Entertainment TV From Struggling Actress to Entrepreneur: Bethenny Frankel's Highs & Lows The lifestyle mogul is so much more than a former Real Housewives of New York City cast member By Dave Quinn Dave Quinn Instagram Twitter Dave Quinn is an Editor for PEOPLE, working across a number of verticals including the Entertainment, Lifestyle and News teams. People Editorial Guidelines Updated on March 23, 2021 03:48 PM Share Tweet Pin Email Trending Videos 01 of 33 LOW: Life as a Struggling Actress Bethenny Frankel/Twitter Frankel began her career in Hollywood working as a production assistant on Saved by the Bell in 1991. Three years later, she had made the transition to working in front of the camera — though the roles weren't necessarily flying in. Among her credits? The low-budget 1994 horror film Hollywood Hills 90028 that featured a sex scene and nudity. "I was in a movie when I was trying to be an actress in L.A. [and] I was laying topless in a scene on a rooftop — which is great because it shows that my boobs were big," Frankel revealed on a season 9 episode The Real Housewives of New York City, during a fight with Ramona Singer. "I don't regret it at all. I needed the money and I wanted to be an actress. ... It wasn't porn. It was a cheesy movie." 02 of 33 HIGH: Making Her Name on The Apprentice: Martha Stewart In 2005, NBC placed its bets on domestic goddess Martha Stewart to spin off Donald Trump's hit The Apprentice. The wager did not pay off — The Apprentice: Martha Stewart fell in the ratings and failed to get a pickup. But one person did succeed: Frankel, who placed second in the series. Stewart may have felt that Frankel didn't "fit in," but Frankel showed she had charisma to spare in front of reality TV cameras. 03 of 33 HIGH: The Real Housewives of New York City Jay Sullivan/NBC/NBCU Photo Bank/Getty Frankel's run on The Apprentice: Martha Stewart was just the beginning. In 2008, she joined the cast of The Real Housewives of New York City — once again helping a network launch their second installment of a potential franchise. This time, though, she was a hit. As the only Housewife in the group without a husband, Frankel's hunger for family and financial success resonated with viewers — and her humor instantly catapulted her to fame. 04 of 33 LOW: Bethenny Bakes Jemal Countess/WireImage Before Bethenny got into the booze business, she tried her chance at baking by launching a line of healthy treats. As fans on RHONY saw, it did not go well. One scene showed Frankel at a Tri-State big box store, begging people to take a free sample. 05 of 33 HIGH: Bethenny Goes into the Book Biz Neilson Barnard/Getty After forging a career as a personal chef, it was only natural for Frankel to start writing cookbooks. She published her first book, Naturally Thin: Unleash Your SkinnyGirl and Free Yourself From a Lifetime of Dieting, in March 2009. That December came her second title: The SkinnyGirl Dish: Easy Recipes for Your Naturally Thin Life. An evercise DVD (Body by Bethenny) and audio book (The Skinnygirl Rules) followed in 2010. Since then, Frankel has published a slew of titles, including A Place of Yes: 10 Rules for Getting Everything You Want Out of Life (2011), Skinnydipping: A Novel (2012), Skinnygirl Solutions: Simple Ideas, Extraordinary Results (2014), Cookie Meets Peanut (2014), and I Suck at Relationships So You Don't Have To: 10 Rules for Not Screwing Up Your Happily Ever After (2016). 06 of 33 LOW: Family Affairs Jamie Squire/Getty The death of Bethenny's father — famed race horse trainer Robert "Bobby" Frankel, who died in November 2009 — was emotional for the reality star. The two had an estranged relationship leading up to his passing, as she explained in a season 3 RHONY episode after he refused to see her when she attempted to visit him in Los Angeles before he lost his battle to cancer. Though he changed his mind and Bethenny did eventually see him before his death, she still chose not to go to his funeral. She told Sonja Morgan that Bobby said during their meeting that he had lived "a full life." Bethenny's relationship with her mother, Bernadette Birk, is not much better. In her book A Place of Yes, Bethenny wrote about Bernadette — who split from Bobby shortly after Bethenny's birth. Bethenny claimed she never felt "safe" with her mother, who allegedly drank excessively. The two have not been on speaking terms since — though Bethenny did reach out a few years back to attempt to foster a friendship between her mother and her daughter, Bryn. 07 of 33 HIGH: Baring It All on a Billboard Courtesy PETA In December 2009, Frankel joined PETA's 'Fur? I'd Rather Go Naked' campaign with her very own nude billboard in Times Square. 