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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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- Today51 min
No One Knows Katie Couric Like This
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
- 3 weeks ago57 min
How to Make Yourself AI-Proof, According to One of the World's Top VCs - Ann Miura-Ko
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
- Jun 24, 202641 min
How to Actually Change Your Behavior (No, It's Not Willpower) — Behavioral Scientist Kristen Berman
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
- Jun 10, 202652 min
Politics Is the Problem. Politics Is the Solution — Manny's Founder Manny Yekutiel
What if politics didn't feel like homework? What if, instead, it was built on a foundation of love, community, and — most importantly — joy? Disowned by his Orthodox Jewish father for coming out, he showed up in San Francisco fourteen years ago with nothing. He says the city gave him everything. So he got to work giving it back. First, he built Manny's, the Mission gathering space where engagement, disagreement, action, and hope can flourish (and a required campaign stop for Democratic presidential candidates). Now, Manny is running for District 8 supervisor, Harvey Milk's old seat. Connor and Manny get into why joy is the most serious tool any politician has, how a guy who lost his dad built a home for a whole city, and why running for office might be the best dating strategy out there. If you're tired of politics feeling like a chore, this one's for you. Chapters 00:00:00 Intro — Politics is the problem, politics is the solution 00:01:46 Coming out, being disowned, finding home in SF 00:04:55 Building Manny's — A civic gathering space for democracy 00:06:37 Dating a ballet dancer and enjoying the journey 00:09:01 Loneliness and feeling outside the camp 00:10:58 The craziest moments at Manny's 00:17:16 Why I'm running for office — I owe the city 00:23:34 Change is possible — Politics is the only thing standing in our way 00:33:06 The Civic Joy Fund — Why joy matters in politics 00:35:01 Community organizing 101 — How to build from scratch 00:37:24 Gay, Jewish, and faithful — Reconciling identity and spirituality 00:44:10 The housing crisis — Building 10,000 new homes in District 8 00:49:55 Burning bright — Harvey Milk's legacy and living fully 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!
- May 27, 202649 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.
- May 13, 202649 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!
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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