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The Diary of a CEOThe Diary of a CEO

Classpass Founder: Quitting My 9-5 Led To A $1 Billion Business: Payal Kadakia | E141

This episode is part of our USA series, over the coming weeks you will get to see some incredible conversations with guests the likes of which we’ve never seen before. Bringing more value, more incredible stories, and more world-beating expertise. Payal is the founder of Classpass, the billon dollar app that’s been the ticket to every skill and passion for its millions of users. Today she shares exactly how she got there. The sheer determination with which she ruthlessly sets her goals and priorities, and then systematically chases after them with everything she’s got, was hugely inspiring to me, and I’m sure it will be to you too. 00:00 Intro 01:26 What made you different? 10:18 Battling between your passion and 9-5 14:43 Rebelling for your purpose 18:24 Changing careers and finding new communities 20:54 Confidence, purpose, and drive to success 26:13 Why did you start ClassPass? 40:18 What difficulties did you face starting your business? 52:06 Living in line with your values 54:57 What were you like as a manager? 59:05 Why did you step away from ClassPass? 01:03:07 Work and family balance 01:06:53 Therapy sessions 01:09:00 Our last guest’s question Payal: https://twitter.com/payalkadakia https://www.instagram.com/payal Payal's book: https://www.amazon.co.uk/LifePass-Groundbreaking-Approach-Goal-Setting/dp/1399706756 Listen on: Apple podcast - https://podcasts.apple.com/gb/podcast... Spotify - https://open.spotify.com/show/7iQXmUT... FOLLOW ► Instagram: https://www.instagram.com/steven/ Twitter: https://twitter.com/SteveBartlettSC Linkedin: https://www.linkedin.com/in/steven-ba... Sponsors: Huel - https://my.huel.com/Steven Myenergi - https://bit.ly/3oeWGnl Vodafone Business - https://bit.ly/3NIM35n https://bit.ly/3AuPKsA Location courtesy of The Nightfall Group: www.nightfallgroup.com

Steven BartletthostPayal Kadakiaguest
May 9, 20221h 12mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:26

    Intro

    1. SB

      Could you do me a quick favor if you're listening to this? Please hit the follow or subscribe button. It helps more than you know, and we invite subscribers in every month to watch the show in person.

    2. PK

      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.

    3. SB

      A monthly fitness program. A billion-dollar founder. Payal Idarkia.

    4. PK

      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.

    5. SB

      Do you believe that everybody has a purpose beyond the nine to five?

    6. PK

      I do.

    7. SB

      How do you find it?

    8. PK

      So first of all ...

    9. SB

      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,

  2. 1:2610:18

    What made you different?

    1. SB

      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.

    2. PK

      Right.

    3. SB

      So my question to you is, what made you hungry?

    4. PK

      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.

    5. SB

      And that started at five years old?

    6. PK

      Yeah. When I was really young.

    7. SB

      With a dance at a wedding?

    8. PK

      Yeah, it was just a random dance performance that for some reason I started dancing, and everyone started watching me, and I, it wasn't anything that was a, uh, structured performance by any means. It was very much just this organic thing that came out of me, and I really just loved it. And I realized actually in a, in a deeper way that the other part of the hunger came from when I danced and felt that feeling, I felt like the most authentic version of me, and I realized that I was in so many settings where I didn't always feel like I could be me. And whether that was, you know, being an Indian girl in the middle of a town where no one looked like me, or sometimes being with my Indian community but being in a town that where I was a cheerleader and I didn't fit in there, I realized that so many parts of me never felt whole, and I was always showing up with one little strand of me, one little strand of me there, here, and I felt when I performed and danced, especially Indian dance, I felt like the most whole version of who I was.

    9. SB

      The resistance you felt and the struggle you felt of bit- trying to, I guess, conform to two different communities at the same time, so tell me about trying to be an American in, in a town where there's, you know, 300 people at your school, and you're the only people of Indian heritage. How was that?

    10. PK

      I think one of the most interesting parts of it is so much of this comes from the parents, not really from the kids, and when I would watch my parents not really fit in, it sort of made me realize maybe I don't fit in. It was sort of this interesting way to look at my parents and know that they felt uncomfortable and then look at myself and be in different settings and realize, wait, I don't look like everyone else, and then be told I smelled or my food smelled or I didn't belong somewhere because my hair color was different, was just a very interesting place to be.

    11. SB

      Kids said that to you?

    12. PK

      Yeah. I rem- like, I mean, I talk about it in my book, but there were some, some really harsh moments, you know? And when you're young, you're, you're impressionable, right? Things can scar you for a very long time. And I think for me, the, the goodness was that I did have this place of dance that made me feel grounded and made me feel whole, because if I didn't have that, I think the trauma that I was probably going through by not fitting in would have just burned a hole so deep in me that I'm not sure how I would have been able to recover, but I had this light, right? And I think that's, you know, going back to what you were asking, it was the light that I saw that there is something beautiful out there for me to go and do for the world if I can just hang onto it and fight for it, and it was a fight for me to even hang onto whatever my identity was, right? I mean, we talk about our identities in, in all these labels, which I really don't love, like whether it's Indian-American CEO, whatever all these labels are. It was really just, I think my whole journey in my life-... was a fight to be myself in any setting and not have people tell me what to do. Right? I think we all struggle with that in our whole lives, and probably why I had to be a CEO, because I don't like (laughs) anyone telling me what to do.

    13. SB

      Mm-hmm.

    14. PK

      But it really stemmed because I think throughout my life everyone wanted to box me into something, and I just refused to be boxed.

    15. SB

      Did your parents want to box you into something?

    16. PK

      Of course. I mean, my parents, you know, they sacrificed everything to come to America. They obviously wanted my sister and I to have successful careers, which, you know, amounted to a few different industries, like be a doctor, a lawyer, engineer, or ... You know, and then the other part of it was get married, you know, obviously at like a normal age where you could cook for your (laughs) family and be a good wife. Right? These were sort of the, these were the expectations that were set in my life, and I think that's really the hardest part is when you are constantly brought in your life and saying that you need to live by the expectations of others. You end up either rebelling-

    17. SB

      Hmm.

