Explore every episode of the podcast Is This Working?!

You think you’ve known Katie Couric your whole life. You have no idea. Yes, the press called her America's Sweetheart. They also called her a diva, an ice queen, and a bitch on wheels (Connor's favorite). The real story starts there: how does a journalist turned national icon become herself without losing the magic that got her there in the first place?   Connor and Katie’s conversation went everywhere: fame and what it does to your head, loss and what actually lasts, getting older, the Sarah Palin interview she still feels "secondhand cringe" about, pickleball, breast milk, how she got completely fooled by AI, and her glorious give-no-fucks era. Katie fills out a report card for Connor at the end too. You'll want to stay for that. CHAPTERS Chapters 00:00:00 How fame f*cks with your head 00:02:51 What most interviewers mess up 00:06:27 The power of boredom and the hippocampus 00:08:05 Addicted to the grind 00:12:18 Going independent before the creator economy existed 00:15:42 The perky problem and clapbacks on Threads 00:18:09 Fighting to be taken seriously 00:27:17 Sarah Palin and the interview heard around the world 00:33:20 AI, income inequality, and the Jevons paradox 00:37:59 Your colon saved a lot of lives 00:41:40 Faith, God, and being a secular humanist 00:45:12 We're all terminal, how do you want to spend your time? 00:47:55 Nothing matters but your friends and your family 00:49:38 The Katie Couric report card

When the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening. Ann Miura-Ko spent the last two decades deciding which founders are worth betting on. She wrote the first check into TaskRabbit, got in early on Lyft, and teaches entrepreneurship at Stanford. There are few people closer to what's actually happening in AI, and her read is a hopeful one: AI is coming for the order takers, but anyone can become an order maker. The order takers, the people whose job is to run down a list and check the boxes, should be nervous. But everyone is opinionated about something — the thing they insist gets done a certain way. Ann's argument is that this is now the whole job: point your expertise at an infinite number of software agents and let them handle the rest. Connor and Ann get into why you can't train AI to have soul, the difference between what AI lets you do and what you should choose *not* to do, and the "Ann brain" she's built so the technology works for her without her ever handing over the keys. The conversation is also, fittingly, a deeply human one: her childhood theory of what it means to be rich, and what it feels like to watch your kids leave home, one by one. CHAPTERS Chapters 00:00:00 Intro — Training AI to have soul 00:01:29 Sneaking into negotiations class 00:04:23 Is that a world-class effort? — Lessons from a rocket scientist dad 00:06:39 The PhD moment — Realizing you're not the best 00:07:58 Designing your life around self-expression 00:09:23 Starting Floodgate — Pregnant, PhD-ing, and investing 00:10:54 From young whippersnapper to wise boomer 00:12:25 Measuring success beyond work metrics 00:18:42 The pink and blue sweater — What it means to be rich 00:21:36 Develop the muscle for giving 00:22:46 Being asked to be a co-conspirator 00:25:05 Why are you in such a hurry? — The Stanford dropout trap 00:27:16 Building a personal AI brain 00:30:43 What's mine, what's yours? — The future of AI and IP 00:32:25 The five levels of AI adoption 00:33:16 You can't train AI to have soul 00:44:18 Order makers vs order takers 00:46:45 Religion, service, and who you're accountable to 00:53:15 Freedom from constraint — Marriage, religion, and the good life 00:54:27 Turning 50 — Shedding and what comes next

Kristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice, which is precisely why she got into the field. Berman was on the founding team for behavioral economics at Google — a practice that now spans 26 teams across the company — and she founded Irrational Labs, a behavioral product design company that helps companies like LinkedIn, Airbnb, and PayPal increase the health, wealth, and happiness of their users. Her work keeps landing on the same uncomfortable truth: the things that actually run your behavior are your environment and your incentives, and you barely notice either one. She learned the incentive half the hard way, when a project quietly turned her into what she calls a predatory lender.  In this episode, she and Connor get practical: Why buying a dog beats relying on willpower. How a “Ulysses contract” binds your future self. Why she built her life around a 20-person Oakland commune called Radish, where everyone eats dinner together at 7:30.  If you've ever known better and done it anyway, or wanted to know how to design an environment that brings out the best in your team, this one’s for you. CHAPTERS Chapters 00:00:00 The chocolate croissant you didn't mean to eat 00:00:55 Why behavioral science lights her up 00:02:16 How choice architecture works 00:05:31 You're always being manipulated by your environment 00:07:08 When good intentions meet bad incentives 00:08:39 The stand-up challenge — Closing the intention-action gap 00:09:53 Buy a dog — The power of one-time decisions 00:15:33 Commitment contracts that actually work 00:17:13 Taking away the joy of work — What leaders get wrong 00:19:51 Small teams, big autonomy — The Irrational Labs approach 00:21:35 Extrinsic vs intrinsic motivation — What actually works 00:26:26 Does confetti actually work? 00:27:30 Work harder — The contrarian take on workplace culture 00:29:04 Difficulty as fuel — The hero's journey at work 00:31:18 Social desirability — Why we're all a little vain 00:32:56 You've never arrived — The learning mindset 00:34:02 Living in a commune — Behavioral science in the wild 00:35:02 Behavioral contagion and seeing your partner perform 00:36:57 Relationships drive happiness — Make them easier 00:37:55 Low willpower, high design — How Kristen lives 00:39:40 The billboard — Compliment someone

