The Retail Pilot

In this engaging chat with Alexandra Wilkis Wilson, co-founder of Gilt and GLAMSQUAD, listeners dive into her dynamic entrepreneurial journey. She shares the rapid rise of Gilt and the innovative leap into GLAMSQUAD, highlighting lessons from challenges and successes. Alexandra discusses her transition to investing through Clerisy, focusing on consumer needs and unique problem-solving. With a commitment to mentoring female founders, she emphasizes the importance of personal connections and inclusive leadership in shaping successful ventures.

In this engaging discussion, Joe Yakuel, Co-Founder & CEO of brkfst.io, is joined by industry leaders Soumya Sriraman, a veteran CEO in streaming businesses, and Stephen Simonis, a strategic advisor. They delve into how brkfst.io empowers brands to create authentic user-generated content quickly. The conversation covers the challenges of shoppable video content, effective UGC strategies, and the vital role of storytelling in modern marketing. They stress the importance of leveraging diverse content across platforms to elevate customer engagement and conversion.

Tim Parr, CEO and Founder of CADDIS, is on a mission to redefine aging through eyewear. He critiques the eyewear market for neglecting those over 40 and shares personal experiences on embracing age rather than shunning it. Tim discusses the economic power of the 50+ demographic and innovative marketing strategies, including storytelling and in-person engagement. He reflects on his journey from bluegrass musician to entrepreneur, emphasizing authenticity in branding. Plus, he highlights the importance of mentorship in fostering creativity within business.

Ken Pilot interviews Janet Hayes, CEO of Crate & Barrel Holdings, for this episode of The Retail Pilot podcast.SummaryJanet Hayes, CEO of Crate and Barrel Holdings, shares her journey into retail and her experience leading the company. Crate and Barrel Holdings is a multi-brand, multi-platform, multi-country company with four brands: Crate and Barrel, CB2, Crate and Kids, and Hudson Grace. Hayes discusses the strategy behind physical retail and the importance of providing exceptional shopping experiences. She emphasizes the need to inspire customers and make the buying process easier, especially in the home furnishings industry. Hayes also highlights the investment in store design, technology, and employee training to enhance the customer experience. Crate and Barrel has been addressing tech debt and selectively replacing technology to improve the customer experience. The company has a comprehensive strategy that includes technology, process, and culture changes. The leadership team consists of both tenured individuals and new hires, bringing a balance of experience and innovation. Crate and Barrel is focused on international growth, particularly in Europe and Canada. The company is preparing for the future of home decor by considering the impact of AI and maintaining a focus on quality and sustainability. Collaborations with influential partners have been successful in keeping the brands fresh. The marketing strategy is shifting towards digital and personalized content. Janet Hayes is motivated by the commitment to customers and employees, and she enjoys the energy and growth of the retail industry.TakeawaysJanet Hayes has over 30 years of experience in retail and has worked for companies like Macy's, Gap, Nike, and Williams Sonoma before joining Crate and Barrel Holdings as CEO.Crate and Barrel Holdings is a multi-brand company with four brands: Crate and Barrel, CB2, Crate and Kids, and Hudson Grace.The strategy behind physical retail for Crate and Barrel Holdings is to provide exceptional shopping experiences and inspire customers.Investments have been made in store design, technology, and employee training to enhance the customer experience.Crate and Barrel Holdings is focused on market share and has gained significant market share in the home furnishings industry.The company is investing in a new POS system that will enable associates to take transactions wherever the customer is, providing a seamless and convenient shopping experience. Crate and Barrel is addressing tech debt and selectively replacing technology to improve the customer experience.The company has a comprehensive strategy that includes technology, process, and culture changes.The leadership team consists of both tenured individuals and new hires, bringing a balance of experience and innovation.Crate and Barrel is focused on international growth, particularly in Europe and Canada.The company is preparing for the future of home decor by considering the impact of AI and maintaining a focus on quality and sustainability.Collaborations with influential partners have been successful in keeping the brands fresh.The marketing strategy is shifting towards digital and personalized content.Janet Hayes is motivated by the commitment to customers and employees, and she enjoys the energy and growth of the retail industry.Chapters00:00Introduction and Janet Hayes' Journey into Retail08:23Taking on the Role of CEO at Crate and Barrel Holdings11:24The Strategy Behind Physical Retail at Crate and Barrel Holdings18:57Investing in Exceptional Shopping Experiences23:15Enhancing the Customer Experience with...Hosted by Ausha. See ausha.co/privacy-policy for more information.