    18. PK

      ... or you conform. And I always wanted to make my parents proud, so I knew I did what I felt was at the core part of the values, so for example, if it was getting education, I thought that was important too. I wasn't going to sit there and rebel from getting education. But there came a point in my career trajectory where I had to say, "Okay, like I have checked every box in this. Now I have to do it my way, with the way I really want to feel and not conform, and rebel." And I think that's really the whole formula of people knowing when to rebel and when to conform.

    19. SB

      You referenced that, um, you were looking for a different feeling after checking those boxes. What was the feeling you had when you were doing that job?

    20. PK

      I had trained myself my entire life to do well when people told me to hit this mark in my life. Right? I, and that's like, in a way, that's like how I developed the skills in my life to, to always propel myself and execute and make sure that, um, I was able to, you know, be responsible and move forward in everything I did. But, I felt no deep fire or passion or love towards it. Right? I wasn't jumping out of my bed to go (laughs) to my office to go and work-

    21. SB

      (laughs)

    22. PK

      ... for my clients. Right? I was doing what I had to because, you know, I knew it was, once again, expected of me.

    23. SB

      When you hear ... You must have friends that are living a, a life that is expected of them, and you can start to see as the, the years go on the consequence of living a life that is expected of you.

    24. PK

      Absolutely.

    25. SB

      So what would you say to those people? And what lessons have you learned about living a life expected of you?

    26. PK

      (laughs) I mean, that's not the way to have a fulfilled life. You can have a life, and you can probably check all the boxes and make your people proud in your life, but you're gonna be on the other side of it and feel empty. And that feeling of emptiness is the worst feeling anyone can ever have, and I think people come to it at different points in their life. They either come to it when they're 20 or they come to it when they're 50.

    27. SB

      Hmm.

    28. PK

      And that's because they haven't done the work to actually ask themselves, "What are the expectations you want for your own life?" And that's the problem. I think we're never taught that, right? No one's ever asked us what we want for our own lives, and I think society goes and tells us, "Okay, success is get this job. Success is get married, get a house, have kids." You know? And especially for women, it's even, I think, even a bit more of a closed road. And that, what does that do to you? It just really, it, it makes your life feel small. Right?

    29. SB

      Mm-hmm.

    30. PK

      Because it makes you feel like you can't get past it to go and live for your dreams, and ultimately, you know, and I've been there in my life where I have felt like the road has closed in, and it's left me feeling hopeless. And that's the worst place in the world to be, is feeling hopeless. The best thing you could do is feel like you can go and do anything, change the world, and I think the more you taste it, the more you want more of it in your life.

  3. 10:1814:43

    Battling between your passion and 9-5

    1. PK

    2. SB

      At that phase in your life, were you battling somewhat with your north star, that light you referenced earlier, which was dancing, but also your, I guess, your nine-to-five?

    3. PK

      (laughs) Yeah.

    4. SB

      And I want ... Tell me about that battle and how dance ultimately ended up winning.

    5. PK

      I remember always having this bounce in my step. Like I would walk to work in the middle of New York City choreographing in my head, listening to the song I was performing. Like I, I, in a weird way, was like embodying this life that, of what I wanted to be. And then I would get to the office, and I would do my work, and you know, once again, like I, I love the Steve Martin quote of, "Be so good they can't ignore you." Like, whatever work I've, I do in my life, I will do 150% if I say yes. But, I knew that something was wrong. I never, I didn't want to live like that. I didn't want to feel like I was hiding so much of who I was. And as my nine-to-five, which by the way in consulting isn't a nine-to-five.

    6. SB

      Yeah. (laughs)

    7. PK

      You work like 80 hours a week. I mean, that was my life. And I, as I realized that if I wanted to commit to that career path, that that 80 was probably gonna go to 90, it was gonna go to 100, was going to be traveling, and I was going to have to say, "No," more and more to the thing I loved, I just realized I wasn't willing to make that trade-off. And I think that's sometimes the hardest thing people have to think about is what are you sacrificing, and what's the trade-off in your life that you're making? And I just wasn't willing to make it at that point, and I, uh, I had done so much in my life at that point where, um, I felt like I had achieved, according to everyone else, enough to start taking a little bit of a path to being rebellious. Right? And I think that's really when I started to do a lot of work to say, "What can I do to bring all parts of me to the table?"

    8. SB

      When you make that decision to leave Bain & Company-

    9. PK

      Yeah.

    10. SB

      ... a managing, management consulting firm in New York-

    11. PK

      (laughs)

    12. SB

      ... was there like a, a series of catalytic sort of moments or pivotal moments near the end of your time there that made you think, "Oh, fuck this."

    13. PK

      (laughs)

    14. SB

      You know, like I, I, I read about a meeting you had-

    15. PK

      Yeah.

    16. SB

      ... a performance review.

    17. PK

      Yeah. So, it's literally the opening-

    18. SB

      Is that- hmm.

    19. PK

      ... um, of my book. But, you know, a few, a few things happened, I would say. So, first of all, most people stay in consulting, like, at this, this job for about three years, and then you go off to business school. It's sort of the usual route people take. So, I was in my third year there. And a few people can kind of stay on and just continue there. I really wasn't interested in going to business school at the time. I wanted to live. I wanted to, like, be in New York City and feel the energy of it. And so, in my third, in my third year, I had a performance at, um, in the middle of Times Square for th- for this big, uh, unveiling of Aishwarya Rai's Madame Tussauds str- statue, which was an important thing. And Aishwarya Rai is one of my icons, especially as a dancer, and she's a huge Bollywood actress. And the week before, a client meeting gets scheduled at the same time as my performance. And I'm, you know ... My clients are big clients. These aren't, these are Fortune 500 companies. (laughs) These aren't small clients by any means, and, and we're meeting, like, the CEOs, you know, CFOs of the company. And, um, I remember talking to my boss saying, "Hey, you know what? I really want to go to the performance. I'm not, like, a big part of this meeting. Is it okay if I miss it?" And we talked about it really briefly. It wasn't a big deal. I didn't feel bad about it. I went to the performance, it went, it went well. A few months later, we're sitting down talking about, you know, review and she's, like, giving me feedback. And she says this thing to me which just triggered me, and it was, "Is this the job you really want? Like, I don't think that you want to be a consultant." And I took that in my heart as, "Oh my gosh, she doesn't think I'm good enough," right? And I just kind of went through how throughout my life, I've been taught to be type A, everyone tell me I've done a good job. And so my initial reaction to her saying that to me was, "I'm going to prove to you how good I am," right?

