single day.[35:28] Connecting personal unemployment and loss of "leverage" to the desperation of migrants. See Steve's substack here: https://stevescherer.substack.com/p/my-journey-from-foreign-correspondent?utm_campaign=post-expanded-share&utm_medium=web&triedRedirect=true Steve's Twitter Feed: https://x.com/SchererSteve

    46 min

  7. FEB 5

    Brent Beshore, CEO, Permanent Equity: How Winning Made me Lose

    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 everything he ate tasted grey. About earning a million dollars but telling his wife he didn't love her. About being an ardent atheist who made fun of Christians before everything changed. This isn't your typical CEO interview. Brent breaks down why traditional private equity is broken, how his firm operates without debt or forced exits, and why treating people well isn't just nice—it actually delivers better returns. But the real lesson? "The lie is that money will make you someone else. The truth is that money only makes you more of what you already are." If you've ever felt like you're winning the wrong game, this conversation will hit hard. TIMESTAMPS: [01:27] What is Permanent Equity? [06:43] The two stakeholders traditional PE serves—and everyone it doesn't [08:04] The portfolio: 16 companies, $400M revenue, $50M free cash flow, zero debt [10:48] "We want to be a kind, generous, long-term owner" [20:24] 28 years old: First million, Inc. 500, White House advisor, and completely hollowed out [22:47] Climbing the wrong mountain [27:36] "I don't even know what love meant when we got married" [28:05] Why he never wanted kids (and why he wishes he had five more now) [29:32] "He who has the gold makes the rules" vs. "The meek shall inherit the earth" [32:23] "Do I own the things I create? No, of course not." [37:36] Living generously: Why they give away 25% before taxes [45:25] Good reasons to sell vs. bad reasons to sell [48:37] How long-term thinking changes everything—with investors, employees, and communities [50:55] The Main Street Summit: "You belong here. You're important. You matter." [53:38] Being known vs. being loved: The safeguard against blowing up your life [54:08] Addiction, affairs, and cutting corners: What happens when you're unknown [56:50] The "Brené Brown bullsh*t" review (his favorite) [58:06] The day everything changed: Dropping the performance and being authentic [1:03:49] We're all going to anonymity—so what really matters? [1:07:04] Advice for someone climbing the wrong mountain: You're not alone [1:09:09] "Study the greats—all the greats study Jesus" GUEST: Brent Beshore CEO, Permanent Equity Columbia, Missouri HOST: Jonathan Block Founder, Stumbling Blocks Podcast LINKS: https://www.permanentequity.com/ linkedin.com/in/brentbeshore https://www.mainstreetsummit.com/ If this conversation resonated, please pass it along.

    1h 9m
  8. Linda Rutherford, CAO, Southwest Airlines: How a Proxy Fight Led to Assigned Seating (Pt 2)

    JAN 29

    Linda Rutherford, CAO, Southwest Airlines: How a Proxy Fight Led to Assigned Seating (Pt 2)

    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 hostile takeover by Elliott Investment Management. The conversation explores the "Twin Elliotts"—the 2022 operational meltdown that stranded millions and cost the airline $1.2 billion; and the 2024 activist investor surge that forced a radical reinvention of the airline. From paying for a customer’s Craigslist car to the end of open seating, Linda discusses the high-stakes leadership required to maintain a company's heart while satisfying Wall Street's demands. Show Highlights & Timestamps[00:00] The First Storm: Winter Storm Elliott (2022) Linda recounts the unprecedented operational "brownout" during the 2022 holiday season. She explains how mismatched aircraft and crews led to 17,000 cancellations and a $1.2 billion recovery effort.[02:00] The Strategy Behind the Change Jonathan and Linda discuss the historic shift from open seating to assigned seating and the introduction of premium cabin options.[03:30] Keeping the Corporate Soul How do you maintain a "culture of love" (and the LUV ticker) through four CEO transitions? Linda explains her role in bridging the gap between founding legends Herb Kelleher and Colleen Barrett and the modern era.[13:26] The Vulnerability Playbook A deep dive into the "war room" during the meltdown. Linda discusses why Southwest chose radical transparency, including a public-facing checklist of operational fixes to earn back passenger trust.[17:38] The $1.2 Billion "Make-Good" The extraordinary measures taken to compensate 2 million displaced passengers, including refunding cruises and even a car purchased on Craigslist.[18:50] The Second Storm: Elliott Investment Management (2024) The arrival of activist investors. Linda details the "all-hands" internal response, the restructuring of the Board of Directors, and the pressure of a languishing stock price.[24:00] Going to School on Activism Linda describes the steep learning curve for the executive team as they engaged with activist demands for the first time in company history.[28:54] Leadership Advice: The Nitty-Gritty of Change Linda’s parting wisdom for leaders facing "disruptive reinvention": why a memo isn't enough and why psychological safety is the key to successful transformation.Key Takeaways for LeadersTrust is a Bank Account: Southwest’s Net Promoter Score (NPS) plummeted to single digits during the meltdown but stayed positive because of decades of "goodwill deposits." Reinvention vs. Transformation: Linda argues that Southwest isn't changing; it’s reinventing its business model to meet modern traveler expectations while protecting labor contracts. Change Management Matters: In a period of constant crisis, communication must move beyond "checking the box" to address the psychological needs and upskilling of the workforce. Questions? Guest Pitches? Shoot me an email at Jonathan@Blockleadershipgroup.com

    32 min
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5
out of 5
23 Ratings

About

Here, leaders share their stumbling blocks, what they learned through the stumble, and how it changed them. 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 our stumbling blocks make us better, if we let them. Welcome to Stumbling Blocks: How Great Leaders are Made. I’m Jonathan Block. I ask leaders to take us back to the moments that don't make it to highlight reel: • The day they got laid off. • The crisis that almost broke them. • The loss that re-shaped how they see the world. Join me to uncover the fires that forge great leaders. This leadership podcast is what gritty, authentic leadership looks like. No AI slop. Episodes drop every Thursday. Subscribe today. Welcome to The Stumble. Questions? Comments? Linkedin: www.linkedin.com/in/jonathanfblock Insta: @JonathanFBlock Twitter: @JonathanFBlock Email: Jonathan@BlockLeadershipGroup.com

Information

  • Creator
    Jonathan Block
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Explicit
  • Copyright
    © 2025 Jonathan Block

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