How Amber and Ryan Duncan keep winning in entrepreneurship

The year was 2008.

A young couple in Bradenton, who had met while working in the mortgage industry, was about to hit rock bottom.

As the United States real estate bubble burst, so did theirs.

Amber Duncan found herself in a humiliating situation. She was in line to get her Women, Infants and Children’s card.

The trustee told her, “I’m sure I’m going to see you here again.”

“You can bet your bottom dollar that you won’t see me, or anyone else I can help here, again,” she replied. 

Fast-forward to 2020. The Duncans own a debt settlement company, Reduce My Debts valued at $50 million, Ryan Duncan, Amber’s husband, established a regenerative agriculture farm on their 12-acre property in Bradenton, called Jubilee Organics, Amber owns two cupcake franchises and has launched Jackie, a clothing subscription and personal shopping service.

In the fall of 2015, Amber purchased a fitness center in Palmetto, which she rebranded and revitalized into LIVE Training Center. This location serves as a training gym for American Ninja Warrior competitors. Shortly after purchasing this location, Amber handed off the company to her brother to own and operate.

The couple’s latest entrepreneurial feat launched in the fall of 2019, Class Coach, an online learning platform that was right on time for everyone to be told to stay home.

When asked where their crystal ball was, Amber laughs. The “yin and yang” of Amber and Ryan is just a winning combination.


Where Amber is outgoing and loves to build, and grow, relationships, Ryan is more introverted, but brilliant, according to Amber.

“We teamed up and started working together,” Amber says. “We were completing each other’s sentences. He would sell the deals and I would process them and deal with the customer service piece. It was like magic.”

Unfortunately, timing and the national economy were outside of their control. 

“As you know, the mortgage business crashed,” she says. “For two young kids, like ourselves, we had four children at the time and I was pregnant with a fifth child, in an instant, we had lost everything.”

Ryan was still trying to keep income coming in as a mortgage broker, but the idea to do something meaningful was calling. The Duncans decided to answer that call.

Their first joint business was Reduce My Debts.

“It was exciting because we had something we could get behind,” Ryan says. “What rose out of the ashes of all this financial calamity, personally, ended up being that we were able to help people that were in the same situation we were in.”

Amber and Ryan, working together, is the common denominator in their recipe for success.

“We’re good partners. We balance each other,” Amber says. “There is a flip side. It can turn into all you’re doing is working. You have to remember you have a relationship, too.”

“There’s a learning curve,” Ryan adds.

Both Amber and Ryan agree they couldn’t have sustained if it had not been for their third business partner Harry Hedaya, who was also their previous manager when they worked in the mortgage industry. Harry currently serves as the chief information officer of Send it By Text, a digital marketing company. 

“We would not have succeeded if one of us was missing,” Amber says. “It’s all about the people and we still say that today with every business we own. If you put the right people together, there is absolutely nothing that can stop you.”

The company began to turn a profit after one year in operation and the Duncans never needed to add more seed money to their operations. For a while, Amber didn’t even take home a paycheck but was working until 10 p.m.

“I had a baby on Friday and was back to work on Monday,” she says before she bursts into laughter. “I don’t even know how I did it, to be honest. By the grace of God, we made it.”

clearwater entrepreneur magazine
Amber and Ryan Duncan at their Bradenton home.

In July 2020, the company handled more than 4,000 settlements and about $12 million in credit card debt. Reduce My Debts currently has about 150, mostly remote at the moment, employees.

“We found a problem,” Ryan says. “The way banks were communicating with their delinquent creditors needed work. And that need has never gone away.”

Once they found their secret sauce in the business, they were off to the races. It was time to build their oasis.


Jubilee Organics started as a passion project for Ryan after he was diagnosed with hypertension. He wanted to be more mindful of the foods he was putting on his family’s table. When they bought the property, where they built their home, it was intended to have land for a farm.

The farm produced an abundance of food, so it began to jar sauces and soups for sale on its website, reluctantly, as Ryan admits. He didn’t want to make a business out of it initially.

Amber adds with a laugh, “I don’t even cook.”

“People would pull in to just see the farm and I’d be like, this is our home,” she says with more laughter. “It was insane.”

In 2019, Ryan shut down the sauce and soup line.

“I ran it hard and just couldn’t get the numbers to work,” Ryan says. “I had a huge operation running. I gave myself a threshold and said if I’m not meeting these numbers by August of 2019, the party’s over.”

It was traumatizing for Ryan, he says. It was a major heart project for everyone involved. To grow things without chemicals and not use additives is a pricey operation to run.

“It was one of those [projects] that may have been a little ahead of its time,” Ryan says. “You got to know when to hold them and when to fold them.”

Now, the farm focuses on wholesale produce to local restaurants and suppliers, The Chiles Group being the most notable.

While the pandemic has raged on, Jubilee Organics has donated food when they could and provides tours to people who are interested in growing their own food.

“He opens people’s eyes to what they are ingesting because he saw the change that took place in his own body when he [started eating healthier],” Amber says.

Ryan says he’s very happy supporting Amber, and her business endeavors, and his main job, currently, is being a father to their five children.

The farm is a glorious thing to see. It’s a self-sufficient model where everything planted, and every animal on the property, serves a purpose.

florida business and wealth
Jubilee Organics is home to pigs, goats, chickens and ducks.

The pigs, two wild and one diva named Charlotte, help to dispose of dropped fruit and create manure. The chickens produce an abundance of eggs, which cannot compare to those you find in the grocery store, Ryan says.

There are goats –— two are babies — and ducks. And on another property up the road, there are cows.

