
Classpass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia | E141
Steven Bartlett (host), Payal Kadakia (guest)
In this episode of The Diary of a CEO, featuring Steven Bartlett and Payal Kadakia, Classpass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia | E141 explores from Lonely Consultant To Unicorn Founder: Payal Kadakia’s Purpose Journey In this conversation, ClassPass founder Payal Kadakia unpacks how a childhood love of dance and the pain of not fitting in became the fuel behind a billion‑dollar company.
From Lonely Consultant To Unicorn Founder: Payal Kadakia’s Purpose Journey
In this conversation, ClassPass founder Payal Kadakia unpacks how a childhood love of dance and the pain of not fitting in became the fuel behind a billion‑dollar company.
She traces her path from immigrant expectations and elite consulting to quitting her job, enduring years of failed products, and finally discovering the subscription model that unlocked explosive growth.
Kadakia emphasizes being ‘mission-obsessed, not product-obsessed’, the importance of financial and emotional preparation before leaping, and the high personal costs of entrepreneurship on health, relationships, and loneliness.
Now a mother and no longer CEO, she reflects on redefining success around purpose, time, and family, while still believing everyone has a calling beyond a conventional nine‑to‑five.
Key Takeaways
Anchor your career decisions in a deeply felt purpose, not external expectations.
Kadakia’s ‘light’ was the feeling she got from dance—making others feel something and being her most authentic self. ...
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Use conformity strategically, then consciously choose when to rebel.
She ‘earned her stripes’—elite education, Bain, Warner—meeting her parents’ and society’s expectations while quietly building savings, skills, and credibility. ...
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Treat failure as data and be mission-obsessed, not product-obsessed.
Her first product burned through roughly $500,000 and a year of work, garnered press and followers, but almost no bookings—“false signals of success. ...
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Talk to real customers and watch what they actually do, not what you hope they’ll do.
Early on, Kadakia’s team hid behind screens in an incubator instead of being in studios. ...
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Design your finances intentionally so money doesn’t suffocate your purpose.
Knowing money is the main excuse people give for not pursuing purpose, she lived lean, skipped travel and shopping, and built a savings buffer. ...
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Success in one domain at the expense of all others is unsustainable.
Three years into ClassPass, just as product-market fit arrived, she realized she had no time for friends, family, health, or romance and often dreaded the holidays because they exposed her loneliness. ...
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Know your unique ‘magic’ as a founder and be willing to hand over titles.
As ClassPass scaled globally, Kadakia found herself mired in investor calls, legal issues, and HR—work that drained her and pulled her away from product, customers, and creative problem-solving. ...
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Notable Quotes
“Everyone wanted to box me into something, and I just refused to be boxed.”
— Payal Kadakia
“You can have a life and make your people proud, but you're gonna be on the other side of it and feel empty.”
— Payal Kadakia
“I spent half a million dollars building a product that didn't work.”
— Payal Kadakia
“Be mission-obsessed, not product-obsessed.”
— Payal Kadakia
“If you go towards purpose, even if you’re rebelling, I guarantee your life will be more fulfilling.”
— Payal Kadakia
Questions Answered in This Episode
You described the first product’s failure as the moment you truly became an entrepreneur—what specific internal beliefs or habits did you have to kill in yourself during that pivot that you haven’t talked about publicly?
In this conversation, ClassPass founder Payal Kadakia unpacks how a childhood love of dance and the pain of not fitting in became the fuel behind a billion‑dollar company.
Get the full analysis with uListen AI
When users tried to repurchase the one-month Passport repeatedly, how did you quantitatively decide it was evidence for a subscription model rather than an edge case—what data or thresholds convinced you?
She traces her path from immigrant expectations and elite consulting to quitting her job, enduring years of failed products, and finally discovering the subscription model that unlocked explosive growth.
Get the full analysis with uListen AI
You’ve said money is the biggest trap keeping people from purpose; looking back, is there any financial risk you regret not taking earlier or later in the ClassPass journey?
Kadakia emphasizes being ‘mission-obsessed, not product-obsessed’, the importance of financial and emotional preparation before leaping, and the high personal costs of entrepreneurship on health, relationships, and loneliness.
Get the full analysis with uListen AI
You stepped down as CEO when the job no longer matched your ‘magic’—what warning signs should other founders look for to know it’s time to replace themselves rather than just push through burnout?
Now a mother and no longer CEO, she reflects on redefining success around purpose, time, and family, while still believing everyone has a calling beyond a conventional nine‑to‑five.
Get the full analysis with uListen AI
If you were designing a school curriculum informed by your own story, how would you practically teach teenagers to find and test their ‘light’ so they don’t wake up at 40 living only for others’ expectations?
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Transcript Preview
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I think society goes, success is get this job, get married, get a house. What does that do to you? It just really makes your life feel small. The founder of ClassPass.
A monthly fitness program. A billion-dollar founder. Payal Idarkia.
When I would watch my parents not really fit in, it sort of made me realize, maybe I don't fit in, and then be told I smelled or I didn't belong somewhere. Everyone wanted to box me into something, and I just refused to be boxed. I spent half a million dollars building a product that didn't work. Was I exhausted? Yes. Was I lonely? Yeah. I missed family things, I missed weddings. I- I was just not around. I have learned at this point, like, time means more to me than money. I want to make sure my priorities are more reflective of the human I want to be in my life. If you go towards purpose, I guarantee your life will be more fulfilling.
Do you believe that everybody has a purpose beyond the nine to five?
I do.
How do you find it?
So first of all ...
So without further ado, I'm Steven Bartlett, and this is The Diary of a CEO: USA Edition. I hope nobody's listening, but if you are, then please keep this to yourself. Payal, when I read someone's story, one of the first questions I try and answer when I'm reading through their, especially their early years, is I'm trying to identify what it is that made them either an anomaly or hungry. I have a kind of a thesis that much of people's drive and their ambition, especially the people that I sit here with, comes from kind of, some kind of pain or trauma or early experience that molded them.
Right.
So my question to you is, what made you hungry?
You know, when I was younger, I got to taste something that was so magical, which was dance. And it was this place in my life that it wasn't about the physicality of actually dancing. It was the ability to make other people feel through something that I did, and to be able to realize that as a human being, you can have that type of influence, power, connection to other people, and to feel that when you are four or five years old was just this magical experience for me that honestly nothing else in my life could compare to it, and once I uncovered that, I always wanted to feel that in anything I did, and I strived in all the work I did and all of, you know, the different careers I've had in my life and the different, you know, art I've done, I've strived always to go back to that intention of how do I give to others and make them feel something in their life? And that's really been this anchor for me and its purpose at the end of the day.
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