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.

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.

🌐 Website: 35x70golfco.com

📱 Instagram & Facebook: @35x70GolfCo

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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

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

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.

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

When your identity is tied to a title and that title gets stripped away, what's left?

In this episode, Tracy sits down with Jeremy Capo—a respected collegiate athletics administrator turned business development executive and all-around motivational force. From navigating career upheaval during the pandemic to finding his footing through faith, fitness, and a relentless commitment to showing up, Jeremy's story is a masterclass in resilience, reinvention, and remembering your why.

Chapters

00:00 Introduction and Motivation
02:50 The Journey of Consistency
06:06 Impact on Family and Personal Life
08:57 Personal Habits for Success
11:47 Navigating Change and Patience
14:50 Overcoming Imposter Syndrome
17:57 Building Relationships and Connections
21:06 Legacy and Impact
24:01 Finding Motivation and Starting Small
39:48 Listening to Your Body: The Importance of Rest
41:53 Dinner with Influential Figures: Personal Reflections
44:03 Conversations with Our Younger Selves: Lessons Learned
47:00 The Value of Resilience: Learning from Low Points
50:07 Celebrating Wins: The Importance of Self-Acknowledgment
54:04 Transformative Moments: The Journey to Change

In this conversation, Tracy Jepson interviews Sabrina, the founder of Golf Angels, a brand aimed at making golf more accessible and relatable for women. They discuss the inspiration behind the brand, the challenges of starting a business, the importance of self-care, and how Golf Angels aims to break traditional norms in the golf industry. Sabrina shares her journey as an entrepreneur, the support she receives from her community, and her vision for creating a brand that resonates with women golfers. In this conversation, Sabrina and Tracy discuss the evolution of women's golf apparel, the importance of celebrating small wins in entrepreneurship, and the challenges of building a niche brand in a traditionally male-dominated industry. They emphasize the need for modern branding that resonates with younger generations and the significance of community engagement in growing a business.

💡 Episode Summary:

What happens when you realize success isn't just about the numbers, the status, or the accolades? In this episode, I sit down with Sydney Ryker, an entrepreneur, speaker, and mentor who took the leap from high-performing network marketer and business owner to a journey of deep self-discovery. Sydney shares her incredible story—how she started her entrepreneurial journey with $50 and no plan, built multiple businesses, and then walked away from it all to find true alignment.

We dive into:

✅ The real story behind her move to California with nothing but resourcefulness

✅ Why women in business struggle with valuing their own worth—and how to change that

✅ The pressure to scale, build big, and 'be a powerhouse' vs. defining success on your own terms

✅ How removing societal expectations, alcohol, and external validation led to her most fulfilling life yet

✅ The importance of choosing clients, stages, and opportunities that align with your values

✅ Why success isn't just about chasing money, but about waking up at peace

This episode is a must-listen for anyone who's ever felt the weight of external expectations, struggled with pricing their worth, or wondered if they're on the right path. Sydney's journey is raw, honest, and inspiring—proving that sometimes, the biggest transformation comes from stripping away rather than adding more.

📚 Books Mentioned:

• The Queen's Code by Alison Armstrong

• Secrets of the Millionaire Mind by T. Harv Eker

• A Court of Thorns and Roses series by Sarah J. Maas

📍 Where to Find Sydney:

🌐 Website: sydneyryker.com

📸 Instagram: @sydneyryker

📹 TikTok: @sydneyryker

📖 Preorder Her Book: Available on her website!

Chapters

00:00 Introduction and Early Entrepreneurial Journey
02:25 Meeting a Mentor and Transitioning to Speaking and Writing
09:37 The Benefits and Challenges of Network Marketing
12:18 Finding Joy and Enjoyment in Business
19:16 Creating Minimal and Flexible Systems in Business
25:26 Defining Success on Your Own Terms
29:47 Embracing Authenticity and Personal Growth
31:31 The Journey of Self-Discovery
36:00 Aligning Values for Success
39:09 Sharing the Secrets of Entrepreneurship
42:26 Embracing the Process, Letting Go of Perfectionism
44:42 Cultivating a Healthy Money Mindset
48:26 Grounding and Recharging for Well-Being