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 monthly active users, the social platform is appealing to a lot more than hardcore gamers. “People on ..read more

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 to be far more transparent than established PBMs, or Pharmacy Benefit Managers, and Mark clearly relis ..read more

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 warming. So, he and his co-founders Avi Itskovich and Christian Anderson all left Stripe to start Watershed ..read more

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 technology improves over many years, it could replace text entirely. “I think for most people, if they h ..read more

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 concedes, but “there’s a healthy version of believing you never really know what’s going on, and you ne ..read more

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, and making as positive an impact as I can?” In this episode, Anne and Joubin discuss returning to th ..read more

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 faint of heart.’” In this episode, Sanjay and Joubin discuss Reddit, banker friends, professional legaci ..read more

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't done properly, a gust of wind,” he explains. “If you blame yourself for all of the mistakes you ma ..read more

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 would enjoy working on a startup for six hours.” In this episode, Jyoti and Joubin discuss the evolution ..read more

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’s a flurry of DMs that are happening in the background, like ‘Oh my God.’” Unless the tone of his bu ..read more