    20. SB

      Mm-hmm.

    21. PK

      That's like the natural type A reaction-

    22. SB

      Mm-hmm.

    23. PK

      ... is to say, "No, no, what do you mean? Like, I love this job. I really want to be here." And the more I started thinking about that, the more I realized she was right. I didn't want to be there. It was not the life I wanted. It was not the career I wanted. And that's when I decided to start looking at other jobs that would give me a bit more of the flexibility I wanted in my day-to-day, but still pay the bills.

  4. 14:4318:24

    Rebelling for your purpose

    1. PK

    2. SB

      And that's when you moved over to MTV?

    3. PK

      I went to Warner Music Group.

    4. SB

      W- Warner, oh right, okay.

    5. PK

      Yeah.

    6. SB

      Um, there's this really interesting balance that I see in you, like, which c- clearly shifts in your life, where you, you feel like you're a, um ... And correct me where I'm wrong here. But you're quite a good, like, conformist in terms of expectation, and then slowly rebellion starts to creep in. And it was just, just had me thinking about, like, the probably ... if there is a right balance of conformity and rebellion in our life, because conformity makes sense, you know, in some regards. You can't just be a total rebel.

    7. PK

      Right, right.

    8. SB

      You know, we'd all be living out in the desert or something.

    9. PK

      Right.

    10. SB

      But just the interesting balance I see in people like you, like me, of ... I mean, a lot of them start as kind of conformists or a little bit more people pleasing, especially first-generation immigrant families.

    11. PK

      Right.

    12. SB

      And then that fails them-

    13. PK

      Yeah.

    14. SB

      ... in terms of fulfillment, happiness, mental health, and then that's where the rebellion starts to ...

    15. PK

      I think that's the key. It's, it's rebelling for the right reason.

    16. SB

      Mm-hmm.

    17. PK

      If that makes sense? I always believe that I was rebelling for purpose.

    18. SB

      Right.

    19. PK

      Right?

    20. SB

      Yeah.

    21. PK

      And if you're rebelling for purpose-

    22. SB

      Hmm, it's a strong force.

    23. PK

      ... I think it's ... Exactly.

    24. SB

      Yeah.

    25. PK

      It's justifiable, right?

    26. SB

      Yeah.

    27. PK

      Dance wasn't something that was just, "Okay, Payal, go and do this because it's a hobby." Like, it, it was this place for me to bring together so much of my trauma actually from when I was younger. It was this place for me. And, and, you know, my dance company was this Indian American dance experience. And it was about me bringing together the Payal who got made fun of with the Payal who danced at her Indian festivals and bringing all of me together to say, "When the world doesn't want to accept the different parts of who I am, I'm going to show you what it can look like," right? Like, that's really a big part of what I realized in my journey, is when people have told me parts don't fit together, I find a way to put them together-

    28. SB

      Mm-hmm.

    29. PK

      ... and show you even a more beautiful experience, right?

    30. SB

      Mm-hmm.

  5. 18:2420:54

    Changing careers and finding new communities

    1. PK

    2. SB

      It's such a unappreciated, um, point of resistance for people that are trying to make an adjustment in their life. I hear it so much. People say, "I want to leave a situation, but I'm scared of losing the community that comes with that situation." That could be a city, it could be a job, it could be a partner.

    3. PK

      Right, right.

    4. SB

      Sometimes your lives become so intertwined that you think, "Well if, I lose this partner, if I lose this job or whatever, then I'm going to lose all of these people," and that really keeps people ...... trapped.

    5. PK

      I agree with that. That's-

    6. SB

      Really keeps people trapped.

    7. PK

      ... a really good point. Yeah. P- I mean, and you can find new communities, you know?

    8. SB

      Yeah.

    9. PK

      And I think you have to remember that the people you surround yourself with are your choice.

    10. SB

      Yeah.

    11. PK

      Right? And I've had different communities show up for me at different times in my life, right? For me, it was the different communities that made me the entrepreneur I was.

    12. SB

      Mm-hmm.

    13. PK

      It was my business community that helped me build ClassPass, but it was also this girl who was going to ballet classes every single day-

    14. SB

      Mm-hmm.

    15. PK

      ... with my, with my dancer friends who also was thinking about the f- the classes that they-

    16. SB

      Mm-hmm.

    17. PK

      ... people need to take in their life. And it was that unique combination of my traits combined with the different experiences I was having-

    18. SB

      Mm-hmm.

    19. PK

      ... that enabled me to build what I did ultimately.

    20. SB

      You talk about, so you, you managed to get a, now, a job you consider to be more of a nine-to-five, where you've got time in the evenings to, to dance, and you end up setting up your own sort of dance company. Um, how'd you get to th- from there to that pivotal trip to San Francisco that introduced you to the world of tech?

    21. PK

      Yeah. So, in those two years when I was at Warner Music Group, I started tasting leadership and entrepreneurship, right? I started tasting this idea of what life could look like when I was living to my own drum beat, right? And we put on a few shows in New York City during that time that, honestly, like just were so well received from people. The, the momentum of that, the, the feeling I felt for, of my community's support, it made me just start feeling confidence in my ability to go after my dreams, right? And I think this is an important part of the journey that we also forget is that, it's the confidence in the small stuff that actually-

    22. SB

      Mm-hmm.

