Brian Long, former CEO of Attentive and author of Problem Hunting, discusses the importance of understanding the problem being solved, building and scaling companies, the value of relationships in sales, the rollercoaster of emotions when selling a company, the early stages and pivot of Attentive, and personal excitement in working with loved ones.

Spencer Rascoff, former CEO of Zillow, discusses his post-Zillow life, teaching grit to kids, the impact of 9/11 on his business, creating a discount travel company, and the importance of having a career mirror.

Luis von Ahn, CEO and co-founder of Duolingo, discusses returning to the office, hiring strategies, growing up in Guatemala, language education, and public speaking tips.

René Lacerte, co-founder and former CEO of PayCycle, discusses the challenges of being a CEO and the importance of adapting to change. Topics include office environment, work-life balance, family values, empathy for small businesses, and the fulfillment of starting a business. Lacerte also reflects on personal regrets and lessons learned, while exploring the concepts of intentionality and persistence in personal growth.

Parker Conrad, CEO of Rippling and Mamoon Hamid, partner at Kleiner Perkins discuss their experiences with startups, the challenges they faced, and the importance of executives being involved in problem-solving. They also delve into the concept of compound startups, deep integrations, and the inefficiency of buying separate software components. The podcast offers insights on fundraising dynamics, starting companies for the right reasons, and the unique series A of Rippling.

Evan Goldberg, Founder and EVP of Oracle NetSuite, discusses the journey of building the company, starting a tech startup, the challenges faced, and the importance of learning from past mistakes. They reflect on their work at Oracle, the financial losses experienced during an IPO, and the resilience of loved ones. They also share their passion for writing software and talk about the endless creative possibilities in the industry.

Rahul Roy-Chowdhury, CEO of Grammarly, discusses the potential of AI and responsible technology, their journey to becoming CEO, the importance of focusing on problems rather than solutions, and the power of 'grit' in leveraging technology innovation for communication and productivity.

Jeff Shiner, CEO of 1Password, discusses building a good product, distinguishing between customers and users, sleeping patterns, fear of failure, the Silicon Valley bubble, raising funding, eliminating obstacles as a CEO, using Ryan Reynolds in commercials, emotional significance of long-term employees, launching a new product, reflections on the entrepreneurial journey, and the meaning of grit.

CRO of Anduril Industries, Matt Steckman, talks about the importance of defense tech, barriers to entry, government decision making, utilizing AI for border security, acquisition of Dive Technologies, qualities for success, and hiring needs in the defense industry.

Greg Brown, CEO of Udemy, discusses fitness routines, setting priorities, and being intentional with family. He talks about the distraction of stock price, daily to-do lists, and applying AI to customer solutions. They also explore cold plunge therapy, the journey from football quarterback to CEO, and determining when it's time for growth. The chapter concludes with hiring at Udemy and the concept of grit.