Grit

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 slee...

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 compan...

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 new...

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...

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 li...

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 y...

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 t...

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...

Guest: Luis von Ahn, CEO and co-founder of Duolingo When Luis von Ahn wanted to go to college in the United States, he had to take a standardized test called the TOEFL, or Test of English as a Foreign Language. But there was nowhere in his home country of Guatemala that could accommodate another test-taker, so he flew to war-torn El Salvador, just to take the TOEFL. Many years later, as the co-fou...

Guest: René Lacerte, CEO of Bill René Lacerte co-founded the online payroll firm PayCycle in 1999, and led it for six years until he was asked by the board to step down. Today, with 17 years as the CEO of Bill under his belt, he’s able to look back on that time with clearer eyes. “The title on my card is ‘CEO and Founder,’” he says. “At Paycycle, it was ‘Co-Founder and CEO.’” The order matters, be...

Guests: Parker Conrad, CEO of Rippling, and Mamoon Hamid, partner at Kleiner Perkins How long did it take for Parker Conrad to stop wanting revenge? “I’ll let you know when it switches over,” the Rippling CEO and co-founder jokes. He resigned from his last company , the buzzy HR unicorn Zenefits, in 2016 and then quickly realized that the company’s new leaders would never return it to its former g...

Guest: Evan Goldberg, founder and EVP of Oracle Netsuite In the late 1980s and early 1990s, Evan Goldberg working at Oracle, helping to bring its database software to the Mac. He left in 1995 because “I always wanted to do my own thing” and — with Larry Ellison’s support — launched his first startup, Embed. When it failed, he told Larry that he wanted another bite of the apple. “It’s the most exci...

Guest: Rahul Roy-Chowdhury, CEO of Grammarly Driven by generative tools like ChatGPT, artificial intelligence is hot — but Grammarly CEO Rahul Roy-Chowdhury wishes that “AI” stood for something else: “Augmented Intelligence.” A longtime Googler and lifelong believer in using technology to make peoples’ lives better at scale, Roy-Chowdhury now leads a company well-positioned to do exactly that. “In...

Guest: Jeff Shiner, CEO of 1Password Far from the Silicon Valley bubble, in Waterloo, Ontario, they try to do things a bit differently, says 1Password CEO Jeff Shiner. “Our mantra has been, build a good product, support the heck out of your customers,” he says. Some businesses and VCs in the Valley, he argues, don’t draw enough of a distinction between customers and users, spending all their time...

Guest: Matt Steckman, CRO of Anduril Industries Walk into one of Anduril Industries’ offices and it might take a minute for you to realize: This is a defense contractor. “It feels like a tech company, stylistically,” says CRO Matt Steckman, “because we know we have to recruit the best software talent in the world.” Matt says the executive team spends a “comical” amount of time on recruiting, one o...

Guest: Greg Brown, CEO of Udemy Every night before he goes to bed, Greg Brown makes a to-do list. He has to because, as the CEO of the online learning platform Udemy, setting his priorities helps ensure that he makes the most of the scarce time on his calendar. “If I’m meeting with employees, what’s the message I want them to walk away with?” he asks. He also wants to make sure his team isn’t gett...

Guest: Chris Degnan, CRO of Snowflake Chris Degnan was a teenager when his world got turned upside-down: His stockbroker father was revealed to be a serial liar & fraudster and was sent to prison; the wealth he thought his family had evaporated; and their house was foreclosed on by the IRS. The traumatic experience gave him both an “insane drive” and a slew of anxieties, which shaped the perso...

Guest: Jim Lanzone, CEO of Yahoo Jim Lanzone doesn’t waste time thinking about what other people think of him ... or the companies he has run. After helping to rejuvenate Ask.com in the early 2000s, he has more recently served as CEO of Tinder, and now Yahoo. As an expert in brand turnarounds, he says, “don’t worry about what the world thinks ... worry about your growth versus yourself.” With a fo...

In this special episode of Grit, Joubin looks back at what five past guests had to say about building a sales operation inside rapidly-growing companies: Intro (00:30) Stripe’s Mike Clayville on first principles & “tornado companies” (01:02) Former Paypal VP Marcy Campbell on establishing a successful sales motion (11:37) LinkedIn COO Dan Shapero on effective sales leadership during hypergrowt...

Guest: Yan-David Erlich, COO and CRO of Weights & Biases After starting four companies, Yan-David Erlich had found happiness and success as a GP in Coatue’s venture fund — but then, after investing in the AI developer platform Weights & Biases, he realized the time was right to get back into operating. That was not a decision he made lightly, consulting with his wife before he became the s...

Guest: Nick Mehta, CEO of Gainsight Gainsight CEO Nick Mehta describes himself as “the person who goes all in, on whatever.” So when he had a personally difficult year, he didn’t just go to therapy — he also talked to a professional coach, and read about religion, and experimented with (legal) ketamine therapy. All of that led to him “better understanding the inner self ... [and] helping to find w...

Guest: Manny Medina, CEO of Outreach In its Seattle headquarters, the sales execution platform Outreach has at least one wall covered in AI diagrams and architectural flows. CEO Manny Medina says that’s because he believes “there’s no world in which reps don’t have an assistant the way that coders do.” The AI revolution has also given Manny — who got his M.A. in computer science at Penn — a chance...

Guest: Aaron Levie, CEO of Box, and Mamoon Hamid, partner at Kleiner Perkins When he was a newly minted venture capitalist at USVP, Mamoon Hamid got a tip that he should meet a young entrepreneur named Aaron Levie, and fought for the right to invest in his cloud storage startup, Box. For years after that initial investment, the two men say, Box’s fate was precarious: “We could have died any day,”...

Guest: Carl Eschenbach, co-CEO of Workday When Carl Eschenbach decided to leave VMWare after more than 14 years as COO, no one believed it: Not chairman Joe Tucci, not CEO Pat Gelsinger, and maybe not Carl himself. But he needed a more predictable work-life balance to help raise his teenage children. For the next seven years, he served as a partner at Sequoia Capital. And every day, he thought — a...

Guest: Bob Muglia, “The Datapreneurs” Co-Author and Former Snowflake CEO Longtime Microsoft executive and former Snowflake CEO Bob Muglia was done with his book about using data to drive the digital economy — and then ChatGPT came out. “The timeline for artificial intelligence moved in by 50 years in my head,” he recalls. Bob then told his co-author Steve Hamm that they needed to update “The Datap...