Sky Gillespie believes that some people are born to be entrepreneurs.

Although Sky has a degree in entrepreneurship, the real tipoff that she had that special something came one day as she studied the scene in her Manhattan office.

Sky was a recent college graduate, a resident of New York’s trendy Upper West Side, and she was working for a real estate software company.  It was time to take a risk. 

It was a five-year-old company that was wildly successful. “I saw a company where the people who had started at the beginning, when it was had little to no business and participated in building it from the ground up had the influence. As much experience as I gained, and as much as I loved living in New York, I thought it would be better for me to leave and help build Ripple Safety from the outset.”

Ripple Safety, headquartered in Fort Lauderdale, Florida, is an innovative solution for addressing personal safety that was founded by Sky’s brother, Rees Gillespie, in 2015. The idea came because their mother, a real estate agent (and former stay-at-home mother), often phoned Rees to say she was going to show a house to a stranger and felt a bit apprehensive. “There was no way that she could get to her purse, find her cellphone, type her passcode, dial 911, tell them who she is, where she is, and what her problem is, all while potentially having to defend herself,” says Sky. Ripple was born. Rees, exhibiting the Gillespie entrepreneurial spirit, began the uphill battle of starting from scratch.

“I was extremely passionate about being employee number two and helping to build a company from the ground up.”

Determined to get in at the beginning, Sky, now 26, made the move four years ago. “I was extremely passionate about being employee number two and helping to build a company from the ground up,” Sky says. She adds, “Today I am Head of Product at Ripple Safety and lead everything related to the customer experience and overall customer relations for both our individual and corporate accounts.”

She also raises capital, a dimension of her responsibilities she enthusiastically embraces. They started out by raising a $500,000 seed investment from local investors and quickly raised an additional $4 million after having proven the development of the product. Today, Ripple has raised over $5.5 million in capital and operates with a team of around twenty-five. The original idea was that a Ripple alert button would help professionals, such as her mother, have instant access to the help they needed, but it quickly caught on with customers young and old, regardless of their own personal safety challenges. For obvious reasons, it’s popular with women, but also popular with active older people who enjoy the sense of safety Ripple provides.  The monitoring team, Sky says, is located in the United States and operates 24/7/365. “Ninety-five percent of Ripple alerts are answered within 15 seconds,” she says.

“We wanted our Ripple subscribers to be able to rely on us regardless of their situation, so we developed a system where they can trigger both emergency and non-emergency alerts to the monitoring team,” Sky says. “If you’re in an uncomfortable situation—say you’re a woman walking to your car at the end of a parking lot, you’re a college student walking home from the library at night, a mom with a baby in your stroller and you’re leaving the mall and you just don’t feel safe, but you’re not in immediate danger—you may press the Ripple device one time to send our monitoring team a non-emergency ‘uncomfortable alert’. In the monitoring center, our team members are viewing your full physical and medical profiles, they have your real-time location, and they have the ability to dispatch the appropriate Police or EMS resources corresponding with your location. For this kind of ‘uncomfortable alert,’ they’ll call your cell phone in seconds. They will stay on the phone with you until you get to where you’re going, make sure that you’re safe, and in the event your situation escalates to an emergency, they can dispatch the proper emergency services right to your location, as well as relay your critical profile information to the first responders.

“If you’re in a genuine emergency, you press the device three or more times, to signal our monitoring team it is a true emergency, and they will place one phone call to you. If you don’t answer that phone call, the monitoring team will follow the preconstructed emergency instructions you have built out in your Ripple app, and dispatch either police or EMS right to your location without you having to say a single word. Some of our users have health conditions, and they will have it set to an ambulance, whereas many of our younger, female subscribers will have their profiles set to dispatch police.” 

Ripple’s discreet device is attractively designed to be the size of a dime. It is wearable, water-resistant, never needs to be charged, and connects via Bluetooth directly to your smartphone. Connected to the alerts you trigger from the Ripple device or Ripple app, is Ripple’s professional monitoring team. The Ripple monitoring team protects you 24/7 across the United States for the unbeatable price of just $14.95/month. “Consider the level of comfort and protection you receive from your home alarm system, we strive to continue that same level of security and peace of mind beyond the home, keeping you and your loved ones safe wherever you go,” says Sky. While Ripple is popular with women, it isn’t for women exclusively. “We actually have a fairly large portion of our subscribes made up of men. But the ratio is about 70:30 female to male,” Sky acknowledges.

Sky credits both her mother and her father with fostering an entrepreneurial spirit.

Sky grew up in Fort Lauderdale, with her four siblings. Sky’s mother launched her real estate career only after the youngest child was preparing to graduate high school. “Raising five kids, particularly as rowdy as we were known to be, would have been more than a full-time job for anybody. Fortunately, she kept us all in line and still balanced time volunteering for different organizations, and still does.” Sky went on to Florida State University in Tallahassee, another favored Gillespie family alma mater, where she immersed herself in business and real estate.  

She credits both her mother and her father with fostering an entrepreneurial spirit. Her father is an attorney, focused primarily on real estate and contractual litigation. Sky says, “My dad always instilled in us – if you want something for yourself go make it happen, it’s on you. He started from scratch and over time, he delivered on his opportunities when they presented themselves.  It was that individual spirit, wanting to forge his own path and control his own destiny as much as possible, that I think we all got a piece of.”

The benefits of being one’s own boss aren’t just financial, as Sky explains.

The benefits of being one’s own boss aren’t just financial, as Sky explains: “My father was always there when we were growing up. He never missed a parent-teacher conference. He never missed a recreational sports game. That’s something that you don’t genuinely understand and appreciate until you’re older, and you’ve had some real exposure to the challenges life inevitably has instore for all of us. So, that’s definitely where our passion for entrepreneurship and trailblazing originates.”

At the ripe old age of 26, Sky is carrying on a family tradition of taking risks and succeeding. Call it the Ripple Effect.