Great Chat

This week, we get real about the benefits and tradeoffs of making the transition from a traditional full-time role in tech to taking a portfolio approach to your career. And it’s not just about income—you’ll have to rethink identity, purpose, time management, and more. Should you do it, and when? On a lighter note: we thank Bill Ackman for single handedly reviving the institutions of dating and ma...

This week, we dare to ask the question: Are there limits to founder mode when it comes to your online persona? And when does building in public hurt more than it helps? We also unpack the latest tech Twitter drama—the monagamish guy, Marc Andreessen versus the pope—for anyone who isn’t terminally online (lucky you). Lastly: Happy 70th birthday, Kris Jenner! Mercury is back as the headline sponsor...

This week on Great Chat, we celebrate Election Day by talking about… talking about politics in the workplace. Yoni Rechtman, Partner at Slow Ventures and friend of the pod, joins us to discuss politics, humanoids, AI wearables, Sam Altman, and how’s he’s successfully unlocked opportunities in venture (hint: get good at having hard conversations). Mercury is back as the headline sponsor for season...

This week on Great Chat, every media company wants to be a tech company, and every tech company wants to be a media company. We unpack what has been happening in the world of media: Big M&A, streaming wars, the Ellisons are the new Murdochs, and where short dramas stand now. We also learn that Ashley has finally watched KPop Demon Hunters, we share our deepest secret (our Netflix algorithm), and r...

This week on Great Chat, we ask the question everyone’s whispering ... what happens if we’re in an AI bubble? We unpack the signals, the hype, and what founders and investors should be thinking about. Plus, a quick detour into the wild jewelry heist at the Louvre, the new ranking shakeup at Benchmark, and why AWS might just be the real backbone of the internet today. Mercury is back as the headlin...

This week on Great Chat, it’s Spooky Season! Join us as we discuss the ultimate Halloween matchup overtaking social media, what Goldman’s acquisition of Industry Ventures means, and a rapid fire of our fall favorites. We also reflect on whether we as investors and operators need a five year plan the same way the businesses we work at and invest in do. How do you set goals in an uncertain environme...

It’s SF Tech Week, and there’s lots of AI news - surprise! We talk about why OpenAI’s less polished DevDay meets the moment, reflect on the Sora 2 launch, and give Anthropic props for a well executed coffee shop pop-up. Inspired by Anthropic, we go deep on challenger brands and why the #2 spot is more enviable than you might think. Startups, it’s time to embrace your David era. Mercury is back as...

This week on Great Chat, we explore how to AI proof your career. We reflect on what our younger selves would do differently today, and share advice for college students navigating a rapidly changing job market shaped by AI. We also react to OpenAI’s new Sora app, Meta’s Vibes launch, and the claim that “triple, triple, double, double" startup growth is a thing of the past. Mercury is back as the h...

This week, we asked a longtime friend and favorite tech journalist to join the chat: Casey Newton of Platformer and Hard Fork fame! We dig into the tech media landscape: The rise of podcasts and newsletters as formats of choice, “going direct” as a viable strategy for getting reporters’ attention, and why some startup PR agencies might be kinda screwed. We also break down Anthropic’s $1.5B class a...

This week on Great Chat, we talk about knowing when to walk away. We share our own stories of leaving at the peak of our careers to enter new industries, and unpack recent departures from Nat Friedman, Daniel Gross, and Suhail Doshi, as well as the great returns of Ryan Peterson at Flexport and Ty Haney at Outdoor Voices. We also add perspective on the "996" culture and explore how Anguilla is mak...

This week, we tackle a taboo topic: age. Is it harder than ever for young people to break into tech, or does it just feel that way? What does career longevity look like, especially for people who don’t hit escape velocity in their 20s? Also: we grapple with Serena Williams' Ro partnership, fantasize about the Meta and Midjourney licensing discussions, and plot a Great Chat Camp for Burning Man 202...

This week on Great Chat, we discuss some interesting findings from a newly released report from Mercury called "The New Economics of Starting Up." We learn that founders are becoming more creative with financing and team building in an AI-first world. Separately, we revisit SPVs and explore the creative ways investors are securing allocations in hot AI companies. And we have a great chat about bur...

We’re halfway through August and there’s still no summer slowdown in sight! As fall approaches, we gear up for a peak fundraising season with a favorite group chat topic: The dos and don’ts of raising venture capital. We share our takes on some of the most divisive topics as investors and founders: Do you need a warm intro, should you take money from scouts, when does it make sense to take meeting...

This week on Great Chat, we talk about the topic on everyone's minds: Figma’s textbook IPO. We compare it to the IPOs we experienced first-hand as early employees, investors and journalists: Facebook, Box, Dropbox and Uber. Plus: celeb sightings in SF (hello, Andrew Garfield) and products that were ahead of their time (RIP AI Pin). Mercury is back as the headline sponsor for season two! Mercury is...

In the era of “going direct,” do startups still need to care about media coverage? Actually, yes: LLMs are bringing the primacy of press back, but the way companies get covered has fundamentally changed. Also: Figma’s IPO looms, Astronomer claps back with some help from a friend, and we are transported to the days of Hot or Not with the Tea data spill (ugh). Mercury is back as the headline sponsor...

This week on Great Chat, we are getting personal. We share our stories of how we got into tech in the first place. The detours and the unexpected opportunities that defined our careers from covering IPOs to early days at Facebook and those long hours at Goldman. Also, is Hollywood starting to cosy up to AI? We talk about Netflix's flirtation with Runway. Plus Diamonds on our minds, and no, not all...

This week on Great Chat, we talk about the 96 hours of Windsurf frenzy that consumed Silicon Valley, and what the implications are for the (broken) social contract that tech startups have with employees. We also share notes from the Backstreet Boys Into the Millennium concert, what Sally is seeing at NBA Demo Day at Summer League, Bill Ackman’s foray into professional sports, the tea (or lack ther...

This week on Great Chat, we debate the impact and long-term effects of AI startup performance theatre. Should we be concerned? Plus: Twitter isn't real life, SF vs. NYC for dating, and why Big Tech might be your best bet for finding both a paycheck and a partner. Mercury is back as the headline sponsor for season two! Mercury is a financial technology company, not a bank. Banking services provided...

This week on Great Chat, we talk about the race for speed across startups and venture and why execution is everything right now. And yes, we also break down the Bezos wedding (we dared to speculate on the seating chart!) and the Meta vs OpenAI talent scoreboard. Plus, Sally finally learns the meaning of AI slop. Mercury is back as the headline sponsor for season two! Mercury is a financial technol...

The group chat kicks off season two of Great Chat with AI M&A (say that five times fast), leaks, and Labubus. Mercury is back as the headline sponsor for season two, and the rapid fire Q&A is now brought to you by Perplexity. How very apt. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members F...

This week on Great Chat, we’re diving into the question on everyone’s mind: what jobs are actually safe in the age of AI? Are VC roles really untouchable, as Marc Andreessen claims? Which careers are truly defensible? Could traditional media actually play a bigger role in shaping brands in an AI-powered world? Plus, we unpack Fidji Simo’s new role at OpenAI and what it might signal for the company...

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...

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…