The Long Game

Longplay
  • 0.0 (0)
  • Entrepreneurship

The Long Game is an honest conversation about building businesses that last. Hosted by Jess Chan and Rachyl Neidecker of Longplay, the podcast explores the realities of entrepreneurship, leadership, and long-term growth through the lens of two partners who have spent years building businesses alongside founders and executive teams. Rather than chasing trends or quick wins, each episode unpacks the deeper questions behind building something meaningful: How do you scale without losing your foundations? How do you navigate change while staying true to your vision? And how do you build a business that not only grows—but continues to feel worth building? Through thoughtful conversations, lived experience, and reflections from years of working with hundreds of businesses, The Long Game offers a quieter perspective on entrepreneurship—one rooted in resilience, partnership, and the belief that lasting success is built one thoughtful decision at a time.

Episodes

  1. Sep 8

    #3: Why Execs & Founders Get Stuck In The Weeds (And How To Get Out)

    Rachyl & Jess dive into challenges faced by one of the biggest challenges founders & executives have: getting stuck in the weeds. They take an honest look at the (often invisible) impact of being pulled into day-to-day operations, and how it pulls execs away from strategic planning. They introduce Longplay's Hierarchy of Strategy framework which is a tool to help founders & execs diagnose how they're spending their time, find systemic issues & make a plan to delegate. Through this conversation, they reflect the art of leadership, delegation, and the permission to seek help. Chapters 00:00 Introduction and Podcast Kickoff00:30 The Experience of Executives in E-commerce Brands02:57 Challenges Faced by Executives06:00 Hierarchy of Strategy Framework11:13 The Art of Leadership and Delegation16:07 Permission to Let Go and Seek Help22:46 Identifying Systemic Issues and Solutions29:07 Reflection and Practice of Hierarchy of Strategy

  2. Sep 8

    #2: Preparing For Q4

    Jess & Rachyl dive into the 3 core aspects of planning for profitable Q4 that sets e-commerce businesses up for long-term scalable success: 1. Infrastructure (finances, cash flow, inventory, operations) 2. Humanization (value prop, positioning, customer experience) 3. Q1 & Beyond (retention, subscription, loyalty) They explore the importance of understanding the state of the industry, market, and consumer behavior, as well as the need to plan ahead for inventory, pricing, and unboxing experiences. Additionally, they touch on the significance of thinking past Q4 to turn this peak period into a successful next year. Chapters 00:00 The Importance of Q4 Planning03:12 Humanization and Brand Experience06:03 Infrastructure and Operations08:50 Long-term Planning and Retention

  3. Sep 8

    #1: How To Play The Long Game In Business

    This honest, open conversation delves into what it takes to build a business that is scalable, sustainable & profitable in the long run. Rachyl & Jess share what it's really like behind-the-scenes in a business covering: the evolution of Longplay over the last 7+ yearsthe balance between authenticity and strategy in businessthe challenges and rewards of staying true to the vision while adapting to the changing landscape of businessthe journey of entrepreneurship, the pitfalls of rushing growth, the irony of fundraising, the misalignment of pacing and vision, and the impact of rushing growththe pressure of rapid scaling, the ugly side of business, the rewiring of business thinking, and the concept of quality over quantitythe inside-out approach to business, the radiating impact of business decisions, the journey to solid foundations Takeaways Authenticity and strategy must be balanced in business for sustainable growth.The evolution of a business requires letting go of 'shoulds' and embracing the journey with patience and joy. The journey of entrepreneurship is filled with challenges and requires a flexible and adaptive approach.Rushing growth and scaling can lead to significant pitfalls and long-term consequences for a business. Chapters 00:00 The Journey of Authenticity11:28 Balancing Authenticity and Strategy in Business20:42 The Evolution of Long Play29:13 The Journey of Entrepreneurship31:23 The Pitfalls of Rushing Growth32:35 The Irony of Fundraising33:40 The Misalignment of Pacing and Vision35:29 The Impact of Rushing Growth36:21 The Pressure of Rapid Scaling38:04 The Ugly Side of Business40:59 The Rewiring of Business Thinking43:00 Quality Over Quantity47:00 The Inside-Out Approach to Business56:43 The Radiating Impact of Business Decisions59:31 The Journey to Solid Foundations01:11:37 The Sniff Test for Business Problems

  • 3 Episodes

About

The Long Game is an honest conversation about building businesses that last. Hosted by Jess Chan and Rachyl Neidecker of Longplay, the podcast explores the realities of entrepreneurship, leadership, and long-term growth through the lens of two partners who have spent years building businesses alongside founders and executive teams. Rather than chasing trends or quick wins, each episode unpacks the deeper questions behind building something meaningful: How do you scale without losing your foundations? How do you navigate change while staying true to your vision? And how do you build a business that not only grows—but continues to feel worth building? Through thoughtful conversations, lived experience, and reflections from years of working with hundreds of businesses, The Long Game offers a quieter perspective on entrepreneurship—one rooted in resilience, partnership, and the belief that lasting success is built one thoughtful decision at a time.

Information

  • Creator
    Longplay
  • Years Active
    2026
  • Episodes
    3
  • Rating
    Clean
  • Copyright
    © 2026 Longplay
  • Show Website
    The Long Game