‘I worked 2 jobs for years’: Ex-radio DJ, 52, fought to survive as single mum overseas, now runs jewellery business with husband

She worked multiple jobs to survive, raised her eldest daughter as a single mother overseas and started over in Singapore at 40 years old.

Today, Maddy Barber, 52, is the founder of MADLY Gems, a bespoke fine jewellery brand she runs with her husband.

Behind the glitter and sparkle of her jewellery business, the road to success was far from easy. Along the way, the former radio DJ navigated financial struggles, career setbacks and several fresh starts.

Her ‘dream job’ as radio DJ proved challenging

Recounting her early years, Maddy told Stomp that she had always dreamed of becoming a radio DJ at Perfect 10, now known as Mediacorp’s 987FM, because of her love for music.

She took the leap and applied to be a DJ at the station in 1995, landing the job just before graduating from polytechnic.

However, her dream job proved more challenging than expected. While still finding her feet as a first-time radio DJ, Maddy became pregnant with her first child.

“It was a tough decision because I had just started my radio career,” she said, explaining that being pregnant at the time meant she would miss out on promotions.

“That was the old days,” Maddy said. “It’s not female empowerment. It’s shame and whispers behind your back.”

Describing that period as “incredibly tough”, she said becoming a mother was still “one of the best decisions” she had ever made.

After returning from maternity leave, Maddy had to take a “back seat” in her career. She was “shelved” and placed on a float shift, covering only for DJs who were on leave.

“That was how unimportant I was… It was a hard pill to swallow,” she said.

After her two-year stint at Perfect 10, Maddy decided to pursue overseas opportunities — first in India, then Thailand.

Life as a single mum, finding love in Thailand

Then a divorced single mother, she made the difficult decision to embark on a new life in Thailand with her young daughter, Elizabeth, who was still a toddler at the time.

“Thailand was never in my dreams. When the opportunity came, I said, okay, I’ll go,” she recalled.

Maddy subsequently joined Thailand’s Virgin Radio and became its programme director, taking on a more behind-the-scenes role compared to her previous DJ gig.

Earning a local salary as a new expatriate, she tried her best to build a comfortable life in a foreign land. She found herself parenting as a single mother, putting food on the table, paying for rent and arranging for trusted nannies to care for her daughter while she was at work.

While scrolling casually through an expatriate forum in Thailand, she came across a post by a “sporty guy” looking for someone “who gives as good as she gets”.

“So I replied and said I like that,” she recalled with a smile.

He introduced himself as Wez Barber, a geography and English teacher who was also based in Thailand, and their initial exchange soon blossomed into courtship.

The pair gradually exchanged more emails before meeting each other, and Wez proposed just six months later.

“The courtship was pretty short, in a good way,” she said, smiling. “I remember him telling me, 'My mom used to tell me you (should) marry someone you can’t live without, not someone you can live with.”

Excited as she was about their fresh start, Maddy knew to tread carefully. Early in the relationship, she told Wez that she might never be able to have a child with him because of a damaged fallopian tube.

“He said to me: ‘I’m in it for you, and Libby (Elizabeth) is as good as my kid,’” she recalled.

After they tied the knot, Maddy unexpectedly fell pregnant and gave birth to her second daughter, Alicia, whom she described as “in many ways, a miracle from God.”

Now married and raising two children, Maddy and her husband realised their salaries were barely enough to cover rent and their daughters’ school fees.

To make ends meet, she toyed with the idea of venturing into real estate.

When she noticed several vacant houses in the estate where they lived, she wondered why nobody was renting them out.

Seeing a business opportunity, Wez encouraged her to create a website listing the properties for rent, drawing on her interest in online forums and classified ads.

Although hesitant at first, Maddy used her “very broken Thai” and plucked up the courage to strike a deal with the local landlords. She soon became a freelance real estate agent, earning commissions for every listing, to supplement her radio salary.

She never thought her humble side hustle would eventually become a “full fledged business”.

“I started earning an extra $500, and then slowly became $800, $1,000 every month. When the time came, I left the radio to focus fully on the real estate agency,” she shared.

