Podcast
Is This Working?!
Hosted by Connor Diemand-Yauman · EN
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.
12episodes
Episodes
Newest firstAll episodes
Why Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina Stembel
2w ago00:49:48Tap to summarizeChristina 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 credentialsthe 28-hour test that saved the company during the pandemicwhy leaders can't always stick to their valueswhy real leadership means feeling like crap most of the timeIf 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.
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Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy Narula
4w ago00:49:19Tap to summarizeMost 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."CHAPTERSChapters00:00:00 Being okay with being wrong00:00:57 McDonald's University and the hardest job ever00:01:54 Parental expectations and the privilege of freedom00:03:18 The competitive child00:04:29 Performance through play — High achievement without pressure00:07:19 The credibility sprint — Building a bank of signals00:09:09 Don't follow your passion — Do this instead00:14:55 The failed entrepreneur who never had more fun00:21:01 Parenthood as a superpower in the workplace00:24:30 From bloodthirsty capitalist to foundation leader00:30:52 Working with Michael Moritz — Excellence teaches excellence00:34:18 Making philanthropy less transactional00:42:22 The trust battery and rising tides lift all boats00:43:54 San Francisco needs grace, patience, and capital00:45:29 Losing her mom at 19 — Nobody's entitled to tomorrow
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Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondo
Apr 2900:49:43Tap to summarizeAI 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.Chapters00:00:00 Intro — The woman betting on America's AI future00:01:16 Finding your Andy — Love, partnership, and non-negotiables00:05:46 Faith, spirituality, and the work arena00:08:01 The AI crisis nobody's preparing for00:10:33 Winning AI without losing America00:14:34 The grand bargain — Changing incentives for companies00:17:55 More women in charge would help00:20:16 The girl in the back seat with the racing stripe00:22:39 Lightning round — Biden, bathrooms, and power perks00:30:11 Grin-fucking and the yes-man problem00:37:32 Presidential ambitions and the right moment00:41:48 Conquering the self and the Msgina Special00:48:03 Legacy, love, and what really mattersIS 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!
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The Slowest Career Change In History | Magician David Gerard
Apr 801:07:15Tap to summarizeIs 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.Chapters00:00:00 Intro — Magic as armor, authenticity as freedom00:01:26 From external validation to internal fuel00:04:00 The 12-year runway — Marketing by day, magic by night00:06:34 Breaking the container — The Dunkin' moment00:07:43 Creating awe for a living — The magician's mindset00:08:52 Relationships over reach — Building a career without fame00:10:13 Fear as a compass — Micro-dosing on authenticity00:12:56 Magic became armor — Pennsylvania in the early 90s00:15:24 Practice enables presence — The subconscious mind00:16:06 TGIF at Google — The American Idol of leadership00:18:30 Red, yellow, green — The simplest coaching tool00:23:09 The spiritual practice — Meditation and men's work00:31:18 The career transition — From stage to facilitation00:34:55 Magical moments keep coming — The Tetris game of life00:48:56 Assumptions and repositioning — The magician as marketer00:45:42 Feedback as fuel — Taking notes from people you want to become00:54:24 Borrowing confidence — Faith from others when you don't have it00:56:16 Resources for the journey — Books and practices that matter00:58:08 The magic trick — A coincidence you won't believeIS 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!
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Why She Took the Hardest CEO Job in America | PG&E's Patti Poppe
Mar 2500:47:57Tap to summarize84 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.Chapters00:00:00 Intro — Taking the hardest CEO job in America00:01:40 From TV broadcaster dreams to utility CEO00:02:55 Why leave a dream job for a nightmare?00:08:10 The turnaround playbook — Purpose, lean, and breakthrough thinking00:10:21 Hiring for service, not stepping stones00:24:04 The Dixie fire — Six months in and everything's burning00:30:07 Leading through crisis — Speak up, show up, go to the problem00:17:32 When a coworker dies every 90 days — The safety transformation00:36:05 Holding the weight — Grief, resolve, and progress00:39:41 Ikigai and meaningful work — When your job fuels your life00:47:48 Wrap-up — You're putting a man on the moon
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The Overachiever’s Guide To Effective Communication - Stanford's Matt Abrahams
Mar 1100:39:50Tap to summarizeMatt 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/. Chapters00:00:00 Intro — Be interested, not interesting00:07:17 Polished vs. authentic00:09:59 Being spontaneous is a skill you can practice00:12:22 Martial arts, breathing, and being present00:14:40 Repetition, reflection, and feedback — The only way to improve00:18:06 The toothpaste fight and the zero-to-ten scale00:23:55 Managing high-stakes anxiety00:29:30 Why mistakes make you human00:36:15 Don't assume they'll connect the dots00:37:57 Wrap-up — Think faster, talk smarter
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Jin Ha (Hamilton, Only Murders In The Building): Stop Performing and Start Breathing
Feb 2500:50:16Tap to summarize"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.
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We've Built Cities for 20,000 Years. Why Did We Stop? — California Forever's Jan Sramek
Feb 1100:56:00Tap to summarize"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.CHAPTERSChapters00:00:00 Building the next great American city00:02:52 From Czech village to California visionary00:04:11 The housing crisis nobody wants to solve00:06:48 The leap from problem to solution00:09:54 Proving it's not crazy — The 1958 validation00:13:25 The inner skeptic and relentless optimism00:21:17 Betting everything — The moment of no return00:21:02 Silicon Valley's unique risk appetite00:23:47 The overnight success that took ten years00:32:53 Facing the backlash and building trust00:47:28 House parties over TV ads — The unscalable solution00:50:13 The big debate California needs to have00:52:56 Starcraft and clicks per minute — The execution mindset00:53:50 The future — Building beginsIS 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!
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AI Won't Erase Jobs. Here’s Why — Cognizant CEO Ravi Kumar
Jan 2700:43:38Tap to summarizeRavi 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.Chapters00:00:00 You're not competing with AI, you're competing with people using AI00:01:27 From worst student to nuclear physicist to CEO00:03:03 Leading through influence, not control00:05:47 Betting on unconventional talent and upward mobility00:08:25 Rethinking education — Learning, working, and earning together00:11:18 AI as equalizer — The bottom gains more than the top00:14:05 Jobs won't disappear — They'll multiply00:15:58 The training crisis and velocity of change00:18:27 Code generation and the agentic future00:23:00 Amplify humans, don't replace them — A counter to Turing00:31:21 Corporate responsibility and the Synapse Initiative00:34:16 What keeps him up at night — Regulation, inequality, and the race00:38:55 Corporations as platforms for societal change00:40:41 Advice for the next generation — Master interdisciplinary thinking
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You Can Change a Lot More Than You Think — Somatic Coach Harley Frank
Dec 1701:00:57Tap to summarizeHow 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.CHAPTERSChapters00:00:00 Intro — You can transform more than you think00:03:47 From tech executive to somatic coach00:12:10 What somatics actually is00:14:59 Why shame runs the show00:17:19 Inner child work and neural rewiring00:24:45 Leadership is about embodiment00:31:08 The first step — Building a daily practice00:37:40 Feel your part, no more00:43:05 Pain vs. suffering — The 90-second rule00:51:53 Shame, technology, and staying presentIS 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!
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