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.

Logan Bird is the President and CEO of Mephisto, a France-based premium footwear brand known for handcrafted comfort shoes. Previously, he served as Mephisto's Vice President of Omnichannel Sales, where he helped advance the brand's digital, retail, wholesale, and DTC strategies. With experience in e-commerce, strategic partnerships, and omnichannel growth, Logan held senior roles at Lands' End and Zappos.

Scaling a brand can feel like a paradox: the faster you grow, the easier it becomes to lose the craftsmanship, culture, and customer trust that made the business work in the first place. In a market obsessed with speed, automation, and shortcuts, how can leaders grow without becoming generic?

Logan Bird's answer is to build around product-market fit, craftsmanship, and people who can execute with focus. As an e-commerce and omnichannel growth leader, he maintains that durable growth starts with knowing your customer, protecting product quality, and creating consistent brand experiences across channels. Leaders should replace manual processes before they break, trust teams enough to let them learn through execution, listen for patterns in customer feedback rather than reacting to the loudest complaint, and hire through trusted networks to find people aligned with the company's vision. The result is a business that scales with stronger systems, clearer priorities, and a deeper connection to its customers.

In this episode of the Up Arrow Podcast, William Harris chats with Logan Bird, President and CEO of Mephisto, about scaling premium brands without losing craftsmanship. Logan discusses product-market fit, omnichannel growth across retail and DTC, and leadership lessons from Japan and Zappos.

Brandi Dugal is the Founder and CEO of The Fidget Game, a company that creates curriculum-aligned learning games to make reading and literacy practice effective and fun. The company's resources are used in more than 50,000 schools. A former teacher with classroom experience in multiple countries, Brandi developed The Fidget Game after working with students who were struggling to read. Through the Fidget Forward program, she makes educational tools more accessible to classrooms and families in need.

Scaling an e-commerce brand often requires a counterintuitive move: letting go of the metrics you once used to measure growth. Yet when growth stalls, how do you know whether to pull back or push harder?

Brandi Dugal's answer is to zoom out, measure the whole business, and keep testing until the system reveals what works. As an educator-turned-e-commerce founder, she recommends looking beyond platform-level ROAS and using marketing efficiency ratios (MERs) to assess overall marketing efficiency. Brandi also suggests separating campaigns by product, tagging ad angles carefully, testing high volumes of creative, and staying close to customers through real conversations, feedback loops, and founder-led storytelling. Sustainable growth comes from pairing disciplined measurement with authentic, customer-informed creative.

In this episode of the Up Arrow Podcast, William Harris chats with Brandi Dugal, Founder and CEO of The Fidget Game, about scaling through creative testing and whole-business measurement. Brandi shares how MER changed her Meta strategy, why authentic founder-led ads outperform polished UGC, and how gamified classroom insights shaped her product development.

Rita Ainsworth is a Human Potential Coach at Rita Ainsworth Coaching, where she helps high-performing professionals and teams reduce stress and improve resilience through neuroscience-based, body-centered coaching. As a trauma-informed coach, she specializes in guiding clients out of chronic stress and into greater clarity, energy, and balanced performance. After spending a decade in marketing and media-buying, Rita spent years studying human performance, neuroscience, and somatic practices to understand sustainable success.

You can have all the experience, data, and strategy in the world and still make the wrong call in a critical moment. Under pressure, even top performers freeze, overreact, or spiral into unproductive action. So what's really driving those decisions when everything is on the line?

According to Rita Ainsworth, a human potential coach specializing in nervous system regulation and performance, it's not your intelligence or skillset — it's your physiological state. When stress takes over, the brain defaults to survival mode, limiting creativity and decision-making. Rita recommends starting with body-based resets like slowing your breath, scanning your environment for safety, or taking short movement breaks to discharge stress. By building awareness of your patterns and practicing regulation techniques consistently, you can shift from reactive to intentional thinking — even in high-stakes situations.

In this episode of the Up Arrow Podcast, William Harris sits down with Rita Ainsworth, Human Potential Coach at Rita Ainsworth Coaching, to discuss how stress impacts decision-making and performance. Rita explains how nervous system states affect outcomes, why high performers fall into burnout cycles, and practical ways to regulate stress and think clearly under pressure.

Jay Steinfeld is the Founder and former CEO of Blinds.com, the world's largest online retailer of window coverings, which was acquired by The Home Depot in 2014. Under his leadership, Blinds.com grew from a bootstrapped startup in his home to a billion-dollar enterprise, earning a reputation for innovation in e-commerce and technology-driven growth. Jay is also a Wall Street Journal best-selling author of Lead from the Core: The 4 Principles for Profit and Prosperity and the Entrepreneur in Residence at Rice University's Graduate School of Business, where he shares business insights.

Building a company is challenging, but building one that thrives without losing its soul is even harder. Leaders may talk about culture, growth, and decision-making, yet few manage to scale while keeping people engaged and energized. How can you create a business that grows sustainably, empowers employees, and thrives even after major transitions?

According to entrepreneur and leadership expert Jay Steinfeld, the answer lies in focusing on people and constant improvement. He emphasizes creating an environment where teams evolve continuously, experiment without fear of failure, and feel empowered to express ideas openly. Leaders should hire people who embrace change, reward contribution without artificial limits, and encourage constant reflection on daily improvements. By making thoughtful decisions despite incomplete information and designing systems that prioritize learning and growth, organizations can build enduring cultures.

In this episode of the Up Arrow Podcast, William Harris chats with Jay Steinfeld, Founder and former CEO of Blinds.com, about building a culture-driven company that scales effectively. Jay explains how personal challenges shaped his entrepreneurial mindset, the Four E's framework for company culture, and the partnership strategy that helped position his company for acquisition.

Jennifer Zick is the Founder and CEO of Authentic, a fractional CMO and marketing firm that helps businesses create scalable growth systems. With more than 25 years of experience in B2B marketing across startups, private equity–backed companies, and global organizations, she is a recognized leader in the fractional CMO space. Jennifer is also the Founder of LIFT Integrator Community™, an executive peer group for second-in-command leaders.

Marketing often starts as a flurry of activity — blog posts, ads, social media, campaigns. Yet many companies still struggle to see consistent growth from those efforts. Leaders invest more money and hire talented people, but results remain unpredictable and disconnected from revenue. Why does marketing feel chaotic in growing companies, and how can businesses transform it into a reliable growth engine?

According to marketing strategist Jennifer Zick, many organizations focus on tactical marketing through activities like content, campaigns, and lead generation without strategic alignment. Instead, leaders should elevate marketing to a strategic function that shapes decisions about positioning, pricing, market entry, and the customer experience. Jennifer recommends clarifying your ideal audience, defining why your brand matters to them, and building trust through consistent messaging across the entire customer journey. When marketing leaders collaborate closely with sales, operations, and finance, companies can align their strategy with measurable outcomes such as customer acquisition cost, retention, and lifetime value — turning scattered efforts into sustainable growth.

In this episode of the Up Arrow Podcast, William Harris sits down with Jennifer Zick, Founder and CEO of Authentic, to discuss how growing companies can move beyond tactical marketing and build strategic marketing leadership. Jennifer explains why random acts of marketing happen in scaling businesses, the difference between tactical "little-m" and strategic "big-M" marketing, and how fractional CMOs align marketing with revenue and long-term growth.