Her husband also quit his teaching job to join her in the business.

Looking back on her unplanned path, she said her sense of duty always came before personal enjoyment.

“You don’t (always) enjoy it at the beginning, right? There are people who rely on you. You just do it. Say a prayer every day that you get out of this situation in time and that better days are ahead.

“Because the same way that it doesn’t always shine, it doesn’t always rain as well.”

Within a few years, the business was bringing in “good money” and “financed the whole family” — eventually prompting Maddy and Wez to plan the sale of their real estate agency and move back to Singapore.

Return to Singapore, Kiss92 and early days of her jewellery business

When Maddy and her family returned to Singapore in 2009 after spending eight years in Thailand, she found herself back at square one.

Unable to continue working in real estate due to differences in the market, she decided to return to radio instead.

At 40, with two daughters to support, she took up a part-time job at 91.3FM that paid $2,000 a month.

“Obviously it was a bit discouraging,” she said. “It’s like after all these years, I felt like I was starting again.”

However, she said being a radio DJ came naturally to her and remained something she enjoyed. The part-time role also gave her more time with her daughters, who were still very young at the time.

Starting from the bottom once again, Maddy worked her way up to Kiss92FM, where she co-helmed the morning show with Arnold Jason for nearly a decade.

While thriving in what used to be her dream job, she couldn’t shake off the pull she felt towards gemstones and fine jewellery.

Maddy recalled that in her early 20s, she would often visit small jewellery booths to try on different pieces and experiment with various designs.

Over the years, she remained hungry for knowledge about various gemstones, driven by her belief that jewellery is among the most precious possessions one can own.

“It will outlive you and many generations to come. Honestly, I don’t think I would be passing a handbag down to my grandkids, but I will definitely pass a ring or two to them,” she chuckled.

Although she knew little about the pieces she collected in the early days, her husband once again encouraged her to turn her interest into a business by selling them.

In 2014, about four years into her role at Kiss92FM, Maddy founded MADLY Gems. She partnered with a designer and took charge of marketing as the business gradually grew. 

She went on to spend about seven years building MADLY while continuing to work full-time as a radio DJ.

“I loved my radio job, and I loved doing what I do at MADLY. I thought I had the best of both worlds,” she noted.

“I worked two jobs for years.”

Then came a turning point. Maddy said she had a moment of “conviction” one day when she felt she had delivered the best show of her career and would never be able to top it.

“(I thought) ‘I’m never going to do a better show than this,’ so then I was sure. You don’t want to hustle for your whole life. Believe me, it is tiring,” she said.

The experience also reinforced her desire to be more present for her loved ones — something her gruelling early-morning shifts at the station made difficult.

In 2021, Maddy decided to leave radio and focus on MADLY full-time. Today, the company has a team of more than 10 designers.

“I could never have dreamt it would become a business like this,” she said, beaming.

Running a business with her husband

At some point, her husband Wez joined MADLY to help manage its finances. What began as a temporary three-month stint has since turned into a 12-year partnership.

“He has learned to accept that and even enjoy working here,” Maddy quipped.

She admitted that working alongside her husband was not always easy, noting that working with family came with its own challenges. It took them about 20 years to learn how to communicate with each other, dating back to when they first ventured into real estate together in Thailand.

She recalled them arguing frequently, adding that people can sometimes be harsher towards their family members than others.

Over time, she learned that respect and kindness were just as important at home as they were at work, even though they played different roles in each setting.

“It took me a lot to learn that, but we are in a good place now,” she said.

Looking back on her journey

Asked what she would tell someone starting out on a $2,000 salary with a family to feed, Maddy admitted that she found it difficult to give advice without sounding patronising.

Her husband, however, offered her a perspective that resonated with her: everyone has to start somewhere.

“Most people actually started earning $2,000 at some point, and I did it twice,” she said.

Looking back on the many times she had to rebuild her life and career, Maddy said the journey taught her that life was ultimately about transformation.

“The worst you can be, is to be the same person.”

Have something to say? Join in!

Show all comments