More Than Money Episode 2: Leading with Authenticity: Leadership and the Future of Work

Leading with Authenticity: Leadership and the Future of Work

Host Jake Cuthbert of Educo Advisor Group welcomes Stephanie Masters (Nonprofit Sidekick) for a candid conversation on leading with authenticity, building healthy culture, and navigating the future of work—from higher ed and nonprofits to corporate life and entrepreneurship.

From art teacher to HR leader to executive coach, Stephanie’s journey shows that great leadership isn’t about titles—it’s about clarity, candor, and caring enough to have the hard conversations.You’ll learn:🧭 Authentic Leadership: How to be real (not performative) while setting clear expectations.

• 🤝 Culture over Policy: Why misalignment between boards, execs, and teams breeds dysfunction—and how to fix it.
• 🏢 Hybrid & RTO Reality: Why many top performers resist the office—and how leaders can keep them visible and growing.
• 🗣️ Radical Candor 101: Caring personally and challenging directly; avoiding ruinous empathy and obnoxious aggression.
• 🧠 Strengths Tools: Where CliftonStrengths, Predictive Index, and Kolbe each shine—and how to use them together.
• 🚀 Accidental Business Owners: Start with why, know your gaps, and find a “who” (coach/partner) instead of forcing every “how.”

“Move from being nice to being kind. Kindness tells the truth because it cares.”

— Stephanie Masters

If you’re a founder, people leader, or anyone building teams with purpose, this episode delivers practical frameworks and real-world examples you can use today.

Listen now on YouTube or your favorite podcast platform.

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Securities and advisory services offered through LPL Financial, a Registered Investment Advisor. Member FINRA/SIPC. This content is for educational purposes only and not personalized financial advice.

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Jake Cuthbert, CFP®, AIF®

Jake Cuthbert is President of Educo Advisor Group and an LPL Financial Advisor with nearly two decades of experience helping individuals, families, and business owners make informed financial decisions. He earned his B.S. in Finance from Grove City College in 2004 and became a CERTIFIED FINANCIAL PLANNER™ professional in 2016.

Jake’s expertise includes retirement income strategies, tax planning, wealth transfer, succession planning, cash flow management, investments, college savings, risk management, and estate planning. His approach reflects Educo Advisor Group’s mission to Educate, Communicate, and Guide through personalized, practical financial strategies.

Jake also serves as President of the Financial Planning Association of Pittsburgh and as a part-time instructor for Duquesne University’s Certificate in Financial Planning program.

Latest posts by Jake Cuthbert, CFP®, AIF® (see all)

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