In a world where most people optimise for stability, Vasuta Gupta has built her career by doing the opposite. From starting her journey in chip design to advising CEOs at McKinsey, helping scale InMobi through multiple phases of growth, and now leading revenue at an AI-first company, she has consistently made decisions before the future became obvious.

In this conversation, Vasuta shares the frameworks behind her biggest career moves, why she believes the best time to leave a role is when you become too comfortable, what she learned from spending 13 years inside one of India's most successful technology companies, and how AI is reshaping careers, leadership, and the future of work.

Shruthi is an author and the Director of Analytics, Innovation, and AI at Adobe. At 14, Shruthi made a decision that went against the conventional path many ambitious students follow. That choice reflected a mindset that would later take her from an early-stage startup to Adobe. 

In this conversation, we discuss curiosity, startup failures, sports, meditation, and how to balance ambition with contentment in a world obsessed with achievement. She also shares about her book “The Store of Life- How to fill your life with Contentment, Not with Accomplishments”.

Yosha is a serial entrepreneur who is on her 2nd startup, MeMeraki, India's largest culture-tech platform. Growing up in Aligarh, a small town in India, she was influenced by her mother’s amateur artistry and her father’s entrepreneurial grit, and she witnessed him persevere through setbacks to launch a new business at age 60. This foundational resilience carried over into her early career, where she spent over 15 years working on financial inclusion and innovation for global institutions such as the World Bank Group and the Gates Foundation.

Shane is the founder of Farnam Street (FS) and host of The Knowledge Project (TKP) podcast, dedicated to helping people master mental models, decision-making, and lifelong learning. A former Canadian intelligence official, he transformed a side project into a top business resource and authored the bestseller Clear Thinking and The Great Metal Models series.

⁠Monsoon Pabrai is the founder of Drew Investment, a value fund she launched at age 25. Representing a new generation of investors, she adapts classic value principles to the modern landscape, shifting focus from tangible balance sheets to intangible assets like network effects and goodwill.

Although raised at the dinner table of a legendary value investor—meeting Warren Buffett at 12—Pabrai emphasises that her foundation was built on traditional operational discipline and EQ. This conversation explores the independence and discipline required to build a career in investing, not just abstract formulas.