19: GUEST - Julia O'Mara, Pickle

NOTE: Remember – The Venture Capital Problem Set is also due today. The Problem Set takes a considerable amount of time to complete so plan ahead and do not put it off until the last minute.

NOTE2: We will be combining the two 10:15a sections in 217 Towne today. Please report to 217 Towne so we may begin promptly at 10:15a.

Today’s guest speaker is Julia O’Mara, co-founder and COO of Pickle, a peer-to-peer rental marketplace where users can rent, sell, and buy personal fashion items. Pickle takes a 20% cut of each transaction. They also operate a storefront in Manhattan’s West Village. Pickle raised $8MM in their 2023 seed round at a $30 million valuation and just closed a $12MM Series A funding round at a $60MM valuation. Julia, and her co-founder, Brian McMahon, were selected for Forbes 30 Under 30 in Retail & Ecommerce.

Julia previously worked as a product manager at Blackstone, where she focused on creating data analytics and data visualization solutions for the fundraising teams. Prior to Blackstone, she worked as a Business Technology Analyst Summer Scholar at Deloitte and a Project Management Intern at TIC Gums.

Julia earned a BSE in Materials Science & Engineering, with a concentration in nanoscale materials, and a minor in Engineering Entrepreneurship at the University of Pennsylvania. Julia was a high school All-American lacrosse player and a member of the women's championship lacrosse team at Penn.

• Study Pickle's website to learn about their company and product offering.
• To check out their app, go to: https://apps.apple.com/us/app/pickle/id1551736097.
• Read the Authority Magazine interview with Julia and 5 leadership lessons she learned from her experience.
• Read the Tech Crunch article about Pickle and its $8 million seed round, and their supplemental blog post.
• Read the blog post about their storefront opening as also covered in Women’s Wear Daily.

Based on the above online sources, knowledge you have gained in class this semester, and additional related research you may conduct, type up a list of 5 questions to ask Julia, time permitting, during the Q&A session following her talk. Submit your list of questions, as a PDF file, on Canvas before the beginning of class. Questions will be graded based on their substance and the evident level of effort in your research about the speaker. Vague, generic questions of little substance will be penalized.

Out of courtesy to our speaker plan to arrive at class a few minutes early so the class can begin on time without interruption.

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1. Building & Sustaining a Peer-to-Peer Community

Pickle is built around a community-driven model where users trust each other with items often valued highly. Could you talk about how you foster and maintain a sense of trust, safety, and engagement among your community as you scale?

2. Balancing Growth, Brand Image & Operational Complexity

Operating both an app-based marketplace and a physical storefront can be complex. How have you balanced these two channels—particularly around operations, logistics, and branding—to ensure a cohesive Pickle experience online and in-person?

3. Data Analytics & Personalization

Your background includes experience in data analytics at Blackstone. What role does data play at Pickle in driving user engagement, personalization (e.g., recommended items), and operational decisions (such as inventory selection for the West Village storefront)?

4. Handling Fundraising & Strategic Partnerships

You recently raised a $12MM Series A at a $60MM valuation. Could you describe the biggest lessons you learned during these fundraising rounds, and share insights on how you think about strategic partnerships or exit opportunities in the peer-to-peer fashion space?

5. Leadership & Team Building

You’ve been recognized in Forbes 30 Under 30 and have shared “5 Leadership Lessons” in Authority Magazine. Can you elaborate on how these lessons shaped the way you lead at Pickle today, especially in recruiting and motivating a team that believes in the company’s vision?

Leveraging Diverse Backgrounds:

How has your experience in materials science and data analytics—combined with your roles at Blackstone and Deloitte—influenced the development of Pickle’s technology and overall operational strategy?

Balancing Online and Physical Presence:

With Pickle’s dual approach of a digital marketplace and a Manhattan storefront, what challenges and opportunities have you encountered in creating a seamless customer experience that builds trust and enhances user engagement?

Marketplace Economics and Fee Structure:

Pickle takes a 20% cut on each transaction. Can you explain how this fee structure was determined and how it balances profitability with ensuring value for both renters and sellers in a competitive peer-to-peer market?

Building Trust in Peer-to-Peer Rentals:

Peer-to-peer marketplaces often face hurdles around trust and quality control. What strategies has Pickle implemented—perhaps leveraging data analytics or community feedback—to foster a reliable and secure environment for users?

Growth and Leadership Lessons:

Reflecting on your Forbes 30 Under 30 recognition and the leadership insights you shared in the Authority Magazine interview, what key lessons have been most critical in scaling Pickle, and how do you plan to apply these as you drive future innovation in the digital fashion rental space?