The DTC Mistake That Doesn't Hurt… Until 2 Years Later With Jess Chan and Rachyl Neidecker

Jess Chan is the Founder and Executive Chair of Longplay Brands, a full-service retention and lifecycle marketing agency for DTC e-commerce brands. She is also the Founder and CEO of Backbone, an email strategy automation tool. As a former CMO of a multimillion-dollar DTC e-commerce company, Jess bootstrapped Longplay to seven figures in revenue within the first 18 months. She is a sought-after speaker, podcast guest, product developer, and consultant on topics like retention, lifecycle marketing, and progressive agency business modeling.

Rachyl Neidecker is the CEO and Partner at Longplay Brands. She specializes in turning complex or broken business operations into scalable systems. Previously, Rachyl served as the COO and interim CEO of an eight-figure e-commerce brand, the Director of Operations at COO Alliance, and has consulted for companies with $10M–$100M+ in revenue.

In this episode…

E-commerce brands often chase stronger channels, faster tactics, or higher revenue goals without identifying whether the company's foundation can support the growth. When trust, profitability, and operations are misaligned, even strong marketing can amplify the wrong problems. So how can founders diagnose what's holding their business back?

With expertise in lifecycle marketing and operational leadership, Jess Chan and Rachyl Neidecker point to a more disciplined way to scale. They recommend looking beyond surface metrics to identify root causes, such as brand inconsistency, product-market fit issues, over-discounting, weak customer education, bloated org structures, and hidden logistics costs. Instead of moving fast on foundational decisions, brands should slow down, inspect the full customer journey, build trust at every touchpoint, and optimize for profit and enterprise value — not just revenue. Sustainable growth comes from diagnosing the system before prescribing the tactic.

In this episode of the Up Arrow Podcast, William Harris sits down with Jess Chan and Rachyl Neidecker of Longplay Brands to discuss diagnosing e-commerce growth problems. They cover DTC brands' costly misdiagnoses, lifecycle metrics that reveal root causes, and the difference between scaling revenue, profit, and enterprise value.