    23. PK

      ... builds the confidence towards the big stuff, right?

    24. SB

      Mm-hmm.

    25. PK

      'Cause it's not, it wasn't, okay, Payal just decided to go quit her job one day and start a company. It was this series of small steps, right? It was putting on a show for 150 people that went well, then putting on a show for 1,000 people that went well, then saying, "Oh wait, let me think about my life in a bigger way," and that's sort of where I was at that moment. So, I wanted to explore new career paths that I could take, and that's why I decided to go out to San Francisco, and it changed my life.

  6. 20:5426:13

    Confidence, purpose, and drive to success

    1. PK

    2. SB

      The point you made about the way confidence is built I think-

    3. PK

      Mm-hmm.

    4. SB

      ... is so, so important because I think a lot of people think, they see people like you now, sat here, um, after all this, all you've achieved, and they think, "How do I get from where I am sat on this sofa, in this job that I'm in that I hate, to being her?" It seems like such a huge canyon I have to cross that it feels like you must be, uh-

    5. PK

      Mm-hmm.

    6. SB

      ... from another planet. So, uh, that f- f- when people see you at the finish line, it can sometimes be quite demotivating.

    7. PK

      Yeah.

    8. SB

      It seems like so. But what you've just said there is, in fact, there's these small, it's a staircase, small, one tiny step at a time building, like, subjective evidence in yourself that you, you can do a little bit more than you thought.

    9. PK

      That keeps you going.

    10. SB

      And I'm curious as to what makes people like you take, take that small step. And it sounds like it's, you're just driven, th- this purpose is dragging you.

    11. PK

      Purpose, 100%.

    12. SB

      Mm-hmm.

    13. PK

      If, if I wasn't driven to make an impact in the world, I wouldn't do it. I mean, l- you know, the, you know, yes, like I could go and get a good job and do all of that and live, like, the expected life and be fine. But that's not fire, right? That's not me taking my hours of 5:00 to 10:00 PM-

    14. SB

      Mm-hmm.

    15. PK

      ... after work and reserving studio space and getting girls together or, you know, working till 2:00, 3:00 in the morning to make reservations for people to get to class. Like, that's a very different why, right? And I think that's why I go back always to, how do you find that why? Like, what is that light that your life is always about? And I think, you know, and I, I feel very blessed that I found something that made me feel a sense of service so young, because nothing compares to it, you know? No, no amount of money, no amount of like, you know, whatever, press, or-

    16. SB

      Mm-hmm.

    17. PK

      ... you know, any of that is ever going to compare to the feeling of touching somebody's life.

    18. SB

      So many people in my, like, again, in my DMs are like, "How do I find my why?"

    19. PK

      Yeah.

    20. SB

      And, and it feels-

    21. PK

      Good question, good question.

    22. SB

      ... almost like a privilege, doesn't it-

    23. PK

      Absolutely.

    24. SB

      ... for people that have figured that out? And there's people, I don't know, that will be listening to this in the morning, washing the dishes, driving up and down the country in a delivery van, whatever it is, thinking, "I know I'm capable and deserving of more, but I just don't know what it is." I w- do you, do you believe that everybody has a, a w- a, a, a purpose beyond the nine-to-five?

    25. PK

      I do.

    26. SB

      Yeah?

    27. PK

      But-

    28. SB

      How, how do you find it?

    29. PK

      Yeah.

    30. SB

      Where is it?

  7. 26:1340:18

    Why did you start ClassPass?

    1. PK

    2. SB

      And how did you ... When was the moment ... 'Cause I- I read in, I read in your book, you know, there's certain pain points we encounter where we realize, "Okay, I can solve this problem, and the, the sort of my manifestation of the solution is, um, this app or this website." What was the problem that you encountered and when that made you think ClassPass is the solution?

    3. PK

      Yeah. So, I was, once again, training in ballet at the time. I- I, you know, I had my nine-to-five, but every day after work I would go and train in ballet. And I'd have my ballet clothes with me, and I'd been going to the same teacher for about six months at the time, and I wanted to try a new class. It was just, like, a very simple thing I wanted to do. I get onto, you know, my computer. I start browsing for this class. Two hours go by. It was just this terrible experience from a information standpoint, from, you know, not knowing what class to take, if it was, if it's, you know, close enough to me, what time it starts, how do I register? And that's when I started looking at other models that existed. So, there were things, you know, in the US like OpenTable-

    4. SB

      Mm-hmm.

    5. PK

      ... SeamlessWeb, that just made this type of information so accessible and so easy and convenient for a customer, um, that I started thinking, "What if I could do this for classes? And therefore get people to get an hour out of their life that was out of their routine to go and do something fun and exciting?" So, that was really where it started.

    6. SB

      Even that, you kind of glossed over that, but that's pretty extraordinary-

    7. PK

      Yeah.

    8. SB

      ... because a lot of people encounter a problem, the, the issue you encountered trying to book that class, and they go, "Oh, fuck, the world is not n- not good enough." Or they think, they'll just think, "Oh, this is broken," and then they'll carry on with their lives.

    9. PK

      Oh, let me caveat that.

    10. SB

      Okay.

    11. PK

      So, I had come back from San Francisco-

    12. SB

      Yeah.

    13. PK

      ... 36 hours before that, and when I was in San Francisco, I had met a bunch of entrepreneurs.

    14. SB

      Okay.

    15. PK

      And this was my first time ever meeting entrepreneurs, right? So, going back to even the whole trying new things conversation, it was really important for me to take that trip to SF. I had been sort of stuck in New York City. I had been living this, the crazy dance life, the crazy, you know, nine-to-five life, and I had no time for anything else. So, I was not trying new things, and I needed an epiphany. I needed something to change, because the two roads I wa- I was on, like, they were gonna crash at some point-

    16. SB

      Mm-hmm.

