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 information is conveyed at work, making AI avatar-narrated videos to replace documents like customer profiles and HR manuals. Victor says that as the...

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 the unknown, channeling what she doesn’t know about the market into productive questions for her team and her customers. Anxiety can be harmful, she...

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 choice,” Anne says, “of how I spend my time, the resources available to me, and am I doing enough? ... Am I doing the most with the opportunities I...

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 anyone stressed, he acknowledges, but “at some level, you have to be wired to enjoy it… that's why I tell everybody who joins, ‘It's not for the...

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 doesn’t like to look back: “Golfers will always look back and blame the wind, a divot that wasn't repaired, a bad rake job, a mower cut that...

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-searching, he realized what he really enjoyed: “I liked to build companies. That is my craft ... If someone enjoys playing gold for six hours, I...

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 learn how to phrase things because people assume he’s “irate and we should change everything we’re doing,” Clint says. “I’ll post something and...

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 offered a job and said he wanted to consider another offer, Glen withdrew Transcarent’s offer because he didn’t want to be the highest bidder — in...

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 rate of learning, or my ability to consult the right people.” But over time, he has worked to fix past errors and earn everyone’s trust: “I can be...

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 this fighting style, ‘The Way of No Way,’” Wade says. “He would study all the different fighting styles, and he would say, ‘None of them is the...

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 culture. But then, after one such talk, the CEO — a longtime friend and former coworker — came up to Kim with an asterisk. As a Black woman, she...

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 flagship LLM, Claude, must adhere to a “constitution” of values that prioritize the good of humanity. And even though every company wants to “do AI”...

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 really growing that fast,” he says. He recalled one of his mentors, former BladeLogic chairman Steve Walske, explaining that everyone has an...

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 that “it becomes a ‘never enough’ dynamic, because when is it enough?” To this day, he comes home on Friday night and asks himself, “Did it mater that...

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 challenges of bending DNA to your own ends. “You didn’t invent biology,” Jason says. “You need to have humility in the face of it ... because life will...

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 coaches, and adapt. And their bosses, John explains, had to themselves as agents of transformation. “If somebody’s really smart, they’re going to pick...

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 people are unhappy. After the time needed for sleep, daily exercise, friends, and family, Dr. Duckworth explains, “what’s left is more than 40...

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 already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be...

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 back to Doerr and told him “We’ve got some good news and some bad news.” The good news was that they agreed on the need for a CEO; the bad news,...

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.” And the easiest way to do that he’s found is to keep moving, keep failing, and keep creating. The material wealth he’s created, he explains, was...

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. With a several-year lead on generative AI tools like ChatGPT, Glean has built a growing club of CIO fans. With the broad acceptance of AI over the...

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 what you saw at the peak and you take that with you into the next experience.” He stressed that the pleasure of being at the top is a fleeting...

Guest: Brian Long, former CEO of Attentive and author of Problem Hunting: The Tech Startup Textbook Brian Long’s most recent company, Attentive, was originally designed to help clients communicate with their distributed workforce — but about six months in, he and his co-founder realized that that business would not grow as quickly as they had hoped. So, they decided to pivot to SMS marketing, at the cost of a few dubious employees and a well-known Fortune 500 client. The successful pivot...

Guest: Spencer Rascoff, co-founder and former CEO of Zillow + co-founder and general partner at 75 & Sunny  When terrorists attacked the US on 9/11, Hotwire co-founder Spencer Rascoff and his colleagues had to put their own trauma aside and “spring into action” — the travel site had sold tens of millions of dollars’ worth of non-refundable flights and hotel rooms and customers who wouldn’t be traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer...