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Craig Steven O’Dear, The Story of an Athlete Becoming a High Profile Lawyer

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Being a lawyer is difficult. It is a huge responsibility since their arguments can determine the fate of large amounts of money, and who goes to jail or goes free. It requires dedication, hard work, and endless hours. Few have achieved the highest ranks of the profession, but Craig Steven O’Dear is among those few who have done so.

An American lawyer, Craig Steven O’Dear, is a corporate litigator and legal advisor who has managed to establish himself as one of the finest corporate trial lawyers in the country. Due to his passion and hard work, he has been consistently recognized for his efforts in The Best Lawyers in America, Chambers USA, Missouri & Kansas Super Lawyers since 2006.

STORY OF AN ATHLETE

Born on June 26, 1957, in Northeast Missouri, Craig S. O’Dear is the son of H.C. O’Dear and Martha Lou O’Dear. His father was a farmer while his mother was a school teacher. He spent his childhood on a hog farm south of Lewistown, where he completed his high school education. 

Craig was an accomplished athlete in high school. He was a prominent basketball player and track athlete and played quarterback on the first-ever Highland High School football team. His parents were very proud and kept records of his athletic years. His father drove him to play basketball with the  Quincy  Herald-Whig publisher’s kids on a  YMCA  team, beginning in the fourth grade, every Saturday.

When Craig was a student, the school only offered a basketball program, and there was no football program. Craig’s father was a member of the school board. He, along with other local leaders, decided to start a football program. Coach Pat Wozniak was hired as the first football coach.

Coach Wozniak formed the first football team of the school comprising the school’s star basketball players and farm boys who had never played organized sports. Wozniak led the team to a 9-0 record in their first year, acknowledging the efforts of the young and confident athlete, Craig O’Dear. The coach said, “Without the quarterback, that wouldn’t have been possible to have that record. That was a big, strong, smart kid.” He graduated from Highland High School in Ewing, Missouri.

Craig’s success in football, basketball, and track in high school landed him a football scholarship at the Missouri University of Science and Technology. O’Dear played football and ran track at the university while pursuing an engineering education. He graduated with an engineering degree in 1979.

Apart from having a stellar background in sports, his father paid for Craig’s flight lessons, and also encouraged him to learn to fly. As of today, Craig has been a private pilot for 30 years!

STORY OF A HIGH PROFILE LAWYER

Upon realizing that he had a keen interest in law, he skipped continuing the engineering field and attended Vanderbilt University Law School on scholarship. In 1982, he graduated with a law degree.

The same year he graduated, Craig went to Stinson Mag & Fizzell. He was recruited by David Everson, who praised Craig’s confidence. In a year, Craig was given the opportunity of defending Hallmark Cards Inc. and other defendants in the Hyatt Skywalk Collapse. Craig had to defend his clients against a $1.5 million claim of post-traumatic stress disorder from the opposing party.  The trial gave Craig’s career the boost it needed, and he had successfully started paving his way to a thriving career.

1988 brought Craig to a law firm headquartered in St. Louis, Missouri, Bryan Cave Leighton Paisner, where he became a partner in 1990. Craig supported the non-profit organization that exonerates wrongfully convicted people, the Midwest Innocence Project, where he has been serving on the advisory board.

Mr. O’Dear’s accomplishments have been recognized in many publications. He was recognized by the Kansas City Business Journal as “Best of the Bar” in business and product liability litigation multiple times. He was also featured in the ‘Best Lawyers in America,’ Chambers USA, Missouri & Kansas Super Lawyer numerous times since 2006. Benchmark Litigation, named Craig, a ‘Missouri Litigation Star’ and the Lawdragon magazine named O’Dear, one of the Top 500 Leading Litigators in America in 2006.

In January 2018, Craig ran for Senate against Democrat incumbent Senator Claire McCaskill. He stood in the elections as an independent candidate, and a part of a Denver-based national movement of independents called Unite America and refused to caucus with either party if he would be elected. Even though O’Dear lost the election, he gained recognition by various notable personalities as an American politician because of his determination.

Today, Craig S. O’Dear lives with his family, his wife, Stephanie, in Kansas City. They have three children, daughter Sydney, and sons Cullen and Cormac.

