In this episode of The Retail Pilot, I sit down with David Lafitte, CEO of Tecovas, the Austin-based Western footwear and apparel brand reshaping what it means to build a premium lifestyle business. From radical hospitality to strategic wholesale expansion, David shares how the company has scaled past $200M+, opened more than 50 stores, and become one of the most influential names in modern Western retail. He walks through his unexpected journey from law to leading high-growth consumer brands, his operational philosophy, and what it takes to build a team capable of sustaining long-term momentum. This conversation offers a rare, inside look at brand building, product strategy, retail expansion, and navigating explosive consumer demand, all rooted in the Western lifestyle movement.

Show Notes
How Tecovas grew into a $200M+ brand with more than 50 stores nationwide
The brand’s shift from digitally native to an omni-channel powerhouse
Radical hospitality and how it differentiates Tecovas in-store
Product strategy including women’s growth, denim, shirting, and lifestyle expansion
Wholesale partnerships with Nordstrom, Dillard’s, and independent Western stores
The cultural tailwinds driving Western’s resurgence
Using AI to optimize inventory, customer experience, forecasting, and store allocation
Lessons from taking over leadership from a founder
International expansion opportunities and operational discipline

Enjoy 20% off at Tecovas with the exclusive code PILOT20 at checkout.
👉 Shop Tecovas and use PILOT20 for 20% off.

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In this episode of The Retail Pilot, Ken Pilot sits down with visionary entrepreneur Gregg Renfrew, founder of BeautyCounter and now Counter, to explore what it truly means to disrupt an industry—twice.

After building a billion-dollar brand and selling it to The Carlyle Group, Gregg faced the highs and lows of leadership, loss, and redemption. When BeautyCounter collapsed, she made the bold move to buy it back—relaunching as Counter with a renewed focus on transparency, high performance, and sustainability.

Gregg shares her personal journey of reinvention: from navigating private equity to reclaiming her mission, empowering women entrepreneurs, and redefining what clean beauty means today. She also reveals how Counter is using modern tech, authentic storytelling, and a new direct-to-consumer model to reconnect with customers who care about purpose and performance.

If you’re an entrepreneur, founder, or creative leader determined to rise again after setbacks, this episode offers a masterclass in resilience, reinvention, and leading with vision.

Show Notes:

• The environmental wake-up call that sparked Gregg’s clean beauty mission

• How BeautyCounter grew into a billion-dollar global movement

• Lessons from losing control and the courage it took to buy it back

• The strategy and heart behind launching Counter

• Why she dropped “Beauty” from the brand name and what it symbolizes

• The evolution of community-driven commerce and micro-influencer partnerships

• Using AI, tech, and storytelling to deepen customer relationships

• How Counter is reshaping clean beauty standards with integrity

• Gregg’s advice for women raising capital and owning their power in male-dominated rooms

• The importance of humility, courage, and knowing when to reinvent
  

Listen if you love: stories of comeback, entrepreneurship, clean beauty innovation, and women redefining leadership on their own terms.

Subscribe to The Retail Pilot wherever you get your podcasts and visit counter.com to explore the new collection. Use code PILOT20 for 20% off your first order—exclusive for our listeners. Follow @theretailpilot for more founder stories shaping the future of retail.

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In this episode of The Retail Pilot Podcast, host Ken Pilot welcomes David Lauren, Chief Branding and Innovation Officer at Ralph Lauren. Together, they dive deep into the brand’s 25-year evolution under David’s leadership from pioneering digital storytelling and shoppable windows to launching Ask Ralph, the company’s first consumer-facing AI styling tool. Lauren shares how the balance between creative vision and business discipline has kept Ralph Lauren both timeless and modern, while exploring the future of retail innovation, artificial intelligence, and global brand storytelling.

Listeners will also hear exclusive insights into the company’s hospitality ventures, the magic behind its immersive retail experiences, and a personal look at Ralph Lauren’s legacy, culminating in his recent Presidential Medal of Freedom honor.

