Grit

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...

When Alex Norstrom started working at Spotify in 2011, CEO Daniel Ek told him there were three goals: Growth, growth, and growth. But Alex — now the Chief Freemium Business Officer — argued that his team would be better motivated by an “impossible goal,” something like reaching 100 million users. To which Daniel replied: “Let’s do it. Your goal is to get us to 100 million users. Please begin.” In...

Thrive CEO Arianna Huffington is best known for the pioneering online publication she founded, the Huffington Post, which she left in 2016. The experience of running the site awakened her to the most important problem she would tackle in her career: The intersecting crises of stress, burnout, poor sleep, and lack of focus, which Thrive teaches businesses how to manage. In this episode, Arianna and...

Archana Agrawal started her job as CMO of Airtable on March 18, 2020 — the same week that the US began to “shelter in place” as cases of the novel coronavirus rapidly rose. With kids who would be staying home from school and Airtable’s San Francisco office closed, everything was changing at once, so she switched into what she calls “problem-solving mode.” And, crucially, she discovered how to use...

As the CMO for Square, Lauren Weinberg spends a lot of her time talking to new and inexperienced small business owners — and she knows that each of them has wisdom that the others could benefit from. So, Lauren and her former colleague Jackie Reses wrote a book pooling all that wisdom into one place, Self-Made Boss: Advice, Hacks, and Lessons From Small Business Owners In this episode, Lauren and...

Handshake CEO and co-founder Garrett Lord was amazed when he first learned that Silicon Valley firms like Google recruited on college campuses ... just not his, Michigan Technical University. But after excelling in the competitive Palantir internship program, he started asking himself, “How come they can’t reach us?” That question led him to found the job placement platform Handshake, which has ra...

ThoughtSpot CMO Scott Holden spent eight years at Salesforce, putting in the time every year behind the scenes at Dreamforce watching the company reach 20,000 employees. And he probably could have thrown his hat into the ring to be CMO there — but he didn’t want that. Instead, he says, “I had the hunger to go back and build something” with a strong mission and vision, so he left for a much, much s...

Every year, ZoomInfo CEO Henry Schuck writes a memo to his executive team, which is made to look like a letter to the board of directors. Even though he founded DiscoverOrg — the company that bought and became ZoomInfo in 2019 — Henry pretends in the memo to be a new CEO who has just been hired to clean up the old guy’s mess. The reason, he explains, is simple: It gets everyone focused on the prob...

Jaimie Buss, CRO of the e-learning platform Articulate, had an epiphany several years ago. While trying to simultaneously give her toddler a bath and catch up on work emails, some water splashed on her computer. After initially snapping at her son, she realized the importance of being “unapologetically present” with not only her family at home but her colleagues at work. Since this experience, she...

George Felix, now the CMO of Tinder, was marketing Old Spice body wash at a time when the brand was circling the drain. His team at Procter & Gamble almost let their big break slip away when initially passing on the “Hello ladies” campaign - an ad that would later go viral on Facebook and YouTube. George recalls how the agency pitching the idea stood their ground and pressed on with conviction...

Global Sales VP at Hopin Javier Ortega Estrada’s father is a counter-terrorism official in the Spanish army — teaching him at a young age that having a bigger purpose can drive you to do great things. And over the course of his entrepreneurial career, Javi has found his own special purposes, helping companies like Dropbox and, now, the buzzy experience platform Hopin grow at a blistering pace and...

When Confluent’s President of Field Ops Erica Schultz was 23, she was working at Oracle and cold-emailed the manager of the Argentina office, asking to work for him. This experience would open the door to opportunities in Buenos Aires and Miami, a time in Erica’s life she does not take for granted. As a leader today, she hopes to pass on this sentiment, constantly looking for individuals worth tak...

Ryan Azus, CRO of Zoom, has been selling all his life, from baseball cards as a kid to ads in the school newspaper to — crucially — books every summer in college. Every year, he and and thousands of other young people would be dispersed around the country to sell books door-to-door as part of an entrepreneurial program called Southwestern Advantage. That experience taught him valuable lessons abou...

Instabase’s Ozge Ozcan believes that many women have been fed a false story about motherhood: That it can be seen as a “decelerator” to one’s career. Instead, she’s found that raising two daughters has made her more competent in the chaotic, fast-paced world of early-stage startups. Through this experience, she’s had to learn how to be an “amazing leader” at home and in the office. In this episode...

Sarah Patterson, CMO of Samsara , doesn’t believe in keeping your armor up around your coworkers: “You’ve got something else on your mind, it’s going to come through,” she says. While working at Salesforce, she worked with a career coach and discovered that opening up about her personal and professional struggles brought her team closer. And that has also held true in her current role at Samsara,...

Kate Ahlering might be the perfect guest for this podcast. She eventually worked her way up to Chief Sales Officer of Glassdoor, but when she joined in 2013, she helped define the company’s leadership framework as GRIT: Growth, Results, Integrity, and Team. Glassdoor has continued using those values since her departure in 2020, and now as the CRO of Calendly, she is applying a similar framework to...

When Rippling CEO Parker Conrad was raising a massive $250 million round last year, he didn’t start by presenting his deck to venture capitalists in person. Instead, he sent a 39-minute demo of his product, recorded on the video app Loom. And, Loom’s CEO Joe Thomas says, “That was the most pleasant surprise.”  In this episode, Joe and Joubin discuss how Loom “stands on the shoulders of giants” lik...