Startup Success Twofold: Sean Conway ’07 BSBA (Entrepreneurship and Marketing)

March 7, 2019

Sean Conway

Sean Conway ’07 BSBA (Entrepreneurship and Marketing)

Sean Conway ’07 BSBA (Entrepreneurship and Marketing) needed a way into the McGuire Entrepreneurship program. 

He didn’t have the best grades. So why not start an entrepreneurship club? he thought. This turned into his ticket to a life of start-ups.

“Our club advisor and an entrepreneurship program professor was impressed with how we ran the club,” Sean says. “He said to me ‘You have probably the worst GPA I’ve ever seen trying to get admitted to the entrepreneurship program but I’m going to stick my neck out there and let you in. But you have to make me proud.’”

As a student, Conway was confident that his big break was on its way. “I didn’t have a job and nor did I want one because I was intent on starting a business after college,” he says. 


Sean Conway
Sean Conway ’07 BSBA (Entrepreneurship and Marketing).

He remembers he was camped out at the Integrated Learning Center on campus (“because they had the best internet out there”) when a fellow member of the entrepreneurship club, Justin Miller ’10 BSBA (Accounting),  stopped by to ask a question about posting notes online. The two ended up chatting for hours, spit-balling their first business idea. 

It started as an online marketplace where students could buy and sell notes from their courses. It proved successful enough that they hired two other people from the Eller community—and then an additional eight students to help run it. Three and a half years later, their company, Notehall, scaled to 86 colleges and 400,000 students and was ultimately sold to Chegg for just shy of $10 million. 

Conway went on to work Chegg for a few years, before he and Miller got the band back together for their next venture. 

The two were attending a wedding of mutual friends when they asked themselves “why aren’t we renting our place out while we’re gone?” And from that question, the idea for Pillow was born. 

Founded in 2013, San Francisco-based partners with multifamily owners to help residents list their apartments as short-term rentals without violating their leases in the Bay Area but has since grown to serve 35 cities across the country. The company lists client’s properties on rental sites and offers online tools to facilitate with the management of the properties including guest booking, key exchange, cleaning, maintenance and guest communication. 

Pillow’s success comes from Conway’s ability to surround himself with an exceptional team and listen to what consumers are really asking for. 

“Housing has always been stuck in a one year lease, and we’re seeing people wanting experiences and to live in multiple places,” he says. 

Clearly Conway isn’t the only one who noticed: Pillow had already raised $16 million in capital when it was acquired by Expedia in October of 2018. Terms of the deal were not disclosed. 

Through all of Conway’s success, he hasn’t lost sight of what—and who—helped get him there: “Just before graduation my club advisor, Jim Jindrick, took me into his office and said ‘Sean, when you make your first million dollars, all I ask is you take me and my wife to Paris for dinner at the Eiffel Tower’.” 

A few years back, his advisor settled for dinner at a French restaurant in Tucson during one of Conway’s visits. But now Conway says, “I’m going to tell him, ‘make time on your calendar. You’re going to Paris’.”


Photos by Julius Schlosburg.