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 Trailer
00:42 Introduction
01:21 His fifth company
04:26 Entrepreneurs’ existential fear
10:53 Customer engagement and new innovations
12:46 No private jets, no business class
19:34 “I never used money”
23:38 Born and raised in India
26:17 Hiring legends
30:35 Walking on water
35:09 “Dolphining”
39:55 Areas of weakness
42:11 Passionate even on the weekends
44:56 Work during roller coasters
47:35 The weight of the world is on your shoulders
49:21 Leveraging AI
56:20 Outro

Mentioned 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), security

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Guest: Zac Bookman, CEO and Co-Founder of OpenGov

Thirteen 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

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.

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp

If 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.

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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

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.

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: George Kurian, CEO of NetApp

For 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

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.

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This episode was edited by Eric Johnson from LightningPod.fm

Guests: Winston Weinberg, CEO & co-founder of Harvey; and Ilya Fushman, partner at Kleiner Perkins

“If you think about pretty much any job out there in the world, we will have some sort of [AI] copilot,” says Kleiner Perkins partner Ilya Fushman. “The question is, who are the right folks to build it, and what’s their vision?”

For Harvey CEO & co-founder Winston Weinberg, the vision is clear: Silicon Valley cannot and should not try to disrupt the legal profession by automating the job of lawyers. Instead, he says, they need to have “respect for the industry” before designing AI solutions that speed up specific tasks.

“These industries are incredibly complex,” Winston says. “Legal is one of the oldest professions known to man. There are firms that are over a hundred years old. There are firms that are hundreds of years old, and having a brand that says, ‘We are partnering with the industry to transform it’ versus ‘We are just going to steamroll the industry’ is really important for us.”

Chapters:

• (01:16) - The zeitgeist switch

Mentioned in this episode: ChatGPT, the Fortune 500, Microsoft Copilot, Gabe Pereyra, Activision, Excel, Counsel AI Corporation, Suits, Harvard University, Netflix, Dell, O'Melveny & Myers, Hueston Hennigan, Meta, Reddit, Jason Kwon, Anthropic, Marissa Mayer, Eric Schmidt, Google, Larry Page, Sergey Brin, and Glean.

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: Miki Kuusi, head of international at Doordash + CEO & co-founder of Wolt + co-founder of Slush tech conference

Before Miki Kuusi launched the Finnish delivery startup Wolt, which DoorDash acquired in 2022, he wasn’t just another startup entrepreneur. From 2011 to 2015, Miki was the CEO of the hugely influential European tech conference Slush, which brings thousands of founders and VCs to Helsinki every winter.

 “You could argue that Slush was my university for things leading up to Wolt, and what I do today,” Miki says. “That's where I learned most of the core lessons that I put into action.” 

One thing he remembers thinking in those early days: Everything was going to be redefined by the internet.

“I just wanted to get a shot at building one of these services of the next hundred years,” he says. “And that was the driving motivator for me. If the driving motivator had been money, I don't think we would be here today.”

Chapters:

• (01:14) - Act 3

Mentioned in this episode: Tony Xu, Uber, Lyft, Uber Eats, Postmates, Delivery Hero, GrubHub, DeepSeek, OpenAI, Anthropic, Kees Koolen and Booking.com, 83North, Supercell, DashPass, Wolt+, Microsoft Excel, Amazon, Parker Conrad and Rippling, Andreeseen Horowitz, Fortnite, WhatsApp, Barry’s Bootcamp, and Slack.

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: Bobby Kotick, former CEO of Activision Blizzard; and Bing Gordon, Advisor at Kleiner Perkins

In 2020, when President Trump signed the executive order that would ban TikTok in the U.S., Bobby Kotick called his old friend Steven Mnuchin. The former Secretary of the Treasury told him that, if TikTok’s U.S. operations were to be sold to an American company, Microsoft would be the only bidder.

A couple calls later, he reached ByteDance founder and CEO Zhang Yiming, who said he’d rather sell to Bobby than Microsoft. Concerned about his ability to get the deal done solo, Bobby called Microsoft CEO Satya Nadella and offered to make a joint bid. 

Nadella declined, but added, “ if the deal doesn't get done, we should sit down and talk about us buying Activision.” TikTok currently remains Chinese-owned, but three years later, Microsoft paid $75 billion for Activision Blizzard.

