Is This Working?!

Connor Diemand-Yauman
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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.

  1. 3d ago ·  Video

    The Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha Anand

    Nisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times. 53,000 people are home from federal prison because of that one bill. Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired? "Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life." We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus. Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for? If you've ever wondered whether the work is worth what it's costing you, this one is for you. Chapters 00:00:00 Fake blood, arrests, and the woman who gets sh*t done 00:01:08 Growing up rebellious 00:06:05 Punk rock and straight-edge hardcore 00:08:54 The circus arrest 00:14:11 Myanmar prison and five years of hard labor 00:23:25 The elevator with Marjorie Taylor Greene 00:26:18 Finding common ground without selling out 00:28:32 The First Step Act — 53,000 people home from prison 00:39:18 Would young Nisha think you're a sellout? 00:55:58 Exhausted but optimistic — why she can't stop 00:59:50 The trap of working hard 01:14:41 Power, unlikely allies, and what comes next

    The Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha Anand

  2. Aug 26 ·  Video

    The Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWine

    "You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times. First, he lost. Then he won. Then he won again. And then he lost. After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone. His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done." DeWine wasn't done. Next, he ran for Attorney General of Ohio and won. Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including: whether the American Dream can survive the AI revolution why the worst thing a leader can be is the smartest person in the room DeWine's thirty-year history of humanitarian work in Haiti his secret to remaining stubbornly optimistic (hint: have eight kids) Plus: the box of chocolates in sixth grade and the line his whole career comes down to: "Work is the price we pay to achieve what we want. No shortcuts." If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you. CHAPTERS: Chapters 00:00 The career nobody wins by accident 00:06:53 Learning to lose — The 2006 Senate defeat 00:10:03 Never be the smartest person in the room 00:13:31 59 years — The partnership that started in first grade 00:21:41 Is the American Dream dead? 00:26:55 AI, critical thinking, and muddling through disruption 00:31:48 30 years in Haiti — Why he keeps going back 00:36:47 Springfield and the eating dogs rumor 00:38:30 What's next — Leaving the governor's mansion 00:41:03 Work is the price we pay — Advice for the next generation

    The Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWine

  3. Aug 12 ·  Video

    Running Sesame Street Is Harder Than Working in the White House: Sesame Workshop CEO, Sherrie Westin

    Everyone loves Sesame Street. Now imagine being in charge of it. That's Sherrie Westin's job. As CEO and President of Sesame Workshop, Westin's day-to-day includes: figuring out how to explain to a four-year-old that a parent is in prison. Deciding whether Elmo wears a mask during the pandemic, knowing half the country will be furious either way. Spending three years with every autism organization in America building a single Muppet. Doing layoffs in the hardest year the place has ever had. And answering the question she can't get away from: how do you stay true to your values and remain a beacon without becoming a lightning rod? She ran a television network before this. She worked in the White House. She says this one is harder than both. "People are like, how hard could it be? You're hanging out with Muppets. Yeah, right." What nobody tells you about Sesame Street is that it's a research operation. They tried a storyline about divorce, tested it, found it was scaring kids, and killed it. When they built Julia, the first autistic Muppet, they got every autism organization in one room, groups that disagreed with each other on almost everything, and found the one thing they all agreed on. A mother wrote in afterward. She'd never been able to find the words to tell her five-year-old she had autism, until her daughter saw the Muppet Julia on Sesame Street. Her daughter's reaction: "So I'm amazing too, right?" Plus: Big Bird's actual age, why she hires for a sense of humor, and what a lot of adults could stand to learn from a show made for three-year-olds. CHAPTERS Chapters 00:00:00 Managing Big Bird is harder than running the White House 00:01:44 The hidden complexity of Sesame Street 00:06:21 Reaching 500 million children — The scope of Sesame's mission 00:10:26 Creating Julia, the first autistic Muppet 00:14:22 "So I'm amazing too, right?" 00:17:28 Staying nonpartisan when everything is political 00:23:06 Big Bird is six years old 00:27:01 The hardest part: downsizing and losing USAID funding 00:30:40 Screen time guilt

    Running Sesame Street Is Harder Than Working in the White House: Sesame Workshop CEO, Sherrie Westin

  4. Jul 29 ·  Video

    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-f***s 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

    No One Knows Katie Couric Like This

  5. Jul 8 ·  Video

    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

    How to Make Yourself AI-Proof, According to One of the World's Top VCs - Ann Miura-Ko

  6. Jun 24 ·  Video

    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

    How to Actually Change Your Behavior (No, It's Not Willpower) — Behavioral Scientist Kristen Berman

  7. May 27 ·  Video

    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.

    Why Real Leadership Feels Like Crap — Farmgirl Flowers Founder Christina Stembel

  8. May 13 ·  Video

    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

    Don’t Follow Your Passion — Do This Instead | Crankstart Foundation's CEO Missy Narula
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5
out of 5
19 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
    18
  • Rating
    Explicit

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