How They Made Their First Million

You can’t help but learn from and be inspired by the success stories of these four local entrepreneurs.

BY January 5, 2018
Sandra Stilwell Youngquist
(Photo by Alex Stafford)

First, let’s be clear: The headline was our idea. These self-made millionaires did not approach Gulfshore Life. We chased them, and in some cases, cajoled them a bit into sharing their stories while trying to allay their fears of appearing braggadocious. Thankfully, they saw value in offering inspiration. Real estate agent extraordinaire Jane Bond stressed the necessity of hard work. Hospitality maven Pat Carroll underscored the value of integrity. Business development guru Elliott H. Singer encouraged persistence. Powerhouse entrepreneur Sandra Stilwell Youngquist emphasized honesty. Their recollections offer lessons everyone could use, because even if we can’t all be millionaires, we can be better at whatever work we do. And, a few extra zeros in that bank account certainly wouldn’t hurt.


Jane Bond
You’re only as good as your last sale. — Jane Bond (Photo by Alex Stafford)

Jane Bond

Occupation: Broker associate at Coldwell Banker Global Luxury and principal of The Bond Group

Takeaway advice: “Put your foot on the gas and just keep going.”

As soon as Jane Bond stepped inside the nearly 12,000-square-foot penthouse, she knew it had to be hers. The contemporary style. The porcelain tile. The Gulf views. She had never seen any place like it in Naples. I don’t care what it takes, she thought. I have to have this listing.

Bond—that is indeed her given name—was up against three other agents. The initial contact came via referral. Her passion and enthusiasm, she thinks, clinched the listing. “I remember one of the seller’s associates saying to me, ‘You’re a breath of fresh air.’”

In January 2016, she listed the penthouse in The Seasons at Naples Cay for nearly $18 million. The condo sold in March 2017 for about $15 million. The path to that record-breaking sale and her first million was a matter of timing, negotiating and connecting with a specific buyer, Bond says. “Not everyone is walking around with $18 million in their pocket every day.”

It also took a commitment to stellar service.

“We have captains of industry who have decided to lie down their hats here,” she says. “If you can service your clients with concierge service, diamond key service, they’re going to refer you over and over and over again.”

That level of service entails: taking calls no matter the hour, listening more than speaking, not making promises she can’t keep, knowing the market, following up, negotiating creatively, working crazy long hours.

Real estate was not her first career, or even her second or third. Before moving to Naples in 2008 with her husband, a retired Brit, she worked as a flight attendant, an interior designer, and an entertainment manager. She had relocated from New York City and was bored without work. “All I did was run here. … I was like Dorothy clicking my heels, ‘Take me home.’”

After adjusting to the slower pace, she found her niche in real estate. She earned her license in 2010 and proved to be a quick learner. She won the rookie of the year award. “I knew I was on a track to be a top agent.”

She proved this with the record-smashing penthouse sale and took it as a cue to work harder. “I just put my foot on the gas. This was the time to go for it.”

There are days she finds herself working until 3 a.m., and she’s usually in her office by 7:30 a.m. Twice a week, she drives over to Miami as she builds her clientele on the other coast.

“You’re only as good as your last sale,” she says.


Pat Carroll
When opportunities would come up, whenever we could, we would make a leap of faith. — Pat Carroll (Photo by Alex Stafford)

Pat Carroll

Occupation: One of the managing partners and owners of Carroll Properties, a hotel and resort management company

Takeaway advice: “Integrity is the basis. It precedes you. When you leave employment, it follows behind. When people know they can trust you, they’ll reach out and do that much more.”

Pat Carroll prayed often during her 20-minute commute from her home in suburban Cincinnati to the hotel she owned and ran with her three sisters.

God, please order my steps.

She needed help. As a little girl, she thought she’d end up as a teacher or work in accounting, but never did she foresee operating multiple hotels.

It’s a prayer she would return to through the years as she and her partners came to own and operate 44 businesses, mainly in the hospitality industry, in eight states.

The adventure started small in 1964. Carroll was in her early 20s when she and her husband opened a gas station near Cincinnati. Customers often inquired about places to stay nearby. The couple decided to meet that demand and, two years later, opened a 21-room motel. Initially they didn’t have the money to buy a washer or dryer, so they’d load up the family van with sheets and towels and head to a Laundromat.

It wasn’t long until their little motel had neighbors. Two brothers built a 120-unit hotel. They had no experience in the hotel business, so they asked Carroll to be their general manager. This led to a longstanding partnership between the families. Through it, Carroll held the position of director of operations.

Carroll Properties, the company she owns with her now ex-husband, still owns the Best Western Fort Myers Waterfront, Gulf Star Marina on Fort Myers Beach and four restaurants within the properties. Their son is the company president.

But before all that, it was a joint venture with the brothers to open a 210-unit hotel in 1975 across from the new Kings Island amusement park in Ohio that brought in the first million. Early on, guests lined up out the door. But it’s hard to say precisely when they hit that financial milestone as they constantly reinvested.

“We probably never stopped to really celebrate,” Carroll says. “We just kept going. When opportunities would come up, whenever we could, we would make a leap of faith. And if we made bad investments, we would get out as fast as we could.”

Not that they had much time to reflect: She and her partners were invited to be a 250-unit host hotel for Kings Dominion in Virginia.

