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Small Business Big Deal PodcastAuthor: Tracy Jepson
Welcome to the Small Business, Big Deal Podcast, where entrepreneurs from all walks of life deconstruct their businesses, sharing the journey of how they built their success, piece by piece. Our mission is to inspire and empower budding entrepreneurs to turn their dreams into thriving businesses. Each week, we spotlight the brightest minds in entrepreneurship, both current and future stars, offering invaluable insights and lessons learned. Hosted by Tracy Jepson, a seasoned Small Business Strategist, Certified Mastery Profit First Professional, and CEO of Jepson Solutions, LLC, this podcast delves deep into the world of small business. With over 25 years of experience in small business administration, Tracy has a profound understanding of the unique challenges companies face, especially in those critical first five years. Tracy's expertise lies in helping clients decipher their financial numbers to understand how they impact the overall health of their business. She crafts strategic plans based on industry best practices to support growth goals and provides ongoing monthly support to ensure her clients achieve those goals and ultimately get out of debt. Through her one-on-one coaching and mastermind programs, Tracy shares her wealth of knowledge with everyday entrepreneurs and start-up business owners. These coaching services provide entrepreneurs with the guidance and support they need to create profit-focused foundations, manage their cash flow effectively, eliminate debt, and build sustainable businesses. Tune in to the Small Business, Big Deal Podcast and join us on a journey of entrepreneurial discovery and growth. One business owner. One story. Week by week. Language: en Genres: Business, Entrepreneurship, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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Ep. 49 Integrity, Curiosity, and the Long Game with Elliott Orsillo
Episode 49
Thursday, 16 October, 2025
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.
