ClassPass Founder Payal Kadakia wants more women to ignore societal timelines when it comes to personal and professional success. "Everyone always asks me, 'How was it being a woman in tech?'" she says. "And, I think one of the hardest things for me was the pressure to get married. I know that's such an odd topic, but literally, I felt like that was probably the hardest part… It was this outside pressure that I had to fulfill some role that society wanted me to, and at the same time build a huge company, you know?"

As she released her book, LifePass: Drop Your Limits, Rise to Your Potential, Kadakia sat down with Chief Member Shachar Orren, Co-Founder and CMO of EX.CO, to talk about her decade-long journey of building ClassPass, its acquisition, and why it is her hope for all women to be unapologetically ambitious when it comes to their careers.

On pivoting during the pandemic

"I think for every company it makes you really look inward for a second and say, 'Wow, what are we going to do? How are we going to move?' I think the DNA of ClassPass has always been one that was about iterating fast and pivoting. We literally transformed the entire homepage of the app into a video platform one week after the pandemic hit and all of our studios shut down. And so I think it really became about just moving quickly, which was something that was already in our blood."

On when she knew it was time to move on

"I think for me personally, the biggest thing was figuring out when we started being like, 'Okay, Payal what are you going to do in this new entity?' And me thinking about that and realising for me as an entrepreneur that it was time to move on. Like, that was probably personally the hardest thing after 10 years of doing something and building something to kind of know that, 'Hey, this is the time I have to really say goodbye and start going and doing other things in my life.' I think in all of our careers, we don't know how to do that. I mean there were points where I quit my job and there were points where I changed jobs, but I think it's obviously harder when it's my company. But, I knew for my career, this was the right thing to do at the moment and I had to take the leap."

On selling ClassPass

"Mindbody and ClassPass have worked together from the earliest days. When I started the business and I didn't want to build the search engine for classes, I needed to find a way to get all the data. And luckily enough, you know, the Mindbody system had all the classes and was working with so many of the providers we worked with.

"So we literally met them in 2012. I met the Founder and CEO [and] I was literally a five-person team in the middle of Techstars, which is an incubator in New York City at the time. And we went to dinner with them. We had no idea what was going to happen from the relationship. And, I love to talk about this because sometimes you just never know. This dinner obviously was just us meeting and we stayed in touch as ClassPass was pivoting and growing.

"I think we always knew that it was a matter of when, not if, we would come together because both of our businesses had just such synergistic value with obviously, you know, the reservation platform they had built, and then the consumer brand we had built. And I think when the pandemic hit, the conversation sort of got a bit more accelerated because we knew that we needed to come together because we needed to help the industry."

On ignoring societal pressure

"Everyone always asks me, 'How was it being a woman in tech?' I think one of the hardest things for me was the pressure to get married. I know that's like such an odd topic. But literally, I felt like that was probably the hardest part. It wasn't always like just being a woman in the room. It was this outside pressure that I had to fulfil some role that society wanted me to, and at the same time build a huge company, you know? And I knew my company was succeeding. Like the second it started working, I had emails from investors being like, 'I think you may have built the next Uber.' I knew I had built something that was going to be huge. And here I was, with people being like, 'So are you going on a date?' And, you know, feeling sad inside for not having a guy or something like that. I think that was like a really interesting part of my life.

"I was like, 'You know, I have responsibilities to my investors [and] my board. Of course, I want to get married and have kids and all of that, but I have responsibilities and something I'm really doing well at.' So you know, I think surrounding yourself with people who are going to allow you to be you and do things on your own timeline is really important, right?"

On embracing ambition

"I'm going to always be ambitious and that's never going to stop in my life. And, you know, I think we need to really recognise that women can be ambitious and they will find their own way of doing that. Whether it's marriage, kids, all of that, we need to help them continue to feel competent in being ambitious and not feeling like they need to change in any way or that they're doing something wrong. It's not about having it all, but [women] can go after, you know, being that ambitious woman and not having to sacrifice anything else at the same time."

On women entrepreneurs' biggest challenge today

"I think today we're seeing a lot of women go for it. It's been really amazing to see, at the seed level especially, so many women going through it. I think what I really want to continue to help the conversation with is the later stages. It's like when you get to the B, the C, and the D [rounds], and those rooms don't have enough women around them. So I think it's really about helping women get through those cycles because in the beginning when you're starting a company, everyone's like, 'Oh, this is fun.' When it gets more serious, that's really when, for me, the pressure really sets in on both sides."

On her legacy

"I've always said everything I create in the world, I want it to be timeless, which means I want it to outlast me. You know, I think, we don't think about that as much in the work we do. I feel like we live in a much more shorter cycle world, whether that's just content and media and all of that. [But] whether it's the art I do or the products I make, I think it's about creating timeless things."