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The 25 wealthiest South Floridians

South Florida is a wealth magnet. The urban corridor from southern Palm Beach County to the Florida Keys is home, at least part time, to 19 billionaires and six millionaires with an estimated net worth of $200 million or more.

Many of these 25 success stories are familiar to the South Florida public, including longtime locals Miami Heat owner Micky Arison, the CEO of cruise giant Carnival; serial entrepreneur H. Wayne Huizenga; and activist and auto dealer Norman Braman. Some of the newer money in town is coming from such investment professionals as Carl Icahn, the richest billionaire with a South Florida home, which he bought in 1997. His net worth is an estimated $26.6 billion.

While South Florida’s economy turns largely on trade and tourism, the area’s richest residents have made their money in a broader mix of industries and professions often linked to geography and the vibrant, entrepreneurial spirit unrestricted by the generations-old social structure of cities like New York and Chicago. The 25 wealthiest people with a South Florida residence accumulated fortunes in fields ranging from investment management and information technology to television broadcasting, energy exploration and the distribution of air conditioners, according to a survey by Global Governance Advisors conducted for the Miami Herald.

Results are based on publicly trackable sources of wealth, such as ownership in public companies. As a result, some of the wealth fueling South Florida’s Bentleys and multi-million dollar condo purchases — such as privately held entrepreneurial endeavors — may not be reflected on our list.

“It’s a very diversified source of wealth compared to what you’d find in Silicon Valley and other parts of the United States,” said Luis Navas, managing partner of Global Governance Advisors.

Despite their diverse sources of wealth, the 25 wealthiest South Florida residents are undiversified in two other ways: gender — all are men — and race. This may in part derive from the “glass ceiling” that has traditionally kept female managers from rising to top management jobs, the region’s relative youth and the limited number of large corporations based here.

One issue: Pay inequity between genders. “Equal pay for equal work is not as real as it could be or should be … The gender pay gap is actually increasing again,” said Penny Shaffer, South Florida region president for Florida Blue and former chairwoman of the Greater Miami Chamber of Commerce.

While large corporations provide a ladder for at least some women to higher and higher management positions, compensation is limited at most corporations, and many fast-track female executives “are constantly being promoted at lower pay scales within the range,” Shaffer said. As a result, some senior women then leave to become entrepreneurs. But as studies indicate, many are cautious about borrowing the capital required to catapult their businesses into exponential growth.

Still, the rarified heights of the uber-wealthy may yet include more women and people of color. Cisneros Group, for example, is led by CEO Adriana Cisneros, daughter of board chairman Gustavo Cisneros.

And entrepreneurship may also be the path for people of color.

“Many of the top 25 wealthiest people in South Florida own a controlling equity stake in a large enterprise that they founded,” said Jaret Davis, co-managing partner of Greenberg Traurig’s Miami office. “Historically, in South Florida, wealthy blacks hailed from the professional classes — bankers, lawyers and doctors. Recently, we have seen an explosion of African-American entrepreneurs. As these companies scale, I believe you will see increasing numbers of African Americans within South Florida’s upper echelons of wealth.”

While many of the billionaires and multimillionaires with South Florida homes are longtime residents, a growing number are relative newcomers lured by absolution from harsh winters and a state income tax.

“There’s a growing trend where people spend six months and a day in Florida and maybe the balance [of the year] elsewhere, maybe California or Manhattan,” to qualify as Florida residents for tax purposes, Navas said.

More than just a winter home for the rich-and-retired set, South Florida also has become a principal residence for wealthy people “who are still in their earning years,” said Teresa Weintraub of Fiduciary Trust International of the South, which manages money for wealthy entrepreneurs and families from the U.S., and Latin Americans with U.S. business interests. “It’s not just that they’re coming to live in a nice home and retire.”

Weintraub, who was born in Cuba and raised in Miami, said the city “has become a very exciting place to live.” Although South Florida remains a popular place to retire, “because of the quality of life you’re seeing in Florida … and because of the tax structure you have, people in the prime of their lives are moving here permanently,” she said.

Wealthy people who live full time in South Florida sometimes started residing in the area in a second home, then “little by little, they were spending more time … until they moved here permanently,” Weintraub said.

New York-based billionaire Richard LeFrak, for example, has been spending more time in South Florida since he invested in the 2008 recapitalization of BankUnited, the largest locally based bank. LeFrak also invested in the remains of the former Corus Bank of Chicago, which counted many South Florida developers among its loan clients before the crash. “I think I ended up being the largest owner of unsold condos in Miami,” he said.

His investments in BankUnited and Corus Bank “were successful because the timing was good,” LeFrak said. “I wasn’t involved at all [in South Florida] until the financial crisis, and because I was in reasonably good shape in 2008, I had money for investment purposes. So between my exposure to BankUnited and the Corus Bank, I got an inside look at the Greater Miami area.”

He liked what he saw. LeFrak now has a second home in Miami Beach and two Miami-area real estate projects under way: renovation of the Gansevoort hotel in Miami Beach in partnership with Starwood Capital and resuscitation of an aborted North Miami development previously known as Biscayne Landing.

“I am now a huge enthusiast for South Florida,” LeFrak said. “I have seen the transition and the maturation of the Miami market. I can only compare it to two or three other markets in the United States as a magnet for international capital and as a desirable location for people to reside in and invest in.”

Realtor Jill Hertzberg said that for some homebuyers, profit potential is a major lure.

“What’s happened now is a whole different, almost sport, where people are getting into real estate in a very strong way and understanding it as a business opportunity, not just a place to live, or a second home,” said Hertzberg, who markets herself as part of a team called The Jills with another Coldwell Banker agent, Jill Eber. “They’re making money in real estate here,” Hertzberg said. When a billionaire New Yorker profits from home ownership in South Florida, “he goes back and tells two other big boys, who tell two others, and all of a sudden you’ve got a whole world of people like that here.”

“It’s the same thing with people from South America: A group will come in, and then another group will come in and say, ‘it’s safe, it’s wonderful, it’s a good place to put your kids in school,’ and, by the way, I made money there,” Hertzberg said. “The same thing has happened with Russians, but unfortunately their political situation has made it more difficult for them to come in now.”

Advances in communications technology have enabled more wealthy business owners to run their companies remotely from South Florida. “For lots of people, their businesses are more fluid … There are a lot of businesses you can conduct and live here in South Florida as your main residence,” Hertzberg said.

