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Is This Working?!: Daily Summaries Delivered
by Connor Diemand-Yauman
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.
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- 1 weeks ago49 min
Why Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina Stembel
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.
- 3 weeks ago49 min
Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy Narula
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
- Apr 29, 202649 min
Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondo
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!
- Apr 8, 20261h 7m
The Slowest Career Change In History | Magician David Gerard
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!
- Mar 25, 202647 min
Why She Took the Hardest CEO Job in America | PG&E's Patti Poppe
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
- Mar 11, 202639 min
The Overachiever’s Guide To Effective Communication - Stanford's Matt Abrahams
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
- Feb 25, 202650 min
Jin Ha (Hamilton, Only Murders In The Building): Stop Performing and Start Breathing
"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.
- Feb 11, 202656 min
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!
About 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?! 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.
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