O.B. Osceola Jr. has warrior leadership in his blood. He is the descendant of a man who was at one time the most famous American Indian in the world, the man who ignited the Second Seminole War and resisted U.S. incursions on Native lands. The Great Osceola was also a father and husband to two wives, one of whom was African American, and he fiercely resisted America’s brutal institution of slavery. O.B. Osceola Jr. honors that lineage by carrying on the Osceola name, and by rising to become not only one of the most prominent Seminole business leaders ever, but also one of the most prominent business leaders of any ethnicity in the state of Florida and, indeed, in the United States. He is now blazing a trail in the multibillion-dollar NASCAR business, with the recent formation of Germain-Osceola Racing, a partnership he’s forged with Bob Germain of Germain Racing. Through that coalition he now helms a Native American–owned national series stock-car team, becoming part of NASCAR history as one of the two Native-owned NASCAR teams in the sport's history, sharing that distinction with Laguna Pueblo tribe member David Melton's Sacred Power Motorsports.
The drive for success that O.B. Osceola Jr. inherited from his forefather clearly has an indelible genetic footprint. His father, O.B. Osceola Sr., owns a private, Naples, Florida–based building company that generates $500,000 to $1 million a year in revenue called O.B. Osceola Sr. Builder Indian. Osceola Jr. started in his father’s company after graduating from high school before going on to become the president of Pro Investment Group International and the chief executive officer of Pro Games LLC. The 43-year-old currently owns Talako Construction, LLC, as well as Osceola Group Insurance, Inc., and is founder of Hard Rock Vodka, which was launched in 2011. He has constructed and managed many large-scale Seminole projects.
O.B.’s success as an entrepreneur has benefited the Seminole people in the past, and his recent move into NASCAR is likely to benefit Indian country. He hopes to involve Native American tribes in the fresh investment opportunities Germain-Osceola offers. “The more Natives that diversify their holdings and enter all possible markets, the more seriously corporate America and the world market will take us,” he says.
NASCAR receives more money from Fortune 500 companies than any sports or entertainment property in America. With 75 million fans, it is second in popularity to only football. It runs approximately 100 races in three national circuits annually, and each year generates billions of dollars from the sale of licensed apparel and accessories.
But even NASCAR has suffered during the current economic slowdown. Forbes reported that from 2007 to 2009, attendance at the track fell for each year from an average of 130,000 per race to 118,000. Lighter wallets, however, is not solely responsible for NASCAR’s recent dip in popularity. Even TV viewers have stayed away. While NASCAR television ratings from 2003 to 2008 outpaced all other professional sports, by 2009 NASCAR’s regular-season television ratings had fallen 21 percent since their peak in 2005. And, despite the recession, 2009 ad spending on NFL broadcasts was up 4 percent from 2005, to $2 billion. That same year, spending fell 16 percent on NASCAR’s premier Sprint Cup circuit, to $351 million.
One problem NASCAR has had, according to some pundits in the blogosphere, is that the organization is too monolithic, with too few women and people of color on the track. But O.B. has a plan for NASCAR that will benefit the company—and the Nations. According to O.B., who says he has been reading up on the demographics on NASCAR’s fan base, there “is no data” on the American Indian market. “This is a problem,” he says, “that I hope Germain-Osceola Racing can change. NASCAR needs to define the Native American population as a segment of the market and begin to spend its marketing dollars in Indian country and with Native charities. Native people are tremendous fans.”
Though O.B. has risen to become an owner in the NASCAR organization, his relationship with the company began when he, too, was just a fan. “NASCAR has always been a passion shared by my parents and me,” he says. “My love of stock cars probably began on the kitchen floor of our house with my first Hot Wheels car and plastic racetrack. My parents took me to my first NASCAR race and are to blame for my love of fast cars. We are an extremely close family, and I wanted to make my dad proud by actually finding a way of getting involved in NASCAR without having to drive in NASCAR.”
His family members, including the next generation of Osceolas, are still fans. O.B. says Bryce, his 16-year-old daughter, has been going to races with her parents and grandparents since she was 3, and O.B. III, who is now 4, “was at his first race while in the womb.” Malcolm, his 10-year-old stepson, cheers at the track with gusto, and O.B. also has a 13-year-old daughter, Tori, whom, he proudly reports, “sang the national anthem at a Daytona race last fall in front of thousands of NASCAR fans.”
NASCAR has been family-owned from its inception in 1948, and passing along the family business is an Osceola tradition that began when O.B. was just a child. “While most kids my age played dress-up and pretended to own businesses,” O.B. says, “my sister and I were full partners in our family-owned business by the time we could stand. We sold Seminole Indian art all over the country and learned to dance at pow wows during the summer to support our family. I remember dancing at festivals and fairs for tips when I was only 7 years old. While most kids were watching cartoons every Saturday morning, we were setting up a booth somewhere across the state or country.
“The funny thing is that I was born a businessman,” says O.B. “As a kid, I looked at the lemonade stand as a waste of time. I’d rather own the company that sold them the lemonade mix. I understood the nature of supply and demand at a very young age.”
His latest business venture in NASCAR may be riskier, and is definitely flashier, than owning a lemonade stand—or a lemonade-mix supplier—but O.B.’s portfolio of businesses suggests that he is a man who insists on maintaining balance in three key areas: in his family, with Indian country and on his bottom line. When considering investing in a business, O.B. thinks about the impact it will have on those three areas. “My favorite part of the NASCAR culture,” he says, “is the sense of family and importance of family. In addition to the fan base, the race teams are families, and that is important to me.”
That compatibility with NASCAR culture prompted him to make one of the boldest moves in Indian country this year—and honor Seminole culture. “My heritage has everything to do with what I invest in,” he says. “We are an unconquered people with a legacy to live and leave.”
O.B.’s grandfather, Cory Osceola, was leader of the independent Seminoles from 1920 to his passing in 1978, and he helped instill the sense of nation pride that, today, O.B. is helping to instill in others. “I want my people to know that the sky is the limit in terms of business opportunities,” he says. “We don’t have to only do business on the reservations or in arenas that are tied directly to the tribe. Don’t be afraid to reach for the stars!”