Grit

In this engaging discussion, Spenser Skates, CEO and co-founder of Amplitude, shares insights on navigating the evolving landscape of AI and analytics. He reflects on the challenges of integrating advanced technologies with a legacy codebase while emphasizing the importance of maintaining Amplitude's core strengths. Skates discusses the risks and rewards of taking the company public and shares personal anecdotes about leadership transitions and work-life balance. His thoughts on grit and the need for talent in AI offer valuable perspectives for aspiring entrepreneurs.

Ryan Petersen, CEO and founder of Flexport, returns to discuss his company's journey through the tumultuous landscape of global trade. After stepping aside during challenging times, he outlines his strategies for rebuilding while cutting $300M in costs. Petersen emphasizes the importance of promoting from within rather than seeking outside talent and shares insights on how rising tariffs impact U.S. businesses. He also reflects on balancing extensive business travel with family life, highlighting the need for passion over purely financial motives.

Pedro Franceschi, co-founder and CEO of Brex, shares his journey from a teenage hacker in Brazil to leading a fintech revolution. He discusses launching 'Brex 3.0' and the strategic shift to a single-CEO model for faster growth. Pedro explores the impact of small decisions, the importance of resilience in startups, and the radical transition to equity compensation over cash. He also emphasizes balancing wellness with productivity and the need to destigmatize mental health in high-pressure environments.

In this engaging conversation, Jay Chaudhry, the visionary Founder and CEO of Zscaler, shares his remarkable journey from a Himalayan village to building a $32B cloud security powerhouse. He reveals why half of the Fortune 500 trusts Zscaler and his unconventional approach to hiring, still personally interviewing candidates. Jay discusses the emotional challenges of entrepreneurship, his radical vision for a secure internet, and how he's spearheading the company's next big AI initiative. Discover his insights on travel efficiency and the drive that fuels his relentless passion.

Zac Bookman, CEO and co-founder of OpenGov, shares his journey in revolutionizing government transparency through innovative technology. He dives into his company's mission for effective governance, the challenges of product-market fit, and the high stakes of early startup life. Zac recounts near-failures, strategic acquisitions, and the transformative impact of a recent $1.8 billion acquisition by Cox Enterprises. He also candidly reflects on personal growth through a cross-country bike ride, facing unexpected challenges that mirror the turbulence of entrepreneurship.

Guest: Ben Chestnut, Former CEO and Co-Founder of MailchimpIf you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog. When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over. After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head."“After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.”Mentioned in this episode: Intuit, Wolt, DoorDash, LinkedIn, Dan Kurzius, Salesforce, ExactTarget, Pardot, Constant Contact, Rackspace, Free by Chris Anderson, Wired Magazine, Charles Hudson, the Freemium Summit, Drew Houston, Dropbox, Evernote, Phil Libin, TechCrunch, Brian Kane, Catalyst Partners, Georgia Pacific, Scott Cook, Bing Gordon, Vinay Hiremath, Loom, Joe Thomas, Caltrain, Flickr, Saturday Night Live, Droga5, Cannes Film Festival, Strava, Twitter, LinkedIn, Nvidia, Glean, Rubrik, Amazon AWS, and Mechnical Turk.Links:Connect with BenLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner Perkins

Guest: Blake Scholl, Founder & CEO of Boom Supersonic“Passion and drive trumps knowledge and experience,” says Boom Supersonic CEO Blake Scholl. Long before he was running Boom — which earlier this year successfully tested the world’s first privately-developed supersonic jet — he was enabling “the world’s most obnoxious spam cannon” at Groupon, or designing a barcode-scanning game for retail shoppers.But eventually, Blake found the courage to be more audacious and do something closer to his lifelong love of aviation. He began educating himself about things he had never thought to learn, and tapping his LinkedIn network to get intros to the smartest people in the industry. “If you imagine yourself on like the day of IPO, 99 percent of what you needed to know to get to that day, you didn't know on day one,” he says. “So, why not take 99 percent to 99.5 percent, and work on the thing you really want to exist, even if you don't know anything about it yet?”Chapters: (01:07) - Blake on Boom’s beginnings (01:52) - Breaking the sound barrier (05:23) - Concorde’s legacy (09:36) - Navigating regulations (12:08) - Boomless supersonic flight (16:48) - The test flight (20:11) - Day-of nervousness (24:26) - Carrying passengers (26:55) - Cost & wi-fi (30:19) - “No middle seats” (32:35) - Hard tech (36:48) - What if Apple made a plane? (39:08) - Blake’s career journey (43:29) - The risk of failure (49:12) - Finding the courage (52:49) - Balancing life with Boom (56:42) - Learning how to build a jet (01:00:20) - The power of LinkedIn (01:02:38) - Y Combinator Demo Day (01:08:24) - Richard Branson (01:11:38) - Dividing yourself (01:14:19) - Being a focused dad (01:20:05) - Exuberance vs. fear (01:24:15) - Hiring slowly (01:27:17) - What “grit” means to Blake Mentioned in this episode: Chuck Yeager, ChatGPT, the Apollo program, Elon Musk, SpaceX and Falcon 1, Boom Overture, Starlink, Boeing, Airbus, iPhone, Jony Ive, Uber, Airbnb, Anduril, United Airlines, American Airlines, Eclipse Aviation, Tesla, Scott Kirby, Mike Leskinen, Inktomi, Yahoo!, Amazon, Pelago, Google Ads, Kima Labs, Barcode Hero, Groupon, iPad, Eric Schmidt, Steve Jobs, Khan Academy, Sam Altman, Loopt, Virgin Atlantic, Paul Graham, Michael Seibel, Ashlee Vance, Bloomberg, Hacker News, Jared Friedman, Sen. Mark Kelly, SV Angel, Ron Conway, Virgin Galactic, Lockheed Martin, Gulfstream, Jeff Bezos, Jeff Holden, and How It’s Made.Links:Connect with BlakeTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

George Kurian, CEO of NetApp, shares insights on navigating his unexpected promotion and the complexities of leadership. He discusses the loneliness that often accompanies executive roles and the balance between personal life and work. Kurian highlights NetApp's remarkable turnaround into cloud services, emphasizing adaptability and innovation in the tech industry. He reflects on his upbringing in India, the cultural shift in values, and the importance of humility in leadership, all while addressing challenges in raising children in a privileged environment.

In this discussion, Winston Weinberg, CEO and co-founder of Harvey, shares his commitment to respecting the legal industry while integrating AI technology. Ilya Fushman, from Kleiner Perkins, emphasizes the role of AI as a collaborative copilot in various sectors. They explore the importance of thoughtful automation, distinguishing between enjoyable commitments and true sacrifices in work. The conversation also highlights innovative hiring in the AI legal space and the need for professionals to adapt as industries evolve.

Miki Kuusi, co-founder of the successful Finnish delivery startup Wolt and head of international at DoorDash, shares his insights from the tech industry. He discusses the evolution of food delivery services and the competitive landscape, revealing key strategic decisions during Wolt's journey. Miki reflects on his experience running the Slush tech conference and how it served as a school for entrepreneurship. He emphasizes balancing ambition with personal fulfillment, alongside the importance of recruitment and maintaining focus in a rapidly changing market.