John Kobs keeps making room for the next idea

John Kobs once helped build a rental business, then helped dismantle the way it made money. Apartment List was bringing in millions of dollars. It had customers, employees and something entrepreneurs are ordinarily advised to cherish: a working business. Kobs and his colleagues decided the model was getting in the way of the experience they wanted renters to have. Success had become an awkward tenant. They asked it to move.

That decision is a useful introduction to Kobs, the Apartment List co-founder and founding CEO who now runs Giant, a storytelling company for children. His career has moved through finance, rental marketplaces, digital art and interactive entertainment. The subjects change. The appetite for revising the arrangement keeps turning up.

A friendship advertised on an index card

Long before the apartment listings, there was a smaller matching problem. As a boy spending summers on an island in Lake Erie, Kobs wanted someone to play with. His father put a three-by-five-inch card in the post office advertising a softball game. The communications infrastructure was modest; the ambition was perfectly reasonable.

Kobs and his parents arrived. At first, nobody else did. Eventually a car pulled up and out stepped Chris Herndon, sporting the sort of long blond hair that made Kurt Cobain a useful point of reference. The softball was apparently dreadful. The friendship lasted, and Herndon later became a co-founder of Apartment List.

It is a pleasing beginning for someone who would spend years building marketplaces. A notice, an unmet wish, a stranger who becomes a collaborator. Even before the software, there was the question of getting the right people to turn up.

Ohio, a football jersey and a Manhattan lease

Kobs grew up in Granger Township, Ohio, and graduated from Case Western Reserve University in 2003. He studied finance, played running back and served as a football captain. His father and older sister were also Case Western alumni. Finance was the intended profession; entrepreneurship arrived by a less orderly route.

In 2005, he drove from Cleveland to New York with a friend, allowing himself a day to find an apartment. He encountered bait-and-switch listings, attempts to take his deposit and places occupied by squatters. He eventually secured a home. The rental process had also acquired a future critic with an unusually durable grievance.

There is nothing especially glamorous about being irritated by an apartment search. That is part of the appeal of this origin. A new job requires a new address. The address should not require detective work. Kobs carried the frustration into a business career that would eventually concentrate on precisely that gap.

Before the software worked, people made phone calls

Apartment List launched publicly at TechCrunch Disrupt in September 2011. Its early proposition brought rental inventory together in one place. For a renter confronting scattered websites, the attraction was straightforward: fewer places to look, a clearer view of the possibilities.

By November 2013, the company had roughly 600,000 listings and a 57-person team. It had assembled about 100 data partnerships. Kobs said the business had been profitable for three years. Almost half its monthly visitors were arriving on mobile devices, even before an Android app had launched.

Some of the work was determinedly unglamorous. Team members called landlords who advertised offline and checked that listings had good photographs. The business also arranged parties where prospective roommates could meet. An online marketplace apparently still benefited from getting people into the same room.

Those details give the early company texture. A map and a search interface were the visible product. Behind them sat a great deal of telephone work, negotiation and inventory maintenance. The apartment might be discovered online; somebody still had to make sure it was worth discovering.

The expensive art of changing your mind

Then came the reset. The original aggregation model depended on other rental websites. Their priorities and constraints limited what Apartment List could do for its own users. Kobs and co-founder Chris Erickson wanted a closer relationship with both sides of the transaction.

He later described sacrificing a business with about $17 million in annual revenue to pursue another model. Experiments went wrong. Hiring had run ahead of what the company could support, and it laid off 20 percent of its team. This was a decision with consequences for people, as well as for a revenue chart.

The model that emerged charged for a successful move-in. It made the renter finding a home central to how the company earned its money. There is an appealing directness to that arrangement: the platform gets its reward when the transaction produces the outcome everyone came for.

By January 2018, Apartment List reported around four million units and announced a $50 million funding round. It also had distribution relationships with Realtor.com and Facebook Marketplace. These were ways to reach people where they already looked, an important consideration for a service most customers need only occasionally.

