Boss Lady Spotlight: Lindsay Bailey 👸🎤
Updated: Aug 3
Lindsay Bailey on building a company with a mission to prioritize
personal wellness in the workplace
Self-made entrepreneur, Lindsay Bailey believes that dedicating time to personal wellness is a non-negotiable. This belief fueled the creation of her company FitPros, a wellness provider bringing top-notch wellness events directly to organizations to improve employee health and happiness. As founder and CEO of this young, yet rapidly growing company, Lindsay’s success lies in her scrappy nature, quality relationship building, and a personal ethos to do good in the world. “What drives me today is knowing there’s a need and knowing that we can help people,” Lindsay says.
Despite coming from a successful business-owning mother, growing up Lindsay did not envision herself running her own company. While respecting her single-mother’s work, she chose the corporate path after graduating college, finding success in marketing and planning events for one of the major dining and entertainment providers for yachts and cruises. Lindsay then transitioned to an advertising agency working with big name brands that had her traveling all over the country. By her mid-twenties, she felt proud of her career, working hard and generating the income to show for it.
Underneath her lucrative corporate career, Lindsay struggled to find a healthy work-life balance. She was not prioritizing her health, spending her rare free time indulging in partying to let off steam. “I had a pretty amazing career, but I was partying too much. I was about thirty pounds heavier than I am today and was not healthy mentally or physically,” she explains. “I had no idea where to look for help and my manager was not encouraging. She was a slave driver and didn’t encourage me to leave my desk. It was a really negative space I was in.”
At her breaking point, Lindsay knew she had to make a change to her unsustainable working lifestyle. Although, walking away from her successful corporate career was not an easy decision. “I think the reason why I paused for so long, even though I knew I should have made a change, was just because of the fear of the unknown. I didn't know if I would have money. I didn't know if anyone would support me or my decision. I didn't know where I would land.”
"I didn't know if I would have money. I didn't know if anyone would support me or my decision. I didn't know where I would land.”
Further spiraling, Lindsay’s boyfriend (now fiancé) presented her with an ultimatum: she had to either take responsibility for her unhealthy lifestyle or he was out. “He helped me look in the mirror and realize how unhappy and unhealthy I was, and just how much I was drinking,” she says. “I fell to my knees and I had these visions of my whole world and future blowing up.” She ultimately resolved to quit drinking and is now five and a half years sober.
Despite her fears, Lindsay bravely left the corporate world behind. Armed with a newly profound sense of prioritizing her well-being above all else, she chose a radically different career path both in industry and in financial stability. She became a personal trainer, barely earning minimum wage. “I truly wanted to learn at that point in my life. I was really just trying to follow my heart and find happiness, so I put my personal needs before finances. I was just really driven by that,” she says.
Furthering her path to physical and mental nourishment, Lindsay journeyed to India to earn her yoga teacher training certification. Seeing how people lived in India altered her money mindset and soothed her financial anxiety. “Meeting people who certainly didn’t have what we have in America, but who were still satisfied and peaceful was so beautiful to me,” she explains. “So, I was like, ‘you know what? Whatever journey the Universe takes me on, that’s what it is supposed to be. Even if I don't have money, I'll figure out a way to make it work.’” After all, Lindsay did not come from means and was raised by a single, hard-working mother, so she knew how to make do without a whole lot. She learned how to be scrappy from her mother, which is a skill that has contributed to success throughout her life.
Returning from India refreshed and determined, Lindsay began to carve out the life she truly wanted to live. Through hard work and masterfully building relationships, she started an online coaching school where she could set her own rates to financially support herself. Her personal training experience and yoga teacher certification lent her the ability to bring in clients and make connections quickly. “I was able to start building a reputation for myself, building a name for myself, and making connections, more than anything,” she says. This was her first entry point into entrepreneurship, motivated by a desire to use her knowledge of wellness to help others. At the same time, Lindsay pushed herself physically to a whole new level. She slimmed down to ten percent body fat and successfully competed in a fitness competition. The competition proved valuable in expanding her network as well as her knowledge about physical fitness and health.
"I was able to start building a reputation for myself, building a name for myself, and making connections, more than anything.”
With her life moving in a such a positive direction, just five days after her fitness competition, tragedy struck when her youngest brother passed away. Lindsay broke down and once again questioned the path she was taking. Craving some soul-searching, she took a few months to backpack through Asia to look for answers. “I was seeking peace with my life's journey and where the Universe was supposed to take me,” she explains.
Yet again, Lindsay’s instinct to take time away for introspection paid off. Rejuvenated from her Asia trip, an idea suddenly clicked. She thought about all the people who spend their work days sitting behind a desk, recalling the feelings of stress and unhappiness. She wondered, “what could have helped me back then and what do I know now about fitness, health and wellness that can improve the lives of those working office jobs?” She concluded there was an absolute need for wellness in the workplace, and thus the idea behind FitPros was born.
Lindsay’s first step was enlisting a graphic designer friend to create a website for the company she envisioned. Lindsay knew she would have to single-handedly bootstrap her business, and so leveraging her existing relationships as well as networking with others was critical to getting it off the ground. “Even today, every client that we have, every company that we work with, is through relationships,” she says. There’s no question that Lindsay’s artful relationship building has led to business success. Since launching in 2016, FitPros has seen tremendous growth. “Year-over-year we’ve pretty much doubled in both revenue and in clients,” she says. “This year we’re not quite projected to double because we’re really focused on streamlining operations and services but we’re still expected to do very well.”
