004. There Is Money Hanging in Your Closet | Pickle Co-Founder Julia O’Mara on Passive Income, Peer-to-Peer Fashion Rental & Raising an $8M Round After Bootstrapping for 2 Years

Welcome to Episode 004 of STACKED — the show about becoming your own best asset. Today Emily sits down with Julia O’Mara, co-founder and COO of Pickle, the peer-to-peer fashion rental marketplace that is Airbnb for your closet. At 23, Julia left a senior product manager role at Blackstone to build a platform that lets women make passive income renting out pieces they already own. She bootstrapped for 2.5 years on $200,000, personally delivered the first 1,500 orders across New York City, ran out of money three times, and raised $12 million in seed funding before closing a Series A in March. Julia has been named to Forbes 30 Under 30 and the Inc. Female Founders List. This episode is your complete closet-to-cash playbookConnect with us:Subscribe to the STACKED newsletter - weekly headlines on Bitcoin, digital assets, business, and wellness delivered every Sunday and Wednesday. Subscribe at https://stackedassets.co/ Follow Us: YouTube: https://www.youtube.com/@stacked-assetsInstagram: https://www.instagram.com/stackedassetsTikTok: https://www.tiktok.com/@stacked.assetsFollow Emily Dempsey:Instagram: https://www.instagram.com/emilydempseyX: https://x.com/EmilyDempseyLinkedIn: https://www.linkedin.com/in/emily-j-dempsey/Follow The Brickell Babes:Become A Member: www.thebrickellbabes.com/membershipInstagram: https://www.instagram.com/thebrickellbabes/TikTok: https://www.tiktok.com/@thebrickellbabes WHAT WE COVER:— How COVID revealed that Julia was more passionate about her colleagues than her actual work, and how a conversation with her co-founder changed everything. —The first app flopped. But inside the failure was the data that became Pickle. Julia explains how to read the signal inside the mess. —The nano influencer hack, the green balloons in SoHo, Brian's apartment as a warehouse, and delivering 1,500 orders on the NYC subway. —The 10 to 20% of retail framework. A $400 dress rents for $50 to $80. Both sides win. —The Pickle Protection Policy, reviews, lender controls, and the condition reporting feature that changes the game. —How to download the app, upload your first items using AI autofill, and start earning this week. —Ship by Friday vs. perfect V1, creator seeding vs. paid ads, city by city vs. nationwide growth. TIMESTAMPS:00:00 — Welcome to STACKED00:30 — Introducing Julia O’Mara and Pickle02:30 — Julia's background and twin sister04:00 — Engineering at Penn and the entrepreneurship minor06:30 — Joining Blackstone out of college08:00 — COVID and the realization that prompted the leap09:30 — Meeting co-founder Brian and the first conversation about Pickle11:00 — Pickle Poll: the first app and why it failed14:00 — The pivot signal: comments in the polling app16:00 — Leaving Blackstone and launching the rental MVP18:00 — Bootstrapping $200K for 2.5 years20:00 — Getting the first lenders: friends' wardrobes and green balloons in SoHo23:00 — Brian's apartment as the Pickle warehouse25:00 — Delivering 1,500 orders across NYC on the subway27:00 — How 85 to 90% organic growth happened29:00 — The viral moment that unlocked the seed round31:00 — Raising $8 million in seed funding33:00 — Pricing strategy: 10 to 20% of retail35:00 — Geographic expansion: NY to LA to Miami37:00 — Growth fellowship program and next cities39:00 — Trust and safety: Pickle Protection Policy43:00 — Closing the Series A in March44:00 — Julia's COO role and weekly metrics ritual46:00 — Wellness as a founder: movement, water, something green48:00 — Closet to Cash: 3 steps to start this week51:00 — Top lenders making thousands a month53:00 — 1 in 4 women in NYC has downloaded Pickle54:00 — Lightning round56:00 — Where to find Julia and download Pickle Subscribe for new episodes every Tuesday at 7AM EST. DISCLAIMERThis is educational content, not financial advice. Consult a qualified professional before making business or financial decisions.