Great Chat

38:57

The launch industrial complex

Great Chat ·

2026/10/07

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

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38:18

What does the tech industry owe San Francisco?

Great Chat ·

2026/10/01

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

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40:14

Doomers at Dreamforce

Great Chat ·

2026/09/23

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,

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42:08

Tech's short-term era

Great Chat ·

2026/07/30

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

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40:30

Too big to laugh: how tech lost its sense of humor

Great Chat ·

2026/07/22

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

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42:41

Never follow your heroes (on X)

Great Chat ·

2026/07/17

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

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42:04

SPVs have a brand problem

Great Chat ·

2026/07/08

The SPV drama keeps coming, this time with some new main characters. We break down the public spat between AngelList-affiliated USVC, Anduril co-founder Matt Grimm, and the SPV/fund manager caught in the crossfire. We explore the mounting pressures around deal access and liquidity contributing to the explosion of SPVs, and why SPVs keep taking reputational damage for what's really an incentives problem. Plus: Fable is back (kind of), Angela survived her cruise with a new appreciation for hygiene

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38:37

Maybe Twitter isn't real life

Great Chat ·

2026/07/02

This week on Great Chat, The New York Times piece about San Francisco's "struggling" six-figure earners has Helen and Ashley doing the math on their early-20s rent checks. Then: the New York congressional primary results, where the biggest Twitter personalities got the fewest votes (and the guy with no following won??). Ryan Petersen calls remote work "white collar fraud," the internet responds, and it's actually kind of productive? And very sadly, Om Malik passed away at 59, and the outpouring from

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36:21

How much data do we actually want about our bodies?

Great Chat ·

2026/06/24

Inspired by Midjourney’s foray into full-body scanning, we dig into our industry’s obsession with health and longevity. From the earlier wave (think: 23andMe, Forward) to this current era (Prenuvo, Function, Neko), those of us in tech have been eager early adopters. But what are the tradeoffs in a system that isn’t designed to act on all this information? Plus: the pro-natalists are split on Anne Hathaway’s latest pregnancy, GLP-1s change women’s lives way more than men’s, and WIRED’s invitation to

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39:03

After you ring the bell

Great Chat ·

2026/06/17

This week on Great Chat, we talk about the biggest IPO in history, the wealth to follow, and what people from prior liquidity events in our industry have learned about money, identity, and happiness. We also cover venture-backed M&A activity, revisit "why Twitter is not real life," and hypothesize how Anthropic will recover from its current fall.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

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42:48

Founders dish on VC bad behavior (and bring receipts)

Great Chat ·

2026/06/10

Over the past week, our Twitter feeds were filled with stories that rarely get told: VCs behaving poorly in pitch meetings. Some founders even named names. What does it say about this moment that founders are publicly sharing these tales? And where are we in the spectrum of founder friendliness? Plus: OpenAI joins the IPO party with a confidential filing, Hunter Biden is the antithesis of the looksmaxxing trend, and maybe escorts are a social good? Go Knicks!Mercury is back as the headline sponsor

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33:46

Who are the billboards for?

Great Chat ·

2026/06/04

You can’t turn around in San Francisco without seeing a startup billboard…or five. We share some of our favorite marketing stunts of all time, and talk about why startup-branded shuttles and cafes are all the rage in our current era. Plus: more SpaceX S-1 talk (we can’t get enough), with Anthropic’s confidential filing close on its heels. It’s going to be a fun few months in the group chat.Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology

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43:00

AI services, so hot right now

Great Chat ·

2026/05/27

The AI labs’ ARR charts only go up and to the right, but actual diffusion through the Fortune 500? Way messier. This week, Jaclyn Rice Nelson, co-founder and CEO of Tribe AI (and Ashley's partner at Coalition), joins the chat to explain why OpenAI and Anthropic each stood up their own deployment companies. We discuss why the big consultancies can’t get the job done, and why "change management" is the wrong frame for what's actually a from-scratch refactor of how enterprises work. Plus: SpaceX's

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41:16

Dear Graduates: we’re sorry about the Schmidt speech

Great Chat ·

2026/05/20

Eric Schmidt delivered a pitch for AI to the University of Arizona graduating class—and the audience was not having it. We break down the nuance behind those boos, and grapple with the reality that no tech leader could have delivered a rousing AI speech in this moment. On the bright side, Schmidt sent us down a fun rabbit hole, reviewing some of the best commencement speeches in recent history (RIP Steve Jobs). Plus: the most boring possible verdict in the Musk v. Altman showdown, the tweet about

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38:54

What does it mean to be mission-driven in 2026?

Great Chat ·

2026/05/14

We’ve come a long way from the idealistic startup missions of the 2000s and 2010s. Today’s mission statements (when they exist) are more adversarial and more capitalist. Did we lose something, or are we just being honest? Plus: secondary sales exacerbate the already crazy SF housing market, and blaming AI isn’t landing as well for the latest wave of tech layoffs.Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking

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36:20

The hills we’ll die on

Great Chat ·

2026/04/22

In this era of hot takes loosely held, we each reveal the hills we’re willing to die on. Helen defends advertising as the perfect business model, Angela says the maths never really math (so throw out your spreadsheets), and Ashley insists you only lose when you try to play someone else’s game. Plus: the Anthropic narrative shift, everyone loves Bret Taylor, and so long Tim Apple (hello Johnny Appleseed?).Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial

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38:53

Developer marketing when everyone is a developer

Great Chat ·

2026/04/15

When everyone is a developer, what does developer marketing even mean? This week on Great Chat, we're joined by developer relations expert Matt Palmer to discuss developer marketing and the eternal question of what's cool in San Francisco.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

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38:17

OpenAI's new media M&A and old media exposé

Great Chat ·

2026/04/08

In the wake of its historic $122B fundraise, OpenAI just wrapped one of the crazier weeks in news, but we couldn't miss the chance to zero in on its surprise acquisition of new media darling TBPN. We asked Alexia Bonatsos, early stage investor and former editor of TechCrunch (a new media darling from a prior era), to join the chat. Plus: Is Medvi a shining new example of company building, or a business milkshake duck? And what's the deal with VC firms removing controversial startup logos from their

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40:39

Go touch some grass (but don’t tweet about it)

Great Chat ·

2026/04/02

So we all survived Q1—barely. When the world gets crazy, how do you stay sane? Spoiler alert: we don’t have any answers, but we have lots of hot takes. Plus: Mac opens a factory and schools us on submarine life, we wonder if anyone has reached Goldilocks status of being just the right amount online (not us), and it turns out AI may not have the polarizing effects of social media—we love a narrative violation.Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a

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35:18

Bubble talk

Great Chat ·

2026/03/26

We’re hearing the B word a lot more lately, and while it’s clear there’s a valuation bubble, we’re not betting on a correction just yet. Plus: OpenAI trades its “you can just do things” era for focus (RIP Sora and assorted side quests), Emil Michael shows us what it means to hold a grudge, and we Delve into the latest alleged bad behavior in startupland.Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services

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