Up Arrow Podcast

William Harris
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  • ENTREPRENEURSHIP
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This is Up Arrow Podcast where we feature successful people in the venture capital, B2B, and e-commerce industries as they discuss how entrepreneurs can improve their business and drive their profits to the next level.

  1. 2D AGO

    Inside the 40-Year-Old Footwear Brand Still Outsmarting Modern eCommerce With Logan Bird

    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. In this episode… 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.

    1h 13m

  2. MAY 12

    "We Had 5 Years of Inventory…and It Almost Killed Us" With Brandi Dugal

    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. In this episode… 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.

    1h 10m

  3. MAY 5

    Why Media Buyers Make Bad Decisions Under Pressure (And How To Fix It) With Rita Ainsworth

    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. In this episode… 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.

    1h 22m

  4. MAR 24

    Culture That Survives the Exit: How Jay Steinfeld Beat the Odds

    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.

    1h 18m

  5. MAR 17

    Random Acts of Marketing Are Killing Your Growth With Jennifer Zick

    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.

    1h 16m

  6. MAR 10

    Why the Best eCommerce Brands Spend More Time on Boxes Than Ads With Jason Wong

    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.

    1h 9m

  7. MAR 3

    The Hidden Cost of Scaling Fast: Why Founders Lose Friends (And the 2-Hour Fix) With Nick Gray

    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.

    1h 11m

  8. FEB 24

    10,000 Hours at the Table: How $1B in Deals Actually Get Done With Patrick Griffin

    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.

    1h 23m
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About

This is Up Arrow Podcast where we feature successful people in the venture capital, B2B, and e-commerce industries as they discuss how entrepreneurs can improve their business and drive their profits to the next level.

Information

  • Creator
    William Harris
  • Years Active
    2023 - 2026
  • Episodes
    147
  • Rating
    Clean
  • Copyright
    © Up Arrow Podcast (c) 2023
  • Show Website
    Up Arrow Podcast