"Year-over-year we’ve pretty much doubled in both revenue and in clients.”
Lindsay has big plans on the horizon to scale her business. “There are so many different things that we’re talking about internally, like potentially selling product through our website with a partner, and really building out strategic partnerships and alliances as well as further leveraging technology,” she says. “There is a lot of opportunity to expand into new industries and partner with different types of companies such as apartment communities, building properties, hotels, hospitals, and other institutions that could use the services we provide.” Furthermore, she is already developing a whole new branch for her company that will be a children’s camp.
Other than skillful relationship building, Lindsay believes there are a few key elements that have contributed to FitPros’ success. She emphasizes the importance of forming vital alliances and strategic partnerships with companies that align well with FitPros’ services. In addition, she believes in following her intuition and keeping the mentality that her company is on the right path, contributing to the greater good. Hiring people that fit well within the company culture is crucial for Lindsay. “My biggest learning to-date is just really making sure that the people we hire align with our beliefs,” she says. “It’s important to take a deep look as I’m interviewing people to make sure that’s there.” For Lindsay, fitting into the company culture means being driven by a sense of doing good in the world. “My motto in life is do good and be good and receive good. I don’t think it needs to be any more complicated than that,” she says. “Our mission is to follow the intention of making sure our programs are reaching for the entire population and that we are doing our best to provide services for all types of people.”
"Our mission is to follow the intention of making sure our programs are reaching for the entire population...”
As a perfectionist, relinquishing control and trusting others to help her has been a learning curve for Lindsay. “Working with a life coach has helped me work through admitting that I need a break and I need help,” she explains. “Letting go, I think goes back to trust. I know the team that we’re building believes in the right things. Trusting they will follow their hearts and make the right choices is key and it feels good to trust them.”
Running her own company has taught Lindsay about money management for both her business and for herself. She always made an effort with her personal finances by keeping her spending low and researching the best financial service providers for her situation. However, once her business started taking off, she decided to further her education through attending the Tony Robbins Business Mastery Conference. From there, she realized that hiring a fiduciary financial advisor would be in the best interest of her company. Along with being advised on her finances, Lindsay stresses the importance of having a bookkeeper that can really stay on top of where company spend is coming and going. In terms of funding the company, Lindsay’s signature scrappy nature and selflessness has played an integral role. “I didn't pay myself for the first year and a half,” she says. “And even today, I pay myself less than I do most of my team members. But we’re still a young and growing company, and that's just the way it is, and I'm good with that.”
In addition to running her own company, Lindsay serves as co-president of the San Francisco Bay Area chapter for Ellevate. Ellevate is a community of driven professional women who are helping each other take the next step in their careers. The community offers support groups, networking events and workshops featuring world class speakers and provides resources to help members achieve their professional goals. Lindsay volunteers as a co-lead to a group of about ten women that run the chapter. “We each have different duties – one handles the marketing, one handles the finance, etc., and we meet up once a month to discuss events and strategies with the goal of inspiring women,” she says. “Our goal is to deliver events that create a network for people, while providing valuable learning experiences.” Lindsay is fueled by helping women achieve their goals but also sees value in the organization for her own personal enrichment. “Truly for me, I needed an opportunity to be around other smart women that are driven and are wanting to create things or to just continue learning,” she says.
"...I needed an opportunity to be around other smart women that are driven and are wanting to create things or to just continue learning.”
With everything she has going on in her life, one might wonder how she possibly has time to take care of herself. However, Lindsay believes in the importance of carving out personal time in order to reset her mind and body. “In terms of self-care, I would say first and foremost, for me physical exercise is just like a mind release. It's really not even to look good anymore. It's because I need to sweat and so that I can think,” she explains. Additionally, she writes a gratitude list most mornings. “I write down the things I’m grateful for and a few mornings a week, I’ll take five minutes and I’ll meditate and sit and think and process.” Clearing her mind a few minutes each day is essential for Lindsay as turning off from her business is not always easy. Although, she doesn’t necessarily see that as a negative. “Honestly, it never turns off. Never ever. But I'm okay with that because I love what I do. I mean, I get so excited and so fired up setting up new programs and things.”
As Lindsay reflects on the path that led her to current success, she is proud of the decisions that got her here. If there was anything she could tell her younger self fifteen years ago, it would be to relax and let life flow. “I was just always on pins and needles. Even though I still have that perfectionist in me today, it’s so much different than it was back then,” she says. “Because now I believe that if I force something, then it won’t work out the way it’s supposed to and it'll crumble anyway. I really look at something like if it doesn't feel right, if it's not working out, then just let it go and let whatever is supposed to happen flow in.”
Lindsay's Recommended Reading List 📚
- Finance: Unshakeable by Tony Robbins
- Early Career Inspiration: 4 Hour Work Week by Tim Ferriss
- Spiritual: Intuitive Living by Alan Seale
- Workplace Wellness Bible: Workplace Wellness that Works by Laura Putnam
- Leadership: Multipliers by Liz Wiseman
📣 Checkout FitPros to find out how they're empowering people to take charge of their personal health where they spend the most time...AT WORK 🙌