Ken Pilot interviews Denise Incandela for this flight of The Retail Pilot. Denise Incandela is Executive Vice President of Fashion and Private Brands for Walmart U.S. In this role, Denise is propelling Walmart’s reputation as a fashion destination, helping democratize access to stylish, quality apparel for Walmart’s 140 million weekly shoppers.Before joining Walmart, Denise rose through the fashion industry ranks with roles as CEO of Aerosoles, President of Global Digital and Customer Experience for the Ralph Lauren Corporation and before that, EVP and CMO of Saks Fifth Avenue. Denise started her post MBA career at McKinsey & Company, where she was a leader of its retail practice.Denise is a visionary retail executive and experienced public company board director who has transformed luxury brands and mass retailers for over 20 years, and she is renowned across the industry for her innovation and vision, team leadership and ability to drive results.Key takeaways from this podcast interview include:1.    Transformational Leadership: Denise Incandela's career trajectory reflects a commitment to transformational leadership. From her beginnings in investment banking and management consulting to her roles at Saks, Ralph Lauren, and Walmart, she has consistently sought opportunities to drive change and innovation within the retail industry.2.    Early Adoption of E-commerce: Denise's entry into the retail industry was marked by the nascent stage of e-commerce. Her pivotal role in launching Saks' e-commerce business in 1999 highlights her foresight and willingness to embrace new technologies and trends, even when they were not widely accepted.3.    Shift from Luxury to Mass Market: Denise's transition from luxury brands like Saks and Ralph Lauren to Walmart represents a significant shift in focus and target demographics. Despite the apparent disparity between luxury and mass-market retail, Denise saw an opportunity to leverage her expertise and drive transformation within Walmart's fashion segment.4.    Building Strong Private Brands: Walmart's focus on developing private brands with distinct identities and market appeal is evident. Denise highlights the importance of building robust design teams and investing in brand development to create cohesive, desirable offerings exclusive to Walmart.5.    Innovative Online Experience: Walmart's efforts to enhance the online shopping experience, particularly in the fashion segment, showcase a commitment to innovation. Features such as virtual try-on and social commerce initiatives demonstrate Walmart's willingness to embrace emerging technologies and adapt to evolving consumer preferences.6.    Transformational Focus: Walmart is heavily focused on transformation, particularly in the fashion sector. They recognize the need to evolve beyond their dominant apparel business and explore new opportunities to grow.7.    Marketing Evolution: The company acknowledges the changing landscape of consumer behavior and the importance of adapting marketing strategies accordingly. This includes leveraging technology and online platforms to reach consumers where they are.8.    Marketplace Strategy: Walmart places significant emphasis on its marketplace strategy, which allows third-party sellers to offer products on its platform. This approach enables Walmart to expand its assortment without the need for additional inventory, contributing to growth and customer satisfaction.9.    Store Reinvention: Walmart is actively reinventing its physical stores to enhance the fashion shopping experience. This involves overhauling assortments, improving visual displays, incorporating digital elements, and creating brand-focused environments to change consumer perception and drive sales.10. Team Collaboration and Leadership: The success of Walmart's fashion transformation relies heavily on teamwork, leadership, and collaboration. Denise Incandela emphasizes the importance of building relationships, influencing others, and fostering a talented team to drive the company's vision forward. She also highlights the need for continuous innovation and addressing internal challenges to sustain momentum and achieve long-term goals.

Ken interviews Amy Williams, the CEO at Citizens of Humanity Group, for this Flight of The Retail Pilot. Amy joined Citizens of Humanity as the company’s President in 2009 and ultimately assumed the Chief Executive Officer position in 2015, overseeing the business for the company’s family of brands including Citizens of Humanity and AGOLDE. Williams previous experience includes Executive Vice President at Lucky Brand Jeans and Senior Vice President of Product Development and Design for Gap Inc. Williams serves on the board at Girls Inc of Greater Los Angeles and empowerHER. She is an advisor to Every Mother Counts and Bay Area Women’s Sports Initiative. Key Takeaways Include:1.    Bridging Business and Design: Amy's career trajectory highlights the importance of bridging the gap between business strategy and creative design in the retail industry. She emphasized the significance of understanding consumer preferences, maintaining commercial viability, and fostering collaboration between merchandising and design teams. This balance between creativity and business acumen is crucial for successful product development and brand growth.2.    Entrepreneurial Leadership: Amy's transition from corporate roles to entrepreneurial ventures demonstrates her adaptability and leadership versatility. She thrived in both structured corporate environments, such as at Gap Inc., and in more dynamic, entrepreneurial settings, such as at Lucky Brand and Citizens of Humanity. Her ability to navigate different organizational cultures and drive results underscores the importance of entrepreneurial spirit and strategic vision in leadership roles.3.    Strategic Distribution Expansion: At Citizens of Humanity, Amy was tasked with developing a distribution strategy to expand beyond traditional wholesale channels. This involved exploring opportunities in specialty retail and e-commerce while working closely with company founders and private equity stakeholders. Amy's focus on diversifying distribution channels and adapting to evolving market trends reflects the agility and foresight required to drive brand expansion and maximize growth potential in the competitive retail landscape.4.    Sustainable Growth and Brand Integrity: Amy emphasizes the importance of sustainable growth and brand integrity. Citizens of Humanity and A Golde focus on quality products, investing in design, and maintaining high standards in distribution. They prioritize long-term brand development over short-term financial gains, taking inspiration from European brands that prioritize generational development.5.    Strategic Expansion and Retail Experience: The company aims to expand its retail presence thoughtfully, focusing on creating experiential and lifestyle-oriented stores rather than rapid expansion for the sake of growth. They seek to deepen relationships with existing retail partners, improve retail presentations, and explore opportunities for retail expansion in select locations.6.    Marketing and Brand Building: Instead of traditional marketing methods, Citizens of Humanity and A Goldie rely on organic brand building and word-of-mouth promotion. They prioritize product quality and strategic partnerships with tastemakers, avoiding paid advertising and focusing on creating a desirable brand image through events, partnerships, and thoughtful product placement.7.    Focus on Technology and Operations: While the company acknowledges the importance of technology in advancing their business, they admit to being more focused on other aspects due to their smaller team size. However, they recognize the need for technological advancements, particularly in areas such as inventory management and data analytics. Improving inventory accuracy, tracking product performance, and optimizing operational efficiency through technology are seen as key priorities for future growth and scalability.8.    Commitment to Sustainability: Citizens of Humanity and Agolde have made sustainability a core aspect of their brand identity. They prioritize responsible sourcing practices, including the use of regenerative cotton and recycled materials. This commitment extends beyond product quality to environmental stewardship, reflecting a broader ethos of corporate responsibility and long-term sustainability. Their approach demonstrates a blend of ethical considerations with business strategy, positioning them as leaders in sustainable fashion within the industry.

