Great Chat

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 environment? What are the best ways to assess your own progress in your career? How do you know when it’s time to make a change? For a group of Type A millennials - the discussion may surprise you.

Mercury is back as the headline sponsor for season three! 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 Eric Johnson from ⁠⁠⁠⁠LightningPod.fm⁠⁠⁠⁠.

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 the headline sponsor for season three! 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 Eric Johnson from ⁠⁠⁠LightningPod.fm⁠⁠⁠.

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 headline sponsor for season three! 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 Eric Johnson from ⁠⁠LightningPod.fm⁠⁠.

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 action settlement and its implications for AI training and fair use, as well as Anthropic’s do-gooder image.

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 making $$$ from the AI boom.

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 2026.

Mercury is back as the headline sponsor for season two! 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 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 burgers, psychedelics, and KPop Demon Hunters.

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 meetings with associates, do all co-founders need to pitch? Plus: The tech giants embrace hustle culture, GPT-5’s launch sparks public mourning for its predecessors, and the negative gross margins of coding apps bring back memories of ZIRP.

Mercury is back as the headline sponsor for season two! 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 Eric Johnson from ⁠LightningPod.fm⁠.

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 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 Eric Johnson from LightningPod.fm.

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 for season two! 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.