If you’ve ever wondered how a heritage brand like Ralph Lauren continues to innovate while staying true to its identity, this episode is a masterclass in vision, leadership, and enduring style.

Show Notes

• Topics covered:

  • The evolution of Ralph Lauren from wholesale to a 70% direct-to-consumer brand

  • How Ask Ralph, the brand’s new AI-powered personal styling tool, is redefining the shopping experience

  • Balancing technology and tradition: using AI without losing authenticity

  • The enduring influence of Ralph Lauren’s creative philosophy and brand discipline

  • Behind the scenes of Ralph Lauren’s innovation milestones from shoppable windows to interactive apps

  • Global expansion and the rise of Ralph Lauren hospitality, including The Polo Bar and Ralph’s in Paris

  • The future of AI in retail and storytelling and why the human touch still matters most

Ralph Lauren’s success story isn’t just about fashion — it’s about vision, storytelling, and timeless innovation.

If you enjoyed this episode, subscribe to The Retail Pilot Podcast for more insider conversations with retail visionaries shaping the future of fashion, business, and innovation.

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In this episode of The Retail Pilot, Sarah Davis and Ben Hemminger, co-founders of Fashionphile, share the remarkable journey of building the largest online platform for buying and selling ultra-luxury handbags and accessories in the U.S. From its beginnings as a small eBay shop in 1999 to a multimillion-dollar brand with flagship locations in New York and California, Fashionphile has become a pioneer in luxury re-commerce.

Sarah and Ben open up about the early challenges of earning consumer trust, overcoming the stigma around pre-owned luxury, and building a model based on authenticity, innovation, and customer experience.

This episode dives into the mechanics of luxury resale, from authentication and pricing to the customer behaviors driving growth. Sarah and Ben also share candid insights on leadership, entrepreneurship, and what it takes to scale a business from a basement to a global stage while staying true to their vision of making pre-owned luxury both legitimate and desirable.

Together, Sarah and Ben discuss:
• The origins of Fashionphile and how they recognized the opportunity in luxury resale
• The importance of authenticity and dispelling myths about pre-owned goods
• How a 90210 address and Rodeo Drive proximity built credibility with customers
• The difference between Fashionphile’s model and competitors like The RealReal and Rebag
• Why their buyout approach creates stronger customer trust and profitability
• The partnership with Neiman Marcus and now Saks Global, and how it has fueled growth
• Their vision for international expansion and the untapped opportunities in luxury re-commerce
• Leadership lessons from building a family business and keeping a team motivated by vision

Tune in now to hear how Fashionphile is transforming the way the world thinks about luxury resale. And remember — subscribe so you never miss an episode of The Retail Pilot.

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What does it take to lead an iconic luxury brand into the future while navigating industry disruption, shifting consumer expectations, and bold strategic moves?

For Marc Metrick, CEO of Saks Global, it is about scale, innovation, and putting the customer at the center of every decision. From steering Saks through its $2.7 billion acquisition of Neiman Marcus Group to launching “The Art of You,” Marc is redefining what luxury retail looks like in a digital-first world.

In this episode of The Retail Pilot, we explore how Saks is transforming its business model, leveraging data and partnerships with Salesforce. ARG and Amazon, and building a new vision of personalization that resonates with today’s luxury consumer. Marc and I had a brief discussion around Saks product being available on Amazon. He is incredibly excited about their Amazon business (only partial catalog available). Saks Global is delivering new customers with high value. Due to certain statistics that we discussed, we had to eliminate the segment.

In this conversation, Marc shares:

• The strategic logic behind combining Saks, Neiman Marcus, and Bergdorf Goodman into one powerhouse
• How “The Art of You” is taking personalization beyond buzzwords to create truly individualized shopping experiences
• The role of technology, AI, and data in modernizing operations and elevating the customer journey
• What partnerships with Amazon and Salesforce have unlocked in terms of scale, efficiency, and innovation
• How Saks is rebuilding trust with vendors and strengthening relationships with brand partners
• Why the US is poised to be the fastest growing luxury market in the world
• His optimism about a new generation of digitally native, experience driven luxury consumers

Whether you are a retail executive, brand strategist, or simply fascinated by the future of luxury, this episode offers a rare inside look at how one of the industry’s most influential leaders is reshaping the way we think about scale, personalization, and the customer experience.

