How This Former Fitbit Exec Launched An App That Is Revolutionizing Digital Fitness

Learn more about the journey of this CEO and mom from employee to entrepreneur.

How This Former Fitbit Exec Went from Employee to Entrepreneur

Wouldn’t it be great to have access to the same celebrity trainers that are responsible for the incredible abs of actresses Jessica Alba or Jenna Dewan? Well, now you can, thanks to FitOn, the digital fitness app that is on a mission to democratize wellness by bringing world-class trainers directly into your living room. While working as a busy vice president at Fitbit, FitOn Founder and CEO Lindsay Cook had an epiphany:

As a busy working mom, I realized that making it to my favorite studio classes had become seemingly impossible. When I searched online for more accessible and practical workouts, I was disappointed in the quality and lack of motivation that existed. Hence the inspiration behind FitOn. Now, no matter what challenges life throws your way, our world-class trainers, rich content and engaging social tools will help you reach your fitness goals—all in the palm of your hand, literally.”

I took time out with Cook to discuss what makes FitOn so unique, how she was able to raise more than $4.6M in equity financing and what advice she has for other women looking to take the leap from employee to entrepreneur.

Caroline Castrillon: What about your experience and learning at Fitbit has helped you build FitOn?

Lindsay Cook: At Fitbit, I got super immersed in the health and fitness category—learning about the users and trying to understand people’s dynamics around health and fitness. What it taught me was that working out actually isn’t that easy. There’s work in working out! Simple things Fitbit did with their community and the leaderboard gave people that extra motivation to be a little bit more active. That’s really what we’ve been trying to do with FitOn—figuring out how to take premium workouts that people can do with their friends and even on their own, but add some social motivation to it as well because your social community is a great incentive for you to be active. Working at Fitbit also helped me realize that a lot of the fitness apps in the industry didn’t have real-time motivation and guidance. That’s what the concept of FitOn is all about—how to combine real-time guidance with amazing celebrity trainers and the experience of group fitness classes that you can do when you are time constrained and can’t always make it to the gym.

Castrillon: What makes FitOn different from the other fitness apps out there?

Cook: We have four big differentiators. One is that we make very high-quality workout videos where you can exercise at home but still get the feel of premium studio fitness classes. We also offer an extensive variety of workouts—everything from cardio to HIIT to strength to yoga. There’s something for everyone. Our classes are led by world-class celebrity trainers like Katie DunlopCassey HoJeanette Jenkins and Jennifer “JJ Dancer” Johnson. Another big differentiator is our social component. We give you the ability to work out with your friends on the app. You can invite them to classes and schedule workouts with them so you can cheer each other on. The biggest differentiator is the affordability. Riding a Peloton bike is an amazing experience, but it costs over $2,000, and not everyone can afford that. So, what we really wanted to do was to democratize the fitness experience and make it so that any woman, no matter what real estate or work out equipment they have, could afford some fantastic workouts that they could do anytime, anywhere.

Castrillon:  It has been widely reported that it can be more challenging for female founders to secure equity financing compared to their male counterparts. You recently raised more than $4.6 million in equity financing. What was that experience like and how did you approach the process?

Cook: For me, the process of raising financing was such a game of persistence. You have to be unbelievably aggressive about trying to get meetings with the right people. I decided to play up my experience as a woman and honestly just knowing the audience of the product that I was building was so much to my advantage. There are a lot of VC’s out there nowadays that are trying to balance their portfolio with more female founders, and they are under the scrutiny of trying to do that. I tried to always use my gender as an asset. At Fitbit, I was one of the first women on the executive team. When we were building products, I was the female voice in the room when the majority of our customers were women. As I was fundraising, it was just a matter of showcasing how much I knew about my audience and how much conviction I had that I could successfully build a product that they wanted.

Castrillon: For other women interested in securing financing for their new businesses, what do you suggest they do to prepare their pitch to potential investors?

Cook: The best advice I ever got was that it’s all about extreme confidence. You literally need to walk into the room and be the most confident version of yourself because the main challenge is that the person that’s coming in after you is going to do the same thing. So, if you’re not absolutely confident in yourself and in what you’re building, they are going to get the check instead of you. You just have to bring that passion and conviction to those meetings because in many ways the VC’s are investing more in people than they are in the specific concept. They clearly have to like the space, but they also really want to believe that you’re the person that’s going to be able to do it. I also practiced a lot and shared my pitch deck with anyone who could challenge me about it to make it better. By the time I had one of the first real pitch meetings with someone very important, I had played it out so many times and practiced it in so many different ways, that I felt very confident doing it.

Castrillon: What advice would you give women out there who may be afraid to take the leap from employee to entrepreneur?

Cook: Honestly, just try to test out your ideas before you go full steam. When I started this company, I began testing out ideas in a scrappy way with other women. I would do focus groups. I would try to get people in a room and ask them questions about what I was building and what their needs were in the health and fitness space—basically, any questions I could think of that would help lead us in the right direction to build a great product. When you start testing things, getting the product in front of other people and trying to determine if you have something that people find unbelievably delightful or compelling, that momentum will help you fully identify if you want to make that leap.

Castrillon: What is your vision for FitOn five years from now? How do you see the company evolving?

Cook: The question we ask ourselves is how we create a significant health and fitness brand that is about helping women get more active and helping them make it fit, which is our motto. We want to create a fitness company for the modern woman—helping that modern women fit fitness in and get all the benefits of health and fitness including feeling good and looking good. For us, it’s so much more about the self-care aspect. So, we just want to keep building on what we’re doing. We want to be that place you come to get really excellent high-end workouts that you can do with your friends. The digital fitness industry is growing immensely right now, and there is a lot of potential for companies in it. We ultimately want to be one of the top players that people turn to for a great solution to incorporate fitness into their busy lifestyle.

The conversation has been edited and condensed for clarity.

To learn more and see if you’re ready to make the transition to be your own boss, check out my free resource:
5 Signs It’s Time to Leave Your Soul-Sucking Job!

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