08 of 33 LOW: A Friendship Sours on National TV BravoTV Frankel found herself in a number of feuds with her fellow New York City Housewives throughout the years, but none were as hard to watch for fans than her fracturing friendship with Jill Zarin. The two original Housewives were fast friends during RHONY's first two seasons. By season 3, they had drifted apart, and misunderstandings and jealousy didn't help bring them back together. By the reunion the two agreed to leave their past behind them. Unfortunately, they meant their friendship too. 09 of 33 HIGH: Love, Reality Style Andrei Jackamets/NBC/NBCU Photo Bank/Getty She had been married before (to entertainment industry executive Peter Sussman from 1996–97), but when Frankel met pharmaceutical sales executive Jason Hoppy in late 2008, she was ready to say "I do" again! The couple walked down the aisle in March 2010 in an extravagant wedding at the Four Seasons Restaurant in New York. The journey to their big day was captured on Frankel's first Bravo spin-off, Bethenny Getting Married? — which premiered in June 2010 and became Bravo's highest-rated series debut to date. A second and third season of the show following Frankel and Hoppy's married life aired under the title Bethenny Ever After and was wrapped up in May 2012. 10 of 33 HIGH: Welcome to the World, Bryn! Albert Michael/Startraks On May 8, 2010, Frankel gave birth to daughter Bryn Casey Hoppy. After 30 hours of labor, Frankel delivered the tiny tot (who weighed in at 4 lbs., 11 oz.) via C-section five weeks before her scheduled due date. "She came out like a little doll," Frankel told PEOPLE of seeing her daughter for the first time. "It was amazing." 11 of 33 LOW: Not All Reality Is Created Equal Adam Larkey/ABC via Getty Another competition reality show, another second place finish for Frankel. But while The Apprentice: Martha Stewart felt like a step forward for the star, ABC's short-lived Skating with the Stars felt like a step back. The show, which premiered its first and only season in November 2010, was a total flop — as celebrities like Frankel, Vince Neil and Sean Young competed with skating pros for an esteemed panel of judges (including Johnny Weir). Perhaps the Place of Yes author should have come from a Place of No on this one. 12 of 33 HIGH: Skinnygirl Sells AKM-GSI It started in RHONY season 1, when Frankel ordered a low-calorie drink she dubbed "the Skinnygirl margarita" — a concoction that cut out sugary margarita mix in favor of straight-up tequila with splash of club soda and fresh-squeezed lime. The drink's catchy name played in perfectly to the low-cal trend exploding at that time. That was in 2008. By the following year, Frankel had a bottle and a business plan — launching the Skinnygirl Margarita (and Skinnygirl Cocktails) for the masses. Though the recipe was slightly modified from the one she ordered, the effect was still the same and fans couldn't get enough. In 2011, Frankel sold Skinnygirl Cocktails to Fortune Brands' Beam Global (now a part of Suntory) for a reported $120 million. Since then, she's helped grow Skinnygirl Cocktails to a big money business with lines of wines, cocktails and, of course, flavored margaritas. 13 of 33 HIGH: Shooting to the Top of the Power List Frobes In 2011, Frankel graced the cover of Forbes magazine's annual Celebrity 100 issue thanks to her successes with Bethenny Ever After, her third best-selling book and the Skinnygirl sale. The world's highest-earning reality star at the time, Frankel had earnings of $55 million, which also made her one of the top-paid celebrities of the year. 14 of 33 HIGH: Bethenny Mike Coppola/Getty With her Bravo spin-offs coming to an end, Frankel took the leap to daytime, co-producing an eponymous syndicated talk show with Ellen DeGeneres. The series debuted as a summer test run on June 2012 on six stations owned by Fox Television Stations before launching nationwide in September 2013. 15 of 33 LOW: Bethenny Neilson Barnard/Getty Unfortunately, ratings for Bethenny were not nearly as successful as sales for Skinnygirl. The show was canceled in February 2014, with final episodes airing through July 4. 16 of 33 LOW: Divorce, Reality Style Noel Vasquez/Getty After three years of marriage and months of rumors that the two were on the rocks, Frankel and Hoppy announced their split in December 2012, saying, "It brings me great sadness to say that Jason and I are separating. This was an extremely difficult decision that as a woman and a mother, I have to accept as the best choice for our family. ...We will continue to amicably co-parent our daughter who is and will always remain our first priority. This is an immensely painful and heartbreaking time for us." 17 of 33 LOW: Pajamagate Bethenny Frankel/Instagram Matching mother-and-daughter outfits happen a lot in Hollywood. But Frankel went one step further in July 2014, wearing her then-4-year-old daughter Bryn's Hello Kitty pajamas in an Instagram photo that many slammed after seeing the star glorify the fact she could fit in her preschooler's clothes. "This is my daughter's nightgown and PJ shorts. Think we're ready to start sharing clothes yet?" Frankel captioned the shot, which highlighted her slim physique in an itty-bitty T-shirt, boy shorts and fuzzy slippers. The photo was reportedly brought up in Frankel's custody battle months later. "No more pajamas!" Manhattan Supreme Court justice Ellen Gesmer told Frankel's lawyer. "It's not a joke. Her child is not a joke." 18 of 33 HIGH: B Real Productions FYI Not content to only star on television, Frankel decided to start making them in 2015, launching her own production company: B Real Productions (BRP). Their first project, Food Porn, premiered on the FYI network later that year. The unscripted series follows chef/restaurateur Michael Chernow as he travels to the find the most buzzed-about eats in America, inspired by the social-media phenomenon of posting pics of food with the hashtag #foodporn. Season 2 of the series kicked off in May 2017. 