Stinky, a cat in upstate New York, received an unusual tribute: an oil painting. His owner, Danielle Schwartz, had not commissioned it. Chewy, the company that sold her pet supplies, sent it as a surprise. When the Associated Press reported the story in 2021, Chewy was sending select customers more than a thousand portraits a week. A retailer of cat litter had found a way onto the living-room wall.
The detail is funny because the categories seem so far apart. Pet food belongs in a cupboard. A painting belongs among things you love. Chewy’s wager is that the person buying one is thinking about the other. Understand the animal, and you have a better chance of keeping the customer.
- The habit: food, litter and medication create reasons to return.
- The machinery: Autoship pairs repeat deliveries with customer support.
- The next bet: turn the shopping relationship into a healthcare relationship.
The poodle beat the jewelry
Ryan Cohen and Michael Day founded Chewy in 2011 after preparing an online jewelry business. Cohen’s experience shopping for his poodle, Tylee, helped redirect them toward pets. They sold their jewelry inventory for 80 cents on the dollar. The abandoned idea had a price before the new one had a future.
They launched with 50 dog- and cat-food brands, using an outside fulfillment operation. Cohen and Day answered customer calls themselves, around the clock, without drawing salaries. Revenue reached $26 million by the end of 2012, but the business was losing money. Demand had arrived before the economics were comfortable.
Volition Capital invested $15 million in 2013. “Ryan had crushed all his numbers,” investor Larry Cheng told Forbes. The evidence that helped win funding was performance against targets, rather than a more elaborate pitch. Cheng later described a near-disaster as Chewy brought fulfillment in-house: software failed, the existing logistics provider changed prices, backorders accumulated and gross margins turned negative. His account of the transition makes the lesson unusually concrete. Owning the machinery could improve service; getting it running could exhaust the company first.
A calendar is a competitive advantage
A dog offers a retailer something a jewelry customer rarely does: a reasonably predictable consumption schedule. The bowl empties again. Chewy’s Autoship lets owners arrange repeat deliveries and adjust the timing or cancel. It removes the recurring chore of remembering to shop.
That changes the competitive encounter. Amazon, Walmart, Petco, PetSmart and the neighborhood pet shop remain alternatives. But a scheduled delivery means Chewy need not win a fresh search every time the food runs low. Reliability becomes part of what the customer is buying.
of net sales came from Autoship customers.
This includes their purchases outside scheduled orders. It is not a measure of automated deliveries alone. Quarterly results.In that quarter Chewy reported roughly 21.7 million active customers, defined around purchases during the preceding year. Those are buyers, not app downloads. The company’s expertise sits in the unglamorous work connecting them: merchandising, inventory, fulfillment, prescription processing and service when something goes wrong.
The bowl empties again.
The economic advantage of an ordinary habit
The kindness has a cost
The portraits and condolence flowers make sense within that recurring relationship. A bad interaction can jeopardize years of future orders. A thoughtful response can give someone a story they tell their friends. That is an economic interpretation, not proof that a particular bouquet paid for itself.
Chewy’s stated operating principles include putting customers first, acting as an owner, delivering results and earning trust. Its careers material describes pet-adoption reimbursement and employee shopping discounts. These are specific cultural signals; they do not tell us how every warehouse shift or service job feels.
The financial discipline matters. In fiscal 2025, Chewy generated $12.60 billion in revenue and $222.8 million in net income, a net margin of 1.8%. Advertising and marketing cost $824.9 million. A business can be profitable and still have little room for expensive mistakes.
Follow the customer into the clinic
Once a retailer knows which food an animal eats, medication and care become adjacent needs. Chewy launched its pharmacy in 2018 and introduced medication compounding and online veterinary guidance in 2020. CarePlus offers insurance and wellness options through partners including Trupanion and Lemonade. The policies come from those providers; Chewy is not the insurer.
Chewy Vet Care began opening physical practices in 2024. In May 2026, Chewy completed its acquisition of Modern Animal, a veterinary platform, for an estimated $399.8 million. It also bought equine-health supplier SmartPak for $175 million that February. These are purchases of new capabilities, with integration work attached. Together the two deals committed roughly $575 million of purchase consideration, before separately reported transaction costs. The sum makes the healthcare strategy tangible.
For pet owners, the distinctions matter. Free online chat supplies general guidance. The current virtual-visit page advertises $49.99 veterinarian video appointments, with prescriptions available at professional discretion, in seven named states. A chat window cannot supply every examination, procedure or emergency response a pet needs.
Earn the next order
The model keeps changing. October’s Chewy+ offer advertises a $59 annual membership after a trial, free shipping without a minimum, and rewards weighted toward food and pharmacy. Veterinary diets and other merchandise earn a lower rate. The current offer makes the company’s priorities visible in the benefits.
What can another business copy? Find a problem that returns on a schedule. Give customers control over the repeat purchase. Make service useful at the awkward moments. Then calculate whether the resulting relationship covers acquisition, support and delivery costs.
The conditions are demanding. Sporadic purchases offer fewer chances to earn back those costs. A customer who needs supplies immediately may prefer a nearby store. Heavy parcels, weak delivery density and unreliable fulfillment can consume the margin. Chewy’s story rewards attention to the second order. It also shows how much work must happen before that order deserves to arrive.