Grit

PagerDuty CEO Jennifer Tejada has mixed feelings about how she is often portrayed in the press, as a “badass woman CEO.” The scarcity of female executives in enterprise means that it’s often the first thing anyone wants to talk about — not her performance leading a $2 billion company, or her team. She has specifically designed that team to include more under-represented people like her, so that sh...

When DVx Ventures co-founder Jon McNeill joined Tesla in 2015, he told his new boss Elon Musk: “You won’t see me at least a day a week.” That’s because Jon believes the job of any leader is to make time to talk to front-line workers who know things executives don’t. While he was at Tesla he spent 20% of his time in service centers, support centers, or in retail stores, asking the people who worked...

Health monitoring company Whoop, founded and led by CEO Will Ahmed, hid a secret message on the circuitboard of its latest wearable device. “It says, ‘Don’t bother copying us, we will win,’” Will says. “And it also has every engineer who worked on Whoop 4.0’s initials.” For more than 10 years, Whoop has attracted fans from world-famous athletes to everyday consumers, and its deep-pocketed rivals h...

As a veteran of several high-powered organizations — including McKinsey, Google, Dropbox — Notion advisor Olivia Nottebohm has learned the importance of respecting her teams’ personal journeys. She believes none of the 10 most important milestones in any person’s life will be career-related, and it’s important for leaders like her to strike a balance between accountability and empathy. “Before I n...

“I literally thought to myself, I probably made the biggest mistake of my life taking this job.” That’s what Ali Ghodsi recalls about his decision step up the CEO role at Databricks, which would mean leaving a desirable post at UC Berkeley. He wasn’t sure if the company would make it, and some of Databricks’ board agreed that as an academic, he wasn’t right for the job. But they all wound up being...

Before Zscaler’s Dali Rajic arrived at his current company, he helped grow AppDynamics from $7 million in annual recurring revenue to nearly $1 billion — and for his next move, he knew he had to do something even bigger. That’s why he was excited to transition to Zscaler’s COO in February after more than two years as its CRO: “It was a job worth taking because it stretched me and it made me uncomf...

“Everyone excellent at their craft starts from a place of deep insecurity,” says Flexport’s founding CRO Ben Braverman. People are “slow-burning fireworks,” he explains, and we need time to learn how to do anything well. If you lie to yourself, you won’t ever improve; but if you admit the truth and approach people who know more with genuine curiosity and enthusiasm, Ben says,  you’ll be able to le...

When Sweetgreen CEO Jonathan Neman and his co-founders opened their second-ever store, it was a “complete mess.” Located in Washington D.C.’s Dupont Circle and opening in the middle of the Great Recession, it was clearing less than $1000 per day at first. But Neman & co turned that crisis into opportunity the only way three 23-year-olds knew how: They bought a big speaker, started blasting mus...

For more than 10 years, AOL co-founder and Revolution Chairman Steve Case has been investing in startups in all corners of the US — and urging others to do the same. His new book about this movement, The Rise of the Rest , explains why: The next wave of the tech industry, he argues, is not going to be anchored to physical offices in Silicon Valley alone. “The pandemic has created more attention on...

Intuit co-founder Scott Cook still remembers the first line of an email he received in 1994 from billg@microsoft.com: “This really is Bill Gates.” Intuit’s personal finance product Quicken had survived being crushed by Microsoft Money, and its new accounting software Quickbooks was thriving as well; instead of competing, Gates wanted to buy Intuit for $1.5 billion and take it worldwide. A deal was...

Productboard founder and CEO Hubert Palan has made a point of studying the communication style of other leaders, from Martin Luther King Jr. to Elon Musk. But as the boss of a hot and growing tech startup, he’s realizing just how exceptional those people are. “You’re interviewing some of the top execs from companies are the Silicon Valley darling brands,” he says. “You leave the interview like, ‘T...

Qualcomm CEO Cristiano Amon believes his company is perfectly positioned for the world economy of the future, connecting everything from phones to exercise bikes to cars. And he predicts we’re about to see AI-assisted cars  deployed at a “mass scale.” Fully autonomous vehicles, he concedes, will take longer — perhaps 5 or 10 years — but he says it’s in everyone’s interest to make an intermediate l...

