OA PRO
Specializing in Sports Professionals and Emerging Earners

David Osborne has had a profound impact in managing the financial lives of professional athletes. Recognizing that athletes face unique career arcs—often earning the majority of their lifetime income in a short period—Osborne helps them plan for both the spotlight and the years beyond. With the rise of Name, Image, and Likeness (NIL) deals, even student-athletes are now facing the financial complexities once reserved for professionals—making early guidance and strategic planning more essential than ever.

Welcome to OA PRO
Prepare Today for Life After Sports

Success on the field doesn't guarantee financial security off it. For professional and NIL athletes, understanding money is just as important as making it. Start now by saving aggressively, learning the financial basics, and staying actively involved in every money decision. The more you know today, the better prepared you'll be for the opportunities—and challenges—that come after your playing career ends.

OA PRO

Maximizing NIL Opportunities
with David Osborne and OA PRO

The world of sports and professional branding is evolving faster than ever, and David Osborne, Founder and CEO of On Alpha Capital, is at the forefront of this transformation. Through his family boutique wealth management firm, Osborne delivers a rare combination of strategic financial planning and real-world guidance for the emerging NIL (Name, Image, and Likeness) generation—student-athletes and professionals navigating opportunities that extend far beyond the playing field.

Mastering the NIL Landscape

The NCAA’s groundbreaking rule change in 2021 opened the door for student-athletes to profit from their name, image, and likeness, launching a multibillion-dollar market virtually overnight. From sponsorship deals and brand endorsements to social media monetization, NIL has created opportunities—and risks—that most young athletes are unprepared to manage. While these deals can provide life-changing income, they also introduce tax complexities, contract obligations, and the challenge of building sustainable wealth from what can be a short financial window.

David Osborne recognized early that this shift required more than traditional financial advising. Through OA PRO, a specialized service within On Alpha Capital, he helps student-athletes and young professionals maximize the benefits of NIL while safeguarding their future. His approach includes:

·       Wealth Structuring for Short Career Peaks: Professional and collegiate sports careers often generate the bulk of earnings before age 30. Osborne creates strategies to stretch that income well beyond an athlete’s active career, building long-term stability and generational wealth.

·       Tax & Compliance Management: NIL deals are often structured as self-employment income, leading to unexpected tax liabilities. OA Capital ensures that every deal is managed with proper tax planning to avoid costly surprises.

·       Investment in Future Security: Osborne integrates NIL earnings into diversified portfolios, including traditional investments, retirement accounts, and carefully evaluated alternative assets such as cryptocurrency and blockchain ventures.

·       Avoiding Sudden-Wealth Pitfalls: From impulse spending to predatory contracts, sudden income can be more dangerous than beneficial without proper guidance. Osborne educates clients on disciplined financial habits from the start.

 

From Locker Room to Boardroom

Osborne’s NIL advisory services don’t stop with student-athletes. His experience extends to entertainers, entrepreneurs, and business professionals who are building personal brands or entering endorsement opportunities. In today’s digital-first economy, social media influencers and young professionals are facing challenges similar to athletes: high-visibility income streams that require careful management to ensure sustainability.

Credentials That Inspire Confidence

With more than 25 years in wealth management and licenses spanning over 20 states, David Osborne brings unmatched expertise to the NIL space. His credentials include:

  • FINRA Series 7, 24, 31, 55, 63, and 65

  • General Securities Principal & Equity Trader

  • Group 1 Life & Health Insurance License

These qualifications, combined with decades of advising high-net-worth families and professional athletes, allow Osborne to navigate complex financial scenarios with precision.

A Philosophy Built on Education and Empowerment

David Osborne’s approach is rooted in financial literacy and family-first values. He believes that sustainable wealth starts with understanding—not just transactions. For student-athletes, this means learning how to save, invest, and plan for a life after sports. For professionals and entrepreneurs, it’s about leveraging personal brand opportunities without sacrificing long-term stability.

Every client journey at On Alpha Capital begins with a comprehensive evaluation of goals, income, and obligations. The result is a customized financial strategy designed to turn today’s NIL opportunities into tomorrow’s financial security.

Leading the NIL Generation to Financial Freedom

By combining advanced financial planning with a deep understanding of the modern sports and media landscape, David Osborne and OA Capital are setting a new standard for NIL wealth management. Whether you’re a student-athlete signing your first deal, a professional navigating sponsorships, or a brand-conscious entrepreneur, Osborne ensures that every opportunity is maximized—not just for the present, but for decades to come.