Great Chat

Everyone’s waiting for the robot butler, but the first robot in your life might be your car. This week on Great Chat, guest host Jameson Detweiler, co-founder and CEO of Chip Motors, joins us to talk about whether robots need a personality, why “right-sized” might be the next big thing, and what it takes to get a family to trust a car that parks itself. Plus: OpenAI’s tougher fundraise, what the coming wave of AI millionaires will do with their money, Martha Stewart’s Halloween non-apology, and a shoutout to formerly cool dads and perpetually cool moms.

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

Amidst the human-extinction headlines, cybersecurity apocalypse warnings, and billionaires going viral for outsourcing parenting to AI, we do the most contrarian thing possible: find reasons for optimism. The full crew joined the chat to make the bull case: creativity barbelling between democratized slop and true genius, the “annoying” jobs getting automated first, AI as a true meritocracy lever, and value finally flowing to the work (caregiving, parenting, nursing) that was always undervalued. Plus: we won a Signal Award, marvel at Anthropic’s S-1, and Mac goes on an epic Instinct rant.

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

Between Anthropic’s soft Q3 and CoreWeave’s meltdown, everyone’s suddenly asking: is AI over? Spoiler: we don’t think so, but it’s going to be a bumpy ride. This week on Great Chat, we dig into IPO timing, the margin question nobody can answer yet, and why early-stage founders seem more optimistic than the late-stage crowd. Plus: Victoria’s Secret’s return to form, Elizabeth Holmes’s redemption arc, and the year’s best corporate security warning.

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

People beyond Silicon Valley used to love the products tech companies made. Now, they feel like AI tools (and data centers) are being shoved down their throats. This week, comms pro Aaron Zamost joins the chat to rant about tech’s reputational decline and leadership vacuum. Maybe what we really need is a spokesperson who is, well…normal (it's a lot to ask). Plus: we debate what has and hasn’t changed since Aaron’s famous “startup clock” essay from 2015, lament the AI to SI rebrands, and dissect Twitter beefs spanning Vinod Khosla and Kelly Clarkson.

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

In the AI slop era, pre-seed startups are spending real money on cinematic launch videos, renting creator armies, and prioritizing attention over substance. This week on Great Chat, Ashley and Helen ask whether manufactured hype has peaked, what comes next, and how a young startup can actually stand out when everyone is shouting. Plus: what's in a name? We dig into the proposed AI-to-SI name change, discuss AI safety, and debate whether AI can feel.

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

New York's restaurants are bankrolled by Wall Street money; LA's by Hollywood. So why has tech failed to leave a physical imprint on San Francisco? This week, Ligaya Tichy, founder of New Entity and an early community builder at Yelp and Airbnb, joins the chat to make the case for putting tech wealth to work in brick-and-mortar businesses. We get into San Francisco's evolution from nerd utopia to industry town, why the last generation of tech money didn't make its way to small businesses, and what a modern system of patronage could look like with the AI lab IPOs on the horizon. Plus, Dario's on-camera awkwardness, and Oura's cratering IPO "Readiness Score."

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

Great Chat is back in its sixth season with Ashley, Helen, and  guest host Taylor Lorenz. We dive into AI assistant wars, Dreamforce, the All In Summit, and Corgi in context. Plus, in our main topic, we break down Dario Amodei's "pacing" essay and discuss who actually benefits from the industry's current storylines.

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

Venture capital used to be the most patient money in finance. So why does it suddenly look like day trading? This week on Great Chat, the group digs into tech’s short-term era: founders leaving their own companies for nine-figure packages, emerging managers pitching early DPI, researchers switching teams, and a YC Startup School that filled Chase Center with mega-church energy. Plus, TK is back, Anthropic loses its aura, and Kalshi had a rough week. An optimistic takeaway: if no reputation is permanent, neither is any failure. Keep swinging.

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

The tech industry used to be way funnier; there was a whole HBO show about it! Now the timeline is earnest, angry or self-righteous, and rarely self-aware. Comedian Alexis Gay, who spent seven years working in tech and startups, joins the chat to diagnose what happened: tech got too big to be a cottage industry, too powerful to poke fun at itself, and too fragmented to share an inside joke. She also makes the case for why now is exactly the moment for a new Silicon Valley-style show. Plus: the Brian Chesky hack that nobody believes, why buying tech merch hits different than earning it, and the "directionally very bad" mug we all need ASAP.

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

This week on Great Chat, we grapple with the wave of tech leaders who are trading mystique for distribution and engagement-maxxxing. Is this the new world, and we're just boomers? Probably. But that's not going to stop us from crashing out over it. We also chat about Anthropic's latest model and television commercial, and comms blunders by Phia and 1X.

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