Grit

• From India to Silicon Valley: The Jay Chaudhry & Zscaler Story

  Before Zscaler was a $32B cloud security giant, it was just 10 engineers—half in Bangalore, half in a borrowed U.S. office.As founder and CEO of Zscaler, Jay Chaudhry bet $50M of his own money on one radical idea: secure the internet in the cloud.Born in a Himalayan village with no electricity, he built Zscaler into one of the world’s top cybersecurity giants.In this episode, Jay breaks down why 50% of the Fortune 500 trusts Zscaler, why he still interviews candidates, and how he’s incubating the company’s next big AI bet.Chapters:00:00 Trailer00:42 Introduction01:21 His fifth company04:26 Entrepreneurs’ existential fear10:53 Customer engagement and new innovations12:46 No private jets, no business class19:34 “I never used money”23:38 Born and raised in India26:17 Hiring legends30:35 Walking on water35:09 “Dolphining”39:55 Areas of weakness42:11 Passionate even on the weekends44:56 Work during roller coasters47:35 The weight of the world is on your shoulders49:21 Leveraging AI56:20 OutroMentioned in this episode: Elon Musk, Microsoft, Bill Gates, BlackBerry, Steve Ballmer, Satya Nadella, Hewlett-Packard (HP), IBM, John Fellows Akers, Steve Jobs, NeXT, Inc., Linux, Cisco, United Airlines, San Francisco International Airport, Sundar Pichai, Ravi Mhatre, Lightspeed Venture Partners, Six Flags, AI (artificial intelligence), securityLinks:Connect with JayLinkedInConnect with JoubinXLinkedInEmail: [email protected] Learn more about Kleiner Perkins

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• The Unlikely Path to Building a Billion-Dollar Gov Tech Company | Zac Bookman

  Guest: Zac Bookman, CEO and Co-Founder of OpenGovThirteen years after co-founding the government transparency startup OpenGov, Zac Bookman is still finding ways to surprise people. In 2024, Cox Enterprises bought the company for $1.8 billion — but as far as Zac is concerned, “we’re just getting started.”“ I left the vast majority of my net worth in the company,” he says. “So I'm a believer. I'm all in.”The mission of powering “more effective and accountable government” has been stable since OpenGov’s earliest days, and that mission has informed everything from hiring to M&A to the decision to sell. “These people buy and don't sell,” Zac said of Cox. “They're all in on the mission. And they're all in on taking care of employees. So I see a triple win: A win for employees, win for the investors, win for the customers, maybe a quadruple win for me and the management.”Chapters:(01:46) - OpenGov’s mission (04:34) - Shrinking the product-market fit (07:34) - Super misson driven (08:59) - Why OpenGov almost shut down (13:08) - Zac’s early career (16:16) - Picking (and losing) a CTO (22:50) - Growing upside-down (25:29) - The SPAC backstabber (31:26) - Why Zac didn’t get fired (33:24) - Selling in 2024 (37:04) - Growth by acquisition (42:31) - John Chambers and PMF (49:32) - Zac’s cross-country bike ride (56:25) - Expectations vs. reality (58:57) - The coup attempt (01:01:59) - Tiring work (01:05:47) - Going to the White House (01:09:40) - DOGE & disrespect (01:12:54) - “We’re just getting started” (01:14:18) - Who OpenGov is hiring (and where) (01:15:13) - What “grit” means to Zac Mentioned in this episode: Joe Lonsdale, Cox Enterprises, OpenAI, the Department of Government Efficiency, Workday, H.R. McMaster, Stanford University, Formation 8, 8VC, the National Academy of Sciences, the Stanford Review, Kamala Harris, Marc Andreessen, Balaji Srinivasan, Coinbase, Earn, Ben Horowitz, Facebook, Steve Laughlin, Cisco, Laurene Powell Jobs, Glynn Capital, Acme, Allen & Company, Harry You, Joe Tucci, EMC, Bill Green, Accenture, Tyler Technologies, HP, Josh Kushner, GTY Technology Holdings, John Keker, Palantir, CKAN, Oracle, Kevin McCarthy, The American Technology Council Summit, Jeff Bezos, Tim Cook, Satya Nadella, Pat Gelsinger, Donald Trump, Jared Kushner, Elon Musk, Bill Clinton, and Al Gore.Links:Connect with ZacLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

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• Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit

  Guest: Ben Chestnut, Former CEO and Co-Founder of MailchimpIf you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog. When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over. After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head."“After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.”Mentioned in this episode: Intuit, Wolt, DoorDash, LinkedIn, Dan Kurzius, Salesforce, ExactTarget, Pardot, Constant Contact, Rackspace, Free by Chris Anderson, Wired Magazine, Charles Hudson, the Freemium Summit, Drew Houston, Dropbox, Evernote, Phil Libin, TechCrunch, Brian Kane, Catalyst Partners, Georgia Pacific, Scott Cook, Bing Gordon, Vinay Hiremath, Loom, Joe Thomas, Caltrain, Flickr, Saturday Night Live, Droga5, Cannes Film Festival, Strava, Twitter, LinkedIn, Nvidia, Glean, Rubrik, Amazon AWS, and Mechnical Turk.Links:Connect with BenLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner Perkins

