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 explain...
Feb 19, 2024•1 hr 10 min•Ep. 178
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” righ...
Feb 12, 2024•2 hr 46 min•Ep. 177
Guest: Dev Ittycheria, CEO and President of MongoDB When you think about who you were and the decisions you made two, or four, or eight years ago ... how do you feel? Dev Ittycheria, the President and CEO of MongoDB, says he’s embarrassed about certain things he did — and that’s a good thing. “If you’re not [embarrassed], that means you’re not really growing that fast,” he says. He recalled one of his mentors, former BladeLogic chairman Steve Walske, explaining that everyone has an overinflated ...
Feb 05, 2024•1 hr 6 min•Ep. 176
Guest: Frank Slootman, CEO and Chairman of Snowflake and author of Amp It Up Snowflake CEO Frank Slootman doesn’t recall a time in his childhood where new achievements were celebrated — because, according to his father, putting everything into your work and “leaving it all on the field” was the only choice. “The problem with it,” Frank says, is that “it becomes a ‘never enough’ dynamic, because when is it enough?” To this day, he comes home on Friday night and asks himself, “Did it mater that I ...
Jan 29, 2024•54 min•Ep. 175
Guest: Jason Kelly, CEO and co-founder of Ginkgo Bioworks Almost everyone in the second generation of biotechnology entrepreneurs, says Ginkgo Bioworks CEO Jason Kelly, works in that field because of one thing: Jurassic Park . The Michael Crichton novel-turned-Steven Spielberg movie captured both the wonder and beauty of bioengineering, and the challenges of bending DNA to your own ends. “You didn’t invent biology,” Jason says. “You need to have humility in the face of it ... because life will f...
Jan 22, 2024•1 hr•Ep. 174
Guest: John McMahon, author of The Qualified Sales Leader: Proven Lessons from a Five Time CRO A hell of a lot of people work in sales. But until recently, says five-time CRO and The Qualified Sales Leader author John McMahon, it was rare for colleges and universities to offer a sales degree. Salespeople had to learn on the job from experienced coaches, and adapt. And their bosses, John explains, had to themselves as agents of transformation. “If somebody’s really smart, they’re going to pick up...
Jan 15, 2024•2 hr 33 min•Ep. 173
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 sleep, daily exercise, friends, and family, Dr. Duckworth explains, “what’s left is more than 40 hours.”...
Jan 08, 2024•1 hr 11 min•Ep. 172
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 company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an ...
Jan 01, 2024•1 hr 13 min•Ep. 171
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 news and some bad news.” The good news was that they agreed on the need for a CEO; the bad news, Doerr ...
Dec 25, 2023•1 hr 6 min•Ep. 170
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 keep moving, keep failing, and keep creating. The material wealth he’s created, he explains, was ne...
Dec 18, 2023•1 hr 3 min•Ep. 169
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 like ChatGPT, Glean has built a growing club of CIO fans. With the broad acceptance of AI over the pas...
Dec 11, 2023•46 min•Ep. 168
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 you into the next experience.” He stressed that the pleasure of being at the top is a fleeting incent...
Dec 04, 2023•56 min•Ep. 167
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 the cost of a few dubious employees and a well-known Fortune 500 client. The successful pivot confirm...
Nov 27, 2023•1 hr 5 min•Ep. 166
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 traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer teach...
Nov 20, 2023•1 hr 11 min•Ep. 165
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-founder and CEO of Duolingo, Luis and his team “decided this type of thing, we could do a lot better.” ...
Nov 13, 2023•1 hr 4 min•Ep. 164
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, because once you’ve become a founder or co-founder, you are one no matter what — and in hindsight, Ren...
Nov 06, 2023•1 hr 3 min•Ep. 163
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 glory. He still loved the problems he had been trying to solve, and launched Rippling because “there ...
Oct 30, 2023•1 hr 2 min•Ep. 162
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 exciting, it’s the most satisfying,” Evan said of startups. “It’s the highest risk, but ... even though ...
Oct 23, 2023•1 hr 6 min•Ep. 161
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 the early days, Grammarly was all about the rules of language,” he says. “Now, with generative AI, ...
Oct 16, 2023•1 hr 3 min•Ep. 160
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 chasing the latter. For many years, the whole team at 1Password — including the co-founders — would ...
Oct 09, 2023•1 hr 4 min•Ep. 159
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 of his personal passions, and especially works to minimize the number of people who turn down offers....
Oct 02, 2023•1 hr•Ep. 158
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 getting distracted by Udemy’s stock price. “Where it be sports, or life, or in business, you’ve got to b...
Sep 25, 2023•1 hr 1 min•Ep. 157
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 person he became as an adult ... and led him, eventually, to the C-Suite of Snowflake. “Those things have...
Sep 18, 2023•54 min•Ep. 156
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 focus on people and product, Jim believes, “not only can you accomplish a lot, you’re going to make a ...
Sep 11, 2023•1 hr 7 min•Ep. 155
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 hypergrowth (20:16) Herbold Consulting CEO Jim Herbold on “unicorn meat” (32:32) CRO Chris Degnan on the pivot...
Sep 04, 2023•1 hr 8 min•Ep. 154
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 startup’s COO. The challenges of entrepreneurship get easier, he explains, when you have a supportive...
Aug 28, 2023•1 hr 12 min•Ep. 153
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 ways to suppress the exterior.” In other words, even though Gainsight’s culture is suffused with Nick...
Aug 21, 2023•1 hr 12 min•Ep. 152
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 to be more hands-on than your average CEO of a $4 billion company. “I try not to think myself as a ...
Aug 14, 2023•1 hr 7 min•Ep. 151
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,” Mamoon says, and Aaron recalled several times he had to be talked “down from a ledge.” Today, they t...
Aug 07, 2023•1 hr 3 min•Ep. 150
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 — and to his wife’s chagrin, talked — about going back: “It was always on the back of my mind,” he says...
Jul 31, 2023•1 hr 22 min•Ep. 149
