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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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 

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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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