In this powerful episode of Leadership + with Dr. G, we dive into the inspiring journey of Winsome Brown, CEO and Co-Founder of Lean on Dee Senior Home Care Services. Winsome shares how she walked away from a 20-year career as a corporate accountant, burned out and overwhelmed, to pursue something entirely new—building a senior care business rooted in love, service, and strategy.
After years of navigating the uncertainty and high demands of corporate life, Winsome made a bold decision: she accepted a buyout and took a leap of faith. With no healthcare background but a heart for people and a sister in the healthcare industry, they were inspired by their own personal journey of caring for their mother and grandmother to launch this business in 2019. A life path reading affirmed what she already felt in her spirit—she was a natural nurturer.
Winsome’s accounting background didn’t go to waste. In fact, she credits it with helping her manage the financial side of her business effectively. Her advice? Know your numbers. Passion is powerful, but a strong business foundation is essential.
Launching Lean on Dee was no overnight success. In the early days, Winsome wore every hat: CEO, CFO, scheduler, caregiver recruiter, and operations lead. It was exhausting. She hustled to build trust and visibility—offering free dementia education sessions, becoming a community educator with the Alzheimer’s Association, and even handing out gift baskets at churches. All of this while making no money her first year, ending up $26,000 in the red.
But she kept going.
Her husband reminded her that starting a business is like launching a plane—it takes massive effort at the beginning. That metaphor stuck, and so did her commitment to seeing the dream through.
“Everyone wants to leave their 9-to-5 to be their own boss,” Winsome says, “but no one tells you that being your own boss can mean working 24/7.” She’s candid about the struggle. The sleepless nights. The doubts. The emotional toll. But she’s also honest about the reward: financial freedom, flexibility, and the joy of building something meaningful.
Coming from humble beginnings in Jamaica, Winsome is now able to provide for her family in ways she once only dreamed of. But she’s quick to say none of this happened by chance. It was built with intention, sacrifice, and systems. One of the key tips she shared was that of knowing your customer. This she actualized when she realized that the true customer wasn’t the elderly client she sought to care for, but instead, it was their adult children making care decisions.
Winsome highlights what many entrepreneurs overlook: the back-end of the business matters just as much as the front-facing work. From strong contracts and scheduling systems to polished customer service and collecting client reviews, every detail adds up.
One of her key lessons? You can’t do it all. Build a team. Get support. Whether it’s hiring a part-time scheduler, bringing on a consultant, or using a fractional executive for strategy—help is not optional, it’s essential.
Especially for nonprofits and small businesses navigating layoffs, funding cuts, or economic downturns, Ms. Brown’s story reminds us that, you don’t need to be a Fortune 500 company to operate like one. You just need the right systems and the right people.
The journey hasn’t been easy, but it’s been worth it. Winsome’s story is a masterclass in perseverance, leadership, and turning personal pain into powerful purpose. She reminds us that every level of growth requires a new level of commitment, and that comfort is the enemy of progress.
Whether you’re a leader, aspiring entrepreneur, or simply someone navigating a career transition, this episode is packed with wisdom that will inspire you to keep going—and keep growing.
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