What kind of founder builds a billion-dollar company around something anyone can use for free?

Matt Mullenweg, co-founder of WordPress and CEO of Automattic, joins Joubin Mirzadegan to reflect on two decades of building the platform that now powers over 43% of all websites through cycles of doubt, decline, and reinvention.

He also shares how Automattic aligns employees with its mission to democratize publishing and commerce through paid sabbaticals and remote work.

Guest: Matt Mullenweg, co-founder of WordPress and founder and CEO of Automattic

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The apps and websites we use every day depend on systems most of us never see.

Jay Kreps joins Joubin Mirzadegan to share how Confluent became the ‘central nervous system’ for companies like Expedia and eBay, letting them respond to business operations instantly.

They also break down why the myth of AI-driven efficiency falls short, and why building truly transformative companies takes far longer than most people expect.
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Guest: Jay Kreps, Co-Founder & CEO of Confluent

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Can a no-code giant reinvent itself in the AI-native era?

This week on Grit, Airtable CEO Howie Liu shares what it means to “refound” a company, how speed comes from tearing up old playbooks, and why conversational AI is reshaping his product—and his company.

Guest: Howie Liu, Co-Founder & CEO of Airtable

Chapters:

00:00 Intro
01:04 First startup & YC
04:06 Salesforce acqui-hire
07:31 Life-changing exit at 22
11:07 Scaling too fast, layoffs
14:04 Sparks vs. coasting growth
19:33 Two years to launch
24:04 Could AI Build It Faster?
27:06 Vibe coding & AI startups
36:47 Everyone can build software
41:08 Refounding Airtable with AI
51:04 Sprint vs. marathon
58:15 Cap tables & control
01:03:29 Always be hiring
01:05:00 What grit means

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For Bill McDermott, work has never been just a job.

On this Labor Day rerun of Grit, first published Jan 9, 2023, the ServiceNow CEO reflects on what he learned from his earliest jobs and how he carried those lessons from a deli counter in Long Island to the boardroom of an $80B software company.

We cover:

• Why Bill bought a deli when he was in high school — and how he competed against 7-Eleven (04:00)
• Interviewing at Xerox and wanting it more than anyone else (08:17)
• Unwavering optimism and being a source of strength for others (12:34)
• How a love of work has shaped Bill as a person (16:44)
• Facing challenges and keeping a promise to his father (22:00)
• Enjoying the present and keeping an eye on the future (30:01)
• Leaving Xerox for Gartner and learning from a tough experience (33:29)
• Sloan Kettering and Father Michael Judge (39:22)
• Following the “original dream” vs. building something new at ServiceNow (44:59)
• Losing an eye and getting a pep talk from two Medal of Honor winners (51:15)
• Why Bill started and ended his book with quotes from two Kennedys (01:01:21)

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How do you win when your competitors are the biggest companies in the world?

This week on Grit, Dropbox co-founder and CEO Drew Houston retraces the path from a bus-stop prototype to competing head-on with Google, Apple, and Microsoft.

He explains why grit is “learning to run toward discomfort,” and the moments he realized founders keep going “for the love of the game.”

Guest: Drew Houston, Co-Founder & CEO of Dropbox

Chapters:

00:00 Trailer
00:52 Introduction
01:35 Towards full autonomy
16:20 Coming back to school
21:45 Golden ticket to California
25:23 No one’s born a CEO
28:15 Y Combinator and a co-founder
37:53 The craft of being a great CEO
53:41 Metabolizing the stress
1:10:14 Tactical advices and frameworks
1:27:48 Who Dropbox is hiring
1:29:35 What “grit” means to Drew
1:32:10 Outro

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Even with AI, sales still comes down to human connection.

This week on Grit, Dan Lee shares how Nooks automates busywork like research and dialing for thousands of sales teams, letting reps focus on the conversations that close deals.

He also shares his “do more with less” approach, why cold calls still convert, and how to maximize human impact alongside AI.

Guests: Dan Lee, CEO and Co-founder of Nooks and Leigh Marie Braswell, Partner at Kleiner Perkins

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What if your tools shared context like your team does?

This week on Grit, Shishir Mehrotra shares how the Coda and Grammarly collaboration unlocks context as a “superpower,” reflects on his early days at Google and YouTube, and hints at a future where tools anticipate intent and amplify how we work.

He also shares how this paves the way for agent-based workflows and AI-native communication, beginning with Superhuman’s email experience.

Guest: Shishir Mehrotra, co-founder of Coda and CEO of Grammarly

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Chapters:
00:00 Trailer
01:24 Introduction
02:09 Zoo vs safari
12:02 A TV ahead of its time
21:25 Product decisions
31:25 The data behind the algorithm
37:26 The AI native productivity suite
48:06 Agents are digital humans
57:55 Pressure trade-off
1:12:50 Insulated from judgment
1:25:19 Who Grammarly is hiring
1:25:51 What “grit” means to Shishir
1:29:30 Outro

Mentioned in this episode:
YouTube, Ray William Johnson, Spotify, Twitch, MTV, Chris Cox, Facebook, TikTok, Google TV, Centrata, Google Chrome, Android, Gmail, Microsoft, Super Bowl, Mosaic, Panasonic, Sony, Susan Wojcicki, Rishi Chandra, Apple TV, Amazon Firestick, Comcast, LoudCloud (Opsware), Quest Communications, AT&T Southwestern Bell, Salar Kamangar, Patrick Pichette, Eric Schmidt, OpenAI ChatGPT, Google Gemini, Mark Zuckerberg, Meta Platforms, Sundar Pichai, Larry Page, Sergey Brin, Hamilton, Reid Hoffman, Sam Altman, Tesla, Waymo, Airtable, Notion, Max Lytvyn, Alex Shevchenko, Superhuman, Duolingo, Luis von Ahn, Khan Academy, MrBeast, Facebook Messenger, Snap (Snapchat), WhatsApp, Google+, Meta LLaMa, Satya Nadella, Tim Cook, Daniel Gross

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Ivan Zhao joins Joubin Mirzadegan on Grit to break down how the company’s minimalist design became a strategic edge in a world overwhelmed by bloated software.

He shares why the AI agent still hasn’t arrived, and how Notion’s modular approach might be the closest thing to making it real.

Guest: Ivan Zhao, co-founder and CEO of Notion

Mentioned in this episode: Fuzzy Khosrowshahi, Airbnb, Sequoia Capital, Linear, Figma, Apple, Things, Microsoft, BMW, Lumiere, The Beatles, The Rolling Stones, Eric Clapton, Rippling, Matt MacInnis, Inkling, Steve Jobs, Douglas Engelbart, Alan Kay, Bill Gates, OpenAI ChatGPT, Y Combinator, Andrej Karpathy, Toby Schachman, Simon Last, Spotify, Slack

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