Interview
Classpass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia | E141
- Payal Chhadva's ambition was rooted in early trauma regarding not fitting in as an Indian-American girl, often facing isolation and being told her food "smelled" or she didn't belong in her community.
- Her "light" or purpose was discovered at age five when dancing at a wedding, an organic performance that made her feel the most authentic and whole version of herself.
- She initially conformed to societal and parental expectations of becoming a doctor, lawyer, or engineer, and eventually working as a high-performing management consultant at Bain & Company for three years.
- The catalyst for leaving Bain occurred when a boss questioned her commitment during a performance review, leading Chhadva to realize she was unhappy despite high performance and that the lifestyle would require sacrificing her passion for dance.
- She moved to Warner Music Group to gain flexibility for her dance career, where she began building confidence by organizing successful dance shows for audiences of 150, then 1,000, and eventually a sold-out show at Alvin Ailey.
- Chhadva's decision to become an entrepreneur was triggered by a trip to San Francisco where she met founders, followed by a personal frustration finding a way to book a single ballet class online.
- She leveraged her "invisible PR" from her previous work ethic to secure a $10,000 investment check from the Vice Chairman of Warner Music Group and an introduction to an incubator upon quitting her job.
- ClassPass's initial product failed because it treated fitness bookings like restaurant reservations, ignoring the psychological difference where working out is aspirational rather than a daily necessity.
- The company lost half a million dollars building an early product that did not work, marking a period where Chhadva faced failure for the first time in her career.
- Chhadva shifted from being product-obsessed to mission-obsessed, realizing through customer feedback that people desired variety in their workouts rather than a single studio membership.
- The company pivoted to a "Discovery Pass" (later ClassPass), a subscription model allowing users to try 10 classes over 30 days, which proved the demand for variety and became the core business model.
- Chhadva spent three years "stumbling" before achieving product-market fit, a period marked by intense work hours (6 AM to 10 PM), missed family events, and significant loneliness.
- At age 33, realizing she had achieved professional success but neglected personal health, relationships, and joy, she instituted a deliberate goal-setting method to realign her priorities.
- Within six months of implementing new goals, Chhadva met her husband, sold out a 1,000-seat dance show, and achieved her fitness and professional objectives without feeling guilty about trade-offs.
- She stepped down as CEO in 2016/2017 because administrative duties like investor relations and HR issues no longer aligned with her intrinsic drive to solve problems and innovate on the product.
- ClassPass reached a valuation of over $1 billion in 2020, a milestone Chhadva views primarily as a representation of impact (100 million workout hours booked) and a symbol for women and minority entrepreneurs.
- Chhadva maintains her stake in the private company and continues to view her future work through the lens of solving new global problems rather than seeking financial exits alone.
- She attributes her work-life balance and relationship success to bringing her partner along on the entrepreneurial journey and treating family planning with the same iteration and flexibility as a business strategy.
- Chhadva engages in therapy to manage mental blocks, comparing it to physical training for the mind to identify and overcome internal obstacles.
- Her forward-looking advice is to identify one's "why" early, rebel for a purpose rather than just against expectations, and view failure as a data point rather than a definition of inadequacy.