    17. PK

      ... and it wasn't going to work. And I decide to go on this trip, I met- meet a bunch of entrepreneurs, and I come back thinking, "What if I could be an entrepreneur? Let me give myself two weeks to think of an idea." That's literally the mindset-

    18. SB

      Really?

    19. PK

      ... I was in when I encountered that. So, 36 hours later, I happened to be searching for this ballet class. And that's, it was just, like, during this perfect period in my life. And honestly, like, this is when I sometimes think, like, "Does the universe make us do these things, because what are the chances of all that happening-

    20. SB

      Mm-hmm.

    21. PK

      ... at the same time?" But it did. And I really remember in that moment thinking, "I know I'm the right person to build this because of this background I have, the communities I've been in, around, the c- experiences I have." There's probably no one else who cares as much about dance who then also went to MIT and Bain.

    22. SB

      MIT, which is an amazing college for those that don't know.

    23. PK

      Mm-hmm. Right? And it was sort of this perfect combination of things that made me say, "I gotta do this," and I went for it.

    24. SB

      But, um, that is extraordinary because a lot of people will encounter things. I'll encounter things today. I might sit on a chair and be like, "This chair could be better," but then I'll carry on with my day. You know what I mean? And then I'll open the fridge and go, "This fridge could be-"

    25. PK

      Yeah, that's true.

    26. SB

      ... you know? (laughs)

    27. PK

      I know that, yeah.

    28. SB

      But th- th- that's, that feels like the pivotal moment, which a lot of people w- listening to this, they'll, they'll notice things. Maybe they don't even notice them, because there's something in when you start looking f- You know, in your case, you were actually kind of looking for a-

    29. PK

      A problem to solve.

    30. SB

      Yeah.

  8. 40:1852:06

    What difficulties did you face starting your business?

    1. SB

      Let's go to the start, then, of this, the, the ClassPass journey, 'cause I'm really compelled by... You know, much of the reason I started this podcast was because I wanted to shine a light on the tough times in business. And I know when you're starting a business, especially a business in tech, um, it can be, uh, really, really difficult, 'cause you're-

    2. PK

      Mm-hmm.

    3. SB

      ... sort of jockeying and pivoting to find product-market fit and to figure out, like, what your customers want and-

    4. PK

      Hardest thing, yeah.

    5. SB

      ... how to deliver it. And I read that when I was reading about your journey, when, you know, you started, um, you quit your job in 2011, and then you go through a long phase of trying to figure out how to get people to use this thing, how to market it, and all that nightmare. T- talk to me about that nightmare.

    6. PK

      (sighs) So we went into the market with a very clear product idea, and it was a replica of what had ha- worked in another industry, so OpenTable which allows you to book restaurant reservations. It seemed like the right parallel to what we were doing, go on, search for classes. But what I didn't realize was that there was a very big missing part in it, and I'm, I mean, I'll spare everyone, like, the little details of it, but everyone has to eat, everyone does not have to work out, right?

    7. SB

      (laughs)

    8. PK

      It was... And working out usually is something scary for people-

    9. SB

      Mm-hmm.

    10. PK

      ... and it's more of an aspirational thing. It's not something that you have to do every single day. So they were sort of on different planes of people's psychology, which really became the biggest bottleneck to what ended up happening, because we spent a year, we spent half a million dollars building a product that didn't work. And, um, even though I had all this momentum, like I was saying, all these beautiful doors were opening for me, and they were, and I had a lot of great, you know, what I now call false signals of success, like followers, press-

    11. SB

      Oh, gosh.

    12. PK

      We ended up on the cover of Inc. Magazine without launching a product. And all these things made me feel like I was succeeding, right? Because this is what success looked like to everyone else. And then I launched my product, and no one went to class. It was li- it was... And no one bought a class. No one was transacting. It was crickets. It was just a really... It was, this was the hardest probably f- few months of the entire trajectory, because I, I had never really faced failure in my life. I mean, going back to everything I just told you, I had, I had sort of done things well. And I, and I tried to make sure that this would go well, right? By doing everything that I knew how to, how to, which was, let's get the press, let's build a beautiful product, let's, you know, get as many email addresses as possible. It, those were, like, the obvious things that seem-

    13. SB

      Mm-hmm.

    14. PK

      ... you know, you do when you're building a company. But I'd forgot to really ask myself if I was solving the problem I set out to. And I...... really think back to that moment, and even though it was the hardest, that moment is the reason I became a real entrepreneur. Like I don't think I was an entrepreneur before that day. I was excited about d- solving something, but the day I failed was the day I became an entrepreneur, because that was the day I really had to think deeper about creating something in the world that didn't exist. And I think it's so easy to follow the blueprints of everyone else and realize that entrepreneurship is actually about having no plan and having, you know, not following anyone else's ideas of what success is. It's about figuring out what, you know, what is it to solve your mission or your, you know, your business model that you're going after, and that woke me up. And it- it was a- a month or two period where we were trying to be comfortable, like it was this comfortable place we were in because we had raised money, we had just come out of Techstars, but, I mean, it was not going well, and I knew we were gonna run out of cash if, like, we didn't, you know, figure out something in the next few months. And, um, we just ... I remember like after a few- few weeks of it, we sent this email literally telling people to go to class for free, thinking, you know, "Okay, like, this is gonna work." Okay, we're- we're literally paying for the classes. People have to go, and still no one went, and that's when I realized we had just gone the wrong direction and I needed to, like, circle back up. I needed to break what we had built, just think a whole new way, reenergize my team around going ab- about solving this problem in a completely new way, not worrying about what we had done, but worrying about where we're going to go. And that flipped everything. And I have been there now so many times where I've been okay with throwing away our past. I mean, people don't know this, um, but ClassPass has changed its name three times. It wasn't called ClassPass. I mean, even w- this time I'm talking about, it was called something else, and I've thrown away names, like I've thrown away product ideas. Like we've throw- we've thrown away st- a lot of stuff. We've changed our pricing, our plans, and it's because it's not about that, right? It's about solving the problem in the world and moving towards that and your mission.

