What’s the one mistake that can quietly rob you of fulfillment in both business and life? For Winston Justice, CEO of SageSpring, it’s failing to be present.

In this episode, host Kelly Waltrich sits down with Winston to unpack his extraordinary journey - from protecting quarterbacks in the NFL to leading a $7.8B wealth management firm. Along the way, Winston shares how lessons from football, entrepreneurship, and finance shaped his leadership philosophy, and why accountability, resilience, and adaptability matter just as much in the boardroom as they do on the field.

He also reveals the sacred responsibility advisors hold in stewarding not only wealth but also values, legacy, and family well-being — and why the best advisors of tomorrow will blend technical acumen with deep relational skills.

Winston’s Don’t Do That advice? Don’t miss the moment. Success often comes from focusing on what’s right in front of you instead of constantly chasing what’s next.

This conversation is packed with insights on leadership, transitions, family, and finding meaning in the work we do every day.

Kelly and Winston cover:
00:00 – Winston’s introduction and overview of SageSpring
01:16 – From USC to the NFL: early lessons in growth and resilience
03:12 – Starting Elixir Coffee and the first taste of entrepreneurship
04:41 – Transitioning out of football: fear, reinvention, and Wells Fargo
05:48 – Lessons from Bernstein and leading nonprofit/foundation clients
06:16 – Becoming CEO of SageSpring and why stewardship matters
07:23 – Three leadership lessons from sports: failure, accountability, and teamwork
10:08 – Why Winston now follows coaches more than NFL players
11:14 – What sets SageSpring apart: legacy, values, and sacred client relationships
13:18 – The evolving role of advisors: beyond portfolios to purpose and well-being
15:32 – Sports dreams, parenting, and preparing kids for life beyond athletics
16:44 – Winston’s “Don’t Do That”: Don’t miss the moment — be present
19:17 – How being present changes leadership, family, and perspective
21:42 – Practical advice for choosing presence daily

Winston Justice is CEO of SageSpring Wealth Partners, a fiduciary firm managing more than $7.8B in client assets across 11 offices in 5 states. A former NFL offensive lineman who played for the Eagles, Colts, and Broncos, Winston has successfully transitioned from pro sports to entrepreneurship and finance, building a career defined by resilience, accountability, and servant leadership.

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