Christina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year company. "We joke at Farmgirl that we're like cockroaches. You can't get rid of us. You just get stomped on, you just keep going." In this conversation, Christina and Connor talk about: the costs of building a company without the credentials the 28-hour test that saved the company during the pandemic why leaders can't always stick to their values why real leadership means feeling like crap most of the time If you're sick of leadership platitudes and hungry for the story of someone doing the hard work, against the odds, this conversation is for you.

Most people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula. Missy’s made a career being comfortable in contradictions like “following your passion is overrated”—and she’s got the resume to prove it.  After Yale, Boston Consulting Group, and TPG, Missy walked away from all of it to start a company making phone holders that kept babies entertained during diaper changes. She got a patent. The company failed. She'll tell you those were the best years of her career.  Now she's CEO of Crankstart Foundation. Crankstart's work is mostly about San Francisco: affordable housing, healthcare career ladders, the kind of cross-sector partnerships Missy says the philanthropy field doesn't do enough of. One recent project put $10 million into a 168-unit affordable housing building. Another is a UCSF partnership that builds a career ladder from medical assistant to radiologist. On this episode of Is This Working?!, she tells Connor about the eight years she spent at blue-chip firms specifically to earn herself the option to fail later. About what it took to look herself in the mirror and admit she wasn't good at being an entrepreneur. About why the best career advice she has for a 22-year-old is take a hard job, learn something hard, and trust you'll find what calls your heart later. And then she tells him about her mom, who died when Missy was 19 and her mom was 46. "I thought she had lived a lot," Missy says. "But now that I'm 44, I realize she was just getting started." CHAPTERS Chapters 00:00:00 Being okay with being wrong 00:00:57 McDonald's University and the hardest job ever 00:01:54 Parental expectations and the privilege of freedom 00:03:18 The competitive child 00:04:29 Performance through play — High achievement without pressure 00:07:19 The credibility sprint — Building a bank of signals 00:09:09 Don't follow your passion — Do this instead 00:14:55 The failed entrepreneur who never had more fun 00:21:01 Parenthood as a superpower in the workplace 00:24:30 From bloodthirsty capitalist to foundation leader 00:30:52 Working with Michael Moritz — Excellence teaches excellence 00:34:18 Making philanthropy less transactional 00:42:22 The trust battery and rising tides lift all boats 00:43:54 San Francisco needs grace, patience, and capital 00:45:29 Losing her mom at 19 — Nobody's entitled to tomorrow

AI is here. The layoffs have started. Does anyone have a plan? Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shepherded the CHIPS Act through Congress and personally negotiated chip exports with Chinese leadership. Harvard, Oxford, Yale Law before any of it. Her plan: a new grand bargain between government and business. Workforce training that's continuous, employer-led, and funded by outcomes. Wage insurance for workers retraining mid-career. Tax incentives that make it more expensive to abandon workers than to retrain them. The same urgency we've poured into chips and models, applied to the tens of millions of American jobs about to change. In this episode, Connor and Gina get into the plan, the warning ("do this wrong and we will have automated our decline"), why UBI is a cop-out, and her honest reply to whether she'd like the job of President in 2028. There's also a phrase she banned in her own cabinet that we can't in good conscience print here. Connor gets her to use it on camera. Stay for that. Chapters 00:00:00 Intro — The woman betting on America's AI future 00:01:16 Finding your Andy — Love, partnership, and non-negotiables 00:05:46 Faith, spirituality, and the work arena 00:08:01 The AI crisis nobody's preparing for 00:10:33 Winning AI without losing America 00:14:34 The grand bargain — Changing incentives for companies 00:17:55 More women in charge would help 00:20:16 The girl in the back seat with the racing stripe 00:22:39 Lightning round — Biden, bathrooms, and power perks 00:30:11 Grin-fucking and the yes-man problem 00:37:32 Presidential ambitions and the right moment 00:41:48 Conquering the self and the Msgina Special 00:48:03 Legacy, love, and what really 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!