    15. SB

      So many entrepreneurs, though ... and this is probably the mistake I made when I was 18 and started my first little tech company, was, um, they get romantic about their initial hypothesis being correct.

    16. PK

      Exactly.

    17. SB

      So it's like you've got this square-shaped thing and you're just trying to force it into this triangle, because like your ego, and there's so much relying on it, and you know the one way, uh, you know you're running out of cash, and you just ... maybe that's why I just push harder. And then all these vanity metrics can be kind of confusing. "Oh, we've got lots of traffic-"

    18. PK

      False signals of success.

    19. SB

      "... though." (laughs)

    20. PK

      Yes, yeah.

    21. SB

      No one's buying anything, but we've got traffic.

    22. PK

      Absolutely.

    23. SB

      And, you know, as you just said, like, "I'm on a magazine." (laughs) But then certain entrepreneurs, I think, that have the humility to say, "In fact, it's not about being r- me- my hypothesis being right. It's about creating a product/market fit."

    24. PK

      Yeah.

    25. SB

      You know? And, uh, what was the moment when you started to get closer to that product/market fit?

    26. PK

      Yeah. And- and to ... You know, one of the things I love saying about that is to be, uh, mission obsessed, not product obsessed, and I learned that through that journey.

    27. SB

      Amen.

    28. PK

      But, um, you know, we started then putting this discovery pass out there. So what we did learn is that, you know, we started finally actually going and talking to a lot of the studio owners and talking to customers. I think the ... one of the things that happens in tech sometimes is you sit behind the tech.

    29. SB

      Mm-hmm.

    30. PK

      That you d-

  9. 52:0654:57

    Living in line with your values

    1. PK

      life."

    2. SB

      And how, in like a practical sense, in terms of a time allocation sense, did you get from that place to living more in line with those values of connection, community, love, and health?

    3. PK

      So I, you know, I, I'll, I'll, the details of like what-

    4. SB

      Yeah.

    5. PK

      ... I did on that session the first time I did it are in the book, but I will say this. So in the next six months, uh, after I started doing that, I literally met my husband a month later.

    6. SB

      Really?

    7. PK

      Yes.

    8. SB

      Wow.

    9. PK

      I decided to do a huge dance show at Alvin Ailey six months later, and I sold out 1,000, uh, 1,000 seats at that. So I got to do a huge performance. So-

    10. SB

      You're gonna sell so many books just by saying you found a husband.

    11. PK

      I know.

    12. SB

      Buy, buy something there. (laughs)

    13. PK

      It's like, it's really crazy. But I literally changed my perspective around love and what I wanted, and I met my husband a month later, which was crazy. And I also, you know, I set goals around what I wanted to do with ClassPass. I set goals around my health and how I wanted to live and work out on a daily basis. And I did all those things. And I remember, this is always my favorite moment, six months later, I was flying home on a plane. And when I first did this goal setting method, I had written it on a Post-It note 'cause I was on a plane. And I was on, I was on another plane ride 'cause I was always traveling. And I took it out, and I looked at it, and I had done everything on my dream list.

    14. SB

      Hmm.

    15. PK

      You know? And sometimes just writing down those dreams is the most important thing. But it was just such an important moment because I felt more, I don't, I don't want to say the word balanced because that has so many, you know, wrong intentions with it. But I felt that I was very clear about my priorities, and I went towards them. And I missed things too, but I didn't feel guilty about them. And I just felt so proud of myself for saying, "Here's what I want to do in my life, and I'm gonna go and do it," and accomplishing it, not just obviously professionally but personally as well.

    16. SB

      Mm-hmm. There's like an overarching theme here in your, in your journey, where the minute you become intentional about something-

    17. PK

      Yeah, things work out.

    18. SB

      ... as you described it, the doors open.

    19. PK

      It's true. It's so true.

    20. SB

      Do you, do you believe in that manifestation, or-

    21. PK

      100%. And it goes back to the, you saying, you know, we were talking about having a why. I think when you don't have a why, you go aimlessly, and you, you know, I think you start living life thinking that you want money, thinking you want to be famous, thinking you want power, and instead of thinking about, like, love and passion and purpose. And whenever I have made decisions that are about the former and not the latter, I've never been led in the right, in the right direction. And you know, if that's something people can take away from this, like, I think is one of, it's one of the most important points is if you go towards purpose, even if you are rebelling, right, and even if you might be pissing a few people off, I guarantee your life will be more fulfilling.

  10. 54:5759:05

    What were you like as a manager?

    1. PK

    2. SB

      What were you like as an entrepreneur, as a, as a leader and as a, a manager of people?

    3. PK

      I would say I was very much ... I had a lot of positive energy. I, I'm, I'm a small human, but I, I show up with all of me. Um, I...Um, I expect a lot of people, I think because people have always expected a lot from me. So, I'm sort of a, when- when you start working with me, I can very quickly tell if someone's going to, like, sink or swim, you know, because I don't tell you a lot, but I, like, let you go, because I think to me that's what I've had to do is just kind of ... I don't want to put a lot of boxes on you. I want you to just show me what you can be at your highest potential, and I think, like, that's sort of ... I liked giving people that room to be free and then allowing me to see what their capability is versus me saying, "You need to be your best in this box that I'm giving you."

    4. SB

      Mm-hmm.

    5. PK

      Uh, and I've- I've found really great talent in that way. Um, I've had to learn how to, like, hire for my strengths and weaknesses. You know, I think, um, that's probably the hardest- the hardest parts when your company grows is you do everything in the beginning, and then you have to learn to let go, and, um, I've definitely learned that building a tribe around you of great people is the only way to succeed.

    6. SB

      You struggled to delegate, right? In the early days?

    7. PK

      Um, I've gotten better at it. I've got- I've- I've realized that there is no other way to success and to build big things and great things in the world without being able to delegate, so I've become much better at it in my life, and it's the only way I- I can do what is my magical thing, right? And I've- I think I've put a lot of thought into that is, "What part of this company is- is something that only I know I can do," right?

