<![CDATA[The Long Game]]>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.

]]>www.longplaybrands.comRiverside.fm (https://riverside.com)Fri, 16 Oct 2026 20:38:13 GMTTue, 07 Jul 2026 21:20:33 GMT60Longplay<p><b>The Long Game is an honest conversation about building businesses that last.</b></p><p>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.<br /></p><p>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?<br /></p><p>Through thoughtful conversations, lived experience, and reflections from years of working with hundreds of businesses, <i>The Long Game</i> 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.</p>episodicLongplayjess@longplaybrands.comno<![CDATA[#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 Kickoff
  • 00:30 The Experience of Executives in E-commerce Brands
  • 02:57 Challenges Faced by Executives
  • 06:00 Hierarchy of Strategy Framework
  • 11:13 The Art of Leadership and Delegation
  • 16:07 Permission to Let Go and Seek Help
  • 22:46 Identifying Systemic Issues and Solutions
  • 29:07 Reflection and Practice of Hierarchy of Strategy
]]>626161f3-fd52-4688-9c8c-1a21a5168292Tue, 08 Sep 2026 19:47:45 GMT<p>Rachyl &amp; Jess dive into challenges faced by one of the biggest challenges founders &amp; executives have: getting stuck in the weeds. <br /><br />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 &amp; execs diagnose how they're spending their time, find systemic issues &amp; make a plan to delegate.<br /><br />Through this conversation, they reflect the art of leadership, delegation, and the permission to seek help. </p><p></p><p>Chapters</p><ul><li>00:00 Introduction and Podcast Kickoff</li><li>00:30 The Experience of Executives in E-commerce Brands</li><li>02:57 Challenges Faced by Executives</li><li>06:00 Hierarchy of Strategy Framework</li><li>11:13 The Art of Leadership and Delegation</li><li>16:07 Permission to Let Go and Seek Help</li><li>22:46 Identifying Systemic Issues and Solutions</li><li>29:07 Reflection and Practice of Hierarchy of Strategy</li></ul>no00:33:4713#3: Why Execs & Founders Get Stuck In The Weeds (And How To Get Out)full<![CDATA[#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 Planning
  • 03:12 Humanization and Brand Experience
  • 06:03 Infrastructure and Operations
  • 08:50 Long-term Planning and Retention
]]>85b0b218-75f7-402e-9e1e-fbacdb6e1d61Tue, 08 Sep 2026 18:48:01 GMT<p>Jess &amp; Rachyl dive into the 3 core aspects of planning for profitable Q4 that sets e-commerce businesses up for long-term scalable success: <br />1. Infrastructure (finances, cash flow, inventory, operations)<br />2. Humanization (value prop, positioning, customer experience)<br />3. Q1 &amp; Beyond (retention, subscription, loyalty) <br /><br />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.</p><p></p><p>Chapters</p><ul><li>00:00 The Importance of Q4 Planning</li><li>03:12 Humanization and Brand Experience</li><li>06:03 Infrastructure and Operations</li><li>08:50 Long-term Planning and Retention</li></ul>no00:29:0012#2: Preparing For Q4full<![CDATA[#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+ years
  • the balance between authenticity and strategy in business
  • the challenges and rewards of staying true to the vision while adapting to the changing landscape of business
  • the journey of entrepreneurship, the pitfalls of rushing growth, the irony of fundraising, the misalignment of pacing and vision, and the impact of rushing growth
  • the pressure of rapid scaling, the ugly side of business, the rewiring of business thinking, and the concept of quality over quantity
  • the 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 Authenticity
  • 11:28 Balancing Authenticity and Strategy in Business
  • 20:42 The Evolution of Long Play
  • 29:13 The Journey of Entrepreneurship
  • 31:23 The Pitfalls of Rushing Growth
  • 32:35 The Irony of Fundraising
  • 33:40 The Misalignment of Pacing and Vision
  • 35:29 The Impact of Rushing Growth
  • 36:21 The Pressure of Rapid Scaling
  • 38:04 The Ugly Side of Business
  • 40:59 The Rewiring of Business Thinking
  • 43:00 Quality Over Quantity
  • 47:00 The Inside-Out Approach to Business
  • 56:43 The Radiating Impact of Business Decisions
  • 59:31 The Journey to Solid Foundations
  • 01:11:37 The Sniff Test for Business Problems
]]>abb54ed8-7584-417d-907b-1e7bcb0b3474Tue, 08 Sep 2026 17:55:03 GMT<p>This honest, open conversation delves into what it takes to build a business that is scalable, sustainable &amp; profitable in the long run. Rachyl &amp; Jess share what it's really like behind-the-scenes in a business covering:</p><ul><li>the evolution of Longplay over the last 7+ years</li><li>the balance between authenticity and strategy in business</li><li>the challenges and rewards of staying true to the vision while adapting to the changing landscape of business</li><li>the journey of entrepreneurship, the pitfalls of rushing growth, the irony of fundraising, the misalignment of pacing and vision, and the impact of rushing growth</li><li>the pressure of rapid scaling, the ugly side of business, the rewiring of business thinking, and the concept of quality over quantity</li><li>the inside-out approach to business, the radiating impact of business decisions, the journey to solid foundations</li></ul><p></p><p>Takeaways</p><ul><li>Authenticity and strategy must be balanced in business for sustainable growth.</li><li>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.</li><li>Rushing growth and scaling can lead to significant pitfalls and long-term consequences for a business.</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Journey of Authenticity</li><li>11:28 Balancing Authenticity and Strategy in Business</li><li>20:42 The Evolution of Long Play</li><li>29:13 The Journey of Entrepreneurship</li><li>31:23 The Pitfalls of Rushing Growth</li><li>32:35 The Irony of Fundraising</li><li>33:40 The Misalignment of Pacing and Vision</li><li>35:29 The Impact of Rushing Growth</li><li>36:21 The Pressure of Rapid Scaling</li><li>38:04 The Ugly Side of Business</li><li>40:59 The Rewiring of Business Thinking</li><li>43:00 Quality Over Quantity</li><li>47:00 The Inside-Out Approach to Business</li><li>56:43 The Radiating Impact of Business Decisions</li><li>59:31 The Journey to Solid Foundations</li><li>01:11:37 The Sniff Test for Business Problems</li></ul>no00:51:1211#1: How To Play The Long Game In Businessfull