Ken interviews Simeon Siegel, Managing Director, Senior Analyst of Retail and eCommerce for BMO Capital Markets.Key takeaways from the interview include:1.    Role as an Equity Research Analyst: Simeon's job involves assessing publicly traded companies within the retail sector. He emphasizes the importance of being objective in his analysis, even if it means delivering hard truths that may not always be well-received by company stakeholders.2.    Divergence in Retail Performance: Despite macroeconomic fears and media narratives about the decline of retail, Simeon highlights that many retail companies are performing well. He notes significant revenue growth and improved gross margins in the retail sector, indicating positive consumer behavior.3.    Impact of Interest Rates: Simeon discusses the potential effects of Federal Reserve decisions on retail performance. While lower interest rates traditionally stimulate spending, he suggests that the impact may not be as significant for retailers, particularly those with strong cash positions and minimal debt.4.    Segment-Specific Performance: Retail success varies across different sectors and brands. Simeon emphasizes that success in retail requires a compelling story, understanding of the target customer, and execution. He notes that while certain sectors like luxury and teen retail are thriving, success isn't guaranteed solely by being in a favorable sector.5.    DTC (Direct-to-Consumer) Realities: There's a growing realization that DTC isn't always the golden solution it's made out to be. Removing the middle person doesn't necessarily lead to cost savings for the consumer; instead, the costs are absorbed differently. Brands pivoting to DTC may not see the expected increase in revenue, gross margin, or profit.6.    The Power of Off-Price Retailing: TJX (T.J. Maxx, Marshalls, HomeGoods) is recognized as a disruptor in the retail sector, despite its minimal e-commerce presence. Their model of selling expensive items at discounted prices has reshaped consumer perceptions and buying habits. Other off-price retailers may also take share from consumers but in different ways.7.    Reevaluating Growth Strategies: Companies like Under Armour, despite revenue size, may face challenges due to low gross margins. Reevaluating strategies, possibly shifting from over-distribution to focusing on quality over quantity sales, may be necessary for sustained profitability.8.    Tech Integration in Retail: While technology offers numerous solutions for retail, the challenge lies in identifying the most effective ones amidst the plethora of options. Companies should focus on tech solutions that reduce shrink, automate supply chains, and improve customer targeting, without letting technology overtake the core business.

