Employee #1—> Co-founder/ CEO: Avnish's first job after his Indian Ivey League MBA was selling washing machines in a waterless Indian state. He joined CaratLane as employee number one almost by accident. Avnish never had the credentials for the job. He wasn't a marketer, product manager, or founder. Avnish later became CaratLane’s co-founder & CEO. In 2023, Titan paid about ₹4,600 crore for CaratLane. That valued the whole company at roughly ₹17,000 crore (about $2 billion), making it a “billion-dollar brand,”.

His story matters because he learned to turn those missing credentials into a method. He trusted common sense over best practice and borrowed ideas from sports, statistics, and other industries. Where most managers settle for paying people on results, he paid them to do the right things, and when he needed to, he changed the rules of his industry instead of only working within them. Under it all is one way of thinking: identify which variables you can actually control, measure them, and design for repeatability rather than luck. He is also frank about how much luck shaped his path, and how often CaratLane's good decisions only made sense afterward.

Saurav Chawla walked away from a Vice President's seat at Barclays in New York — the kind of job people spend a decade climbing toward, closing multi-billion-dollar M&A deals — and came home to India to open a bakery. Not as a fallback. As a deliberate pause. And it was inside that bakery, trying to staff his own kitchen through a busy evening, that he stumbled onto the problem that became OkayGo — India's largest task-fulfillment platform. It returned 10x to its investors, was acquired by BetterPlace, and then did the harder thing: it scaled 20x. Today, Saurav is a co-founder of BetterPlace, Asia's largest frontline workforce ecosystem, where he's betting on the gig economy and AI.

Saurav is refreshingly honest — he'll tell you he probably sold OkayGo too early, that failure still feels personal, and that the best salespeople don't actually sell. We get into gut versus data, why he sees AI as a tailwind for frontline workers rather than a threat, and the small, almost secret habit he's picked up to stay calm and curious — humming a song to himself.

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.