Realtors and condo developers aren’t the only South Floridians to benefit from these deep pockets. Companies run by Braman, Arison, Stuart Miller, Edmund Ansin, Huizenga, Jorge Pérez, Adriana Cisneros and others on the list collectively employ thousands of local residents. Public institutions including the Arsht Center for the Performing Arts, the New World Symphony performance hall in Miami Beach, the Frost Museum of Science, the Pérez Art Museum Miami and the University of Miami’s Miller School of Medicine have been made possible in part by gifts by the Arison and Miller families and individuals like Philip Frost, Pérez and philanthropist Adrienne Arsht (who gave $30 million for the performing arts center, though her wallet isn’t quite hefty as those on this list).

Having billionaires as neighbors might not be quite as good as being one, but it does have its benefits.

Following are biographical summaries for each of South Florida’s wealthiest 25 residents, including how they made their fortunes.

1. Carl C. Icahn

Where he lives: Indian Creek (seasonal).

Net worth: $26.6 billion.

Source: Icahn Enterprises.

How he made his money: Investing in undervalued companies and sometimes acquiring them and operating them more profitably than the previous management.

The story: Carl Icahn, 78, is a Wall Street titan with an activist approach to investing and impressive staying power. Formed in 1987, his Icahn Enterprises, L.P., (IEP: NASDAQ) is a diversified owner of big blocks of stock in public companies ranging from Apple Inc., eBay in. and Netflix Inc. to Forest Laboratories, Chesapeake Energy and Navistar International Corp. The investment side of his business is heavily involved in such shareholder activism as publicly agitating for changes in management and board governance and sometimes engaging in proxy fights to gain control of target companies. The operations side of Icahn Enterprises runs businesses in myriad industries. It operates companies that manufacture vehicle components for automakers, that refine petroleum and produce nitrogen fertilizer, that collect scrap metal, manufacture rail cars, and operate casino and entertainment properties.

Icahn Enterprises also has property operations that give its namesake a stake in Florida’s rebound from the real estate recession in the second half of the 2000s. Its developments include adjacent Vero Beach golf resorts Grand Harbor and Oak Harbor. According to Forbes magazine, Icahn bought a 14,000-square-foot Indian Creek Island vacation home in foreclosure for $7.5 million in 1997, long before most of the wealthiest residents of the island village in northeast Miami-Dade bought homes there.

2. Len Blavatnik

Where he lives: Miami (seasonal).

Net worth: $21.5 billion.

Source: Privately held Access Industries.

How he made his money: Netted billions of dollars by selling his share of a chemical maker and an oil production venture.

The story: Raised in Russia, Len Blavatnik, 57, immigrated to the United States in 1978, then became a U.S. citizen in 1984 and went on to become a successful investor and philanthropist. The Harvard MBA holder is founder and chairman of Access Industries, a privately held industrial group that owns businesses in natural resources and chemicals, media and telecommunications, and real estate.

Access has corporate offices in New York, Moscow and London. Its holdings in the United States, Europe and South America include large equity stakes in LyondellBasell Industries, a leading chemical company, and music company Warner Music Group, which has recorded artists ranging from Aretha Franklin to k.d. lang to Kid Rock. Blavatnik also has invested in Internet-based streaming music services Spotify, Deezer and Beats Music, according to Forbes magazine. Forbes also reported that Blavatnik late last year made a $2.37 billion investment in Lyondell Industries that appreciated to more than $10 billion. He earlier netted $7 billion when Access Industries liquidated its share of Russian oil production venture TNK-BP, according to Forbes.

Blavatnik is a part-time resident of South Florida, with a primary residence in London, but he is likely to have a permanent impact on the redevelopment of South Beach. He is a financial backer of Faena District, a multi-block, multi-use real estate project under way in Miami Beach, led by Argentine developer Alan Faena, who in 2012 started amassing hotel properties on Collins Avenue, including the old Saxony, Versailles and Atlantic Beach hotels. The Wall Street Journal reported that the Faena District will cover a six-block area and will encompass a hotel, retail center, arts center and an 18-story oceanfront condominium, called Faena House, with unit prices up to $50 million for the 14,000-square-foot penthouse.

3. Charles

B. Johnson

Where he lives: Indian Creek Island (seasonal).

Net worth: $7.9 billion.

Source: Franklin Resources Inc. (NYSE:BENO).

How he made his money: Investment management.

The story: Charles B. Johnson, 81, retired in June 2013 as chairman of the board of Franklin Resources Inc., a San Mateo, California-based money management company doing business as Franklin Templeton Investments. Johnson, who previously served as chief executive officer of Franklin, began working for the company more than 50 years ago, when its assets under management totaled $2.5 million. Franklin was managing $846 billion of assets just before Johnson retired. He also has served as an officer, director or trustee of various Franklin Templeton mutual funds. He has a home on Indian Creek Island in northeast Miami-Dade County. “My wife and I have been coming to Florida periodically all our lives, and in 2012, we became permanent residents,” Johnson said in an email exchange. “Franklin Templeton has over 100,000 investors who live in Florida. We also have large offices in St. Petersburg and Fort Lauderdale, as well as Miami, with over 11,300 employees in the state. … Our Fort Lauderdale trading desk makes over $30 billion in equity trades annually in over 40 financial markets around the world.”

Johnson said his best advice for young people starting out in business is a statement by former U.S. President Calvin Coolidge, which is engraved on a plaque hanging on his office wall: “Persistence … Press on. 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 will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent.”

4. Richard LeFrak

Where he lives: Miami (seasonal).

Net worth: $6.6 billion.

Source: LeFrak Organization.

How he made his money: Real estate development.

The story: New York City native Richard LeFrak, 69, has lifted his family’s real estate development business to new heights. When his father, Samuel LeFrak, died in 2003, New York-based, family-run LeFrak Organization already was “one of the largest private building firms in the world,” according to a New York Times obituary. The company has a portfolio of mostly residential and office properties concentrated in New York, Los Angeles and London.

Richard LeFrak, who joined the LeFrak Organization in 1968 and became its president in 1975, was appointed chairman and chief executive officer in 2003. Part of his billion-dollar fortune came from his successful investment in BankUnited in 2008 when the bank was in financial trouble. “I was part of the original money that recapitalized the bank,” he said.