If you enjoyed this conversation, follow and rate the show and share this episode with someone who is curious about the future of luxury retail. The next big insight could be one listen away.

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What does it take to stay relevant in the fast-moving world of Gen Z and Gen Alpha? For Brieane Olson, CEO of PacSun, it’s all about purpose, co-creation, and bold innovation. From signing the Jenner sisters before they became household names to bringing PacSun into Roblox and TikTok Shop, Breanne has made youth culture the company’s North Star.

In this episode of The Retail Pilot, co-hosted by Melissa Gonzalez, we dive deep into how PacSun evolved from a legacy mall brand to a billion-dollar leader in digital-first, Gen Z–centric fashion and what other retailers can learn from their fearless approach.

In this conversation, Brieane shares:

• Her start in retail at age 15 and journey to the CEO seat

• How co-creation with micro-creators is driving viral sales and brand affinity

• The power of music, festivals, and physical retail in the digital age

• How PacSun uses AI across its stores, associate experience, and creative strategy

• The evolving role of Gen Alpha and why brands must meet them where they are

• Why social commerce is no longer optional and how to build it authentically

• Her leadership philosophy rooted in purpose, curiosity, and constant evolution
  

Whether you're a retail executive, marketer, founder, or just obsessed with youth culture trends, this episode is full of actionable insights on what it takes to lead with relevance, empathy, and a fearless willingness to evolve.

If you loved this conversation, don’t forget to follow and rate the show, and share this episode with someone who’s building the next big thing in retail. Your next favorite strategy might just be one listen away.

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What happens when a former lawyer walks out of a high-end jewelry store and into a tattoo parlor—and realizes neither is the right fit? You get Studs—a game-changing brand that’s reinventing the ear piercing and jewelry experience for a new generation of consumers.

In this episode of The Retail Pilot, we sit down with Anna Harman, co-founder and CEO of Studs, to explore how she went from litigation and asset management to building one of the most profitable and experiential brick-and-mortar concepts in retail. With over 30 locations and sky-high four-wall profits, Studs is challenging legacy brands and tattoo shops alike with its safe, stylish, and millennial-friendly approach to ear piercing.

Anna shares insights on:

• Her unlikely journey from law school to launching Studs

• The “aha” moment that sparked the idea

• What makes Studs profitable from day one

• The real competitors (hint: it’s not who you think)

• How she applies startup and retail incubator lessons to build a brand with soul

• Why lab-grown diamonds and curated collabs are driving Gen Z and millennial loyalty

• Her transparent, feedback-forward leadership style and how it shapes team culture
  

Whether you're a brand builder, founder, retail executive, or just love a good reinvention story, this episode is packed with tactical gems and inspiring takeaways.

Ready to reimagine what retail can look like when experience comes first? Follow, rate, and share this episode with a friend and if you’re curious about where to get pierced next, check out studs.com to explore their latest studio openings.

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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 vision

• Why retail needs a new kind of AI-native community

• How AI is transforming roles, business models, and entire org charts

• What makes RetailClub different from every other event on the calendar

• A glimpse into the AI Deep Dive retreat in Huntington Beach
  

Want 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.

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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 thinking

Like 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.

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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 Ventures

• What makes a founder stand out (and why most are first-timers)

• How BCV approaches early-stage vs. growth-stage investing

• Common characteristics of breakout founders like Jen Hyman and Marc Lore

• The importance of customer success and analytic rigor

• AI’s disruptive role in commerce platforms

• Why focus and momentum matter more than perfection

• Personal stories behind high-stakes risk and reward (including Jet.com)

• The investment that got away and the companies he’d double down on

• Rapid fire: Favorite show, CEO admiration, and meeting the Dalai Lama
  

If 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.

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