S5E8: Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, Is Sharing Her Experience With New Founders as the Co-Founder and Managing Partner of Clerisy

In The Room with Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, GLAMSQUAD, and Clerisy. 

In our final episode of the season, and 50th episode of The Room Podcast, Alexandra shares her experience breaking into the online retail fashion world with her smash hit, Gilt Groupe, alongside her partner, Alexis Maybank. Alexandra explains how she had limited merchandising experience but took advantage of the consumer ‘FOMO’ by creating the early forms of fashion brand “drops.” 

In this conversation, we cover themes such as the original “drop” model, what’s happening in Miami’s ‘Silicon Valley Beach’, and the adoption of Omni-channel 3.0.

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4:23 - Where did Alexandra grow up and how did that experience shape her view of the World?
5:55 - Did Alexandra always think she would become a founder?
7:35 - When Alexandra was at Harvard, were many people looking to become founders?
10:03 - What was the retail climate like in 2007 when Alexandra started Gilt Groupe?
13:05 - Did Alexandra realize she was creating the early stages of fashion brand “drops”?
14:24 - What inspired Alexandra to structure Gilt Groupe in the way that it was?
15:13 - Was it difficult pursuing larger purchase orders without having much retail fashion experience?
18:32 - Who's the first person to say yes to Alexandra and Gilt Groupe?
20:39 - What challenges did Alexandra face when building the robust catalog of items on Gilt?
25:31 - Is Alexandra more or less bullish on the gig economy than she was when she founded Glamsquad in 2014?
26:56 - What is the investment strategy of Clerisy?
29:44 - How is the technology ecosystem evolving in Alexandra’s new home city of Miami?
32:07 - What do the next five years hold for commerce?
33:54 - How is Alexandra thinking about the evolving tech world, especially in regard to Web3?
36:38 - Who is a woman in Alexandra’s life that had a profound impact on her and her career?

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Season 5 of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.

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