A finance graduate learns to delegate the books

The less theatrical changes mattered too. Kobs has been candid about the limits of his own expertise. Despite his finance background, he said he had little enthusiasm for accounting and did not consider himself particularly good at it. There are cheaper ways to discover humility than reconciling a growing company's accounts, but few are quite as thorough.

Apartment List became airCFO's first client. The relationship began before its Series A and continued as the company added its own controller and CFO. Specialized help remained useful as the accounting work became more complicated.

His description of that arrangement is revealing. Founders move between sales, product decisions and spreadsheets; the ability to wear several hats does not guarantee that each one fits. Bringing in people with deeper expertise gave the team more time for renters and property managers.

In his 2022 reflections, Kobs counted more than 790,000 families housed through the platform since 2014 and over $170 million raised. He also pointed to profitability. These were measures of a company that had survived its own revisions and found a way to keep operating.

Leaving the chair at the head of the table

On April 4, 2022, Kobs announced he was leaving the day-to-day CEO role. Matthew Woods, an executive who had spent five years at Apartment List, would succeed him. Kobs would continue as chairman.

“The role of any great CEO is to work themselves out of a job.”

John Kobs, 2022 founder's letter

It was a pointed definition of leadership from someone handing over the job in question. He recalled the early Palo Alto office, where passing trains shook the floor, and repeated brushes with running out of business. By his departure, the organization had grown to more than 250 people.

The farewell also made room for other interests: family, art, creativity and Web3. After years of asking people where they wanted to live, he was giving himself some room to decide what to do next. A succession plan can be an act of imagination too.

Meet Douglass, who makes music

In September 2022, Kobs introduced Wildxyz and explained another name he had been using: Douglass. Under that creative pseudonym, he had released music on Spotify and collected digital art. The founder who organized rental inventory also wanted a place to experiment without arriving as the person in charge of Apartment List.

He traced the interest back to collecting baseball cards as a child. In early 2021, he began collecting NFTs and became interested in the artists behind them. Wild was an attempt to give their work more support and a richer setting.

The details are more interesting than the career category. Making music, collecting objects and building a marketplace are different activities. For Kobs, they had begun to occupy the same conversation. Wild offered a place to see what might happen when those interests met other people's expertise.

Its first residency ran for 12 weeks, beginning in November 2022 and culminating in releases of artwork in January 2023. A $7 million seed round followed, led by Matrix Partners, with investors including Reid Hoffman and Kevin Lin.

The residency model gave artists structure, technical support and a community of peers. Participants included Sarah Friend, Jonas Lund and Serwah Attafuah. Instead of simply making another place to buy an image, Wild was organizing the conditions in which artists could develop work. That interest in participation would soon find a much younger audience.

The next audience wants a say in the story

Giant launched in May 2025. By February 2026, it had announced an $8 million seed round led by Matrix, Decasonic and Griffin Gaming Partners. Kobs is its CEO and co-founder; David Silverman is his fellow co-founder. Children can create episodes, appear as cartoon characters and talk with characters that respond to them.

At the funding announcement, the company reported more than a million minutes of conversation and over 200,000 personalized episodes. Those figures describe early use, rather than the final shape of the business. The proposition is that children will want to influence what happens, bringing their own ideas to characters and worlds.

His public posts make the personal connection plain. He describes camping, karaoke, dance and soccer with his daughter. He wants the time she does spend with a screen to include making things. A feature that turns children's drawings into stories carries that wish into the product.

Giant's website now invites children to explore ancient Egypt, dinosaurs and the moon. The scenery is expansive; the invitation is intimate. What would you like to happen? After years spent matching people to existing spaces, Kobs is working on spaces that respond to their inventors.

There is a long distance between an Ohio post office and an AI character. Still, that first index card belongs in the story. It offered an activity, waited for someone to answer and turned an ordinary afternoon into a lasting connection. Kobs keeps finding new ways to put the invitation out.