The Duncans could close their gates and live off their land at any time and not miss a beat. They could take a stroll along the shoreline and relax on their private beach that looks out on the bay near Anna Maria Island. It’s paradise.

Just ask one of the many national magazines that have wanted to run photos of their home. Simple Living and even the Joanna Gaines, of Fixer Upper and Magnolia fame, has shown interest in the home design.

The Duncans have also been able to find retreats overseas. They own property in Rancho Santana Nicaragua, which provides them the ability to unplug.


Ryan is a fourth-generation resident of Manatee County and Amber was raised in Brandon.

“I’m a Florida boy,” Ryan says. “I grew up on the water. I never knew how I was going to make a million dollars being a fisherman, but those were my two goals. Fish and make a million bucks.”

Ryan attended Auburn University in Alabama and graduated with honors in economics.

Why Auburn? It’s where his father went and, of course, the football.

When Ryan moved back home after graduation, he bought his first house. From an early age, he was in love with the concept of saving money and being fiscally responsible, he says.

“I’ve been a compulsive saver since I was 12 years old. I had my first IRA at 13,” Ryan says. “I learned how fun it was to have that security. I learned at a young age how fast the ‘new’ wears off of stuff.”

Meanwhile, Amber graduated from Temple Heights Christian School in Tampa and attended Liberty University in Virginia.

In her second year in college, her parents got divorced and she came home to be closer to her family, including her three siblings.

She started working at the makeup counter for Estee Lauder and ended up staying there four or five years.

During that time she had her first child, a daughter.

“I was a single mom and struggling. I just knew I was going to work hard and hopefully, something would happen,” she says.

As luck would have it, she started working on earning her mortgage broker license and then the real estate boom happened. Not long after that, she met Ryan.

Amber ultimately returned to college to finish what she had started before life happened and is excited to graduate in December.

“It was all about completing that part of my life,” she says.


Amber owns two Gigi’s Cupcake franchises, one in Tampa and one in Gainsville. She originally opened the one in Tampa simply because she fell in love with the cakes and wanted them accessible to herself locally.

“I flew up to Nashville and my driver, at the time, brought this box to me and said, ‘you have to try these when you get to your room.’ As soon as I got to my room, I took a bite of it and was like, ‘Oh my gosh.’ For selfish reasons, I wanted to bring it to Tampa,” Amber recalls.

Amber ended up becoming the president of the board for the franchise in 2018.

“It’s a great company. I love, it because people smile when they come in,” she says.

She took over the Gainesville location in 2016 after it appeared in an episode of Undercover Boss.

They are the only two Gigi’s Cupcakes locations still open in Florida.

It wasn’t the last business Amber dipped her toe into for “selfish” reasons.

“I had tried every box subscription when I was the [chief operations officer] for the debt consolidation company,” Amber says. “I always joke, ‘My next business is going to be XYZ.’ But it really got to the point where I had a real concept.”

This time, Amber wanted a clothing subscription service that she felt was tailored for people. The company focuses on getting high quality, and classic, items from boutiques.

“It wasn’t about the clothes to me, it was about relationships,” she says. “I wanted someone who got me, knew me and could choose things for me based on what they know about me and my lifestyle.”, Amber’s fast-growing personal shopping, styling subscription service, is estimated to be worth $2.5 million.

She says brands like Good American and Misa are hot right now.

“We love picking out great clothes. We love textures. Our goal is to find a wardrobe that fits your lifestyle,” she says. “I wanted to empower women.”

Originally, the business was to be named Chatterbox, with a slogan, “Give all your girlfriends something to talk about.”

After a meeting with her branding team, and watching the documentary about Jackie Onassis the night before, she changed the name to Jackie.

“It’s about who she was as an individual,” Amber says. “She didn’t have to say much. She could walk into the room and her style, her presence and the confidence she carried said it all.”


The most recent business in the Duncan collection is Class Coach, an online support system for students in school, which was established in the fall of 2019.

“Originally, it was created for just online students, but now what we’re seeing with COVID and how school has changed,” Amber says. “It comes along and supports them emotionally, physically and spiritually.”

The company hired educators and professors to write a curriculum that goes to support students without being the teacher, or a parent, but more like a coach.

“Parents can’t play every role,” she says. “Sports have coaches for a reason. They can create empowerment and encouragement, giving you the tools. We’re putting kids through school. We’re giving them an education but we’re not giving them the tools to go out and actually use the education. That’s what Class Coach is all about.”

Every successful business the Duncan’s established has had two factors. One, the ideas were born out of the problems they faced in their own lives. Trusting those gut feelings of, “If we’re needing this, then other people must be too.”

Second, they’ve worked together. Pooling both of their strengths and making up for their self-proclaimed weaknesses.

When it comes to giving back, they are very involved and supportive of their church and they invest in their employees.

“One of my favorite things is to give stuff away,” Amber says. “I’ve been that way since I was a child.”

Amber also enjoys one on one mentoring with other women who are looking to establish their own business, with guidance and financial support.

“Just recently a woman came to me with this great idea, but doesn’t have the money to start it up,” Amber explains. “They don’t have the money. So I love investing financially in other women with great ideas.”

She recently launched a new website to help encourage women to seek guidance called Newborn Consulting. 

Amber and Ryan both agree that while they’ve seen success, it’s not without some failure.

“It’s important to note that we’ve invested in projects that haven’t worked too,” Amber says. “People think everything we touch turns to gold, but that’s not the case.”

“When you’re talking about a startup, something from scratch, especially if it hasn’t ever been done before. And that seems to be where we end up being. We don’t have a roadmap to follow,” Ryan says.

Amber adds, “We don’t want one though.”

It’s believable. It’s doubtful they need one.

You can just call them the comeback kids.♦

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