McGuire Program Alum's Dream of Connecting the World Rests with Pillow

Pillow App
July 12, 2017
Sarah Mauet

Alumni Profile: Sean Conway, '07 Marketing and Entrepreneurship, Co-Founder and CEO, Pillow

Serial entrepreneur Sean Conway credits the support of the McGuire Program for his startup success with Notehall, acquired by Chegg, and now Pillow, which has raised $18 million.

The night before the 2007 McGuire Entrepreneurship Program business plan competition, Sean Conway snuck into Berger Auditorium around 7 p.m. and spent hours alone in the empty theatre practicing his pitch for RediRipe, his student team's new venture, which utilized color-changing stickers to indicate fruit ripeness.

Sean Conway, Co-founder and CEO, Pillow"I always heard that rehearsing the presentation in the actual place you're going to be doing it is better than practicing in front of the mirror, so I snuck in there and I sat there for four hours in the half-dark repeating the presentation," he said. "I was so nervous. I was a pretty big introvert so the idea of speaking in front of hundreds of people was terrifying for me, but that repetitiveness was key. We ended up winning the competition."

In the decade since, the successful serial entrepreneur has pitched to countless audiences, large and small, and even appeared on ABC's "Shark Tank."

"Now I've had to speak in front of tons of groups, and while I'm still nervous, it turns into excitement because of situations like that first competition where I proved to myself that I could pull it off," he said.

The McGuire Program was a life-changing experience for the San Diego native who once feared that he wouldn't get into the University of Arizona or its competitive top ranked entrepreneurship program.

He needn't have worried. He got accepted and quickly excelled in the yearlong hands-on program that engages students in the process of building a new venture from the ground up.

"As a student, I had always struggled even though I put in countless hours at the library," he said. "The McGuire Program, more than anything, gave me the self-confidence that I could be around these students, and be the general manager of a team, and win competitions. The foundational knowledge I got in the McGuire Program will always be key. It gave me the confidence to know that I could step out of school and jump into starting my own business right away."

Shortly after his McGuire Program competition win, Conway ran into Justin Miller, another entrepreneurship club member, in the UA library and their conversation about the challenges of school spurred the creation of Notehall, an online marketplace to buy and sell class notes.

Within 8 months, 40 percent of UA students were using Notehall, and by October 2009, Notehall appeared on "Shark Tank" where they received a $90,000 offer, which they later declined. By 2011, when the digital textbook company Chegg Inc. acquired Notehall for $9.5 million in cash and stock, the service had more than half a million users at more than 50 campuses nationwide.

Pillow Residential LogoAbout a year and a half later, Conway was the keynote speaker at IdeaFunding 2013, which is where he chose to unveil his next new venture, a short-term rental management software platform. The concept has developed into Pillow Residential, which provides multi-family building owners more transparency when their renters list units on Airbnb, ensures compliance with local regulations, and allows for profit sharing. Pillow raised $2.65 million in 2015 and an additional $13.5 million last month.

"This is going to allow us to expand, hire the best folks, and go nationwide," he said. "It will help take us to the next level to deliver this vision I have. I'm excited about that."

Conway, who is frequent worldwide traveler (50 countries and counting) and an ardent supporter of inclusion, has a simple but bold vision for Pillow; he dreams of nothing less than connecting the world.

"When I travel, I develop so much empathy and understanding just from sitting down with someone over dinner, or having a conversation with someone and seeing them smile, and that's needed in this world now more than ever," he said. "I want to make sure that travel is not a luxury, but a choice. Allowing people not to feel anchored to their rent or their mortgage will allow them to subsidize travel or pay down their student loans or take their significant other on a life changing experience. That's what I'm trying to encourage. That's my motivation."

That desire to support connection is not just the company mission, it also drives the culture he's building at Pillow. Notehall's startup culture developed very organically, so this time around Conway intentionally is creating a culture with more structure. There are daily team standups, a weekly company standup with all 42 team members to help them get to know one another, and more opportunities for recognition.

"Being able to define our culture through the values that we look for in our hiring process, and that we look to grow within the organization, it's important," he said. "Little things like recognition. We have a trophy that is given out each week to someone who has exemplified our values, and everyone gets to vote on it. Those are the small things that we've learned the second time around are super important as we scale. We're building a culture that instills credibility and professionalism and we balance that with play. I'd say i'’s pretty unique in the startup culture."

Though Silicon Valley is highly competitive and he’s surrounded by countless other founders and aspiring entrepreneurs from Ivy League schools, Conway said his McGuire connection opens doors.

"I want McGuire students to know that as a UA entrepreneurship alum you have a lot of credibility and you can get venture capital funding," he said.

While the McGuire experience was pivotal to Conway's entrepreneurial journey, he believes that anyone can be an entrepreneur. It simply requires devotion, passion and building relationships, he said.

"This has been one of my largest priorities in life," he said. "I love building businesses that change the world. As long as you want it, you can get it."