19 of 33 HIGH: At Home in the Hamptons Larsen & Talbert In 2015, Frankel bought a five bathroom, three -and-a-half bathroom summer home in Bridgehampton, New York. Abutting 40 acres of open fields and minutes away from the beach, the property features a pool, guest house and, most importantly, a space to entertain and relax offers from the craziness of city life. "In New York, you constantly have to go somewhere, do something, do an activity, go to the next thing," she previously told PEOPLE. "It's nice not to have to go anywhere. I love making it more fun to be at home." 20 of 33 HIGH: Returning to RHONY Patrick Ecclesine/Bravo She had left the series the skyrocketed her to household-name status after its third season, but Frankel returned after a three-season hiatus for season 7 in April 2015. She hadn't missed a beat, instantly cracking fans up with her quick wit and sassy comebacks. 21 of 33 HIGH: Moving On (and Out) Evan Joseph Due to her bitter divorce battle with ex-husband Jason Hoppy, Frankel found herself pushed out of their Tribeca apartment which she had purchased just before they split. So she bought a 2,392-sq.-ft. home in October 2014 for $4.2 million. After renovations which left her living in hotel rooms, Frankel was able to move into the two-bedroom property. It features a sunken living room with 14-ft.-high ceilings, open kitchen, triple-paned arched windows, a wood burning fireplace, a balcony and a landscaped atrium. The love affair with the apartment didn't last long. Frankel put it on the market in February 2017 for $5.25 million. 22 of 33 HIGH: Closing a Chapter Michael Loccisano/Getty; SplashNews After nearly four years in a bitter divorce battle, Frankel and Hoppy finally reached a settlement in July 2016. While the terms were private and confidential, both released statements through their legal teams expressing the joy they felt to be finished with the rancorous, longstanding split. Frankel had been open about her struggles throughout her "gnarly, nasty ordeal of a divorce" — telling PEOPLE in April 2016 that it had "gone on way too long." "I feel like I survived something," she said. "When it all shakes down, I'll be a woman who has not kind of just felt backed into a corner. I stayed strong and I did what was best for myself, my daughter, for women." 23 of 33 LOW: East Coast/West Coast Housewives Battle Bravo Frankel has always been outspoken, but her big mouth got her in trouble with Real Housewives of Beverly Hills fans when she criticized fan favorite Erika Girardi by calling her Erika Jayne music videos "cheap" when the RHOBH ladies visited Frankel's Hamptons house in season 6. Girardi maintained to PEOPLE that "nothing I do is low-budget," and Frankel eventually came around to praise Erika Jayne's style. 24 of 33 LOW: Haunted by Her Ex Raymond Hall/FilmMagic In January 2017, Hoppy was arrested after Frankel alleged he showed up at then-6-year-old Bryn's school and threatened her. (An NYPD spokesperson confirmed the encounter to PEOPLE, noting that Hoppy approached Frankel and "tried to provoke a fight." The spokesperson added that Frankel alleged Hoppy had sent her "numerous emails and FaceTime calls numbering in the hundreds after a cease and desist letter was sent on Nov. 22, 2016.") Hoppy was initially issued a restraining order and charged with one count of harassment in the second degree, one count of aggravated harassment in the second degree, and one count of stalking in the fourth degree. In June, he appeared in court where he was arraigned on additional charges, including one count of stalking in the third degree, another count of stalking in the fourth degree and some additional conduct. He has denied all charges, calling Frankel's actions "unjustified" in a statement through his attorney. Hoppy also rejected a plea offer in March. 25 of 33 HIGH: Saying Goodbye to Tribeca (and Hello to a Tidy Sum) Douglas Elliman Sold! In April, Frankel (with the help of Million Dollar Listing: New York star Fredrik Eklund) sold her Tribeca apartment (which had been a major sticking point in the former couple's drawn-out divorce from Hoppy) for full asking price of $6.95 million. More impressive? Eklund moved the 3,600-sq.