Advertise on podcast: Small Business Big Deal Podcast

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. 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.

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

From Dog Training to Franchising: How Passion Turned into 24 Locations with Ryan Wimpey In this episode of Small Business Big Deal, I sit down with Ryan Wimpey, founder of Tip Top K9 Dog Training, to talk about how one stubborn rescue pup led him down the path of building one of the fastest-growing dog training franchises in the U.S. Ryan shares how he went from training dogs behind a Chick-fil-A to running a business with 24 locations, a national call center, and a fully systemized franchise model. We dive into: The painful personal story that sparked his obsession with dog training How passion, persistence, and working for free in the early days helped him break into the industry Why systems—not just skills—are the backbone of scalable businesses The shift from working in the business to leading it as CEO Lessons learned about franchising, culture, and consistency across locations How investing in coaches and consultants has fast-tracked his growth What makes Tip Top K9's training methodology unique (hint: Pavlov would approve) The rewarding impact of helping not just dogs and their owners, but also new entrepreneurs and franchisees   This conversation is packed with practical advice for any business owner who wants to scale, step into the CEO role, and build a company that lasts beyond themselves.   📍 Learn more about Ryan and Tip Top K9: TipTopK9.com 📍 Connect with Ryan on LinkedIn: Ryan Wimpey

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. 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

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.   00:00The Birth of Golf Angels 05:22Overcoming Startup Challenges 11:26A Day in the Life of an Entrepreneur 19:22Breaking Traditions in Golf 25:57Celebrating Small Wins in Entrepreneurship 31:43Advice for Aspiring Entrepreneurs in Niche Markets   Connect! Website: golfangelshop.com IG : @golf_angel_shop

💡 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

Jess Freeman, the owner of Jess Creatives, specializes in high impact websites and SEO for business owners. She helps them improve their branding, websites, and SEO to generate more leads and traffic. Jess explains that she was drawn to SEO because she saw many business owners struggling with social media and not getting results from their websites. She combines her creative and analytical skills to help clients improve their online presence. Jess also shares her journey as a business owner, including the importance of setting boundaries and finding a balance between client work and working on her business. In this conversation, Jess and Tracy discuss the importance of Pinterest and SEO in business marketing strategies. They highlight the benefits of using Pinterest as a search engine and the potential for businesses to reach their target audience through the platform. They also discuss the significance of staying updated on SEO trends and offer tips on how to do so. The conversation concludes with advice for entrepreneurs, emphasizing the importance of pivoting and staying consistent in business. KEYWORDS: websites, SEO, branding, social media, business owner, boundaries, client work, working on the business, Pinterest, SEO, business marketing, search engine, target audience, staying updated, pivoting, consistency 00:00 Introduction and Background   02:49 The Importance of Websites and SEO   08:51 Transitioning to Full-Time Business Owner   11:52  Setting Boundaries and Managing Clients   19:58 Balancing Client Work and Working on the Business   32:01 Effective Marketing Channels: Instagram, Threads, and YouTube   35:04 The Value of Pinterest for Business Owners   35:25 Harnessing the Power of Pinterest   38:02 Staying Updated on SEO Trends   43:36 The Importance of Pivoting in Business   45:28 The Power of Consistency   49:18 Understanding Your Clients and Their Platform Usage   52:06 Using Data and Analytics to Inform Content Creation   53:46 Investing in Education and Seeking Guidance   55:02 Building a Strong Online Presence   57:21 Adapting to Changes in Algorithms   58:36 The Benefits of Having a Website with Optimized SEO   01:00:36  Overcoming Challenges and Achieving Success

On today's podcast, we're talking with Katie Dooley, owner of Paper Lime Creative, a branding and design agency in Edmonton, AB. Her company creates stunning visual branding that shows off businesses' unique personalities. Their print design services make getting a brand out into the world effortless and enjoyable.   Read more: https://tracyjepsonpodcast.com/media/ep-39-design-agency-owner-helps-businesses-create-stunning-branding/1490/    About our guest: https://paperlime.ca/about/    What we discuss on this episode:  0:56 – Meet Katie 1:29 – Entrepreneur dreams 3:45 – Making the transition 7:25 – Changing her life 10:00 – Growing pains 11:03 – Structuring her business 12:09 – Brand strategy 16:02 – Companies she works with 17:32 – Growth 18:47 – Continuing education 21:26 – Managing the work 26:11 – When to hire a marketing company 36:40 – Advice