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• Meet the Man Who’s Making Supersonic Flight Possible Again | Blake Scholl

  Guest: Blake Scholl, Founder & CEO of Boom Supersonic“Passion and drive trumps knowledge and experience,” says Boom Supersonic CEO Blake Scholl. Long before he was running Boom — which earlier this year successfully tested the world’s first privately-developed supersonic jet — he was enabling “the world’s most obnoxious spam cannon” at Groupon, or designing a barcode-scanning game for retail shoppers.But eventually, Blake found the courage to be more audacious and do something closer to his lifelong love of aviation. He began educating himself about things he had never thought to learn, and tapping his LinkedIn network to get intros to the smartest people in the industry. “If you imagine yourself on like the day of IPO, 99 percent of what you needed to know to get to that day, you didn't know on day one,” he says. “So, why not take 99 percent to 99.5 percent, and work on the thing you really want to exist, even if you don't know anything about it yet?”Chapters: (01:07) - Blake on Boom’s beginnings (01:52) - Breaking the sound barrier (05:23) - Concorde’s legacy (09:36) - Navigating regulations (12:08) - Boomless supersonic flight (16:48) - The test flight (20:11) - Day-of nervousness (24:26) - Carrying passengers (26:55) - Cost & wi-fi (30:19) - “No middle seats” (32:35) - Hard tech (36:48) - What if Apple made a plane? (39:08) - Blake’s career journey (43:29) - The risk of failure (49:12) - Finding the courage (52:49) - Balancing life with Boom (56:42) - Learning how to build a jet (01:00:20) - The power of LinkedIn (01:02:38) - Y Combinator Demo Day (01:08:24) - Richard Branson (01:11:38) - Dividing yourself (01:14:19) - Being a focused dad (01:20:05) - Exuberance vs. fear (01:24:15) - Hiring slowly (01:27:17) - What “grit” means to Blake Mentioned in this episode: Chuck Yeager, ChatGPT, the Apollo program, Elon Musk, SpaceX and Falcon 1, Boom Overture, Starlink, Boeing, Airbus, iPhone, Jony Ive, Uber, Airbnb, Anduril, United Airlines, American Airlines, Eclipse Aviation, Tesla, Scott Kirby, Mike Leskinen, Inktomi, Yahoo!, Amazon, Pelago, Google Ads, Kima Labs, Barcode Hero, Groupon, iPad, Eric Schmidt, Steve Jobs, Khan Academy, Sam Altman, Loopt, Virgin Atlantic, Paul Graham, Michael Seibel, Ashlee Vance, Bloomberg, Hacker News, Jared Friedman, Sen. Mark Kelly, SV Angel, Ron Conway, Virgin Galactic, Lockheed Martin, Gulfstream, Jeff Bezos, Jeff Holden, and How It’s Made.Links:Connect with BlakeTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

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• #232 CEO NetApp, George Kurian: New Chapters

  Guest: George Kurian, CEO of NetAppFor almost 10 years, George Kurian has been CEO of the data infrastructure firm NetApp, overseeing its pivot to cloud services. After he  took the job — a surprise promotion dropped on him just days before it was announced — he had to learn on the job how the job could be.“ There are a lot more stakeholders that a CEO has to deal with than a chief product officer,” George says, referring to his previous role. “There's also a lot more external commitment ... It was a really all-consuming effort to get the company turned around.”He said the CEO job can be “fairly lonely” because you may want to be peers or friends with your team and your board — but in fact, they are sometimes your subordinates and your superiors, respectively.“ We wouldn't be here without others having contributed significantly on the journey,” George says. “[But] there are times when you have to step back and say, ‘I see a pattern that my team is not seeing,’ or ‘Do I think that we can do a better job than we are doing?’”Chapters:(01:10) - Commuting to Sunnyvale (04:49) - Growing up in India (08:04) - Protect the child (09:33) - Raising kids in Silicon Valley (12:44) - Money motivation (15:04) - NetApp’s renaissance (21:39) - Writing new chapters (23:15) - Culture shifts (26:38) - Coming to NetApp (29:41) - Surprise! You’re the CEO (32:41) - Making sacrifices (35:04) - Work vs. family tension (37:18) - Doubt & lonely decisions (42:38) - The data wave (45:27) - Enterprise AI (51:36) - Starting your own company (53:33) - Navigating difficulty (56:28) - Who NetApp is hiring (57:11) - What “grit” means to George Mentioned in this episode: EMC, OpenAI, DeepSeek, CalTrain, the San Francisco 49ers, Princeton University, Subway, Vons, Thomas Kurian, Google Cloud, Stanford University, Brian Cox, Oliver Jay, the Quakers, Jay Chaudhry, zScaler, Manmohan Singh, Oracle, IBM, Sun, Amazon, Microsoft, Glean, Kobe Bryant, Steph Curry, McKinsey, Akamai, Cisco, Gwen McDonald, and the San Francisco Friends School.Links:Connect with GeorgeLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

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