Two Paths.
One Standard.

Steven Tolleson's Story

Before entering wealth management in 2016, Steven Tolleson spent more than a decade competing at the highest levels of professional baseball.

After captaining the University of South Carolina baseball team in 2004 and 2005 and appearing in the College World Series in both 2003 and 2004, Steven was selected in the fifth round of the Major League Baseball Draft by the Minnesota Twins following his junior season.

He went on to play 12 seasons in professional baseball, including four years in Major League Baseball with three different organizations. Competing in elite environments, preparing daily to perform under pressure, and working alongside exceptional teammates shaped the principles that guide his work today: discipline, preparation, resilience, and leadership.

A Builder Serving Builders

Steven approaches wealth management the same way many of his clients approach business and life, as a builder. Like the entrepreneurs, executives, and high performers he serves, Steven believes in designing systems that perform at the highest level over long periods of time. WIN was created from that mindset.

For decades, many sophisticated wealth management capabilities were concentrated within family offices and large institutional platforms. Steven set out to build a firm that brings disciplined investment thinking and integrated planning to people building, managing, and transferring significant wealth.

At WIN, advanced tax strategy, investment management, and holistic financial planning are unified into a single wealth management system designed to simplify complexity and improve decision making. Modern technology and artificial intelligence are integrated into the firm's operating system to enhance clarity, accelerate insight, and allow the team to spend more time focused on high-trust client relationships.

Alignment With Clients

A foundational principle at WIN is alignment. Steven personally participates in the same investment strategies implemented for clients. The firm is designed so that clients are investing alongside a wealth management platform that is deeply committed to the same long-term outcomes.

Rather than simply managing portfolios, the firm focuses on optimizing complete financial stewardship, integrating investment strategy, tax planning, and long-term wealth architecture. As Founder, Steven leads the firm's investment strategy and focuses on building portfolios designed for the world that is emerging, helping clients navigate evolving markets, technological shifts, and economic change with confidence.

Life Outside the Office

Steven and his wife Baileigh, high school sweethearts, have been married for 17 years and are raising their three daughters, Claire, Sarah, and Caroline. Baileigh is a registered nurse who has served at Spartanburg Medical Center.

The Tolleson family is active in their community and are members of Anderson Mill Road Baptist Church in Spartanburg. Outside the office, Steven enjoys hunting, fishing, golf, and woodworking, pursuits that reflect the same patience, craftsmanship, and appreciation for building things that last.

Anthony Mahfood's Story

Anthony Mahfood brings more than 25 years of institutional wealth advisory experience to WIN, having spent his career serving ultra-high-net-worth individuals, families, and business owners navigating the complexities of generational wealth transfer and sophisticated financial planning.

Early in his career, Anthony worked with Capital Planners and BB&T Wealth Management, where he earned three Royal Flush Awards and two Sterling Performer Awards while advising affluent families and business owners. He later co-founded Parallel Financial, LLC, further developing his integrated approach to wealth advisory.

Anthony co-founded WIN to serve clients with complex financial lives through a highly personal and coordinated approach to wealth management. He is known for simplifying complexity and providing clear, decisive guidance on liquidity events, concentrated positions, and generational wealth transfer.

His approach emphasizes alignment, discretion, and long-term stewardship, enabling clients to make confident decisions. At WIN, Anthony oversees comprehensive wealth strategy, integration of advanced tax planning, and holistic financial architecture.

Institutional Wisdom, Personal Touch

Anthony's work integrates investment strategy, liquidity planning, business succession, estate structuring, and risk management into a cohesive approach designed to preserve and grow multigenerational wealth.

WIN operates proactively, delivering differentiated ideas and forward-looking strategies tailored to each client's evolving needs. By combining institutional-level insight with deep personal alignment, the firm provides cutting-edge solutions to navigate complexity and capitalize on opportunity.

Family & Community

Anthony earned his undergraduate degree from John Carroll University and his MBA from the University of Tennessee.

He and his wife, Tracy, live in Greenville with their two daughters, Sophia and Lydia. Anthony is an active member of St. George Greek Orthodox Cathedral and Young Presidents' Organization. Outside of work, he enjoys spending time with family, supporting his daughters' athletic pursuits, and time on the golf course or fishing with family and friends.