Enjoy a replay of this beloved episode of The Retail Pilot podcast.In this episode, Ken sits down with Ryan Babenzien, the brilliant mind behind Greats, a renowned footwear brand that has taken the industry by storm. But today, Ryan is here to share his latest venture: Jolie, a groundbreaking showerhead filter brand.Join Ken as he delves into Ryan's entrepreneurial journey, from building a successful sneaker empire to tackling a new frontier in personal care.Discover the inspiration behind Jolie and how Ryan's passion for sustainability and wellness led him to revolutionize the way we experience showers.Key Takeaways from this podcast include:· Career Path and Transition to Retail: Ryan initially studied economics and considered a career in finance but pivoted to entertainment, eventually transitioning to retail. His experience in entertainment, where he represented celebrity talent and advised brands on product placement, honed his marketing skills and influenced his later ventures in retail and brand building.· Founding Greats and Its Success: Babenzian founded Greats, the first digitally native footwear brand, in 2014. His knowledge of footwear and the direct-to-consumer (D2C) model contributed to its rapid success. Greats was sold to Steve Madden in 2019. This venture taught him valuable lessons in brand building and the challenges of online businesses involving products with sizing.· Jolie Skin Co's Innovative Approach: Inspired by the inefficiencies he observed with products that have sizing, Babenzian founded Jolie Skin Co, focusing on water purity for better skin, hair, and well-being. Jolie offers a subscription-based model with a showerhead that includes a filter to purify water, addressing contaminants that can harm skin and hair.· Marketing and Growth Strategy: Jolie's growth strategy heavily relies on user-generated content (UGC) and organic marketing. Instead of spending heavily on paid advertising, they focused on influencer marketing at a micro level, leading to 5,000 pieces of UGC in their first year. This grassroots approach has been pivotal in creating a strong community and driving efficient, profitable growth.· Efficient Business Model and Future Outlook: Jolie became profitable within six months, aided by its subscription model and low churn rate. With a small team of three full-time employees and several contract partners, they have efficiently scaled the business, projecting significant growth. Babenzian aims for a strategic exit within 36 months, building on the lessons from his first entrepreneurial venture and maintaining a clear focus on profitability and sustainable growth.· Importance of Multi-Channel Distribution: Ryan emphasizes that relying solely on direct-to-consumer (D2C) sales is not sustainable due to the high costs of digital marketing. He advocates for a diverse retail strategy, which includes being in various retail channels and marketplaces like hair salons, Goop, Erewhon, Home Depot, and Target. This diversified approach helps in maintaining profitability and reaching a broader customer base.· Direct-to-Consumer Still Dominates: Despite the emphasis on multi-channel distribution, over 90% of Jolie's business remains direct-to-consumer. This channel is profitable from the first purchase, highlighting its importance to the company. Additionally, 15% of their top line comes from Amazon, showcasing the significance of leveraging well-established digital marketplaces.· Potential Retail Expansion: Ryan mentions the possibility of Jolie opening its own retail stores in the future, with innovative concepts like high-tech vending machines and small, productive retail spaces. This would enhance brand presence and provide customers with a unique shopping...

Ken Pilot interviews Sid and Ann Mashburn, Founders of Sid Mashburn and Ann Mashburn, for this episode of The Retail Pilot Podcast.Sid Mashburn grew up in small-town Mississippi but began his design career in New York in the mid-1980s, as J.Crew’s first men’s designer. He designed the brand’s first heritage piece— the Barn Jacket. He was later recruited by Ralph Lauren to join the design team at Polo, and after subsequent stints leading design at Tommy Hilfiger and Lands’ End, it was time to do his own thing. His wife, Ann Mashburn had been on the editorial side of fashion, working in magazines at Condé Nast (Vogue, Glamour) and then as a stylist at J.Crew. Since meeting in their early 20s, they’d known that whether it was making mix tapes or throwing parties, what they really loved wasn’t just creating things, but sharing them with others.SummarySid and Anne Mashburn discuss their journey in building their retail business, which includes six stores and an online presence. They emphasize the importance of creating a unique and personalized shopping experience for their customers, with a focus on customer service and curated merchandise. They also talk about the challenges they faced in launching their business and the decision to expand into online sales. The conversation touches on the significance of the tailor shop in their stores and the success of their made-to-measure business.Ann Mashburn discusses the importance of the experience and memory associated with buying and wearing clothing. She emphasizes the value of made-to-measure clothing and the attention to detail it requires. Ann also talks about the role of marketing in reaching customers and reinforcing the brand. She mentions the use of digital marketing and email campaigns as effective strategies.Ann and Sid Mashburn discuss the challenges and benefits of working together as a married couple. They highlight the importance of trust and the support they provide each other. They also mention their mentors and the inspiration they draw from different designers and places. Ann and Sid share their vision for the future of their business, including expanding to more cities and growing their e-commerce presence. They emphasize the importance of creating special experiences for every customer and maintaining a sense of restraint in their growth. Finally, they discuss the value of personal connections and relationships in their industry.Takeaways·     Creating a unique and personalized shopping experience is key to building a successful retail business.·     Customer service and curated merchandise are important factors in attracting and retaining customers.·     Expanding into online sales can be a significant growth opportunity for brick-and-mortar retailers.·     The tailor shop adds a bespoke element to the store and enhances the overall customer experience.·     The made-to-measure business allows for a deeper level of customer engagement and satisfaction. The experience and memory associated with buying and wearing clothing can be just as important as the clothing itself.·     Made-to-measure clothing offers a personalized and high-quality experience for customers.·     Digital marketing and email campaigns are effective strategies for reaching and engaging customers.·     Working together as a married couple requires trust and support.·     Mentors and relationships with industry professionals can provide valuable advice and guidance.·     Creating special experiences for every customer is a key focus for the business.·     Maintaining a sense of restraint and thoughtful growth is important for long-term success.·     Personal connections and relationships are highly valued in the industry.Chapters00:00...

