Ep. 49 Integrity, Curiosity, and the Long Game with Elliott Orsillo

This week on Small Business Big Deal, Tracy sits down with Elliott Orsillo, co-founder of Season Investments, to explore what it really means to build a business rooted in integrity, curiosity, and long-term thinking.

Elliott's journey from engineering at Stanford to leading a wealth management firm is filled with valuable lessons about resilience, partnership, and trust. He shares how a foundation in problem-solving and risk analysis shaped his approach to investing — and how staying curious has kept his business innovating and his clients grounded through market volatility.

In this episode, Tracy and Elliott talk candidly about:

• The evolution from corporate life to entrepreneurship — and why he traded a Fortune 500 career for building something of his own.

• What curiosity looks like in practice and how it drives better decision-making and business growth.

• The toughest season of his entrepreneurial journey: uncovering client fraud, rebuilding trust, and repaying investors out of sheer integrity.

• The importance of mutual respect in partnerships and why theirs has lasted more than 14 years.

• How parenting three teenage daughters has shaped his leadership style and emotional intelligence.

• Why maintaining balance isn't about working less — it's about knowing what really matters.

• His take on AI's growing role in wealth management and why human connection will always matter more than automation.

Elliott also shares his favorite outdoor escape in Colorado, the two books that changed how he views control (The Untethered Soul and Letting Go), and even his hidden talent that drives his daughters crazy.

If you've ever wondered how curiosity fuels clarity — and what it takes to keep showing up when business gets hard — this episode is your reminder that integrity and adaptability win the long game.