Is This Working?!

Connor Diemand-Yauman
  • 5.0 (14)
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What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there. Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.

Episodes

  1. We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramek

    6D AGO

    We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramek

    "Am I wasting some of the best years of my life?" Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever.  His plan: build an entirely new city on 100+ square miles of farmland in Solano County.  Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of homes in a state that's short 3 million of them. His friends thought he'd lost it. Investors wouldn't return his calls. His wife was the only person who believed in what he was doing. So he did something most founders wouldn't: he spent eight months trying to prove his own idea was wrong. He bought a 1958 government study off eBay, opened it up, and found a city planned for the exact same coordinates. Same location, to the mile. He bet everything he had. In this conversation, Jan and Connor get into what it actually feels like to build something this big when nobody believes in it yet. Jan talks about the difference between fascination and discipline, why knowing yourself matters more than knowing your market, and the moment the project almost broke him. They also cover unexpected ground: why house parties changed more minds than any ad campaign, and what competitive StarCraft taught him about getting things done. CHAPTERS Chapters 00:00:00 Building the next great American city 00:02:52 From Czech village to California visionary 00:04:11 The housing crisis nobody wants to solve 00:06:48 The leap from problem to solution 00:09:54 Proving it's not crazy — The 1958 validation 00:13:25 The inner skeptic and relentless optimism 00:21:17 Betting everything — The moment of no return 00:21:02 Silicon Valley's unique risk appetite 00:23:47 The overnight success that took ten years 00:32:53 Facing the backlash and building trust 00:47:28 House parties over TV ads — The unscalable solution 00:50:13 The big debate California needs to have 00:52:56 Starcraft and clicks per minute — The execution mindset 00:53:50 The future — Building begins IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!

    56 min
  2. AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi Kumar

    JAN 27

    AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi Kumar

    Ravi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code. He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone else. In this conversation, Ravi and Connor dig into what most AI conversations miss: why entry-level jobs might actually expand, not disappear. Why "problem finders" will matter more than problem solvers. And why the old model of education → work → retire is already broken and in desperate need of disruption. For anyone anxious about AI and the future of work, this is the conversation you didn't know you needed: a leader who sees what's coming and can actually explain where the opportunities are. Chapters 00:00:00 You're not competing with AI, you're competing with people using AI 00:01:27 From worst student to nuclear physicist to CEO 00:03:03 Leading through influence, not control 00:05:47 Betting on unconventional talent and upward mobility 00:08:25 Rethinking education — Learning, working, and earning together 00:11:18 AI as equalizer — The bottom gains more than the top 00:14:05 Jobs won't disappear — They'll multiply 00:15:58 The training crisis and velocity of change 00:18:27 Code generation and the agentic future 00:23:00 Amplify humans, don't replace them — A counter to Turing 00:31:21 Corporate responsibility and the Synapse Initiative 00:34:16 What keeps him up at night — Regulation, inequality, and the race 00:38:55 Corporations as platforms for societal change 00:40:41 Advice for the next generation — Master interdisciplinary thinking

    44 min
  3. You Can Change a Lot More Than You Think — Somatic Coach Harley Frank

    12/17/2025

    You Can Change a Lot More Than You Think — Somatic Coach Harley Frank

    How much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think. Once a startup executive living with chronic anxiety and depression, Frank now works with leaders around the world using somatic body-based practices to help them reclaim choice, vitality, and presence. In this conversation, Harley and Connor explore why many of the traits we think are “just who we are” in work and life are actually frozen patterns in the nervous system—and how practices like somatics, inner-child work, and embodied awareness can unlock real transformation.  This episode is about leadership, creativity, healing, and what becomes possible when we stop trying to think our way out of pain—and learn to feel our way through it. CHAPTERS Chapters 00:00:00 Intro — You can transform more than you think 00:03:47 From tech executive to somatic coach 00:12:10 What somatics actually is 00:14:59 Why shame runs the show 00:17:19 Inner child work and neural rewiring 00:24:45 Leadership is about embodiment 00:31:08 The first step — Building a daily practice 00:37:40 Feel your part, no more 00:43:05 Pain vs. suffering — The 90-second rule 00:51:53 Shame, technology, and staying present IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!

    1h 1m
  4. Want to Keep Fighting? Stay Optimistic — ACLU's Anthony Romero

    12/03/2025

    Want to Keep Fighting? Stay Optimistic — ACLU's Anthony Romero

    Anthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis. In this conversation, recorded inside ACLU headquarters in New York, Romero and Connor talk about what it means to do work that is forged in conflict while still protecting your humanity. Anthony shares how he stays centered amid tragedy and noise, why “slowing things down” can be a form of progress, and how small daily practices—kindness, discipline, honest self-reflection—are what keep him from burning out. We also zoom out: What does leadership look like when the stakes feel impossibly high? What happens when your work requires you to step into friction again and again? And what responsibility does our generation have for the systems—and the workplace cultures—we’re leaving behind? For anyone who cares about doing meaningful work without losing themselves in the process, this conversation offers a rare mix of realism, agency, and genuine optimism. CHAPTERS Chapters 00:00:00 Intro — Fighting for democracy in a constitutional crisis 00:02:57 Constitutional crisis or opportunity for resistance? 00:04:14 Leading through tragedy and staying centered 00:07:07 Winning by losing — ACLU's litigation strategy 00:10:43 Redefining success and bringing the public along 00:12:20 The but-for test — Would America be worse without the ACLU? 00:16:53 Best case, worst case — America's future scenarios 00:20:48 Looking at the map — Opportunities in every state 00:23:01 The last man standing — Embracing friction 00:27:01 This is a rental car — Legacy and succession 00:29:08 How my generation f*cked it up 00:32:49 Message to young leaders — Keep fighting, it matters IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!

    34 min
  5. Follow the Laughter, Find the Truth — Comedian Sarah Cooper

    11/12/2025

    Follow the Laughter, Find the Truth — Comedian Sarah Cooper

    Sarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live. But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed. In this conversation, Sarah and Connor go beneath the viral moment and explore how comedy became her way of moving through pain, divorce, and reinvention. They unpack how self-awareness fuels creativity, how intuition beats optimization, and how humor itself reveals the deeper work of resilience and self-leadership. CHAPTERS Chapters 00:00:00 Intro — Sarah Cooper on success, doubt, and meaning 00:01:13 From Google to comedy 00:04:36 Going viral & getting humbled 00:07:22 The hangover after fame 00:11:03 Perfectionism, family, and learning to fail 00:15:43 Rediscovering herself after divorce 00:18:10 Comedy as power & perspective 00:21:24 The human voice in an AI age 00:27:01 Fame, isolation, and honesty 00:32:04 Leaving Google and finding courage 00:38:59 Manifestation gone wrong (the SNL story) 00:45:00 Group therapy & saying what’s real 00:58:25 Legacy — making people feel less alone IS THIS WORKING?! What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!

    59 min
  • 5 Episodes

5
out of 5
14 Ratings

About

What if the most interesting thing about work isn’t what we do—but what it does to us? Is This Working?! dives into meaningful work and the messy humans who do it. As AI reshapes industries and upends old definitions of success, social entrepreneur and Stanford GSB lecturer Connor Diemand-Yauman talks with extraordinary people about both sides of the story: the outer work (what they built, how they pivoted, the tactics that actually worked) and the inner work(the therapy, the doubt, the failure) it took to get there. Because when the world is changing this fast, maybe these stories are the only way to know if any of this is actually working.

Information

  • Creator
    Connor Diemand-Yauman
  • Years Active
    2025 - 2026
  • Episodes
    5
  • Rating
    Clean

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