The Diary of a CEOClasspass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia | E141
CHAPTERS
- 2:20 – 6:00
Purpose Ignited: Discovering Dance and Early Identity Struggles
Kadakia explains how an impromptu dance at age five became her lifelong ‘light’ and refuge from feeling like an outsider as an Indian girl in a largely white American town. She describes the trauma of not fitting in, the grounding role of Indian dance, and how early experiences forged her hunger to live authentically and make others feel something.
- •Childhood dance performance at a wedding showed her the power of moving an audience (emotional influence, connection).
- •Dance made her feel like the most whole and authentic version of herself, unlike most social settings.
- •Growing up as one of the only Indian kids, she internalized her parents’ discomfort and endured bullying about smell, food, and appearance.
- •Dance became a protective ‘light’ against deep identity wounds; without it, she believes the trauma may have been overwhelming.
- •Her lifelong fight has been to be herself in any setting, rejecting limiting labels and boxes.
- 6:00 – 15:00
Immigrant Expectations, Conformity, and When to Rebel
She outlines the traditional expectations her immigrant parents had—elite education, stable profession, marriage—and how she first complied before choosing to rebel. The discussion with Bartlett explores the tension between pleasing others and pursuing fulfillment, and how society’s narrow success scripts can make life feel small and hopeless.
- •Parents expected doctor/lawyer/engineer paths and early marriage with domestic competence.
- •She initially conformed: top grades, MIT, Bain, doing what was ‘expected’ while excelling.
- •Realization that hitting external milestones without passion leads to an inner sense of emptiness.
- •Distinction between rebelling for ego vs rebelling for purpose; she sees her rebellion as fighting for passion and service.
- •Framework: consciously decide when to conform (to gain skills/resources) and when to rebel (to live authentically).
- 15:00 – 24:30
Leaving Bain: Performance Review Shock and Redefining Success
Kadakia recounts the pivotal performance review where a manager bluntly questioned whether she wanted to be a consultant, initially wounding her but ultimately catalyzing self-honesty. She describes the conflict between a demanding consulting career and her life as a choreographer, and how that led her to seek a more flexible role at Warner Music.
- •Typical Bain path was three years then business school; she didn’t want to do an MBA.
- •She relentlessly performed at 150% but felt no ‘fire’ for client work.
- •A missed client meeting to perform at Aishwarya Rai’s Madame Tussauds unveiling prompted criticism in her review.
- •The manager’s question—“Is this the job you really want?”—forced her to admit she did not want that life.
- •She chose a more nine-to-five style role at Warner Music to free evenings for dance and early entrepreneurial experiments.
- 24:30 – 35:00
Building Confidence Through Small Wins and Finding an Entrepreneurial Identity
While at Warner, she launched and scaled an Indian-American dance company, discovering her leadership and entrepreneurial instincts. A career-exploration trip to San Francisco exposed her to founders for the first time and planted the seed that she could become one herself, leading her to ‘give herself two weeks’ to find a tech idea.
- •Dance shows in New York grew from 150 to 1,000 attendees, building experiential proof of her capabilities.
- •She emphasizes that confidence is built through small, successive steps, not giant leaps.
- •San Francisco trip introduced her to startup culture and entrepreneurs, radically expanding her sense of what was possible.
- •Upon returning, she set a deliberate two-week window to brainstorm startup ideas, priming her mind to spot problems worth solving.
- •Core driver was always purpose: willingness to sacrifice evenings, sleep, and comfort came from wanting to make an impact.
- 35:00 – 52:00
Spotting the ClassPass Problem and Taking the Leap
Back in New York, a frustrating experience trying to book a new ballet class intersected with her fresh exposure to tech, inspiring the initial concept for what became ClassPass. She explains how her unique background (dance obsession plus MIT/Bain training) made her feel destined to tackle the problem, and how years of disciplined saving gave her three years of runway to quit her job.
- •Struggled for two hours to find and book a ballet class—poor information, clunky booking, uncertainty.
- •She connected this pain point to models like OpenTable and Seamless that streamlined discovery and booking.
- •Recognized her rare combination of deep domain passion (dance) and analytical/business training.
- •Calculated, with her father, that her savings allowed a three-year full-time attempt at building the company.
- •On quitting Warner, she emailed senior execs; the vice chairman, a former Bain consultant, immediately offered $10k and an incubator intro, validating the power of ‘invisible PR’ from always doing good work.
- 52:00 – 1:09:00
The Brutal Early Years: False Success Signals and a Failing Product
Kadakia describes the first three years of ClassPass as a grinding struggle marked by a polished but ineffective product, flattering press, and almost no revenue. She details burning through around half a million dollars, realizing that their OpenTable-style model ignored the psychology of fitness, and the soul-searching moment when even free classes couldn’t drive usage.
- •Initial product mimicked OpenTable for fitness: search and book single classes at studios.
- •Critical flaw: everyone must eat, but not everyone must (or wants to) work out; fitness is aspirational and often fear-laden.