LeFrak served four years as a director of BankUnited before selling his shares in the largest South Florida-based bank. New York-based LeFrak has a second home in Miami Beach where he resides “part time but increasingly more time,” he said in a phone interview. “It’s for business reasons because I have several projects under way down there. And also, I like it.”

He also invested in the acquisition and renovation of the Gansevoort hotel in Miami Beach, and has bought the land in North Miami for an aborted development that had been called Biscayne Landing. Young people going into business must “not be afraid to fail” but must pay close attention to every detail of their enterprise, LeFrak said. “You have to show up all the time. Businesses succeed mostly because the owner, the founder, takes an interest in everything, every little detail, especially in the beginning when it’s a baby. You can’t let it grow up by itself. You really have to be devoted to it.”

5. Micky Arison

Where he lives: Bal Harbour.

Net worth: $6.2 billion.

Source: Carnival Corp.

How he made his money: Worked with his father to build the world’s largest cruise company.

The story: Micky Arison, 65, has been with the cruise company his father founded for more than 30 years. After starting in the sales department, promotions to reservations manager in 1974 and vice president of traffic in 1976 helped prepare Arison to become the president of Carnival in 1979. The company went public in 1987, raising $400million for expansion, and by 1989, Arison had engineered Carnival’s acquisition of Holland America Line.

Other acquisitions followed: Carnival Corp. is the holding company for Carnival Cruise Lines and many other cruise lines including Holland America Line, PO Cruises, Princess Cruises, Cunard and Costa Cruises. Carnival expanded its fleet from 73 ships in 2003 to 101 ships as of mid-2014; seven new ships are due for delivery on dates from 2014 to 2016. Arison has been chairman of the board of directors at Doral-based Carnival since 1990 and a director since 1987. He served as the CEO of Carnival Corp. (formerly known Carnival Cruise Lines) from 1979 to July 2013.

Arison’s father, Carnival founder Ted Arison, died at age 75 in Tel Aviv in October 1999. In a New York Times obituary, the newspaper noted that Ted Arison was widely regarded as the “godfather of the modern cruise industry.” Carnival has faced operational adversity in recent years, and its net income has declined in the last two consecutive fiscal years.

In January 2012, a ship carrying Costa Cruises passengers wrecked along the Tuscan coast of Italy, killing 32 people. In February 2013, an engine fire disabled the Carnival Triumph in the Gulf of Mexico, exposing more than 4,000 people aboard the ship to broken toilets and unsanitary conditions. These incidents, “including the associated negative publicity, have resulted in lower cruise ticket pricing from prior levels. However, we believe that these events will not have a material long-term impact,” Carnival said in a quarterly financial report filed July 2 with the Securities and Exchange Commission.

The company’s stock has been trading in the high $30s lately, well above its sub-$30 stumble right after the deadly shipwreck off Italy. Arison’s net worth could take a dip even if Carnival stock remains buoyant. Forbes magazine, which annually estimates the value of National Basketball Association franchises, reported that the move by NBA star player LeBron James to the Cleveland Cavaliers from the Miami Heat could reduce the market value of the Heat franchise from $770 million, currently the seventh-most valuable franchise in the NBA.

“There is no substitute for hard work,” Arison said in an email exchange. “I tell young people just starting out to work hard, learn everything they can about the business and find a mentor to help guide them and expand their thinking. Everyone has ideas and something to contribute, so listening to different points of view is also very important.”

Arison says he recruits good people and supports them while refraining from hands-on micromanagement. South Florida “has played a huge role in my life and career and what I’ve been able to accomplish,” he said. Since the 1972 startup of Carnival, “I’ve spent the better part of my life working in Miami and building the company from three ships to a fleet of more than 100 ships.” South Florida “continues to help drive our growth,” he said, citing easy access to the Caribbean “and the beautiful setting here.”

6. Donald J. Trump

Where he lives: Miami (part time).

Net worth: $4.1 billion.

Source: Real estate, television.

How he made his money: Started in the construction business with his father in Brooklyn, became a successful Manhattan real estate developer, diversified into book publishing and television production.

The story: Donald Trump, 68, who made much of his fortune in the New York City real estate market, has referred to Florida as his second home. But Trump rarely seems to be vacationing in South Florida, where he has been an active real estate developer and redeveloper. Trump became a periodic Palm Beach resident after his 1985 purchase of Mar-a-Lago, the historic estate once owned by cereal heiress Marjorie Merriweather Post and investment icon E.F. Hutton. Trump converted Mar-a-Lago into a private social club in 1995. Four years later, in 1999, he opened Trump International Golf Club, a $40 million golf course within a seven-minute drive of Mar-a Lago. The Trump Organization acquired the Doral Golf Resort Spa in Miami-Dade County in June 2012 and is spending $250 million to renovate the 800-acre golf property, renamed Trump National Doral Miami. He also developed a golf course in northern Palm Beach County called Trump National Jupiter.

Trump began his career by working in the construction business with his father, Fred C. Trump, with whom he shared an office in the Sheepshead Bay section of Brooklyn. The ambitious son later became a leading developer of residential high-rises and hotel properties in Manhattan and took his talents to other fields as well. His 1987 autobiography, The Art of the Deal, has sold more than 3 million copies. By January 2004, Trump had a deal with the NBC Television Network to produce and star in the reality TV show The Apprentice. In 2005, he unveiled his personally branded line of men’s apparel and accessories, the Donald J. Trump Signature Collection, and in 2012, he launched his own fragrance, “Success by Trump.”

Anyone starting out in business today should “make sure you are doing something that you love,” Trump said in an email exchange. “It will make the obstacles seem less problematic than if you are struggling to do something you are lukewarm about.”

Mar-a-Lago and his golf course properties in Palm Beach County and Miami-Dade County constitute “a very healthy addition to my best holdings,” Trump said. “South Florida has been wonderful to me.”

7. Gustavo Cisneros and family

Where he lives: New York. The company is headquartered in Coral Gables and run by CEO Adriana Cisneros, who lives in Miami Beach.

Net worth: $4 billion.

Source: Cisneros Group.

How he made his money: Took over the family business his father founded and turned it into a media industry leader.