On today's podcast, we're talking with Dennis Crosby, owner of Crochet Media Group, an online subscription that focuses on the arts and crafts niche, especially crocheting. Find out how his business is thriving, even during COVID.   Read more: https://tracyjepsonpodcast.com/media/ep-38-online-magazine-business-booming-even-during-covid/1484/    About our guest: https://denniscrosby.com/    What we discuss on this episode:  1:32 – Meet Dennis 12:55 – How he ended up working on a magazine 19:53 – Why he continued magazine 24:45 – Building teams 29:06 – Hiring 34:16 – Personal development 40:59 – What's next

On today's podcast, we're talking with J.B. Morris, founder of Concierge Wealth Management based in Boston. Find out how he helps high earners in their 30s and 40s develop financial plans.   Read more here: https://tracyjepsonpodcast.com/podcast/ep-37-concierge-wealth-owner-helps-clients-achieve-financial-goals/1475/    About our guest: https://www.conciergewm.com/team/julian-morris    What we discuss on this episode:  1:19 – Meet J.B. 2:19 – Becoming a financial advisor 3:28 – The financial industry 7:30 – Owning a business 13:20 – Work-life balance 18:04 – In person versus virtual 24:00 – Financial planning 33:38 – Mental toughness 38:58 – Advice 40:38 – Contact J.B.

On today's podcast, we're talking with Todd Bertsch, owner of Evolve Marketing and a leader in the web design industry. Find out how this self-described "true-born leader" created his company. Read more:  https://tracyjepsonpodcast.com/podcast/ep-36-how-a-true-born-leader-created-his-own-marketing-team/1468/ About our guest:  Todd is an award-winning web designer, author, educator, and lecturer, and speaks regularly throughout the region on various web-related topics. He holds a BFA from The University of Akron in graphic design. His web experience and marketing strategies are what separate him and Evolve from others in the web industry. Helpful Resources: https://www.evolvemarketingteam.com/ https://www.linkedin.com/in/toddmbertsch/ What we discuss on this episode:  1:29 – Meet Todd 3:29 – Why entrepreneurship 7:34 – Work-life balance 17:54 – Delegation 20:29 – First hire 25:38 – Accounting 29:08 – What he wishes he knew 33:01 – Failure 33:36 – How his business is different 39:33 – Advice for new business owners 42:05 – Contact Todd

On today's podcast, we're talking with Laura Wright, a master sales coach who is helping "badass business women" make more money and know their worth.   Read more: https://tracyjepsonpodcast.com/entrepreneur/ep-35-sales-ninja-helps-badass-business-women-know-their-worth/1463/    About our guest:  Laura Wright is a Self-Published Author, Speaker, Growth Strategist, Master Sales Coach and co-founder of The Sould Sisters.  She has closed a cool $43 million and then some over the past 20 years and she's the founder of EPIC at Sales, but, for a time Laura Wright's life was anything but epic.  After her real estate company crashed and burned in 2008, Laura found herself over $500,0000 in debt and doubting her ability to rise up from this setback, until she remembered two of her greatest gifts: the power to see the potential in ANY situation and the ability to close just about any sale with love.  A few years later, Laura has made a name for herself in the coaching industry as the go-to "Sales Ninja" for service-based women in business, helping her clients scale to six-figures within months and cross seven-figures in record time.   Join her Facebook Group: https://www.facebook.com/groups/thesouldsisters    What we discuss on this episode:  1:05 – Meet Laura 4:19 – Don't give discounts 5:40 – How she became a business owner 8:06 – College burnout 14:53 – Building a business plan 27:05 – Hire before you're ready 31:42 – Getting your spouse on board 35:48 – New businesses and knowing your worth 43:26 – Bringing on a partner 50:36 – The Sold Sisters