TThe Diary of a CEO
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09 May 2022

Classpass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia

6Frameworks
10Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster1:02:00

ClassPass's Billion-Dollar Valuation Was Not Kadakia's Cash Exit

The host says ClassPass was valued above $1 billion in a 2020 funding round, then asks how that changed Kadakia's life. Kadakia clarifies that the company remained private, had not been sold, and her stake was still in it; she says the valuation mattered to her mainly as a visible signal to women and Indian girls rather than as money already realized.

  • The billion-dollar figure discussed was a private-company valuation
  • Kadakia explicitly says the company had not exited at the time of the interview
  • Her stake remained in the company rather than being described as cashed out
  • She treats the reported 100 million workout hours as a more meaningful impact measure
  • The host supplied the valuation claim and Kadakia did not dispute it

we haven't exited so like the company hasn't been sold yet

Payal Kadakia · 1:02:00

what you should run towards is making an impact

Payal Kadakia · 1:02:30
#valuation#classpass#unicorn#impact

Story· 8

Story02:00

Dance Gave Kadakia a Place Where Her Whole Identity Fit

Kadakia says dance made her feel authentic and connected from early childhood. She describes feeling divided between an American school where few people shared her Indian heritage and parts of an Indian community where other aspects of her life did not fit; dance, especially Indian dance, let those parts coexist.

  • Kadakia remembers dance as a form of connection and service from about age five
  • She says classmates mocked differences including her food and appearance
  • She felt she showed only one part of herself in many settings
  • Dance became a place where she felt grounded and whole

i felt like the most whole version of who i was

Payal Kadakia · 03:30

everyone wanted to box me into something and i just refused to be boxed

Payal Kadakia · 06:00
#dance#identity#belonging#childhood
Story12:30

The Bain Review Kadakia First Heard as Failure

After Kadakia missed a client meeting for an important dance performance, her manager later asked whether consulting was really the career she wanted. Kadakia says her first response was to prove she was good enough, but reflection changed the meaning of the comment: the manager was right that she did not want that life.

  • The client meeting and dance performance were scheduled for the same time
  • Kadakia received permission to attend the performance
  • She initially interpreted later feedback as a challenge to her competence
  • Reflection separated being capable at the job from wanting the career

is this the job you really want

Payal Kadakia, quoting her manager · 13:30

the more i started thinking about that the more i realized she was right

Payal Kadakia · 14:00
#career#feedback#consulting#self-awareness
Story26:30

The 36 Hours That Primed Kadakia to See the ClassPass Opportunity

Kadakia says a trip to San Francisco introduced her to entrepreneurs for the first time and prompted her to give herself two weeks to find an idea. Thirty-six hours after returning, a frustrating two-hour search for a ballet class landed while she was actively looking for a problem she could solve.

  • Kadakia felt her demanding work and dance schedules were on a collision course
  • Meeting entrepreneurs made entrepreneurship feel like an available path
  • She deliberately entered a short idea-search period
  • The class-booking problem arrived when her attention was primed to treat it as an opportunity
  • She believed her dance, analytical, and community experience gave her relevant founder fit

what if i could be an entrepreneur let me give myself two weeks to think of an idea

Payal Kadakia · 28:00

i know i'm the right person to build this

Payal Kadakia · 28:30
#classpass#entrepreneurship#problem-discovery#timing
Story33:30

Why Kadakia Believes a Warner Executive Backed Her Immediately

On the day Kadakia resigned, Warner Music Group's vice chairman asked to hear her idea, then offered $10,000 and an incubator introduction. Kadakia believes her record of good work mattered alongside the idea and the era's enthusiasm for entrepreneurship; the host independently relates making similar investment decisions based on employees' prior performance.

  • The vice chairman had met Kadakia only a few times
  • He offered both capital and an incubator introduction
  • Kadakia says her reputation as a reliable worker had reached him
  • The investment was support for her potential, not proof that the first product would work

reputation does follow you

Payal Kadakia · 34:30

at the end of the day he believed in me

Payal Kadakia · 35:00
#reputation#investment#career#classpass
Story49:00

Kadakia Mistook a Founder Marathon for a Creative Sprint

Kadakia says the first three years of building the company left her exhausted and lonely even though the mission felt fulfilling. She was accustomed to intense preparation for dance shows that ended on a fixed date; startup intensity did not end, and work became a closed circuit that displaced family events, friendships, health, and dance.

