The Retail Pilot

In this episode of The Retail Pilot, host Ken Pilot sits down with the visionary team behind RetailClub: Anil D. Aggarwal, CEO & Co-Founder, Simran Rekhi Aggarwal, President & Krystina Gustafson, Chief Content Officer & Co-Founder. Known for creating transformative events like Shop Talk and Grocery Shop, this team is once again leading retail into its next great evolution, this time with AI at the center. Together, they discuss the why behind RetailClub, a new kind of gathering designed to bring together AI-curious, AI-championing, and AI-implementing professionals from across the retail industry. Unlike traditional conferences, RetailClub is a dynamic community and immersive experience complete with beachfront workshops, open-air keynotes, and the kind of deep, meaningful dialogue that can only happen face-to-face.You’ll hear how this initiative is less about flashy tech demos and more about building real, practical fluency in AI across functions from merchandising to marketing to customer service and preparing leaders to navigate exponential change. Whether you're just starting to explore AI or already leading its charge, this conversation will show you why RetailClub is the place to be.Key Themes:The story behind RetailClub and its founding visionWhy retail needs a new kind of AI-native communityHow AI is transforming roles, business models, and entire org chartsWhat makes RetailClub different from every other event on the calendarA glimpse into the AI Deep Dive retreat in Huntington BeachWant in?RetailClub’s first retreat takes place September 14–17 in Huntington Beach, CA. This is more than a conference it’s a curated movement to shape retail’s AI-powered future. Don’t miss it. Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, we sit down with Molly Howard, cofounder and CEO of La Ligne, the beloved fashion brand known for its effortless aesthetic, powerful storytelling, and slow burn sustainable success. Molly shares her fascinating path from private equity and investment banking at Credit Suisse to working at Rag & Bone and ultimately launching La Ligne with former Vogue editors Meredith Melling and Valerie Macaulay.You’ll hear how her finance background uniquely shaped the brand’s business model, why La Ligne prioritized profitability over hype, and how her cofounder chemistry laid the foundation for trust and longevity. Molly also opens up about navigating tariffs, scaling e-commerce thoughtfully, and the turning point that made her realize they needed to “drop product like a magazine” to keep customers returning weekly.Whether you're a founder, fashion lover, or just obsessed with good retail strategy, this is a must-listen conversation filled with lessons in leadership, resilience, and intuition.Show Notes:• Molly’s unexpected journey from Credit Suisse to the fashion industry• The early days at Rag & Bone and the deal that flipped her role from banker to brand-side strategist• How a boat ride in Hawaii turned into a cofounder pitch• The vision behind La Ligne’s name and how they built a brand rooted in non-fussy French minimalism• Why La Ligne raised under $4 million and how they’ve remained profitable ever since• The benefit of launching without institutional investors• Dividing responsibilities among three cofounders and why “three is easier than two”• Building a direct-to-consumer first model with mindful wholesale partnerships like Net-a-Porter and Shopbop• The challenges and creativity that came from growing without an early e-commerce hire• Influencer marketing, ShopMy, and keeping authenticity at the center• The La Drop strategy and why weekly product releases became key to customer loyalty• Facing down supply chain shocks and rising tariffs while keeping the brand nimble• The joy of physical retail and Molly’s passion for designing store spaces• Denim, menswear, and collaborations as La Ligne’s next frontiers• Rapid fire: Molly’s favorite brands, best advice received, go-to pieces, and the Tupac class that shaped her thinkingLike what you hear?Follow The Retail Pilot and leave us a review. Share this episode with a friend who loves fashion or dreams of launching their own brand. You can also tag us on Instagram with your takeaways—we’d love to hear what inspired you.Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, we’re joined by Scott Friend, a longtime leader in the retail and venture capital world. A partner at Bain Capital Ventures and the co-founder of ProfitLogic, Scott shares his journey from operator to investor, his unique lens on early-stage startups, and what separates great founders from the rest. We unpack the evolution of BCV over the past 20 years, the power of founder-market fit, and why customer success is non-negotiable in today’s startup landscape.Scott offers candid insights on investing in companies like Rent the Runway, Jet.com, Attentive, Miracle, and Archive, plus his take on AI's growing influence in commerce. From the one that got away (Peloton) to his thoughts on grit, momentum, and the founder’s mindset, this conversation is packed with value for entrepreneurs, investors, and anyone passionate about the future of commerce.Key Topics Covered:Scott’s journey from building ProfitLogic to investing at Bain Capital VenturesWhat makes a founder stand out (and why most are first-timers)How BCV approaches early-stage vs. growth-stage investingCommon characteristics of breakout founders like Jen Hyman and Marc LoreThe importance of customer success and analytic rigorAI’s disruptive role in commerce platformsWhy focus and momentum matter more than perfectionPersonal stories behind high-stakes risk and reward (including Jet.com)The investment that got away and the companies he’d double down onRapid fire: Favorite show, CEO admiration, and meeting the Dalai LamaIf you enjoyed this episode, be sure to subscribe, leave a review, and share with your network. For more insights on the future of commerce and investing, follow The Retail Pilot wherever you get your podcasts.Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this inspiring episode of The Retail Pilot, retail legend Jenny Ming shares her remarkable journey—from launching Old Navy at Gap Inc. to leading transformative growth at Rothy’s. Jenny reveals how she navigated career pivots, built billion-dollar brands, embraced fast fashion logistics, and stayed true to her values through every leadership chapter. This is a masterclass in visionary retail, thoughtful decision-making, and building businesses with purpose.Whether you're an aspiring entrepreneur, retail exec, or brand builder, Jenny’s insights on creating iconic customer experiences, staying nimble, and leading through complexity will leave you inspired and energized.Show Notes:Jenny shares the pivotal moment she was offered the opportunity to launch a new retail brand while planning a move to Hong Kong.How Old Navy went from “Gap Warehouse” to a standalone brand—and why other potential names like “Monorail” and “Forklift” thankfully didn’t make the cut.Her approach to launching with 50 stores from the start, and why thinking like an investor helped shape early decisions.The reality of working with a lean, scrappy team and the lessons she learned in intrapreneurship at Gap Inc.Why Old Navy's lighthearted brand tone and accessible price points resonated with families—and made fashion fun again.Transitioning into CEO roles after Gap, including a decade at Charlotte Russe and her bold comeback at Rothy’s.The importance of sustainability, style, and washability in Rothy’s brand DNA—and how Jenny helped the company return to profitability in months.How she’s expanded Rothy’s into Nordstrom, Bloomingdale’s, Anthropologie, and international markets while maintaining brand integrity.Her take on tariffs, supply chain diversification, and how early planning helped Rothy’s navigate disruption.Why testing, listening, and growing with your team are pillars of her leadership style.Jenny’s thoughts on the power of strategic collaborations, the future of retail tech, and what keeps her inspired as a mentor and coach.Plus: her leadership must-do’s, favorite cities, favorite brands, and what she looks for when hiring.Enjoy the episode? Be sure to subscribe, leave a review, and share it with someone who’s building something bold. Your support helps us bring more candid stories from retail’s top voices to your feed.Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, host Ken Pilot welcomes Emily Gittins, Co-founder and CEO of Archive — a technology company transforming fashion's relationship with resale. With a deep background in mathematics, environmental science, and business, Emily takes us through her journey from Cambridge to BCG to Google X, and eventually to co-founding Archive with a bold vision: enable brands to profit from resale and reduce fashion waste at scale.Emily unpacks how Archive partners with top brands like The North Face, Oscar de la Renta, and New Balance to integrate branded resale into their business models — creating new revenue streams while advancing sustainability. Discover how her team is changing industry perceptions, scaling globally, and pioneering circular solutions in new verticals like home goods and electronics.Whether you're a fashion exec, sustainability advocate, or retail tech enthusiast, this episode offers a masterclass in turning purpose into profit.Show Notes:🔹 Guest BackgroundEmily’s education: BA in Mathematics (Cambridge), MBA & MS in Environmental Science (Stanford)Past experience: BCG, Google X, international development work on gender equity and mobile tech🔹 Key Topics CoveredWhy fashion is responsible for 8% of global greenhouse gas emissionsThe myth of resale cannibalizing full-price salesArchive’s unique tech platform for peer-to-peer resale, in-store trade-ins, and consignmentPartnerships with brands like Lululemon, Doc Martens, and M.M.LaFleurThe data-driven