Michael Kleinmann is the Founder and CEO of Michael Kleinmann Consulting, a bespoke consultancy helping DTC e-commerce and subscription brands grow. He is also the Founder and CEO of Underwear Expert, a men's underwear platform that evolved from a digital media brand into a leading curated subscription service. As a seasoned e-commerce entrepreneur, Michael spent a decade as the President of Freshpair, where he helped build one of the largest online retailers in the underwear category. With over two decades of experience scaling e-commerce and subscription brands, he focuses on brand building, subscriptions, operations, marketing, technology, and customer experience.

When growth stalls, most brands immediately reach for a new agency, a better campaign, or a larger ad budget. Before pouring more money into an acquisition, leaders have to ask themselves, is the business actually built to scale?

The answer is to diagnose the foundation before trying to scale what sits on top of it. E-commerce operations and subscription expert Michael Kleinmann advises brands to validate their data, focus on gross profit over ROAS alone, and audit their systems for issues with sizing, product structure, COGS, and inventory forecasting. He suggests fixing low-hanging operational problems first, not training customers to expect deep discounts, using 3PLs when fulfillment distracts from growth, and ensuring subscription models have the right infrastructure before launching. Sustainable growth comes from strengthening the systems that support marketing, not simply spending more on acquisition.

In this episode of the Up Arrow Podcast, William Harris sits down with Michael Kleinmann, Founder and CEO of Michael Kleinmann Consulting and Underwear Expert, to discuss fixing the hidden cracks that stop DTC brands from scaling. Michael shares lessons from early e-commerce, subscription complexity, AI opportunities, inventory forecasting, 3PLs, discounting mistakes, and operational audits.

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.

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.

Chadwick Wilson is the Co-founder and Chief Creative Officer at Ace Renegade Productions, a social strategy, video, and content production company specializing in visual branding, social storytelling, and multi-platform marketing. He is also a Senior Casting Producer at Cornwell Casting, a reality television casting company focused on finding dynamic casts across reality TV genres. With over 15 years of entertainment experience, Chadwick was a member of the production staff for 2 Broke Girls and a casting producer on Joe Millionaire, Farmer Wants a Wife, and The 1% Club.

The most memorable ads do more than capture attention — they make people feel something worth repeating. In a landscape of forgettable creative, how can brands turn simple products into stories people actually want to share?

Creative strategist and casting producer Chadwick Wilson says to start with the audience, not the product. Strong brand content comes from emotional relevance, authentic storytelling, and a clear understanding of the message's audience. Brands should avoid casting too wide a net, use humor only when it fits the product, lean into nostalgia or identity when the story calls for it, and make founder-led content feel human instead of overly polished. The goal is to create content that feels personal, memorable, and culturally resonant.

In this episode of the Up Arrow Podcast, William Harris chats with Chadwick Wilson, Co-founder and Chief Creative Officer of Ace Renegade Productions, about creating ads and content people remember. Chadwick shares why brands need emotionally resonant storytelling, how founder-led content builds trust, and what marketers can learn from viral ads by Manscaped, Peloton, Aviation Gin, and McDonald's.