Grit

What does it take to go from advising founders to becoming one? On this week’s special Reverse Grit episode, we flip the script and put our Grit podcast host Joubin Mirzadegan in the guest seat. Joubin recently founded Roadrunner, where he is now co-founder & CEO. Roadrunner is building an AI‑native CPQ to modernize the quote‑to‑cash stack, drawing on years of conversations he’s had with enter...

Fifteen years in, it can still feel like “we’re just getting started.” Michelle Zatlyn , co-founder of Cloudflare, returns to Grit with Joubin Mirzadegan to share how Cloudflare secures the internet for millions, with a vision built to last generations. She also shares why staying close to reality and to customers becomes harder as success compounds, and how Cloudflare is helping content creators...

Screens have pulled families apart. Brynn Putnam set out to bring them back together with Board, the world’s ‘first face-to-face game console.’ On Grit, she tells Joubin Mirzadegan how every venture she’s built, including Mirror, started as a personal need, and how her true edge is the ability to strip an idea down to what actually matters. Guest: Brynn Putnam, founder and CEO of Board Connect wit...

How do companies like Salesforce and Dell scale intelligence across every cloud? Aidan Gomez, co-founder and CEO of Cohere, explains how they’re building AI that works across all enterprise systems and deploys anywhere, giving companies true flexibility and security. He joins Joubin Mirzadegan for a wide-ranging conversation on why synthetic data went from dismissed to indispensable, and how the r...

The hardest company to build is the one you start after you’ve already succeeded. After scaling Yext into a platform powering millions of businesses, Howard Lerman chose to start over with Roam, the “Office of the Future,” where humans and AI work side by side from anywhere. On Grit , he joins Joubin Mirzadegan to talk about the solitude of leadership and what happens when you stop building for Wa...

The hardest part of transformation is knowing what to let go of. Dan O’Connell , now leading Front as CEO and formerly on the board at Dialpad, joins Joubin Mirzadegan to explore the delicate balance between legacy and innovation as he leads a decade old company through the AI revolution. He also reflects on why courage and control can coexist in leadership, and what it means to “make decisions th...

Before AI became a buzzword, a few true believers were already building. Since early 2022, Mati Staniszewski and his team at ElevenLabs have been among them, working to create voices that “actually represent emotions.” He shares with Joubin Mirzadegan how voice AI is transforming diverse fields, from delivering personalized healthcare for different age groups to amplifying creativity in filmmaking...

What’s product-market fit like when you give people the power to do what they never thought was possible? On this rerun of Grit from April 2024, Victor Riparbelli, co-founder and CEO of Synthesia, shares how his platform gave billions a new way to create video without cameras, and explores a future where video and audio replace text as the primary way to share knowledge and content. Guests: Victor...

Make your product irresistible, and everything else will follow. That’s the philosophy of Grant Lee , co-founder and CEO of Gamma, an AI design platform with an 'anti-PowerPoint approach', used by over 50M people. This week on Grit , he also shares why enduring businesses aren’t one person shows, and how their deliberate hiring process shapes and strengthens company culture. Connect with Grant Lee...

Scaling a business globally comes down to leaders who align teams and drive them forward together. Snowflake serves over 12,000 customers, and early executives Chris Degnan and Denise Persson share how they scaled the company while keeping the unlikely pairing of sales and marketing perfectly aligned through hypergrowth. They join Joubin Mirzadegan to share insights from their new book, Make It Sn...

What does it take to reinvent entire industries, over and over again? This week on Grit, Sebastian Thrun, the “godfather” of self-driving cars and massive open online courses, reflects on a career pushing the boundaries of technology across mobility, education, and AI. With Joubin Mirzadegan, he shares why he believes autonomous driving could become the biggest lifesaving technology in history, an...

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 democrat...

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...

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...

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 (...

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-F...

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...

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, beginn...

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...

How did Tripadvisor become every traveler’s starting point? Steve Kaufer joins Joubin Mirzadegan on Grit to break down how Tripadvisor became the internet’s trusted travel companion, built on over a billion reviews and decades of trust. He also shares why early personalization fell short and how AI is finally doing what travel agents once did by understanding the traveler, but faster, smarter, and...

Guests: Garrett Lord, co-founder and CEO of Handshake; and Mamoon Hamid, partner at Kleiner Perkins. Handshake set out to democratize career opportunity. In the process, it unlocked something more: a high-trust expert network built on verified talent and earned trust. This week on Grit , Garrett Lord shares how what began as a platform for student job seekers is now partnering with leading labs, e...

Zach Perret saw a fintech explosion coming—and built the rails before it arrived. On this week’s Grit, the Plaid co-founder and CEO retraces his path from building tools for developers to linking the world’s largest banks, and how a failed $5.3B acquisition by Visa became a launchpad. He unpacks the pressure of operating in a tightly regulated industry, why rebuilding trust after the deal collapse...

Six leaders from across tech — from SaaS and semis to law and logistics — come together for our 250th episode milestone in this very special AI recap, where we unpack how new advances are transforming the way industries function, and how work gets done. Featuring: • Bret Taylor (Sierra Co-founder) • Winston Weinberg (Harvey Co-founder and CEO) • Matt Murphy (Marvell Technology Chairman and CEO) •...

Daragh Murphy is giving brands their own credit-card platform—no legacy bank required. On this week’s Grit, the Imprint co-founder and CEO traces the leap from being a junior lawyer to closing nine-figure card deals. He breaks down the hidden economics of credit-card loyalty, the discipline of treating capital “like the last dollar,” and how AI will slash risk-and-support costs. Guest : Daragh Mur...

Bill Staples has spent 30 years redefining how the world writes, ships, and secures code. On this week’s Grit, the GitLab CEO shares what it takes to lead a public, all-remote DevSecOps company trusted by more than half of the Fortune 100. He breaks down the discipline of managing energy instead of hours, why weekly operating cadences beat quarterly plans, and how AI will 10× software engineers by...