The story: Gustavo Cisneros, 69, was only 23 years old in the late 1960s when he took over the leadership of a diversified Venezuelan family business in that his father, Diego Cisneros, had founded. The second generation of family management proved impressive. With the founder’s son Gustavo at the helm, Cisneros Group grew to become one of the largest privately held media and entertainment conglomerates. A milestone in the development of Cisneros Group was its 1960 acquisition of a television channel that ultimately became Venevision, the leading national TV network in Venezuela. Gustavo Cisneros began his career at Venevision.

The $13.7 billion sale of Venevision to a private equity consortium in 2007 may have been one of the most personally rewarding deals that Gustavo Cisneros ever engineered. The family patriarch now serves as co-chairman of the board of Cisneros Group with Steven Bandel, a former chief executive officer of the family business. Adriana Cisneros, daughter of Gustavo Cisneros, replaced Bandel as CEO last year. From 2006 to 2013, she lived in New York and built a niche in the family business by developing its digital media operations, a field of increasing focus at Cisneros Group. The group encompasses a mix of business interests ranging from telecommunications, television production and broadcast television to consumer goods, resort properties and a 6,000-acre real estate investment in the Dominican Republic.

8. Phillip Frost

Where he lives: Miami Beach.

Net worth: $3.7 billion.

Source: Pharmaceutical development.

How he made his money: Built and sold two drug-development companies, the first for about $575 million, the second for $7.4 billion.

The story: Phillip Frost, 77, a former professor of dermatology at the University of Miami’s medical school, teamed up with business partner Michael Jaharis to acquire drug-development company Key Pharmaceuticals in 1972. Frost was chairman of the board and a major shareholder of Key when he and Jaharis sold it to the old Schering-Plough pharmaceuticals company for about $575 million in 1986. Frost went on to invest in a generic drug developer in South Florida named Ivax Corp. He was the chairman and chief executive officer of Ivax from 1987 until January 2006, when Israel-based Teva Pharmaceuticals bought Ivax for $7.4 billion. Frost became co-chairman of Teva shortly after its 2006 acquisition of Ivax. He has been chairman of Teva since 2010, when longtime chairman Eli Hurvitz resigned due to health problems.

Now Frost is preparing to step down as chairman of Teva. “I had agreed to become chairman several years ago when the then-chairman became ill,” Frost said in a phone interview. “He was a good friend, and I agreed to take on the responsibility for a certain time, and it has now gone beyond the time I had anticipated, and with my other activities here in Florida, I could be more focused.”

For example, since 2006 he has served as chairman of Miami-based investment banking firm Ladenburg Thalmann Financial Services. Opko Health Inc. is another one of his Florida priorities. He has been chairman and CEO and a major shareholder of the Miami-based public company since 2007.

“Opko is doing extremely well,” Frost said in the Sept. 8 phone interview. “Just this morning, an announcement went out that a product we licensed to another company successfully completed the clinical trials, and a new drug application was submitted. … This is a new drug for the prevention of nausea and vomiting associated with cancer chemotherapy, and it has a good possibility to be the best product in the market, since a single tablet is enough to protect the patient for five days.”

But the billionaire doctor’s investments range well beyond healthcare. “It’s a matter of strategy for me,” Frost said. “I believe in diversification in every possible way.”

Frost is a major shareholder and a director of premium liquor supplier Castle Brands, and he is a major shareholder of Vector Group Ltd., a leading cigarette manufacturer through its Liggett Group LLC subsidiary. Its real estate subsidiary New Valley LLC owns a majority of high-end residential property agency Douglas Elliman. In August, Frost led a group that invested in preferred shares of Drone Aviation Holding Corp. in Jacksonville. “I like the people [at Drone]. They are young people and very knowledgeable about the product,” said Frost, a former director of military aircraft contractor Northrop Grumman Corp.

For people starting out in business, “the important thing is what business you choose,” Frost said. “It’s important to pick businesses that have the potential for long-term growth and preferably with high profit margins.” South Florida has been an effective launching pad for his career. “For me, it has been very successful,” Frost said. “It’s a great place to live. … For us, it’s been easy to attract talent. People want to live here.”

9. Terrence

M. Pegula

Where he lives: Boca Raton.

Net worth: $3.3 billion.

Source: East Resources Inc.

How he made his money: Increased interest in the extraction of gas from shale rock.

The story: Terence M. Pegula, 63, is a self-made billionaire who collected a fortune from a technology-driven surge in gas production from shale rock. He was born and raised in Carbondale, Pennsylvania. After graduating from Scranton Preparatory School, he enrolled at Penn State University with a major in mathematics, but to stay in school he got a scholarship to enter the university’s petroleum and natural gas engineering program — a decision that set him on a rewarding path in the oil and gas industry. He graduated Penn State in 1973 with a bachelor of science degree and got his first job with Getty Oil Co. in Victoria, Texas.

In 1983, Pegula borrowed $7,500 from family and friends to start East Resources Inc., and he built the independent oil and gas exploration business into one of the largest privately held companies in the United States — with a helping hand from advanced oilfield technology. Hydraulic fracturing, or “fracking,” has improved the economics of shale-gas extraction, making it financially more feasible. Fracking is an emergent technology that involves high-speed injections of fluids and other materials that stimulate oil and gas flow from shale rock formations by creating fractures within them. In 2010, oil industry giant Royal Dutch Shell paid $4.7 billion for the assets of East Resources, including land in the so-called Marcellus Shale. The Marcellus is a massive shale rock formation in the Appalachian region of the United States, where East Resources had acquired 650,000 acres by June 2009.

The $4.7 billion asset sale to Royal Dutch Shell has allowed Terrence Pegula and his wife Kim Pegula to go shopping: They paid $189 million to acquire the Buffalo Sabres team in the National Hockey League in 2010, according to the Buffalo News. The Pegulas recently made a successful bid to acquire the Buffalo Bills, the National Football League franchise. Their $1.4 billion purchase from the estate of the late owner Ralph Wilson, who died in March, was approved by NFL team owners at their Oct. 8 meeting.

10. Igor Olenicoff

Where he lives: Lighthouse Point.

Net worth: $3.2 billion.

Source: Olen Properties Corp.

How he made his money: Office and residential buildings in Florida, California, Nevada and Arizona.

The story: Igor Olenicoff, 72, has amassed a real estate empire stretching from coast to coast in the United States. It includes a cluster of apartment buildings in Broward and Palm Beach counties.

