In this episode of The Orita Podcast, Aaron Schwartz sits down with Jessica Lee. Jessica started Modern Citizen with a small friends and family round, never raised again, and just celebrated ten years in business. Most of the funded brands from her era are gone. She has a theory about why.

• The Gap Inc. training that most fashion founders never get: rotating through merchandising, inventory, production, and strategy before ever starting a brand

• Why she believes CAC should be positive from the first transaction, and why betting on LTV never made sense to her in apparel

• Not a workwear brand, but a brand for women who work: the psychographic positioning that has mothers and daughters shopping together

• The white blazer of April 2020 and how a sub-fifteen-person team pivoted an entire fall assortment while big retail watched inventory arrive on boats

• Sublease first, sign later: the real estate strategy that let a bootstrapped brand open stores in the two most expensive markets in America

• Her reframe that stopped Aaron mid-sentence: retention is not a metric, it is whether you are delivering on the brand promise

👥 Meet the guest

Jessica Lee, Founder and CEO at Modern Citizen

🎙 Hosted by

Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai

🎧 Chapters

[00:00] Jessica Lee: Ten Years of Modern Citizen

[00:37] The Gap Inc. Rotational Program: Learning the Business of Fashion

[03:22] From Product Functions to the Strategy Group

[06:00] Working M&A and Watching DTC Get Coined

[08:00] Something Specific for Someone: The Modern Citizen Thesis

[09:38] Building With a Business Partner and No Institutional Money

[11:54] Ten Years In, Closer to the Brand Promise Than Ever

[13:30] Psychographic Over Demographic: Mothers and Daughters Shopping Together

[15:11] Why She Never Raised: Control, Discipline, and Product Market Fit

[19:13] Coming From Retail: Knowing the Margin Structure From Day One

[20:51] CAC Positive From the First Transaction

[21:28] Two Years of Word of Mouth, Then the First Marketing Budget

[23:52] Consistency Is the Superpower: We Thought You Were Huge

[26:04] The First Thousand-Unit Bet and Learning to Take Risks

[29:46] One Big Bet at a Time: Managing Founder Energy Through Four Kids

[31:19] COVID: The White Blazer That Never Had a Chance

[33:43] Showrooms, Subleases, and Re-Entering Stores in 2024

[37:57] Retention Is Whether You Deliver on the Brand Promise

[40:25] Claude, Chat Walrus, and Freeing a Small Team From Admin Work

🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when.

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