Ken interviews Nyakio Grieco, Co-founder of Thirteen Lune and Founder of Relevant: Your Skin Seen on this flight of The Retail Pilot - Leaders & Legends.Nyakio (pronounced Neh-Kay-Oh) Grieco is a beauty entrepreneur and advocate for clean, inclusive beauty that suits all skin types, tones, and needs. As a veteran beauty founder and trusted industry voice, Nyakio has launched successful businesses: her award-winning brand nyakioTM, based on her family’s Kenyan roots and beauty secrets that launched in 2002, and inclusive beauty e-commerce destination, Thirteen Lune, launched with cofounder Patrick Herning in 2020. Thirteen Lune launched as the first of its kind, e-commerce destination designed to inspire the discovery of beauty brands created by BIPOC founders that resonate with people of all colors. Thirteen Lune has since partnered with retailer JC Penney for inclusive beauty shop-in-shop locations in over 600 stores nationwide.Continuing her commitment to inclusive beauty Nyakio created Relevant: Your Skin Seen, a clean, science-led skincare brand that works for all skin tones and types. Working with top labs to ensure a diverse mix of chemists, Nyakio formulated each product with superfruits and actives in efficacious percentages to create products that truly perform. Most recently, the brand expanded into the cosmetics category with six color and complexion products. All products in the range are formulated with skincare benefits and serve and celebrate every skin tone, while hyper prioritizing consumers who have been underserved. Most recently, Nyakio Grieco has been honored with the CEW 2023 Female Founder Award, the Beauty Matter 2023 Future50 Award and included on the Inc. Magazine 2023 Female Founders 200 List. Key takeaways from the interview include:1.    Cultural Heritage and Beauty: Nyakio Grieco's journey into the beauty space was deeply influenced by her Kenyan heritage, particularly her grandmother's beauty secrets rooted in natural ingredients like coffee beans and sugar cane. This connection to her family's traditions and the use of earth-derived elements shaped her early interest in skincare.2.    Transition from Entertainment to Beauty: Despite initially pursuing a career in sports and entertainment, Grieco found herself drawn to the beauty industry through her work with actresses and exposure to beauty products. She noticed a gap in the market for products celebrating Africa's rich resources and heritage, leading her to pivot her career towards beauty entrepreneurship.3.    Challenges of Entrepreneurship: Grieco faced significant challenges as a black female founder, especially in accessing capital and navigating the beauty industry's landscape. Despite setbacks and failures, she persevered, leveraging mentorship, resourcefulness, and industry connections to keep her brand afloat and eventually succeed.4.    Creation of ThirteenLune: Following the acquisition of her brand by Unilever, Grieco co-founded Thirteen Lune with Patrick Herning, aiming to create an inclusive beauty retail platform highlighting products by black and brown founders. The platform aims to debunk stereotypes and provide visibility for diverse beauty brands, challenging the notion that these products are only for specific demographics.5.    Expansion and Future Vision: Despite the rapid growth of Thirteen Lune through partnerships with JCPenney and other retailers, Grieco remains focused on expanding the platform's direct-to-consumer presence and nurturing its brand identity. She sees opportunities for standalone stores, global expansion, and further development of their private label brand, Relevant. The goal is to continue championing diversity in the beauty industry while nurturing and growing the brands within the Thirteen Lune ecosystem. 6.    Thirteen Lune’s Business Model: Unlike a typical marketplace, Thirteen Lune takes a physical position on inventory by importing products into the country, owning the goods, and then selling them to customers. They do not drop ship and prioritize owning the customer experience, ensuring consistency and brand representation across channels.7.    Launch of Relevant: Nyakio discusses launching Relevant as an opportunity to realize her dream brand. With Relevant, she aims to address market gaps and ensure all consumers feel seen at shelf, especially those with melanin-rich skin. The brand focuses on inclusivity, leveraging expertise in formulations and product testing.8.    Expansion and Distribution: Relevant's expansion into Sephora UK demonstrates growth and opportunity for the brand. Grieco emphasizes the importance of partnerships and distribution channels, such as JCPenney, to reach a wider audience and fulfill the brand's mission of inclusivity.9.    Marketing Strategies: Authenticity is central to Thirteen Lune and Relevant's marketing approach. Grieco emphasizes telling authentic stories that resonate with underserved consumers. In the early stages, they prioritized organic strategies over paid marketing and leveraged partnerships to amplify their message.10. Challenges and Opportunities: Grieco highlights the challenges of access to capital for people of color founders, despite the immense potential of diverse businesses. However, she remains optimistic about the shifting landscape and sees opportunities for growth through strategic partnerships, investments, and technological advancements.

On this Flight of The Retail Pilot Ken speaks with LEGEND, Tommy Hilfiger, Principal Designer, Tommy Hilfiger Global.Uplifting and inspiring consumers since 1985, Tommy Hilfiger has pioneered one of the world’s most recognized premium lifestyle brands. With Hilfiger’s vision and leadership as Principal Designer, his eponymous brand celebrates the essence of classic American style with a modern twist. Tommy Hilfiger offers premium quality and value to consumers worldwide under the TOMMY HILFIGER and TOMMY JEANS lifestyles, with a breadth of collections including men’s, women’s and kids’ sportswear, denim, accessories, and footwear.Hilfiger’s career in fashion began when he was a high school student in 1969 — opening his first store, People’s Place, in his hometown of Elmira, New York. A decade later, he moved to Manhattan to pursue a career in fashion design, before launching his namesake brand with a single menswear collection. Since then, global retail sales of TOMMY HILFIGER products have grown to reach approximately $9.1 billion in 2022, powered by more than 16,000 associates worldwide — present in 100 countries and more than 2,000 retail stores, including its largest global flagship store at tommy.com.Hilfiger has a longstanding passion for philanthropy and making the world a better place for future generations. Through the global TommyCares organization, the brand supports various international initiatives and charities like Save the Children, the World Wildlife Fund and Fashion Minority Alliance. Hilfiger currently sits on the Board of Next for Autism. Through the Tommy Hilfiger Fashion Frontier Challenge and People’s Place Program, the brand is also making strides in its ambitious vision to create fashion that Wastes Nothing and Welcomes All – which actively focuses on topics such as social and environmental sustainability, diversity, and inclusivity in fashion and beyond.Diverse achievements in business and fashion have earned Hilfiger numerous distinguished awards including the CFDA’s prestigious Geoffrey Beene Lifetime Achievement Award in 2012, British GQ’s Design Legend of the Year in 2020, BFC’s Outstanding Achievement Award in 2021 and WWD's John B. Fairchild Honor for Lifetime Achievement in 2022. Hilfiger’s life and career have been chronicled in his memoir, American Dreamer, published in November 2016 — reflecting his experiences in the fashion industry from the last 35-plus years. Recounting his early childhood and formative years, it explores the setbacks, triumphs, and sheer determination that drove him to build a multi-billion-dollar global brand.Key takeaways from this interview include:Tommy Hilfiger's Background: Tommy Hilfiger began