Great Chat

Doomers at Dreamforce

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 cont

Tech's short-term era

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-ter

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

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 Alexi

Never follow your heroes (on X)

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

SPVs have a brand problem

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 t

Maybe Twitter isn't real life

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

How much data do we actually want about our bodies?

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

After you ring the bell

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 mo

Founders dish on VC bad behavior (and bring receipts)

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 s

Who are the billboards for?

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-

AI services, so hot right now

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

Dear Graduates: we’re sorry about the Schmidt speech

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 gr

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

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.

The hills we’ll die on

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 ne

Developer marketing when everyone is a developer

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 develope

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

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

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

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

Bubble talk

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

Are startup HR teams okay?

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

What comes after the Girl Boss?

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