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.

• 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!

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.

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

• 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

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.

• 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!

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.

• 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!

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.

• 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

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/.

• 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

"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.

"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

• 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!

Ravi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code.

He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone else.

In this conversation, Ravi and Connor dig into what most AI conversations miss: why entry-level jobs might actually expand, not disappear. Why "problem finders" will matter more than problem solvers. And why the old model of education → work → retire is already broken and in desperate need of disruption.

For anyone anxious about AI and the future of work, this is the conversation you didn't know you needed: a leader who sees what's coming and can actually explain where the opportunities are.

• 00:00:00 You're not competing with AI, you're competing with people using AI
• 00:01:27 From worst student to nuclear physicist to CEO
• 00:03:03 Leading through influence, not control
• 00:05:47 Betting on unconventional talent and upward mobility
• 00:08:25 Rethinking education — Learning, working, and earning together
• 00:11:18 AI as equalizer — The bottom gains more than the top
• 00:14:05 Jobs won't disappear — They'll multiply
• 00:15:58 The training crisis and velocity of change
• 00:18:27 Code generation and the agentic future
• 00:23:00 Amplify humans, don't replace them — A counter to Turing
• 00:31:21 Corporate responsibility and the Synapse Initiative
• 00:34:16 What keeps him up at night — Regulation, inequality, and the race
• 00:38:55 Corporations as platforms for societal change
• 00:40:41 Advice for the next generation — Master interdisciplinary thinking