his journey in retail and design at a young age, starting his own business at 18 years old by opening a retail store -People’s Place - selling jeans in 1969. This venture eventually led him to designing and creating products for his stores, culminating in the establishment of his own brand.Innovative Store Concepts: Hilfiger's early stores, particularly People's Place, were not just retail outlets but cultural hubs influenced by music and fashion. They offered a variety of products, hosted band practices, and provided an immersive experience for customers, aligning with the youth culture of the time.Cultural Influences on Brand Identity: Hilfiger aimed to differentiate his brand from traditional preppy styles by infusing it with elements of music, particularly hip-hop, and embracing a more inclusive approach to fashion. This cultural fusion helped establish the personality of the Tommy Hilfiger brand.Disruptive Advertising Strategy: The Hangman ad campaign, conceived by advertising executive George Lois, was a bold and disruptive move that garnered attention for the brand. Despite initial criticism, the controversial campaign succeeded in sparking conversation and establishing Tommy Hilfiger as a distinctive player in the fashion industry.Strategic Partnerships and Growth: Strategic partnerships, such as those with Marjani International and later with Silas Chao and Lauren Stroll, played a crucial role in the brand's growth and expansion. These partnerships facilitated strategic decisions like expanding into Europe and launching successful product lines such as fragrances, contributing to the brand's success and eventual IPO.Archives and Relevance: Both Tommy Hilfiger and Karl Lagerfeld emphasized the importance of going back to fashion archives and making past designs relevant for today's market. This approach ensures a timeless appeal while staying fresh.Strategic Partnerships: The acquisition by Apex and subsequent sale to PVH provided strategic opportunities for Tommy Hilfiger's brand growth. Apex helped in repositioning the company, while PVH's ownership of other brands like Calvin Klein created synergies beneficial for both.Brand Positioning: The positioning of Tommy Hilfiger's brand differs between the US and Europe. Understanding regional customer preferences and pricing strategies is crucial for successful brand positioning.Design Process: Tommy Hilfiger's use of technology, such as 3D design, and the centralization of its design team in Europe contribute to a more efficient and precise design process. This enables faster response to market trends and ensures product quality.Marketing and Brand Communication: The brand utilizes a mix of influencer collaborations, celebrity endorsements, and unique marketing campaigns to amplify its brand message. Embracing digital technologies like augmented reality and exploring AI's potential are also part of the brand's forward-thinking approach to marketing.

Ken interviews Nick Graham, CEO of SPACEONE Industries and Founder and Chief Underpants Officer of Joe Boxer. Nick Graham changed the face of fashion when he turned his underwear company into one of America¹s most popular lifestyle brands. Graham coined the phrase "The Brand is the Amusement Park, the Product is the Souvenir” and uses this philosophy in everything he does.Graham was the first clothing designer on the internet in 1992, did the first live-streaming fashion show with Microsoft from an airplane hangar in Iceland and in 1998 installed the world’s largest e-mail in New York’s Times Square. He holds the record for the highest point a pair of underwear has been alone, (120,000 feet by single thrust rocket), and the unofficial record for the Worlds Fastest Fashion Show, (1.2 seconds by Human Cannonball).He staged the first transatlantic runway show 30,000 feet above Greenland with his friend Richard Branson, and is currently collaborating with Bill Nye the Science Guy.Currently Graham is the CEO of SPACEONE Industries that designs and produces space inspired consumer products for Men, Women and Children and is distributed through better department stores in the United States. The company also produces products for private space companies including Blue Origin, and Axiom to name a few. Graham has collaborated with many numerous space initiatives over his career including being major sponsor of the 50th Anniversary of Apollo 11 at Kennedy Space Center, launching Virgin Galactic with Richard Branson and having Apollo 11 astronaut Buzz Aldrin and Science Guy Bill Nye walk in his Men’s fashion show called “Life On Mars” at New York Fashion Week.1.    Building Personal Relationships in Business: The conversation between Ken and Nick highlights the importance of personal connections in business relationships. Despite the professional setting, their banter shows a long-standing friendship, emphasizing the significance of personal rapport in business dealings.2.    Entrepreneurial Journey: Nick Graham's journey from designing ties to founding Joe Boxer illustrates the entrepreneurial spirit and the unpredictable paths that lead to success. From humble beginnings to significant brand launches, his story underscores the importance of seizing opportunities and embracing creativity.3.    Branding and Marketing Strategy: Nick Graham's approach to branding emphasizes emotional engagement and storytelling. His philosophy that "the brand is the amusement park and the product is the souvenir" encapsulates the idea of creating an emotional connection with consumers, transcending the mere transactional aspect of purchasing.4.    Innovation and Adaptation: The evolution of Joe Boxer, from its inception to its collaborations with major retailers like Macy's and Kmart, demonstrates the importance of innovation and adaptation in staying relevant in the market. Nick's willingness to pivot and explore new ventures, such as his foray into fragrance and consulting with JCPenney, underscores the entrepreneurial mindset needed for sustained success.5.    Community and Brand Loyalty: The discussion touches upon the significance of building a community around a brand and fostering brand loyalty. Nick highlights the importance of understanding and speaking to the target audience, creating a sense of belonging, and fostering brand evangelism among consumers. This underscores the idea that successful brands go beyond selling products; they create a lifestyle and communitythat resonates with their audience.6.    Humor and Emotional Connection in Branding: Nick Graham emphasizes the importance of incorporating humor, irony, and a sense of fun into brand design to create emotional connections with customers. He believes that this approach sets his brands apart in industries where seriousness is the norm.7.    Innovative Marketing Strategies: Graham shares examples of unconventional marketing strategies he implemented, such as organizing a fashion show in Iceland to promote Joe Boxer underwear. These bold tactics helped his brands gain attention and differentiate themselves from competitors.8.    Partnerships and Collaborations: Graham highlights the significance of partnerships and collaborations in business growth. He mentions working with influential figures like Richard Branson and Bill Nye, as well as collaborating with space companies like Blue Origin and NASA for his latest venture, Space One Industries.9.    Evolution of Career and Business Ventures: From his early days in the garment industry to venturing into space-related businesses, Graham's career trajectory showcases adaptability and a willingness to explore new opportunities. His latest venture, Space One Industries, demonstrates his forward-thinking approach to design and sustainability in the space industry.10. Reflecting on Past Decisions and Learning from Mistakes: Graham reflects on past decisions, acknowledging that some opportunities may have been missed due to holding onto projects too long. He emphasizes the importance of learning from mistakes and making decisions more thoughtfully in hindsight, showcasing a growth mindset in business.

