Guest: Sal Khan, founder of Khan Academy AI is poised to change nearly every business, but few are changing as quickly as education. And Sal Khan, who has spend more than a decade manually creating more than 7,000 educational videos, says that’s a good thing. He’s encouraged Khan Academy to focus on “disrupt[ing] ourselves ... more than almost any …

Guest: Matt MacInnis, COO of Rippling One of the most important things a non-founder can do, says Rippling COO Matt MacInnis, is to learn how to operate in the context of the company they’re joining. His CEO, Parker Conrad, “spikes” in certain skill areas, and the rest of the executive team needs to maximize his ability to thrive while “taking care…

Guest: Jason Kilar, former CEO & co-founder of Hulu and former CEO of WarnerMedia When Jason Kilar was a child, he was obsessed with Walt Disney — not just as a filmmaker or the creator of Disneyland, but as an entrepreneur. He started his career at the Walt Disney Company (where else?) but then got his first opportunity to help build something new…

Guests: Joe Thomas, CEO and co-founder of Loom; and Ilya Fushman, partner at Kleiner Perkins Loom CEO Joe Thomas had a lot of things to think about before he sold his company to Atlassian for $975 million: The impact an acquisition might have on the product, how to keep the Loom brand alive, the risk of remaining independent... but it wasn’t until …

Guest: Rony Abovitz, founder & CEO of SynthBee SynthBee CEO Rony Abovitz grew up “really believing” in Star Wars and the idea that there could be benevolent, artificially intelligent beings like R2-D2 and C-3PO. “It wasn't a dystopian vision of the future,” he says. “It wasn't HAL from 2001. It wasn't the Terminator. It wasn't Skynet. It was this k…

Guest: Sebastian Siemiatkowski, CEO and co-founder of Klarna Living and working in Stockholm, Klarna CEO Sebastian Siemiatkowski thinks a lot about how he’s perceived in Silicon Valley: “I feel like here I am, I am the small, country cousin from Sweden.” And on top of that, he knew that someone like Sam Altman wouldn’t initially think of a European…

Guest: Kyle Hanslovan, CEO & co-founder of Huntress; and Ev Randle, partner at Kleiner Perkins Talk is cheap, says Huntress CEO Kyle Hanslovan: “I learned real early on that integrity is like one of the very few things, if not the only thing, you can't buy.” En route to Huntress’ current status as a $1.5 billion firm with $100 million in ARR, he to…

Guest: Mark Fields, former president & CEO of Ford Motor Company and chairperson at Planview In 2005, Mark Fields was asked to run the Americas for the Ford Motor Company, a role he would serve in for 7 years, later becoming COO and then CEO. His wife and kids were used to relocating for Mark’s job, but had just put down roots in Florida. He told t…

Guest: Jack Conte, CEO & co-founder of Patreon For many YouTube video creators, getting millions of views on your videos may seem like the goal. But when Jack Conte and his wife Nataly Dawn became YouTube stars through their band Pomplamoose, they didn’t automatically find gold at the end of the rainbow. “You check your ad revenue and you make 48 b…

Guest: Mark Pincus, founder & chairman of Zynga, and managing member & co-founder of Reinvent Capital Before Zynga and Facebook made social gaming mainstream, the video game industry was “extreme on this being about art and crafting,” recalls Zynga founder Mark Pincus. He believes his winning instinct was the realization that games were “at least 5…

Guest: RJ Scaringe, CEO and Founder of Rivian “I’m very comfortable with things not being in their end state,” says Rivian CEO and founder RJ Scaringe. The company’s challenging mission — to help make 100% of the world’s cars electric — will take a long time, and a lot of willingness to build the metaphorical plane in midair. As Rivian has grown fr…

Guest: Sridhar Ramaswamy, CEO of Snowflake “People underestimate what it is to go through a complete reset,” says Snowflake CEO Sridhar Ramaswamy. And he knows it: After an incredible 15-year run at Google, he started over from zero with an AI search startup, Neeva. And in hindsight, he regrets not trying to port over more of the skills that had ma…

