Great Chat

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 pr...

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, a...

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...

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 tw...

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 look...

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. Mercur...

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...

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 (RI...

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 sp...

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 Appl...

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 Cho...

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 bus...

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 narrativ...

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...

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 wit...

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 bac...

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 aga...

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 fa...

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....

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...

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 fa...

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...

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 Netfl...

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...

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...