Great Chat

The hills we’ll die on

Wed, 22 Apr 2026 11:00:00 -0000

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 Appleseed?).

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 Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠⁠LightningPod

Developer marketing when everyone is a developer

Wed, 15 Apr 2026 17:30:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠LightningPod

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

Wed, 08 Apr 2026 12:00:00 -0000

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 business milkshake duck? And what's the deal with VC firms removing controversial startup logos from their websites (cough, Delve)?

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

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

Thu, 02 Apr 2026 15:57:00 -0000

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 narrative violation.

This podcast is edited by Eric Johnson from ⁠LightningPod

Bubble talk

Thu, 26 Mar 2026 15:58:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

Are startup HR teams okay?

Wed, 18 Mar 2026 22:45:00 -0000

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 with his latest hot take: the Great Men of history weren’t introspective. Please keep counterexamples to yourself.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

What comes after the Girl Boss?

Thu, 12 Mar 2026 14:15:00 -0000

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 back with a lawsuit against the Department of War, and Cluely’s latest stunt feels so 2025.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

Will empathy make a comeback?

Wed, 04 Mar 2026 21:03:00 -0000

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 again, narrative violations by Cursor, and some awful analogies that remind us that the current moment doesn't fit neatly into past frameworks.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

The best career decisions come from the gut

Wed, 25 Feb 2026 17:47:00 -0000

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 fangirl over Alysa Liu, lament Dario’s recent keynote, and wonder whether employing humans will someday be a luxury flex.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

Venture is in its growthmaxxing era

Thu, 19 Feb 2026 00:45:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

No one won the AI Bowl

Wed, 11 Feb 2026 15:30:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠LightningPod.fm⁠.

Is building in public over?

Thu, 05 Feb 2026 14:00:00 -0000

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 fact, a line for bad behavior? There were times we weren't so sure in 2025.

The stories we told ourselves in 2025

Tue, 23 Dec 2025 17:30:00 -0000

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 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.

So what happens after AGI?

Thu, 11 Dec 2025 00:40:00 -0000

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 Netflix’s bid to buy Warner Bros, and discuss some shocking new stats from the NYT about the sex lives of young people.

Code red: our favorite tech rivalries

Wed, 03 Dec 2025 21:00:00 -0000

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 New York Times piece on David Sacks. 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.

Thankful for the unexpected

Wed, 26 Nov 2025 13:00:00 -0000

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 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.

That Portfolio Life

Wed, 19 Nov 2025 23:30:00 -0000

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 marriage with four little words: “May I meet you?”

Turns out, there’s still a line (don’t mock the pope)

Wed, 12 Nov 2025 20:04:00 -0000

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!

Tech is getting more political—should you?

Thu, 06 Nov 2025 00:45:00 -0000

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).

The Ellisons are the new Murdochs (and we're ready for Succession round 2)

Thu, 30 Oct 2025 07:30:00 -0000

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 riff on travel etiquette with the upcoming holiday season. Happy Halloween!

Don't want to burst your bubble, but ...

Wed, 22 Oct 2025 18:38:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠⁠⁠⁠⁠LightningPod.fm⁠⁠⁠⁠⁠.

PSA: Don’t bother trying to plan your tech career

Thu, 16 Oct 2025 00:00:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠⁠⁠⁠LightningPod.fm⁠⁠⁠⁠.

David vs. Goliath, but make it venture-backed

Wed, 08 Oct 2025 15:40:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠⁠⁠LightningPod.fm⁠⁠⁠.

Too late to AI proof your career?

Wed, 01 Oct 2025 23:00:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠⁠LightningPod.fm⁠⁠.

The state of tech media (fact check not included)

Thu, 11 Sep 2025 02:18:00 -0000

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. 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.

The art of quitting

Wed, 03 Sep 2025 23:30:00 -0000

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. 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.

Are startups a young person’s game?

Wed, 27 Aug 2025 23:00:00 -0000

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 podcast is edited by Eric Johnson from ⁠LightningPod.fm⁠.

Is AI a job killer or job creator?

Thu, 21 Aug 2025 00:45:00 -0000

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. 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.

Warm intros and hot takes: It's time to get ready for fundraising season

Wed, 13 Aug 2025 23:00:00 -0000

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.

This podcast is edited by Eric Johnson from ⁠LightningPod.fm⁠.

We are so back (thanks, Figma)

Wed, 06 Aug 2025 23:02:00 -0000

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).

This podcast is edited by Eric Johnson from LightningPod.fm.

Does startup PR even matter anymore?

Wed, 30 Jul 2025 23:22:00 -0000

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).

The tech origin story: No straight lines

Thu, 24 Jul 2025 07:30:00 -0000

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 were about Coldplay and "a sky full of stars". 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.

Windsurf: The straw that broke the camel’s back

Thu, 17 Jul 2025 02:12:00 -0000

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 thereof) from Sun Valley, and the unfortunately named TITV.

This podcast is edited by Eric Johnson from LightningPod.fm.

When startups become theatre

Thu, 10 Jul 2025 00:24:00 -0000

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.

This podcast is edited by Eric Johnson from LightningPod.fm.

AI is killing the summer slowdown

Thu, 03 Jul 2025 00:00:00 -0000

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.

This podcast is edited by Eric Johnson from LightningPod.fm.

Much ado about acquihires

Thu, 26 Jun 2025 17:00:00 -0000

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 FDIC.

This podcast is edited by Eric Johnson from LightningPod.fm.

Are VC jobs truly AI Proof? (Marc thinks so)

Thu, 15 May 2025 19:46:04 -0000

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’s future.

Great managers, and what makes them great

Thu, 08 May 2025 15:00:00 -0000

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!

What’s the deal with Deel?

Thu, 01 May 2025 13:00:00 -0000

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).

Founders need prenups, too

Thu, 24 Apr 2025 18:00:00 -0000

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.

Imposter syndrome is due for a rebrand

Thu, 17 Apr 2025 13:00:00 -0000

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…

The bull case for domestic manufacturing

Thu, 10 Apr 2025 16:49:48 -0000

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.

Battle of the startup cities

Thu, 03 Apr 2025 14:15:10 -0000

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.

Does anyone care about bad behavior anymore?

Thu, 27 Mar 2025 16:41:44 -0000

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.

To early exercise or not to early exercise

Wed, 19 Mar 2025 17:43:42 -0000

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.

The case for a product review renaissance

Thu, 13 Mar 2025 15:37:48 -0000

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.

Are SPVs for chumps?

Thu, 06 Mar 2025 20:30:16 -0000

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.

Why are all the VCs building personal brands?

Thu, 27 Feb 2025 19:10:52 -0000

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.