Guest : Josh Silverman, CEO of Etsy When Josh Silverman joined the board of Etsy, he had one condition: “Don’t ask me to the be the CEO.” And technically, they didn’t ask. One day, he got a phone call informing him the board had elected him as the new CEO, just days before an earnings miss. He knew the odds were against him — layoffs would be necessary, and “I was going to have to be the villain” — but decided to say yes out of a sense of duty to Etsy’s users and workers. “If I can be helpful, I...
Nov 25, 2024•1 hr 10 min•Ep. 218
Guests : Varun Mohan, CEO & Co-Founder of Codeium; and Leigh Marie Braswell, partner at Kleiner Perkins “A lot of people are really bad at knowing what good is,” says Codeium CEO Varun Mohan. Specifically, he’s thinking of startups that hire based on a “logo” — a well-known company on the résumé — rather than exceptional talent. Codeium is based in Mountain View, CA, and Varun believes that it’s incumbent on any new startup to hire in the San Francisco Bay Area, because of how exceptional ta...
Nov 18, 2024•1 hr 1 min•Ep. 217
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 other organization that I know of.” The reason is backed up by the data: Personalized tutors — designed to help students achieve mastery in a subject...
Nov 11, 2024•47 min•Ep. 216
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 of the rest of it.” Matt likened the work to being a hobbyist airplane pilot, who can’t get a license without knowing all the minute details about t...
Nov 04, 2024•1 hr 5 min•Ep. 215
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 when a young startup entrepreneur from Seattle visited his business school classroom. Most of Jason’s classmates predicted the failure of this s...
Oct 28, 2024•1 hr 30 min•Ep. 214
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 after the deal was announced that he really understood what it meant for his team. “I didn't know how emotional it'd be for me,” Joe says. “All of th...
Oct 21, 2024•57 min•Ep. 213
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 kind of friendly, empathetic, more utopian vision.” George Lucas himself told Rony to tone it down and not “take it so literally” — but he was und...
Oct 14, 2024•1 hr 34 min•Ep. 212
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 banking startup as an ideal partner for OpenAI — so, he made up an excuse to fly to San Francisco and meet with Altman. “I felt like, OK, this is go...
Oct 07, 2024•1 hr 9 min•Ep. 211
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 took a long time to hire new execs, or partner with VC firms. Indeed, Kleiner Perkins partner Ev Randle recalls the deliberation Hanslovan underwen...
Sep 30, 2024•1 hr 8 min•Ep. 210
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 them that this time, they should stay put — he would commute between Florida and Detroit every week, and call home for an hour every night. “I pro...
Sep 23, 2024•1 hr 15 min•Ep. 209
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