Ken speaks with Lori Coulter, Co-Founder and CEO of Summersalt, on this Flight of The Retail Pilot - Leaders & Legends. Lori Coulter is the Co-Founder and CEO of Summersalt, a generation-defining lifestyle brand known for its data-backed fit and designer quality products without the designer price tag. In 2020, she was named one of Inc. Magazine’s Top 100 Female Founders. Lori and her Co-founder, Reshma Chattaram Chamberlin, launched Summersalt to change the conversation around swimwear and address a true market gap by creating designer swimwear without the designer price tag. Summersalt’s product is data-backed with 1.5 million measurements taken from 10,000 women’s body scans.From day one, Summersalt knew it wouldn't stop at swimwear. The first challenge was to transform the swimwear shopping experience from being intimidating and vulnerable to fun and empowering. Quickly, Summersalt expanded to include adventure-friendly essentials that help make every aspect of a woman's wardrobe more joyful and comfortable—from sleepwear to intimates to activewear. Named one of the Top 100 Upstarts in the world by CNBC, The Lead’s Breakout Company of the Year, and Fast Company’s Brands That Matter in 2022, the brand has seen exceptional growth and consumer adoption, garnering praise from leading outlets including Vogue, Elle, CNN and Forbes. Prior to launching Summersalt, Lori, a veteran start-up founder with deep expertise in design, supply chain and ecommerce, launched one of the first mass customization startups at the intersection of technology, fashion and data to incorporate body scanning and made-to-order manufacturing. Lori holds a Master of Business Administration from Washington University in St. Louis and a Bachelor of Business Administration from Baylor University. She serves on the Board of Trustees at her alma mater Washington University in St. Louis and champions inclusive economic development and entrepreneurship as a member of the University’s Skandalaris Center National Council. Outside of Summersalt, Lori enjoys spending time with her husband and two sons, and exploring the world through her love of travel and adventure. Key takeaways from this episode are:1.    Customer-Centric Approach: Lori Coulter emphasizes the importance of understanding and meeting the needs of the consumer. From the early stages, they focused on creating swimwear that empowered women to feel confident and engage with life. Their emphasis on fit, inclusivity, and sustainability reflects their commitment to their customers' values and preferences.2.    Direct-to-Consumer Success: Summersalt's success largely stems from its direct-to-consumer business model. By bypassing traditional retail channels and selling directly to customers online, they maintain a closer connection with their audience and have more control over their brand experience. This approach allowed them to optimize fit based on real-time feedback and manage returns effectively.3.    Strategic Partnerships and Collaborations: Summersalt leverages strategic partnerships and collaborations to expand its reach and grow its brand. They've collaborated with major retailers and plan to continue doing so, utilizing physical retail spaces alongside their online presence to reach a wider audience.4.    Adaptability and Resilience: The company demonstrated adaptability and resilience, particularly during challenging times such as the COVID-19 pandemic. Despite facing a significant drop in revenue, they managed to bounce back and even thrive by tapping into consumer demand for swimwear and leveraging their online presence.5.    Holistic Marketing Strategy: Summersalt employs a comprehensive marketing strategy that encompasses various channels, including press, influencer partnerships, social media, direct mail, and physical retail. By creating a 360-degree brand experience, they ensure multiple touchpoints with their target audience, enhancing brand visibility and engagement.6.    AI Integration in Marketing: Coulter highlights the significance of AI in marketing, emphasizing its role in anticipating consumer needs, creating timely content, and optimizing customer acquisition strategies. Companies that quickly adopt and leverage AI technologies are likely to emerge as clear winners in the competitive landscape.7.    Success with Connected TV: Coulter discusses the success her company has experienced with connected TV advertising, citing efficiency gains and real-time data feedback as key benefits. Leveraging data signals from direct-to-consumer interactions, such as those obtained from connected TV, allows for more targeted and effective marketing efforts.8.    Influencer Partnerships for Content Creation: Coulter emphasizes the importance of influencer partnerships in content creation, highlighting a Jet Setters program where influencers collaborate with the brand to create authentic and engaging content. Leveraging influencers helps amplify brand messaging and reach a wider audience.9.    Stage-Appropriate Tech Stack: Coulter shares insights into building a tech stack that aligns with the stage of business growth, emphasizing the importance of prioritizing platforms based on consumer needs and operational efficiency. Continuously evaluating and adjusting the tech stack to eliminate redundancies and streamline operations is crucial for scalability.10. Challenges in a Post-COVID Retail Landscape: Coulter identifies three major challenges facing her company in the post-COVID retail environment: understanding shifts in consumer behavior and the future of retail, navigating fundraising challenges in a venture capital landscape impacted by COVID, and refining merchandising strategies to adapt to changing consumer preferences and market dynamics. Flexibility, adaptation, and strategic planning are essential for overcoming these challenges and driving future growth.

