The Retail Pilot

From Gilt to Glamsquad: Alexandra Wilkis Wilson’s Journey Building Unicorns and Investing in Talent

Aug 20, 2024

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.

47:58

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Alexandra Wilkis Wilson

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Quick takeaways

Alexandra Wilkis Wilson's entrepreneurial journey showcases the impact of innovative business models like Gilt's exclusive timed sales on consumer engagement.

The establishment of Clerisy highlights an investment strategy focused on solving unique consumer problems while emphasizing hands-on support for growth.

Deep dives

Entrepreneurial Origins and Early Career

The journey into entrepreneurship often stems from early interests and experiences, as illustrated by one individual who showed entrepreneurial spirit from a young age. Growing up in New York City, this person fondly recalls organizing a lemonade stand as a child, which laid the groundwork for their later successes. After a stint in investment banking, they transitioned into the retail world, choosing to work for Louis Vuitton over Zara, indicating a clear preference for the luxury sector. This decision, followed by a management training program, set the stage for their entrance into entrepreneurship, culminating in the establishment of Gilt in 2007.

Intro

2min

From Luxury to Innovation: A Journey Through Entrepreneurship

25min

Launching a Growth Equity Fund Amidst Change

4min

Investing in Innovation: A Deep Dive

8min

Lessons in Leadership and the Impact of Mentorship

4min

Reflections on Career Opportunities and Lessons Learned

2min

Rapid Fire Insights: Personal Favorites and Career Aspirations

2min

Ken Pilot interviews Alexandra Wilkis Wilson for this episode of The Retail Pilot podcast.

Alexandra is an ENTREPRENEUR, INVESTOR & BOARD DIRECTOR.

She is best known as Co-Founder of ecommerce sensation, Gilt, which grew to $650M+ within 5 years of its launch and later sold to Hudson’s Bay Corporation. She was also Co-Founder of GLAMSQUAD, and Fitz, a closet organizing and styling company, which sold to Tradesy the peer-to-peer luxury recommerce company.

Today, Alexandra is Co-Founder and Managing Partner of growth equity fund, Clerisy, investing in consumer and techsumer companies. She has been an avid angel investor and advisor to over 80 consumer tech companies including Rent the Runway, The Mirror and Bubble. Alexandra is an active champion of female founders and the co-author of New York Times bestseller, “By Invitation Only: How We Built Gilt and Changed the Way Millions Shop”.

Summary

Alexandra discusses her entrepreneurial journey, starting with her time at Gilt and later founding Glamsquad. She shares the challenges and successes of both ventures and the lessons she learned along the way. She also talks about her involvement in other startups and her decision to join Clerisy, a growth equity fund. Alexandra discusses her career journey, the founding of Clerisy Partners, and their investment strategy. She highlights the importance of understanding consumer needs and solving problems in a unique way. Wilson emphasizes the hands-on approach of Clerisy Partners, where they actively partner with portfolio companies and provide support beyond capital. She also shares her leadership philosophy, the influence of mentor Mindy Grossman.

Takeaways

Alexandra Wilkis Wilson had an entrepreneurial spirit from a young age and pursued a career in investment banking before venturing into the world of retail and entrepreneurship.

Gilt, founded in 2007, grew rapidly and became a successful online luxury fashion retailer, attracting a large customer base with its timed sales and curated assortments.

Glam Squad, founded by Alexandra Wilkis Wilson, offered in-home beauty services and expanded to multiple markets, providing a hyper-local experience.

Alexandra Wilkis Wilson applied the lessons learned from Gilt to Glam Squad, including managing people, motivating teams, and giving and receiving feedback.

She later worked on other ventures, including Dressr, an app that used AI and machine learning to help users style outfits, and FITS, a service that organized consumers' closets and provided styling recommendations.

Alexandra Wilkis Wilson joined Clerisy, a growth equity fund, to continue her involvement in the tech and consumer-focused industry. Understanding consumer needs and solving problems in a unique way is key to successful investments.

Clerisy Partners takes a hands-on approach and actively partners with portfolio companies.

Delivering tough messages and providing constructive feedback is important for effective leadership.

Mindy Grossman has been a mentor and role model for Alexandra Wilkis Wilson.

Favorite streaming shows include El Tiempo Entre Costuras, Fauda, and Outlander.

Favorite vacation destinations are Key Biscayne and Brazil.

Taylor Swift is someone Alexandra Wilkis Wilson would love to meet.

Clerisy Partners aims to invest in the next unicorn among their portfolio companies.

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