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How To Recover From A Career Setback, According To The Founder Of ClassPass

When you found a company, you’re inherently agreeing to make many, many mistakes on the path to success. No company launches to pure perfection—no matter what their Insta narrative shows you. The founders of some of the most progressive, profitable, and prolific businesses all have one thing in common: They’ve royally f-ed up, at leastonce (if not dozens of times), before hitting their stride. Failure is essentially in the fine print of becoming a powerful, game-changing person.

As you see it today, ClassPass is an example of a super successful company. It was valued at $470 million in 2017, and has joined forces with over 22,000 health clubs across 18 countries. We recently welcomed the founder, Payal Kadakia, on Girlboss.com as the host of one of our Digital Firesides, where she answered all of your questions about big business. Amongst the paragraphs worth of great advice, she shared that there were TWO previous versions of ClassPass that were built out before the product finally reached the quality she was looking for. It wasn’t a seamless process by any means—it took a few setbacks before things really came together.

Read on to find out how Payal managed some of these mishaps, as well as other nuggets of wisdom she had to share during her Digital Fireside.

1. How did you find the ~right~ mentor?

“Find people who have something to teach you. Try to get introduced through a common contact so that you’re not reaching out to them cold. Then, when asking for their advice, make sure they get something out of the relationship, too. Relationships that are one-way won’t survive. My mentor Anjula Acharia has been an incredible help to me throughout ClassPass’ journey and I found a lot of great mentors through past jobs as well. I’ve also sought out people who I wanted to know, like Cyrus Massoumi, founder of ZocDoc. Early on, I went to events and met people and was genuinely open about the help I needed. Girlboss is a great community to start!”

2. Did jumping into creating a new business scare you? How did you grow to conquer fears, challenges, and setbacks?

“Creating a new company is scary, of course, but you can conquer your fears by acquiring the right foundational skills and tools. Also knowing that you’re doing something that really inspires you is helpful. Creating a new company is high-risk, and there are so many ups and downs. You have to know your ‘why.’ For me, I was passionate about my mission and my passion for my mission was greater than my fear of any setbacks, so I knew it made sense to take the entrepreneurial plunge. As a founder, my confidence has grown as I’ve seen that setbacks are just an opportunity to learn.”

3. The biggest lesson you learned from your early days of seeking capital?

“I learned it’s important to be authentic. In the beginning, I hid that I was a dancer because I didn’t want investors to think that I was distracted. The thing is that being a dancer is part of what makes me, well, me, and it’s also what enabled me to come up with the idea for ClassPass. Some investors won’t ‘get’ you and you’ll always get more no’s at the beginning, but if your mission is compelling and your product is serving a real market need, you’ll eventually get the funding you seek.”

4. Did you have any setbacks when you first started ClassPass?

“We actually launched two earlier versions of ClassPass, and though they were fine, they didn’t fundamentally achieve my goal of getting large numbers of people to class. I had to be willing to abandon a lot of hard work, and I had to have faith in the power of my mission. It’s painful to keep iterating your product, but that’s what it took for us to finally get it right. I’m actually grateful that we had these experiences because they built iteration into the DNA of our company. That value has been critical to keeping us highly innovative and customer-focused as we’ve expanded our product offering, as well as our global footprint. I tried to reframe each setback as a learning opportunity. In the beginning, it was harder to move forward after setbacks, but over time it became much more natural to use those setbacks as data points to help us move forward.”

5. Do you ever feel lost in your career? If so, how do you get through it?

“I think it’s important that you let yourself evolve in your career and never feel like you are defined by a position or a specific job. It’s up to you to continue to evaluate whether you’re still learning, growing, and enjoying what you do. After college, I worked in great traditional jobs. Other people told me that I was doing exactly what I should have been doing professionally. However, I knew that continuing on that path wasn’t right for me. I asked myself the hard questions and decided to change course and shift from the safety of my established career path to the riskier (but more exciting) entrepreneurial path which was ultimately right for me.”

6.In the early stages of ClassPass, how did you convince gyms to partner with you? How were you able to get them to buy in?

“We can only be successful when our partners are successful. We spent a lot of time listening to them, learning what made them unique, and figuring out how we can work with them to help them achieve their goals. There’s nothing as important to success as customer empathy. We’ve invested heavily in building up trust among our valued studio partners, which is why we have 22,000 partners globally today—and counting!”

7. Advice for making a major career change?

“It’s never too late to recreate yourself! I recommend speaking to people who have interesting jobs and seeing if there’s a way you can do some small unpaid or part-time consulting projects for them to see if their fields might be a good fit for you and to see if your skills might be transferable. Sometimes you have to take a couple of steps back in order to move a mile forward, but it’s worthwhile if it makes you happier and helps you feel more satisfied in your career.”

Join in on the conversation and be sure not to miss our next Digital Fireside by signing up for the Girlboss professional network today.


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