Ken Pilot interviews Mindy Grossman, a return guest to The Retail Pilot Podcast.Mindy Grossman is a Partner and Vice Chair at Consello, a financial services advisory and strategic investing platform.Prior to Consello, Mindy joined Weight Watchers in 2017 as the CEO and President leading the repositioning and rebranding of the company to WW Intl. From 2008 to 2017 Mindy took IAC retail public and then became CEO of HSN, a $4B DTC business. Earlier in her career, Mindy had key Leadership roles with Nike, Ralph Lauren, Warnaco, Tommy Hilfiger and and Oxford industries.Mindy has been recognized and awarded numerous times over her career including Forbes Magazine’s The 100 Most Powerful Women, an Advisory role on President Obama’s Digital Economy board as well as serving as chairman of the NRF.Mindy currently is an investor in and on The Board of Directors of Herself Health and Fanatics, Inc., VF, American Heart Association and HungryRoot.SummaryMindy Grossman discusses the diverse services provided by the company and the role her team plays with major companies. She highlights the importance of customization and collaboration in their advisory practices. Mindy also talks about the investments made by Consello Capital in tech-enabled services and consumer retail. She emphasizes the power of storytelling in business and the need for brands to create authentic and engaging experiences for customers. Mindy shares her passion for education and her involvement in various non-profit organizations. She reflects on her favorite moments in her professional career, including starting a business, leading the apparel business at Nike, and her time at HSNI.Takeaways·     Consello provides a diverse range of advisory and investment services to major companies, with a focus on customization and collaboration.·     Investments made by Consello Capital are centered around tech-enabled services and consumer retail.·     Storytelling is a powerful tool in business, allowing brands to create authentic and engaging experiences for customers.·     Mindy Grossman is passionate about education and is involved in various non-profit organizations.·     Her favorite moments in her professional career include starting a business, leading the apparel business at Nike, and her time at HSNI.Chapters00:00Introduction and Overview of Consello Group03:10Customized Advisory and Investment Services09:53Investments in Tech-Enabled Services and Consumer Retail13:07The Power of Storytelling in Business23:57Favorite Moments in Mindy Grossman's Professional CareerHosted by Ausha. See ausha.co/privacy-policy for more information.