    8. SB

      Mm-hmm.

    9. PK

      Everything else that I know someone else can do, I shouldn't be doing.

    10. SB

      Is that why you delegated the role of CEO to-

    11. PK

      Yes, absolutely.

    12. SB

      ... 2017?

    13. PK

      At some point, a CEO title becomes a lot of, you know, managing investors, managing team, doing press, and I was like, "This is not what I want to be doing with my time." I want to be solving the problem. I want to be in with my customers, working on, like, interesting concepts, not spending my day in a bunch of meetings that, you know, didn't feel inspiring. So, I think, like, you know, and everyone's set up differently. You have to know how you work. That's another big thing is- is learning the insights of what motivates you. Like, it's- it's the work you do and why you do it that ends up really mattering, right? In any job you're in. And I remember there was a point where I remember being so just disheartened and not wanting to show up to build my own company, and I'm like, "What is going on?" It was because I hated the work I was doing, and- and I loved, obviously, my company, but I hated the actual work that I had to do. And so I had to figure out a way to get past that.

    14. SB

      When was that?

    15. PK

      It was, like, 2000 and, like, 16, 17. I mean, we were launching, like, around the world. It was so intense. It was, you know, I mean, it was magical. Like I said, it was incredible to build that, but I remember, like I said, I was showing up every day dealing with, like, HR issues, legal issues, like, needing to talk to my investors. I wasn't, like, around my customers, and I wasn't going to class and around my product, you know? And that's what really fuels me as an entrepreneur and a founder.

    16. SB

      Did you have email dread? Like, I used to d- at one point, I remember when my company was getting big, because there was lots of chaos in my company, there was all kinds of cash flow issues, I used to, like, dread opening my emails. I was like, "Oh, it's gonna be some other bullshit from, like, an investor or some other thing, like a contract."

    17. PK

      Yeah, I mean, I- I definitely- I wanted to make sure that I had more to look forward to, and I'd- I think there came a point where I was looking forward to less and less, right?

    18. SB

      Mm-hmm.

    19. PK

      And I think it goes back to what I was saying about I didn't want my whole day to be like, "Ugh. Okay, there's, like, another competitor. Okay, we need to worry about this now." I didn't want my days to be about worrying. I wanted my days to be about dreaming, right? And by the way, you have to, obviously, as a leader of any of this, it comes with a responsibility, right? So, it's not that- it's not that I didn't have to worry about those things. There were certain parts of it that I knew I had to worry about and n- needed to be in my radar, but I knew there were certain things where I'm like, "I can hire someone to really work on this and fix this." (laughs)

    20. SB

      Mm-hmm.

    21. PK

      "It doesn't need to take up my time and energy," and that's really where- where the combination is, or where the decision lies.

  11. 59:051:03:07

    Why did you step away from ClassPass?

    1. PK

    2. SB

      So, all of that passion, all of that love driven by this really deep intrinsic why, why did you step away from ClassPass?

    3. PK

      You know, I think at some point, and this happens, I think, for so many founders, I mean, it had been a decade of my life solving this problem, which, of course, I'm so deeply passionate about. And, you know, I think the earliest days were when we did the most legwork in actually, like, figuring out the product, you know, the product nuances that were going to actually, like, unleash the behavior. I think it just got bigger, you know? For me, I think there are other things I want to do in the world, and there's probably other problems in the world I still need to go and solve, and it's on me to unleash myself to be able to face them, so I can move forward towards them and have them even come into my periphery. I think if you're kind of s- stuck in the past, you don't even welcome the doors, right?

    4. SB

      Mm-hmm.

    5. PK

      That are- are- that you need to go through to- to reach your future, and I know for me, my- my future is waiting for me, you know? And it's on me to sit there and walk through the door and go- go towards it.

    6. SB

      And was there- was there a feeling of, like, a loss of love?

    7. PK

      Yeah, I mean, it's a bittersweet moment, you know? It was, um ... it's super bittersweet, right? To- I- I always say this (laughs) like, the- the- the hardest day was when I stopped getting my- my ClassPass email. I mean, thi- like, it was insane.

    8. SB

      Yeah.

    9. PK

      I've had this email for- for years.

    10. SB

      Oh, shit.

    11. PK

      It was, like, my main inbox. And, um, you know, it was- it was definitely a sense of loss. I mean, I think it's, you know, uh, eh, for ... it's like having a child and watching your child get married, right?

    12. SB

      Yeah. (laughs)

    13. PK

      But it's also being able to say, like, "They're okay." I- I did all I could to get them to this point and being proud of that, and that's really where I'm at.

    14. SB

      I remember the- when I resigned from my company, it went public, and I said to the company, I said, "I'm gonna resign, but I have one caveat." They were like, "What is it?" I was like, "I want to keep my email." (laughs)

    15. PK

      Oh, you didn't use either?

    16. SB

      I still got my email. (laughs) I still have my email.

    17. PK

      I, you know, and it- it's funny (laughs) you say that. I think I didn't, going back to the whole ... uh, it would just been more noise, right?

    18. SB

      Yeah.

    19. PK

      For me?

    20. SB

      True. You're right, yeah.

    21. PK

      You know? And so-

    22. SB

      I don't check it. (laughs)

    23. PK

      Yeah. No, I figured you, yeah, you probably don't.

    24. SB

      (laughs)

    25. PK

      Could you imagine if you did?

    26. SB

      Yeah.

    27. PK

      (laughs) I just think it was- it was a nice break for me. I actually remember creating a new email address, and it was like, "No mail."

    28. SB

      Yeah. (laughs)

    29. PK

      And I'm like, "What?" You know?It's interesting because it started making me realize, like, what do I want to fill that part of my life up with? You know?

    30. SB

      What's the answer?

  12. 1:03:071:06:53

    Work and family balance

    1. PK

      of it.

    2. SB

      And that wave of press whenever- whenever someone becomes a unicorn is tremendous, right?

    3. PK

      Yeah.

