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.
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Ep. 48 From Fairways to Fashion: The 35x70 Golf Co. Story
What happens when a late-night conversation about polos turns into a thriving golf apparel brand? In this episode of Small Business, Big Deal, Tracy sits down with Katy Winters, co-founder of 35x70 Golf Co., a Kansas-born company that's redefining golf style with a Midwestern twist. Katy shares the inspiring story of leaving a stable corporate career at Koch Industries to pursue entrepreneurship alongside her husband, Dan, a lifelong golf pro. Together, they've created a line of polos, hoodies, and accessories that blend classic design with Midwest-inspired patterns like wheat stalks and corn cobs—far from the palm trees and martinis of traditional golf wear. In this conversation, Tracy and Katy cover: The origin of the name 35x70 and why it resonates with golf and Midwest roots The challenges (and surprises) of launching an apparel brand without a fashion background How Katy's finance and accounting expertise became the backbone of their business operations The dynamics of building a company with your spouse—and how to balance marriage with entrepreneurship Why listening to customer feedback has been crucial for growth and product development The leap from side hustle to full-time business, and the faith required to keep moving forward Exciting news: women's polos and quarter zips are launching soon Katy also opens up about the emotional side of entrepreneurship—leaving corporate "security," pushing through imposter syndrome, and finding the grit to build something that reflects both family values and community pride. Whether you're a golfer, an entrepreneur, or someone who loves stories of bold career pivots, this episode will leave you inspired to chase what's possible. 🎧 Tune in to hear how Katy and Dan are bringing Midwest flavor to fairways across the U.S.—from Kansas to Alaska and beyond. Connect with 35x70 Golf Co. 🌐 Website: 35x70golfco.com 📱 Instagram & Facebook: @35x70GolfCo Want to level up your business strategy? Subscribe to Small Business, Big Deal and never miss an episode filled with real stories, actionable insights, and entrepreneurial grit.
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Ep. 47 Building a Business That Honors Your Values
Most entrepreneurs can rattle off their revenue goals or marketing plan without hesitation. But ask them what they stand for — what they refuse to compromise on — and the silence is deafening. In this solo episode of Small Business Big Deal, Tracy pulls back the curtain on the one thing that makes or breaks your business: your values. Far from being fluffy buzzwords, your values shape who you hire, how you market, what clients you accept, and how you lead your team. You'll hear real stories from Tracy's own journey (including how ignoring her value of simplicity nearly derailed her business and family) and from clients who discovered that being out of alignment with their values was the source of their frustration, burnout, and resentment. By the end of this episode, you'll walk away with: A step-by-step process to uncover your top five values. Reflection questions that reveal what truly drives you. A framework for aligning your business decisions with your values. Practical ways to use values as a compass for growth, boundaries, and joy in your work. Your business doesn't have to drain you — it can (and should) reflect who you are at your core. This episode will help you make sure it does. ✨ Free Resource: Take the Values Assessment to uncover your top five values and put this exercise into action right away
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Ep. 45: Building Bold Businesses Without Losing Yourself with Jac White
In this conversation, Tracy Jepson and Jac White explore the realities of entrepreneurship, particularly for women. They discuss the challenges of starting a business, the importance of sales strategies, and the need for flexibility in client relationships. Jac shares her insights on overcoming sales anxiety, understanding financial needs, and the significance of building relationships for sales success. They also touch on the concept of good versus bad money and the process of pivoting in business. In this conversation, Jac White and Tracy Jepson discuss the challenges and excitement of building businesses that empower women, the importance of balancing personal and professional life, and the need for integrity in business relationships. They explore the evolving landscape of entrepreneurship, the significance of understanding customer needs, and the value of saying no to maintain focus and integrity. The discussion emphasizes the importance of personal growth, learning, and building a supportive community for women entrepreneurs. Chapters 00:00 Introduction to Entrepreneurship and Sales 03:00 The Reality of Starting a Business 06:08 Navigating Client Relationships and Expectations 08:58 The Importance of Flexibility in Business 12:01 Overcoming Sales Anxiety and Pricing Challenges 15:00 Building Relationships for Sales Success 17:48 Understanding Financial Needs in Business 20:55 The Value of Good Money vs. Bad Money 23:55 The Process of Pivoting in Business 27:51 Passion for Women and Money 29:12 Building a Business: The Challenges of Growth 30:56 Balancing Personal and Professional Life 36:41 Navigating the Noise: Selecting Growth Opportunities 41:20 Understanding Customer Needs in a Noisy Market 48:37 Integrity in Business: Building Trust and Relationships
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Ep: 44 Creating a World of Wonder
In this episode of the Small Business Big Deal podcast, host Tracy Jepson interviews Roxanne Alford, the founder of Short Stuff, a sustainable children's clothing brand inspired by her experiences as a new mom. Roxanne shares her journey from working in IT sales to launching her own brand, driven by a desire for gender-neutral clothing and educational products for children. The conversation explores the challenges of entrepreneurship, including sourcing sustainable materials, balancing personal life with business, and the importance of community feedback. Roxanne emphasizes the significance of resilience, personal growth, and breaking stereotypes in the fashion industry. In this engaging conversation, Roxanne Alford shares her journey as an entrepreneur, discussing her unique skills, the launch of her new collection, and the importance of support systems for women in business. She emphasizes the significance of pursuing one's passions, balancing motherhood with entrepreneurship, and the value of community among women. Roxanne also reflects on her aspirations for her business and the legacy she hopes to create. Website: https://shortstuffshop.com/ Instagram: https://www.instagram.com/shortstuff.shop/ Code to Shop: SHORTSTUFF30 Chapters 00:00 Introduction to Roxanne Alford and Short Stuff 03:33 The Journey to Entrepreneurship 05:54 Sourcing Suppliers and Sustainability 08:07 Balancing Personal Life and Business 10:33 Financing the Startup 11:39 Risks in Entrepreneurship 14:22 Personal and Professional Growth 16:43 Inspirations and Resilience 18:34 Learning from Experience 20:18 Creating a Sense of Home 21:54 Feedback and Community Engagement 23:27 Gender Neutrality in Children's Clothing 25:08 Fun and Useless Skills 25:54 Useless Skills and Hidden Talents 27:21 The World of Wonder Collection 30:08 Lunch with Influential Figures 32:08 Building a Legacy through Business 35:43 Encouragement for Aspiring Entrepreneurs 39:07 Balancing Motherhood and Entrepreneurship 42:13 Where to Find Short Stuff Shop
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.
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