Venmo (live with Andrew Kortina)

Andrew Kortina and Iqram met when they became freshman roommates at Penn. The first meeting was chaotic: Iqram arrived with his family, a van full of belongings, and a tennis-racket stringer for a small dorm room. Their early collaboration was similarly improvised. They built a PHP content-management system for an acquaintance's father, admitted that neither really knew how to program, and described the result as closer to a swindle than a consumer product.

Their first more deliberate consumer project was My Campus Post, a classified site for college students. Its differentiator was a school-based verification layer that could make transactions more trustworthy than Craigslist. The project attracted sign-ups and even had a launch party, but its college-user base was seasonal and difficult to retain. That experience gave them an early lesson in the difference between initial interest and durable usage.

Their attempts to meet Craigslist founder Craig Newmark also showed the founders' willingness to learn by doing, but exposed the limits of enthusiasm without preparation. They claimed to have a podcast they did not have, flew to San Francisco without research or equipment, suffered laptop and hardware failures, and asked poorly researched questions. After graduation they joined I'm In Like With You, an early Y Combinator company that later became OMG Pop, Draw Something, and then part of Zynga. They were underqualified for formal software engineering, but said the team taught them a great deal before the company pivoted from dating to casual games.

Venmo began as a nights-and-weekends project while Kortina and Iqram held jobs. Advisors including TicketLeap CEO Chris and Sam Lessin encouraged them to work on it full time after they had made progress and recruited friends as early users. Sam Lessin and his father became the first investors and helped assemble an early financing round, allowing the founders to leave their jobs. Lessin later became Kortina's co-founder at Finn; at the time, he was running drop.io, which the interview describes as an early Facebook acquisition, though the speakers were uncertain about its exact position in Facebook's acquisition history.

The interview corrects a possible oversimplification about Lessin's role at Venmo. He was not primarily responsible for the news feed. His more direct contribution involved Trust, an early feature that allowed one trusted user to withdraw money from another user's account without a separate action. The speakers compare the relationship to marriage without the legal obligations, and note that PayPal shut the feature down immediately after acquiring Venmo.

The news feed came from the founders' own behavior. They used Venmo on BlackBerry phones instead of text messaging, and the payments themselves formed a stream of social activity. This observation connected payment events with a visible record of friends' real-world activity, an early indication that Venmo could be more than a utility for moving money.