“When I grew up in Bangalore, I’d never seen a computer,” says Thomas Kurian. The former president of Oracle, now the CEO of Google Cloud, remembers learning how to write while sitting outside his childhood home, and doing homework by candlelight during power blackouts. He credits his “trailblazer” mother, who instilled curiosity and discipline in all her children, with helping them understand the...

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 th...

Touch The Top CEO Erik Weihenmayer, the first blind person to summit Mount Everest, climbs hundreds of mountains every year. And he’s learned over the years that sometimes, the smartest thing to do in the face of adversity is stop, turn around, and go home; but in other situations, like an unexpectedly icy day climbing Mount Kenya, one only has to change their approach. “The mountain doesn’t care,...

After rescuing his first startup BigMachines from the brink of bankruptcy and building it to positive cash flow, Godard Abel thought the express lane of life was opening up to him. But after the board replaced him as CEO, Godard — now the CEO of B2B tech buying firm G2 — found himself on a rocky road for 10 years. He had all the money he could want, but also overwhelming fear, anxiety, and depress...

Mark Roberge’s first anxiety attack hit him six months after 9/11, and his second hit him in the middle of a big speech while he was an executive at HubSpot. And Roberge, who now lectures at Harvard Business School and co-founded the venture firm Stage 2 Capital, says it’s important to include that anxiety in his entrepreneurial story. “I talk about it because there is a stigma associated with it,...

Canva CMO Zach Kitschke was the company’s fifth employee, joining right before the product launched to the public — or, that was the plan anyway. Emerging technologies like HTML5 and negative feedback from early testers delayed the debut of the design startup, but in the 10 years since its launch Canva has become one of the most successful companies to ever come out of Australia. “One of our value...

Girish Mathrubootham is the founder and CEO of Freshworks, the first Indian SaaS company to be listed in NASDAQ — and when he’s in his home country, he gets the celebrity treatment. Freshworks’ 2021 IPO was a milestone for the country’s tech sector, and Mathrubootham has also attracted a “take a selfie with me!” level of fame for trying to change the conversation about entrepreneurship there. “You...

Riot Games CMO Jason Bunge knows you might roll your eyes when he says this, but he doesn’t care, because it’s the truth: Marketing doesn’t get enough respect. Although many companies have convinced themselves that they don’t need a traditional marketing division, they’re very wrong. “If you care about your brand [and] you care about your customer,” he says, “you need great marketing. And you need...

Before Peter Reinhardt started his current company, Charm Industrial, he was the CEO and co-founder of the customer data platform Segment, which almost died in its first year. Why? He was afraid to ask customers to pay more than $10 per month for it. A savvy sales advisor pressured him to raise the price by 1000x, which worked wonders. By early 2022, Segment — now owned by Twilio — was commanding...

Clari CEO Andy Byrne says he never wants to look back and see that he put more into his work than his family. But that doesn’t mean he can’t learn a thing or two from running a 600-person multi-billion dollar business: Inspired by business books, he and his wife Julie set goals, methods and OKRs for their family, and even asked their kids to grade them on how well they were hitting their targets....

In the early days of Okta, co-founder Frederic Kerrest was courting a 3,000-person company in Louisiana, which was considering Okta and one other vendor. When he learned who he was up against, he said, “We love competing with them ‘cause we beat them every time.” That arrogant boast lost him the deal, and taught him a humbling lesson: Your confidence is not superior to your customer’s needs. In th...

In April, a young girl was kidnapped and sexually assaulted in Yakima, Wash., and later told police she was picked up by a stranger in a car. The case might have gone cold there, if Yakima hadn’t just installed Flock Safety cameras : The cameras were able to pinpoint a car matching the girl’s description, and picked up the alleged abductor outside an elementary school campus, says Flock CEO Garret...

Leyla Seka has a clear idea of “what makes me great” as the COO of Ironclad: She’s incredibly direct with her team. Although many people are not comfortable with getting direct feedback, she says, “I can’t do my job if I can’t tell you what I’m seeing.” And in the end, she sees her job as one of seeking out the truth, to make her business better. In this episode, Leyla and Joubin discuss developin...