CRO Obsidian Security, Bob Kruse: Building a Winning Sales Culture

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 DropboxChapters:00:00 Trailer00:52 Introduction01:35 Towards full autonomy16:20 Coming back to school21:45 Golden ticket to California25:23 No one’s born a CEO28:15 Y Combinator and a co-founder37:53 The craft of being a great CEO53:41 Metabolizing the stress1:10:14 Tactical advices and frameworks1:27:48 Who Dropbox is hiring1:29:35 What “grit” means to Drew1:32:10 OutroLinks:Connect with DrewXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

25 Aug 1h 32min

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 PerkinsConnect with Dan Lee: XLinkedInConnect with Leigh Marie BraswellXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

18 Aug 58min

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 GrammarlyConnect with ShishirXLinkedInChapters: 00:00 Trailer01:24 Introduction02:09 Zoo vs safari12:02 A TV ahead of its time21:25 Product decisions31:25 The data behind the algorithm37:26 The AI native productivity suite48:06 Agents are digital humans57:55 Pressure trade-off1:12:50 Insulated from judgment1:25:19 Who Grammarly is hiring1:25:51 What “grit” means to Shishir1:29:30 OutroMentioned 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 GrossConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

11 Aug 1h 29min

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 NotionMentioned 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, SlackConnect with Ivan ZhaoXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

4 Aug 1h 28min

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 TripAdvisorChapters:(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) OutroMentioned 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 GeminiLinks:Connect with SteveXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

28 Jul 1h 12min

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.Connect with Garrett LordXLinkedInConnect with JoubinXLinkedInEmailConnect with MamoonXLinkedInLearn more about Kleiner Perkins

21 Jul 1h 2min

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.Links:Connect with ZachXLinkedInConnect with JoubinXLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

14 Jul 1h 4min

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)Connect with Joubin:- LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/ - X:  https://x.com/Joubinmir Email: grit@kleinerperkins.comLearn more about Kleiner Perkins: https://www.kleinerperkins.com

7 Jul 54min