Join Host Ken Pilot for an Exclusive Interview with Steve Madden: The Visionary Behind the Iconic Footwear and Accessories BrandKey Highlights:Steve Madden's Early Career Steve Madden's journey in retail began at a shoe store in Cedarhurst, Long Island. By leveraging his connection as Johnny Madden's little brother, he secured a job that marked the start of his illustrious career in the shoe business.Creative Influence in the Shoe Business During the mid-'70s, Steve worked in an era marked by creative trends, especially in men's footwear like platform shoes. Inspired by the store owner who fancied himself a shoe designer, Steve's passion for the creative side of the shoe business blossomed.Mentorship at Gildor At Gildor, a renowned shoe retailer, Steve found a mentor in Larry, the owner's son. Larry's emphasis on perfect displays and attention to detail profoundly influenced Steve's approach to business.The Influence of Sobriety Steve credits his sobriety as a pivotal factor in his success. Getting sober allowed him to focus and make better business decisions, ultimately driving his achievements.Impact of Jordan Belfort Steve's association with Jordan Belfort, the infamous "Wolf of Wall Street," had mixed consequences. While Jordan's entrepreneurial spirit encouraged Steve, their financial dealings led to legal troubles and Steve's imprisonment. Despite this, Steve acknowledges Jordan's impact on his journey.Appreciation for Teamwork Steve highlights the importance of a strong team, crediting his success to the people around him. His childhood friend, Jamie Carson, played a crucial role as CEO during Steve's absence, protecting the company during challenging times.International Business Steve's brother, John Madden, significantly contributed to the international expansion of Steve Madden. John's charm and relationship-building skills complemented Steve's hands-on business approach. Today, the brand operates in approximately 50 countries, advocating for international trade as a means to foster mutual understanding and peace.The Steve Madden Group The Steve Madden Group owns several notable brands, including Betsey Johnson, Dolce Vita, BB Dakota, Big Buddha, Blondo, and Greats. Steve Madden remains open to further acquisitions, particularly in the apparel sector, with a focus on good management and innovative ideas.Steve Madden: The Man Behind the Brand Steve Madden is an award-winning designer and entrepreneur whose company is valued at over $3 billion. Despite facing significant challenges, including addiction and legal troubles, he has built a global empire through resilience and creativity.In 1990, with just $1,100, Madden launched his brand, anticipating consumer needs and delivering cutting-edge collections. His Queens-based factory quickly transformed his dream into reality, giving birth to the Steve Madden brand.Today, with over 200 stores worldwide, numerous brand acquisitions, and collaborations with stars like Sydney Sweeney, Cardi B, and Kendall and Kylie Jenner, Steve Madden continues to innovate and lead the industry.Steve's humble beginnings and the support he received are never far from his mind. As a recovering addict and someone managing ADD, he actively supports organizations that offer second chances.A native New Yorker, Steve resides in Manhattan with his children and remains deeply involved in his company's operations, from Long Island City headquarters to showrooms and stores worldwide.Don't miss this insightful conversation with Steve Madden, an entrepreneurial icon who turned a small investment into a global powerhouse, inspiring millions with his creativity, resilience, and dedication.Hosted by Ausha. See ausha.co/privacy-policy for more information.

In this engaging conversation, Scott Tannen, the visionary Founder and CEO of Boll & Branch, shares insights from his journey in redefining the luxury bedding industry. He discusses sustainable practices and innovative strategies that helped propel his brand to success without heavy reliance on venture capital. Discover how Boll & Branch fosters customer loyalty through transparency and unique collaborations, like a stunning gown for the Met Gala. Tannen also reflects on his rich background in digital marketing, bringing valuable lessons from consumer goods into the bedding world.

Ken Pilot speaks with Ramy Brook Sharp one year later on The Retail Pilot podcast. Ramy is the Founder and CEO of eponymous brand, Ramy Brook.In this conversation, Ken and Ramy discuss the current state of Ramy Brook, a fashion brand, and the strategies they are implementing to grow the business. They talk about the balance between wholesale and e-commerce, successful collaborations, marketing tactics, and the use of technology like AI in the fashion industry. In this part of the conversation, Ramy Brook Sharp discusses the use of AI technology in the fashion industry, the growth and future plans for Ramy Brook, and the potential for expansion into new product categories and markets. She also talks about the importance of the team and the role of her husband in the financial aspect of the business. The conversation concludes with a rapid-fire round of questions.Takeaways·     Ramy Brook is a fashion brand known for its sexy, silky tops and contemporary price point.·     The company has a balanced approach to sales, with about 50% of revenue coming from wholesale and 50% from e-commerce.·     Successful collaborations with jewelry designers, shoe brands, and activewear companies have helped expand Ramy Brook's product offerings and reach new customers.·     Marketing efforts focus on social media platforms like Facebook and Instagram, as well as influencer partnerships and traditional digital marketing.·     The use of AI technology, such as Raspberry AI, is being explored to improve design iterations and speed up the production process. AI technology can save time and improve the process in the fashion industry, particularly in areas like photo shoots and design decisions.·     Ramy Brook is focused on slow and steady growth, with plans to expand the team in design and sales.·     The brand is exploring new product categories such as jewelry and accessories.·     International expansion is a key area of growth for Ramy Brook.·     The company is considering opening brick-and-mortar stores in strategic locations.·     Ramy Brook admires designers Donna Karan and Diane von Furstenberg and would like to meet Taylor Swift. Chapters00:00Introduction and Catching Up02:47The Growth of Ramy Brook: From Sexy Tops to a Full Collection06:15Balancing Wholesale and E-commerce: Ramy Brook's Sales Strategy10:24Successful Collaborations: Expanding Ramy Brook's Product Offerings15:06Marketing Tactics: Social Media, Influencers, and Digital Advertising26:17The Impact of AI Technology in the Fashion Industry28:13Growth and Future Plans for Ramy Brook31:43Exploring New Product Categories and Markets37:12The Importance of the Team and Financial Oversight38:21Potential Expansion into Brick-and-Mortar Stores42:23Rapid-Fire Round: Celebrity Guests, Favorite Designers, and MoreHosted by Ausha. See ausha.co/privacy-policy for more information.