Hello Monday with Jessi Hempel

We've built an economy that rewards destroying value. Eric Ries wants to know how we got here, and whether we can build our way out.

Eric wrote The Lean Startup in 2011 and helped define a generation of entrepreneurs. Since then, he's watched promising, mission-driven companies get hollowed out, and he thinks he knows exactly why. His new book, Incorruptible: How Good Companies Go Bad and How Great Companies Stay Great, is his attempt to name what's happening, explain how we got here, and lay out a blueprint for building something better. 

In this episode, Jessi and Eric discuss:

What Eric calls "financial gravity": the systemic force that pulls organizations away from their mission and toward extraction

Why shareholder primacy isn't ancient law; it's a 1980s invention that was never voted on by anyone

The private equity problem: how you can taste the cost-cutting in your food when private equity buys your favorite restaurant

Why today's best practices are actually value-destroying, and what the data says about the alternative

The Public Benefit Corporation filing: a two-page form that could change what your company is legally obligated to do

Why "it's always too early until it's too late," and how founders miss their window to protect their mission

The AI layoff glee: why Eric thinks companies racing to replace people with robots is slow-motion suicide

How to find opportunity in this moment, even if you've been laid off, and why trust is the most underrated asset in business today

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Joanna Stern spent a year using AI to do (almost) everything: write her emails, analyze  her medical records, text her wife, drive her around, and even fold her laundry. The result is her new book, I Am Not a Robot, which documents what she learned testing AI as a journalist, a parent, and a newly independent founder.

Joanna spent over a decade as a tech reporter at The Wall Street Journal before leaving to launch her own media outlet, New Things. She brought the same approach that's defined her career — hands-on, consumer-first testing of the technology itself — to her year-long experiment in living with AI.What she found was more nuanced than the hype: some of it works, some of it really doesn't, and some of it needs guardrails.

In this episode, Jessi and Joanna discuss:

Why the same AI technology that's transforming cancer detection is also upselling you at the dentist

The data privacy moves everyone should make right now, including the settings most people never touch

What happened when Joanna tried to let AI handle all her communications

Why robots are bad at folding clothes

How AI gave Joanna the confidence to leave a staff job and start a business

The emotional difference between work you make yourself and work a machine makes for you

What it means to raise kids in a world where the struggle of figuring things yourself might disappear entirely

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Comedy writer Jenny Hagel has six Emmy nominations. The other week, she wrote 20 jokes. One made it to television. She doesn’t see this as failure, though. It’s the nature of the job. And it might offer the most useful career lesson you'll hear all year.

Jenny is a writer on Late Night with Seth Meyers, where she also regularly appears on camera in the popular segment Jokes Seth Can’t Tell. She is also the author of a new book of essays called Advice No One Asked For. In this episode, Jessi Hempel sits down with Jenny to talk about the arc of her non-traditional career, and what it actually takes to keep going in the face of failure.

In this episode, Jessi and Jenny discuss:

The live advice show Jenny built during the writer's strike, and how a room full of strangers asking earnest questions accidentally became the most community-building thing she's ever done

How humor acts as a spoonful of sugar that lets us endure the heavy stuff a little longer

The 411 call that landed Jenny a grad school internship

Why the find-yourself period matters, and what gets lost when young people skip it

The writing advice Jenny gives everyone: the part where you create and the part where you judge have to be two completely separate steps

How growing up queer in the '80s and '90s inadvertently became a blueprint for every out-the-box decision she's made since

Why a creative career isn't all-or-nothing, and what the middle actually looks like

Find Advice No One Asked For wherever books are sold, and follow Jessi Hempel on LinkedIn.

Lesbian bars aren’t just nightlife, they’re evolving spaces of community and chosen family, and they have a special place in Jessi Hempel’s heart. On this bonus episode, Jessi sits down with one of Hello Monday’s own producers,  Rachel Karp, to talk about her new book The Lesbian Bar Chronicles: The Living History and Hopeful Future of America's Dyke Dives and Sapphic Spaces. 

Rachel’s journey started as a passion project: a documentary podcast in which the Cruising podcast team went on a road trip to visit every lesbian bar in the US. Their goal was to tell the history of lesbian bars and stories of the people who go to them. Now, those stories– and the lessons we can learn from them about how to create real-life community spaces–are in a book.

In this episode:

Why Rachel and the Cruising podcast team went on their road trip

Why lesbian bars have endured, even as culture, technology, and rights have shifted

What makes physical spaces of belonging different from digital communities

The role of leadership in shaping inclusive, values-driven spaces

What “chosen family” looks like in practice, and why it matters

What anyone (queer or not) can learn from lesbian bars

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We're trained to climb ladders and chase titles, but what if the real metric of career success was the positive impact you have on the world? In this episode from the Hello Monday archives, host Jessi Hempel sits down with Rutger Bregman to explore moral ambition—a framework for building a career based on what positive impact you can have on the world. 

Rutger's groundbreaking book, Moral Ambition: How to Stop Wasting Your Talent and Start Making a Difference, is a wake-up call for anyone who's felt something was missing from their work. Whether you're early in your career, questioning your path, or rebuilding after a layoff, this conversation offers a practical roadmap for pivoting toward meaningful work.

In this episode, Jessi and Rutger explore:

What moral ambition is, and why it's the antidote to burnout

Why "follow your passion" is the wrong advice for building a sustainable career

How to shift from success-driven to service-driven work

Which industries funnel talented people into unfulfilling roles, and how to break free

Real-world examples of people solving humanity's biggest problems

How to build coalitions and find collaborators aligned with your values

The hidden cost of prestige, and how to redefine what winning looks like

This episode is a call to action for anyone who wants to do good—and do it well.

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