According to the website of Olen Properties, the company’s South Florida apartment properties include Weston Place in Weston, Club Lake Pointe and Players Club in Coral Springs, Delray Bay in Delray Beach, Manatee Bay and Indian Hills and Whalers Cove in Boynton Beach, Sanctuary Cove in North Palm Beach, and Villas of Juno in Juno Beach. Olen Properties also has commercial and industrial properties, mostly in California but also in two Florida locations. Olen operates Quantum Town Center in Boynton Beach, a 117,000-square-foot commercial building, and the Delray Commercial Center in Delray Beach.

In 2007, Olenicoff pleaded guilty to falsifying his 2002 federal tax return by failing to disclose foreign bank accounts to the Internal Revenue Service. As part of his plea agreement, he paid $52 million in back taxes to the IRS and was sentenced to two years of probation and 120 hours of community service. According to Forbes magazine, Olenicoff has been preparing his daughter Natalia Ostensen to take over the management of Olen Properties.

People going into business today should “pick a business or career that cannot be shipped abroad or purchased abroad,” Olenicoff said in an email exchange. “Although the standard of living in other countries will improve and thereby raise the cost of labor there, they will always be able to do it less expensively. Our labor will continue to go up; our technological superiority gap will continue to narrow with other countries, particularly China and Russia. … This has been coming for a long time and why I selected real estate some 40 years ago. … Our real estate cannot be imported nor exported.”

Olenicoff said South Florida accounts for “a solid 30 percent of my company’s growth and success. South Florida, I am convinced, will continue to be a wonderful place to live, raise a family, work and invest in. It has all the necessary ingredients to continue along its success path.”

11. Edward

S. Lampert

Where he lives: Indian Creek (off Miami Beach).

Net worth: $3.1 billion. Source: ESL Investments, Inc.

How he made his money: Hedge fund management.

The story: Edward S. Lampert, 52, founded the hedge fund company bearing his initials in 1988. ESL Investments Inc. is in Bay Harbour in northeast Miami-Dade County. Lampert has invested in many retail companies. For example, ESL is a major shareholder of Fort Lauderdale-based AutoNation Inc., the nation’s largest automotive retailer. Lampert sometimes serves on the board or in the management of companies in which ESL owns large equity stakes. He served as chairman of the board of Kmart Holding Corp., which emerged from bankruptcy in 2003 and became a profitable retailer before its 2005 merger with Sears, Roebuck Co.

He currently is chairman of the Sears Holding Corp., the parent company of the Sears chain of department stores, and has served as chief executive officer of Sears since February 2013. His hands-on investment in Sears has produced disappointing results. Sears stock (NASDAQ: SHLD) recently traded around $27, well below the level of late 2013, when it topped $50. The Sears stock slump has contributed to an exodus of investors from ESL. Bloomberg News reported in June that Lampert distributed $393 million of AutoNation shares to cover investment redemptions by ESL clients.

12. Fred DeLuca

Where he lives: Fort Lauderdale.

Net worth: $2.8 billion.

Source: Subway.

How he made his money: Co-founded the Subway chain of sandwich shops.

The story: In 1965, Fred DeLuca, now 67, was a teenager who wanted to become a doctor and was searching for a way to help pay for college. A friend of his family, Dr. Peter Buck, suggested that DeLuca open a restaurant specializing in submarine sandwiches and loaned DeLuca $1,000 to get started. They opened their first restaurant in Bridgeport, Connecticut, in August 1965 and set a goal of opening 32 more by 1975. The co-founders in 1968 to put the Subway brand name on their restaurants.

In 1974, DeLuca and Buck were the owner-operators of 16 restaurants in Connecticut, and they decided to sell Subway franchises in order to expand the restaurant chain at a faster pace. In 1984, the company began expanding abroad by opening a location in Bahrain. By the end of the 1980s, Subway had locations in Puerto Rico, Canada and the Bahamas. Today the privately held Subway chain based in Milford, Connecticut, has more than 37,000 locations worldwide.

USA Today reported in May that DeLuca had resumed his work schedule at Subway after treatment for leukemia, including chemotherapy and a bone marrow transplant. The newspaper also reported that DeLuca, a Fort Lauderdale resident, spends most of his time traveling to visit Subway franchisees and “has no plans to retire.”

13. Robert

E. Rich Jr.

Where he lives: Islamorada.

Net worth: $3 billion.

Source: Rich Products Corp.

How he made his money: Built the frozen food products business his father started.

The story: Robert E. Rich Jr., 73, followed in his father’s footsteps and built the family business with a focus in frozen food products. Buffalo, New York-based Rich Products Corp. generates more than $3 billion in annual worldwide revenue. On its website, the company calls itself the “founder of the non-dairy segment of the frozen food industry.” According to the website, the late Robert E. Rich Sr., founded the company in 1945 after he discovered that “a soya bean substance could be frozen, thawed and whipped to serve as a vegetable-based replacement for whipped cream.” Rich’s Whipped Topping was the first in a line of non-dairy foods that Rich Products introduced, including Coffee Rich, “the nation’s first frozen non-dairy creamer,” which first appeared on supermarket shelves in 1959.

The founder’s son first made a name for himself in sports. Rich Jr. was an accomplished hockey player at a preparatory school in Buffalo and at Williams College, where during his senior year he was co-captain of the school’s hockey team. He graduated from Williams College in 1963 with a bachelor of arts degree, and joined the family business in 1964 as president of Rich Products of Canada Ltd. It was a new division of Rich Products with a new manufacturing plant in Fort Erie, Ontario, a short drive from the parent company’s headquarters in Buffalo. Rich then started and staffed the company’s first marketing department. In addition to mentoring from his father, Rich earned a master’s degree in business administration in 1969 at the University of Rochester Simon School of Business.

In 2006, Rich became chairman of the board of Rich Products Corp. after the death of his father, and his wife, Melinda Rich, became vice chairman. CampdenFB, a publisher focused on family businesses, ranked Rich among the 50 top family-business leaders in the world in 2012, noting that the annual revenue of Rich Products had grown to $3billion from $28million when the founder’s son joined the company.

14. Bharat Desai and family

Where he lives: Fisher Island.

Net worth: $2.7 billion.

Source: Troy, Michigan-based Syntel Inc.

How he made his money: Co-founded a successful information technology company with his wife, Neerja Sethi.

