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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 the office, Scott McNealy, the dotcom bust, Myers-Briggs, Star Trek: The Next Generation, empowering leaders, Blue Nile, Robert, Chatwani, tech leaders with children, Bain Capital, time management, being “in the moment,” Dave Goldberg, Dustin Moskovitz, staying curious, and being prescriptive.
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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 legacies, the wrong way to raise capital, authenticity, Ponzi schemes, “fool’s gold,” high-risk hiring, hitting pause, your “other family,” and changing roles.
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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 make. You will hate yourself ... I look forward.”
In this episode, Scott and Joubin discuss Scott Cook, Maverick McNealy, why big companies are riskier than startups, Al Gore, Marc Andreessen, Mark Zuckerberg, Kodak, Dick Kleinhans, Harvard University, “bozo invasions,” Myers-Briggs, making an example, Motorola car phones, the Moscone Center, Elon Musk, Jeff Bezos, NVIDIA’s valuation, farewell letters, “you have no privacy,” open-source education, and toothpaste.com.
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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 of Grit, Carlos Delatorre, Tom Mendoza, Glean, growing up in India, traveling the world, three-star restaurants, soul-searching, automating gruntwork, paying for nice hotels, red-eye flights, product-market fit, Jeff Bezos, the “three-layered cake,” Frank Slootman, raising the bar for distribution, technical debt, structural efficiency, and taking pride in your work.
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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 bug report is clear, workers with more experience at Cribl then have to reassure the newbies: “Calm down. When he does this, he’s not upset. He’s one of the power users of the product.”
In this episode, Clint and Joubin discuss being on the road, niche audiences, top-of-funnel problems, “come to Jesus” meetings, moving the goalposts, building for building’s sake, “down and to the right,” mediating re-orgs, flat organizations, filing bugs as the CEO, setting the example, Henry Schuck, Baldur’s Gate III, legal narratives, Hacker News, Cisco, Doug Merritt, Gary Steele, Rippling, and dead trends.
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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 other words, hire low. But whenever he has to let someone go, he sees it as his responsibility to “help them go off and do something else that’s great, and be successful.” Firing and replacing executives, he said, is “just part of growing ... it doesn’t have to be ugly.”
In this episode, Glen and Joubin discuss conservative values, John Doerr, Teledoc, failures of leadership, Steve Case, Bill Gates, changing expectations, Travis Kalanick, incentive bonuses, Bucknell University, massive layoffs, criticizing in public, anonymous charity, cycling events, Michael Jordan, Bill McDermott, Barack Obama, private jets, and hiring without titles.
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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 only as good as the rate at which I fix my mistakes,” Filip says.
In this episode, Filip and Joubin discuss “the good old days,” first principle thinking, the business impact of the COVID-19 pandemic, the Bay Area bubble, going public, Aaron Levie, going down rabbit holes, power dynamics, idea validation, Brian Long, Hans Robertson, DIY entrepreneurship, commercial kitchens, cash efficiency, VR headsets, zeitgeist-y platform shifts, Mark Zuckerberg, and John Doerr.
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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 or the worst ... My job was to take the best of each and then discard the rest, and make it my own.’”
In this episode, Wade and Joubin discuss fully remote companies, long-term thinking, hyperscaling, product-market fit, broken products, secondary offerings, “delocation packages,” interview questions, mind-breaking growth, doubting yourself, LLMs, hackathons, and adding a sales team (eventually).
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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 explained, “as soon as I offer anyone even the most compassionate, gentle criticism, I get assigned the ‘angry Black woman’ stereotype.” Kim realized in that moment that her book needed a prequel of sorts, explaining what you need to have before you can create radical candor: “You're not going to care about people who you don't respect,” she says.
In this episode, Kim and Joubin discuss regret minimization, Juice Software, Sheryl Sandberg, saying “um,” moments of connection, Dick Costolo, negative truths, James March, snobbery, Charles Ferguson, Shona Brown, Fred Kofman, Christa Quarles, Jason Rosoff, Andy Grove, founders as outliers, Jack Dorsey, Steve Jobs, glows and grows, the Post Ranch Inn, failing your colleagues, sexual harassment, DEI, and intellectual honesty.
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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” right now, President Daniela Amodei says some of them should slow down. “I keep coming back to this idea of, ‘How much are you buying the hype?’” she says. “’How grounded are you in the reality of what's actually happening?’ And sometimes in business conversations, we tell a potential customer, ‘We don't think we're right for you.’”
In this episode, Daniela and Joubin discuss her brother Dario, staying grounded, hypergrowth startups, Claire Hughes Johnson, mechanistic interpretability, Paul Graham, AI training, what AI companies can learn from social media, Stripe, the pool of venture capital in the Bay Area, leading people, giving feedback to all your coworkers, interview questions, and Sheryl Sandberg.
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