The idea of Bigtime Daily landed this engineer cum journalist from a multi-national company to the digital avenue. Matthew brought life to this idea and rendered all that was necessary to create an interactive and attractive platform for the readers. Apart from managing the platform, he also contributes his expertise in business niche.

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Business

Derik Fay and the Quiet Rise of a Fintech Dynasty: How a Relentless Visionary is Redefining the Future of Payments

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Long before the headlines, before the Forbes features, and well before he became a respected fixture in boardrooms across the country, Derik Fay was a kid from Westerly, Rhode Island with little more than grit and audacity. Now, with a strategic footprint spanning more than 40 companies—including holdings in media, construction, real estate, pharma, fitness, and fintech—Fay’s influence is as diversified as it is deliberate. And his most recent move may be his boldest yet: the acquisition and co-ownership of Tycoon Payments, a fintech venture poised to disrupt an industry built on middlemen and outdated rules.

Where many entrepreneurs chase headlines, Fay chases legacy.

Rebuilding the Foundation of Fintech

In the saturated space of payment processors, Fay didn’t just want another transactional brand. He saw a broken system—one that labeled too many businesses as “high-risk,” denied them access, and overcharged them into silence. Tycoon Payments, under his stewardship, is rewriting that narrative from the ground up.

Instead of the all-too-common “fake processor” model, where companies act as brokers rather than actual underwriters, Tycoon Payments is being engineered to own the rails—integrating direct banking partnerships, custom risk modeling, and flexible support for underserved industries.

“Disruption isn’t about being loud,” Fay said in a private strategy session with advisors. “It’s about fixing what’s been ignored for too long. I don’t chase waves—I build the coastline.”

Quiet Power, Strategic Depth

Now 46 years old, Fay has evolved from scrappy gym owner to an empire builder, founding 3F Management as a private equity and venture vehicle to scale fast-growth businesses with staying power. His portfolio includes names like Bare Knuckle Fighting Championships, BIGG Pharma, Results Roofing, FayMs Films, and SalonPlex—but also dozens of companies that never make headlines. That’s by design.

Where others seek followers, Fay builds founders. Where most celebrate their exits, Fay reinvests in people.

While he often deflects conversations around his personal wealth, analysts estimate his net worth to exceed $100 million, with some placing it comfortably over $250 million, based on exits, real estate holdings, and the trajectory of his current ventures.

Yet unlike others in his tax bracket, Fay still answers cold DMs. He mentors rising entrepreneurs without cameras rolling. And he shows up—not just with capital, but with conviction.

A Mogul Grounded in Real Life

Outside of business, Fay remains committed to his role as a father and partner. He shares two daughters, Sophia Elena Fay and Isabella Roslyn Fay, and has been in a relationship with Shandra Phillips since 2021. He’s known for keeping his personal life private, but those close to him speak of a man who brings the same intention to parenting as he does to scaling multimillion-dollar ventures—focused, present, and consistent.

His physical stature—standing at 6′1″—matches his professional gravitas, but what’s more striking is his ability to operate with both discipline and empathy. Fay’s reputation among founders and CEOs is not just one of capital deployment, but emotional intelligence. As one partner noted, “He’s the kind of guy who will break down your pitch—and rebuild your belief in yourself in the same breath.”

The Tycoon Blueprint

The playbook Fay is writing at Tycoon Payments doesn’t just threaten incumbents—it reinvents the infrastructure. This isn’t another “fintech startup” with a flashy brand and no backend. It’s a strategically positioned venture with real underwriting power, cross-border ambitions, and a founder who understands how to scale quietly until the entire industry has to take notice.

In an age where so many entrepreneurs rely on noise and virality to build influence, Fay remains a master of what can only be called elite stealth. He doesn’t need the spotlight. But his impact casts a long shadow.

Conclusion: The Empire Expands

From Rhode Island beginnings to venture boardrooms, from gym owner to fintech force, Derik Fay continues to build not just businesses—but a blueprint. One rooted in resilience, innovation, and long-term infrastructure.

Tycoon Payments may be the latest chess piece. But the game he’s playing is bigger than one move. It’s a long game of strategic leverage, intentional legacy, and generational wealth.

And Fay is not just playing it. He’s redefining the rules.

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