Andrew Kortina and the art of getting sidetracked

Before there was Venmo, there was an unsuccessful offer to exchange a website for a hundred chicken rolls. Andrew Kortina and his friend Iqram Magdon-Ismail were selling sites to Philadelphia businesses after college. At Kabobeesh, a Pakistani restaurant they liked, they proposed payment in food. The restaurant declined. It is a pleasing opening to a payments career: two future founders unable to sell a customer on paying in sandwiches.

The anecdote survives because Kortina kept it. His accounts of work leave room for the embarrassing proposal, the friend who stayed, the project that went sideways. Alongside Venmo and Fin, his public record contains philosophy, homemade writing tools, short films, and a screenplay that became less finished with further attention. The résumé is straightforward enough. The choices that connect its entries are more interesting.

A curriculum with no obvious job attached

At the University of Pennsylvania, Kortina began with computer science. He found he was learning through long stretches of programming homework and wondered whether tuition was buying him something he could not get elsewhere. Creative writing offered workshops. Philosophy offered difficult books and people willing to discuss them. He changed direction, eventually combining those majors with minors in computer science and logic.

His stated ambition was to study subjects he considered impractical. The experiment disappointed him in a productive way. Reading substantial arguments, finding their weak points, and reducing them to a few clear pages turned out to be useful preparation for persuading colleagues and customers. He later connected those habits directly to product, strategy, and fundraising decisions. The reading had followed him into the office.

The education argument grew larger in his later writing. He questioned universities that treated the diploma mainly as a route into a job. Practical instruction was becoming available elsewhere at lower cost. College, he argued, could give more attention to intellectual range and the judgment needed for citizenship. A founder asking what education is for can sound like a recruitment pitch. Kortina was asking what the recruitment pitch left out.

The note beside the money

Kortina and Magdon-Ismail met as randomly assigned freshman roommates in 2001. Before Venmo, they built a campus classifieds site and experimented with other services. They also joined the early team at iminlikewithyou; Kortina later worked at Betaworks on Bitly. By 2009, they were trying ideas together again. One involved buying music through a text message. Another involved the tedious business of paying back a friend.

Magdon-Ismail visited New York without his wallet. Kortina covered the weekend; repayment involved a check. Both already carried phones. The inconvenience gave their experiments a clear direction. In its early form, Venmo let someone send a payment by SMS, adding a note about what the money was for. Those notes made an everyday exchange feel like part of a conversation.

In a later interview, Kortina explained the intention as putting the shared moment in the foreground. Dinner, coffee, a show: the activity mattered; the dollars could recede. That attention to the surrounding experience helps explain why his interests in writing and software coexist so easily. A product arranges attention too. It decides which part of a transaction a person sees first, and which part feels like the point.

An employee called Lucas, everywhere

Venmo’s 2013 advertising campaign made room for another kind of shared moment: strangers on the subway wondering what on earth they were looking at. The team put an employee named Lucas into spare advertisements with deliberately ordinary statements. The ads offered commuters a face and a puzzle. Kortina remembered the pleasure of encountering the campaign in a station, its peculiar joke repeated through the space.

He gave his colleagues credit for the idea and its execution. His own contribution included a line about Lucas knowing time. What stayed with him was the group’s decision to make something so particular and absurd. A mobile payment service was an obvious enough destination for technological progress. This little intervention in a commute depended on these people, with this taste, choosing to do it.

That pleasure also makes his affection for software as a form of expression easier to understand. In his unconventional autobiographical writing, he talks about putting beauty where someone might stumble across it. A personal website can hold an argument, a joke, a conversation, or an experiment with the form itself. The reader does not have to arrive looking for art to encounter a bit of it.

The minutes that would not disappear

Fin, which he co-founded with Sam Lessin in 2015, pursued a different everyday frustration. An executive assistant could be useful to someone who could not employ one full time. Fin combined human assistants with software that helped them remember preferences and manage requests. The customer delegated a task; behind the interaction sat people, tools, and the accumulated context required to do it properly.

The assistant service ended in 2019 as Fin concentrated on analytics. Kortina’s later explanation was plain: even with an efficient team, requests took time, prices exceeded what many customers wanted to pay, and growth did not meet venture expectations. A reservation sounds small until someone must actually secure it. The simplicity of the request does not determine the amount of work behind the answer.

He subsequently published an archive for other builders exploring assistants. It includes operational details and answers to questions prompted by newer AI tools. The gesture is practical and generous: the difficulties become material somebody else can use. He would welcome a service that solved them. He misses having the assistant himself.

The question the software cannot settle

While building systems intended to make work more efficient, Kortina was also asking why work carries so much personal meaning. He traced that question partly to Anne Hall, a Penn professor whose seminars asked students to consider a work’s conception of human dignity. He carried the question into his reading of literature and film, then into his thinking about automation and social arrangements.

His talks and essays worry at the relationship between productivity and worth. If machines perform more tasks, what happens to people whose sense of purpose has been organized around doing them? The question reaches beyond a forecast about jobs. It asks how people learn to value one another, and how much of that judgment rests on usefulness to an employer.

With his collaborator Rob, he organized MIT IAP seminars on automation, consciousness, narrative, and film noir between 2017 and 2020. The subjects move between computation and interpretation. His 2018 conversation with Y Combinator’s Craig Cannon moves similarly, from work to consumption to the appeal of making something with a recognizable human character. He keeps pressing on the assumptions beneath the familiar vocabulary of success.

His writing about optimism is particularly resistant to easy reassurance. He wants a leader to acknowledge bad odds and still have a plan worth trying. In that account, effort need not wait for confidence that history will deliver a happy ending. The standard is the conduct of the people involved: whether they can be honest, take responsibility, and treat one another with dignity.

“I always want to work with my friends.”Andrew Kortina

One last revision, several months later

By the end of 2022, Kortina had a feature screenplay he felt ready to shoot. A creative producer was involved; a table read had happened. Then came another revision. The structure came apart, and the following months brought attempts at rebuilding. His account gives revision its proper menace. A document can become newer without becoming closer to done.

Smaller projects offered another way forward. In his January 2024 recap, he reported finishing Telling Mattresses Stories with Rob and making Lost Gloves, an experimental short rooted in exchanges of photographs with an Oakland friend. He also worked as a production assistant on other shoots. The former startup executive was learning the demands of another workplace from inside its crew.

His film life includes watching as well as making. The Oakland Film Club list runs from Pi in 2018 to a numbered two-hundredth screening, American Splendor, in October 2024. The selections range from animated films to westerns, comedy, and documentary. His website describes the gatherings as something he and Rob host, with personal remarks prepared as homework. Friendship has acquired a syllabus.

The programmer remains visible in the writer’s tools. In 2020, Kortina described moving his notes into a customized VS Code setup, with ordinary Markdown files and an extension he wrote for links and tags. The attraction was partly control: searchable files, flexible shortcuts, a system he could adjust. Even the apparatus for being sidetracked could become a small software project.

In the same 2024 recap, he described wanting to teach a creative writing workshop at a CUNY community college. Finding a way in had proved difficult. He kept asking. His ambitions were taking forms less easily compressed into a company title: a class, a finished script, small independent films, work that could find its audience online.

A later talk returned to childhood in Stewartsville, New Jersey. He and his sister built mountain-bike trails, spending more time shaping the route than riding it. An obstruction could turn a short job into days of work. Kortina remembered the problems as part of the attraction. It is a useful image to leave beside the finished products: someone in the woods, making a way through, with somebody he likes.