Ken interviews Co-Founders of Negative, Marissa Vosper and Lauren Schwab.Lauren Schwab co-founded Negative in 2014 alongside Marissa Vosper with no experience in the fashion and manufacturing industry. With a passionate belief that women deserved to love the garments closest to their skin, Lauren taught herself every stage of developing, fitting and producing beautiful and functional intimate apparel. Prior to Negative, Lauren started her career in finance, working at two globally recognized investment management firms. Lauren was selected as one of WWD's 40 Under 40 list of industry notables who are changing the face of retail, fashion and the beauty industry. She graduated from the University of Pennsylvania with degrees in Art History and Diplomatic History. When she isn't working on Negative, she loves spending time with her husband and 3 little kids.Marissa Vosper was born and raised in Boulder, CO. She attended the University of Pennsylvania, earning degrees in Political Science and Spanish Language. After establishing her early career in branding, she co-founded Negative in 2014 alongside Lauren Schwab. Within the company, Marissa is focused on all aspects of brand strategy, communications, marketing, web and customer experience. Prior to Negative, she worked at two large branding agencies for a variety of clients, including Fortune 500 corporations, fashion labels, luxury brands and start-up businesses. She was honored as part of the Forbes 30 Under 30 List of Entrepreneurs for Art & Style. Marissa currently resides in New York City with her husband and 3 sons.Key takeaways from this episode include:1.    Inspiration Behind Negative Underwear: Marissa and Lauren were inspired to start Negative Underwear after recognizing a gap in the market for high-quality, minimalist lingerie. Dissatisfied with the options available, they embarked on a four-year journey from concept to launch, conducting market research and product development while maintaining full-time jobs.2.    Differentiation in the Market: Negative Underwear aimed to distinguish itself by offering a product that combined high-quality raw materials sourced from European heritage mills with an accessible price point through a direct-to-consumer model. The founders identified a lack of options between luxurious, but expensive, brands and mass-market, poorly made options, positioning Negative Underwear in a unique space.3.    Strategic Naming and Branding: The name "Negative" was chosen to reflect the brand's commitment to minimalism and a direct, provocative appeal. The founders wanted to stand out from other lingerie brands that often had French or girly names. The name embodied their vision of creating a straightforward, American brand that challenged existing norms in the lingerie market.4.    Self-Funding and Growth Philosophy: Negative Underwear has achieved substantial growth without external funding. Marissa and Lauren emphasize the importance of sustainable and thoughtful growth, drawing parallels to iconic brands that built their success over time. They prioritize making a superior product and focus on creating brand allegiance through a methodical and customer-centric approach.5.    Future Growth Opportunities: While the brand has primarily focused on direct-to-consumer sales, the founders acknowledge the potential for growth in various channels, including wholesale, retail, and even exploring platforms like Amazon. Despite having experimented with pop-ups and partnerships in the past, their lean approach allows themto adapt quickly to new opportunities, leaving the door open for potential expansion.6.    Lean Team and Profitability: Negative has maintained a lean team with around 15 full-time employees, emphasizing a disciplined and profitable approach. This focus on profitability over top-line growth sets them apart from the trend of driving top-line without regard to the bottom line that was prevalent in the past.7.    Resourceful Use of Freelance Talent: Negative became proficient in working with freelance talent due to resource constraints in the early years. This flexibility in utilizing fractional roles and determining when a role merits full-time hiring has contributed to their success in doing more with less.8.    Product-Centric Marketing: The co-founders believe in the product being the best form of marketing. They emphasize creating an exceptional product that outperforms existing options, leading to word-of-mouth growth and strong customer retention. Initially focusing on press coverage, they adapted their marketing strategies as customer behavior shifted to online platforms, particularly social media.9.    Strategic Growth Initiatives: Negative initially engaged in old-fashioned methods like trunk shows, leveraging personal networks to get hands-on interaction with potential customers. They stress the value of building a customer base before heavily investing in paid advertising. Collaborations with like-minded brands, influencers, or celebrities are considered when they can tell a unique story to a potential audience.10. Challenges and Lessons Learned: Challenges include finding new profitable channels for customer acquisition, maintaining the brand's core specialness while expanding, and dealing with price competition in the market. Key lessons learned include the difficulty of manufacturing in the intimates sector, the importance of realistic growth expectations when working with partners, and the value of adapting to new challenges while staying true to the brand's identity.

