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July 22, 2025 38 mins

Small business owner Jennifer Kok opened her cookie business and delivered her second daughter just two days later—literally delivering babies and cookies on the same day. After running her business for 20 years and experiencing everything from bounced paychecks to franchise success, Jennifer now helps overwhelmed entrepreneurs transform into confident CEOs without burning out on social media.

In this raw and honest conversation, Jennifer shares the real statistics behind small business failure (spoiler: they don't fail, they quit). She reveals the predictable pattern that causes entrepreneurs to walk away right before their breakthrough. From managing cash flow crises to building your personal board of directors, this episode pulls back the curtain on the messy middle of entrepreneurship. It provides actionable strategies for pushing through the plateau.

If you've ever felt isolated in your business, questioned whether you're cut out for entrepreneurship, or wondered how to pay yourself properly, this episode offers both practical solutions and the emotional support every business owner needs to hear.

What You'll Learn

  • Why 50% of small businesses actually quit rather than fail, and how to avoid becoming part of that statistic

  • The predictable pattern that hits entrepreneurs around year 3-4 and how to navigate "the messy middle"

  • How to build your personal board of directors with five specific types of advisors

  • The critical difference between working in your business versus working on your business

  • How to conduct a business breakthrough strategy, starting with your numbers

  • Why profit margins matter more than revenue and how to calculate what you're really earning

  • How to find your micro audience and unique differentiator without fear-based thinking

  • Cash flow management fundamentals that prevent payroll crises

  • The mindset shifts that separate successful entrepreneurs from those who quit

 

This episode features Jennifer Kok, a business coach with 25 years of entrepreneurial experience who literally delivered her baby and cookie orders on the same day she opened her business. Jennifer challenges the common belief that small businesses fail, arguing instead that they quit, particularly around the 3-4 year mark when entrepreneurs hit what she calls "the messy middle."

The conversation covers Jennifer's journey from corporate America to cookie business owner, including a humbling moment when she had to put payroll on a credit card during a family vacation. This crisis became a turning point that led her to master business fundamentals and eventually help other entrepreneurs avoid similar pitfalls.

Key insights include the importance of building a personal board of directors (comprising five specific types of advisors), understanding profit margins over vanity metrics such as revenue, and developing systems for working on your business rather than just in it. Jennifer emphasizes that entrepreneurial challenges aren't character flaws but navigation points toward better systems. That isolation kills more businesses than a bad strategy.

The episode explores the psychological aspects of entrepreneurship, highlighting the interconnection between personal and business growth, and provides practical strategies for financial management, targeting micro-audiences, and maintaining confidence during challenging periods.

Catch these additional episodes from the Game On Girlfriend® Podcast:

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