Pregame Your Launch Before Your App Exists (w/ Amanda Bradford) | E2355

How The League built a waitlist before its app existed

Takeaways

• The League recreated business school's closed community. Bradford's business school class of 300 produced about 30 couples, and she wanted that close-knit setting in an app. Users got three or five matches at 5PM, called five at five, against Tinder's endless swiping, and never saw former coworkers.
• Exclusivity and scarcity powered demand. The League used LinkedIn verification, as the first dating startup on its API, and an admissions process where not everyone got in. Bradford hand-reviewed every application, and the waitlist screen counted down remaining slots. The elitist angle in press cut both ways.
• A fake upgrade button tested willingness to pay. The League did not monetize for its first year and a half. A fake upgrade that never billed showed about 15 percent of users would pay a $15 membership fee. Bradford later closed $2m in funding.
• Stripe has scaled enormously since 2017. In 2017 Collison described billions in revenue, about 124 countries and nearly 700 employees. The hosts cite 2025 payment volume near $1.9tn, up 34 percent, and 5m businesses with first-half 2026 revenue up 41 percent.
• Stripe began as a developer tool. The team then saw the wider payments problem, when only about 2 percent of consumer spending happened online. Collison and his co-founder left school for a summer and raised early money from Sam Altman, Sequoia and others.
• An unnoticed eight-hour outage was Stripe's low point. About six months in, the API went down at 4AM after an upstream switch failed, and it stayed down almost eight hours. Collison said the worst part was that nobody seemed to notice. The hosts say being ignored can be worse than criticism.
• Wilhelm doubts Stripe's reasons to stay private. Collison said in 2017 that Stripe would delay going public as long as possible, citing its early stage and long time horizon. Wilhelm says Microsoft, Apple, Alphabet and NVIDIA grew most of their size while public, and calls the reasoning specious.

Bradford's prelaunch sequence

1. Hire an iOS engineer as a rented co-founder, with equity that vests on App Store launch, and spend about five months building the app.
2. Run small events during the build, such as a Blue Angels boat party at $300 per person and a shopping night at a store opened late.
3. Collect founding members by going door to door, and build a waitlist.
4. Send about 30 press pitches before launch, which won coverage from TechCrunch and Business Insider.
5. Open San Francisco to 500 people, then expand to New York and Los Angeles. She advised against launching in 155 cities and said she would have capped it at 20.