Guest: James Freeman, Founder and Former CEO of Blue Bottle Coffee In the six or so years since he sold his last shares of Blue Bottle Coffee to Nestlé, James Freeman has had a lot of time to ruminate — about how he succeeded in creating a unique café experience, and also the ways he failed his workers as a manager. But he’s already thinking about …

Guest: John Hanke, CEO of Niantic When Pokémon Go launched, Niantic CEO John Hanke was enjoying a tranquil walk through a bamboo forest near Kyoto with his son. When he got back, it was all hands on deck: Building on a platform Niantic had developed for its previous game, Ingress, Pokémon Go was a runaway success story, earning $100 million dollars…

Guest: Mark McLaughlin, chairman of the board at Qualcomm When he was 24, Mark McLaughlin thought his career was over. Since childhood, he had dreamed of attending West Point and joining the Army, but a helicopter crash left him unable to serve, with a medical discharge. However, the crash also let him stay closer to his then-girlfriend Karen. They…

Guest: David Risher, CEO of Lyft David Risher can measure his career in phone calls, from the one that introduced him to Jeff Bezos in 1995, to the call from the Lyft board in 2023, asking him to vie for the CEO job. But initially, he believed his life’s legacy might be the nonprofit Worldreader, which has brought books to more than 22 million read…

Guests: Vipul Ved Prakash, CEO and co-founder of Together AI; and Bucky Moore, partner at Kleiner Perkins No one knows for sure whether the future of AI will be driven more by research labs and AI-native companies, or by enterprises applying the technology to their own data sets. But one thing is for sure, says Together AI CEO and co-founder Vipul …

Guest: Andrew Bialecki, CEO of Klaviyo Whenever the marketing platform Klaviyo is hiring, says CEO Andrew Bialecki, “we sort of don't care so much what skills you have.” Instead, the company looks for “high slope” individuals who are curious and able to continually learn new things. “A big turnoff for me is [when] somebody says, ‘Oh, well, I was ne…

Guest: Niraj Shah, CEO and co-founder of Wayfair Wayfair CEO Niraj Shah caught the entrepreneurship bug in his mid-20s, when he and his longtime co-founder Steve Conine sold their first company just a few years out of college. They left the acquirer and independently realized “we absolutely wanted to start something else,” Niraj recalls. “Once you’…

Guest: Jay Chaudhry, CEO, chairman, and founder of Zscaler Much of the media coverage of Zscaler CEO Jay Chaudhry is quick to identify him as the wealthiest Indian-American person, with a net worth of $10.8 billion. But to hear Jay himself tell it, that number has never been very important to him: “My family had no money,” he says of his childhood …

Guest: Bill Magnuson, CEO and co-founder of Braze The deployment of smartphones around the world was more impactful than any other technology to date, says Braze CEO Bill Magnuson — and that has big implications for emerging fields like generative AI. “If we get to the point where they [LLMs] really can be useful, human-like companions ... they wil…

Guest: Clara Shih, CEO of Salesforce AI In 2020, Clara Shih quit Hearsay, the company she founded and ran for 11 years; in hindsight, she says “I probably should have quit a little bit sooner.” But at the time, she cared a lot — too much — about what everyone else thought. “There's a lot of guilt around leaving initially and feeling bad for feeling…

Guest: Marissa Mayer, CEO and Founder of Sunshine and former CEO of Yahoo When Marissa Mayer was first hired as the CEO of Yahoo, the company had lost nearly a quarter of its workforce in the preceding six months. Early on, she was chatting with employees in the cafeteria and one of them got her attention by smacking her tray. “Is it go time?” he a…

Guest: Sarah Friar, former CEO of Nextdoor Sarah Friar has worked with some of the top leaders in Silicon Valley, including Salesforce CEO Marc Benioff, Walmart CEO Doug McMillon, Block CEO Jack Dorsey, and most recently Nextdoor founder Nirav Tolia, who just replaced her as CEO in May. And one of the things that sets top performers apart from the …