The story: Bharat Desai, 61, is chairman of the board of Syntel Inc., a leading source of integrated information technology to help large companies transact business in the fields of financial services, healthcare and life sciences, insurance, manufacturing, retailing, logistics and telecommunications. He co-founded the company in 1980 with his wife, Neerja Sethi, who has served as a director and vice president, corporate affairs, throughout the company’s 34-year history. Desai has an MBA in finance from the University of Michigan’s Stephen M. Ross School of Business, and a bachelor of technology degree in electrical engineering from the Indian Institute of Technology in Bombay, India.

Publicly held Syntel has more than 24,000 employees and a market capitalization of $3.7 billion. Forbes magazine ranked Syntel 15th in its 2012 list of “America’s 200 Best Small Companies.” Syntel’s net income last year was $219 million, up 85 percent from $118 million in 2009. The company provided IT services to 120 customers last year in the United States and Europe, including American Express and State Street Bank, its two largest customers in 2013. Syntel has shared its success by running S’Prayas, a volunteer-based program to educate underprivileged children in communities where the company operates.

15. H. Wayne Huizenga

Where he lives: Fort Lauderdale.

Net worth: $2.6 billion.

Source: Jon Doe Enterprises.

How he made his money: Led the development of Waste Management and Blockbuster Entertainment, often via business acquisitions.

The story: H. Wayne Huizenga, 76, made his fortune almost entirely from successful investments in years past, according to Forbes magazine. But he remains an active investor. He started with a single garbage truck and turned his hauling business into Waste Management Inc., the nation’s largest garbage hauler with $13.9 billion of revenue last year. Huizenga acquired video rental company Blockbuster Entertainment, rolled up similar companies in an early-1990s acquisition spree, and ultimately sold Blockbuster in 1994 to entertainment conglomerate Viacom for $8.4 billion. Huizenga put his money behind another waste hauling company, Republic Services, which diversified into auto dealership acquisitions, then changed its name to AutoNation in 1999 and subsequently sold its waste-hauling business.

Huizenga also has been a successful real estate investor. In 1996, he founded Boca Resorts. When he sold the company for $1.25 billion in 2004, Boca Resorts owned the Boca Raton Resort Club and two Fort Lauderdale properties, the Hyatt Regency Pier 66 Hotel and Marina, and the Radisson Bahia Mar Resort and Yachting Center.

Huizenga also invested in three professional sport franchises: He paid $95 million in 1991 to acquire the Florida Marlins baseball team, $50 million in 1992 for the Florida Panthers hockey team, and about $140 million in 1994 for majority ownership of the Miami Dolphins football team. Huizenga has since sold his stake in all three teams except for fractional ownership of the Dolphins.

He continues to hold sizable equity stakes in publicly traded companies, among them Psychemedics, which tests for drug abuse through analysis of hair samples, and Swisher Hygiene, a provider of institutional and industrial cleaning chemicals and restroom cleaning and restocking services.

Huizega said in an email exchange that he advises people starting their own business to “surround yourself with great people. People are what make businesses prosper.” He also said he has lived in South Florida for 60 years and never wanted to live anywhere else. “The fabulous weather, wonderful amenities and sense of community allowed us to recruit and retain great people,” he said. “That’s why we headquartered our companies here and that, in turn, is why we were successful.”

16. Jorge Pérez

Where he lives: Miami.

Net worth: $2.2 billion.

Source: Related Group.

How he made his money: High-rise condominium development.

The story: Jorge Pérez, 64, transformed the South Florida skyline during the high-rise condominium building boom before 2008, and his development company Related Group survived the bust that followed.

A Cuban immigrant, Pérez was economic development director of the city of Miami before he became a developer. He founded Related Group in 1979 with New York developer Stephen M. Ross, now owner of the Miami Dolphins. Pérez initially got rich from the construction of rental apartments then got richer as the nation’s busiest builder of luxury condominium towers. Pérez and Ross developed City Place, a mixed-use downtown landmark in West Palm Beach. Pérez built high-rise condominiums in South Beach and Sunny Isles Beach.

But he left his biggest mark in downtown Miami, where, starting in 2002, he built a dozen high-rises with a total of 5,500 condo units. Pérez preserved Related Group by renegotiating its debts and diversifying its business. He endured some big losses along the way. Lenders for his Icon Brickell condo development seized two of its three towers in 2010. By June 2011, the condo units in the third tower that Pérez retained were nearly sold out. The housing market collapse in 2008 and a health scare (a benign mass on his pancreas) prompted Pérez to reexamine his personal and professional priorities. He contributed $40 million in cash and art to the old Miami Art Museum, now known as Pérez Art Museum Miami, or PAMM, located in a new home on Biscayne Bay that opened in December 2013.

Although Pérez has restructured Related Group to make it less reliant on condominium projects, he has hardly abandoned the condo market. In early 2014, Pérez broke ground for construction for the SLS Hotel Residences Brickell and opened MyBrickell, his first post-crash condo development in Miami’s urban core.

Pérez said in an email exchange that people starting in business should “pick something you love and pursue with great dedication and passion.” He also said, “South Florida has been absolutely essential in my growth. I owe all to the openness of this community and the generosity and acceptance of the people that live here.”

17. Norman Braman

Where he lives: Indian Creek (off Miami Beach).

Net worth: $1.9 billion.

Source: Braman Motors.

How he made his money: Automotive retailing.

The story: Philadelphia native Norman Braman, 82, co-founded a vitamin retailer and merged it with another company in 1967. Then he and his wife, Irma, who have been married for 58 years, moved from southeast Pennsylvania to southeast Florida in December 1969.

“I had a degree of success before coming here,” Braman said in a phone interview, but “my great success in life has been in South Florida.”

According to trade publication Automotive News, Braman owned the nation’s 27th-largest auto dealership group in 2013: His 14 dealerships last year sold about 32,000 vehicles and collected $1.68 billion in total revenue.

Braman credits nonstop business reinvestment for his success in the automotive retailing industry. “My philosophy has always been to constantly reinvest in your business … It’s something you have to do. You can’t sit back in business; if you sit back, you fall back,” Braman said in a phone interview, citing the current expansion of his flagship location just north of downtown Miami. “In Palm Beach County, we’re in the process of building three new dealerships,” he said. Over the years, Braman Motors has added not only new locations but also new brands to its automotive product line. “When we started off in the car business, Cadillac was our dominant franchise. Now we sell everything from Kias to Bugattis,” he said.

