Masters of Scale
Masters of Scale

What's the hidden business behind your business? w/Rent the Runway's Jenn Hyman

Rent the Runway co-founder Jenn Hyman knows: Behind every successful business is another business backstage, one you might not expect. Rent the Runway is known for creating a glamorous "closet in the cloud,” but as Hyman explains, it achieved unicorn status by mastering a few less glamorous bus

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WaitWhat HostReid Hoffman Guest

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Episode Summary

Executive Summary: This episode argues that scalable companies must master the “business behind the business.” Using Kevin Venardos’s traveling circus and Jen Hyman’s Rent the Runway, Reid Hoffman shows how hidden systems—operations, logistics, data, labor, and partner relationships—create trust, differentiation, and growth. The lesson: build the back end early, because it can become the real moat.

Main Topics: Mastering the business behind the business (Priority: 5/5): Reid frames the episode around the idea that every scaled company has an invisible operational engine that powers the public-facing product, and that this engine often determines whether a company can grow sustainably. Venardos Circus as a startup (Priority: 4/5): Kevin Venardos explains how he turned a dream into a touring circus and learned that success depends not only on performance but also on permitting, location selection, staffing, and fast tent logistics. Rent the Runway’s origin and category creation (Priority: 5/5): Jen Hyman describes the founding insight behind Rent the Runway: customers wanted access to fashion without ownership, and the company could build a 'living closet' that adapts to life changes. Operations, labor, and logistics as competitive advantage (Priority: 5/5): Rent the Runway’s customer experience depends on warehouse systems, dry cleaning, repairs, seamstresses, quality control, and careful end-to-end logistics that cannot be outsourced without losing the core value. Data as the hidden moat (Priority: 5/5): The company’s return-heavy model generates unusually rich data about fit, usage, wear, and customer preferences, enabling better inventory decisions, design partnerships, and new subscription offerings. Relationships and industry trust (Priority: 4/5): Hyman emphasizes that fashion is built on trust, so Rent the Runway had to win over designers and department-store leaders early rather than fight them, using relationships to secure supplier permission and legitimacy. Scaling requires systems and consistency (Priority: 4/5): The episode closes by showing that visible brands rely on invisible systems; if backend operations fail, customer trust and growth collapse, even for a high-profile, data-driven company.

Key Arguments: A company’s public product is only as strong as the operational system behind it; hidden infrastructure is often the true source of scale. Founders should design backend systems early instead of patching them later, because the core business model may depend on them. Rent the Runway is as much a technology and data company as a fashion company, with engineers and data scientists central from the start. Specialized hourly labor is as strategically important as executive talent because quality restoration and logistics are core to the product. Data from repeated rentals is far richer than traditional retail data and can be used to improve product, operations, and brand partnerships. Winning trust from incumbents and suppliers can be more valuable than trying to bypass them, especially in relationship-driven industries. Speed and control in logistics are part of the customer experience, not just operational details. Some backend capabilities can become standalone businesses or major strategic assets, as shown by AWS and similar examples.

Data Points: Tent setup time: 4 hours - Kevin Venardos says his circus can set up its tent in four hours, compared with much slower setups for larger circuses. Trailers needed for setup: 1 semi - Venardos notes his circus uses only one semi, unlike larger circuses that require dozens. Tent stakes: 66 stakes - The pole tent has 22 poles, each anchored by three stakes. Peak weather at launch: 120 degrees outdoors - Kevin describes the early show as a 30-minute circus musical performed outdoors in extreme heat. Initial funding ask for honeymoon registry: $2 million - Jen Hyman pitched Starwood Hotels for funding to start a honeymoon registry business. Time at Starwood building registry: 3.5 years - Jen says she spent three and a half years at Starwood building the honeymoon registry business. Email attempts to reach Diane von Furstenberg: 12 iterations - Jen and Jenny wrote cold emails to 12 different versions of [email protected] until one worked. Discounted rental price versus retail: 5% to 10% of price - Jen told Neiman Marcus she wanted to rent designer dresses for a fraction of the retail price. Reported tag-on return behavior: 70% - Jim Gold told Jen that customers buying dresses in his store kept the tags on and returned them about 70% of the time. Corporate employees who are engineers/data scientists/product managers: 80% - Jen says the majority of Rent the Runway’s corporate employees are technical roles. Customers’ product feedback frequency versus traditional retail: Over 100 times a year - Jen says Rent the Runway gets customer data far more frequently than traditional retailers. Company valuation: $1 billion - The episode notes Rent the Runway reached a $1 billion valuation. Order cancellation disruption: Weeks - A new software and racking system caused weeks of cancellations and service disruptions. Customer compensation for disruption: $200 cash refunds - Jen refunded customers and gave an additional $200 in cash during the service disruption. AWS market share cited: 48% - Reid cites AWS as an example of a backend business becoming a dominant standalone platform. Initial New York Times launch impact: 100,000 new signups - Rent the Runway’s launch placement in the New York Times business section drove major signups.

Pivotal Quotes: "I think it's one of the most exciting parts of the experience that I provide people is seeing that tent at a distance and then stepping inside of it." — Kevin Venardos: Kevin explains why the circus tent is central to the customer experience and the magic of the brand. "We are getting data from our customers over 100 times a year." — Jen Hyman: Jen describes how Rent the Runway’s rental model creates unusually rich behavioral and product data. "The business behind your business is most effective when it's invisible to the consumer." — Reid Hoffman: Reid closes with the core thesis that hidden systems create seamless customer experiences and scalable businesses.

Implications: Founders should treat operations, data, and labor as strategic assets, not back-office chores. The companies that scale best build trust and differentiation through invisible systems that can become durable moats.

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About Masters of Scale

On Masters of Scale, iconic business leaders share lessons and strategies that have helped them grow the world's most fascinating companies. Founders, CEOs, and dynamic innovators join candid conversations about their triumphs and challenges with a set of luminary hosts, including founding host Reid Hoffman (LinkedIn co-founder and Greylock partner). From navigating early prototypes to expanding brands globally, Masters of Scale provides priceless insights to help anyone grow their dream ente...

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