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/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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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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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 at scale.
Guest: Steve Kaufer, co-founder of TripAdvisor
Chapters:
(00:00) Trailer
(00:45) Introduction
(01:32) Early days of Tripadvisor
(08:14) Catching the startup bug
(18:42) Luck and timing
(26:54) $200M: a combo of money and risk
(37:37) I love creating stuff
(40:45) Hardest part of being a public CEO
(46:21) Never let a good crisis go to waste
(51:54) An average traveler
(55:49) Social proof vs artificial intelligence
(1:02:59) Back in the saddle
(1:09:54) Not for the faint of heart
(1:12:16) What “grit” means to Steve
(1:12:31) Outro
Mentioned in this episode: Google, Expedia Group, Barry Diller, Interactive Corporation (IAC), Uber, Dara Khosrowshahi, OpenAI ChatGPT, IMDb, CJ Affiliate (Commission Junction), Amazon, Google Chrome, Give Freely, Honey, Rakuten, Macy’s, American Cancer Society, Google Gemini
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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, enabling experts to train real-world AI systems. He explains how owning verified domain talent has become their core strategic edge, bypassing middlemen and turning a decade of trust into lasting advantage.
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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 was harder than expected, and how Plaid is navigating the shift from startup to staple—while staying obsessed with the end user.
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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)
• Yamini Rangan (HubSpot CEO)
• Chris Urmson (Aurora CEO)
• Varun Mohan (Windsurf Co-founder and CEO)
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- LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/
- X: https://x.com/Joubinmir
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins: https://www.kleinerperkins.com
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 Murphy, CEO & Co-Founder of Imprint
Chapters:
00:00 Trailer
00:48 Introduction
01:30 Actualizing the dream
08:37 Imprint
11:37 Partnerships are massive
16:48 Understand the market
18:42 “Get more, spend more” tradeoffs
23:57 Fishing in the wrong ponds
31:32 Can’t skip work
32:43 Exciting and scary
34:56 Pride and ownership
46:50 The way you spend your day
50:20 New technologies
54:51 Who Imprint is hiring
54:59 What “grit” means to Daragh
55:34 Outro
Mentioned in this episode: Figma, Rippling, H-E-B Grocery Company, LP, Barclays US, IBM, Coinbase, Charlie Munger, Instagram, Hamptons, Google, Nick Huber, Ribbit, Ireland, WeWork, Adam Kim, Amazon, Shopify, Tobias Lütke, Duolingo, Parker Conrad
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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 auto-debugging code and closing security gaps.
Guest: Bill Staples, CEO of GitLab
Chapters:
00:00 Trailer
00:42 Introduction
02:34 True joy in life
08:16 Winning teams
13:53 When the energy isn’t there
18:00 Super ambitious
21:01 It’s not just technology
29:27 Elevating quality and standard
41:36 Lifelong collaborator
51:22 Competent intelligence
54:22 Structuring goals and time
1:03:59 Who GitLab is hiring
1:04:17 What “grit” means to Bill
1:04:54 Outro
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