-ft., 4-bedroom, custom-designed property in just one day. 26 of 33 HIGH: Spinning Out Gold Cindy Ord/Getty In May 2017, news came that Bravo had picked up her second B Real Productions show — an NYC-based real-estate flipping show starring she and Million Dollar Listing New York realtor Fredrik Eklund tentatively titled Bethenny and Fredrik Property Project. Two weeks later, news broke that she would be guest-starring on the next season of Shark Tank. 27 of 33 HIGH: Skinnygirl Products Michael Simon/startraksphoto.com It's not just booze! Frankel has turned the Skinnygirl brand into an empire — with nearly a dozen product extensions including sparklers, sweeteners, candies, dressings, popcorn, shakes, coffee, tea, shapewear, appliances and even Skinnygirl Market Fresh Deli meat. It's the best thing since sliced bread — and, honestly, it's only a matter of time until Skinnygirl makes that too. 28 of 33 HIGH: B Strong Takes Action Gary Miller Once Hurricane Harvey hit the city of Houston in 2017, Frankel and her B Strong charity sprung into action. The star raised $50,000 for the Houston and Corpus Christi chapters of Dress for Success and announced that her charity donated $30,000 to help women and their families who are in a financial crisis. Frankel and B Strong has gone on to help further relief efforts, including Hurricane Dorian and the ongoing coronavirus pandemic. 29 of 33 LOW: Death of On-Off Boyfriend Dennis Shields Alessio Botticelli/GC. It was announced that Dennis Shields had died of an apparent overdose in August 2018. Frankel and Shields began dating in 2016 — three years after she filed for divorce from Hoppy, and much of their on-off relationship was documented on The Real Housewives of New York. Despite multiple breakups, Frankel and Shields remained close before he died. Later, it was revealed that despite their complicated relationship, the two had considered marriage and Shields had even proposed and given her an engagement ring. 30 of 33 LOW: Hoppy Accuses Frankel of 'Dangerous Parenting' Raymond Hall/FilmMagic; Robert Kamau/GC Images; Alessio Botticelli/GC Images. Hoppy brought the death of Shields into his and Frankel's contentious custody battle over daughter Bryn at a hearing in August 2018. Frankel had asked for primary custody and full decision-making power but Hoppy expressed his desire to keep their joint custody arrangement the same. Hoppy's attorney Robert Wallack referenced reports that Shields had died of an apparent overdose, and said, "Our concern is while his death is very sad this raises serious concerns about Ms. Frankel's parental judgment," according to Page Six. He went as far as saying Frankel had exhibited "dangerous parenting" for allowing Shields around their daughter. Page Six also reported at the time that Frankel teared up during the hearing, and that Hoppy's lawyer requested that she be tested for drugs. The judge was reportedly "skeptical" of this argument given Hoppy had already expressed his desire to continue sharing custody. He said Hoppy was "throwing grenades" in the proceedings. Later in October 2018, the judge denied Hoppy's request that Frankel undergo drug and alcohol testing, telling Hoppy, "I think you are trying to exploit Ms. Frankel to embarrass her. The appeal is denied." 31 of 33 HIGH: New Relationship Status Bethenny Frankel, Paul Bernon. Charles Sykes/Bravo/NBCU Photo Bank via Getty; Alberto E. Rodriguez/Getty Two months after the death of Shields, Frankel started dating real estate developer and film producer Paul Bernon. "He's incredible," Frankel gushed on an episode of Watch What Happens Live in April 2019. "He's a beautiful human being inside and out." "And yes, Bryn knows him and loves him," she added. "They're very, very similar people." 32 of 33 HIGH: Leaving RHONY for Good Andy Cohen and Bethenny Frankel. Charles Sykes/NBCUniversal via Getty Frankel said goodbye to the New York City franchise again in August 2019, saying that she's ready to explore her next chapter. "It's time to move on and focus on my daughter, my philanthropy and my production partnership with Mark Burnett, producing and starring in shows which represent a shift in the conversation for women," said Frankel in a statement to PEOPLE. "With the changes in modern culture, I want to highlight the strength, confidence and unstoppable power that women have. My experience at Bravo has been an incredibly magical ride," she continued. "I am so grateful to them for highlighting my entrepreneurialism and allowing me to pave the way for many women to achieve their goals. I am excited for my future. The best is yet to come." Bravo did not respond to PEOPLE's request for comment. 33 of 33 HIGH: Engaged! Bethenny Frankel and Paul Bernon. Bethenny Frankel/Instagram PEOPLE confirmed in March that Frankel is now engaged to boyfriend Paul Bernon, and that she has finalized her contentious divorce from Jason Hoppy. The couple, who started dating back in 2018, recently sparked engagement rumors when Frankel was spotted wearing a massive diamond ring over the weekend in Florida. Diamond expert Mike Fried, CEO of The Diamond Pro, told PEOPLE that Frankel's engagement ring looks to be a 15-carat plus emerald cut center stone flanked by trapezoid side stones.