    4. SB

      And that will reach so, so many young women all over the world, and entrepreneurs. Your partner, your- your son, completely other part of your life. Nick-

    5. PK

      Yeah.

    6. SB

      ... and Zayn?

    7. PK

      Yep. Nick and Zayn.

    8. SB

      How's that been? You know? You talk about the obsession you've had building ClassPass. Um, entrepreneurs always struggle and tend to struggle in managing their romantic relationships in the other part of their life. What advice have you got for me on maintaining a good romantic relationship and family whilst also striving to big- build big dreams?

    9. PK

      Yeah, and I- I'll be honest. I think we're all always still learning in the process of it. But I think one of the biggest things I learned is, and this goes along with s- a lot of the advice I had with my parents, is bring them along on the journey. Nick was with me through so much of it. I mean, when we went to go launch London, um... I- I always actually love this story, is me, one of, uh, my co-founder, and m- one of my, uh, sales- sales girls came- came with me, and so did Nick. And we got to go try out about 30 studios in- in London in about five days, and Nick just went and did some of them too. Like, it was amazing. We all just went and worked out, and he was sort of, like, checking out studios because we, before we put anything on the platform, we wanted to make sure they were vetted studios. And this was, like I said, it was, like, six, seven years ago, so there wasn't that much, that many reviews on studios.

    10. SB

      Mm-hmm.

    11. PK

      And, um, yeah. Like, I mean, he would come to Australia with me, come to London with me, and he was just a big part of the process, you know? And I think that's so awesome that we got to live... Like, he got to live the dream with me, and I think that was a really nice part of it. I think, as we've had a kid, we've just had to become very clear on priorities, right? And he is an inc-... He's a partner at a law firm. He's e-... You know, one of the youngest partners at his law firm. It's insane what he's been able to accomplish in his career. So we have to just always be very, very communicative on what we both want, right? In setting goals, and, "Hey, like, what do we want to accomplish this year in terms of our lives?" Right? The same way I think about it personally, we have to think about it in terms of what our family wants to do. Whether it's, like, school, whether it's traveling, right? What do we want to make sure we both do as a family unit combined with, you know, our jobs and our ambition, you know? And I think it's so important, especially for women, to surround themselves with partners and people who will constantly help them stay ambitious in their life, because it's one of the hardest things.

    12. SB

      What if there's conflict between when you think about what the family wants to do and what Payal wants to do a- as... in terms of your ambitions, and then his ambitions with his career?

    13. PK

      You have to talk it out and come up with a plan. You know? I... To me, a plan is the most important thing. And sometimes there is conflict, but you have to try new things. Similar to pivoting, right, and iterating, like, on a company. You sometime... Both people have to be flexible to be like, "Okay. Well, like, if this current situation isn't working, we're gonna try something new." Right? "Okay. Like, you want this. I want this. What if we try a combination of this for six months? What if we..." You just have to be flexible and adaptable. I think the biggest mistake is not doing anything-

    14. SB

      Mm-hmm.

    15. PK

      ... and staying sort of stagnant in a place where someone's uncomfortable or someone's not happy-

    16. SB

      Mm-hmm.

    17. PK

      ... and not helping the other person, right? At the end of the day, Nick being happy in his life is gonna make him the best husband to me and the best dad, and me being happy in my life is gonna make me the best mom and best wife to him, right? And we both know that. So it's about saying, "What does happiness look like to both... to- to us individually, but then us together as a family?"

    18. SB

      Your journey has weaved an up, down, left, right, all of it. It's been a tremendous rollercoaster with so many highs and lows, and everything in between. You spoke earlier about the importance mentorship has played in your life. Have you ever been to therapy?

  13. 1:06:531:09:00

    Therapy sessions

    1. SB

      Has that-

    2. PK

      Have I ever been to therapy? Um, I did a little bit of therapy actually at the beginning of last year. Um, you know, it was... I had a baby, by the way, six weeks before the pandemic, and then, like, my company came to a- a halt. It was just a really crazy time, so I had just gone to therapy to just start talking to somebody because I didn't even know how to make sense of so much of where my mental state was at that point. I hadn't seen people. I'd literally been a mom for a year living at home, right?

    3. SB

      Mm-hmm.

    4. PK

      It was just an... My life was so different than it... what it looked like... pre-pandemic at that point. And so I, yeah, I have, and I, I mean, I recommend it to anyone. It's- it's sort of like a fitness instructor-

    5. SB

      Hmm.

    6. PK

      ... who works on your body. You need to work on your mind sometimes and see, you know, what your roadblocks are, right? We know them, like, "Oh my God, I feel, I don't feel strong with my left arm." Like how do you get that stronger?

    7. SB

      Hmm.

    8. PK

      We sometimes have blocks like that too.

    9. SB

      And it sometimes, uh, for me, it's been like sometimes there'll be a feeling which I can't ... which, where you just know you're out of orientation or something's not right. And I think the pandemic did that to a lot of us, which was-

    10. PK

      Yeah.

    11. SB

      ... destabilized our, us in many, many ways. Um, your journey is- is phenomenal. It's really, really phenomenal, and you're a really phenomenal person for so many reasons.

    12. PK

      Thank you. Appreciate it.

    13. SB

      One of the reasons why is just, you're just this, from like the minute you walked into this room, you're just this, like-

    14. PK

      (laughs)

    15. SB

      ... ray of sunshine.

    16. PK

      Oh, thank you.

    17. SB

      And that's why I think I asked the question about, like, therapy and your hard moments in particular because you have, you have just a- an unbelievable smile and you have such an, it, f- uh, you, I'm like, "Is this person always this-"

    18. PK

      This... (laughs)

    19. SB

      "... this (laughs) media?"

    20. PK

      It, you know, but it goes down to I've always believed there's the light, right? Like, I think it's the question you- st- we started with. It was, I just believe there's, like, goodness to give and service and- and purpose. And when I'm not aligned with my purpose, I do feel sad, right? Those were my, like, hardest moments where, you know, if I didn't care about sharing, you know-

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