Chapters:

• (01:16) - Forming Activision Blizzard

Mentioned in this episode: Vivendi, Bruce Hack and Arnaud de Puyfontaine, EA, Call of Duty, Bizarre Creations, Atari, Apple II, Commodore 64, Jean-Louis Gassée, Apple Lisa, Howard Lincoln, Philips, Magnavox Odyssey, Sutter Hill Ventures, Infocom and Zork, Toys-R-Us, Howard Hughes, E. Parry Thomas, Sun Valley, Thom Weisel, William Morris Endeavor, Guitar Hero, Davidson & Associates, Michael Morhaime, Allen Adham, World of Warcraft, Medal of Honor, Steven Spielberg, Michael Crichton, Chris Roberts, Overwatch, Tencent, Time Warner, Jeff Bewkes, Sheryl Sandberg, Lean In, Lina Khan, Samsung, Elon Musk, James L. Jones, UFC, E. Floyd Kvamme, Toy Story 2, Procter & Gamble, Ron Doornik, John Lasseter, Xerox PARC, Shigeru Miyamoto, Satoru Iwata, Goldeneye 007, James Bond, Barbara Broccoli, Oculus, Apple Vision Pro, Bill Gates, Steve Ballmer, Sam Altman, Mustafa Suleyman, Spotify, Candy Crush Saga, Disney, Phil Spencer, Clarence Avant and Motown Records. 

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: Nick Kokonas, co-founder of the Alinea Group and former CEO of Tock

As of October 1, 2024, Nick Kokonas is no longer an owner of the Alinea restaurant group, which he co-founded and ran for almost 20 years. When he bought a vineyard in Napa Valley prior to the exit, one of his sons remarked, “He's given up. Time to go out to pasture.”

Nick admits that the work ahead of him is “not the same” as the high-pressure world of a Michelin-starred restaurant in Chicago. But he’s started working with the magician Nate Staniforth on a new restaurant concept that will present diners with illusions and surprises over the course of a two-hour experience. 

“If you want to feel wonder and feel childlike again, go see a magician,” Nick says. “[But] there’s so much bad cultural baggage ... what we wanted to do was create an experience that is not really about magic.”

Chapters:

• (02:29) - Celebrity restauranteurs

Mentioned in this episode: Mike Gamson, Shaquille O’Neal, Jeff Kaplan, Steve Bernacki, Robin Anil, Grant Achatz, OpenTable, American Express, The Big Lebowski, The New York Times, eGullet, Gourmet Magazine, Roger Ebert, Eddie van Halen, Goodfellas, The Devil Wears Prada, Batman, the Chicago Bears, Madonna, Taylor Swift, Bavette’s and Brendan Sodikoff, Pablo Picasso, Chef’s Table, Google, Brian Fitzpatrick, Finding Real Magic, David Blaine, Mark Cuban, Mark Caro, Chicago Magazine, John Mariani, Cat Cora, Homaro Cantu, Dave Portnoy, Pete Wells, and Eric Asimov.

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This episode was edited by Eric Johnson from LightningPod.fm

Guest: Rick Smith, CEO & Founder of Axon (formerly TASER)

Being a founder-CEO is a “unique superpower,” says Axon’s Rick Smith: People like him get a longer leash from the board to try things that outside CEOs might not.

“My job is to push risk into the organization,” Rick says. “If there's a project with a 50 percent chance of success, a 50 percent chance of failure, but it's going to pay 100 to 1, any finance person will tell you, you should take that bet all day long.”

One of those bets was the transition from running a weapons company called TASER into a broader public safety firm called Axon, which makes cloud-supported body cameras fro police, tactical drones, AI records management software and more. “If we never have a product failure, then we're not taking risks anymore and we're going to end up getting disrupted,” Rick says.

Chapters:

• (01:09) - Tasers vs. guns

Mentioned in this episode: UnitedHealthcare and Brian Thompson, Harvard University, human-machine interfaces, Star Wars, Timecop, Star Trek, Jack Cover, Project Apollo, Ed Owen; the Bureau of Alcohol, Tobacco, and Firearms; Tom Smith, Rodney King, the Sharper Image, Steve Filmer, Phil Smith, Silicon Valley Bank, Emil Michael, Bob Kagle, Benchmark, Norwest Ventures, Molly Wuthrich, Josh Isner, The Terminator, Ferrari, Richard Branson, Burning Man, Steve Jobs, Brenda Smith, Hadi Partovi, Amazon AWS, Microsoft, DraftOne, Ambience Health, OpenAI, Mark Zuckerberg, Michael Brown, Computer Aided Dispatch, Elon Musk and SpaceX, and Luke Larson.

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This episode was edited by Eric Johnson from LightningPod.fm