Guest: Stanislav Vishnevskiy, CTO and co-founder of Discord For many years, the conventional wisdom was the gaming was not social because it was something you usually did at home. “But people who play games are often the most social,” says Discord CTO Stanislav Vishnevskiy. “They’re spending 10, 20 hours with other people online, hanging out.” As a…

Guest: Eoghan McCabe, CEO, Chairman, and Co-Founder of Intercom “We are not ready for the degree to which our world is going to change,” says Intercom CEO Eoghan McCabe, “in insane and incredible ways.” When he co-founded the company in 2011, the Irish-born entrepreneur was making it easier for companies to offer human customer service to their cus…

Guest: Mark Cuban, co-founder of Cost Plus Drugs and costar, Shark Tank “I just love to compete,” says Mark Cuban. “And the day I stop is the day I’m dead.” Previously the co-founder of MicroSolutions and Broadcast.com, Cuban is probably best known to the public today for competing with the likes of Daymond John and Barbara Corcoran on the reality …

Guest: Taylor Francis, co-founder of Watershed One day when he was 13, Taylor Francis walked out of the movie theater, and he was pissed off. He had just seen Al Gore’s documentary An Inconvenient Truth and internalized a “generational call to arms, that my parents had screwed our generation” by causing the climate crisis, he says. 14 years later, …

Guests: Victor Riparbelli, CEO and co-founder of Synthesia; and Josh Coyne, partner at Kleiner Perkins When Victor Riparbelli wants to learn something, he’ll start with a YouTube video or a podcast: “I maybe buy the book on Amazon as like the fifth step,” the Synthesia CEO says. His company is trying to change the text-first (or text-only) way info…

Guest: Kat Cole, COO of Athletic Greens You can’t make smart decisions if you don’t know the truth — the “true truth,” as Athletic Greens COO Kat Cole puts it. “As you get bigger and you have success, innovator’s dilemma, you end up talking to yourself instead of really being rooted in what’s going on.” That’s why she has embraced the anxiety of th…

Guest: Anne Raimondi, COO and Head of Business at Asana Asana COO Anne Raimondi feels pressure to perform in her job “every day, all the time.” But that pressure doesn’t come from her fellow executives; she imposes it on herself, trying to think carefully about how much each of her decisions will impact her team. “I have a lot of privilege and choi…

Guest: Sanjay Beri, CEO and Founder of Netskope “You can be waiting your whole life to do something, and then your life’s over,” says Sanjay Beri. After nine years at Juniper Networks, he left his comfortable job, moved his family to a house with a pricier mortgage, and launched the cloud security firm Netskope. His entrepreneurial story would make…

Guest: Scott McNealy, former CEO and co-founder of Sun Microsystems & co-founder of Curriki Scott McNealy never wanted to be CEO of Sun, and in his 22-year tenure before selling to Oracle, he knows there were times he failed to execute, or to rein in the once-iconic Silicon Valley firm’s worst impulses. But like his pro golfer son, Maverick, Scott …

Guest: Jyoti Bansal, CEO and co-founder of Harness Cisco bought Jyoti Bansal’s first company AppDynamics for $3.7 billion, making him a very wealthy man. But after two African safaris, a week of Michelin-starred meals in Tokyo, and more adventures all around the world, he realized that spending his money didn’t truly make him happy. After some soul…

Guest: Clint Sharp, CEO and co-founder of Cribl New employees are joining the remote data platform Cribl every week, and as the staff grows, CEO Clint Sharp has noticed a problem: He can’t file a bug report without a lot of caveats. When there were a handful of users, no one would bat an eye at the CEO posting a bug on Slack, but now he has had to …

Guest: Glen Tullman, CEO of Transcarent Before he was CEO of Transcarent, Glen Tullman presided over the biggest digital health merger of all time: His previous company Livongo was acquired in 2020 by Teledoc for $18.5 billion. Over his decades of experience in health tech, he has developed saying: Hire low, fire high. When one of his friends was o…

Guest: Filip Kaliszan, CEO and co-founder of Verkada Great founders try to grow personally at least as fast as their companies do — but sometimes, says Verkada CEO Filip Kaliszan, that’s just not possible. By the time the company had about 200 employees, he says, “the scale of the business and the rate of the growth of the business ... outpaced my …

