Up Arrow Podcast

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. In this episode… 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. In this episode… 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.

Jason Wong is the Founder and CEO of Paking Duck, which provides custom packaging solutions for DTC brands. Before launching Paking Duck, he built and scaled multiple DTC ventures, including Saucy, an end-to-end sourcing and logistics company, and the beauty brand Doe Lashes, which reached significant valuations under his leadership. Jason started his career as a teen entrepreneur in blogging, affiliate marketing, and e-commerce before expanding into international logistics, manufacturing, and supply chain operations. In this episode… Most founders obsess over ads, creative, and conversion rates — but overlook the one thing every customer physically touches. Packaging is often treated as a cost to minimize rather than an asset to optimize. How can the box on your customer's doorstep increase retention, reduce costs, and drive revenue? Packaging manufacturing expert and e-commerce entrepreneur Jason Wong maintains that packaging can be a growth lever. He explains that packaging should be designed as a marketing channel inside the home — something customers proudly display, turning it into a mini billboard that keeps your brand top of mind. Jason advises founders to engineer packaging strategically by reducing dimensional weight to lower shipping costs, reinforcing structural integrity to prevent refunds and chargebacks, and designing with storytelling in mind to strengthen brand perception. When approached holistically, packaging moves from a backend expense to a compounding growth asset. In this episode of the Up Arrow Podcast, William Harris sits down with Jason Wong, Founder and CEO of Paking Duck, to discuss how packaging drives e-commerce growth. Jason explains why packaging is a revenue driver, how smarter structural design reduces shipping costs and damage, and the common mistakes founders make when optimizing purely for cost.

Nick Gray is an entrepreneur, author, and the former Founder and Owner of Museum Hack, a company known for its unconventional, engaging museum tours that make art and history fun and accessible. He grew Museum Hack into a multi-city enterprise with dozens of employees before selling it to his leadership team in a seven-figure deal. Nick is the author of The 2-Hour Cocktail Party and has been featured in major media outlets, including The New York Times and The Wall Street Journal. In this episode… As your business grows, your calendar fills up — but your circle often shrinks. Revenue increases, responsibilities multiply, and before long, most of your conversations revolve around work. How can you intentionally design gatherings that strengthen friendships while fueling smarter business growth? Gathering expert Nick Gray says the answer is to stop leaving relationships to chance and start designing them intentionally. Most networking events fail because they're unstructured and intimidating, but a simple two-hour cocktail-style gathering with 15-22 guests creates the ideal environment for connection. Start with a small core group to guarantee attendance, use name tags and guided introductions to reduce friction, and host in your home to deepen trust. When done consistently, these gatherings strengthen weak ties, open business opportunities, and create genuine friendships. In this episode of the Up Arrow Podcast, William Harris chats with Nick Gray, former Founder and Owner of Museum Hack, about building meaningful relationships through intentional hosting. Nick explains his viral Tokyo stunt, the 15-22 person two-hour party formula, and his 24-hour reply-all tactic to spark post-event connections.

Patrick J. Griffin is a Partner at TableForce, a firm that provides negotiation training for B2B professionals. As a seasoned negotiation expert and strategist, he has negotiated over $1 billion in sales with global financial institutions, specializing in complex financial instruments. Outside of negotiation training, Patrick is the Founder of Morrigan Strategic Advisors, where he provides fractional CFO services and executive advisory consultancy. In this episode… Negotiations can be tricky, often creating anxiety about whether you're getting the best deal. Yet, negotiating isn't always about winning or losing; rather, it's about finding ways to collaborate and create value. How can you approach negotiations with a mindset that benefits both parties involved? High-stakes negotiation trainer Patrick J. Griffin challenges the typical adversarial view of negotiations. He regards them as collaborative problem-solving, where both sides work together to uncover new value. Patrick emphasizes the importance of preparation, understanding what both you and your counterpart value, and being clear on your priorities and boundaries. By focusing on these aspects, you increase the chances of creating long-term, mutually beneficial agreements. In this episode of the Up Arrow Podcast, William Harris sits down with Patrick J. Griffin, a Partner at TableForce, to discuss how to approach negotiation as a collaborative process. Patrick shares insights on shifting from transactional to relational negotiations, why high expectations lead to better outcomes, and how founders often overlook value outside of price.

