This week on Great Chat, the pod talks about their best managers (and what made them great), contemplates Alcatraz Island and the Met Gala, and explains why high-growth startups are the best places to work early in your career. And, congrats to the USC student for winning the sperm race!
The Rippling and Deel saga keeps on giving. Is this tech’s version of the Blake versus Justin publicity battle, or are we talking Kendrick and Drake? We break down the latest, and debate whether the playbook for crisis comms has fundamentally changed. We also weigh in on a Semafor piece about the group chats where powerful figures from tech and politics are shaping our reality (our group chat was not included…rude).
What are the biggest mistakes people make when starting a company or venture fund? Rachel Proffitt, the CEO of Cooley, joins us this week to share her legal wisdom for future founders and fund managers. Meanwhile: ReelShort picks up where Quibi left off, Henry Blodget is back with a new publication and an AI newsroom, and a16z’s newest GP comes with a podcasting network.
Has the label “imposter syndrome” hurt more than it’s helped? We get real about our own experiences, and offer some tips and tricks. But first: we dissect the narrative around Blue Origin’s all-female mission. Was it a botched attempt at a feminist moment, or the perfect addition to 2025’s meme-worthy chaos? Just remember: if you’re offered a seat on a rocket ship…
Girl the tariffs, what’s the deal with Deel, Rippling effects, and other mom jokes. Plus, Mac shares a positive vision for bringing manufacturing back home. All this and more on this week’s Great Chat.
On this week’s great chat, we revisit a favorite twitter debate: where’s the best place to build a startup (and why is it still SF)? But first, we hit the headlines: the AI wave has minted 29 new billionaires, and Elon has so many companies they’re buying each other.
From Bryan Johnson’s bizarre antics to the NDAs that keep scandals under wraps, Silicon Valley has a long history of looking the other way. In this episode, we dig into the latest controversies, revisit Uber’s reckoning, and discuss Careless People, the new book exposing Facebook’s inner chaos. Is tech failing to police itself? Or do we just love the drama until the next headline drops? Tune in as we break down why bad behavior in tech keeps making a comeback—and whether anyone actually cares. From your hosts this week: Ashley Mayer, Sally Shin, Helen Min and Angela Du.
This week on Great Chat, we discuss honeypots, pour one out for Forever 21, and share our perspectives and experiences with the equity portion of startup compensation.
This week, Sally's at HumanX, we're reminded of market events 25 and 5 years ago, make a case to bring back product review sites, and share our favorite (embarrassing) AI productivity hacks.
This week, Angela and Sally wonder if Amazon will ruin the Bond franchise, Helen confesses she could fall in love with Claude, and we all weigh in on Roelof Botha’s provocative SPV take. Our big topic: How to get started investing in startups alongside an operating career.
The very first episode of Great Chat: A podcast mostly about tech. Ashley's live from Upfront Summit, Angela's back in San Francisco with all of the eggs, and thoughts on latest news from LLM companies. Group discussion: Is building a personal brand required to be a great VC? And Mac takes us through this week's questions.