The demands of work and parenting two kids required fierce organization. Their daughter was injured during delivery and uses a wheelchair. Carroll hired people to help with errands, groceries and child care. One of their partners was a private pilot so they could visit properties and return the same day. “Our goal was always to be home for dinner with our family.”

Tenacity, timing and research were critical ingredients to their success, she says, but integrity was No. 1.

Her Christian faith guided her through professional and personal endeavors. Her daughter, also a Lee County resident, went on to college and has been married 16 years. After a friend invited her to private meetings with Mother Teresa in the 1990s, Carroll intensified her philanthropic work. In 2017, she was honored as a Grande Dame for PACE Center for Girls in Lee County.

“I just always stood for what was right,” she says. “I would tell the employees, ‘If you do the right thing, it’s going to work out.’”


Elliott Singer
The harder you work, the luckier you get. — Elliott Singer (Photo by Alex Stafford)

Elliott H. Singer

Occupation: Financial and business development adviser

Takeaway advice: “You’ve got to find a business or a passion that you really like. Something that you very much enjoy, and stay very focused.”

On a windy winter’s day in New York City, an ambitious young man felt about as gloomy inside as the weather outside.  

It was the 1970s. Elliott Singer was in his early 30s. The offshore mutual real estate fund where he had worked in advertising and marketing had collapsed. His career tumbled down with it. Singer had no choice but to move in with his new bride’s parents.

That cold day he was job-hunting when, in a borrowed copy of The Wall Street Journal, he spotted a quote that would change his life:

Nothing in the world can take the place of persistence.

Talent will not; nothing is more common than unsuccessful men with talent.               

Genius will not; unrewarded genius is almost a proverb.

Education alone will not; the world is full of educated derelicts.

Persistence and determination alone are omnipotent.

Something brightened inside Singer when he read it. “Do you mind if I tear this out?” he asked the paper’s owner.

Over the next few days, he lingered over the quote. Eventually, he’d frame it. It’s the nudge he needed in that moment to press on, double down and hone his focus. During his job search, Singer came across a story on a restaurant chain’s CEO in Forbes Magazine. Singer wrote to that CEO. The bold overture led to a job. Singer became the assistant to the president with the expectation of succeeding him.

A few years in, when the president opted not to retire, Singer decided to build his own business. At 38, he started what would become A+ Communications, and grew it into a telecommunications company worth more than $100 million.

His first million, he recalls, came in his mid-40s when he was raising private capital to grow the company. Sure, it was a confidence boost, but his worth did not affect his approach to business “one iota.”

“I was getting up early and staying late and paying attention to detail. It didn’t have so much to do with money. It was fun building a company. At the end, I had 3,000 employees in a company I had started from scratch.”

Through the years, the quote on persistence stuck with him.

Singer placed it in offices in the 38 cities to which his company bloomed. In his early 50s, Singer took the company public and stayed on as CEO a few years before selling it for $300 million and moving to Naples. He still keeps the framed quote in his offices.

“No matter what you’re doing, you need to be extremely focused on that particular task,” he says. “The harder you work, the luckier you get.”


Sandra Stilwell Youngquist
When you give somebody your word, the word is more important than having a signed contract. — Sandra Stilwell Youngquist (Photo by Alex Stafford)

Sandra Stilwell Youngquist

Occupation: CEO and owner of Stilwell Enterprises & Restaurant Group

Takeaway advice: “Be honest and true in all you do.”

Sandra Stilwell Youngquist was something of a wunderkind on Fort Myers Beach. She started her first business at 17 when she heard a fellow church member needed a cleaning crew. She put together a proposal for what would become a thriving bank cleaning business. “Before long, I had several vans and crews of people cleaning.”

Yet she knew a cleaning company wasn’t her destiny. The hospitality industry was in her blood. Her parents owned a hotel on Fort Myers Beach where she had been a maid, front-desk clerk, maintenance girl.

For two years early in her career, she owned the SandCastle Island Resort with a partner. But to have the equity to invest in the two-story hotel required sacrifice. She sold her home, moved into the hotel, and set to work improving and modernizing the fixer-upper of an investment.

That’s how, at the age of 22 and pregnant with her first child, she found herself on the cusp of a deal that would earn her her first million and set the stage for her career as an entrepreneur. They had sold to an interval ownership company. For months, she was terrified.

Would she get stuck owning half a hotel? Would the deal end up falling through? But the regular visitors bought in.

Through the sale she met James Newton, who was prominent in real estate and represented the buyer, and his wife, Ellie. Newton had been friends with Thomas Edison, Harvey Firestone and Charles Lindbergh.

She and Newton became partners in a property management company. Ellie and James became her mentors. “They taught me a lot about honesty and that when you give somebody your word, the word is more important than having a signed contract.”

Eventually, she decided to venture out on her own. She sought a hotel where she’d like to stay on vacation. In 1999, she bought Captiva Island Inn, and a few years later she bought out its restaurant.

Fast-forward a few decades. Stilwell Youngquist owns five restaurants along with the Captiva Island Inn. The inn’s restaurant, the Key Lime Bistro, has gone on to win national awards. In 2017, she was inducted into the Lee County Business Hall of Fame. For her continued success, she credits her faith in God and her parents, who instilled in her a strong work ethic and the role of sacrifice.

“You have to really work hard and know when to pull the plug,” she says. “No matter how much you know and how hard you work, it doesn’t always bring success.”


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