Ken interviews Jeanne Jackson for this Flight of The Retail Pilot.Jeanne P. Jackson is CEO of a private equity and consulting firm that she founded in 2002, MSP Capital. In 2018, she retired from Nike, Inc. after 16 years, serving first as a Board member for 7 years, then stepping into successive roles inside the Company as President, then Senior Advisor to the CEO. She recently retired from the Board of Directors of McDonalds, Inc., where she served since 1999, holding positions as Chair of the Compensation Committee, Chair of the Finance Committee, and member of the Governance Committee. She also recently retired from the Board of Kraft-Heinz, Inc., having served with Kraft Inc., since 2012, through the sale to a Warren Buffett/3G led Heinz, and staying with the combined Kraft Heinz entity until her retirement in May. She served on the Audit Committee and the Corporate Governance Committee. She serves currently as Director for Monster Beverages, Inc., and Delta Airlines,Inc., on both Finance and the People and Compensation Committees. In the past, Ms. Jackson has also served on the Boards of Nordstrom, Inc., Nike, Inc., Harrah’s Inc., Motorola Mobility Inc. (through its sale to Google), Williams-Sonoma, Inc., CRS Inc., and West Marine, Inc. Ms. Jackson has previously served as the Chief Executive Officer and President of Wal-Mart.com USA, LLC , President and Chief Executive Officer of Banana Republic, a Division of Gap, Inc., while simultaneously as President and Chief Executive Officer for Gap Inc.’s Direct division. Prior to Gap, Inc., Ms. Jackson held various retail and consumer Brand management positions with Victoria’s Secret, The Walt Disney Company, Saks Fifth Avenue, and Federated Department Stores.Ms. Jackson has served on the Board of Advisors of the Harvard Graduate School of Business, and University of California, Irvine Merage School of Business. She is the Past President of the United States Ski and Snowboard Foundation Board of Trustees, and served on numerous Community Boards. She is currently a member of the International Women's Forum of Las Vegas, and has, in the past, been recognized by Business Week as “One of the Year’s 25 Best Managers,” by Fortune as one of “The Most Powerful Women in Business,” and by Ad Age as one of “The Most Powerful Women in Sports.” Ms. Jackson holds a BS from the University of Colorado, and an MBA from Harvard’s Graduate School of Business Administration.Key takeaways from the podcast highlight Jeanne Jackson's impactful career in retail, showcasing her leadership skills, strategic thinking, and contributions to transforming and growing iconic brands.1.    Transformation of Banana Republic: Jeanne Jackson reflects on her leadership at Banana Republic, where she took the brand from being perceived as a stepchild to becoming a formidable brand within the Gap portfolio. This transformation involved assembling a high-quality team and pushing against opposition to lead the brand into the e-commerce space.2.    Transition to Retail Career: Jeanne's journey into retail wasn't initially planned. She had intended to enter the consumer packaged goods industry but was convinced by someone in the retail sector, Frank Arnone, to explore a career in retail. This encounter shifted her trajectory, leading her to successful roles at various retail companies.3.    Learning and Leadership Development: Jeanne attributes her leadership skills to lifelong learning and accumulating experiences. From her early exposure to extemporaneous speaking in high school to her experiences in business school, including the Harvard Business School method's case study approach, she developed the ability to assimilate data quickly and make decisions convincingly.4.    Selecting Board Positions: Jeanne shares her approach to selecting board positions, emphasizing a deep understanding and passion for the brand. She believes in contributing meaningfully to the boards she joins, bringing strategic thinking, leadership, and a clear path to impact. She emphasizes the importance of diversity in the boardroom.5.    Career Highlights at Banana Republic and Nike: Jeanne expresses pride in her work at Banana Republic and Nike. At Banana Republic, she played a crucial role in turning the brand into a significant player within the Gap portfolio and was an early advocate for embracing e-commerce. Her time at Nike involved joining the company's board and later leading the direct-to-consumer business, significantly impacting the company's trajectoryin that space.6.    Consumer Focus from Disney: Jeanne Jackson highlights the importance of consumer focus, a core competency she developed during her time at Disney. The strategic work at Disney emphasized understanding how consumers felt about the brand, their interactions, and motivations. This consumer-centric approach became foundational in her subsequent roles at companies like Victoria's Secret, Banana Republic, and Nike.7.    E-commerce Motivation: Jeanne Jackson explains the motivation behind embracing e-commerce during her time at Nike. She observed the high consumer demand in San Francisco, attributed to the availability of broadband. Recognizing that consumers would want to buy products online, the decision was made to meet consumers where they were and be ready for a broader audience as broadband adoption increased nationwide.8.    Technology as a Base Level: According to Jackson, technology is a crucial aspect of any business strategy, especially in the realm of e-commerce. She emphasizes that technology is a baseline requirement for running a successful e-commerce business, covering aspects like quick checkout, easy navigation, and efficient inventory management.9.    AI in Retail: Jeanne Jackson acknowledges the significance of artificial intelligence (AI) in retail. She anticipates that AI will bring another level of capability to the retail industry, and those who neglect its integration may miss out on valuable opportunities. The discussion also touches on the potential impact of AI on job roles, with Jackson suggesting that while some roles may be replaced, there could be opportunities for higher efficiency and smarter use of human resources.10. Evolution of Retail: The conversation delves into the evolving landscape of retail, with a focus on digitally native brands. Jackson expresses excitement about these brands that have captured consumer attention, especially those that emerged or gained momentum during the pandemic. The discussion highlights the changing strategies of brands, including considerations of omni-channel approaches and the exploration of various channels to reach customers, even mentioning the challenges and uncertainties associated with selling on platforms like Amazon.