Is there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, until the gap closed enough to jump. And the magic wasn't the only thing he was keeping hidden. David buried his mental health struggles for decades. When he finally started talking about it, he did the same thing. Told one therapist. Then 20 people. Then 50. Then 100. He calls it "opening the aperture of fear slowly." It became his approach for everything. Not one dramatic leap. Just a longer, quieter path toward his authentic self.  Now, he’s directed the #1 rated show in Las Vegas, has consulted for America's Got Talent for four seasons, performs 100+ nights a year for companies like Google, coaches executives on presence, and runs men's groups. He talks about switching from “gasoline” to “solar” as a fuel source, choosing 1,000 real relationships over hundreds of thousands of followers, and why the secrets you keep are the ones that cost you the most. He also reads Connor's mind at the end. Just stay for that part. Chapters 00:00:00 Intro — Magic as armor, authenticity as freedom 00:01:26 From external validation to internal fuel 00:04:00 The 12-year runway — Marketing by day, magic by night 00:06:34 Breaking the container — The Dunkin' moment 00:07:43 Creating awe for a living — The magician's mindset 00:08:52 Relationships over reach — Building a career without fame 00:10:13 Fear as a compass — Micro-dosing on authenticity 00:12:56 Magic became armor — Pennsylvania in the early 90s 00:15:24 Practice enables presence — The subconscious mind 00:16:06 TGIF at Google — The American Idol of leadership 00:18:30 Red, yellow, green — The simplest coaching tool 00:23:09 The spiritual practice — Meditation and men's work 00:31:18 The career transition — From stage to facilitation 00:34:55 Magical moments keep coming — The Tetris game of life 00:48:56 Assumptions and repositioning — The magician as marketer 00:45:42 Feedback as fuel — Taking notes from people you want to become 00:54:24 Borrowing confidence — Faith from others when you don't have it 00:56:16 Resources for the journey — Books and practices that matter 00:58:08 The magic trick — A coincidence you won't believe 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!

84 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E. In this episode, Patti gives a masterclass in crisis leadership — and pulls back the curtain on how she turned things around. She explains how she rebuilt the leadership team from scratch, why she hung up on every executive candidate who called PG&E a "stepping stone," and what it actually looks like to double down on safety and love (yes, love) when your company has killed 84 people. Five years later, PG&E has hit a 946-day safety record, buried 1,000 miles of power lines (a huge deal), and hasn't lost a single structure to equipment fire in 3 years. If you've ever inherited a mess, led a team through something nobody trained you for, or wondered whether the hard path is actually worth taking, this episode is for you. Chapters 00:00:00 Intro — Taking the hardest CEO job in America 00:01:40 From TV broadcaster dreams to utility CEO 00:02:55 Why leave a dream job for a nightmare? 00:08:10 The turnaround playbook — Purpose, lean, and breakthrough thinking 00:10:21 Hiring for service, not stepping stones 00:24:04 The Dixie fire — Six months in and everything's burning 00:30:07 Leading through crisis — Speak up, show up, go to the problem 00:17:32 When a coworker dies every 90 days — The safety transformation 00:36:05 Holding the weight — Grief, resolve, and progress 00:39:41 Ikigai and meaningful work — When your job fuels your life 00:47:48 Wrap-up — You're putting a man on the moon

Matt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast have earned over 80 million views and listens. And the first thing he told us is that the instinct to get it perfect is the exact thing making us worse. Not just at presentations. At everything. Meetings, hard conversations, even arguments with your partner about toothpaste. (He'll explain that one.) This is also a special episode: Connor is joined by his co-founder and co-CEO of Merit America, Rebecca Taber Staehelin. Matt coaches them both live through a high-stakes all-hands that almost went sideways and feedback that made Rebecca rethink how she'd been communicating for years. They also get into what to do when your mind goes completely blank in front of your team, a trick that kills fights with your partner before they start, and why most of the time we think someone didn't listen to us — the real problem is we never checked if they understood. Check out Matt’s podcast and books here: https://www.fastersmarter.io/. Chapters 00:00:00 Intro — Be interested, not interesting 00:07:17 Polished vs. authentic 00:09:59 Being spontaneous is a skill you can practice 00:12:22 Martial arts, breathing, and being present 00:14:40 Repetition, reflection, and feedback — The only way to improve 00:18:06 The toothpaste fight and the zero-to-ten scale 00:23:55 Managing high-stakes anxiety 00:29:30 Why mistakes make you human 00:36:15 Don't assume they'll connect the dots 00:37:57 Wrap-up — Think faster, talk smarter

"Are you breathing?" Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha moves through the world. Jin Ha is a Korean American actor currently playing Aaron Burr in Hamilton on Broadway. He's also starred in Apple TV's Pachinko, worked opposite Steve Martin and Martin Short in Only Murders in the Building, with Nick Offerman on Devs, originated a role in one of Stephen Sondheim's final musicals, just wrapped season two of Apple TV's Sugar alongside Colin Farrell, and opens next in the Broadway revival of Proof this spring.  Before all of that, he was at Columbia talking himself out of a banking career after his mom gently asked if he actually wanted to work at a bank. Smart mom. This conversation is packed with ideas that have nothing to do with acting and everything to do with how we work. Jin Ha breaks down why imposter syndrome hits your best people hardest (and what to do about it), shares the "instant expert" mindset his teacher used to unlock fearlessness in impossible situations, and tells a Nick Offerman story that quietly redefines what real leadership looks like. Connor and Jin also go somewhere most work podcasts won't: mortality, ego, and what happens when you stop performing your identity and just show up. Funny, grounded, and full of things you can actually use on Monday morning.

"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!

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

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!

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!

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!