“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 level up faster and do things you never could before. In this episode, Ben and Joubin discuss giving sp...
Oct 10, 2022•1 hr 19 min•Ep. 107
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 music in the park, and turned their sleepy storefront into a party. That desperate play underscored one...
Oct 03, 2022•1 hr 7 min•Ep. 106
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 that,” he says. “That dispersion that started a decade ago accelerated over the last couple years ....
Sep 26, 2022•1 hr 13 min•Ep. 105
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 struck, hands were shook, but there was just one problem: The U.S. Department of Justice. In this e...
Sep 19, 2022•1 hr 19 min•Ep. 104
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, ‘This person has no idea what they’re doing. They just happen to be in the right spot at the right tim...
Sep 12, 2022•1 hr 6 min•Ep. 103
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 level of assisted driving available in every vehicle on the highway, not just premium cars like Teslas...
Sep 05, 2022•47 min•Ep. 102
“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 value of education beyond doing well on the next test. Something must have stuck, because Thomas is...
Aug 29, 2022•52 min•Ep. 101
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 recalls, is that they believed there was only o...
Aug 22, 2022•1 hr 6 min•Ep. 100
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, the mountain’s not gonna change,” he says. “We could still maybe get to the summit, even though the...
Aug 15, 2022•1 hr 11 min•Ep. 99
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 depression. To break out of this funk, Godard says he had to embrace presence and reckon with why entrepren...
Aug 08, 2022•1 hr•Ep. 98
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,” he says. “Society values some of the things I’ve accomplished, but when I admit to everyone that I...
Aug 01, 2022•1 hr 10 min•Ep. 97
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 values is to set crazy big goals and make them happen,” Zach says. In this episode, Zach and Joubin discu...
Jul 25, 2022•1 hr 5 min•Ep. 96
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 can be successful in business without doing bad things,” he says. “Being a good person and winning ...
Jul 18, 2022•1 hr 13 min•Ep. 95
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 actually great marketers to tell you what that is.” In this episode, Jason and Joubin discuss learn...
Jul 11, 2022•1 hr 3 min•Ep. 94
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 seven-figure contracts. In this episode, Peter and Joubin discuss the hierarchy of majors at MIT, bu...
Jul 04, 2022•1 hr 10 min•Ep. 93
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. “I feel like our job is to help our families realize their fullest potential first, and then work is...
Jun 27, 2022•1 hr 3 min•Ep. 92
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 this episode, Frederic and Joubin discuss literally walking down memory lane in San Francisco, who his...
Jun 20, 2022•1 hr 19 min•Ep. 91
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 Garrett Langley, who says stories like this have validated his company’s mission of stopping crime in our ...
Jun 13, 2022•1 hr 9 min•Ep. 90
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 developing peccadilloes as you get older, why a former boss told her “if you’re in a bad mood, don’t come to ...
Jun 06, 2022•1 hr 13 min•Ep. 89
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 this episode, Alex and Joubin convene at Spotify’s brand-new Stockholm studio to discuss his first j...
May 30, 2022•1 hr 23 min•Ep. 88
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 Joubin discuss how she went from a poor family in Greece to president of the elite Cambridge Union ...
May 23, 2022•1 hr 1 min•Ep. 87
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 family time to de-stress. In this episode, Archana and Joubin discuss how she made her way from Afri...
May 16, 2022•1 hr 3 min•Ep. 86
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 Joubin discuss why Lauren never leaves home without sneakers post-9/11; how she maintains discipline...
May 09, 2022•1 hr 1 min•Ep. 85
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 raised $434 million in funding and is used by 100 percent of the Fortune 500. In this episode, Garrett...
May 02, 2022•53 min•Ep. 84
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 smaller company: The business intelligence company ThoughtSpot, where he has worked since 2015. In th...
Apr 25, 2022•57 min•Ep. 83
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 problems that have to be fixed. In this episode, Henry and Joubin discuss the difference between wearing...
Apr 18, 2022•1 hr 6 min•Ep. 82
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 has drawn clear boundaries between the two. In this episode, Jaimie and Joubin talk about the leade...
Apr 11, 2022•1 hr 2 min•Ep. 81
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, an experience that taught him a lot about trusting your gut and standing up for what you believe i...
Apr 04, 2022•59 min•Ep. 80
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 deliver value to their customers. In this episode, Javi and Joubin talk about uprooting his life (af...
Mar 28, 2022•54 min•Ep. 79
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 taking a chance on: “As I look around my organization, I think, OK, who’s the undiscovered not-yet-full...
Mar 21, 2022•1 hr 7 min•Ep. 78
