Small Business Big Deal Podcast

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 pl

Small Business Big Deal Podcast is a business podcast hosted by Tracy Jepson, with 50 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Tracy Jepson hosts Small Business Big Deal Podcast, a business show with 50 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #49

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

  Oct 16, 202555 minS0

  <p >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.</p> <p >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.</p> <p >In this episode, Tracy and Elliott talk candi...

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  Episode #48

  Ep. 48 From Fairways to Fashion: The 35x70 Golf Co. Story

  Sep 24, 202552 minS0

  <p >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.</p> <p >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 pa...

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  Episode #47

  Ep. 47 Building a Business That Honors Your Values

  Sep 17, 202512 minS0

  <p >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.</p> <p >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.</p> <p >You’ll hear real stories from Tracy’s own journey (including how ignoring her value of...

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  Episode #46

  Ep. 46 - Dog Training, Systems, and Scaling with Ryan Wimpey

  Aug 19, 20251 minS0

  <p >From Dog Training to Franchising: How Passion Turned into 24 Locations with Ryan Wimpey</p> <p >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.</p> <p >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:</p> <p >The painful personal...

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  Episode #45

  Ep. 45: Building Bold Businesses Without Losing Yourself with Jac White

  Apr 18, 202556 minS0

  <p>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...

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