Guest: Wade Foster, CEO and co-founder of Zapier When Wade Foster and his co-founders launched Zapier, he was 24, and doubted himself constantly. He consulted mentors like Paul Graham and Jay Simons, studied entrepreneurs like Jeff Bezos and Steve Jobs, and also took inspiration from an unlikely source: Actor and martial artist Bruce Lee. “[He] had…

Guest: Kim Scott, author of Radical Candor: Be a Kickass Boss Without Losing Your Humanity and Radical Respect: How To Work Together Better After her first management book Radical Candor became a worldwide bestseller, Kim Scott found herself giving talks to all kinds of companies about how they could apply her advice and build a stronger, kinder cu…

Guest: Daniela Amodei, President and co-founder of Anthropic With a reported valuation of as much as $18 billion, Anthropic has the resources to be one of the dominant AI companies in Silicon Valley; however, it was conceived as a public benefit corporation and always tries to strike a balance between hypergrowth and responsibility. Anthropic’s fla…

Guest: Dev Ittycheria, CEO and President of MongoDB When you think about who you were and the decisions you made two, or four, or eight years ago ... how do you feel? Dev Ittycheria, the President and CEO of MongoDB, says he’s embarrassed about certain things he did — and that’s a good thing. “If you’re not [embarrassed], that means you’re not real…

Guest: Frank Slootman, CEO and Chairman of Snowflake and author of Amp It Up Snowflake CEO Frank Slootman doesn’t recall a time in his childhood where new achievements were celebrated — because, according to his father, putting everything into your work and “leaving it all on the field” was the only choice. “The problem with it,” Frank says, is tha…

Guest: Jason Kelly, CEO and co-founder of Ginkgo Bioworks Almost everyone in the second generation of biotechnology entrepreneurs, says Ginkgo Bioworks CEO Jason Kelly, works in that field because of one thing: Jurassic Park. The Michael Crichton novel-turned-Steven Spielberg movie captured both the wonder and beauty of bioengineering, and the chal…

Guest: John McMahon, author of The Qualified Sales Leader: Proven Lessons from a Five Time CRO A hell of a lot of people work in sales. But until recently, says five-time CRO and The Qualified Sales Leader author John McMahon, it was rare for colleges and universities to offer a sales degree. Salespeople had to learn on the job from experienced coa…

Guest: Angela Duckworth, professor at the University of Pennsylvania and author of Grit: The Power of Passion and Perseverance “There’s got to be a cost” when you pursue your passions, says University of Pennsylvania professor Angela Duckworth; in fact, the word “passion” comes from the Latin word for “suffering.” But that doesn’t mean that gritty …

Guest: David Cancel, founder and former CEO of Drift; founder of Rey After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had alread…

Guest: John Doerr, chairman of Kleiner Perkins After Kleiner Perkins chairman John Doerr first invested in Google — $12.8 million for 13 percent of the company — he told co-founders Larry Page and Sergey Brin that they needed to hire a CEO to help them build the business. After they took meetings with a variety of successful tech execs, they came b…

Guest: Shlomo Kramer, founder and CEO of Cato Networks Shlomo Kramer has founded three companies to date — Check Point, Imperva, and most recently Cato Networks — and taken the first two public, with plans to do the same with Cato. By any measure, he is a successful entrepreneur, but he defines “success” as “a burden you need to shake off every day…

Guest: Arvind Jain, Founder and CEO of Glean, and Mamoon Hamid, partner at Kleiner Perkins “I’m an engineer, so I have doubts about everything,” says Glean founder and CEO Arvind Jain. Well ... almost everything. Since launching Glean in 2019, he has held to the belief that “all of us are going to have really powerful AI assistants” in the future. …

Guest: Scott Cutler, CEO of StockX What’s the point of climbing a mountain, or heli-skiing in the Swiss Alps, or biking in the Tour de France? StockX CEO Scott Cutler has done all three, and for him, the answer is momentary perspective. “When you’re descending, you don’t see, but you know what is above,” he says. “You have experienced and have seen…