The ENTERTAINER Founder and CEO Donna Benton: Lessons From Building, Exiting, and Reinventing As the ENTERTAINER marks its 25th anniversary, founder Donna Benton reflects on the lessons behind one of the region's most successful business stories.

"Back in 2001, I thought if I could one day sell this company for a million dirhams, that would be amazing," says Donna Benton, founder of the UAE's homegrown lifestyle savings app, the ENTERTAINER, reflecting on its humble beginnings 25 years ago.

Grounded, passionate, and driven, Benton has far exceeded those early dreams—growing her startup idea into a data-driven technology company now on track toward a US$300 million valuation. The ENTERTAINER book of 2-for-1 vouchers quickly gained traction, expanding beyond the UAE with launches in Qatar and Bahrain (2008), Oman (2010), Kuwait and Saudi Arabia (2012), and Singapore (2013).

Source: The ENTERTAINER archive

Yet, Benton still remembers her first breakthrough vividly—signing her very first merchant: five fine-dining and three casual restaurants at the JW Marriott in Deira. "If I could bottle the feeling I had when I signed the Marriott, and feel like that forever, it would be amazing," Benton says. "It was more money than I came here [to the UAE] with."

The backstory to this achievement is that Benton—then a 26-year-old newcomer to Dubai from Melbourne, with only US$3,000 in her pocket—personally managed every facet of the business in its early days, including conducting door-to-door sales. "I think that's the biggest thing for entrepreneurs, when you have an idea, work hard, and you are still at the embryonic stages, and then someone else believes in you and proves that it's actually working," Benton explains.

Benton's next defining milestone came in 2013, when she led the ENTERTAINER's bold transformation from a print publication to a fully fledged mobile app, marking the company's evolution into the digital age. Being among the first to embrace such technology was a risk that paid off – but not without its teething problems. "We went digital on January 2, 2014, and our app got hacked into, so it wasn't working while everyone was actually trying to use it," Benton recalls. "Since we still had the voucher books, we decided to send our staff out to hand people physical vouchers wherever they were, so they could use them. Everyone was running around."

Related: Against All Odds: Donna Benton, Founder, The Benton Group

Among other most defining chapters of Benton's entrepreneurial journey were two pivotal transactions—the partial sales of her company that marked both growth and transformation. In 2012, she sold 50% of the ENTERTAINER to an investment group with an aim to fast-track the company's growth and expansion beyond the region.

Then, in 2018, Benton took another leap, selling 85% of her remaining stake to GFH Financial Group, a Bahrain-based financial institution. "The first time was great, but it was part of our evolu- tion- we achieved in three years what would normally have taken eight," she says. "To be honest, I just needed a change. At the time, we were on a peak trajectory, but for me personally, it was the right timing. I was a single mom then, and I wanted more security and stability for my family."

Donna Benton signing the exit deal for the ENTERTAINER with her children in 2018.
Source: The ENTERTAINER archive

Before moving on to our next topic, Benton shares a never-before-told anecdote from her exit negotiations in 2018. "It was 17 men and me, and pretty much all were negotiating with each other," she says. "Everyone was just all over the place. I was the single biggest shareholder, and I actually wrote the figure down on a napkin next to the Chairman and I said, 'This is what I'll sell for. I really need to go to the bathroom and I'm hungry. If I come back and you've agreed, great. If not, I'm going for lunch.' The rest, as they say, is history.

Plus, Benton insists on sharing a piece of advice for fellow entrepreneurs. "If you're selling your company—unless it's a hugely distressed sale—don't sell it. If you're not getting what you want, ask yourself why. Build it up, do the math, and you might be able to sell it for more later. It's about knowing your worth and waiting for the right timing."

Soon after, she launched CAHA CAPO, a Dubai-based international swimwear label that operates under The Benton Group (TBG). She has also become a key shareholder and board member of Sunset Hospitality Group, a Dubai-headquartered hospitality investment and management firm. "If I'm being honest, it took probably a year or two to really come down from the ENTERTAINER. It wasn't my commercial baby anymore, but I still had my heart in it," Benton says. "But then I got quite happy doing what I was doing," Benton recalls. "I had started the Benton Group, CAHA CAPO. I joined Sunset Hospitality and I invest in property in the UAE, Thailand and Australia. She adds, "When I started the ENTERTAINER and we began taking dividends, I never bought Louis Vuitton bags or travelled business class. Instead, I'd put a deposit on a house, an apartment, or another property — and then rent it out."

In 2020, Benton announced her full exit from the ENTERTAINER, following the sale of her remaining 15% stake. It was meant to be the full stop to a remarkable chapter in her life and career — but instead, it turned out to be just a comma. "In 2023, our Chairman messaged me and said he wanted to have a chat about whether I would be open to coming back. It wasn't immediate that I said yes because I had a lot to consider," Benton says. "But my heart has obviously always been at the ENTERTAINER because I love making the unaffordable affordable for people."

Related: Starting Afresh: Launching A New Enterprise (After Exiting The Business You Led To Success)

In September 2023, Benton came back to the ENTERTAINER as a shareholder and CEO, restructured the company, and brought back her old team. "It had to go back to being a buy one, get one free concept that is uniform seven days a week, annually from January to December, and not what I call sort of a gym membership way. It's all about merchant relationships that you have, and we signed 1,700 merchants in the first year alone."

She adds, "I've been here two years now, and we basically got back to pretty much where we were when I sold, and we put an extra US$50 to US$60 million on the valuation in two years. That's something I'm proud of."

Source: The ENTERTAINER

Today, the ENTERTAINER offers seven location-specific products for the UAE, Qatar, Oman, Bahrain, KSA, Kuwait, Singapore, and a regional product for the GCC- making every experience more rewarding. Benton aims to harness data insights and improve user engagement to reinvigorate the platform for a new generation of consumers, building on the enduring appeal of its savings-driven model. "I don't think a lot of people realize how much money people actually have saved. And at the same time, how much footfall and revenue we've put through our app," she says. "Each year, we put US$1.3 billion into the economy. That's a savings of around US$350 million a year for people. Today, I still have people come up to me, like a month ago, a woman came up to me and said she was able to put a deposit on a house because of the savings that she had in the ENTERTAINER. It's changing lives. And I just love that it works for everybody."

She describes her management style as "fair, fun, but firm"—the three F's, as she calls them. "In the business, I would never ask someone to do anything that " I wouldn't do, but then I also expect results. I don't like laziness. I don't like clock watchers. What you put in is what you get out. I've never changed that and I never will. I think I'm still the same person I was 25 years ago. I'm extremely appreciative of what I have."

Looking ahead, Benton says her focus is on going deeper and wider across markets, doubling down on merchants -whom she considers the backbone of the business- and driving innovation through technology. The 2026 Entertainer app promises to elevate the user experience with an expanded network of merchants, a refreshed UX/ UI design, and integrated AI capabilities through its proprietary H.A.P.ITM system—delivering personalized recommendations and real-time responses.

"We always try to keep evolving, but we have to do it at the right time. I find people sometimes move too fast in tech and then it falls down. Sometimes, you have to let others do it and then see what's working and adapt."

As she reflects on her journey—past milestones, new ventures, and everything in between—Benton acknowledges that ambition never really fades, it simply evolves. "I still have goals and dreams, professionally and personally, so it's a balance," she says.