Braman bought the Philadelphia Eagles franchise of the National Football League in 1985 and sold the team in 1994. The New York Times reported that Braman bought the team for $65 million and sold it for $180 million. He never again invested in a professional team after his nine-year ownership of the Eagles. “That was enough,” he said.

Braman also has used his success to serve in South Florida as both a philanthropist and an activist. The Norman and Irma Braman Family Foundation funded the opening of the Braman Family Breast Cancer Institute at the University of Miami’s Sylvester Comprehensive Cancer Center. The Bramans also have supported Lotus House, a Miami shelter for homeless women and children, and the Greater Miami Jewish Federation, among other philanthropic organizations.

However, Braman may be best known as a civic activist who has backed campaigns to recall former Miami-Dade County Mayor Carlos Alvarez from office and to defeat such controversial proposals as tax-funded improvements of sports facilities. “I really believe you have to stand for something in life,” he said. “If you don’t stand for something in life, then you’ll accept anything. And that’s what happens in society when we don’t stand for principles.”

Braman said people starting in business today should make protection of their reputation their top priority: “When you start out in life, the most precious thing you have is your name, and you just want to make sure, whatever your choices are, to value that more than anything else.”

18. John W. Henry

Where he lives: Boca Raton (seasonal).

Net worth: $1.6 billion.

Source: Fenway Sports Group.

How he made his money: Commodities trading and team ownership in professional sports.

The story: John W. Henry, 65, got rich in commodities trading, rich enough to allow him to buy the since-renamed Florida Marlins baseball team from Wayne Huizenga for $150 million in 1999. Henry sold his stake in the Marlins after he and a group of investors acquired the Boston Red Sox in February 2002. The New York Times reported that Henry and his investor group paid $660 million for the Red Sox. The performance of Henry’s commodities trading firm lagged in the aftermath of the global financial panic of 2008, according to the Reuters news service, and he closed the Boca Raton-based firm, John W. Henry Co. Inc., in 2012.

Now Henry is well into his second career as a team owner in professional sports. He is the principal owner behind the 2001 formation of Fenway Sports Group, which has a portfolio including the Red Sox, English Premier League soccer team Liverpool FC and their home stadiums. Henry’s company also owns 80 percent ownership of regional television network NESN (New England Sports Network) and 50 percent of NASCAR racing team Roush Fenway Racing. The Boston Red Sox have won three World Series championships (in 2013, 2007 and 2004) under Henry’s ownership.

In an email exchange, Henry said he would advise people starting in business today to find a professional passion: “You can’t work hard enough at whatever it is you want to be successful at, so you had better love what you are doing.” Henry said, “although I spend my summers up north,” South Florida has been his principal home for the last 25 years, “so I owe a lot to the area. I’ve been fortunate to have several careers during that span.”

19. Stuart A. Miller

Where he lives: Miami.

Net worth: $900 million.

Source: Lennar Corp.

How he made his money: Home building.

The story: Stuart A. Miller, 56, is still trying to put a near-depression in the housing market behind him and his home building company, Miami-based Lennar Corp. Miller has been a director of the company since 1990. He succeeded his father, the late Leonard Miller, who founded Lennar in 1954, as Lennar’s chief executive officer in 1997, five years before his father died July 28, 2002, of liver cancer, according to the South Florida Business Journal. Stuart Miller was chairman of commercial property subsidiary LNR Property Corp. until Lennar spun off of LNR as a separate company in 1997. Miller also served as president of Lennar from 1997 to 2011.

New York Stock Exchange-listed Lennar stock recently was trading at share prices around $39, about 11 percent below its 52-week high of $44.40. Miller was cautious in assessing Lennar’s prospects on the company’s Sept. 17 conference call with analysts to discuss second-quarter financial results. “Before this downturn, anything below 1 million housing starts in a year was considered almost a housing depression. This recovery is just now getting us back to that level of starts,” Miller said on the call. “Generally speaking, the market has continued a slow and steady recovery that is markedly different from past down-cycle recoveries. History would suggest a more vertical recovery, especially given the severity of the economic decline. This recovery has been a decidedly different experience as the slope of recovery has been shallow, and the expected acceleration has not materialized.”

20. Edmund Ansin

Where he lives: Miami Beach.

Net worth: $1.5 billion.

Source: Sunbeam Television Corp.

How he made his money: Inherited a real estate fortune, diversified into broadcast television.

The story: Edmund Ansin, 78, inherited a fortune in real estate and built a television broadcasting business atop it. Ansin learned how to manage money and his father made plenty to manage. Ansin earned his undergraduate degree at the Wharton School of Business and Finance. His -Ukrainian born father, Sidney, a shoemaker in Boston, went on to become a successful Florida real estate investor in the 1950s, according to Forbes. The magazine also recounted in an article about the Ansin family fortune that Ed Ansin and his father paid $3.4 million in 1962 to buy a local television station affiliated with the NBC television network, then called WCKT and later renamed WSVN. Ansin not only renamed the station but reinvented the delivery of local TV news in terms of faster pacing, grittier content and more hours a day devoted to local news.

Ansin set Channel 7 apart in other ways as well, notably his 1989 decision to run WSVN as an independent station after losing his affiliation with the NBC network and refusing to sell the station as part of a conditional deal to affiliate Channel 7 with the CBS network. WSVN ultimately affiliated with the Fox Network and Ansin’s navigation of the affiliation transition proved a success. Trade information publisher TVNewsCheck reported earlier this year that Channel 7 news audience ratings were unmatched “after 20 years or so of domination in English-language news” in South Florida.

21. Sean John

‘Diddy’ Combs

Where he lives: Miami Beach (part-time).

Net worth: $700 million.

Source: Diversified business ventures, especially a vodka promotion deal with supplier Diageo.

How he made his money: Hip-hop music recording and production and other business activities that include promoting Ciroc vodka.

The story: Sean John “Diddy” Combs, 44, started his career as a hip-hop music recording artist and producer and went on to establish an apparel line under the Sean John brand, a cable television channel called Revolt TV and a marketing agency, Blue Flame.

