Great Chat

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/

AI companies spent millions on Super Bowl ads, but none of them stuck! This week, we're joined by Dan Stroud, who runs an ad agency for tech companies, to break down what went wrong, what (if anything) went right, and whether startups should even be buying Big Game spots. Plus: the Winter Olympics, the flood of "SaaS is dead" takes, and more. 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.fm⁠.

Welcome back to year two of Great Chat. This week, the pod covers Chinese peptides, Brexit (the fintech exit, not the UK's withdrawal from the EU), Clawdbot/Moltbot/Moltbook, and contemplates whether there is a vibe shift in just one month into the new year. Does building in public work anymore? Did it ever? What takes its place? Has tech's reaction to the Epstein files proved that there is, in fact, a line for bad behavior? There were times we weren't so sure in 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.fm⁠.

As we wrap up 2025, we look at the stories tech told itself—and why they worked. From the bundling of everything, knowing when to make a change yourself in a rapidly changing labor market, and a lesson that you can survive any scandal as long as you keep winning. Plus, we weigh in on the SaaS debate ("Storytelling" as a Service), those Vanity Fair photos, and whether being hot is AI-proof. Mercury is back as the headline sponsor for season three! 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.

Aubrie Pagano, GP at Alpaca VC, joins the chat! We talk about why no one is talking about what happens after AGI, and then dive into Aubrie’s mind-bending effort to tackle the subject with The Aquarius Economy: part white paper, part science fiction, part investing thesis. We also compare our Granola Crunched results (we *are* amazing at zooms, ty), contemplate why no one seems excited about Netflix’s bid to buy Warner Bros, and discuss some shocking new stats from the NYT about the sex lives of young people. Mercury is back as the headline sponsor for season three! 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.

Inspired by Sam Altman’s “code red” for ChatGPT in the wake of the Gemini 3 launch and the rumored beef between the Kalshi and Polymarket founders, we talk about legendary tech rivalries. Uber versus Lyft, Rippling versus Deel, Jobs versus Gates, and much much more. What are the different flavors, and do they make you better, or is the drama a distraction? Also: the tech industry’s response to the New York Times piece on David Sacks. Mercury is back as the headline sponsor for season three! 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.

Our obligatory Thanksgiving episode, with a twist. We're sharing what we're grateful for now - even if it felt devastating at the time. The setbacks, the lucky breaks, the uncomfortable truths. Plus Nano Banana, Ryan Lizza Substack part 3, Rippling v Deel part 17, and more. Happy Thanksgiving - we're grateful for our listeners! Mercury is back as the headline sponsor for season three! 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.fm⁠.

This week, we get real about the benefits and tradeoffs of making the transition from a traditional full-time role in tech to taking a portfolio approach to your career. And it’s not just about income—you’ll have to rethink identity, purpose, time management, and more. Should you do it, and when? On a lighter note: we thank Bill Ackman for single handedly reviving the institutions of dating and marriage with four little words: “May I meet you?” Mercury is back as the headline sponsor for season three! 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.fm⁠⁠⁠⁠.

This week, we dare to ask the question: Are there limits to founder mode when it comes to your online persona? And when does building in public hurt more than it helps? We also unpack the latest tech Twitter drama—the monagamish guy, Marc Andreessen versus the pope—for anyone who isn’t terminally online (lucky you). Lastly: Happy 70th birthday, Kris Jenner! Mercury is back as the headline sponsor for season three! 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.fm⁠⁠⁠.

This week on Great Chat, we celebrate Election Day by talking about… talking about politics in the workplace. Yoni Rechtman, Partner at Slow Ventures and friend of the pod, joins us to discuss politics, humanoids, AI wearables, Sam Altman, and how’s he’s successfully unlocked opportunities in venture (hint: get good at having hard conversations). Mercury is back as the headline sponsor for season three! 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.fm⁠⁠.

This week on Great Chat, every media company wants to be a tech company, and every tech company wants to be a media company. We unpack what has been happening in the world of media: Big M&A, streaming wars, the Ellisons are the new Murdochs, and where short dramas stand now. We also learn that Ashley has finally watched KPop Demon Hunters, we share our deepest secret (our Netflix algorithm), and riff on travel etiquette with the upcoming holiday season. Happy Halloween! Mercury is back as the headline sponsor for season three! 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.fm⁠.

This week on Great Chat, we ask the question everyone’s whispering ... what happens if we’re in an AI bubble? We unpack the signals, the hype, and what founders and investors should be thinking about. Plus, a quick detour into the wild jewelry heist at the Louvre, the new ranking shakeup at Benchmark, and why AWS might just be the real backbone of the internet today. Mercury is back as the headline sponsor for season three! 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.fm⁠⁠⁠⁠⁠.

This week on Great Chat, it’s Spooky Season! Join us as we discuss the ultimate Halloween matchup overtaking social media, what Goldman’s acquisition of Industry Ventures means, and a rapid fire of our fall favorites. We also reflect on whether we as investors and operators need a five year plan the same way the businesses we work at and invest in do. How do you set goals in an uncertain environment? What are the best ways to assess your own progress in your career? How do you know when it’s time to make a change? For a group of Type A millennials - the discussion may surprise you. Mercury is back as the headline sponsor for season three! 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.fm⁠⁠⁠⁠.

It’s SF Tech Week, and there’s lots of AI news - surprise! We talk about why OpenAI’s less polished DevDay meets the moment, reflect on the Sora 2 launch, and give Anthropic props for a well executed coffee shop pop-up. Inspired by Anthropic, we go deep on challenger brands and why the #2 spot is more enviable than you might think. Startups, it’s time to embrace your David era. Mercury is back as the headline sponsor for season three! 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.fm⁠⁠⁠.

This week on Great Chat, we explore how to AI proof your career. We reflect on what our younger selves would do differently today, and share advice for college students navigating a rapidly changing job market shaped by AI. We also react to OpenAI’s new Sora app, Meta’s Vibes launch, and the claim that “triple, triple, double, double" startup growth is a thing of the past. Mercury is back as the headline sponsor for season three! 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.fm⁠⁠.

This week, we asked a longtime friend and favorite tech journalist to join the chat: Casey Newton of Platformer and Hard Fork fame! We dig into the tech media landscape: The rise of podcasts and newsletters as formats of choice, “going direct” as a viable strategy for getting reporters’ attention, and why some startup PR agencies might be kinda screwed. We also break down Anthropic’s $1.5B class action settlement and its implications for AI training and fair use, as well as Anthropic’s do-gooder image. Mercury is back as the headline sponsor for season two! 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.fm⁠.

This week on Great Chat, we talk about knowing when to walk away. We share our own stories of leaving at the peak of our careers to enter new industries, and unpack recent departures from Nat Friedman, Daniel Gross, and Suhail Doshi, as well as the great returns of Ryan Peterson at Flexport and Ty Haney at Outdoor Voices. We also add perspective on the "996" culture and explore how Anguilla is making $$$ from the AI boom. Mercury is back as the headline sponsor for season two! 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.fm⁠.

This week, we tackle a taboo topic: age. Is it harder than ever for young people to break into tech, or does it just feel that way? What does career longevity look like, especially for people who don’t hit escape velocity in their 20s? Also: we grapple with Serena Williams' Ro partnership, fantasize about the Meta and Midjourney licensing discussions, and plot a Great Chat Camp for Burning Man 2026. Mercury is back as the headline sponsor for season two! 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.fm⁠.