Is This Working?!

There are two types of hyper successful people. The ones who have an answer for everything, and the ones you actually want to talk to. Mark Nunnelly is squarely in the second camp. He joined Bain Capital in its early years and became one of the most successful investors in the world. Then, in his late fifties, he went to work for the governor of Massachusetts, where he led 5,000 people and started the state's first cybersecurity department from scratch. And he spent his hour with Connor talking about what he doesn't know. About parenting, which he says he got "spectacularly wrong" in places and calls the best thing he ever did. About capitalism, which he still calls the winning model even though "we have not had the shared prosperity that we need." And about AI, where his read is that "we're looking at the movie in its first minutes," and everyone is already describing the final scene. They get into: why the companies we think are winning AI today probably won't be the ones that win why "follow your passion" needs an asterisk, and the evidence to look at instead what he would do with $100 million to do the most good, and why it starts with medicine thirty years of work on American education, and why it left him less hopeful and more determined the eulogy test, and the two decisions he ranks above everything else he did If you're making big calls right now without knowing how any of this ends, this one is for you. Chapters 00:00:00 Intro 00:01:09 From a preacher's kid to private equity 00:03:46 People can't know how much you know until they know how much you care 00:04:57 Leaving Bain for public service 00:06:43 Luck, and following your passion with an asterisk 00:10:29 Look at the pattern, and get comfortable failing 00:12:04 The eulogy test, marriage and fatherhood 00:15:37 Thirty years of education reform 00:20:45 Choosing possibility over catastrophe on AI 00:29:24 Capitalism and shared prosperity 00:32:11 "Just tell me it's going to be okay" 00:32:45 The $100 million question 00:35:25 Why today's AI winners won't stay the winners 00:38:36 Two handfuls of unelected people 00:39:56 A kid off the turnip truck from Kentucky 00:43:20 A year around the world with a small backpack 00:44:42 Intensely, neurotically calm 00:45:49 The next chapter

Andrew Evans is a magician, but his real job? Gaining people's trust. Whether he's headlining at The Magic Patio, the SF venue he created that now sells out three months in advance, or working as a design lead at IDEO and Nike, helping clients tackle problems differently, his work is always about one fundamental question: How do I earn the trust of everyone in this room? His answer? Surprise. Take the disaster of a video call he had with a team in Korea. Echo, feedback, nobody able to see anybody. Finally, after fifteen grueling minutes, they get it working, and Andrew clicks through to the agenda slide he'd built a week earlier. First item: 9:00 to 9:15, technical difficulties. Everybody laughed, and then everybody relaxed. "We're not behind on anything. This is right where we're supposed to be." That's the magic trick: let people think one thing, and when they realize it was something else entirely, they know they're in good hands. In this episode, Andrew and Connor get into why he treats a flop as a persona failure and not a personal one, the ten-second question to ask before you design anything for your colleagues, and why making his Zoom setup more professional made people trust him less. If you want your next pitch or offsite to bring some real joy instead of corporate cringe, this episode's for you. Chapters 00:00:00 The mutant magician who infected IDEO's DNA 00:00:53 The BDSM approach to opening a magic show 00:08:22 Technical difficulties: the slide deck joke that built trust 00:11:04 Consider the context: the hack for creating wonder 00:14:39 Casting clients as investors 00:16:13 Snapping people out of Zoom multitasking 00:18:13 The psychology of deception 00:25:34 Adult-like wonder vs childlike wonder 00:30:26 Be creative by standing on the backs of giants 00:36:00 Being liked: the persona vs the person 00:40:41 Purpose is a byproduct, not something you find 00:43:19 From roller coasters to the Magic Patio 00:46:32 Shake up your routines and add randomness 00:49:24 Let's do some magic

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

"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

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