Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondo

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.

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

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!

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!

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