In a March 2011 article, “Why Diddy Will Be Hip-Hop’s First Billionaire,” Forbes magazine reported that Combs’ most lucrative asset was his 2007 agreement with Diageo, the world’s largest supplier of beverage alcohol, to promote its Ciroc vodka brand. The magazine said the agreement entitled Combs to a share of any profits from Ciroc vodka sales and to part of the proceeds if Diageo were to sell the Ciroc brand. The deal appears to be paying off for both parties. During the first two years of Diageo’s alliance with Combs, the company’s annual shipments of Ciroc vodka vaulted from 120,000 cases to 400,000, according to Forbes. The magazine estimated that the value of Combs’ deal with Diageo is in the “mid- to low-nine-figures,” while the rest of his business interests, including his record label Bad Boy Records, have a cumulative value of about $100 million.

So, Combs may indeed become a billionaire before his peers in the hip-hop music field.

22. Bruce

R. Berkowitz

Where he lives: Miami (seasonal).

Net worth: $500 million.

Source: Fairholme Capital Management, LLC.

How he made his money: Investment management.

The story: Bruce R. Berkowitz, 56, is the founder, managing member and chief investment officer of Fairholme Capital Management. He has a concentrated equity investment style, making big bets on relatively few stocks that most investors avoid. Purchases of stock in Bank of America and American International Group, or AIG, in 2011 helped to produce handsome 2013 returns on investment in his $8.8 billion-asset Fairholme Fund, according to trade publication Institutional Investor.

Berkowitz, a Miami resident since 2006, said in an email exchange that “Miami has all the resources we need, plus we get to live and work in a beautiful environment. Our tag line is ‘Ignore the Crowd,’ and our location here helps us maintain our distance and independence from the chatter of Wall Street.”

Berkowitz earned a bachelor of arts degree in economics from the University of Massachusetts in 1980. He is chairman of the board of the St. Joe Company, a publicly held Florida-based real estate developer. r of the Decade” in 2010.

Berkowitz said in an email that he advises people getting into business that any industry they find appealing has promise.

“It doesn’t matter what you do, if you really like it,” he said. “To be successful requires huge effort. Twenty-four/seven for decades is the definition of instant success. So you’ve got to love what you do, and if you don’t, try something else.”

23. Albert

H. Nahmad

Where he lives: Miami.

Net worth: $300 million.

Source: Watsco Inc.

How he made his money: Acquired control of a Miami company that became an industry leader.

The story: Albert H. Nahmad leads not just a company but an industry. He is the chairman, president, CEO and principal shareholder of a multibillion-dollar distribution business.

Born and raised in Panama, Nahmad relocated to the United States in 1958 to attend the University of New Mexico and settled in South Florida in 1973, where he has been a full-time resident since. “The first building block of our distribution business was a company acquired 25 years ago, located in Deerfield Beach,” Nahmad said via email. “We have acquired over 60 businesses since, but all of our original roots are firmly planted in South Florida.”

In 1972, he acquired a controlling interest in Coconut Grove-based Watsco Inc. from its founder, William Wagner. In 1989, the company made a successful switch from manufacturing to distribution. With 2013 revenue of $3.7 billion, Watsco is now the largest distributor of air conditioners, and heating and refrigeration equipment in its industry. His son Aaron J. Nahmad is a director of Watsco and the company’s vice president of strategy and innovation.

The CEO of Watsco advises someone starting out in business to consider financing the acquisition of a successful company. “Building on a successful business is a simpler, lower risk idea than starting from scratch,” Nahmad said in an email exchange.

24. Mike Fernandez

Where he lives: Miami.

Net worth: $200 million.

Source: MBF Healthcare Partners.

How he made his money: Used his managerial experience in the healthcare industry to invest successfully in healthcare-related businesses.

The story: Miguel “Mike” Fernandez, 62, is chairman of a private equity investment firm in Coral Gables called MBF Healthcare Partners. MBF focuses on investments in healthcare service providers. He and his wife, Constance Fernandez, have five children.

A serial hands-on entrepreneur, Fernandez has successfully run many of the companies in which he and his partners have invested. He was founder, president and CEO of Group Tech Systems, which developed a national database of group health insurance information.

Fernandez advises people getting into business to try to exceed their own expectations. “Do not reach for your potential. Reach for the unreachable,” he said in an email exchange, but “avoid debt whenever possible,” and “be the dumbest person in the room, as this will accelerate your development.”

Fernandez also said by email that South Florida has provided him a useful sense of likely U.S. business trends: “By looking at Florida’s changing demographics, I believe that you are seeing our nation’s future. Living in Florida has been like having a free look at tomorrow’s stock prices. It’s a peep into the future, and it’s a unique crystal ball.”

25. Laurans

Mendelson

and family

Where he lives: Coconut Grove.

Net worth: $200 million.

Source: Heico Corp.

How he made his money: Real estate investments, and his acquisition and development of Heico Corp.

The story: Laurans Mendelson, 76, was an accountant in New York City during the 1960s when he and his wife Arlene and their two sons relocated to Miami, where some of her family members already resided and worked in real estate. After the Mendelsons settled into a then-unincorporated Pinecrest community in southeastern Miami-Dade County, Laurans became a successful real estate investor and developer and got his sons Eric and Victor involved in the property business. By the time Eric and Victor were in college, Mendelson had switched his investment preferences from real estate to public companies, and his sons invested along with him and suggested target companies to buy and flip for profit.

But the Mendelsons saw greater potential in long-term ownership, so they acquired control of Hollywood-based Heico Corp., a manufacturer of aircraft replacement parts. Led by Laurans Mendelson as chairman and sons Eric and Victor, the co-presidents of the company, Heico now has a market capitalization of $3.19 billion, way up from $25 million when they bought control of Heico in 1990. New York Stock Exchange-listed Heico stock recently was trading at share prices near $47, about 28 percent below the 52-week high of $65.04.

Mendelson would advise someone starting out in business to “do what you enjoy doing and focus hard.” He also said in an email exchange to focus on more than money, “just do a good job and remember that your customer must get good value, respect and quality products.”

The chairman of Heico also said that Heico’s South Florida home has contributed to its success: “South Florida is a great source of quality life and fine people to work with you. Also, it’s a great business area with a very pro-business and entrepreneurial atmosphere.”

INGENUITY REAPS REWARDS

Although South Florida’s wealthiest residents have made their money through varied businesses, nearly all have benefited from hard work and inventive approaches. Sean John “Diddy” Combs, left, No. 21, has parlayed an entertainment career into a clothing brand, cable TV venture and marketing venture. Mike Fernandez, right, No. 24, is a serial entrepreneur in the healthcare industry.

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