- •Despite Techstars, followers, and an Inc. Magazine cover, actual transactions were ‘crickets’—no product-market fit.
- •A desperate move to offer free classes still failed to generate meaningful bookings, proving the model was wrong.
- •This failure forced her to shed ego, stop clinging to the original idea, and become truly entrepreneurial—comfortable ‘breaking’ what they’d built to chase the real problem.
- 1:09:00 – 1:18:00
Pivoting to Variety: The Passport, Subscription, and Product–Market Fit
By finally spending time in studios and talking to users, the team discovered that both sides wanted something different: studios were happy to offer free trials, and customers loved sampling varied workouts. A ‘Passport’ product letting users try 10 different classes in 30 days accidentally revealed a craving for variety, leading to the recurring subscription that became ClassPass.
- •Shifted from sitting in an office to visiting studios and interviewing owners and users.
- •Studios were already offering free first classes and wanted new customers; users were intimidated and needed friction reduced.
- •Created ‘The Passport’: 10 different classes in 30 days for a flat fee, intended as lead-gen for studios.
- •Users tried to re-purchase the Passport monthly; they valued variety more than settling into a single studio.
- •This behavior inspired the subscription ‘class pass’ concept, tested with ~50 users in June 2013, which quickly outperformed all other products and drove exponential growth.
- 1:18:00 – 1:31:00
Personal Cost: Loneliness, Burnout, and Rebalancing Through Goal Setting
As ClassPass finally took off, Kadakia realized the rest of her life—health, relationships, creativity—had withered. Often alone on holidays and barely dancing or working out herself, she hit an emotional low that pushed her to design a goal-setting framework spanning all life domains, which rapidly changed her trajectory.
- •First years of building were extremely intense: 80-hour weeks, missed weddings and family events, near-total social isolation.
- •Holidays were emotionally painful because work couldn’t anesthetize her loneliness when others were with loved ones.
- •Just as she ‘caught lightning in a bottle’ with ClassPass, she saw her health, friendships, and romantic life were in disarray.
- •Created a structured goal-setting ritual, writing down dreams across categories (career, love, health, dance, etc.).
- •Within six months she had relaunched a major sold-out dance show and met her future husband; she emphasizes writing goals and acting on them as transformative.
- 1:31:00 – 1:42:00
Manifestation, Money, and Living a Purpose-Led Life
The conversation broadens into how intention shapes opportunity and why chasing money and status without purpose misleads people. Kadakia advocates for ‘going towards purpose’ as a guiding principle and offers a practical question—how would you spend tomorrow if money were no object?—to help listeners surface their own calling.
- •She believes setting clear intentions makes doors open, aligning with the idea of manifestation.
- •Warns that when you lack a ‘why’, you drift toward money, fame, and power instead of passion and service.
- •Society’s structures (not just motivational quotes) push people into nine-to-five survival rather than purpose-led living.
- •Advises asking: if you had all the money you needed, what would you actually do with your day?
- •ClassPass itself was partly designed to give others a taste of that ‘light’ through accessible, variety-filled movement experiences.
- 1:42:00 – 1:56:00
Leadership Evolution: Delegation, Stepping Down as CEO, and New Problems to Solve
As ClassPass scaled globally and reached unicorn status, Kadakia found herself drained by operational CEO work and far from customers and product. She reflects on learning to delegate, hiring strengths to offset her weaknesses, and eventually handing the CEO role to someone better suited to that stage while she looks ahead to new missions.
- •Early leadership style: high energy, high expectations, giving people freedom to show their potential rather than boxing them in.
- •Learned to hire and delegate aggressively so she could focus on tasks that leveraged her ‘magic’—vision, product, customers.
- •By 2016–17, daily life as CEO was dominated by investor relations, legal, HR, and global operations, which she found uninspiring.
- •Recognized misalignment between her strengths and the CEO role at that scale, so she installed a new CEO in 2017.
- •Views stepping away as bittersweet—like a child leaving home—but necessary to free herself to face new, as-yet-unknown problems in the world.
- 1:56:00
Family, Partnership, Therapy, and Designing a Whole Life
In the later segment, Kadakia discusses building a marriage and family alongside ambition, emphasizing communication, joint goal-setting, and flexibility. She also touches on using therapy after the pandemic and new motherhood to process identity shifts, and ends by reiterating her core belief in aligning with purpose and being unafraid to change.
- •Husband Nick, a high-achieving law firm partner, often joined her on overseas expansions, sharing in the ClassPass journey.
- •They regularly align on family goals—schooling, travel, careers—to balance two demanding ambitions with parenting their son Zayn.
- •When individual and family goals conflict, they consciously ‘iterate’ on arrangements, trying new approaches for six months rather than remaining stuck.
- •She frames therapy as ‘personal training for the mind’, which helped her after having a baby just before COVID and facing business collapse.
- •Closing reflection: when she’s not aligned with her purpose, she feels sad; intentional choices toward service, creativity, and love are what maintain her characteristic positivity.
