In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year.
Featuring:
David Rubenstein (co-founder of Carlyle)
Yamini Rangan (CEO of HubSpot)
Ben Chestnut (co-founder of Mailchimp)
Winston Weinberg (co-founder and CEO of Harvey)
Garrett Lord (co-founder of Handshake)
Aidan Gomez (co-founder and CEO of Cohere)
Michelle Zatlyn (co-founder of Cloudflare)
Evan Spiegel (co-founder and CEO of Snap)
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Email: grit@kleinerperkins.com
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Learn more about Kleiner Perkins: https://www.kleinerperkins.com/
What happens when AI becomes your most influential referrer?
As consumers turn to ChatGPT for answers, James Cadwallader and his team at Profound help brands like Eight Sleep and MongoDB gain visibility and leverage inside AI models.
On this episode of Grit, he explains why brand narrative has shifted away from content, and why Profound is scaling globally ahead of traditional SaaS timelines.
Guest: James Cadwallader, co-founder and CEO of Profound and Ilya Fushman, partner at Kleiner Perkins
Connect with James Cadwallader
X: https://x.com/thejamescad?lang=en
LinkedIn: https://www.linkedin.com/in/jsca/
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X: https://x.com/ilyaf
LinkedIn: https://www.linkedin.com/in/ilyafushman/
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X: https://x.com/Joubinmir
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Email: grit@kleinerperkins.com
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Learn more about Kleiner Perkins: https://www.kleinerperkins.com/
Turning down a $3B offer from Facebook is a bold move for any young CEO.
Evan Spiegel shares how Snap’s early dream was to stay independent and give its community an authentic voice, a bet that proved right.
He also explains why they are now doubling down on AR glasses and why the anxiety around AI deserves far more attention from tech leaders.
Guest: Evan Spiegel, co-founder and CEO of Snap Inc. and Bing Gordon, Advisor at Kleiner Perkins
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X:https://x.com/evanspiegel?lang=en
LinkedIn:https://www.linkedin.com/in/evan-spiegel/
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LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins:https://www.kleinerperkins.com/
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 enterprise revenue leaders.
Stepping into the host role, Mamoon Hamid joins Joubin to talk about his transition from sales leader to founder, how Roadrunner came together, and why it became our first incubation since Glean.
Roadrunner is hiring! Check them out: https://www.roadrunner.ai/
Guest: Joubin Mirzadegan, Partner, Kleiner Perkins
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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 regain control in an AI driven internet.
Guest: Michelle Zatlyn, co-founder and President of Cloudflare
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Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
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
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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 race among AI labs is really unfolding.
Guest: Aidan Gomez, co-founder and CEO of Cohere
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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 Wall Street.
Guest: Howard Lerman, co-founder and former CEO of Yext, and founder and CEO of Roam
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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 that give you energy.”
Guest: Dan O’Connell, CEO of Front
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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.
Guest: Mati Staniszewski, co-founder and CEO of ElevenLabs
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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 Riparbelli, CEO and co-founder of Synthesia and Josh Coyne, Partner at Kleiner Perkins
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LinkedIn: https://www.linkedin.com/in/victorriparbelli/
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LinkedIn: https://www.linkedin.com/in/joshuacoyne/
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LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins:https://www.kleinerperkins.com/
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.
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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 Snow, revealing how they built Snowflake’s ‘go-to-market engine’ and fostered a customer-first culture across every function.
Guests: Chris Degnan, former CRO and advisor to the CEO at Snowflake, and Denise Persson, CMO at Snowflake.
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Learn more about Kleiner Perkins:https://www.kleinerperkins.com/
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, and how a wake-up call led him to found Udacity to truly democratize higher education.
Guest: Sebastian Thrun, CEO of Stealth Startup, founder of Google X and Udacity
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Email: grit@kleinerperkins.com
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.
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:
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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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