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 bucks in ad revenue and you're like, ‘Oh my God, I'm worthless,’” Jack recalls. “And you check that dashboard every day ... and eventually you sta...
Sep 16, 2024•1 hr 9 min•Ep. 208
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 50 percent science” — but it’s not enough to just have the instinct. Mark says entrepreneurs like him have to quickly take multiple shots on t...
Sep 09, 2024•1 hr 14 min•Ep. 207
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 from one person to seven to 17,000, though, RJ admits that there’s a lot more pressure to not screw up. “There’s all these conflicting emotions I had ....
Sep 02, 2024•57 min•Ep. 206
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 made him a successful leader before. “You should be truthful with yourself about what is it that you know that you're really good at,” he says. In this...
Aug 26, 2024•1 hr 7 min•Ep. 205
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 how he’ll be better in round 2. “I've changed so much — physically, mentally, emotionally — I feel like I could be a better collaborator,” James says...
Aug 19, 2024•1 hr 7 min•Ep. 204
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 in revenue in its first week, and $1 billion in its first seven months. “I had a huge amount of anxiety that this is just too good to be true,” John...
Aug 12, 2024•1 hr 9 min•Ep. 203
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 married and raised three children, and Mark found success in his new career, serving as CEO of Palo Alto Networks and now chairman of the board at Q...
Aug 05, 2024•1 hr 13 min•Ep. 202
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 readers around the globe; he had to convince himself that turning Lyft around during one of its most difficult eras was also a call worth answering. In t...
Jul 29, 2024•1 hr 16 min•Ep. 201
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 Ved Prakash: It’s going to be a lot bigger. “If you look at the next 10 years or the next 20 years, we are doing maybe 0.1 percent of [the] AI that w...
Jul 22, 2024•55 min•Ep. 200
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 never good at that when I was growing up,’” Andrew explains. “You know, ‘I'm not a good writer’ or ‘I'm not good with numbers.’ And it's like, well, OK...
Jul 15, 2024•1 hr•Ep. 199
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’ve done that, if you enjoy that, it’s very hard to pursue something more traditional.” But the “if you enjoy that” bit really matters: Whenever he’s ...
Jul 08, 2024•55 min•Ep. 198
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 in India. “I had no attachment for money. There was no feeling of ‘I must buy this, buy this.’ ... And it hasn’t changed a bit.” Perhaps surprisingl...
Jul 01, 2024•43 min•Ep. 197
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 will be usable by everyone that has smartphone technology.” In other words, the question is not business opportunity or scale: It’s capability. In this ...
Jun 24, 2024•57 min•Ep. 196
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 bad,” Clara says. But her worries subsided when her replacement and former COO, Mike Boese, guided the company with “class and grace” to an exit: A ...
Jun 17, 2024•45 min•Ep. 195
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 asked. He was asking if the board and C-suite were ready to lead the company forward, but Marissa thought he had one foot out the door. “I had just co...
Jun 10, 2024•1 hr 26 min•Ep. 194
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 rest, she argues, is their compassion and their responsiveness. When her former EA’s husband was diagnosed with cancer, Sarah texted Benioff — who sh...
Jun 03, 2024•1 hr 17 min•Ep. 193
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 teenager, Stanislav logged more than 1,000 days playing his favorite video game and socializing with friends around the world, but with 200 million ...
May 27, 2024•1 hr 4 min•Ep. 192
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 customers. But Eoghan believes “every single type of knowledge work” will soon be done by AI, and Intercom is well on its way to that destination: 45 pe...
May 20, 2024•59 min•Ep. 191
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 TV show Shark Tank . But his real focus — and his real enemy — these days is the pharmaceutical industry. His latest company, Cost Plus Drugs, aims ...
May 13, 2024•47 min•Ep. 190
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, he was working at Stripe and felt another call to arms: The 2020s would be a crucial decade for slashing carbon emissions and combating global warmin...
May 06, 2024•1 hr•Ep. 189
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 tec...
Apr 29, 2024•59 min•Ep. 188
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 co...
Apr 22, 2024•1 hr•Ep. 187
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 have,...
Apr 15, 2024•1 hr 6 min•Ep. 186
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 fain...
Apr 08, 2024•55 min•Ep. 185
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 wasn'...
Apr 01, 2024•1 hr 18 min•Ep. 184
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 woul...
Mar 25, 2024•59 min•Ep. 183
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 there’...
Mar 18, 2024•1 hr 12 min•Ep. 182
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 othe...
Mar 11, 2024•2 hr 30 min•Ep. 181
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 onl...
Mar 04, 2024•1 hr 13 min•Ep. 180
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 best ...
Feb 26, 2024•1 hr•Ep. 179
