Before David Oates built a marketplace for other people’s clothes, he built a website because his mother said he could. A neighbor in Charlotte was opening a restaurant. Oates had fixed the television before, which was apparently evidence enough that he could handle the internet. He agreed, figured it out, and soon made sites for lawyers and small businesses around town. The first stack was ActionScript and Macromedia Flash. The lasting tool was closer to temperament: enter an unfamiliar system, notice where it resists, then make the next action easier.
At Myers Park High School, a sprawling public school in Charlotte, he worked on the live morning announcements with William Ault, another student interested in Apple products, audiovisual gear and startups. On the school newspaper, Oates owned the centerfold, a two-page spread freed from the paper’s usual layout. It let him mix reporting, interviews, photography and design. Long before his job titles settled into CEO or founder, he was already moving between disciplines without asking permission from the boundaries.
The education between the lines
Northeastern University gave Oates a view into Boston’s startup world. Its Entrepreneurs Club brought local builders to campus each Tuesday. He also joined Rough Draft Ventures, the General Catalyst-backed student fund, where young founders arrived to pitch every week. He learned to inspect an idea and its evidence, but the formal degree did not hold him. After roughly a year, he left for HubSpot.
He entered HubSpot as an engineer, then moved onto a small team building an email tool that would evolve into the company’s CRM. Within months, he was its lead designer. The shift fit him. Code was useful, but the question of how a person understood the product was more compelling. He helped ship the CRM, briefly returned to school, then left again without graduating. A month in Japan followed. So did freelance projects, small apps, writing and the unsettled feeling of having useful skills without one direction for them.
“Start by assuming it’s not them, it’s you.”David Oates on design and leadership, 2018
That line came from a short essay on management, but it describes his product logic too. When a user does not understand a design, blaming the user closes the feedback loop. When an employee misses the mark, he wrote, first inspect the relationship, context, knowledge and attention surrounding the work. It is a demanding kind of empathy because it assigns the leader more work, not less.
A marketplace, viewed from a moped
In the fall of 2015, Oates started delivering for DoorDash around San Francisco on a scooter. He went from zero deliveries in September to the platform’s highest-volume, top-rated driver nationwide in October. The month offered a compressed education in incentives and logistics: burgers, pad thai, forgotten napkins, one milkshake spilled across the back of the moped, and ten cases of Red Bull balanced toward a hotel guest who could not be found.
The Red Bull became his problem. Support told him he could eat or discard an abandoned order after fifteen minutes. Neither was practical. He eventually returned the cases to the store. Beneath the comedy was the essential marketplace lesson: every clean transaction on a screen rests on messy work performed by a person somewhere else.
At nearly the same moment, Ault called. A dress-rental app at the University of Mississippi needed design help. The idea had grown from a specific Southern college ritual. Sorority calendars could demand a different dress for football weekends, parties and formal events. Closets had idle inventory. Students lived close enough to exchange it. Oates designed the first version remotely, watched it take off at Ole Miss, gave up his San Francisco apartment and moved to Oxford, Mississippi.
The team entered Y Combinator in 2016. During its interview, Sam Altman asked what they knew about two-sided marketplaces. Oates mentioned his DoorDash month and added that he had once delivered Indian food to Altman’s home. The room loosened. Curtsy got in.
The dangerous middle
Curtsy’s rental marketplace worked. That was not the same as working well enough. The company expanded from ten campuses to thirty. It created ambassador programs, tried subscriptions at the University of Georgia, shipped rentals between schools and operated a managed store in Tuscaloosa for six months. Users earned a reported $1 million renting their closets. Each experiment proved there was real demand while exposing a ceiling.
Special-occasion rental required a special occasion. The dress had to arrive on time, fit, survive the evening, come back and be clean for the next booking. A promotion could lower the price but could not create an event. Outside the dense Greek-life culture of large Southern schools, demand thinned. Summer emptied campuses and shut down local markets just when the YC program applied pressure to grow. The team deferred Demo Day, eventually appearing roughly three years later.
Oates later put the danger plainly: “A moderate level of success is more dangerous than having a complete flop.” A flop forces a decision. A modestly successful model supplies just enough evidence to continue. For Curtsy, two years went into trying to make rental behave like the team wanted. A third went into disrupting it.
What the closet was saying
The escape hatch had been sitting in customer requests: let people sell. Curtsy first added buying and selling beside rental. The behavior diverged quickly. Renting remained pinned to dresses and dates. Resale absorbed activewear, denim, sunglasses, swimwear and ordinary clothes. A discounted pair of leggings could be an impulse purchase. A swimsuit bought in December could wait for spring break. Shipping connected Alaska to Mississippi without requiring density in either place.
In June 2018, Oates wrote to Curtsy’s community that the company would end rentals. He acknowledged that the old model spent more than it made and called the decision bittersweet. On July 2, the buy-and-sell product took over. Within months, the direction was clear. Removing the calendar expanded the market.
“The big gap in the market is really for casual sellers - people who are not interested in selling professionally.”David Oates, 2021
That casual seller became Curtsy’s organizing customer. On many resale platforms, selling well can resemble running a small media business. People cultivate followers, share listings and learn platform rituals. Oates described Curtsy differently: an item meritocracy. A new seller with no audience can post the right brand at the right price and reach the feed.
Making that promise credible requires work behind the curtain. Curtsy combines software with human review to identify attributes, suggest prices, crop photos and standardize listings. The company developed shipping kits with mailers and adhesive label sleeves. For sellers without a printer, it offered mailed labels. A tap could arrange USPS pickup. A buyer could later relist a Curtsy purchase using its existing information and photos. Each step recognizes that someone cleaning a closet probably does not want a second career in fulfillment.
Less listing work + less audience-building + less shipping friction = more ordinary closets able to become supply.
This is where Oates’s mixed background becomes legible. The school-paper designer cared how the feed looked. The engineer could see which fields and tools made a listing reusable. The delivery driver understood that the physical handoff was part of the digital product. The investor-in-training could see the feedback loop: lower the cost of supplying the marketplace, improve liquidity, make the marketplace more useful to buyers, then attract more sellers.
Small details, larger bets
Curtsy reported reaching roughly $25 million in annual gross merchandise volume with the four co-founders and two or three additional core team members. By late 2020 it was facilitating about 85,000 monthly transactions. In January 2021, the company announced an $11 million Series A led by Index Ventures. Oates’s preferred explanation for its differentiation remained almost unfashionably plain: design and customer experience.
He does not confuse devotion to detail with timid iteration. In a 2022 marketplace interview, he argued that companies need periodic bets designed to maximize upside, even when the current trajectory looks strong. Curtsy’s own history supplies the proof. Better rental flows could not remove rental’s calendar. The consequential move was changing what the marketplace was for.
His public voice keeps that tension alive. On the five-episode podcast Something Like That, he discussed hiring, productivity and pivots with a deliberately provisional tone. The title celebrates conversational looseness: stories paraphrased, names occasionally forgotten, opinions allowed to change. It is an apt posture for someone whose company improved when its founders let the evidence revise the plan.
In 2023, Oates returned to Oxford to moderate a Curtsy founder panel for student entrepreneurs. The company had traveled from a campus closet to a national marketplace, while the original insight remained close by: useful businesses often begin with a habit people already have and a frustration they have learned to tolerate.
The neighbor’s restaurant website, the HubSpot email tool, the stranded Red Bull and the Curtsy shipping kit share a family resemblance. Someone is trying to get from here to there. The system has made the route awkward. Oates’s work has been to stand inside that awkwardness long enough to notice what should move.