Great Chat

With all this talk of looming layoffs and AI automation, we have to wonder: what’s the People/HR world like these days? Emily Herron, a longtime startup People leader and current HR Evangelist at Rippling, joined the chat to share her refreshingly candid and pragmatic POV. Plus: Travis Kalanick is back, baby, with the perfect narrative-moment fit. Meanwhile, Marc Andreessen breaks the internet with his latest hot take: the Great Men of history weren’t introspective. Please keep counterexamples to yourself.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

Inspired by International Women’s Day, we reflect on the different narratives for women in tech over the past few decades. From Sheryl Sandberg’s Lean In to the rise (and fall) of the Girl Boss to…whatever this moment is? We break down what’s actually helpful to women, and what’s just performative. Plus: Microsoft enters the chat with Copilot Cowork (say that ten times fast), Anthropic strikes back with a lawsuit against the Department of War, and Cluely’s latest stunt feels so 2025.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

AI makes a lot of things easier, but reading the room is not one of them. On this week's Great Chat, we discuss how this moment feels different from 2020 and 2008, and debate whether we will see a return to empathy from our tech leaders. How do you lead when no one knows what will happen next? It seems everyone could benefit from taking a deep breath right now. Plus, why Katy Perry is trending again, narrative violations by Cursor, and some awful analogies that remind us that the current moment doesn't fit neatly into past frameworks.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

This week, we revisit one of our favorite topics: how to decide between operating roles and the portfolio life when it comes to your career. Ceci Stallmith joins us to talk about jumping back into operating as head of marketing at Lovable, and we get radically candid about all the things: stepping off the career ladder, balancing work and parenting, and the power of going with your gut. We also fangirl over Alysa Liu, lament Dario’s recent keynote, and wonder whether employing humans will someday be a luxury flex.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

This week, we try to explain looksmaxxing…and almost certainly kill that linguistic trend in the process. Meanwhile in venture, each new AI fundraise is valuation-mogging the last, and we unpack what extreme capital concentration might mean for the startup ecosystem more broadly. Plus: dancing robots (Helen is not a fan) and what Wuthering Heights and Jack Altman joining Benchmark have in common.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/