Cherene Aubert is the CEO of Growth Capital, a growth marketing firm that scales consumer brands. As a seasoned e-commerce and digital growth leader, she has nearly two decades of experience scaling DTC brands and managing media investments across multiple high-growth companies. Before Growth Capital, Cherene was the Fractional SVP of Digital & eCommerce at ILIA Beauty, where she drove omnichannel digital strategy for a rapidly growing clean beauty brand. In this episode… Marketing has become automated and identical across companies. Brands chase the same ads, channels, and short-term wins, only to discover that growth stalls and loyalty disappears. How can you build something memorable and scale without losing trust? The way forward starts with obsessing over customers, not competitors. As a growth and e-commerce leader, Cherene Aubert maintains that brands should use customer insights — from ad data to conversations — to guide creative strategy, redefine quality as value for the customer, and invest in full-funnel thinking. This requires originality, emotional resonance, and the space for creative teams to build long-term demand rather than quick conversions. In this episode of the Up Arrow Podcast, William Harris sits down with Cherene Aubert, CEO of Growth Capital, to discuss how brands can escape the marketing echo chamber. Cherene explains why copying competitors backfires, how full-funnel content drives sustainable growth, and how premium and beauty brands can stay culturally relevant.

Kevin Anderson is the Founder and CEO of Kevin Anderson & Associates, a global leader in professional book-writing, editing, and publishing navigation services. A #1 New York Times best-selling editor, national best-selling author, entrepreneur, and investor, Kevin has built KAA into an industry-leading firm with a team of former Big-5 executive editors, literary agents, and best-selling writers. Since founding the company in 2007, he has helped launch thousands of authors and contributed to hundreds of national and international bestsellers. Kevin is also the Founder of Dissertation Editor and the co-author of the Wall Street Journal bestseller PhDone. In this episode… Books can elevate ideas beyond the noise of social media and fast-moving content. They don't just share information — they build credibility, trust, and lasting authority in a way few other mediums can. How can publishing a book open doors for founders? According to best-selling editor and publishing expert Kevin Anderson, books signal depth, expertise, and timeless value, making them a powerful tool for entrepreneurs who want to stand out. He notes that the ROI isn't in book sales, but in the opportunities that follow: media visibility, stronger SEO authority, and increased trust from high-level audiences. Kevin encourages founders to publish before they think they're ready, focusing on solving readers' problems rather than waiting to feel like they've accomplished enough. A well-positioned book becomes a long-term asset that compounds influence over time. In this episode of the Up Arrow Podcast, William Harris talks with Kevin Anderson, Founder and CEO of Kevin Anderson & Associates, about how books help founders build authority and unlock new opportunities. Kevin discusses why books create lasting credibility, how they generate ROI through media and visibility, and how founders can maximize impact after publication.

Ross Correia, Co-founder and CEO of Reactiv and former Shopify leader, builds AI mobile commerce that boosts retention. He explains why reliance on paid ads is risky. He makes a case for mobile apps and App Clips to reduce friction. He covers thoughtful notifications, app-first features, AI-timed outreach, privacy boundaries, and choosing long-term product quality over quick wins.

Mikel Lindsaar is the Founder and CEO of StoreConnect, a customer commerce platform that helps businesses unify e-commerce sales, services, and systems. As a seasoned technology entrepreneur, he founded multiple software companies, including Exec IO and reinteractive, and exited several SaaS ventures. In this episode… Growth doesn't just stall when the business is underwater; it stalls when everything appears to be working, yet decisions slow, complexity piles up, and momentum fades. Leaders often feel the weight before they can recognize the cause, sensing friction in meetings, handoffs, and execution. What causes companies to break, and how can founders remove barriers before they compound? According to seasoned technology entrepreneur Mikel Lindsaar, the root issue is decision-friction, and he argues that leaders must design organizations to move decisions faster, not upward. He emphasizes replacing "maybe" with clear yes-or-no frameworks, pushing ownership closer to the work, and using simple metrics to reveal problems early. Leaders can also turn repeated questions into written guidance and coach teams to present solutions rather than just problems. These practices create speed, trust, and resilience at scale. In this episode of the Up Arrow Podcast, William Harris chats with Mikel Lindsaar, Founder and CEO of StoreConnect, about designing organizations that scale through clarity and speed. Mikel explains why indecision kills momentum, how policies and metrics empower teams, and what founders must do personally to sustain long-term leadership effectiveness.

In this discussion, Jason Anderson, COO of Andzen and a CRM strategist with over a decade of experience, reveals critical mistakes brands make in customer journeys. He emphasizes the importance of valuing work to attract high-LTV customers rather than merely chasing low-cost ones. Jason shares insights on effective customer segmentation, reviving dormant clients through strategic outreach, and the pitfalls of poorly managed loyalty programs. He also highlights how integrating data can significantly enhance targeting and conversion efforts.