approach to pricing, SKU matching, and profit optimization in resaleScaling Archive internationally and expanding into new categoriesRaising $60M+ in funding and what’s next for the circular economy🔹 Powerful Stats & Takeaways100 billion clothing items are produced annually — enough to clothe the next 6 generationsResale customers have 2–3x higher lifetime value than new-only customersM.M.LaFleur saw a 3% revenue boost in year one from resale aloneResale is expected to become a $350B market🎙️ Listen Now:Available on Spotify, Apple Podcasts, and your favorite streaming platforms.Learn More About Archive:https://www.archiveresale.comSponsored by FireworkHosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, we sit down with Amanda Baldwin, the newly appointed CEO of Olaplex and former CEO of Supergoop, for an in-depth conversation about her remarkable career journey—from Wall Street to the heart of the beauty industry. Amanda shares how her early curiosity about brands evolved into a passion for consumer-driven storytelling, innovation, and leadership in some of the world’s most iconic beauty companies.We explore her pivotal career moments, including her transition from finance to beauty, the foundational experiences she gained at Estée Lauder and LVMH, and how she scaled Supergoop from a small team to a category-defining brand. Now at the helm of Olaplex, Amanda outlines her vision for rebuilding brand strength, deepening pro community relationships, and driving innovation through groundbreaking R&D.This episode offers a masterclass in brand leadership, navigating industry change, and staying grounded in purpose while scaling globally.If you enjoyed this conversation, be sure to like, follow, and leave a review—it helps us reach more listeners and continue bringing you these powerful insights.Show Notes:Amanda’s early curiosity about consumer brands and storytellingLessons learned from Wall Street, Estée Lauder, and LVMHThe early growth story of Supergoop and how innovation drove scaleWhy product quality and emotional connection are non-negotiable for brand longevityOlaplex’s patented technology, salon-first strategy, and Amanda’s plans to reinvigorate the brandInvesting in team, infrastructure, and culture as part of operational excellenceNavigating the public markets while staying focused on long-term brand valueAdvice for early-career professionals and the role of mentorship in her successHosted by Ausha. See ausha.co/privacy-policy for more information.

A few weeks ago, I wrote an open letter to President Trump urging him to reverse the extreme tariffs and embargoes imposed on China. These policies have had a significant impact on the apparel, footwear, and toy industries—industries that have long operated offshore due to cost efficiencies and global supply chains. The response was overwhelming: over 800 reactions, 70,000 views, and 50+ reposts on LinkedIn, reflecting broad concern across the industry.However, the post also sparked a thoughtful and passionate response from a former colleague who sees a different path forward—one that includes a revival of U.S.-based manufacturing.In this episode of The Retail Pilot, we sit down for a grounded, no-holds-barred conversation about tariffs, trade, and the real-world ripple effects on American business. Joining me are:Adrian Miramontes, COO/CFO of Boston Proper, a women’s apparel brand that manufactures 80%+ of its product in China and now faces existential risk due to tariff-related cost increases.Jan Rogers Kniffen, CEO of J Rogers Kniffen Worldwide and longtime retail executive and CNBC contributor, who shares sobering insights on the long-term hollowing out of U.S. manufacturing.Bear Clark, Chief Innovation Instigator at Ear Micro and a pioneer in the hearables industry, who once ran a thriving U.S.-based manufacturing company—until Chinese subsidies and trade shifts changed everything.Together, we explore both sides of the issue—from the hopeful possibilities of automation and fair trade to the painful reality many small-to-mid-sized retailers now face. Whether you're a policymaker, entrepreneur, or consumer, this episode will challenge how you think about global sourcing, pricing, and the future of U.S. industry.You’ll Learn:Why my call to reverse tariffs gained massive traction—and pushbackHow Chinese subsidies disrupted entire U.S. industries, one bid at a timeWhy companies like Boston Proper depend on Chinese manufacturingWhat domestic production could look like in the age of automation and AIWhy rushed trade policy reform could do more harm than good without a planThe moral and economic case for reciprocal trade and environmental accountabilityTopics Covered:The decline of American manufacturing over six decadesFast fashion, fair labor, and environmental implicationsTariffs as economic tools: punishment, leverage, or necessity?What a balanced and effective trade strategy might actually look likeFinal Thoughts:We may not all agree on the solution, but this conversation marks a critical starting point: how can the U.S. support fair, strategic trade that benefits workers, business owners, and consumers alike—without trading stability for short-term politics?Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, host Ken Pilot sits down with Daniella Vitale, CEO of Ferragamo and one of the most influential leaders in luxury retail. From wrapping gifts at a small shop in New Jersey to leading some of the biggest names in fashion — including Armani, Gucci, Barneys New York, Tiffany & Co., and now Ferragamo — Daniella shares her remarkable career journey, pivotal leadership lessons, and deep passion for product innovation.Daniella opens up about navigating the digital transformation of legacy brands, scaling Ferragamo’s digital business, and why authentic customer experiences are the future of luxury. She also discusses her philosophy on leadership, career advice for the next generation, and how Ferragamo is evolving its women's business to drive growth in a challenging global market.Whether you're an aspiring fashion executive, a retail enthusiast, or a brand leader navigating change, Daniella’s insights will leave you inspired, informed, and ready to take bold chances.Show Notes:Introduction to Daniella Vitale’s career in luxury retail, including her leadership roles at Armani, Gucci, Barneys New York, Tiffany & Co., and FerragamoHow wrapping gifts as a teenager sparked her lifelong passion for retailThe importance of embracing both product and operations to become a successful CEODaniella’s experience launching digital at Gucci and transforming Barneys' online businessLessons learned from leading Barneys through financial challenges and innovationDriving Ferragamo’s digital growth and building an omnichannel strategyHow Ferragamo is shifting from a men's shoe powerhouse to a women's leather goods leaderThe critical role of customer experiences, lifestyle branding, and storytelling in luxury todayInsight into the evolving challenges in the luxury retail market — from tariffs to changing consumer behaviorsDaniella’s leadership approach: building cohesive, collaborative, and empathetic teamsAdvice for young professionals entering the retail and fashion industriesRapid-fire questions: favorite brands, dream city to live in, favorite shows, and who she’d love to meetIf you found value in this episode, don’t forget to share it with your network and help us spread these inspiring lessons across the industry!Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, host Ken Pilot welcomes PJ Oleksak, the dynamic CEO of Nuts.com and the first woman and non-family member to lead the 94-year-old business. With a rich background that includes leadership roles at FreshDirect and Slice, PJ shares how she combines a deep understanding of finance with a passion for food to lead transformative change in legacy brands. She walks us through her journey from private equity to pioneering online grocery, her leadership philosophy, and how she’s steering Nuts.com toward omnichannel growth.PJ also discusses the challenges and opportunities in modernizing a family-owned business—building a performance-driven culture, embracing AI and tech innovation, and preparing to launch a sister retail brand. Whether you're in e-commerce, food retail, or scaling a family business, this episode offers practical wisdom on navigating growth while staying true to your roots.Show Notes:Guest: PJ Oleksak, CEO of Nuts.comBackground: Former Chief Growth Officer at FreshDirect and Chief Business Officer at SliceTopics Covered:PJ’s transition from private equity to food techLessons learned from FreshDirect and SliceModernizing a 94-year-old business and earning trust as an outsiderBuilding high-performing, happy teams and instilling accountabilityThe cultural and operational shifts at Nuts.com under her leadershipStrategic moves toward omnichannel growth and retail distributionThe impact of AI across departments, from sales to creativeHow Nuts.com is adapting to rising cocoa costs and sourcing challengesLeadership philosophy and importance of founder-CEO alignmentLooking ahead: launching a sister brand and expanding customer reachKey Insight: Balancing legacy with innovation requires empathy, structure, and a relentless focus on the customer experience.Sponsored by FireworkHosted by Ausha. See ausha.co/privacy-policy for more information.

Join Emily Heyward and JB Osborne, co-founders of Red Antler, as they share insights from their renowned branding agency that has birthed icons like Allbirds and Casper. They explore how AI is revolutionizing retail, enhancing consumer interactions and brand strategies. The duo emphasizes the power of empathy and storytelling in building memorable brands. They also discuss their innovative equity-based partnership model and reflect on their favorite campaigns, all while navigating the evolving landscape of consumer expectations.