  • Kadakia says she missed weddings and family events during the early company years
  • Her roommate was often the only person she saw outside work
  • A dance production's intensity ends after the show, unlike the company workload she experienced
  • She describes fulfilment, exhaustion, and loneliness as coexisting
  • Her account is personal and does not establish that such sacrifice is required for founders

was i exhausted yes was i lonely yeah

Payal Kadakia · 49:30

it's a marathon not a sprint

Payal Kadakia · 50:00
#founder-life#loneliness#burnout#relationships
Story50:30

Success Exposed the Rest of Kadakia's Life as Neglected

Just as Kadakia felt sure ClassPass had found momentum, facing the holidays alone forced her to assess what work had displaced. She says her health, dance, friendships, and romantic life were in poor shape, so she wrote goals across those areas; six months later, she reports having completed the dream list written on a Post-it note.

  • Kadakia says work had previously helped her avoid confronting loneliness
  • Early subscription momentum gave her space to notice neglected priorities
  • She set goals for relationships, dance, health, and ClassPass
  • She met her future husband a month later and staged a major dance show within six months
  • The sequence is her personal account and does not prove that writing goals causes those outcomes

i want to make sure my priorities are more reflective of the human i want to be

Payal Kadakia · 51:30

sometimes just writing down those dreams is the most important thing

Payal Kadakia · 53:00
#goals#priorities#loneliness#whole-life
Story59:00

Leaving ClassPass Felt Like Loss and an Opening

After roughly a decade working on the same problem, Kadakia says she wanted to make room for other problems and future possibilities. Losing access to her long-standing ClassPass email felt especially painful, but creating a new address also made her ask what she wanted to put into the newly open part of her life.

  • Kadakia describes the departure as bittersweet rather than a rejection of the company
  • She believed the earliest product-discovery work was largely complete
  • She compares the separation to watching a child move into a new stage
  • Removing the old inbox reduced noise and created room to consider what came next

if you're kind of stuck in the past you don't even welcome the doors

Payal Kadakia · 59:30

the hardest day was when i stopped getting my class pass email

Payal Kadakia · 1:00:00
#classpass#founder-transition#identity#loss
Story1:06:30

Why Kadakia Tried Therapy During the Pandemic

Kadakia says she had a baby six weeks before the pandemic and later sought some therapy after a year of motherhood at home while her company had come to a halt. She describes wanting help talking through a mental state she could not make sense of and personally recommends therapy, comparing attention to the mind with guided physical training; this is her experience and analogy, not medical advice.

  • Childbirth, isolation, and business disruption occurred close together in Kadakia's account
  • She sought therapy to talk through a mental state she found difficult to interpret
  • She describes the pandemic as radically different from her prior life
  • Her fitness-instructor comparison is a personal analogy rather than a clinical claim
  • The transcript does not provide a diagnosis or describe a specific treatment outcome

i had just gone to therapy to just start talking to somebody

Payal Kadakia · 1:07:00

you need to work on your mind sometimes

Payal Kadakia · 1:07:30
#therapy#pandemic#motherhood#mental-health

Takeaway· 1

Takeaway17:00

A New Community Made Kadakia's Career Transition Feel Possible

Kadakia says comparison with former Bain colleagues made her feel as if she were falling behind. A growing artistic and Indian American dance community gave her another place to belong and another basis for identity, reducing the hold of the professional group she was leaving.

  • Former colleagues followed prestigious academic and career routes
  • Comparison made Kadakia feel she had taken a step backwards
  • Her dance community offered belonging on different terms
  • She argues that people can choose communities suited to different phases of life

instead of constantly being around people i felt less than i went and found a community i belonged in

Payal Kadakia · 17:30

the people you surround yourself with are your choice

Payal Kadakia · 18:30
#community#career-change#belonging#comparison