Ken interviews Chris Riccobono, Co-Founder and Executive Chairman of Untuckit., one of the fastest-growing men’s retail brands in the U.S.After earning his Bachelor’s degree from Providence College in 2001, Chris began his career at GE Healthcare and enrolled in Columbia Business School in 2007. While working towards his MBA, Chris thought of the idea for UNTUCKit after speaking with lots of men about their fit problems—especially the length of their collared shirts—and began the business from his apartment in Hoboken. It began as just a side job, but once Chris and his early customers realized that he’d solved a big problem in men’s fashion, the business quickly grew beyond his expectations—with a compound annual growth rate over 100% each year—into the brand we know today with more than 50 retail locations by the end of 2018 and an entrance into the international market.In addition to furthering his education and growing the brand, Chris dedicated time to sharing his passion for wine through a video blog called Pardon That Vine, traveling the world interviewing winemakers, and teaching beginners about wine. Chris was a winner of the Entrepreneur Of The Year® 2018 Award in New York and in his spare time he works closely with the Cancer Center at Atlantic Health System in New Jersey.Chris currently lives in New Jersey with his wife and children.Untuckit's Origin and Chris Riccobono's Journey: Chris Riccobono, the co-founder of Untuckit, started the company with the idea of creating a shirt designed to be worn untucked, addressing a common problem in men's fashion. The concept emerged from Chris's frustration with traditional shirts being too long, and he decided to venture into the fashion industry despite having no prior experience in the field.Struggles and Early Challenges: Untuckit faced initial challenges, including the difficulty of finding the right shirt length and manufacturing issues. They encountered setbacks like shirts shrinking and buttons unraveling. Chris and his partner struggled to make a quality product and initially had limited resources, raising a modest amount of money to launch the brand.Marketing Strategies and Growth: Untuckit adopted unconventional marketing strategies, such as radio ads and airline ads, to promote their unique product. The tagline "shirts designed to be worn untucked" resonated well with the audience. Despite the slow initial growth, Untuckit's brand strength and customer satisfaction led to significant success, with a focus on brick-and-mortar stores alongside online presence.Impact of the COVID-19 Pandemic: The podcast covers the unexpected challenges Untuckit faced during the COVID-19 pandemic. The company went from a position of rapid growth to considering bankruptcy within a few months. Chris highlights the importance of resilience and adaptability in overcoming the challenges posed by the pandemic, which significantly impacted the fashion industry.Current and Future Plans: Despite the challenges, Untuckit managed to survive and adapt. Chris discusses their recovery strategy, including negotiating with landlords and factories, raising debt, and ultimately becoming profitable again. Untuckit is optimistic about the future, planning to open 20-25 stores, exploring international markets, and diversifying into wholesale. The company aims to continue its growth trajectory and capitalize on its brand strength.Efficient Store Strategy: Chris emphasizes the importance of efficient store design and operations. He prefers stores in the range of 1,200 to 1,500 square feet, with a focus on cost-effective buildouts. The goal is to provide a productive and efficient shopping experience.Move Away from Large, Expensive Stores: Chris challenges the traditional approach of large, aesthetically pleasing stores, citing the inefficiency and high costs associated with them. He believes in smaller, more cost-effective stores that prioritize customer experience and efficiency.Acquiring Customers Through Stores: Chris sees brick-and-mortar stores as crucial for acquiring customers and marketing. He views them as billboards and advocates for cost-effective store openings, even if they generate less revenue per store.Brand Ambassadors for Credibility: Discussing marketing strategies, Chris highlights the use of brand ambassadors for credibility, even though he acknowledges the challenges in directly measuring their impact. He mentions having ambassadors like Drew Brees and Wayne Gretzky, who were also investors in the brand.Importance of Brick-and-Mortar Despite E-commerce: Contrary to the belief that brick-and-mortar retail is diminishing, Chris argues that it remains an essential and enduring part of the shopping experience for the majority of people. He believes in thecontinued importance of physical stores for various activities and social interactions.Changes in Raising Capital: Chris mentions that the landscape for raising capital has changed, especially post-COVID. Investors are now more cautious and won't engage unless a company is profitable. The era of overvaluing companies without profitability seems to be over, and investors are looking for sustainable business models.Challenges for New Companies: According to Chris, it's currently challenging for new companies, especially pre-revenue ones, to raise money. The competitive environment and caution among investors make it difficult for new brands to secure funding. He emphasizes the importance of having a strong brand and being cautious with spending.Lessons Learned and Advice: Chris reflects on lessons learned from his entrepreneurial journey. He advises being more relaxed and enjoying the challenges. Additionally, he stresses the importance of discipline in spending, citing examples from Untuck It where they were frugal and avoided overspending. Chris also highlights the significance of preserving capital and finding ways to hang around, emphasizing the long-term game for success.